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WO2015165960A1 - N-acylamidine compounds - Google Patents

N-acylamidine compounds Download PDF

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Publication number
WO2015165960A1
WO2015165960A1 PCT/EP2015/059330 EP2015059330W WO2015165960A1 WO 2015165960 A1 WO2015165960 A1 WO 2015165960A1 EP 2015059330 W EP2015059330 W EP 2015059330W WO 2015165960 A1 WO2015165960 A1 WO 2015165960A1
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alkyl
radicals
unsubstituted
alkoxy
group
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French (fr)
Inventor
Karsten KÖRBER
Martin John MCLAUGHLIN
Birgit GOCKEL
Wolfgang Von Deyn
Jochen Dietz
Matthias Pohlman
Kenichi Kojima
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to ⁇ , ⁇ '-substituted amidinecompounds of the formula (I) as defined herein, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds.
  • the invention also relates to the use of the N,N'-substituted amidinecompounds of the formula (I), their stereoisomers, their tautomers and their salts, for combating invertebrate pests.
  • the invention relates also to methods of combating invertebrate pests, which comprises applying such ⁇ , ⁇ '-substituted amidinecompounds.
  • Invertebrate pests such as insects, acaridae and nematode pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.
  • WO 91/04965 describes insecticidall active amidine compounds of the formula A
  • R2 is, inter alia, hydrogen, alkyl, carbamoyl
  • R3 is, inter alia, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl
  • Z represents N or CH and R 4 is cyano or nitro.
  • EP 376 279 describes insecticidally active guanidine derivatives of the formula B
  • WO 2008/009360 describes compounds of formula A similar to those of WO 91/04965, wherein Ri is aryl, heteroaryl or heterocyclyl, Z is N , F3 ⁇ 4 is halogenated alkyl, alkenyl or cycloalkyl, R3 is alkyl or cycloalkyl, R 4 is CN.
  • Het is a heterocyclic radical, n is 0, 1 or 2
  • Ri is hydrogen or alkyl and R2 is hydrogen, alkyl, a primary, secondary or tertiary amino group, alkoxy or thioalkyl.
  • the pesticidal activity of the compounds is not satisfactory. It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects and acarid pests.
  • X is O or S
  • Het is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen and nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R 6 , wherein k is an integer selected from 0, 1 , 2, 3 or 4;
  • R 1 , R 2 are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-,
  • R 3a is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 , C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R 10 ,
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 1 is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R 10 ,
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 2 is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • Cyc 3 -Q 3 where Cyc 3 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,and where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • Q 3 is a single bond, Ci-C4-alkanediyl or C2-C4-alkenediyl;
  • R 4 and R 5a may also form a bivalent radical, selected from the group
  • R 5a if present, is selected from the group consisting of hydrogen, OH, CN, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Ci-C6-alkoxy, C2-C6- alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8-cycloalkyl-Ci-C4-alkoxy, wherein each of the 10 last mentioned radicals are unsubstituted, partly or completely
  • phenyl and phenyl-Ci-C4-alkyl where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ;
  • R 5b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • Cyc 4 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 4 is Ci-C4-alkanediyl or C2-C4-alkenediyl; or R 5a and R 5b , if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the two aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7b ; where, independently of their occurrence, n is 0, 1 or 2;
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 7 independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF 5 , Ci-C 6 -alkyl, d-C 6 -haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C 2 - Ce-alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, Si(R 11 ) 2 R 12 , OR 8 ,
  • phenyl, phenoxy, phenyl-Ci-C4-alkyl where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R 7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C6-cycloal
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloal
  • phenyl, phenyl-Ci-C-4-alkyl where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, C
  • phenyl, phenyl-Ci-C-4-alkyl where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ;
  • R 9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl,
  • phenyl benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ; and
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, R 9a and R 9b are together a C2-C7 alkylene-chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci
  • R 10 independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF 5 , Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF 5 , OH, CN, NO2, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6
  • Cs-Cs-cycloalkyl which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF 5 , OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
  • R 10 on adjacent carbon ring atoms may also be a bivalent radical selected from
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 2 , SCN, SF 5 , OH, d-C 6 -alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 2 , SCN, SF 5 , OH, Ci-C 6 -alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-al
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-Cs-cycloalkoxy, C3-Cs-cycloalkyl-Ci- C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or
  • R 17a , R 17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
  • R 17a and R 17b may together be a C2-C6 alkylene chain forming a 3- to 7-membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R 17a and R 17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur and nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
  • R 17c independently of its occurrence, is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , N0 2 , SCN , SF 5 , OH , Ci-C 6 -alkyl, C3-C6-cycloalkyl, Ci-C6-haloalky
  • R 18a , R 18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four
  • radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or,
  • R 18a and R 18b are together a C2-C7-alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloal
  • Y is a radical Y 1 , Y 2 , Y 3 , Y 4 or Y 5 , where
  • R 10 and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R 7 , or
  • R 3a is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R 10 ,
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 1 is Ci-C4-alkandiyl or C2-C4-alkendiyl
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 2 is Ci-C4-alkandiyl or C2-C4-alkendiyl
  • R 4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
  • each of the three aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • Cyc 3 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 3 is Ci-C4-alkandiyl or C2-C4-alkendiyl
  • R 4 and R 5a may also form a bivalent radical, selected from the group consisting of C2-C6-alkandiyl and C2-C6-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7b ;
  • R 5a if present, is selected from the group consisting of hydrogen, OH, CN, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3- C8-cycloalkyl-Ci-C4-alkoxy, wherein each of the 10 last mentioned radicals
  • phenyl and phenyl-Ci-C4-alkyl where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ;
  • R 5b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
  • Cyc 4 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 4 is Ci-C4-alkandiyl or C2-C4-alkendiyl; or
  • R 5a and R 5b may also form a bivalent radical, selected from the group consisting of C2-C6-alkandiyl and C2-C6-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7b ; where, independently of their occurrence, n is 0, 1 or 2; is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF 5 , Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R 7 ,
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • phenyl, phenoxy, phenyl-Ci-C4-alkyl where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R 7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halo
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocyclo
  • phenyl phenyl-Ci-C- 4 -alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl, C 3 -C 8 - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalky
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ;
  • R 9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 - C 8 -cycloalkyl-Ci-C 4 -alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6 haloalkynyl,
  • phenyl benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ; and
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 9b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkyny
  • Cs-Cs-cycloalkyI which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF 5 , OH, CN , NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- Ce-alkyhamino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN , NO2, SCN, SF 5 , OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbon
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF 5 , OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbony
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted
  • R 17a and R 17b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R 17a and R 17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci- C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
  • R 17c independently of its occurrence, is selected from the group consisting of hydrogen, CN , d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-
  • C4-alkyl wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , NO2, SCN , SF 5 , OH , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 18a and R 18b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 halo
  • the present invention relates to compounds of the formula (I), the stereoisomers, tautomers and the salts therof, wherein R 16 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R 7 ,
  • the present invention relates to and includes the following embodiments: agricultural and veterinary compositions comprising an amount of at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;
  • a method for protecting growing plants from attack or infestation by invertebrate pests comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof, in particular a method protecting crop plants from attack or infestation by animal pests, which comprises contacting the crop plants with a pesticidally effective amount of at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • a method for the protection of plant propagation, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • seeds comprising a compound of the formula (I) or an enantiomer, diastereomer or salt thereof;
  • a method for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;
  • a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises formulating a compound of formula (I) or a stereoisomer, tautomer and/or veterinary acceptable salt thereof with a carrier composition suitable for veterinary use; the use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
  • the present invention also relates to plant propagation materials, in particular as mentioned above to seeds, containing at least one compound of formula (I), a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof.
  • the present invention relates to each isomer alone, or mixtures or combinations of the isomers in any proportion to each other.
  • the compounds of the formula (I) may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • One center of chirality is the carbon ring atom carrying radical R 1 .
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure
  • the present invention also relates to potential tautomers of the compounds of formula (I) and also to the salts of such tautomers.
  • the present invention relates to the tautomer as such as well as to mixtures or combinations of the tautomers in any proportion to each other.
  • the term "tautomers” encompasses isomers, which are derived from the compounds of formula (I) by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
  • the compounds of the present invention i.e. the compounds of formula (I), their stereoisomers, their tautomers as well as their salts, in particular their agriculturally acceptable salts and their veterinarily acceptable salts, may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective
  • Salts of the compounds of the formula (I) are preferably agriculturally salts as well as veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or anions, in particular the acid addition salts of those acids, whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci- C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci- C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix C n - Cm indicates in each case the possible number of carbon atoms in the group.
  • Halogen will be taken to mean fluoro, chloro, bromo and iodo.
  • halogenated will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine.
  • partially or completely halogenated alkyl is also termed haloalkyl
  • partially or completely halogenated cycloalkyl is also termed halocycloalkyl
  • partially or completely halogenated alkylenyl is also termed haloalkenyl
  • partially or completely halogenated alkylynyl is also termed haloalkynyl
  • partially or completely halogenated alkoxy is also termed haloalkoxy
  • partially or completely halogenated alkylthio is also termed haloalkthio
  • partially or completely halogenated alkylsulfinyl is also termed haloalkylsulfinyl
  • partially or completely halogenated alkylsulfonyl is also termed haloalsulfonyl
  • partially or completely halogenated cycloalkylalkylalkyl is also termed halocycloalkylalkyl.
  • C n -C m -alkyl refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g.
  • 1 to 10 carbon atoms preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl,
  • Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
  • C n -C m -haloalkyl refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g.
  • Ci-C4-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 - bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl,
  • Ci-C4-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloroflu
  • Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.
  • fluoromethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms.
  • Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • C n -C m -haloalkoxy refers to straight-chain or branched alkyl groups having n to m carbon atoms, e.g.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C4-Alkoxy is, for example, methoxy, ethoxy, n- propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy).
  • Ci-C6-Alkoxy includes the meanings given for Ci-C4-alkoxy and also includes, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy.
  • Ci-Cs-Alkoxy includes the meanings given for Ci-C6-alkoxy and also includes, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy includes the meanings given for Ci- Ce-alkoxy and also includes, for example, nonyloxy, decyloxy and positional isomers thereof.
  • C n -C m -alkylthio is a C n -C m -alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C4-Alkylthio is, for example, methylthio, ethylthio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec- butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
  • C1-C6- Alkylthio includes the meanings given for Ci-C4-alkylthio and also includes, for example, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
  • d-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio includes the meanings given for d-Cs-alkylthio and also includes, for example, nonylthio, decylthio and positional isomers thereof.
  • C n -C m -alkylsulfinyl is a C n -C m -alkyl group, as defined above, attached via a
  • C n -C m -haloalkyloxy is a C n -C m -haloalkyl group, as defined above, attached via an oxygen atom.
  • Examples include Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 - bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro- 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and penta
  • C n -C m -haloalkylthio is a C n -C m -haloalkyl group, as defined above, attached via a sulfur atom.
  • Examples include Ci-C2-haloalkylthio, such as chloromethylthio,
  • Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively.
  • 1 - pentenyl 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl- 4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-
  • C2-C m -haloalkenyl refers to C2-C m -alkenyl, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example 1 -fluoroethenyl, 2-fluoroethenyl, 2,2- difluoroethenyl, 1 ,2,2-trifluoroethenyl, 1 -fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2- propenyl, 1 -fluoro-1 -propenyl, 1 ,2-difluoro-1 -propenyl, 3,3-difluoropropen-2-yl, 1 -chloroethenyl, 2-chloroethenyl,
  • C2-C m -alkynyl refers to a linear or branched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
  • C2-C m -haloalkynyl as used herein, which is also expressed as “C2-C m -alkynyl which is partially or completely halogenated”, refers to C2-C m -alkynyl, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • Examples of C2-C m -haloalkynyl include 1 -fluoro-2- propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 1 -fluoro-2-propynyl and 1 ,1 -difluoro-2- propenyl, and the like.
  • C3-C m -cycloalkyl refers to a monocyclic and polycyclic 3- to m- membered saturated cycloaliphatic radical, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1 ]octyl.
  • cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • C3-C m -cycloalkenyl refers to a monocyclic and polycyclic 3- to m-membered unsaturated cycloaliphatic radical, e.g. cyclopropenyl, cyclobutenyl,
  • cyclopentenyl denotes a monocyclic unsaturated hydrocarbon radical.
  • C3-C m -halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or completely halogenated”, refers to C3-C m -cycloalkyl as mentioned above, in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
  • C3-C m -halocycloalkyl examples include 1 - fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1 -chlorocyclcopropyl, 2- chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl, 1 -fluorocycobutyl etc.
  • C3-C m -cycloalkyl-Ci-C4-alkyl refers to a C3-C m -cycloalkyl group as defined above, which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • C3-C m -cycloalkyl-Ci-C4-alkyl examples include cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
  • C3-C m -halocycloalkyl-Ci-C4-alkyl refers to a C3-C m -halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group.
  • Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert- butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 -isopropoxyethyl, 1 -n- butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert-butoxyethyl, 2-methoxyethyl, 2- ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 - is
  • Ci-C4-haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms, either in the alkoxy moiety or in the alkyl moiety or in both, are replaced by halogen atoms.
  • Examples are difluoromethoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.
  • C n -C m -alkoxycarbonyl is a C n -C m -alkoxy group, as defined above, attached via an carbonyl group atom.
  • Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl.
  • C1-C4- Alkoxy is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1 - methylethoxycarbonyl, butoxycarbonyl, 1 -methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 ,1 -dimethylethoxycarbonyl.
  • Ci-C6-Alkoxycarbonyl includes the meanings given for C1-C4- alkoxycarbonyl and also includes, for example, pentoxycarbonyl, 1 -methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1 ,1 -dimethylpropoxycarbonyl, 1 ,2- dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -ethylpropoxycarbonyl,
  • aryl refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
  • 3- to 6-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings.
  • 3- to 7-membered carbocyclic ring refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane rings.
  • heterocyclic ring containing 1 , 2 or 3 heteroatoms or “containing heteroatom groups", wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic.
  • the heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
  • Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic rings include: oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3
  • Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-d ihyd rofur-3-yl , 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2- yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-y
  • Examples of 5- or 6-membered aromatic heterocyclic rings also termed heteroaromatic rings, heteroaryl or hetaryl, include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3- pyrazolyl, 4-pyrazo-"lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5- thiazo-"lyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
  • a "Ci-Cm-alkylene” is divalent branched or preferably non-branched or linear saturated aliphatic chain having 1 to m, e.g. 1 to 7 carbon atoms, for example Chb, CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH 3 )CH 2 , CH 2 CH(CH 3 ), CH2CH2CH2CH2, CH2CH2CH2CH2CH2,
  • Embodiments of the present invention as well preferred compounds of the present invention are outlined in the following paragraphs.
  • the remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents Het, Y, R 1 , R 2 , R 3a , R 3b , including the variables X, R 4 , R 5a , R 5b , as well as R 6 and the variable k are valid both on their own and, in particular, in every possible combination with each other.
  • Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond in formula (I), and wherein R 6 and k are as defined above and where R 6a is hydrogen or has one of the meanings given for R 6 and where R 6b is hydrogen or a C-bound radical mentioned as R 6 and where R 6b is in particular hydrogen, Ci-C4-alkyl or C1-C4- haloalkyl.
  • k is 0, 1 or 2, especially 0 or 1 .
  • k is especially 1.
  • R 6a in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen.
  • R 6 is preferably selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four last mentioned radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may be (further) substituted independently from one another with one or more (e.g.
  • R 6 is in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,
  • halogen such as chlorine or fluorine
  • C1-C4- alkyl such as methyl or ethyl
  • Ci-C4-alkoxy such as methoxy or ethoxy
  • Ci-C4-haloalkoxy such as difluoromethoxy or trifluoromethoxy
  • Ci-C4-haloalkyl such as difluoromethyl
  • R 6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, C1-C4- alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-
  • R 6b is in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
  • Ci-C4-alkyl such as methyl or ethyl
  • Ci-C4-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethy
  • Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24,
  • R 6 is selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroe
  • R 6a is selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and C1-C4- haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci- C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoro
  • k 0, 1 or 2.
  • a particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 , where k is 0, 1 or 2, in particular 1 or 2 and especially 1 and where R 6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,
  • halogen such as chlorine or fluorine
  • C1-C4- alkyl such as methyl or ethyl
  • Ci-C4-alkoxy such as methoxy or ethoxy
  • Ci-C4-haloalkoxy such as difluo
  • a particular sub-group of embodiments relates to compounds of the formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 a
  • R 6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl;
  • halogen such as chlorine or fluorine
  • Ci-C4-alkyl such as methyl or ethyl
  • Ci-C4-haloalkyl such as difluoromethyl, trifluoro
  • R 6a is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine and Ci-C4-alkyl, such as methyl or ethyl, more preferably is hydrogen.
  • a special embodiment of the radical Het-1 a is 6-chloropyridin-3-yl, i.e. R 6a is hydrogen and R 6 is chlorine.
  • a further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3- yl, i.e. R 6a is hydrogen and R 6 is trifluoromethyl.
  • Another particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 1 , where k is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-1 1 a,
  • R 6a is as defined above and wherein R 6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and C1-C4- haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluor
  • Het is a radical of formula Het-24, where k is 0, 1 or 2, in particular 0 or 1 , and where R 6 , if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoro
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl.
  • Ci-C6-alkyl in particular Ci-C4
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
  • R 1 and R 2 are independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
  • At least one of the radicals R 1 and R 2 is hydrogen.
  • R 1 and R 2 are both hydrogen.
  • a group of embodiments relates to compounds of formula (I), wherein R 3a is different from hydrogen.
  • Another group of embodiments relates to compounds of formula (I), wherein R 3a is hydrogen.
  • R 3a is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 1 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH 2 CH 2 or CHCH 3 .
  • variable R 10 is in particular selected from the group consisting of halogen, N0 2 , CN, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -alkylsulfinyl and Ci- C 4 -alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely
  • halogenated and especially selected from the group consisting of halogen, such as fluorine or chlorine, N0 2 , CN and Ci-C 4 -alkoxy, such as methoxy or ethoxy.
  • the variable Cyc 1 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridinyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R 10 , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogen, such as fluorine
  • Cyc 1 is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
  • halogen such as fluorine, chlorine or bromine
  • R 3a is Ci-C6-alkyl or Ci-C6-haloalkyl, in particular Ci-C3-alkyl or C1-C3- haloalkyl, where alkyl and haloalkyl may further carry any combination of 1 , 2 or 3 radicals R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl.
  • R 3a is selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2.
  • R 7a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • R 8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
  • phenylaminocarbonyl wherein the phenyl ring in the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2,
  • R 8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • R 9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • radical R 10 is in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
  • R 3b is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 2 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH2CH2 or CHCH 3 .
  • variable R 10 is in particular selected from the group consisting of halogen, N0 2 , CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci- C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely
  • halogenated and especially selected from the group consisting of halogen, such as fluorine or chlorine, N0 2 , CN and Ci-C4-alkoxy, such as methoxy or ethoxy.
  • variable Cyc 2 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridinyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R 10 , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 2 , CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N0 2 , CN and Ci-C4-alkoxy.
  • halogen such as fluorine, chlorine or bromine
  • N0 2 , CN Ci-C4-alkoxy
  • Cyc 2 is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R 10 , as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N0 2 , CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
  • halogen such as fluorine, chlorine or bromine
  • R 3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyi may carry 1 , 2 or 3 further radicals R 7 , which are identical or different.
  • R 3b is selected from the group consisting of Ci-C3-alkyl and C1-C3- haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and
  • the group Y in formula (I) is a group Y 1 , where X is in particular O and where R 4 is as defined herein.
  • the group Y in formula (I) is a group Y 2 , where X is in particular O and where R 4 is as defined herein.
  • the group Y in formula (I) is a group Y 3 , where X is in particular O and where R 4 and R 5a as defined herein.
  • the group Y in formula (I) is a group Y 4 , where R 5a and R 5b as defined herein.
  • the group Y in formula (I) is a group Y 4 , where R 5a and R 5b as defined herein.
  • the radical X in the groups Y 1 , Y 2 and Y 3 in the groups (1 ), (2) and (3) embodiments is in particular O.
  • radical R 4 is in particular selected from the group consisting of
  • Ci-C6-alkyl C2-C6-alkenyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • the radical R 4 is even more particularly selected from the group consisting of
  • Ci-C4-alkyl C2-C4-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 ,
  • heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized.
  • radical R 4 is even more particularly selected from the group consisting of
  • aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the aromatic heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 .
  • groups (1 ), (2) and (3) of embodiments relate to compounds of the formula (I), wherein the variable R 4 is C1-C6- alkyl, which is unsubstituted, partly or completely halogenated and/or may carry any
  • R 7 is as defined above and in particular selected from the group consisting of from CN, NO2, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, S(0) n R 8a and S(0) n NR 7a R 7b .
  • radicals R 4 examples include the following radicals R-4.1 to R-4.18:
  • groups (1 ), (2) and (3) of embodiments relate to compounds of the formula (I), wherein the variable R 4 is 6-membered heteroaryl, which is in particular selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, wherein 6-membered heteroaryl is unsubsituted or carries 1 , 2, 3 or 4 radicals R 10 , which are in particular selected from halogen, CN, N0 2 , Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
  • R 4 is 6-membered heteroaryl, which is in particular selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, wherein 6-membered heteroaryl is unsubsituted or carries 1 , 2, 3 or 4 radicals R 10 , which are in
  • R 4 examples include 2-thiazolyl (R-40.1 ) and 2-pyrazinyl (R-40.2).
  • A is CH 2 , CH 2 CH 2 or CH 2 CH 2 CH 2 ,
  • R 10aa is hydrogen or a radical R 10 as defined above, which R 10aa is in particular selected from hydrogen, halogen, especially fluorine, S(0) n R 16a , CN and N0 2 , where n is 0, 1 or 2 and R 16a is as defined above an in particular selected from Ci-C4-alkyl and Ci- C4-haloalkyl.
  • radicals R-41 and R-42 include the following radicals R-41.1 to R-41.20 and
  • R-41.1 cyclopropyl
  • R-41.2 cyclobutyl
  • R-41.3 1 -fluorocyclopropyl
  • R-41.4 1 -fluorocyclobutyl
  • R-41.5 1 -cyanocyclopropyl
  • R-41.6 1 -cyanocylobutyl
  • R-41 7 -nitrocyclopropyl
  • R-41 8 -nitrocyclobutyl
  • R-41 9 -(methylthio)cyclopropyl
  • R-41 10 -(methylsulfinyl)cyclopropyl
  • R-41 1 1 -(methylsulfonyl)cyclopropyl
  • R-41 12 (ethylthio)cyclopropyl
  • R-41 13 -(ethylsulfinyl)cyclopropyl
  • R-41 14 -(ethylsulfonyl)cyclopropyl
  • R-41 15 -(methylthio)cyclobutyl
  • RR--4411.1166 1 -(methylsulfinyl)cyclobutyl
  • R-41 17 -(methylsulfonyl)cyclobutyl
  • R-41 18 -(ethylthio)cyclobutyl
  • R-41 19 -(ethylsulfinyl)cyclobutyl
  • R-41 20 -(ethylsulfonyl)cyclobutyl
  • R-42 2 2-oxetanyl
  • R-42 3 2-fluoro-2-oxiranyl
  • R-42 4 2-fluoro-2-oxetanyl
  • R-42 5 2-cyano-2-oxiranyl
  • R-42 7 2-nitro-2-oxiranyl
  • R-42 8 2-nitro-2-oxetanyl.
  • R x is hydrogen, halogen, CN, N0 2 , CrC 4 -alkyl, Ci-C 4 -haloalkyl, NR 17a R 17b ,
  • S(0) 2 NR 17a R 17b , S(0) 2 R 8a or C( 0)OR 8 and in particular hydrogen, CN, Ci-C 4 -alkyl, such as methyl, or Ci-C 4 -haloalkyl, such as trifluoromethyl;
  • R 16 is especially selected from the group consisting of hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, where the two aforementioned radicals may carry 1 or 2 radicals R 7 , which are selected from the group consisting of NO2, CN and OR 8 , C2-C4-alkenyl, C2-C4- haloalkenyl, and benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 - alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amin
  • radicals R-43 are the radicals R-43.1 to R-43.44, where R x and R 16 are as defined in the rows of the following table A:
  • groups (1 ), (2) and (3) of embodiments further particular groups (1 e), (2e) and (3e) of embodiments relate to compounds of the formula (I), wherein the variable R 4 is a radical of formula NR 18a R 18b .
  • radicals R 18a and R 18b are each independently from one another preferably selected from the group consisting of
  • Ci-C6-alkyl in particular Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl or isobutyl, wherein the aforementioned alkyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 , especially 1 radical R 7
  • C3-Cio-cycloalkyl which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10
  • C3-C6-cycloalkyl which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ;
  • Ci-C4-alkoxy such as methoxy, ethoxy, n-propoxy and isopropoxy
  • Ci-C4-haloalkoxy in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
  • Ci-C4-alkylcarbonyl such as acetyl or propionyl
  • Ci-C4-haloalkylcarbonyl such as difluoroacetyl or trifluoroacetyl
  • Ci-C4-alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert- butoxycarbonyl,
  • Ci-C4-alkylaminocarbonyl such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl,
  • Ci-C4-alkylsulfonyl such as methylsulfonyl or ethylsulfonyl
  • Ci-C4-haloalkylsulfonyl such as trifluoromethylsulfonyl
  • Ci-C4-alkylaminosulfonyl such as methylaminosulfonyl or ethylaminosulfonyl, di-(Ci-C4-alkyl)aminosulfonyl, such as dimethylaminosulfonyl or diethylaminosulfonyl; phenyl, which is unsubstituted or carries 1 , 2 3 or 4 radicals R 10 ,
  • phenoxy which is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 2 , SCN, SF 5 , OH, Ci-C 6 -alkyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci- C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
  • heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R 10 .
  • radicals R 10 where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1 , 2, 3, 4 or 5 radicals R 10 .
  • radical R 10 is as defined herein and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy,
  • R 18a and R 18b may also together be a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7- membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,
  • Ci-C6-alkylthio in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
  • Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
  • fluoromethylsulfanyl difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
  • R 18a is selected from the group consisting of hydrogen and Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and especially hydrogen, while R 18b has one of the above given meanings and where R 18b is in particular
  • Ci-C6-alkyl in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
  • each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 , which is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl; or
  • R 18b is Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
  • Ci-C4-alkylcarbonyl such as acetyl or propionyl
  • Ci-C4-haloalkylcarbonyl such as difluoroacetyl or trifluoroacetyl
  • Ci-C4-alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl
  • Ci-C4-alkylaminocarbonyl such as methylaminocarbonyl or
  • ethylaminocarbonyl di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl,
  • diethylaminocarbonyl N-methyl-N-ethylaminocarbonyl, NH2-S(0)2, Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylsulfonyl, such as trifluoromethylsulfonyl, C1-C4- alkylaminosulfonyl, such as methylaminosulfonyl or ethylaminosulfonyl, di-(Ci-C4- alkyl)aminosulfonyl, such as dimethylaminosulfonyl or diethylaminosulfonyl;
  • R 18a and R 18b may also together be a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7- membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,
  • Ci-C6-alkylthio in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
  • Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
  • fluoromethylsulfanyl difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
  • R 18a is selected from the group consisting of hydrogen and Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and especially hydrogen, while R 18b is in particular
  • Ci-C6-alkyl in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
  • each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 , which is as defined above and in particular selected from the group consisting of CN , OH, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl;
  • R 18a and R 18b may also together be a C2-C6 alkylene chain and form a 3-, 4-, 5-, 6- or 7-membered saturated ring together with the nitrogen atom they are bonded to.
  • radicals NR 18a NR 18b include the following radicals R-44.1 to R-44.10
  • R-44.10 1 -aziridinyl.
  • groups (1 ), (2) and (3) of embodiments relate to compounds of the formula (I), wherein the variable R 4 is O-R 8 , wherein R 8 is as defined above and in particular selected from the group consisting of
  • Ci-C6-alkyl in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
  • each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R 7 , which is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl; or
  • - C3-C6-cycloalkyl which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , which are as defined above and preferably selected from the group consisting of halogen, such as fluorine or chlorine, CN, OH , Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methyls
  • radicals OR 8 examples include the following radicals R-45.1 to R-45.6
  • R-45.4 isopropoxy
  • radical R 7 is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or
  • C 3 -C 6 -cycloalkyl such as cyclopropyl or cyclobutyl
  • radical R 7a is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)eth
  • radical R 8 is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-
  • radical R 8a is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 - (trifluoromethyl)ethyl
  • radicals R 9a and R 9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are as defined herein or preferably selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, C1-C4- halo
  • NR 9a R 9b may preferably also be a saturated N-bound 3-, 4-, 5- or 6- membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6- membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from C1-C4- alkyl and Ci-C4-haloalkyl.
  • radicals NR 9a R 9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, N-methyl-N- ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N-methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1 -pyrrolidinyl, 1 - piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4-morpholinyl.
  • radical R 10 is as defined herein and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci- C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -d
  • fluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, SO2NH2, C1-C4- alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4- alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N- ethylaminocarbonyl and the like.
  • radical R 15 is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2, 2-difluoro-1 -methylethyl, 2, 2, 2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)ethy
  • fluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino,
  • the radical R 16 is in particular selected from the group consisting of Ci-C4-alkyl,C2-C4-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated, and benzyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl
  • fluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino, diethylamino, N-methyl-N-ethylamino, (Ci-C4-alkyl)carbonyl, such as acetyl or propionyl, (C1-C4- alkyl)carbonyloxy, such as acetoxy or propionoxy, and (Ci-C4-alkoxy)carbonyl such as methoxy
  • radicals R 17a and R 17b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, phenyl or benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2, 3 or 4 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl,
  • Ci-C4-alkylthio such as methylthio or ethylthio, C1-C4- alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylthio, such as
  • fluoromethylsulfonyl difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino,
  • variable n irrespectively of its occurrence, is in particular 0 or 2.
  • R 7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-
  • R 8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
  • phenylaminocarbonyl wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N0 2 , SCN, SF 5 , OH, Ci-C 6 - alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; R
  • R 10 is selected from the group consisting of halogen, CN, OH , SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl
  • R 15 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2 3 or 4 radicals selected from halogen, OH, CN, N0 2 , d-Ce-alkyl, Ci-C 6 -haloalkyl, d-C 6 -alkoxy, Ci-C 6 haloalkoxy, (Ci-C 6 - alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl;
  • R 17a , R 17b are each independently from one another selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substitutents is unsubstituted or carries 1 , 2 3 or 4 radicals selected from halogen, OH , CN, N0 2 , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 haloalkoxy, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl.
  • R 7a is selected from the group consisting of Ci-C4-alkyl or Ci-C4-haloalkyl;
  • R 8 is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;
  • R 8a is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;
  • R 9a is selected from the group consisting of hydrogen and Ci-C4-alkyl
  • R 9b is selected from the group consisting of hydrogen and Ci-C4-alkyl
  • R 10 is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, C1-C4- haloalkylthio and Ci-C4-haloalkylsulfonyl;
  • R 15 is selected from the group consisting of hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl
  • R 16a is selected from the group consisting of Ci-C4-alkyl, which is unsubstituted, partly or completely halogenated
  • R 17a , R 17b are each independently from one another selected from the group consisting of hydrogen and Ci-C4-alkyl.
  • R 5a is as defined above and preferably selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C2-C6-alkenyl, in particular C2-C4-alkyl, such as 2- propenyl, Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, Cs-Cs-cycloalkyl, such as cyclopropyl, cyclopbutyl, cyclopentyl or cyclohexyl, C3- C8-cycloalkyl-Ci-C4-alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alky
  • phenyl and phenyl-Ci-C4-alkyl in particular phenyl and benzyl, where the phenyl ring in the last four mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 .
  • R 5b is in particular selected from the group consisting of Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C2-C6-alkenyl, in particular C2-C4-alkyl, such as 2-propenyl, Cs-Cs-cycloalkyl, such as cyclopropyl, cyclopbutyl, cyclopentyl or cyclohexyl, C3-C8-cycloalkyl-Ci-C4-alkyl, in particular C3- C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutyl methyl, wherein alkyl, alkenyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
  • phenyl and phenyl-Ci-C4-alkyl where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , where the radical R 10 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and iso
  • R 5a is in particular selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, C3-C8-cycloalkyl-Ci-C4-alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alkyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
  • R 5a is especially selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl and Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy.
  • R 5a is especially hydrogen, OH, methyl or methoxy.
  • radical R 7a is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)e
  • radical R 8 is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 - (trifluoromethyl)ethy
  • Ci-C6-alkylthio in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
  • Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
  • fluoromethylsulfanyl difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
  • Ci-C6-alkylthio in particular Ci-C 4 -alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
  • Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
  • fluoromethylsulfanyl difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
  • radical R 4 is a radical as defined in groups (1 a), (1 b), (1 c), (1 d), (1 e) and (1f) embodiments;
  • radical R 4 is a radical as defined in groups (3a), (3b), (3c), (3d), (3e) and (3f) embodiments;
  • R 5a is in particular selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C6-alkoxy, in particular Ci-C 4 -alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, C3-C8- cycloalkyl-Ci-C 4 -alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alkyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
  • R 5a is more particularly selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl and Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy; and where R 5a is especially hydrogen, OH, methyl or methoxy. and where X is O.
  • Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
  • X is preferably O
  • R 1 and R 2 are independently from each other selected from the group consisting of
  • Ci-C6-alkyl in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl,
  • R 3a is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
  • heteroatoms as ring members which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 1 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH 2 CH 2 or CHCH 3 ;
  • R 3b is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 , C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
  • heteroatoms as ring members which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 2 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH 2 CH 2 or CHCH 3 .
  • Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
  • X is preferably O
  • R 1 and R 2 are independently from each other selected from the group consisting of
  • Ci-C3-alkyl such as methyl ethyl or isopropyl, or C1-C3- haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R 1 and R 2 are both hydrogen or R 1 is methyl and R 2 is hydrogen;
  • R 3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
  • halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C 4 -alkyl.
  • R 3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R 7 , which are identical or different.
  • X is preferably O
  • R 1 and R 2 are both hydrogen or R 1 is methyl and R 2 is hydrogen;
  • R 3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where R 7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
  • R 3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl,
  • R 3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
  • Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
  • X is preferably O
  • R 1 and R 2 are independently from each other selected from the group consisting of
  • Ci-C6-alkyl in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl,
  • R 3a is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH 2 , CH2CH2 or CHCH3; and
  • R 3b is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
  • heteroatoms as ring members which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • Q 2 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH2CH2 or CHCH 3 .
  • Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
  • X is preferably O
  • R 1 and R 2 are independently from each other selected from the group consisting of
  • Ci-C3-alkyl such as methyl ethyl or isopropyl, or C1-C3- haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R 1 and R 2 are both hydrogen or R 1 is methyl and R 2 is hydrogen;
  • R 3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
  • halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C 4 -alkyl.
  • R 3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R 7 , which are identical or different.
  • the radicals R 7 are as defined above and in particular from the group consisting of
  • N0 2 , CN, Cs-Ce-cycloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, N-0-Ci-C 4 -alkyl, C1-C4- alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R 7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.
  • Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
  • X is preferably O
  • R 1 and R 2 are both hydrogen or R 1 is methyl and R 2 is hydrogen;
  • R 3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where R 7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
  • R 3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH 2 CN, CH2CH2CN, CH2NO2 and CH2CH2NO2;
  • R 3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
  • R 6 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluormethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as
  • difluoromethyl trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
  • R 7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or
  • trifluormethoxy such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C3- C6-cycloalkyl such as cyclopropyl, cyclobutyl or cyclopropyl, and C3-C6-halocycloalkyl.
  • R 7a irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethy
  • R 8 irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or
  • R 8a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are preferably selected, independently of each other from halogen, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkyl.
  • R 9a and R 9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 9a R 9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 9a R 9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
  • R 10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluor
  • R 11 , R 12 independently of their occurrence, are selected from the group consisting of Ci-
  • R 13 , R 14 independently of their occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, and phenyl.
  • R 15 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethy
  • R 16a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl
  • R 17 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN , Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl
  • R 17a and R 17b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR 17a R 17b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C
  • radicals NR 17a R 17b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
  • R 17c irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroeth
  • X is O or S, especially O;
  • R 1 is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3- C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular C1-C2- haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 - fluorocyclopropyl or 2,2-difluorocyclopropyl,
  • Ci-C3-alkyl such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl,;
  • R 3a is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , Q 1 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH 2 CH 2 or CHCH 3 ; R 3b is a C-bound radical, in particular
  • Ci-C6-alkyl which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 ,
  • C3-C6-cycloalkyl which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R 10 , or
  • Cyc 2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , and
  • Q 2 is Ci-C 4 -alkanediyl or C 2 -C 4 -alkenediyl, in particular CH 2 , CH 2 CH 2 or CHCH 3 ;
  • R 4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
  • R 5a if present, is selected from H, Ci-C 4 -alkyl, OH and Ci-C 4 -alkoxy.
  • X is O or S, especially O;
  • R 1 is selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl;
  • R 3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
  • halogenated and/or carries any combination of 1 , 2 or 3 radicals R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl.
  • R 3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R 7 , which are identical or different.
  • R 4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
  • R 5a if present, is selected from H , Ci-C4-alkyl, OH and Ci-C4-alkoxy.
  • X is O or S, especially O;
  • R 1 is hydrogen or methyl and especially hydrogen
  • R 3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R 7 , or C3-C6-cycloalkyl, especially cyclopropyl, where R 7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
  • R 3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH 2 CN, CH2CH2CN, CH2NO2 and CH 2 CH 2 N0 2 ;
  • R 3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
  • R 4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
  • R 5a if present, is selected from H , Ci-C4-alkyl, OH and Ci-C4-alkoxy.
  • I-B.2 I-C.2 A special group of embodiments relates to the compounds of formula (I-A.1 ), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-A.2), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-B.1 ), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-C.1 ), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-A.3), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, R 5a is H, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-A.4), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, R 5a is H, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-B.2), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, R 5a is H, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.
  • a further special group of embodiments relates to the compounds of formula (I-C.2), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen, R 5a is H, X is O, and where R 3a , R 3b and R 4 are as defined in lines 1 to 972 of the following table B.

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Abstract

The present invention relates to N-substituted imino compound formula (l):wherein The invention also relates to the use of the N-acylimino heterocyclic compounds, their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such compounds.

Description

N-acylamidine compounds
The present invention relates to Ν,Ν'-substituted amidinecompounds of the formula (I) as defined herein, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds. The invention also relates to the use of the N,N'-substituted amidinecompounds of the formula (I), their stereoisomers, their tautomers and their salts, for combating invertebrate pests. Furthermore the invention relates also to methods of combating invertebrate pests, which comprises applying such Ν,Ν'-substituted amidinecompounds. Background of Invention
Invertebrate pests, such as insects, acaridae and nematode pests destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating animal pests. In particular, animal pests such as insects and acaridae are difficult to be effectively controlled.
WO 91/04965 describes insecticidall active amidine compounds of the formula A,
Figure imgf000002_0001
alkylidene, R2 is, inter alia, hydrogen, alkyl, carbamoyl, R3 is, inter alia, optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl, Z represents N or CH and R4 is cyano or nitro.
EP 376 279 describes insecticidally active guanidine derivatives of the formula B
Figure imgf000002_0002
WO 2008/009360 describes compounds of formula A similar to those of WO 91/04965, wherein Ri is aryl, heteroaryl or heterocyclyl, Z is N , F¾ is halogenated alkyl, alkenyl or cycloalkyl, R3 is alkyl or cycloalkyl, R4 is CN.
WO 97/01537 describes N-methylene thiourea derivatives of the formula C
Het-
Figure imgf000003_0001
(C)
wherein Het is a heterocyclic radical, n is 0, 1 or 2, Ri is hydrogen or alkyl and R2 is hydrogen, alkyl, a primary, secondary or tertiary amino group, alkoxy or thioalkyl.
K. Ford et al., J. Agricultural and Food Chemistry describe N'-(aminocarbonyl)-N-[(6- chloro-3-pyridyl)methyl]-N-methyl ethanimidamide as a metabolite of N'-cyano-N-[(6-chloro-3- pyridyl)methyl]-N-methyl ethanimidamide (common name acetamiprid).
The pesticidal activity of the compounds is not satisfactory. It is therefore an object of the present invention to provide compounds having a good pesticidal activity, especially against difficult to control insects and acarid pests.
Summary of Invention
It has been found that these objects are solved by Ν,Ν'-substituted amidinecompounds of the general formula (I) described below, by their stereoisomers, their tautomers and their salts. Therefore, the present invention relates to Ν,Ν'-substituted amidinecompounds of formula (I):
Figure imgf000003_0002
wherein is a radical Y1, Y2, Y3, Y4 or Y5, where is 0-C(=X)-R4;
is S-C(=X)-R4;
is N(R5a)-C(=X)-R4;
is N(R5a)-S(=0)-R5b; Y5 is N(R5a)-S(=0)2-R5b; and where X is O or S; Het is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen and nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R6, wherein k is an integer selected from 0, 1 , 2, 3 or 4;
R1, R2 are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
Si(R11)2R12, OR8, OS02R8a, S(0)nR8a, S(0)nNR9aR9b, NR9aR9b, C(=0)NR9aR9b,
C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a, phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 form, together with the carbon atom, which they attached to, a 3-,
4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R7, or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9 ; R3a is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10,
NR9aR9b, C(=0)NR9aR9b, C(=S)NR9aR9b, OR8, S(0)nR8a, C(=0)OR8, C(=0)R7a, C(=S)R7a, Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q1 is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10,
OR8, S(0)nR8a, C(=N-0-R16a)R15, Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl; is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, S(0)nR8a, S(0)nNR9aR9b, NR18aR18b, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)OR8, C(=0)R7a, C(=S)R7a, and
Cyc3-Q3, where Cyc3 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,and where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
Q3 is a single bond, Ci-C4-alkanediyl or C2-C4-alkenediyl;
R4 and R5a, if present, together may also form a bivalent radical, selected from the group
consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the two aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b;
R5a if present, is selected from the group consisting of hydrogen, OH, CN, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, Ci-C6-alkoxy, C2-C6- alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8-cycloalkyl-Ci-C4-alkoxy, wherein each of the 10 last mentioned radicals are unsubstituted, partly or completely
halogenated,
C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10;
R5b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, NR9aR9 , C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)OR8, C(=0)R7a, C(=S)R7a, Cyc4-Q4, where
Cyc4 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q4 is Ci-C4-alkanediyl or C2-C4-alkenediyl; or R5a and R5b, if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the two aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b; where, independently of their occurrence, n is 0, 1 or 2;
R6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, C1-C10- alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R7, OR8, NR17aR17b, S(0)nR8a, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7 , C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7 , C(=S)OR8, C(=S)SR8a, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R6 together form a linear C2-C7-alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10;
R7 independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF5, Ci-C6-alkyl, d-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2- Ce-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Si(R11)2R12, OR8,
OS02R8a, S(0)nR8a, S(0)nNR 7aR 7 , NR17aR17b, C(=0)NR 7aR 7 , C(=S)NR 7aR 7 , C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15, NR 7a-C(=0)R7a, NR 7a-C(=S)R7a, NR 7a- C(=0)OR8, NR 7a-C(=0)NR 7aR 7b,
phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17,
=NOR16 or =NNR9aR9b,
or two R7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C3- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, where the phenyl ring in the two last-mentioned radicals is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or two of R7b present on one carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C(=0)R15,
C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR16,
phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, Cs-Cs-halocycloalkyI, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10;
R9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl,
S(0)nR16, -S(0)nNR 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)NR 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)NR 7aR 7 , C(=NR 7)R15;
phenyl, benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10; and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, R9a and R9b are together a C2-C7 alkylene-chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R9a and R9b together may form =CR13R14, =NR17 or =NOR16 moiety;
R10 independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF5, OH, CN, NO2, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
Cs-Cs-cycloalkyl, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN, SF5, OH, CN, NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
Si(R11)2R12, OH, SH, OR16, OS(0)nR16a, -S(0)nR16a, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7 , C(=S)NR 7aR 7 , phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
two R10 present together on one carbon ring atom of a saturated or partly unsaturated
heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16, =NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from
CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH,
OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS,
CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N, SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy;
R11 , R12 independently of their occurrence, are selected from the group consisting of C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-
C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N02, SCN, SF5, OH, d-Ce-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R13, R14 independently of their occurrence, are selected from the group consisting of
hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and benzyl; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci- C4 alkoxy;
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, d-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R7,
phenyl, benzyl, 5- or 6-membered hetaryl or 5- or 6-membered hetaryl-methyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci- C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-Cs-cycloalkoxy, C3-Cs-cycloalkyl-Ci- C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
or,
R17a and R17b may together be a C2-C6 alkylene chain forming a 3- to 7-membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R17a and R17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur and nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
R17a and R17b together may form =CR13R14, =NR17 or =NOR16 moiety;
R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , N02, SCN , SF5, OH , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R18a, R18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four
aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
OR16, S(0)nR16a, -S(0)nN R 7aR 7b, C(=0)R15, C(=0)OR16, C(=0)N R 7aR 7b, C(=S)R15, C(=S)SR16a, C(=S)N R 7aR 7b, C(=N R 7)R15; phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or,
R18a and R18b are together a C2-C7-alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci- C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; the stereoisomers, tautomers and the salts thereof. In a special embodiment, the present invention relates to N,N'-substituted amidinecompounds of formula (I)
Figure imgf000015_0001
wherein
Y is a radical Y1 , Y2, Y3, Y4 or Y5, where
Y1 is 0-C(=X)-R4;
Y2 is S-C(=X)-R4;
Y3 is N(R5a)-C(=X)-R4;
Y4 is N(R5a)-S(=0)-R5b;
Y5 is N(R5a)-S(=0)2-R5b; and where X is O or S; is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen or nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R6, wherein k is an integer selected from 0, 1 , 2, 3 or 4; are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7
Si(R11)2R12, OR8, OS02R8a, S(0)nR8a, S(0)nNR9aR9b, NR9aR9b, C(=0)NR9aR9 , C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a, phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R7, or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9b;
R3a is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10,
NR9aR9b, C(=0)NR9aR9b, C(=S)NR9aR9b, OR8, S(0)nR8a, C(=0)OR8, C(=0)R7a, C(=S)R7a,
Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q1 is Ci-C4-alkandiyl or C2-C4-alkendiyl;
R3b is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10, OR8, S(0)nR8a, C(=N-0-R16a)R15,
Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkandiyl or C2-C4-alkendiyl;
R4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, S(0)nR8a, S(0)nNR9aR9b, NR18aR18b, C(=0)NR9aR9b, C(=S)NR aR b, C(=0)OR8, C(=0)R7a, C(=S)R7a, and
Cyc3-Q3, where
Cyc3 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q3 is Ci-C4-alkandiyl or C2-C4-alkendiyl;
R4 and R5a, if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkandiyl and C2-C6-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b; R5a if present, is selected from the group consisting of hydrogen, OH, CN, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3- C8-cycloalkyl-Ci-C4-alkoxy, wherein each of the 10 last mentioned radicals are unsubstituted, partly or completely halogenated,
C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10;
R5b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, NR9aR9b, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)OR8, C(=0)R7a, C(=S)R7a,
Cyc4-Q4, where
Cyc4 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q4 is Ci-C4-alkandiyl or C2-C4-alkendiyl; or
R5a and R5b, if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkandiyl and C2-C6-alkendiyl, wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b; where, independently of their occurrence, n is 0, 1 or 2; is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R7,
OR8, NR17aR17b, S(0)nR8a, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7b, C(=S)OR8, C(=S)SR8a, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R6 together form a linear C2-C7 alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3- Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10; independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF5, d-C6-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Si(R11)2R12, OR8, OS02R8a, S(0)nR8a, S(0)nNR 7aR 7 , NR17aR17b, C(=0)NR 7aR 7 , C(=S)NR 7aR 7 , C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15, NR 7a-C(=0)R7a, NR 7a-C(=S)R7a, NR 7a-C(=0)OR8, NR 7a-C(=0)NR 7aR 7 ,
phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9b,
or two R7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or two of R7b present on one carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C(=0)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR16,
phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
and a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10;
R9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6 haloalkynyl,
S(0)nR16, -S(0)nNR 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)NR 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)NR 7aR 7 , C(=NR 7)R15;
phenyl, benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10; and
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
and R9b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
and R9b together may form =CR13R14, =NR17 or =NOR16 moiety; independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF5, OH, CN , NO2, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci- C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl,
Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF5, OH, CN , NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- Ce-alkyhamino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl, Si(R11)2R12, OR16, OS(0)nR16a, -S(0)nR16a, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH, CN, NO2, SCN, SF5, OH, d-Ce-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
two R10 present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16, =NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2, CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0,
SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N , SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy; 12 independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8-halocycloalkyl-Ci-C4- alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN , NO2, SCN , SF5, OH, Ci- C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-
C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and benzyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy;
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN , NO2, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 , 2 or 3 radicals selected from the group consisting of CN, OH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, S(0)nR8a, S(0)nNR 7aR 7b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, NR 7a-C(=0)R7a, NR 7a-C(=0)OR8a and NR 7a-C(=0)NR 7aR 7 , phenyl, benzyl, 5- or 6-membered hetaryl or 5- or 6-membered hetaryl-methyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, d-Ce-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN, N02, SCN , SF5, OH, Ci-Ce-alkyI, C3-C6-cycloalkyl, Ci-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN , NO2, SCN, SF5 OH, Ci-Ce-alkyI, Cs-Ce-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , N02, SCN , SF5, OH , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl,
or,
R17a and R17b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R17a and R17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur or nitrogen, and may optionally be substituted with halogen, Ci- C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
R17a and R17b together may form =CR13R14, =N R17 or =NOR16 moiety;
R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN , d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-
C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , NO2, SCN , SF5, OH , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
OR16, S(0)nR16a, -S(0)nN R 7aR 7b, C(=0)R15, C(=0)OR16, C(=0)N R 7aR 7 , C(=S)R15, C(=S)SR16a, C(=S)N R 7aR 7 , C(=N R 7) R15; phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5
identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R18a and R18b are together a C2-C7 alkylene chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur or nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; the stereoisomers, tautomers and the salts thereof.
In a further special embodiment, the present invention relates to compounds of the formula (I), the stereoisomers, tautomers and the salts therof, wherein R16 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2- C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R7,
phenyl, benzyl, 5- or 6-membered hetaryl or 5- or 6-membered hetaryl-methyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, d-Ce-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci- C6-alkoxy)carbonyl and the other radicals have one of the meanings mentioned above.
Moreover, the present invention relates to and includes the following embodiments: agricultural and veterinary compositions comprising an amount of at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for combating invertebrate pests;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting growing plants from attack or infestation by invertebrate pests;
the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts, thereof for protecting plant proparagation material, especially seeds, from soil insects; the use of the compounds of formula (I), the stereoisomers, the tautomers or the salts thereof for protecting the seedlings roots and shoots of plants from soil and foliar insects; a method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof;
a method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof, in particular a method protecting crop plants from attack or infestation by animal pests, which comprises contacting the crop plants with a pesticidally effective amount of at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
a method for the protection of plant propagation, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
seeds comprising a compound of the formula (I) or an enantiomer, diastereomer or salt thereof;
the use of compounds of formula (I), the stereoisomers, the tautomers or the salts, in particular the veterinary acceptable salts, thereof for combating parasites in and on animals, in particular for the use in the treatment of animals infested or infected by parasites, for preventing animals of getting infected or infested by parasites or for protecting animals against infestation or infection by parasites;
a method for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;
a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises formulating a compound of formula (I) or a stereoisomer, tautomer and/or veterinary acceptable salt thereof with a carrier composition suitable for veterinary use; the use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
The present invention also relates to plant propagation materials, in particular as mentioned above to seeds, containing at least one compound of formula (I), a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof.
Detailed Description of Invention The present invention relates to every possible stereoisomer of the compounds of formula
(I), i.e. to single enantiomers, diastereomers and E/Z-isomers as well as to mixtures thereof and also to the salts thereof. The present invention relates to each isomer alone, or mixtures or combinations of the isomers in any proportion to each other. Depending on the substitution pattern, the compounds of the formula (I) may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon ring atom carrying radical R1. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure
enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers, E/Z-isomers) and mixtures thereof, in particular the E/Z-isomers with regard to the C=N double bond in formula (I).
The present invention also relates to potential tautomers of the compounds of formula (I) and also to the salts of such tautomers. The present invention relates to the tautomer as such as well as to mixtures or combinations of the tautomers in any proportion to each other. The term "tautomers" encompasses isomers, which are derived from the compounds of formula (I) by the shift of an H-atom involving at least one H-atom located at a nitrogen, oxygen or sulphur atom. Examples of tautomeric forms are keto-enol forms, imine-enamine forms, urea-isourea forms, thiourea-isothiourea forms, (thio)amide-(thio)imidate forms etc.
The compounds of the present invention, i.e. the compounds of formula (I), their stereoisomers, their tautomers as well as their salts, in particular their agriculturally acceptable salts and their veterinarily acceptable salts, may be amorphous or may exist in one ore more different crystalline states (polymorphs) or modifications which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula (I), mixtures of different crystalline states or modifications of the respective
stereoisomers or tautomers, as well as amorphous or crystalline salts thereof.
Salts of the compounds of the formula (I) are preferably agriculturally salts as well as veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base. Suitable agriculturally or veterinary useful salts are especially the salts of those cations or anions, in particular the acid addition salts of those acids, whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci- C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium,
trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4- alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci- C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn- Cm indicates in each case the possible number of carbon atoms in the group.
"Halogen" will be taken to mean fluoro, chloro, bromo and iodo.
The term "partially or completely halogenated" will be taken to mean that 1 or more, e.g. 1 , 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. For example, partially or completely halogenated alkyl is also termed haloalkyl, partially or completely halogenated cycloalkyl is also termed halocycloalkyl, partially or completely halogenated alkylenyl is also termed haloalkenyl, partially or completely halogenated alkylynyl is also termed haloalkynyl, partially or completely halogenated alkoxy is also termed haloalkoxy, partially or completely halogenated alkylthio is also termed haloalkthio, partially or completely halogenated alkylsulfinyl is also termed haloalkylsulfinyl, partially or completely halogenated alkylsulfonyl is also termed haloalsulfonyl, partially or completely halogenated cycloalkylalkyl is also termed halocycloalkylalkyl.
The term "Cn-Cm-alkyl" as used herein, and also in Cn-Cm-alkylamino, di-Cn-Cm-alkylamino, Cn-Cm-alkylaminocarbonyl, di-(Cn-Cm-alkylamino)carbonyl, Cn-Cm-alkylthio , Cn-Cm-alkylsulfinyl and Cn-Cm-alkylsulfonyl, refers to a branched or unbranched saturated hydrocarbon group having n to m, e.g. 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, hexyl, 1 ,1 - dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2- trimethylpropyl, 1 -ethyl-1 -methylpropyl, 1 -ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. Ci-C4-alkyl means for example methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2-methylpropyl or 1 ,1 -dimethylethyl.
The term "Cn-Cm-haloalkyl" as used herein, and also in Cn-Cm-haloalkylthio (= Cn-Cm- haloalkylsulfenyl), Cn-Cm-haloalkylsulfinyl and Cn-Cm-haloalkylsulfonyl, refers to a straight-chain or branched alkyl group having n to m carbon atoms, e.g. 1 to 10 in particular 1 to 6 carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, for example Ci-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 - bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl,
pentafluoroethyl and the like. The term Ci-Cio-haloalkyl in particular comprises C1-C2- fluoroalkyl, which is synonym with methyl or ethyl, wherein 1 , 2, 3, 4 or 5 hydrogen atoms are substituted by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl. "Halomethyl" is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
Similarly, "Cn-Cm-alkoxy", "Cn-Cm-alkylthio", or "Cn-Cm-alkylsulfenyl", respectively, "Cn-Cm- alkylsulfinyl" or "Cn-Cm-alkylsulfonyl" refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through O, S, S(=0) or S(=0)2 linkages, respectively, at any bond in the alkyl group. Accordingly, the terms "Cn-Cm-haloalkoxy", "Cn-Cm-haloalkylthio" or "Cn-Cm-alkylsulfenyl", respectively, "Cn-Cm-haloalkylsulfinyl" or "Cn-Cm-haloalkylsulfonyl", refer to straight-chain or branched alkyl groups having n to m carbon atoms, e.g. 1 to 10, in particular 1 to 6 or 1 to 4 carbon atoms (as mentioned above) bonded through O, S, S(=0) or S(=0)2 linkages, respectively, at any bond in the haloalkyl group, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
The term "Cn-Cm-alkoxy" is a Cn-Cm-alkyl group, as defined above, attached via an oxygen atom. Ci-C2-Alkoxy is methoxy or ethoxy. Ci-C4-Alkoxy is, for example, methoxy, ethoxy, n- propoxy, 1 -methylethoxy (isopropoxy), butoxy, 1 -methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy). Ci-C6-Alkoxy includes the meanings given for Ci-C4-alkoxy and also includes, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3- methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethyl butoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2- trimethylpropoxy, 1 -ethyl-1 -methylpropoxy or 1 -ethyl-2-methylpropoxy. Ci-Cs-Alkoxy includes the meanings given for Ci-C6-alkoxy and also includes, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof. Ci-Cio-Alkoxy includes the meanings given for Ci- Ce-alkoxy and also includes, for example, nonyloxy, decyloxy and positional isomers thereof.
The term "Cn-Cm-alkylthio" is a Cn-Cm-alkyl group, as defined above, attached via a sulfur atom. Ci-C2-Alkylthio is methylthio or ethylthio. Ci-C4-Alkylthio is, for example, methylthio, ethylthio, n-propylthio, 1 -methylethylthio (isopropylthio), butylthio, 1 -methylpropylthio (sec- butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio). C1-C6- Alkylthio includes the meanings given for Ci-C4-alkylthio and also includes, for example, pentylthio, 1 -methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1 -dimethylpropylthio, 1 ,2- dimethylpropylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 -methylpentylthio, 2- methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2- dimethylbutylthio, 1 ,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio,
3,3-dimethylbutylthio, 1 -ethylbutylthio, 2-ethylbutylthio, 1 ,1 ,2-trimethylpropylthio, 1 ,2,2- trimethylpropylthio, 1 -ethyl-1 -methylpropylthio or 1-ethyl-2-methylpropylthio. d-Cs-Alkylthio includes the meanings given for Ci-C6-alkylthio and also includes, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof. Ci-Cio-Alkylthio includes the meanings given for d-Cs-alkylthio and also includes, for example, nonylthio, decylthio and positional isomers thereof.
The term "Cn-Cm-alkylsulfinyl" is a Cn-Cm-alkyl group, as defined above, attached via a
S(=0) group. The term "Cn-Cm-alkylsulfonyl" is a Cn-Cm-alkyl group, as defined above, attached via a S(=0)2 group.
The term "Cn-Cm-haloalkyloxy" is a Cn-Cm-haloalkyl group, as defined above, attached via an oxygen atom. Examples include Ci-C2-haloalkoxy, such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1 - bromoethoxy, 1 -fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro- 2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy and pentafluoroethoxy.
The term "Cn-Cm-haloalkylthio" is a Cn-Cm-haloalkyl group, as defined above, attached via a sulfur atom. Examples include Ci-C2-haloalkylthio, such as chloromethylthio,
bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1 - chloroethylthio, 1 -bromoethylthio, 1 -fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2- trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2- fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio and the like.
Similarly the terms Ci-C2-fluoroalkoxy and Ci-C2-fluoroalkylthio refer to Ci-C2-fluoroalkyl which is bound to the remainder of the molecule via an oxygen atom or a sulfur atom, respectively. The term "Cn-Cm-haloalkylsulfinyl" is a Cn-Cm-haloalkyl group, as defined above, attached via a S(=0) group. The term "Ci-Cm-haloalkylsulfonyl" is a Ci-Cm-haloalkyl group, as defined above, attached via a S(=0)2 group.
The term "C2-Cm-alkenyl" as used herein denotes a linear or branched ethylenically unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and a C=C- double bond in any position, such as ethenyl, 1 -propenyl, 2-propenyl, 1 -methyl-ethenyl, 1 - butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2- methyl-2-propenyl, 1 -pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -methyl-1 -butenyl, 2-methyl- 1 -butenyl, 3-methyl-1 -butenyl, 1 -methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1 - methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1 -dimethyl-2-propenyl, 1 ,2-dimethyl- 1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1 -hexenyl, 2- hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1 -methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-
1 - pentenyl, 4-methyl-1 -pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2- pentenyl, 4-methyl-2-pentenyl, 1 -methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl- 4-pentenyl, 1 ,1 -dimethyl-2-butenyl, 1 ,1 -dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-
2- butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1 -butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-
3- butenyl, 2,2-dimethyl-3-butenyl, 2, 3-dimethyl-1 -butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl- 3-butenyl, 3, 3-dimethyl-1 -butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1 -ethyl-2-butenyl, 1 - ethyl-3-butenyl, 2-ethyl-1 -butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2- propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1 -ethyl-2-methyl-1 -propenyl and 1 -ethyl-2-methyl-2- propenyl.
The term "C2-Cm-haloalkenyl" as used herein, which is also expressed as "C2-Cm-alkenyl which is partially or completely halogenated", refers to C2-Cm-alkenyl, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example 1 -fluoroethenyl, 2-fluoroethenyl, 2,2- difluoroethenyl, 1 ,2,2-trifluoroethenyl, 1 -fluoro-2-propenyl, 2-fluoro-2-propenyl, 3-fluoro-2- propenyl, 1 -fluoro-1 -propenyl, 1 ,2-difluoro-1 -propenyl, 3,3-difluoropropen-2-yl, 1 -chloroethenyl, 2-chloroethenyl, 2,2,-dichloroethenyl, 1 -chloro-2-propenyl, and the like.
The term "C2-Cm-alkynyl" as used herein refers to a linear or branched unsaturated hydrocarbon group having 2 to m, e.g. 2 to 10 or 2 to 6 carbon atoms and containing at least one triple bond, such as ethynyl, propynyl, 1 -butynyl, 2-butynyl, and the like.
The term "C2-Cm-haloalkynyl" as used herein, which is also expressed as "C2-Cm-alkynyl which is partially or completely halogenated", refers to C2-Cm-alkynyl, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine. Examples of C2-Cm-haloalkynyl include 1 -fluoro-2- propenyl, 2-fluoro-2-propenyl, 3-fluoro-2-propenyl, 1 -fluoro-2-propynyl and 1 ,1 -difluoro-2- propenyl, and the like.
The term "C3-Cm-cycloalkyl" as used herein refers to a monocyclic and polycyclic 3- to m- membered saturated cycloaliphatic radical, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1 ]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1 ]octyl. Preferably, the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
The term "C3-Cm-cycloalkenyl" as used herein refers to a monocyclic and polycyclic 3- to m-membered unsaturated cycloaliphatic radical, e.g. cyclopropenyl, cyclobutenyl,
cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, bicyclo[2.2.1]heptenyl, bicyclo[3.1.1 ]heptenyl, bicyclo[2.2.2]octenyl and bicyclo[3.2.1]octenyl. Preferably, the term cycloalkenyl denotes a monocyclic unsaturated hydrocarbon radical.
The term "C3-Cm-halocycloalkyl" as used herein, which is also expressed as "cycloalkyl which is partially or completely halogenated", refers to C3-Cm-cycloalkyl as mentioned above, in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine. Examples of C3-Cm-halocycloalkyl include 1 - fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 1 -chlorocyclcopropyl, 2- chlorocyclopropyl, 2,2-dichlorocyclopropyl, 2,3-difluorocyclopropyl, 1 -fluorocycobutyl etc.
The term "C3-Cm-cycloalkyl-Ci-C4-alkyl" refers to a C3-Cm-cycloalkyl group as defined above, which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above. Examples for C3-Cm-cycloalkyl-Ci-C4-alkyl are cyclopropyl methyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
The term "C3-Cm-halocycloalkyl-Ci-C4-alkyl" refers to a C3-Cm-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
The term "Ci-C4-alkoxy-Ci-C4-alkyl" as used herein refers to alkyl having 1 to 4 carbon atoms, e.g. like specific examples mentioned above, wherein one hydrogen atom of the alkyl radical is replaced by an Ci-C4-alkoxy group. Examples are methoxymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobutoxymethyl, tert- butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 -isopropoxyethyl, 1 -n- butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert-butoxyethyl, 2-methoxyethyl, 2- ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n-butoxyethyl, 2-sec-butoxyethyl, 2- isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxypropyl, 1 - isopropoxypropyl, 1 -n-butoxypropyl, 1 -sec-butoxypropyl, 1 -isobutoxypropyl, 1 -tert-butoxypropyl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-n-butoxypropyl, 2- sec-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxypropyl, 3-methoxypropyl, 3-ethoxypropyl, 3- propoxypropyl, 3-isopropoxypropyl, 3-n-butoxypropyl, 3-sec-butoxypropyl, 3-isobutoxypropyl, 3- tert-butoxypropyl and the like.
The term Ci-C4-haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms, either in the alkoxy moiety or in the alkyl moiety or in both, are replaced by halogen atoms. Examples are difluoromethoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl, 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro-methoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like. The term "Cn-Cm-alkoxycarbonyl" is a Cn-Cm-alkoxy group, as defined above, attached via an carbonyl group atom. Ci-C2-Alkoxycarbonyl is methoxycarbonyl or ethoxycarbonyl. C1-C4- Alkoxy is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1 - methylethoxycarbonyl, butoxycarbonyl, 1 -methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1 ,1 -dimethylethoxycarbonyl. Ci-C6-Alkoxycarbonyl includes the meanings given for C1-C4- alkoxycarbonyl and also includes, for example, pentoxycarbonyl, 1 -methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 1 ,1 -dimethylpropoxycarbonyl, 1 ,2- dimethylpropoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1 -ethylpropoxycarbonyl,
hexoxycarbonyl, 1 -methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 ,1 -dimethylbutoxycarbonyl, 1 ,2-dimethylbutoxycarbonyl,
1 ,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl,
3,3-dimethylbutoxycarbonyl, 1 -ethylbutoxy, 2-ethylbutoxycarbonyl, 1 ,1 ,2- trimethylpropoxycarbonyl, 1 ,2,2-trimethylpropoxycarbonyl, 1 -ethyl-1 -methylpropoxycarbonyl or
1 - ethyl-2-methylpropoxycarbonyl.
The term "aryl" as used herein refers to an aromatic hydrocarbon radical such as naphthyl or in particular phenyl.
The term "3- to 6-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane and cyclohexane rings. The term "3- to 7-membered carbocyclic ring" as used herein refers to cyclopropane, cyclobutane, cyclopentane, cyclohexane and cycloheptane rings.
The term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms" or "containing heteroatom groups", wherein those heteroatom(s) (group(s)) are selected from N, O, S, NO, SO and SO2 and are ring members, as used herein refers to monocyclic radicals, the monocyclic radicals being saturated, partially unsaturated or aromatic. The heterocyclic radical may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member.
Examples of 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic rings include: oxiranyl, aziridinyl, azetidinyl, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3
tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4 isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3 isothiazolidinyl, 4- isothiazolidinyl, 5 isothiazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4 oxadiazolidin 5 yl, 1 ,2,4- thiadiazolidin-3-yl, 1 ,2,4 thiadiazolidin-5-yl, 1 ,2,4 triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4 thiadiazolidin-2-yl, 1 ,3,4 triazolidin-2-yl, 2-tetrahydropyranyl, 4 tetrahydropyranyl, 1 ,3-dioxan-5- yl, 1 ,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4 hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5 hexahydropyrimidinyl,
2- piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4 hexahydrotriazin-3-yl, 2-morpholinyl, 3- morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1 -oxothiomorpholin-2-yl, 1 -oxothiomorpholin-
3- yl, 1 ,1 -dioxothiomorpholin-2-yl, 1 ,1 -dioxothiomorpholin-3-yl, hexahydroazepin-1 -, -2-, -3- or -4- yl, hexahydrooxepinyl, hexahydro-1 ,3-diazepinyl, hexahydro-1 ,4-diazepinyl, hexahydro-1 ,3- oxazepinyl, hexahydro-1 ,4-oxazepinyl, hexahydro-1 ,3-dioxepinyl, hexahydro-1 ,4-dioxepinyl and the like. Examples of 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic rings include: 2,3-dihydrofur-2-yl, 2,3-d ihyd rofur-3-yl , 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- dihydrothien-2-yl, 2,3 dihydrothien-3-yl, 2,4 dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2- yl, 2-pyrrolin-3-yl, 3 pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4 isoxazolin 3 yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2 isoxazolin-5-yl, 3-isoxazolin-5-yl, 4- isoxazolin-5-yl, 2-isothiazolin-3-yl, 3 isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3- isothiazolin-4-yl, 4 isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3 dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3 dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4 dihydropyrazol-3-yl, 3,4-dihydropyrazol-4- yl, 3,4-dihydropyrazol-5-yl, 4,5 dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5 dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3 dihydrooxazol- 4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4 dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 3,4-dihydrooxazol-5-yl, 3,4 dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4- yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4 di- or
tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5 di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1 ,3,5-di- or tetrahydrotriazin-2-yl, 1 ,2, 4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6- tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5- , -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]azepin-1 -, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, such as 2,3,4,5-tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7 tetrahydro[1 H]oxepin-2- , -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7 tetrahydro[1 H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1 ,3- diazepinyl, tetrahydro-1 ,4-diazepinyl, tetrahydro-1 ,3-oxazepinyl, tetrahydro-1 ,4-oxazepinyl, tetrahydro-1 ,3-dioxepinyl and tetrahydro-1 ,4-dioxepinyl.
Examples of 5- or 6-membered aromatic heterocyclic rings, also termed heteroaromatic rings, heteroaryl or hetaryl, include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3- pyrazolyl, 4-pyrazo-"lyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4 thiazolyl, 5- thiazo-"lyl, 2-imidazolyl, 4-imidazolyl, 1 ,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3- pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.
A "Ci-Cm-alkylene" is divalent branched or preferably non-branched or linear saturated aliphatic chain having 1 to m, e.g. 1 to 7 carbon atoms, for example Chb, CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2,
CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.
Embodiments of the present invention as well preferred compounds of the present invention are outlined in the following paragraphs. The remarks made below concerning preferred embodiments of the variables of the compounds of formula (I), especially with respect to their substituents Het, Y, R1, R2, R3a, R3b, including the variables X, R4, R5a, R5b, as well as R6 and the variable k are valid both on their own and, in particular, in every possible combination with each other.
When # appears in a formula showing a preferred substructure of a compound of the present invention, it denotes the attachment bond in the remainder molecule. Preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 to Het-24, with preference given to compounds of the formula (I), their stereoisomers, there tautomers and their salts, where Het is selected from the radicals of the formulae Het-1 , Het-1 1 and Het-24:
Figure imgf000037_0001
Het-1 Het-2 Het-3 Het-4 Het-5
Figure imgf000037_0002
hfet-6 Het-7 Het-8 Het-9 Het-10
Figure imgf000037_0003
Het-11 Het-12 Het-13 Het-14 Het-15
Figure imgf000037_0004
Het-16 Het-17 Het-18 Het-19 Het-20
Figure imgf000037_0005
Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond in formula (I), and wherein R6 and k are as defined above and where R6a is hydrogen or has one of the meanings given for R6 and where R6b is hydrogen or a C-bound radical mentioned as R6 and where R6b is in particular hydrogen, Ci-C4-alkyl or C1-C4- haloalkyl. In particular k is 0, 1 or 2, especially 0 or 1 . In formulae Het-1 , Het-2, Het-3, Het-4, Het-7, Het-8, Het-9, Het-10, Het-1 1 , Het-18 and Het-21 , k is especially 1. In particular R6a in formulae Het-12, Het-13, Het-14, Het-16, Het-17, Het-19, Het 20 and Het-22 is different from hydrogen. Irrespectively of its occurrence, R6 is preferably selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four last mentioned radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may be (further) substituted independently from one another with one or more (e.g. 1 , 2 or 3) identical or different R7, or R6 may also be a radical selected from the group consisting of OR8, NR17aR17b, S(0)nR8a, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7b, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 . Irrespectively of its occurrence, R6 is in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,
trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Irrespectively of its occurrence, R6a is preferably selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be partly or completely halogenated, in particular by fluorine or chlorine, or may further substituted independently from one another with one or more identical or different R7, or R6a may also be a radical selected from the group consisting of OR8, NR17aR17b, S(0)nR8a, S(0)nNR 7aR 7 , C(=0)R7a, C(=0)NR 7aR 7 , C(=0)OR8, C(=S)R7a, C(=S)NR 7aR 7 ,
C(=NR17)R7a, C(=NR17)NR17aR17b. Irrespectively of its occurrence, R6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, C1-C4- alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Irrespectively of its occurrence, R6b is in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Particularly preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24,
Figure imgf000039_0001
Het-1 Het-11a Het-24 where
R6 is selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl; and where
R6a is selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and C1-C4- haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci- C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl and
k is 0, 1 or 2.
A particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 , where k is 0, 1 or 2, in particular 1 or 2 and especially 1 and where R6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, C1-C4- alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl,
trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, C1-C2- alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. Amongst the compounds of this particular group of embodiments, a particular sub-group of embodiments relates to compounds of the formula (I), to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 a
Figure imgf000039_0002
Het-1 a where
R6 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl or pentafluoroethyl;
R6a is as defined above and in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine and Ci-C4-alkyl, such as methyl or ethyl, more preferably is hydrogen.
A special embodiment of the radical Het-1 a is 6-chloropyridin-3-yl, i.e. R6a is hydrogen and R6 is chlorine. A further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3- yl, i.e. R6a is hydrogen and R6 is trifluoromethyl.
Another particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-1 1 , where k is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-1 1 a,
Figure imgf000040_0001
where R6a is as defined above and wherein R6a is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and C1-C4- haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl. A special embodiment of the radical Het-1 1 a is 2-chlorothiazol-5-yl, i.e. R6a is chlorine.
Another particularly preferred group of embodiments relates to compounds of formula (I) to the stereoisomers, the tautomers and to the salts thereof, wherein Het is a radical of formula Het-24, where k is 0, 1 or 2, in particular 0 or 1 , and where R6, if present, is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, Ci- C4-alkyl, such as methyl or ethyl, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, and even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
Preferred are compounds of formula (I), wherein R1 and R2 are independently from each other selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl.
Preferred are also compounds of formula (I), wherein R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
Preferred are also compounds of formula (I), wherein R1 and R2 may together be
=CR13R14.
Even more preferred are compounds of formula (I), wherein R1 and R2 are independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl.
Preferably at least one of the radicals R1 and R2 is hydrogen.
Even more preferred are compounds of formula (I), wherein R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen.
In a particular group of embodiments, R1 and R2 are both hydrogen.
A group of embodiments relates to compounds of formula (I), wherein R3a is different from hydrogen. Another group of embodiments relates to compounds of formula (I), wherein R3a is hydrogen.
Preferably, R3a is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
- Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q1 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3. In the context of R3a, the variable R7 is in particular selected from the group consisting of N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N02, CN, cyclopropyl and Ci-C4-alkoxy.
In the context of R3a, the variable R10 is in particular selected from the group consisting of halogen, N02, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci- C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely
halogenated, and especially selected from the group consisting of halogen, such as fluorine or chlorine, N02, CN and Ci-C4-alkoxy, such as methoxy or ethoxy. In the context of R3a, the variable Cyc1 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridinyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R10, as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of NO2, CN and Ci-C4-alkoxy. Cyc1 is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R10, as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
In particular, R3a is Ci-C6-alkyl or Ci-C6-haloalkyl, in particular Ci-C3-alkyl or C1-C3- haloalkyl, where alkyl and haloalkyl may further carry any combination of 1 , 2 or 3 radicals R7, or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl. In this context, R7 is as defined above and in particular from the group consisting of NO2, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.
Especially, R3a is selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2.
Another group of embodiments relates to compounds of formula (I), wherein R3a is a radical, which is selected from the group consisting of C(=0)NR9aR9b, C(=S)NR9aR9b,
C(=0)OR8, C(=0)R7a, C(=S)R7a and S(0)nR8a. In the context of this embodiment, the radicals R7a, R8, R8a, R9a and R9b are as defined above or have in particular the following meanings:
R7a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, , where the phenyl ring in the last two mentioned radicals is unsbustituted or carries 1 , 2, 3 or 4 radicals R10, phenylcarbonyl, phenoxycarbonyl and
phenylaminocarbonyl, wherein the phenyl ring in the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2,
SCN, SF5, OH, d-Ce-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10; R9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
In the context of radicals R7a, R8, R8a, R9a and R9b the radical R10 is in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, NO2, CN, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated. Preferably, R3b is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
- Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3. In the context of R3b, the variable R7 is in particular selected from the group consisting of N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N02, CN, cyclopropyl and Ci-C4-alkoxy.
In the context of R3b, the variable R10 is in particular selected from the group consisting of halogen, N02, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci- C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely
halogenated, and especially selected from the group consisting of halogen, such as fluorine or chlorine, N02, CN and Ci-C4-alkoxy, such as methoxy or ethoxy.
In the context of R3b, the variable Cyc2 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridinyl, wherein phenyl and hetaryl are unsubstituted or carry 1 , 2, 3, 4 or 5 radicals R10, as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N02, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and especially selected from the group consisting of N02, CN and Ci-C4-alkoxy. Cyc2 is especially phenyl, which is unsubstituted or carries 1 , 2 or 3 radicals R10, as defined above, which are in particular selected from the group consisting of halogen, such as fluorine, chlorine or bromine, N02, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
In particular, R3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyi may carry 1 , 2 or 3 further radicals R7, which are identical or different. In this context, the radicals R7 are as defined above and in particular from the group consisting of N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.
More particularly, R3b is selected from the group consisting of Ci-C3-alkyl and C1-C3- haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and
trifluoromethyl.
In particular groups (1 ) of embodiments, the group Y in formula (I) is a group Y1, where X is in particular O and where R4 is as defined herein.
In further particular groups (2) of embodiments, the group Y in formula (I) is a group Y2, where X is in particular O and where R4 is as defined herein.
In yet further particular groups (3) of embodiments, the group Y in formula (I) is a group Y3, where X is in particular O and where R4 and R5a as defined herein.
In further particular groups (4) of embodiments, the group Y in formula (I) is a group Y4, where R5a and R5b as defined herein.
In further particular groups (5) of embodiments, the group Y in formula (I) is a group Y4, where R5a and R5b as defined herein.
Particular preference is given to groups (1 ) and (3) of embodiments and especially to groups (3) of embodiments.
The radical X in the groups Y1, Y2 and Y3 in the groups (1 ), (2) and (3) embodiments is in particular O.
In the context of groups (1 ), (2) and (3) of embodiments, the radical R4 is in particular selected from the group consisting of
hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
OR8, NR18aR18b, C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)OR8, C(=0)R7a, C(=S)R7a, phenyl, which is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized. In the context of groups (1 ), (2) and (3) of embodiments, the radical R4 is even more particularly selected from the group consisting of
hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
OR8, NR18aR18b,
phenyl, which is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized.
In the context of groups (1 ), (2) and (3) embodiments, the radical R4 is even more particularly selected from the group consisting of
Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
NR18aR18b,
phenyl, which is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 5- or 6- membered aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the aromatic heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10.
In the context of groups (1 ), (2) and (3) of embodiments, particular groups (1 a), (2a) and (3a) of embodiments relate to compounds of the formula (I), wherein the variable R4 is C1-C6- alkyl, which is unsubstituted, partly or completely halogenated and/or may carry any
combination of 1 , 2 or 3 radicals R7, where R7 is as defined above and in particular selected from the group consisting of from CN, NO2, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C3-C6-cycloalkyl, S(0)nR8a and S(0)nNR 7aR 7b.
Examples of this type of radicals R4 include the following radicals R-4.1 to R-4.18:
R-4.1 methyl;
R-4.2 ethyl;
R-4.3 isopropyl;
R-4.4 tert. -butyl;
R-4.5 trifluoromethyl;
R-4.6 2,2-difluoroethyl;
R-4.7 2,2,2-trifluoroethyl;
R-4.8 cyanomethyl;
R-4.9 1 -cyanoethyl; R-4.10 nitrom ethyl;
R-4.1 1 1 -nitroethyl;
Figure imgf000046_0001
R-4.13 CF2-S(0)-CH3;
R-4.14 CF2-S(0)2-CH3;
Figure imgf000046_0002
R-4.16 CF2-S(0)-C2H5;
R-4.17 CF2-S(0)2-C2H5;
R-4.18 1 -cyano-1 -methylethyl
In the context of groups (1 ), (2) and (3) of embodiments, further particular groups (1 b), (2b) and (3b) of embodiments relate to compounds of the formula (I), wherein the variable R4 is 6-membered heteroaryl, which is in particular selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, wherein 6-membered heteroaryl is unsubsituted or carries 1 , 2, 3 or 4 radicals R10, which are in particular selected from halogen, CN, N02, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
Examples of this type of radicals R4 include 2-thiazolyl (R-40.1 ) and 2-pyrazinyl (R-40.2).
In the context of groups (1 ), (2) and (3) of embodiments, yet further particular groups (1 c), (2c) and (3c) of embodiments relate to compounds of the formula (I), wherein the variable R4 is a radical of formula R-41 or R-42:
Figure imgf000046_0003
R-41 R-42 wherein # indicates the bond to the carbonyl group in formula (I)
A is CH2, CH2CH2 or CH2CH2CH2,
R10aa is hydrogen or a radical R10 as defined above, which R10aa is in particular selected from hydrogen, halogen, especially fluorine, S(0)nR16a, CN and N02, where n is 0, 1 or 2 and R16a is as defined above an in particular selected from Ci-C4-alkyl and Ci- C4-haloalkyl.
Examples of radicals R-41 and R-42 include the following radicals R-41.1 to R-41.20 and
R-42.1 to R-42.8:
R-41.1 : cyclopropyl;
R-41.2: cyclobutyl;
R-41.3: 1 -fluorocyclopropyl;
R-41.4: 1 -fluorocyclobutyl;
R-41.5: 1 -cyanocyclopropyl;
R-41.6: 1 -cyanocylobutyl; R-41 7: -nitrocyclopropyl;
R-41 8: -nitrocyclobutyl;
R-41 9: -(methylthio)cyclopropyl;
R-41 10 -(methylsulfinyl)cyclopropyl;
R-41 1 1 -(methylsulfonyl)cyclopropyl;
R-41 12 -(ethylthio)cyclopropyl;
R-41 13 -(ethylsulfinyl)cyclopropyl;
R-41 14 -(ethylsulfonyl)cyclopropyl;
R-41 15 -(methylthio)cyclobutyl;
RR--4411.1166: 1 -(methylsulfinyl)cyclobutyl;
R-41 17 -(methylsulfonyl)cyclobutyl;
R-41 18 -(ethylthio)cyclobutyl;
R-41 19 -(ethylsulfinyl)cyclobutyl;
R-41 20 -(ethylsulfonyl)cyclobutyl;
RR--4422.11 :: 2-oxiranyl;
R-42 2: 2-oxetanyl;
R-42 3: 2-fluoro-2-oxiranyl;
R-42 4: 2-fluoro-2-oxetanyl;
R-42 5: 2-cyano-2-oxiranyl;
RR--4422.66:: 2-cyano-2-oxetanyl;
R-42 7: 2-nitro-2-oxiranyl and
R-42 8: 2-nitro-2-oxetanyl.
In the context of groups (1 ), (2) and (3) of embodiments, further particular groups (1 d), (2d) and (3d) of embodiments relate to compounds of the formula (I), wherein the variable R4 is a radical of formula R-43:
Figure imgf000047_0001
wherein # indicates the bond to the carbonyl group in formula (I),
Rx is hydrogen, halogen, CN, N02, CrC4-alkyl, Ci-C4-haloalkyl, NR17aR17b,
S(0)2NR17aR17b, S(0)2R8a or C(=0)OR8 and in particular hydrogen, CN, Ci-C4-alkyl, such as methyl, or Ci-C4-haloalkyl, such as trifluoromethyl;
R16 is as defined above and in particular selected from the group consisting of hydrogen, Ci-C6-alkyl and C2-C6-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R7, which are as defined above, and which are in particular selected from the group consisting of N02, CN, OR8, S(0)nR8a, NR17aR17b, C(=0)NR17aR17b, C(=0)OR8, C(=0)R15 and NR 7a-C(=0)R7a, or R16 is benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, d-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, Ci-Ce haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl.
In formula R-43, R16 is especially selected from the group consisting of hydrogen, C1-C4- alkyl, Ci-C4-haloalkyl, where the two aforementioned radicals may carry 1 or 2 radicals R7, which are selected from the group consisting of NO2, CN and OR8, C2-C4-alkenyl, C2-C4- haloalkenyl, and benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di- (Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl.
Examples of radicals R-43 are the radicals R-43.1 to R-43.44, where Rx and R16 are as defined in the rows of the following table A:
Table A: Radicals R-43
Figure imgf000048_0001
Figure imgf000049_0001
CH2-C6H5: benzyl
CH2-(4-CI-C6H4): 4-chlorobenzyl
CH2-(4-(OCHs)-C6H4): 4-methoxybenzyl
In the context of groups (1 ), (2) and (3) of embodiments, further particular groups (1 e), (2e) and (3e) of embodiments relate to compounds of the formula (I), wherein the variable R4 is a radical of formula NR18aR18b.
In context of the radical of formula NR18aR18b, the radicals R18a and R18b are each independently from one another preferably selected from the group consisting of
hydrogen,
Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl or isobutyl, wherein the aforementioned alkyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, especially 1 radical R7
C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2 or CH=CH-CH2, wherein the aforementioned alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, especially 1 radical R7; C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, in particular C3-C6-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10;
Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy,
Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy,
Ci-C4-alkylcarbonyl, such as acetyl or propionyl,
Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl,
Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert- butoxycarbonyl,
NH2-C(0),
Ci-C4-alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl,
NH2-S(0)2,
Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl,
Ci-C4-haloalkylsulfonyl, such as trifluoromethylsulfonyl,
Ci-C4-alkylaminosulfonyl, such as methylaminosulfonyl or ethylaminosulfonyl, di-(Ci-C4-alkyl)aminosulfonyl, such as dimethylaminosulfonyl or diethylaminosulfonyl; phenyl, which is unsubstituted or carries 1 , 2 3 or 4 radicals R10,
phenoxy, which is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci- C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
and a 5- or 6-membered aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10.
In the context of radicals R18a and R18b the radical R7 is as defined above and in particular, independently of each other selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, S(0)nR8a, S(0)nNR 7aR 7b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7 , C(=0)OR8, C(=0)R15, NR 7a-C(=0)R7a, NR 7a-C(=0)OR8a, NR 7a-C(=0)NR 7aR 7 , phenyl and phenoxy,
where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1 , 2, 3, 4 or 5 radicals R10.
In context of radical radicals R18a and R18b, the radical R10 is as defined herein and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, C1-C4- haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2- butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, such as methylthio or ethylthio, Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, C1-C4- haloalkylthio, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1 ,1 - difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, C1-C4- haloalkylsulfonyl, such as fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2-fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2- trifluoroethylsulfonyl, SO2NH2, Ci-C4-alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl,
diethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl and the like.
R18a and R18b may also together be a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7- membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C6- alkoxy, Ci-C6-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C6-alkylthio, in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
isobutylsulfanyl, and Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
In particular R18a is selected from the group consisting of hydrogen and Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and especially hydrogen, while R18b has one of the above given meanings and where R18b is in particular
hydrogen,
- Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
- C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2 or CH=CH-CH2, wherein each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, which is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl; or
R18b is Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl, Ci-C4-alkylaminocarbonyl, such as methylaminocarbonyl or
ethylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl,
diethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl, NH2-S(0)2, Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylsulfonyl, such as trifluoromethylsulfonyl, C1-C4- alkylaminosulfonyl, such as methylaminosulfonyl or ethylaminosulfonyl, di-(Ci-C4- alkyl)aminosulfonyl, such as dimethylaminosulfonyl or diethylaminosulfonyl;
or R18a and R18b may also together be a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7- membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C6-alkylthio, in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
isobutylsulfanyl, and Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
Especially, R18a is selected from the group consisting of hydrogen and Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and especially hydrogen, while R18b is in particular
hydrogen,
- Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
- C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH or CH=CH-CH2, wherein each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, which is as defined above and in particular selected from the group consisting of CN , OH, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6- cycloalkyl, such as cyclopropyl or cyclobutyl;
R18a and R18b may also together be a C2-C6 alkylene chain and form a 3-, 4-, 5-, 6- or 7-membered saturated ring together with the nitrogen atom they are bonded to.
Examples of radicals NR18aNR18b include the following radicals R-44.1 to R-44.10
R-44.1 NH2;
R-44.2 methylamino;
R-44.3 ethylamino;
R-44.4 (2,2-difluoroethyl)amino;
R-44.5 (2,2,2-trifluoroethyl)amino;
R-44.6 dimethylamino;
R-44.7 diethylamino;
R-44.8 cyclopropylmethylamino;
R-44.9 1 -(cyclopropyl)ethylamino;
R-44.10: 1 -aziridinyl.
In the context of groups (1 ), (2) and (3) of embodiments, further particular groups (1f), (2f) and (3f) of embodiments relate to compounds of the formula (I), wherein the variable R4 is O-R8, wherein R8 is as defined above and in particular selected from the group consisting of
- Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl,
C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH or CH=CH-CH2,
wherein each of the alkyl and alkenyl radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, which is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl; or
- C3-C6-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, which are as defined above and preferably selected from the group consisting of halogen, such as fluorine or chlorine, CN, OH , Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, C1-C4- haloalkoxy, such as difluoromethoxy or trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl.
Examples of radicals OR8 include the following radicals R-45.1 to R-45.6
R-45.1 methoxy;
R-45.2 ethoxy;
R-45.3 n-propoxy;
R-45.4 isopropoxy;
R-45.5 n-butoxy;
R-45.6 tert.-butoxy.
In context of radical R4, the radical R7 is as defined above and in particular selected from the group consisting of CN, OH, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-alkylthio, such as methylsulfanyl or ethylsulfanyl, Ci-C4-haloalkoxy, such as difluoromethoxy or
trifluoromethoxy, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, S(0)nR8a, S(0)nNR17aR17b, NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, NR 7a-C(=0)R7a, NR 7a- C(=0)OR8a, NR 7a-C(=0)NR 7aR 7 ,
phenyl and phenoxy, where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1 , 2, 3, 4 or 5 radicals R10, it being possible that two R7 present on one carbon atom may together form =NOR16 or =N-NR9aR9b.
In context of radical R4, the radical R7a is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)ethyl or heptafluoroisopropyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, C3-C6-cycloalkyl-Ci-C4-alkyl, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals R10, which are as defined herein or preferably selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), C1-C4- alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbonyl and di-(Ci-C4-alkyl)aminocarbonyl and in particular from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy. In context of radical R4, the radical R8 is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 - (trifluoromethyl)ethyl or heptafluoroisopropyl, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2- butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl, NH2-C(0), C1-C4- alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4- alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N- ethylaminocarbonyl and the like, phenyl, benzyl, phenylcarbonyl, phenoxycarbonyl and phenylaminocarbonyl, where the phenyl ring in the last five radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In context of radical R4, the radical R8a is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 - (trifluoromethyl)ethyl or heptafluoroisopropyl, phenyl which is unsubstitued or substituted by 1 , 2, 3 or 4 identical or different radicals R10, which are as defined herein or preferably selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbonyl and di-(Ci-C4-alkyl)aminocarbonyl and in particular from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1-difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In context of radical R4, the radicals R9a and R9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10, which are as defined herein or preferably selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), C1-C4- alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbonyl and di-(Ci-C4-alkyl)aminocarbonyl and in particular from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In this context, NR9aR9b may preferably also be a saturated N-bound 3-, 4-, 5- or 6- membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6- membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from C1-C4- alkyl and Ci-C4-haloalkyl. Examples of such radicals NR9aR9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, N-methyl-N- ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N-methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N-isobutylamino, 1 -pyrrolidinyl, 1 - piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4-morpholinyl.
In context of radical R4, the radical R10 is as defined herein and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci- C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n- propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, such as methylthio or ethylthio, C1-C4- alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylthio, such as
fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1 ,1 -difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, Ci-C4-haloalkylsulfonyl, such as
fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, SO2NH2, C1-C4- alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4- alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N- ethylaminocarbonyl and the like. In context of radical R4, the radical R15 is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2, 2-difluoro-1 -methylethyl, 2, 2, 2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)ethyl or heptafluoroisopropyl, phenyl which is unsubstitued or substituted by 1 , 2, 3 or 4 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, Ci-C4-haloalkoxy, in particular Ci- C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylthio, such as methylthio or ethylthio, Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylthio, such as fluoromethylthio, difluoromethylthio, tnfluoromethylthio, 1 ,1 -difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, Ci-C4-haloalkylsulfonyl, such as
fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino,
diethylamino, N-methyl-N-ethylamino and the like.
In context of radical R4, the radical R16 is in particular selected from the group consisting of Ci-C4-alkyl,C2-C4-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated, and benzyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n- butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2, 2-difluoro-1 -methylethyl, 2, 2, 2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)ethyl or heptafluoroisopropyl, phenyl which is unsubstitued or substituted by 1 , 2, 3 or 4 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, Ci-C4-haloalkoxy, in particular Ci- C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylthio, such as methylthio or ethylthio, Ci-C4-alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylthio, such as fluoromethylthio, difluoromethylthio, tnfluoromethylthio, 1 ,1 -difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, Ci-C4-haloalkylsulfonyl, such as
fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino, diethylamino, N-methyl-N-ethylamino, (Ci-C4-alkyl)carbonyl, such as acetyl or propionyl, (C1-C4- alkyl)carbonyloxy, such as acetoxy or propionoxy, and (Ci-C4-alkoxy)carbonyl such as methoxycarbonyl or ethoxycarbonyl.
In context of radical R4, the radicals R17a and R17b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, phenyl or benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2, 3 or 4 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as
fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylthio, such as methylthio or ethylthio, C1-C4- alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl, Ci-C4-haloalkylthio, such as
fluoromethylthio, difluoromethylthio, trifluoromethylthio, 1 ,1 -difluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio or 2,2,2-trifluoroethylthio, Ci-C4-haloalkylsulfonyl, such as
fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, 1 ,1 -difluoroethylsulfonyl, 2- fluoroethylsulfonyl, 2,2-difluoroethylsulfonyl or 2,2,2-trifluoroethylsulfonyl, Ci-C4-alkylamino, such as methylamino or ethylamino, di-(Ci-C4-alkyl)amino, such as dimethylamino,
diethylamino, N-methyl-N-ethylamino and the like.
In context of radical S(0)nR8a, the variable n, irrespectively of its occurrence, is in particular 0 or 2.
In the context of groups (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (2a), (2b), (2c), (2d), (2e), (2f),
(3a), (3b), (3c), (3d), (3e) and (3f) of embodiments the variables R7a, R8, R8a, R15, R17a, R17b, irrespectively of their occurrence, have especially one of the following meanings:
R7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-
C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, , where the phenyl ring in the last two mentioned radicals is unsbustituted or carries 1 , 2, 3 or 4 radicals R10, phenylcarbonyl, phenoxycarbonyl and
phenylaminocarbonyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; R8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R10 is selected from the group consisting of halogen, CN, OH , SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl
two R10 present on one carbon atom may together form =NOR16;
R15 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2 3 or 4 radicals selected from halogen, OH, CN, N02, d-Ce-alkyl, Ci-C6-haloalkyl, d-C6-alkoxy, Ci-C6 haloalkoxy, (Ci-C6- alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl;
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substitutents is unsubstituted or carries 1 , 2 3 or 4 radicals selected from halogen, OH , CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl.
In the context of groups (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (2a), (2b), (2c), (2d), (2e), (2f),
(3a), (3b), (3c), (3d), (3e) and (3f) of embodiments the variables R7a, R8, R8a, R15, R17a, R17b, irrespectively of their occurrence, have especially one of the following meanings:
R7a is selected from the group consisting of Ci-C4-alkyl or Ci-C4-haloalkyl;
R8 is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;
R8a is selected from the group consisting of Ci-C4-alkyl and Ci-C4-haloalkyl;
R9a is selected from the group consisting of hydrogen and Ci-C4-alkyl;
R9b is selected from the group consisting of hydrogen and Ci-C4-alkyl;
R10 is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, C1-C4- haloalkylthio and Ci-C4-haloalkylsulfonyl;
R15 is selected from the group consisting of hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl; R16a is selected from the group consisting of Ci-C4-alkyl, which is unsubstituted, partly or completely halogenated;
R17a, R17b are each independently from one another selected from the group consisting of hydrogen and Ci-C4-alkyl.
In groups (3), (4) and (5) of embodiments, R5a is as defined above and preferably selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C2-C6-alkenyl, in particular C2-C4-alkyl, such as 2- propenyl, Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, Cs-Cs-cycloalkyl, such as cyclopropyl, cyclopbutyl, cyclopentyl or cyclohexyl, C3- C8-cycloalkyl-Ci-C4-alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alkyl, alkenyl, cycloalkyi and cycloalkylalkyi are unsubstituted, partly or completely halogenated, C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl and phenyl-Ci-C4-alkyl, in particular phenyl and benzyl, where the phenyl ring in the last four mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10.
In groups (4) and (5) of embodiments, R5b is in particular selected from the group consisting of Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C2-C6-alkenyl, in particular C2-C4-alkyl, such as 2-propenyl, Cs-Cs-cycloalkyl, such as cyclopropyl, cyclopbutyl, cyclopentyl or cyclohexyl, C3-C8-cycloalkyl-Ci-C4-alkyl, in particular C3- C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutyl methyl, wherein alkyl, alkenyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, where the radical R10 is as defined above and in particular selected from the group consisting of halogen, such as chlorine or fluorine, CN, OH, SH, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C4- alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, C1-C4- alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl,
isopropoxycarbonyl, n-butoxycarbonyl, 2-butoxycarbonyl, isobutoxycarbonyl or tert.- butoxycarbonyl, NH2-C(0), Ci-C4-alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, such as dimethylaminocarbonyl,
diethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl and the like.
In groups (3), (4) and (5) of embodiments, R5a is in particular selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, C3-C8-cycloalkyl-Ci-C4-alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alkyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
C(=0)OR8, C(=0)R7a and C(=S)R7a.
In groups (3), (4) and (5) of embodiments, R5a is especially selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl and Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy..
In groups (3), (4) and (5) of embodiments, R5a is especially hydrogen, OH, methyl or methoxy.
In context of radical R5a, the radical R7a is as defined above and in particular selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2-fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 -(trifluoromethyl)ethyl or heptafluoroisopropyl, C3-C6-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, C3-C6-cycloalkyl-Ci-C4-alkyl, such as cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals R10, which are as defined above or preferably selected from the group consisting of halogen, such as chlorine or fluorine, CN , Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
In context of radical R5a, the radical R8 is as defined above and in particular selected from the group consisting of Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl or tert-butyl, Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl, pentafluoroethyl, 2- fluoro-1 -methylethyl, 2,2-difluoro-1 -methylethyl, 2,2,2-trifluoro-1 -methylethyl, 2,2,2-trifluoro-1 - (trifluoromethyl)ethyl or heptafluoroisopropyl, Ci-C4-alkylcarbonyl, such as acetyl or propionyl, Ci-C4-haloalkylcarbonyl, such as difluoroacetyl or trifluoroacetyl, Ci-C4-alkoxycarbonyl, such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, 2- butoxycarbonyl, isobutoxycarbonyl or tert.-butoxycarbonyl, NH2-C(0), C1-C4- alkylaminocarbonyl, such as methylaminocarbonyl or ethylaminocarbonyl, di-(Ci-C4- alkyl)aminocarbonyl, such as dimethylaminocarbonyl, diethylaminocarbonyl, N-methyl-N- ethylaminocarbonyl and the like, phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN , Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, phenylcarbonyl, phenoxycarbonyl and phenylaminocarbonyl, where the phenyl ring in the last three mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6- alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl.
In groups (2) of embodiments, R4 and R5a together may also form a bivalent radical, as defined above, which is in particular selected from the group consisting of linear C2-C4- alkanediyl, i.e. CH2CH2, CH2CH2CH2 or CH2CH2CH2CH2 and linear C2-C4-alkenediyl, such as CH=CH, CH=CH-CH2 or CH2CH=CH-CH2 wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b, which is as defined above and in particular selected from the group consisting of halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C6-alkylthio, in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
isobutylsulfanyl, and Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
In groups (4) and (5) of embodiments, R5a and R5b together may also form a bivalent radical, as defined above, which is in particular selected from the group consisting of linear C2- C4-alkanediyl, i.e. CH2CH2, CH2CH2CH2 or CH2CH2CH2CH2 and linear C2-C -alkenediyl, such as CH=CH, CH=CH-CH2 or CH2CH=CH-CH2 wherein the carbon atom in the four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b, which is as defined above and in particular selected from the group consisting of halogen, such as fluorine or chlorine, C1-C6- alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy,
difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy, Ci-C6-alkylthio, in particular Ci-C4-alkylthio, such as methylsulfanly, ethylsulfanyl, n-propylsulfanyl, isopropylsulfanyl, n-butylsulfanyl, 2-butylsulfanyl or
isobutylsulfanyl, and Ci-C6-haloalkylthio in particular Ci-C2-haloalkylthio, such as
fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, 1 ,1 -difluoroethylsulfanyl, 2- fluoroethylsulfanyl, 2,2-difluoroethylsulfanyl or 2,2,2-trifluoroethylsulfanyl.
Particular preference is given to groups (1 ) of embodiments, where the radical R4 is a radical as defined in groups (1 a), (1 b), (1 c), (1 d), (1 e) and (1f) embodiments;
and where X is O.
Particular preference is also given to groups (3) of embodiments, where the radical R4 is a radical as defined in groups (3a), (3b), (3c), (3d), (3e) and (3f) embodiments;
R5a is in particular selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy, C3-C8- cycloalkyl-Ci-C4-alkyl, in particular C3-C6-cycloalkylmethyl, such as cyclopropylmethyl or cyclobutylmethyl, wherein alkyl, cycloalkyl and cycloalkylalkyl are unsubstituted, partly or completely halogenated,
C(=0)OR8, C(=0)R7a and C(=S)R7a; and where R5a is more particularly selected from the group consisting of hydrogen, OH, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl and Ci-C6-alkoxy, in particular Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropyloxy; and where R5a is especially hydrogen, OH, methyl or methoxy. and where X is O.
Particularly preferred are compounds of the formula (I) , in particular the compounds of groups (1 ), (2), (3), (4), (5), (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (2a), (2b), (2c), (2d), (2e), (21), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein
Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are independently from each other selected from the group consisting of
hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl,
difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl, or wherein R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5-membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl; and wherein R1 and R2 are more particularly independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q1 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3; and
R3b is a C-bound radical, in particular
- Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3.
Particularly preferred are also compounds of the formula (I), in particular the compounds of groups (1 ), (2), (3), (4), (5), (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (2a), (2b), (2c), (2d), (2e), (21), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein
Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are independently from each other selected from the group consisting of
hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or C1-C3- haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl. In this context, R7 is as defined above and in particular from the group consisting of N02, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, Ci-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of N02, cyclopropyl, CN and Ci-C4-alkoxy; and
R3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R7, which are identical or different. In this context, the radicals R7 are as defined above and in particular from the group consisting of N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4- alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of N02, cyclopropyl, CN and Ci-C4-alkoxy.
Particularly preferred are also compounds of the formula (I), in particular the compounds of groups (1 ), (2), (3), (4), (5), (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (2a), (2b), (2c), (2d), (2e), (21), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R7, or C3-C6-cycloalkyl, especially cyclopropyl, where R7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
R3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl,
CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2;
and
R3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
Especially preferred are compounds of the formula (I) of groups (3), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein
Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are independently from each other selected from the group consisting of
hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3-C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl,
difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, or C3-C6-halocycloalkyl such as 1 -fluorocyclopropyl or 2,2- difluorocyclopropyl, or wherein R1 and R2 form, together with the carbon atom, which they attached to, a 3- to 5 membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl; and wherein R1 and R2 are more particularly independently from each other selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is a C-bound radical, in particular
- Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3; and
R3b is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different
heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3.
Especially preferred are also compounds of the formula (I) of groups (3), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein
Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are independently from each other selected from the group consisting of
hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or C1-C3- haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially where R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl. In this context, R7 is as defined above and in particular from the group consisting of N02, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of N02, cyclopropyl, CN and Ci-C4-alkoxy; and
R3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R7, which are identical or different. In this context, the radicals R7 are as defined above and in particular from the group consisting of
N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, C1-C4- alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy.
Especially preferred are also compounds of the formula (I) of groups (3), (3a), (3b), (3c), (3d), (3e) and (3f) of embodiments, wherein
Het is as defined above and in particular a radical Het-1 a, Het-1 1 a or Het-24, more particularly a radical Het-1 a, especially 6-chloropyridin-3-yl or 6-(trifluoromethyl)pyridin-3-yl;
X is preferably O;
R1 and R2 are both hydrogen or R1 is methyl and R2 is hydrogen;
R3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R7, or C3-C6-cycloalkyl, especially cyclopropyl, where R7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
R3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2;
and
R3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
Apart from that, the variables R6, R7, R7a, R7b, R8, R8a, R9a, R9b, R10, R11, R12, R13, R14, R15, R16a, R17, R17a, R17b, R17c, irrespectively of their occurrence, in particular have the following meanings, if not stated otherwise:
R6 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, Ci-C4-alkyl, such as methyl or ethyl, Ci-C4-alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or trifluormethoxy, and Ci-C4-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as
difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl.
R7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C4- alkoxy, such as methoxy or ethoxy, Ci-C4-haloalkoxy, such as difluoromethoxy or
trifluormethoxy, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, more preferably from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl and Ci-C2-haloalkyl such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C3- C6-cycloalkyl such as cyclopropyl, cyclobutyl or cyclopropyl, and C3-C6-halocycloalkyl.
R7a irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R7b is preferably selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkylmethyl, and phenyl , it being possible for phenyl to be unsubstituted, partly or completely halogenated, or two radicals R7b bound the same carbon atom may be =0, =S or =CR13R14 and where R7b is more particularly fluorine, Ci-C4-alkyl, such as methyl, ethyl, propyl, isopropyl or n-butyl, Ci-C4-haloalkyl, especially Ci-C2-fluoroalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl or two radicals R7b bound the same carbon atom may be =0 or =CH2.
R8 irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
R8a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10, which are preferably selected, independently of each other from halogen, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-alkylthio, Ci-C4-haloalkyl, Ci-C4-haloalkoxy and Ci-C4-haloalkyl.
R9a and R9b irrespectively of their occurrence, are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR9aR9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR9aR9b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
R10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci- C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R11, R12 independently of their occurrence, are selected from the group consisting of Ci-
C6-alkyl, Ci-C6-alkoxy, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, or 3 identical or different radicals selected from fluorine, chlorine, Ci-C3-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C2-haloalkoxy.
R13, R14 independently of their occurrence, are selected from the group consisting of hydrogen, fluorine, chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl or n-butyl, C3-C6- cycloalkyl, such as cyclopropyl, cyclobutyl or cyclopentyl, and phenyl.
R15 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R16a irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci- C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n- propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy or 2,2,2-trifluoroethoxy.
R17 irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C4-haloalkyl, Ci-C6-alkoxy, Ci-C4-haloalkoxy, C3-C6-alkenyl, C3-C6- cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN , Ci-C4-alkyl, such as methyl, ethyl, n- propyl and isopropyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2- trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and C1-C4- haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluoromethoxy, difluoromethoxy,
trifluoromethoxy, 1 ,1 -difluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
R17a and R17b irrespectively of their occurrence, are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl or isobutyl, and Ci-C4-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or NR17aR17b may also be a saturated N-bound 3-, 4-, 5- or 6-membered heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C4-alkyl and Ci-C4-haloalkyl. Examples of such radicals NR17aR17b include, but are not limited to methylamino, ethylamino, n-propylamino, isopropylamino, n- butylamino, 2-butylamino, isobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-n- butylamino, N-methyl-N-ethylamino, N-methyl-N-propylamino, N-methyl-N-n-propylamino, N- methyl-N-isopropylamino, N-methyl-N-n-butylamino, N-methyl-N-2-butylamino, N-methyl-N- isobutylamino, 1 -pyrrolidinyl, 1 -piperidinyl, 1 -piperazinly, 4-methyl-1 -piperazinly and 4- morpholinyl.
R17c irrespectively of its occurrence, is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstitued or substituted by 1 , 2 or 3 identical or different radicals selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 - difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 ,1 -difluoroethoxy, 2- fluoroethoxy, 2,2-difluoroethoxy or 2,2,2-trifluoroethoxy.
Particular preference is given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I-A.4, I-B.1 , I-B.2, I-C.1 , I-C.2, to their tautomers, to their stereoisomers and to their salts, where R1 , R3a, R3b and R4 are as defined above, in particular to those compounds, where
X is O or S, especially O;
R1 is selected from the group consisting of hydrogen, halogen, such as fluorine or chlorine, CN, Ci-C6-alkyl, in particular Ci-C4-alkyl, such as methyl, ethyl, n-propyl or isopropyl, C3- C6-cycloalkyl, such as cyclopropyl or cyclobutyl, Ci-C6-haloalkyl, in particular C1-C2- haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, or C3-C6-halocycloalkyl such as 1 - fluorocyclopropyl or 2,2-difluorocyclopropyl,
in particular hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2- fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl,; R3a is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, Q1 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3; R3b is a C-bound radical, in particular
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted carries any combination of 1 , 2, 3, 4 or 5 radicals R10, or
- Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl, in particular CH2, CH2CH2 or CHCH3; R4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
and
R5a if present, is selected from H, Ci-C4-alkyl, OH and Ci-C4-alkoxy.
Particular preference is also given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I- A.4, I-B.1 , I-B.2, I-C.1 , I-C.2, to their tautomers, to their stereoisomers and to their salts, where R1, R3a, R3b and R4 are as defined below:
X is O or S, especially O;
R1 is selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl ethyl or isopropyl, or Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1 -difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl and especially hydrogen or methyl;
R3a is Ci-C6-alkyl, especially Ci-C3-alkyl, which is unsubstituted, partly or completely
halogenated and/or carries any combination of 1 , 2 or 3 radicals R7, or C3-C6-cycloalkyl, especially cyclopropyl, where C3-C6-cycloalkyl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl. In this context, R7 is as defined above and in particular from the group consisting of NO2, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, =N-0-Ci-C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy;
R3b is Ci-C6-alkyl or Ci-C6-haloalkyl, especially Ci-C3-alkyl or Ci-C3-haloalkyl, where alkyl and haloalkyl may carry 1 , 2 or 3 further radicals R7, which are identical or different. In this context, the radicals R7 are as defined above and in particular from the group consisting of N02, CN, Cs-Ce-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci-C4-alkyl, C1-C4- alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated, and R7 is especially selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy, and
R4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
and
R5a if present, is selected from H , Ci-C4-alkyl, OH and Ci-C4-alkoxy.
Particular preference is also given to the compounds of the formulae I-A.1 , I-A.2, I-A.3, I- A.4, I-B.1 , I-B.2, I-C.1 , I-C.2, to their tautomers, to their stereoisomers and to their salts, where R1, R3a, R3b and R4 are as defined below:
X is O or S, especially O;
R1 is hydrogen or methyl and especially hydrogen;
R3a is Ci-C3-alkyl, which is unsubstituted, partly or completely halogenated and/or carries a radical R7, or C3-C6-cycloalkyl, especially cyclopropyl, where R7 is as defined above and in particular selected from the group consisting of NO2, cyclopropyl, CN and Ci-C4-alkoxy and where
R3a is especially selected from the group consisting of methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2N02;
and
R3b is selected from the group consisting of Ci-C3-alkyl and Ci-C3-haloalkyl, especially from the group consisting of methyl, ethyl, difluoromethyl and trifluoromethyl.
R4 is a radical as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d), (1 e), (1f), (3a), (3b), (3c), (3d), (3e) or (3f);
and
R5a if present, is selected from H , Ci-C4-alkyl, OH and Ci-C4-alkoxy.
Figure imgf000073_0001
Figure imgf000073_0002
Figure imgf000073_0003
Figure imgf000073_0004
I-B.2 I-C.2 A special group of embodiments relates to the compounds of formula (I-A.1 ), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- A.1 ), their tautomers, their stereoisomers and their salts, where R1 is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-A.2), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.2), their tautomers, their stereoisomers and their salts, where R1 is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-B.1 ), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.1 ), their tautomers, their stereoisomers and their salts, where R1 is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-C.1 ), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
C.1 ), their tautomers, their stereoisomers and their salts, where R1 is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- C.1 ), their tautomers, their stereoisomers and their salts, where R1 is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-A.3), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, R5a is H, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.3), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-A.4), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, R5a is H, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- A.4), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
A.4), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-B.2), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, R5a is H, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- B.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
B.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
A further special group of embodiments relates to the compounds of formula (I-C.2), to their tautomers, to their stereoisomers and to their salts, where R1 is hydrogen, R5a is H, X is O, and where R3a, R3b and R4 are as defined in lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is H, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is CH3, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I-
C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OH, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCH3, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B. Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCHs, X is O, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is H, R5a is OCHs, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Further examples of this special group of embodiments are the compounds of formula (I- C.2), their tautomers, their stereoisomers and their salts, where R1 is CH3, R5a is OCHs, X is S, and where R3a, R3b and R4 have one of the meanings given in any of lines 1 to 972 of the following table B.
Table B: R3a R3b R4
R3a R3b R4 26 CHs CHs R-41 .8
1 CHs CHs R-4.1 27 CHs CHs R-43.1
2 CHs CHs R-4.2 28 CHs CHs R-43.2
3 CHs CHs R-4.3 29 CHs CHs R-43.3
4 CHs CHs R-4.4 30 CHs CHs R-43.4
5 CHs CHs R-4.5 31 CHs CHs R-43.5
6 CHs CHs R-4.6 32 CHs CHs R-43.6
7 CHs CHs R-4.7 33 CHs CHs R-43.7
8 CHs CHs R-4.8 34 CHs CHs R-43.8
9 CHs CHs R-4.9 35 CHs CHs R-43.9
10 CHs CHs R-4.10 36 CHs CHs R-43.10
1 1 CHs CHs R-4.1 1 37 CHs CHs R-43.1 1
12 CHs CHs R-4.12 38 CHs CHs R-43.12
13 CHs CHs R-4.13 39 CHs CHs R-43.13
14 CHs CHs R-4.14 40 CHs CHs R-43.14
15 CHs CHs R-4.15 41 CHs CHs R-43.15
16 CHs CHs R-4.16 42 CHs CHs R-43.16
17 CHs CHs R-4.17 43 CHs CHs R-43.17
18 CHs CHs R-4.18 44 CHs CHs R-43.18
19 CHs CHs R-41 .1 45 CHs CHs R-43.19
20 CHs CHs R-41 .2 46 CHs CHs R-43.20
21 CHs CHs R-41 .3 47 CHs CHs R-43.21
22 CHs CHs R-41 .4 48 CHs CHs R-43.22
23 CHs CHs R-41 .5 49 CHs CHs R-43.23
24 CHs CHs R-41 .6 50 CHs CHs R-43.24
25 CHs CHs R-41 .7 51 CHs CHs R-43.25 R3a R3b R4 R3a R3b R4
CHs CHs R-43.26 91 C2H5 CHs R-4.10
CHs CHs R-43.27 92 C2H5 CHs R-4.1 1
CHs CHs R-43.28 93 C2H5 CHs R-4.12
CHs CHs R-43.29 94 C2H5 CHs R-4.13
CHs CHs R-43.30 95 C2H5 CHs R-4.14
CHs CHs R-43.31 96 C2H5 CHs R-4.15
CHs CHs R-43.32 97 C2H5 CHs R-4.16
CHs CHs R-43.33 98 C2H5 CHs R-4.17
CHs CHs R-43.34 99 C2H5 CHs R-4.18
CHs CHs R-43.35 100 C2H5 CHs R-41 .1
CHs CHs R-43.36 101 C2H5 CHs R-41 .2
CHs CHs R-43.37 102 C2H5 CHs R-41 .3
CHs CHs R-43.38 103 C2H5 CHs R-41 .4
CHs CHs R-43.39 104 C2H5 CHs R-41 .5
CHs CHs R-43.40 105 C2H5 CHs R-41 .6
CHs CHs R-43.41 106 C2H5 CHs R-41 .7
CHs CHs R-43.42 107 C2H5 CHs R-41 .8
CHs CHs R-43.43 108 C2H5 CHs R-43.1
CHs CHs R-43.44 109 C2H5 CHs R-43.2
CHs CHs R-44.1 1 10 C2H5 CHs R-43.3
CHs CHs R-44.2 1 1 1 C2H5 CHs R-43.4
CHs CHs R-44.3 1 12 C2H5 CHs R-43.5
CHs CHs R-44.4 1 13 C2H5 CHs R-43.6
CHs CHs R-44.5 1 14 C2H5 CHs R-43.7
CHs CHs R-44.6 1 15 C2H5 CHs R-43.8
CHs CHs R-44.7 1 16 C2H5 CHs R-43.9
CHs CHs R-44.8 1 17 C2H5 CHs R-43.10
CHs CHs R-44.9 1 18 C2H5 CHs R-43.1 1
CHs CHs R-44.10 1 19 C2H5 CHs R-43.12
CHs CHs R-45.6 120 C2H5 CHs R-43.13
C2H5 CHs R-4.1 121 C2H5 CHs R-43.14
C2H5 CHs R-4.2 122 C2H5 CHs R-43.15
C2H5 CHs R-4.3 123 C2H5 CHs R-43.16
C2H5 CHs R-4.4 124 C2H5 CHs R-43.17
C2H5 CHs R-4.5 125 C2H5 CHs R-43.18
C2H5 CHs R-4.6 126 C2H5 CHs R-43.19
C2H5 CHs R-4.7 127 C2H5 CHs R-43.20
C2H5 CHs R-4.8 128 C2H5 CHs R-43.21
C2H5 CHs R-4.9 129 C2H5 CHs R-43.22 R3a R3b R4 R3a R3b R4
130 C2H5 CHs R-43.23 169 CH2CHF2 CHs R-4.7
131 C2H5 CHs R-43.24 170 CH2CHF2 CHs R-4.8
132 C2H5 CHs R-43.25 171 CH2CHF2 CHs R-4.9
133 C2H5 CHs R-43.26 172 CH2CHF2 CHs R-4.10
134 C2H5 CHs R-43.27 173 CH2CHF2 CHs R-4.1 1
135 C2H5 CHs R-43.28 174 CH2CHF2 CHs R-4.12
136 C2H5 CHs R-43.29 175 CH2CHF2 CHs R-4.13
137 C2H5 CHs R-43.30 176 CH2CHF2 CHs R-4.14
138 C2H5 CHs R-43.31 177 CH2CHF2 CHs R-4.15
139 C2H5 CHs R-43.32 178 CH2CHF2 CHs R-4.16
140 C2H5 CHs R-43.33 179 CH2CHF2 CHs R-4.17
141 C2H5 CHs R-43.34 180 CH2CHF2 CHs R-4.18
142 C2H5 CHs R-43.35 181 CH2CHF2 CHs R-41 .1
143 C2H5 CHs R-43.36 182 CH2CHF2 CHs R-41 .2
144 C2H5 CHs R-43.37 183 CH2CHF2 CHs R-41 .3
145 C2H5 CHs R-43.38 184 CH2CHF2 CHs R-41 .4
146 C2H5 CHs R-43.39 185 CH2CHF2 CHs R-41 .5
147 C2H5 CHs R-43.40 186 CH2CHF2 CHs R-41 .6
148 C2H5 CHs R-43.41 187 CH2CHF2 CHs R-41 .7
149 C2H5 CHs R-43.42 188 CH2CHF2 CHs R-41 .8
150 C2H5 CHs R-43.43 189 CH2CHF2 CHs R-43.1
151 C2H5 CHs R-43.44 190 CH2CHF2 CHs R-43.2
152 C2H5 CHs R-44.1 191 CH2CHF2 CHs R-43.3
153 C2H5 CHs R-44.2 192 CH2CHF2 CHs R-43.4
154 C2H5 CHs R-44.3 193 CH2CHF2 CHs R-43.5
155 C2H5 CHs R-44.4 194 CH2CHF2 CHs R-43.6
156 C2H5 CHs R-44.5 195 CH2CHF2 CHs R-43.7
157 C2H5 CHs R-44.6 196 CH2CHF2 CHs R-43.8
158 C2H5 CHs R-44.7 197 CH2CHF2 CHs R-43.9
159 C2H5 CHs R-44.8 198 CH2CHF2 CHs R-43.10
160 C2H5 CHs R-44.9 199 CH2CHF2 CHs R-43.1 1
161 C2H5 CHs R-44.10 200 CH2CHF2 CHs R-43.12
162 C2H5 CHs R-45.6 201 CH2CHF2 CHs R-43.13
163 CH2CHF2 CHs R-4.1 202 CH2CHF2 CHs R-43.14
164 CH2CHF2 CHs R-4.2 203 CH2CHF2 CHs R-43.15
165 CH2CHF2 CHs R-4.3 204 CH2CHF2 CHs R-43.16
166 CH2CHF2 CHs R-4.4 205 CH2CHF2 CHs R-43.17
167 CH2CHF2 CHs R-4.5 206 CH2CHF2 CHs R-43.18
168 CH2CHF2 CHs R-4.6 207 CH2CHF2 CHs R-43.19 R3a R3b R4 R3a R3b R4
208 CH2CHF2 CH3 R-43.20 247 CH2CF3 CHs R-4.4
209 CH2CHF2 CH3 R-43.21 248 CH2CF3 CHs R-4.5
210 CH2CHF2 CH3 R-43.22 249 CH2CF3 CHs R-4.6
21 1 CH2CHF2 CH3 R-43.23 250 CH2CF3 CHs R-4.7
212 CH2CHF2 CH3 R-43.24 251 CH2CF3 CHs R-4.8
213 CH2CHF2 CH3 R-43.25 252 CH2CF3 CHs R-4.9
214 CH2CHF2 CH3 R-43.26 253 CH2CF3 CHs R-4.10
215 CH2CHF2 CH3 R-43.27 254 CH2CF3 CHs R-4.1 1
216 CH2CHF2 CH3 R-43.28 255 CH2CF3 CHs R-4.12
217 CH2CHF2 CH3 R-43.29 256 CH2CF3 CHs R-4.13
218 CH2CHF2 CH3 R-43.30 257 CH2CF3 CHs R-4.14
219 CH2CHF2 CH3 R-43.31 258 CH2CF3 CHs R-4.15
220 CH2CHF2 CH3 R-43.32 259 CH2CF3 CHs R-4.16
221 CH2CHF2 CH3 R-43.33 260 CH2CF3 CHs R-4.17
222 CH2CHF2 CH3 R-43.34 261 CH2CF3 CHs R-4.18
223 CH2CHF2 CH3 R-43.35 262 CH2CF3 CHs R-41 .1
224 CH2CHF2 CH3 R-43.36 263 CH2CF3 CHs R-41 .2
225 CH2CHF2 CH3 R-43.37 264 CH2CF3 CHs R-41 .3
226 CH2CHF2 CH3 R-43.38 265 CH2CF3 CHs R-41 .4
227 CH2CHF2 CH3 R-43.39 266 CH2CF3 CHs R-41 .5
228 CH2CHF2 CH3 R-43.40 267 CH2CF3 CHs R-41 .6
229 CH2CHF2 CH3 R-43.41 268 CH2CF3 CHs R-41 .7
230 CH2CHF2 CH3 R-43.42 269 CH2CF3 CHs R-41 .8
231 CH2CHF2 CH3 R-43.43 270 CH2CF3 CHs R-43.1
232 CH2CHF2 CH3 R-43.44 271 CH2CF3 CHs R-43.2
233 CH2CHF2 CH3 R-44.1 272 CH2CF3 CHs R-43.3
234 CH2CHF2 CH3 R-44.2 273 CH2CF3 CHs R-43.4
235 CH2CHF2 CH3 R-44.3 274 CH2CF3 CHs R-43.5
236 CH2CHF2 CH3 R-44.4 275 CH2CF3 CHs R-43.6
237 CH2CHF2 CH3 R-44.5 276 CH2CF3 CHs R-43.7
238 CH2CHF2 CH3 R-44.6 277 CH2CF3 CHs R-43.8
239 CH2CHF2 CH3 R-44.7 278 CH2CF3 CHs R-43.9
240 CH2CHF2 CH3 R-44.8 279 CH2CF3 CHs R-43.10
241 CH2CHF2 CH3 R-44.9 280 CH2CF3 CHs R-43.1 1
242 CH2CHF2 CH3 R-44.10 281 CH2CF3 CHs R-43.12
243 CH2CHF2 CH3 R-45.6 282 CH2CF3 CHs R-43.13
244 CH2CF3 CH3 R-4.1 283 CH2CF3 CHs R-43.14
245 CH2CF3 CH3 R-4.2 284 CH2CF3 CHs R-43.15
246 CH2CF3 CH3 R-4.3 285 CH2CF3 CHs R-43.16 R3a R3b R4 R3a R3b R4
286 CH2CF3 CH3 R-43.17 325 CHs CFs R-4.1
287 CH2CF3 CH3 R-43.18 326 CHs CFs R-4.2
288 CH2CF3 CH3 R-43.19 327 CHs CFs R-4.3
289 CH2CF3 CH3 R-43.20 328 CHs CFs R-4.4
290 CH2CF3 CH3 R-43.21 329 CHs CFs R-4.5
291 CH2CF3 CH3 R-43.22 330 CHs CFs R-4.6
292 CH2CF3 CH3 R-43.23 331 CHs CFs R-4.7
293 CH2CF3 CH3 R-43.24 332 CHs CFs R-4.8
294 CH2CF3 CH3 R-43.25 333 CHs CFs R-4.9
295 CH2CF3 CH3 R-43.26 334 CHs CFs R-4.10
296 CH2CF3 CH3 R-43.27 335 CHs CFs R-4.1 1
297 CH2CF3 CH3 R-43.28 336 CHs CFs R-4.12
298 CH2CF3 CH3 R-43.29 337 CHs CFs R-4.13
299 CH2CF3 CH3 R-43.30 338 CHs CFs R-4.14
300 CH2CF3 CH3 R-43.31 339 CHs CFs R-4.15
301 CH2CF3 CH3 R-43.32 340 CHs CFs R-4.16
302 CH2CF3 CH3 R-43.33 341 CHs CFs R-4.17
303 CH2CF3 CH3 R-43.34 342 CHs CFs R-4.18
304 CH2CF3 CH3 R-43.35 343 CHs CFs R-41 .1
305 CH2CF3 CH3 R-43.36 344 CHs CFs R-41 .2
306 CH2CF3 CH3 R-43.37 345 CHs CFs R-41 .3
307 CH2CF3 CH3 R-43.38 346 CHs CFs R-41 .4
308 CH2CF3 CH3 R-43.39 347 CHs CFs R-41 .5
309 CH2CF3 CH3 R-43.40 348 CHs CFs R-41 .6
310 CH2CF3 CH3 R-43.41 349 CHs CFs R-41 .7
31 1 CH2CF3 CH3 R-43.42 350 CHs CFs R-41 .8
312 CH2CF3 CH3 R-43.43 351 CHs CFs R-43.1
313 CH2CF3 CH3 R-43.44 352 CHs CFs R-43.2
314 CH2CF3 CH3 R-44.1 353 CHs CFs R-43.3
315 CH2CF3 CH3 R-44.2 354 CHs CFs R-43.4
316 CH2CF3 CH3 R-44.3 355 CHs CFs R-43.5
317 CH2CF3 CH3 R-44.4 356 CHs CFs R-43.6
318 CH2CF3 CH3 R-44.5 357 CHs CFs R-43.7
319 CH2CF3 CH3 R-44.6 358 CHs CFs R-43.8
320 CH2CF3 CH3 R-44.7 359 CHs CFs R-43.9
321 CH2CF3 CH3 R-44.8 360 CHs CFs R-43.10
322 CH2CF3 CH3 R-44.9 361 CHs CFs R-43.1 1
323 CH2CF3 CH3 R-44.10 362 CHs CFs R-43.12
324 CH2CF3 CH3 R-45.6 363 CHs CFs R-43.13 R3a R3b R4 R3a R3b R4
364 CHs CFs R-43.14 403 CHs CFs R-44.9
365 CHs CFs R-43.15 404 CHs CFs R-44.10
366 CHs CFs R-43.16 405 CHs CFs R-45.6
367 CHs CFs R-43.17 406 C2H5 CFs R-4.1
368 CHs CFs R-43.18 407 C2H5 CFs R-4.2
369 CHs CFs R-43.19 408 C2H5 CFs R-4.3
370 CHs CFs R-43.20 409 C2H5 CFs R-4.4
371 CHs CFs R-43.21 410 C2H5 CFs R-4.5
372 CHs CFs R-43.22 41 1 C2H5 CFs R-4.6
373 CHs CFs R-43.23 412 C2H5 CFs R-4.7
374 CHs CFs R-43.24 413 C2H5 CFs R-4.8
375 CHs CFs R-43.25 414 C2H5 CFs R-4.9
376 CHs CFs R-43.26 415 C2H5 CFs R-4.10
377 CHs CFs R-43.27 416 C2H5 CFs R-4.1 1
378 CHs CFs R-43.28 417 C2H5 CFs R-4.12
379 CHs CFs R-43.29 418 C2H5 CFs R-4.13
380 CHs CFs R-43.30 419 C2H5 CFs R-4.14
381 CHs CFs R-43.31 420 C2H5 CFs R-4.15
382 CHs CFs R-43.32 421 C2H5 CFs R-4.16
383 CHs CFs R-43.33 422 C2H5 CFs R-4.17
384 CHs CFs R-43.34 423 C2H5 CFs R-4.18
385 CHs CFs R-43.35 424 C2H5 CFs R-41 .1
386 CHs CFs R-43.36 425 C2H5 CFs R-41 .2
387 CHs CFs R-43.37 426 C2H5 CFs R-41 .3
388 CHs CFs R-43.38 427 C2H5 CFs R-41 .4
389 CHs CFs R-43.39 428 C2H5 CFs R-41 .5
390 CHs CFs R-43.40 429 C2H5 CFs R-41 .6
391 CHs CFs R-43.41 430 C2H5 CFs R-41 .7
392 CHs CFs R-43.42 431 C2H5 CFs R-41 .8
393 CHs CFs R-43.43 432 C2H5 CFs R-43.1
394 CHs CFs R-43.44 433 C2H5 CFs R-43.2
395 CHs CFs R-44.1 434 C2H5 CFs R-43.3
396 CHs CFs R-44.2 435 C2H5 CFs R-43.4
397 CHs CFs R-44.3 436 C2H5 CFs R-43.5
398 CHs CFs R-44.4 437 C2H5 CFs R-43.6
399 CHs CFs R-44.5 438 C2H5 CFs R-43.7
400 CHs CFs R-44.6 439 C2H5 CFs R-43.8
401 CHs CFs R-44.7 440 C2H5 CFs R-43.9
402 CHs CFs R-44.8 441 C2H5 CFs R-43.10 R3a R3b R4 R3a R3b R4
442 C2H5 CFs R-43.1 1 481 C2H5 CFs R-44.6
443 C2H5 CFs R-43.12 482 C2H5 CFs R-44.7
444 C2H5 CFs R-43.13 483 C2H5 CFs R-44.8
445 C2H5 CFs R-43.14 484 C2H5 CFs R-44.9
446 C2H5 CFs R-43.15 485 C2H5 CFs R-44.10
447 C2H5 CFs R-43.16 486 C2H5 CFs R-45.6
448 C2H5 CFs R-43.17 487 CH2CHF2 CFs R-4.1
449 C2H5 CFs R-43.18 488 CH2CHF2 CFs R-4.2
450 C2H5 CFs R-43.19 489 CH2CHF2 CFs R-4.3
451 C2H5 CFs R-43.20 490 CH2CHF2 CFs R-4.4
452 C2H5 CFs R-43.21 491 CH2CHF2 CFs R-4.5
453 C2H5 CFs R-43.22 492 CH2CHF2 CFs R-4.6
454 C2H5 CFs R-43.23 493 CH2CHF2 CFs R-4.7
455 C2H5 CFs R-43.24 494 CH2CHF2 CFs R-4.8
456 C2H5 CFs R-43.25 495 CH2CHF2 CFs R-4.9
457 C2H5 CFs R-43.26 496 CH2CHF2 CFs R-4.10
458 C2H5 CFs R-43.27 497 CH2CHF2 CFs R-4.1 1
459 C2H5 CFs R-43.28 498 CH2CHF2 CFs R-4.12
460 C2H5 CFs R-43.29 499 CH2CHF2 CFs R-4.13
461 C2H5 CFs R-43.30 500 CH2CHF2 CFs R-4.14
462 C2H5 CFs R-43.31 501 CH2CHF2 CFs R-4.15
463 C2H5 CFs R-43.32 502 CH2CHF2 CFs R-4.16
464 C2H5 CFs R-43.33 503 CH2CHF2 CFs R-4.17
465 C2H5 CFs R-43.34 504 CH2CHF2 CFs R-4.18
466 C2H5 CFs R-43.35 505 CH2CHF2 CFs R-41 .1
467 C2H5 CFs R-43.36 506 CH2CHF2 CFs R-41 .2
468 C2H5 CFs R-43.37 507 CH2CHF2 CFs R-41 .3
469 C2H5 CFs R-43.38 508 CH2CHF2 CFs R-41 .4
470 C2H5 CFs R-43.39 509 CH2CHF2 CFs R-41 .5
471 C2H5 CFs R-43.40 510 CH2CHF2 CFs R-41 .6
472 C2H5 CFs R-43.41 51 1 CH2CHF2 CFs R-41 .7
473 C2H5 CFs R-43.42 512 CH2CHF2 CFs R-41 .8
474 C2H5 CFs R-43.43 513 CH2CHF2 CFs R-43.1
475 C2H5 CFs R-43.44 514 CH2CHF2 CFs R-43.2
476 C2H5 CFs R-44.1 515 CH2CHF2 CFs R-43.3
477 C2H5 CFs R-44.2 516 CH2CHF2 CFs R-43.4
478 C2H5 CFs R-44.3 517 CH2CHF2 CFs R-43.5
479 C2H5 CFs R-44.4 518 CH2CHF2 CFs R-43.6
480 C2H5 CFs R-44.5 519 CH2CHF2 CFs R-43.7 R3a R3b R4 R3a R3b R4
520 CH2CHF2 CFs R-43.8 559 CH2CHF2 CFs R-44.3
521 CH2CHF2 CFs R-43.9 560 CH2CHF2 CFs R-44.4
522 CH2CHF2 CFs R-43.10 561 CH2CHF2 CFs R-44.5
523 CH2CHF2 CFs R-43.1 1 562 CH2CHF2 CFs R-44.6
524 CH2CHF2 CFs R-43.12 563 CH2CHF2 CFs R-44.7
525 CH2CHF2 CFs R-43.13 564 CH2CHF2 CFs R-44.8
526 CH2CHF2 CFs R-43.14 565 CH2CHF2 CFs R-44.9
527 CH2CHF2 CFs R-43.15 566 CH2CHF2 CFs R-44.10
528 CH2CHF2 CFs R-43.16 567 CH2CHF2 CFs R-45.6
529 CH2CHF2 CFs R-43.17 568 CH2CF3 CFs R-4.1
530 CH2CHF2 CFs R-43.18 569 CH2CF3 CFs R-4.2
531 CH2CHF2 CFs R-43.19 570 CH2CF3 CFs R-4.3
532 CH2CHF2 CFs R-43.20 571 CH2CF3 CFs R-4.4
533 CH2CHF2 CFs R-43.21 572 CH2CF3 CFs R-4.5
534 CH2CHF2 CFs R-43.22 573 CH2CF3 CFs R-4.6
535 CH2CHF2 CFs R-43.23 574 CH2CF3 CFs R-4.7
536 CH2CHF2 CFs R-43.24 575 CH2CF3 CFs R-4.8
537 CH2CHF2 CFs R-43.25 576 CH2CF3 CFs R-4.9
538 CH2CHF2 CFs R-43.26 577 CH2CF3 CFs R-4.10
539 CH2CHF2 CFs R-43.27 578 CH2CF3 CFs R-4.1 1
540 CH2CHF2 CFs R-43.28 579 CH2CF3 CFs R-4.12
541 CH2CHF2 CFs R-43.29 580 CH2CF3 CFs R-4.13
542 CH2CHF2 CFs R-43.30 581 CH2CF3 CFs R-4.14
543 CH2CHF2 CFs R-43.31 582 CH2CF3 CFs R-4.15
544 CH2CHF2 CFs R-43.32 583 CH2CF3 CFs R-4.16
545 CH2CHF2 CFs R-43.33 584 CH2CF3 CFs R-4.17
546 CH2CHF2 CFs R-43.34 585 CH2CF3 CFs R-4.18
547 CH2CHF2 CFs R-43.35 586 CH2CF3 CFs R-41 .1
548 CH2CHF2 CFs R-43.36 587 CH2CF3 CFs R-41 .2
549 CH2CHF2 CFs R-43.37 588 CH2CF3 CFs R-41 .3
550 CH2CHF2 CFs R-43.38 589 CH2CF3 CFs R-41 .4
551 CH2CHF2 CFs R-43.39 590 CH2CF3 CFs R-41 .5
552 CH2CHF2 CFs R-43.40 591 CH2CF3 CFs R-41 .6
553 CH2CHF2 CFs R-43.41 592 CH2CF3 CFs R-41 .7
554 CH2CHF2 CFs R-43.42 593 CH2CF3 CFs R-41 .8
555 CH2CHF2 CFs R-43.43 594 CH2CF3 CFs R-43.1
556 CH2CHF2 CFs R-43.44 595 CH2CF3 CFs R-43.2
557 CH2CHF2 CFs R-44.1 596 CH2CF3 CFs R-43.3
558 CH2CHF2 CFs R-44.2 597 CH2CF3 CFs R-43.4 R3a R3b R4 R3a R3b R4
598 CH2CF3 CF3 R-43.5 637 CH2CF3 CF3 R-43.44
599 CH2CF3 CF3 R-43.6 638 CH2CF3 CF3 R-44.1
600 CH2CF3 CF3 R-43.7 639 CH2CF3 CF3 R-44.2
601 CH2CF3 CF3 R-43.8 640 CH2CF3 CF3 R-44.3
602 CH2CF3 CF3 R-43.9 641 CH2CF3 CF3 R-44.4
603 CH2CF3 CF3 R-43.10 642 CH2CF3 CF3 R-44.5
604 CH2CF3 CF3 R-43.1 1 643 CH2CF3 CF3 R-44.6
605 CH2CF3 CF3 R-43.12 644 CH2CF3 CF3 R-44.7
606 CH2CF3 CF3 R-43.13 645 CH2CF3 CF3 R-44.8
607 CH2CF3 CF3 R-43.14 646 CH2CF3 CF3 R-44.9
608 CH2CF3 CF3 R-43.15 647 CH2CF3 CF3 R-44.10
609 CH2CF3 CF3 R-43.16 648 CH2CF3 CF3 R-45.6
610 CH2CF3 CF3 R-43.17 649 CH3 CHF2 R-4.1
61 1 CH2CF3 CF3 R-43.18 650 CH3 CHF2 R-4.2
612 CH2CF3 CF3 R-43.19 651 CH3 CHF2 R-4.3
613 CH2CF3 CF3 R-43.20 652 CH3 CHF2 R-4.4
614 CH2CF3 CF3 R-43.21 653 CH3 CHF2 R-4.5
615 CH2CF3 CF3 R-43.22 654 CH3 CHF2 R-4.6
616 CH2CF3 CF3 R-43.23 655 CH3 CHF2 R-4.7
617 CH2CF3 CF3 R-43.24 656 CH3 CHF2 R-4.8
618 CH2CF3 CF3 R-43.25 657 CH3 CHF2 R-4.9
619 CH2CF3 CF3 R-43.26 658 CH3 CHF2 R-4.10
620 CH2CF3 CF3 R-43.27 659 CH3 CHF2 R-4.1 1
621 CH2CF3 CF3 R-43.28 660 CH3 CHF2 R-4.12
622 CH2CF3 CF3 R-43.29 661 CH3 CHF2 R-4.13
623 CH2CF3 CF3 R-43.30 662 CH3 CHF2 R-4.14
624 CH2CF3 CF3 R-43.31 663 CH3 CHF2 R-4.15
625 CH2CF3 CF3 R-43.32 664 CH3 CHF2 R-4.16
626 CH2CF3 CF3 R-43.33 665 CH3 CHF2 R-4.17
627 CH2CF3 CF3 R-43.34 666 CH3 CHF2 R-4.18
628 CH2CF3 CF3 R-43.35 667 CH3 CHF2 R-41 .1
629 CH2CF3 CF3 R-43.36 668 CH3 CHF2 R-41 .2
630 CH2CF3 CF3 R-43.37 669 CH3 CHF2 R-41 .3
631 CH2CF3 CF3 R-43.38 670 CH3 CHF2 R-41 .4
632 CH2CF3 CF3 R-43.39 671 CH3 CHF2 R-41 .5
633 CH2CF3 CF3 R-43.40 672 CH3 CHF2 R-41 .6
634 CH2CF3 CF3 R-43.41 673 CH3 CHF2 R-41 .7
635 CH2CF3 CF3 R-43.42 674 CH3 CHF2 R-41 .8
636 CH2CF3 CF3 R-43.43 675 CH3 CHF2 R-43.1 R3a R3b R4 R3a R3b R4
676 CHs CHF2 R-43.2 715 CHs CHF2 R-43.41
677 CHs CHF2 R-43.3 716 CHs CHF2 R-43.42
678 CHs CHF2 R-43.4 717 CHs CHF2 R-43.43
679 CHs CHF2 R-43.5 718 CHs CHF2 R-43.44
680 CHs CHF2 R-43.6 719 CHs CHF2 R-44.1
681 CHs CHF2 R-43.7 720 CHs CHF2 R-44.2
682 CHs CHF2 R-43.8 721 CHs CHF2 R-44.3
683 CHs CHF2 R-43.9 722 CHs CHF2 R-44.4
684 CHs CHF2 R-43.10 723 CHs CHF2 R-44.5
685 CHs CHF2 R-43.1 1 724 CHs CHF2 R-44.6
686 CHs CHF2 R-43.12 725 CHs CHF2 R-44.7
687 CHs CHF2 R-43.13 726 CHs CHF2 R-44.8
688 CHs CHF2 R-43.14 727 CHs CHF2 R-44.9
689 CHs CHF2 R-43.15 728 CHs CHF2 R-44.10
690 CHs CHF2 R-43.16 729 CHs CHF2 R-45.6
691 CHs CHF2 R-43.17 730 C2H5 CHF2 R-4.1
692 CHs CHF2 R-43.18 731 C2H5 CHF2 R-4.2
693 CHs CHF2 R-43.19 732 C2H5 CHF2 R-4.3
694 CHs CHF2 R-43.20 733 C2H5 CHF2 R-4.4
695 CHs CHF2 R-43.21 734 C2H5 CHF2 R-4.5
696 CHs CHF2 R-43.22 735 C2H5 CHF2 R-4.6
697 CHs CHF2 R-43.23 736 C2H5 CHF2 R-4.7
698 CHs CHF2 R-43.24 737 C2H5 CHF2 R-4.8
699 CHs CHF2 R-43.25 738 C2H5 CHF2 R-4.9
700 CHs CHF2 R-43.26 739 C2H5 CHF2 R-4.10
701 CHs CHF2 R-43.27 740 C2H5 CHF2 R-4.1 1
702 CHs CHF2 R-43.28 741 C2H5 CHF2 R-4.12
703 CHs CHF2 R-43.29 742 C2H5 CHF2 R-4.13
704 CHs CHF2 R-43.30 743 C2H5 CHF2 R-4.14
705 CHs CHF2 R-43.31 744 C2H5 CHF2 R-4.15
706 CHs CHF2 R-43.32 745 C2H5 CHF2 R-4.16
707 CHs CHF2 R-43.33 746 C2H5 CHF2 R-4.17
708 CHs CHF2 R-43.34 747 C2H5 CHF2 R-4.18
709 CHs CHF2 R-43.35 748 C2H5 CHF2 R-41 .1
710 CHs CHF2 R-43.36 749 C2H5 CHF2 R-41 .2
71 1 CHs CHF2 R-43.37 750 C2H5 CHF2 R-41 .3
712 CHs CHF2 R-43.38 751 C2H5 CHF2 R-41 .4
713 CHs CHF2 R-43.39 752 C2H5 CHF2 R-41 .5
714 CHs CHF2 R-43.40 753 C2H5 CHF2 R-41 .6 R3a R3b R4 R3a R3b R4
754 C2H5 CHF2 R-41 .7 793 C2H5 CHF2 R-43.38
755 C2H5 CHF2 R-41 .8 794 C2H5 CHF2 R-43.39
756 C2H5 CHF2 R-43.1 795 C2H5 CHF2 R-43.40
757 C2H5 CHF2 R-43.2 796 C2H5 CHF2 R-43.41
758 C2H5 CHF2 R-43.3 797 C2H5 CHF2 R-43.42
759 C2H5 CHF2 R-43.4 798 C2H5 CHF2 R-43.43
760 C2H5 CHF2 R-43.5 799 C2H5 CHF2 R-43.44
761 C2H5 CHF2 R-43.6 800 C2H5 CHF2 R-44.1
762 C2H5 CHF2 R-43.7 801 C2H5 CHF2 R-44.2
763 C2H5 CHF2 R-43.8 802 C2H5 CHF2 R-44.3
764 C2H5 CHF2 R-43.9 803 C2H5 CHF2 R-44.4
765 C2H5 CHF2 R-43.10 804 C2H5 CHF2 R-44.5
766 C2H5 CHF2 R-43.1 1 805 C2H5 CHF2 R-44.6
767 C2H5 CHF2 R-43.12 806 C2H5 CHF2 R-44.7
768 C2H5 CHF2 R-43.13 807 C2H5 CHF2 R-44.8
769 C2H5 CHF2 R-43.14 808 C2H5 CHF2 R-44.9
770 C2H5 CHF2 R-43.15 809 C2H5 CHF2 R-44.10
771 C2H5 CHF2 R-43.16 810 C2H5 CHF2 R-45.6
772 C2H5 CHF2 R-43.17 81 1 CH2CHF2 CHF2 R-4.1
773 C2H5 CHF2 R-43.18 812 CH2CHF2 CHF2 R-4.2
774 C2H5 CHF2 R-43.19 813 CH2CHF2 CHF2 R-4.3
775 C2H5 CHF2 R-43.20 814 CH2CHF2 CHF2 R-4.4
776 C2H5 CHF2 R-43.21 815 CH2CHF2 CHF2 R-4.5
777 C2H5 CHF2 R-43.22 816 CH2CHF2 CHF2 R-4.6
778 C2H5 CHF2 R-43.23 817 CH2CHF2 CHF2 R-4.7
779 C2H5 CHF2 R-43.24 818 CH2CHF2 CHF2 R-4.8
780 C2H5 CHF2 R-43.25 819 CH2CHF2 CHF2 R-4.9
781 C2H5 CHF2 R-43.26 820 CH2CHF2 CHF2 R-4.10
782 C2H5 CHF2 R-43.27 821 CH2CHF2 CHF2 R-4.1 1
783 C2H5 CHF2 R-43.28 822 CH2CHF2 CHF2 R-4.12
784 C2H5 CHF2 R-43.29 823 CH2CHF2 CHF2 R-4.13
785 C2H5 CHF2 R-43.30 824 CH2CHF2 CHF2 R-4.14
786 C2H5 CHF2 R-43.31 825 CH2CHF2 CHF2 R-4.15
787 C2H5 CHF2 R-43.32 826 CH2CHF2 CHF2 R-4.16
788 C2H5 CHF2 R-43.33 827 CH2CHF2 CHF2 R-4.17
789 C2H5 CHF2 R-43.34 828 CH2CHF2 CHF2 R-4.18
790 C2H5 CHF2 R-43.35 829 CH2CHF2 CHF2 R-41 .1
791 C2H5 CHF2 R-43.36 830 CH2CHF2 CHF2 R-41 .2
792 C2H5 CHF2 R-43.37 831 CH2CHF2 CHF2 R-41 .3 R3a R3b R4 R3a R3b R4
832 CH2CHF2 CHF2 R-41 .4 871 CH2CHF2 CHF2 R-43.35
833 CH2CHF2 CHF2 R-41 .5 872 CH2CHF2 CHF2 R-43.36
834 CH2CHF2 CHF2 R-41 .6 873 CH2CHF2 CHF2 R-43.37
835 CH2CHF2 CHF2 R-41 .7 874 CH2CHF2 CHF2 R-43.38
836 CH2CHF2 CHF2 R-41 .8 875 CH2CHF2 CHF2 R-43.39
837 CH2CHF2 CHF2 R-43.1 876 CH2CHF2 CHF2 R-43.40
838 CH2CHF2 CHF2 R-43.2 877 CH2CHF2 CHF2 R-43.41
839 CH2CHF2 CHF2 R-43.3 878 CH2CHF2 CHF2 R-43.42
840 CH2CHF2 CHF2 R-43.4 879 CH2CHF2 CHF2 R-43.43
841 CH2CHF2 CHF2 R-43.5 880 CH2CHF2 CHF2 R-43.44
842 CH2CHF2 CHF2 R-43.6 881 CH2CHF2 CHF2 R-44.1
843 CH2CHF2 CHF2 R-43.7 882 CH2CHF2 CHF2 R-44.2
844 CH2CHF2 CHF2 R-43.8 883 CH2CHF2 CHF2 R-44.3
845 CH2CHF2 CHF2 R-43.9 884 CH2CHF2 CHF2 R-44.4
846 CH2CHF2 CHF2 R-43.10 885 CH2CHF2 CHF2 R-44.5
847 CH2CHF2 CHF2 R-43.1 1 886 CH2CHF2 CHF2 R-44.6
848 CH2CHF2 CHF2 R-43.12 887 CH2CHF2 CHF2 R-44.7
849 CH2CHF2 CHF2 R-43.13 888 CH2CHF2 CHF2 R-44.8
850 CH2CHF2 CHF2 R-43.14 889 CH2CHF2 CHF2 R-44.9
851 CH2CHF2 CHF2 R-43.15 890 CH2CHF2 CHF2 R-44.10
852 CH2CHF2 CHF2 R-43.16 891 CH2CHF2 CHF2 R-45.6
853 CH2CHF2 CHF2 R-43.17 892 CH2CF3 CHF2 R-4.1
854 CH2CHF2 CHF2 R-43.18 893 CH2CF3 CHF2 R-4.2
855 CH2CHF2 CHF2 R-43.19 894 CH2CF3 CHF2 R-4.3
856 CH2CHF2 CHF2 R-43.20 895 CH2CF3 CHF2 R-4.4
857 CH2CHF2 CHF2 R-43.21 896 CH2CF3 CHF2 R-4.5
858 CH2CHF2 CHF2 R-43.22 897 CH2CF3 CHF2 R-4.6
859 CH2CHF2 CHF2 R-43.23 898 CH2CF3 CHF2 R-4.7
860 CH2CHF2 CHF2 R-43.24 899 CH2CF3 CHF2 R-4.8
861 CH2CHF2 CHF2 R-43.25 900 CH2CF3 CHF2 R-4.9
862 CH2CHF2 CHF2 R-43.26 901 CH2CF3 CHF2 R-4.10
863 CH2CHF2 CHF2 R-43.27 902 CH2CF3 CHF2 R-4.1 1
864 CH2CHF2 CHF2 R-43.28 903 CH2CF3 CHF2 R-4.12
865 CH2CHF2 CHF2 R-43.29 904 CH2CF3 CHF2 R-4.13
866 CH2CHF2 CHF2 R-43.30 905 CH2CF3 CHF2 R-4.14
867 CH2CHF2 CHF2 R-43.31 906 CH2CF3 CHF2 R-4.15
868 CH2CHF2 CHF2 R-43.32 907 CH2CF3 CHF2 R-4.16
869 CH2CHF2 CHF2 R-43.33 908 CH2CF3 CHF2 R-4.17
870 CH2CHF2 CHF2 R-43.34 909 CH2CF3 CHF2 R-4.18 R3a R3b R4
943 CH2CF3 CHF2 R-43.26
944 CH2CF3 CHF2 R-43.27
945 CH2CF3 CHF2 R-43.28
946 CH2CF3 CHF2 R-43.29
947 CH2CF3 CHF2 R-43.30
948 CH2CF3 CHF2 R-43.31
949 CH2CF3 CHF2 R-43.32
950 CH2CF3 CHF2 R-43.33
951 CH2CF3 CHF2 R-43.34
952 CH2CF3 CHF2 R-43.35
953 CH2CF3 CHF2 R-43.36
954 CH2CF3 CHF2 R-43.37
955 CH2CF3 CHF2 R-43.38
956 CH2CF3 CHF2 R-43.39
957 CH2CF3 CHF2 R-43.40
958 CH2CF3 CHF2 R-43.41
959 CH2CF3 CHF2 R-43.42
960 CH2CF3 CHF2 R-43.43
961 CH2CF3 CHF2 R-43.44
962 CH2CF3 CHF2 R-44.1
963 CH2CF3 CHF2 R-44.2
964 CH2CF3 CHF2 R-44.3
965 CH2CF3 CHF2 R-44.4
966 CH2CF3 CHF2 R-44.5
967 CH2CF3 CHF2 R-44.6
968 CH2CF3 CHF2 R-44.7
969 CH2CF3 CHF2 R-44.8
970 CH2CF3 CHF2 R-44.9
971 CH2CF3 CHF2 R-44.10
972 CH2CF3 CHF2 R-45.6
Figure imgf000093_0001
The compounds of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below. Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below. The definitions of Het, X, R1, R2, R3a, R3b and R4 of the molecular structures given in the following schemes are as defined above. Room temperature means a temperature range between about 20 and 25 °C.
Compounds of formula I can be prepared as outlined in scheme 1 by reaction of a ketone of formula (II) with a compound (III), in the presence of a halogenating agent such as phosphoryl chloride by the method described in scheme I .The reaction depicted in scheme 1 can be performend by analogy to the method described by Rapoport et al., Journal of the American Chemical Society, 72, 2783-4; 1950 or in EP 643040.
Schemel :
Figure imgf000094_0001
(II) (I)
Compounds of general formula (II) can be synthesized from the reaction of a primary or secondary amine of formula (IV) with an acid derivative of formula (V) as depicted in scheme 2. In formula (V), the radical L is a suitable leaving group such as halogen or 0-CO)-R3b. The reaction of compound is preferably carried out in aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, Ν,Ν-dimethylacetamide, DMSO, N-metylpyrrolidine, or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane, in particular at temperatures ranging between room temperature and the reflux temperature of the solvent. An amine or inorganic base can be used to facilitate the reaction. Conditions for such a reaction can be found in WO 2004035549. Compounds of formula (IV) are commercially available or can be easily synthesized, e.g. by reduction of the corresponding nitriles or carboxamides.
Compounds of the formula (V) are commercially available or can be synthesized from the corresponding carboxylic acid R3b-C(0)OH using standard procedures of organic chemistry.
Scheme 2:
Figure imgf000094_0002
(IV) (V) (II)
In cases where R4 is a radical NHR5d, the compound of formula (I) can be prepared by reaction of a compound of formula (II) with an isocyanate of the formula R5d-N=C=0 by analogy to the method described in US3998958.
Compounds of formula (III), in which Y is an oxygen bound radical 0-C(=X)-R4, can be obtained as shown in Scheme 3 below:
Scheme 3:
Figure imgf000095_0001
(VI) (VII) (VIII)
Reaction of N-hydroxyphthalimide (VI) with compounds of formula (VII), in which J1 is a chloro, bromo, iodo radical or another suitable leaving group such as OH, yields phthalimide compounds of formula (VIII). If J1 is hydroxyl, the reaction may be performed by analogy to Mitsonobu's reaction in the presence of a suitable trialkyl or triaryl phosphine reagent and a Ν,Ν'-dialkylazodicarboxylate reagent, e.g. by analogy to conditions described in Organic Letters, 2009, 1 1 (9), 2019-2022 or Synthesis, (4), 655-659, and references therein. Cleavage of the phthalimide protecting group in the compound of formula (Villi) to give the compound of formula (lll-A), which is a special case of compound of formula (III) where Y is 0-C(=X)-R4, may be carried out in the presence of hydrazine or methylhydrazine in a polar protic solvent such as methanol or in ethanol. Temperatures may range from 0 °C and 80 °C.
Compounds of formula (III), in which Y is an N bound radical NH-C(=X)-R4, can be obtained as shown in Scheme 4 below:
Scheme 4:
Figure imgf000095_0002
(IX) (X) (XI) (Ni-B)
Reaction of a compound (IX) with compound (X) can be effected by analogy to the procedure described in J. Medicinal Chemistry, 2008, 41 (15), 4601 - 4608. Thus obtained compound XI is subjected to acid conditions, where the tert-butyl carbamate compound (XI) decomposes to the free hydrazide of formula (lll-B). The reaction can be performed as described in Greene, T. W.; Wutz, P. G. M., Protective Groups in Organic Synthesis, Wiley,
Fourth Ed., e.g. by treating compounds of formula (XI) with concentrated mineral acid or trifluoroacetic acid in an aprotic organic solvent at temperatures between 0 °C and 50 °C.
By analogy to the methods described in scheme 4, compounds of formula (III) can be prepared were Y is NH-S(=0)R5b or NH-S(=0)2R5b, respectively.
An alternative method to synthesize compound of formula (I), where R3a is different from
H, is described in scheme 5. In a first step, the compound of formula (I) with R3a = H is prepared as described in Scheme 1 , and then reacted with compound of formula (XI), to afford
compounds of formula (I), where R3a is different from H. In scheme 5, R3aa in the compound of formula (VI) has one of the meanings of R3a which is different from hydrogen. In particular, R3aa represents a C-bound radical R3a. LG in compound of formula (XI) is suitable leaving group.
Examples of suitable leaving groups LG include, but are not limited to halogen, such as fluorine, chlorine or bromine, alkyl sulfonate such as mesylate, haloalkyl sulfonate, such as trifluoromethansulfonate and alkyl phosphonate The reaction is preferably carried out in polar solvents such as acetonitrile, acetone, fe/7-butyl alcohol, tetrahydrofuran, N,N- dimethylformamide, Ν,Ν-dimethylacetamide, DMSO, N-methylpyrrolidine, dichloromethane, 1 ,2- dichloroethane, or 1 ,2-dimethoxyethane, in particular at temperatures ranging between room temperature and the reflux temperature of the solvent in the presence of a organic or inorganic base. Suitable reaction conditions can be found in: WO2008/009360.
Scheme 5:
Figure imgf000096_0001
In cases where X in radicals Y1, Y2 or Y3 of formula (I) is a sulfur atom, the sulfur atom may be introduced in a subsequent step by reacting a compound of formula (I), where X is an oxygen atom, with a thio phosphorous reagent, e.g. P4-Sio-pyridine complex or Lawesson's reagent (2,4-Bis-(4-methoxyphenyl)-1 ,3,2,4-dithiadiphosphetan-2,4-disulfide) or a similar 2,4- Bis-(aryl)- or 2,4-'Bis(alkyl)-1 ,3,2,4-dithiadiphosphetan-2,4-disulfide, preferably in polar aprotic solvents such as acetonitrile, acetone, tetrahydrofuran, Ν,Ν-dimethylformamide, or in an inert solvent such as toluene, xylene, dichloromethane, chlorobenzene, 1 ,2-dichloroethane, or 1 ,2- dimethoxyethane. The reaction temperature may range from room temperature to the reflux temperature of the solvent. Representative reaction conditions for thionation analogous substrates are given in US 2013/102568.
The compounds of the formula (I), and their salts are in particular suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.
The compounds of the formula (I) are especially suitable for efficiently combating insects, in particular the following pests:
Insects from the order of the lepidopterans {Lepidoptera), for example Acronicta major,
Adoxophyes orana, Aedia leucomelas, Agrotis spp. such as Agrotis fucosa, Agrotis segetum, Agrotis ypsilon; Alabama argillacea, Ant/cars/a gemmatalis, Ant/cars/a spp., Argyresthia conjugella, Autographa gamma, Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia murinana, Cacoecia podana, Capua reticuiana, Carpocapsa pomoneiia, Cheimatobia brumata, Chilo spp. such as Chilo suppressalis; Choristoneura fumiferana, Choristoneura occiden talis, Cirphis unipuncta, Clysia ambiguella, Cnaphalocerus spp., Cydia pomoneiia, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiose/la, Ear/as insu/ana, Elasmopalpus lignosellus, Ephestia cautella, Ephestia kuehniella, Eupoecilia ambiguella, Euproctis
chrysorrhoea, Euxoa spp., Evetria bouliana, Feltia spp. such as Feltia subterranean; Galleria meiioneiia, Graphoiitha funebrana, Graphoiitha moiesta, Helicoverpa spp. such as Helicoverpa armigera, Helicoverpa zea; Heliothis spp. such as Heliothis armigera, Heliothis virescens, Heliothis zea; Hellula undalis, Hibernia defoliaria, Hofmannophila pseudospretella, Homona magnanima, Hyphantria cunea, Hyponomeuta padella, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma spp. such as Laphygma exigua; Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lithophane antennata, Lobes/a botrana, Loxagrotis albicosta, Loxostege sticticalis, Lymantria spp. such as Lymantria dispar, Lymantria monacha; Lyonetia clerkella, Malacosoma neustria, Mamestra spp. such as Mamestra brassicae; Mocis repanda, Mythimna separata, Orgyia pseudotsugata, Oria spp., Ostrinia spp. such as Ostrinia nubilalis; Oulema oryzae, Panolis flammea, Pectinophora spp. such as
Pectinophora gossypiella; Peridroma saucia, Phalera bucephala, Phthorimaea spp. such as Phthorimaea opercuieiia; Phyiiocnistis citreiia, Pieris spp. such as Pieris brassicae, Pieris rapae; P lathy pen a sea bra, Plutella maculipennis, Plutella xylostella, Prod en ia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera spp. such as Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; Thaumatopoea pityocampa, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp. such as Trichoplusia ni; Tuta absoluta, and Zeiraphera canadensis;
Beetles {Coleoptera), for example Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus sinuatus, Agriotes spp. such as Agriotes fuscicollis, Agriotes lineatus, Agriotes obscurus; Amphimallus solstitialis, Anisandrus dispar, Anobium punctatum, Anomala
rufocuprea, Anoplophora spp. such as Anoplophora g/abr/penn/s; Anthonomus spp. such as
Anthonomus grandis, Anthonomus pomorum; Anthrenus spp., Aphthona euphoridae, Apogonia spp., Athous haemorrhoida/is, Atomaria spp. such as Atomaria linearis; Attagenus spp., Aulacophora fern oral is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as Bruchus lentis, Bruchus pisorum, Bruchus rufimanus; Byctiscus betulae, Callosobruchus chine nsis, Cassida nebulosa, Cerotoma trifurcata, Ce ton/a a u rata,
Ceuthorhynchus spp. such as Ceuthorrhynchus assimiiis, Ceuthorrhynchus napi; Chaetocnema tibialis, Cleonus mendicus, Conoderus spp. such as Conoderus vespertinus; Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptorhynchus lapathi, Ctenicera ssp. such as Ctenicera destructor; Curculio spp., Dectes texanus, Dermestes spp., Diabrotica spp. such as Diabrotica 12-punctata Diabrotica speciosa, Diabrotica longicornis, Diabrotica semipunctata,
Diabrotica virgifera; Epilachna spp. such as Epilachna varivestis, Epilachna vigintioctomaculata; Epitrix spp. such as Epitrix hirtipennis; Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera brunneipennis, Hypera postica, Hypothenemus spp., Ips typographus, Lachnosterna consanguinea, Lema bilineata, Lema melanopus, Leptinotarsa spp. such as Leptinotarsa decemlineata; Limonius caiifornicus, Lissorhoptrus oryzophiius, Lissorhoptrus oryzophiius, Lixus spp., Lyctus spp. such as Lyctus bruneus; Melanotus communis, Meligethes spp. such as Meligethes aeneus; Melolontha hippocastani, Melolontha melolontha, Migdolus spp.,
Monochamus spp. such as Monochamus alternatus; Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus,
Otiorrhynchus ovatus, Otiorrhynchus sulcatus, Oulema oryzae, Oxyce ton/a jucunda, Phaedon cochleariae, Phyllobius pyri, Phyllopertha horticola, Phyllophaga spp., Phyllotreta spp. such as Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata; Phyllophaga spp., Phyllopertha horticola, Pop/Ilia japonica, Premnotrypes spp., Psylliodes chrysocephala, P tin us spp., Rhizobius ventralis , Rhizopertha dominica, Sitona lineatus, Sitophilus spp. such as Sitophilus granaria, Sitophilus zeamais; Sphenophorus spp. such as Sphenophorus levis;
Sternechus spp. such as Sternechus subsignatus; Symphyletes spp., Tenebrio molitor, Tribolium spp. such as Tribolium castaneum; Trogoderma spp., Tychius spp., Xylotrechus spp., and Zabrus spp. such asZabrus tenebrioides;
Flies, mosquitoes {Diptera), e.g. Aedes spp. such as Aedes aegypti, Aedes albopictus, Aedes vexans; Anastrepha ludens, Anopheles spp. such as Anopheles albimanus, Anopheles crucians, Anopheles freeborni, Anopheles gambiae, Anopheles leucosphyrus, Anopheles maculipennis, Anopheles minimus, Anopheles quadrimaculatus, Anopheles sinensis; Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Cerafitis capitata, Ceratitis capitata, Chrysomyia spp. such as Chrysomya bezziana, Chrysomya hominivorax, Chrysomya maceiiaria; Chrysops atianticus, Chrysops discalis, Chrysops siiacea, Cochliomyia spp. such as Cochliomyia hominivorax; Contarinia spp. such as Contarinia sorghicola; Cordylobia
anthropophaga, Culex spp. such as Culex nigripalpus, Culex pip/ens, Cu/ex quinquefasciatus, Culex tarsalis, Culex tritaeniorhynchus; Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp., Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia spp. such as Delia antique, Delia coarctata, Delia platura, Delia radicum; Derma tobia hominis, Drosophila spp., Fannia spp. such as Fannia canicularis; Q>a \xa^ \\\ spp. such as Gasterophilus intestinalis; Geomyza Tripunctata, Glossina fuscipes, Glossina morsitans, Glossina pa/pa/is, G/ossina tach/noides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia spp. such as Hylemyia platura; Hypoderma spp. such as Hypoderma lineata; Hyppobosca spp.,
Leptoconops torrens, Liriomyza spp. such as Liriomyza sativae, Liriomyza trifolii; Lucilia spp. such as Lucilia caprina, Lucilia cuprina, Lucilia sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as Mayetiola destructor; Musca spp. such as Musca autumnalis, Musca domestica; Muscina stabulans, Oestrus spp. such as Oestrus ovis; Opomyza florum, Oscineiia spp. such as Oscineiia frit; Pegomya hysocyami, Phiebotomus argentipes, Phorbia spp. such as Phorbia antiqua, Phorbia brassicae, Phorbia coarctata; Prosimulium mixtum, Psila rosae, Psorophora columbiae, Psorophora discolor, Rhagoletis cerasi, Rhagoletis pomonella,
Sarcophaga spp. such as Sarcophaga haemorrhoidalis; Simuiium vittatum, Stomoxys spp. such as Stomoxys ca/citrans; Tabanus spp. such as Tabanus atratus, Tabanus bov/nus, Tabanus lineola, Tabanus similis; Tannia spp., Tipula oleracea, Tipula paludosa, and Wohlfahrtia spp.;
Thrips { Thysanoptera), e.g. Baliothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Enneothrips flavens, Frankliniella spp. such as Frankliniella fusca, Frankliniella
occidentalis, Frankliniella tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp. such as Scirtothrips citri; Taeniothrips cardamoni, Thrips spp. such as Thrips oryzae, Thrips palmi, Thrips tabaci;
Termites (Isoptera), e.g. Calotermes flavicollis, Coptotermes formosanus, Heterotermes aureus, Heterotermes longiceps, Heterotermes tenuis, Leucotermes flavipes, Odontotermes spp., Reticulitermes spp. such as Reticulitermes speratus, Reticulitermes flavipes, Reticulitermes grassei, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes virginicus; Termes natalensis;
Cockroaches (Blattaria - Blattodea), e.g. Acheta domesticus, Blatta orientalis, Blattella asahinae, Blattella germanica, Gryllotalpa spp., Leu cop ha ea maderae, Locus ta spp.,
Me Ian op/us spp., Peri plane ta americana, Peri pi an eta australasiae, Peri pi an eta brunnea, Periplaneta fuligginosa, Periplaneta japonica;
Bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g.
Acrosternum spp. such as Acrosternum hi/are; Acyrt oslpon spp. such as Acyrthosiphon onobrychis, Acyrthosiphon pisum; Adelges laricis, Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphidula nasturtii, Aphis spp. such as Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis grossuiariae, Aphis pomi, Aphis sambuci, Aphis schneideri, Aphis spiraecoia; Arboridia apicaiis, Ariius critatus, Aspidielia spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp. such as Bemisia argentifolii, Bemisia tabaci; Blissus spp. such as Blissus leucopterus; Brachycaudus cardui, Brachycaudus helichrysi, Brachycaudus persicae, Brachycaudus prunicola, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Calocoris spp., Campylomma livid a,
Capitophorus horn/, Carneocephala fulgida, Cavelerius spp., Ceraplastes spp., Ceratovacuna la nig era, Cercopidae, Cerosipha gossypii, Chaetosiphon fragaefolii, Ch ion asp is tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Cimex spp. such as Cimex hemipterus, Cimex lectularius; Coccomytilus halli, Coccus spp., Creontiades dilutus, Cryptomyzus ribis, Cryptomyzus rib is, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurades spp., Diaphorina spp., Diaspis spp., Dichelops furcatus, Diconocoris hewetti, Dora/is spp., Dreyfus/a nordmann/anae, Dreyfus/a piceae, Drosicha spp., Dysaphis spp. such as Dysaphis plantaginea, Dysaphis pyri, Dysaphis radicola; Dysaulacorthum pseudoso/ani, Dysdercus spp. such as Dysdercus cingu/atus, Dysdercus intermedius;
Dysm/coccus spp., Empoasca spp. such as Empoasca fabae, Empoasca so/ana; Er/osoma spp., Erythroneura spp., Eurygaster spp. such as Eurygaster integriceps; Eusce/is bi/obatus, Euschistus spp. such as Euschistuos heros, Euschistus impictiventris, Euschistus servus; Geococcus coffeae, Halyomorpha spp. such as Halyomorpha halys; Heliopeltis spp.,
Homalodisca coagulata, Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as Lygus hesperus, Lygus lineolaris, Lygus pratensis; Macropes excavatus, Macrosiphum spp. such as Macrosiphum rosae, Macrosiphum a venae, Macrosiphum euphorbiae; Mahanarva fimbriolata, Megacopta cribraria, Megoura viciae, Melanaphis pyrarius, Melanaphis sacchari, Metcafiella spp., Metopolophium dirhodum, Miridae spp., Monellia costalis, Monelliopsis pecanis, Myzus spp. such as Myzus ascalonicus, Myzus cerasi, Myzus persicae, Myzus varians; Nasonovia ribis-nigri, Nephotettix spp. such as Nephotettix maiayanus, Nephotettix nigropictus, Nephotettix parvus, Nephotettix virescens; Nezara spp. such as Nezara viridula; Nilaparvata lugens, Oebalus spp., Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp. such as Pemphigus bursarius; Pentomidae, Peregrinus maidis, Perkinsiella saccharic/da, Phenacoccus spp., Phloeomyzus passe rinii, Phorodon humuli, Phylloxera spp., Piesma quadrata, Piezodorus spp. such as Piezodorus guildinii, Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, P sail us seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudococcus spp. such as Pseudococcus comstocki; Psylla spp. such as Psylla mali, Psylla piri; Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as Rhopalosiphum pseudobrassicas, Rhopalosiphum insertum, Rhopalosiphum maidis, Rhopalosiphum pad/; Sagatodes spp., Sahlbergella singularis, Saissetia spp., Sappaphis mala, Sappaphis mali, Scaphoides titanus, Schizaphis gram in um, Schizoneura lanuginosa, Scotinophora spp., Selenaspidus articulatus, Sitobion a venae, Sogata spp., Sogatella furcifera, Solubea insularis , Stephanitis nashi, Stictocephala festina, Tenalaphara malayensis, Thyanta spp. such as Thyanta perditor; Tibraca spp.,
Tinocaiiis caryaefoiiae, Tomaspis spp., Toxoptera spp. such as Toxoptera aurant/i; ! rialeurodes spp. such as Tr/a/eurodes vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as Unaspis yanonensis; and Viteus vitifolii;
Ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta capiguara, Atta cephalotes, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Bombus spp., Camponotus floridanus, Crematogaster spp., Dasymutilla occidental is, Di prion spp., Dolichovespula maculata, Hoplocampa spp. such as Hoplocampa minuta, Hoplocampa testudinea; Lasius spp. such as Las/us niger, Linepithema humi/e, Monomorium pharaonis, Paravespula germanica, Paravespula pennsylvanica, Paravespula vulgaris, Pheidole megacephala, Pogonomyrmex barbatus, Pogonomyrmex californicus, Polistes rubiginosa, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Vespa spp. such as Vespa crabro, and Vespula squamosal;
Crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Calliptamus italicus, Chortoicetes terminifera, Dociostaurus maroccanus, Gryllotalpa africana, Gryllotalpa gryllotalpa, Hieroglyphus daganensis, Kraussaria angulifera, Locus ta migratoria, Locus tana pardalina, Me Ian op/us bivittatus, Mela no pi us femurrubrum, Mela no pi us mexicanus, Mela no pi us sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Oedaleus senegalensis, Schistocerca americana, Schistocerca gregaria, Tachycines asynamorus, and Zonozerus variegatus;
Earwigs {Dermaptera), e.g. forficula auricularia,
Lice {Phthiraptera), e.g. Damalinia spp., Pediculus spp. such as Pediculus humanus capitis, Pediculus humanus corporis; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.;
Fleas {Siphonaptera), e.g. Ceratophyllus spp., Ctenocephalides felis, Ctenocephalides can is, Xe no psylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus. The compounds of the formula (I) are also suitable for efficiently combating arthropd pests different from insects such as, in particular the following pests:
arachnids {Arachnids), such as acari,e.g. of the families Argasidae, Ixodidae and
Sarcoptidae, such as Amblyomma spp. (e.g. Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum), Argas spp. (e.g. Argas persicus), Boophilus spp. (e.g. Boophilus annulatus, Boophilus decoloratus, Boophilus micro pi us), Dermacentor sil varum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma spp. (e.g. Hyalomma truncatum), Ixodes spp. (e.g. Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus), Ornithodorus spp. (e.g. Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata), Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae,
Psoroptes spp. (e.g. Psoroptes ovis), Rhipicephalus spp. (e.g. Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi), Rhizoglyphus spp., Sarcoptes spp. (e.g. Sarcoptes scabiei), and Eriophyidae spp. such as Acaria sheldoni, Aculops spp. (e.g. Aculops pelekassi) Aculus spp. (e.g. Aculus schlechtendall), Epitrimerus pyri, Phyllocoptruta oleivora and Eriophyes spp. (e.g. Eriophyes sheldoni); Tarsonemidae spp. such as Hemitarsonemus spp., Phytonemus pallidus and Polyphagotarsonemus latus, Stenotarsonemus spp:,
Tenuipalpidae spp. such as Brevipalpus spp. (e.g. Brevipalpus phoenicis); Tetranychidae spp. such as Eotetranychus spp., Eutetranychus spp., Oiigonychus spp., Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae; Bryobia praetiosa, Panonychus spp. (e.g. Panonychus ulmi, Panonychus citri), Metatetranychus spp. and Oiigonychus spp. (e.g. Oiigonychus pratensis), Vasates lycopersici, Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa. And Acarus siro, Chorioptes spp., Scorpio maurus,
Silverfish, firebrat { Thysanura), e.g. Lepisma saccharina and Thermobia domestica;
Centipedes {Chilopoda), e.g. Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,
Millipedes {Diplopoda), e.g. Blaniulus guttulatus, Narceus spp.,
Springtails (Collembola ), e.g. Onychiurus ssp. such as Onychiurus armatus,
They are also suitable for controlling nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifoiii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species such as Aphelenchoides besseyi '; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus lignicolus Mamiya et Kiyohara, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species,
Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaciand other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, He/iocoty/enchus mu/ticinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus brachyurus, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi 'and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes,
Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species such as T ylenchulus semipenetrans, Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.
Examples of further pest species which may be controlled by compounds of fomula (I) include: from the class of the Bivalva, for example, Dreissena spp:, from the class of the Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis,
Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooper/a spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp.,
Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercora lis, Stronyloides spp., Taenia saginata, Taenia solium, Trichineiia spiralis, Trichineiia nativa, Trichineiia britovi, Trichineiia ne/soni, Trichineiia pseudopsiralis, Trichostrongu/us spp., Trichuris trichuria, Wuchereria bancrofti; from the order of the Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order of the Symphyla, for example, Scutigerella immaculata.
Further examples of pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis,
Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema a rid u la, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminifera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus ma id is, Deraceras reticu latum , Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera , Diloboderus spp. such as Diloboderus abderus; Edessa spp., Epinotia spp., Formicidae, Geocoris spp., Glob iter mes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia oratorius , Liogenys fuscus, Luciiiia spp., Lyogenys fuscus, Mahanarva spp., Ma lad era math da, Marasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Micro theca spp., Mods latipes, Murgantia spp., Mythemina separata ,
Neocapritermes opacus, Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphula depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triad fer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris casta nea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp. such as Sesamia inferens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips bi for mis,
Steneotarsonemus spinki, Sylepta derogata, Telehin licus, Trichostrongylus spp..
Compounds of the formula (I) are particularly useful for controlling insects of the orders Hemiptera and Thysanoptera.
For use in a method according to the present invention, the compounds of the formula (I) can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules and directly sprayable solutions. The use form depends on the particular purpose and application method. Formulations and application methods are chosen to ensure in each case a fine and uniform distribution of the compound of the formula (I) according to the present invention.
The formulations are prepared in a known manner (see e.g. for review US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, US 4,172,714, US 4,144,050, US 3,920,442, US 5,180,587, US 5,232,701 , US 5,208,030, GB 2,095,558, US 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961 , Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001 , 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic
Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active compound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, antifoaming agents, anti-freezing agents, for seed treatment formulation also optionally colorants and/or binders and/or gelling agents.
Solvents/carriers, which are suitable, are e.g.:
solvents such as water, aromatic solvents (for example Solvesso products, xylene and the like), paraffins (for example mineral fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-metyhl-pyrrolidone (NMP),N-octylpyrrolidone NOP), acetates (glycol diacetate), alkyl lactates, lactones such as g-butyrolactone, glycols, fatty acid
dimethylamides, fatty acids and fatty acid esters, triglycerides, oils of vegetable or animal origin and modified oils such as alkylated plant oils. In principle, solvent mixtures may also be used.
carriers such as ground natural minerals and ground synthetic minerals, such as silica gels, finely divided silicic acid, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
Suitable emulsifiers are nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates.
Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of
naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers,
tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters,
Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.
Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.
Suitable preservatives are for example dichlorophen und benzyl alcohol hemiformal Suitable thickeners are compounds which confer a pseudoplastic flow behavior to the formulation, i.e. high viscosity at rest and low viscosity in the agitated stage. Mention may be made, in this context, for example, of commercial thickeners based on polysaccharides, such as Xanthan Gum® (Kelzan® from Kelco), Rhodopol®23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), or organic phyllosilicates, such as Attaclay® (from Engelhardt). Antifoam agents suitable for the dispersions according to the invention are, for example, silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, organofluorine compounds and mixtures thereof. Biocides can be added to stabilize the compositions according to the invention against attack by microorganisms. Suitable biocides are, for example, based on isothiazolones such as the compounds marketed under the trademarks Proxel® from Avecia (or Arch) or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas. Suitable antifreeze agents are organic polyols, for example ethylene glycol, propylene glycol or glycerol. These are usually employed in amounts of not more than 10% by weight, based on the total weight of the active compound composition. If appropriate, the active compound compositions according to the invention may comprise 1 to 5% by weight of buffer, based on the total amount of the formulation prepared, to regulate the pH, the amount and type of the buffer used depending on the chemical properties of the active compound or the active compounds. Examples of buffers are alkali metal salts of weak inorganic or organic acids, such as, for example, phosphoric acid, boronic acid, acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid and succinic acid.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0,01 to 60% by weight active compound by weight, preferably 0,1 to 40% by weight.
The compound of formula (I) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.
The following are examples of formulations:
1 . Products for dilution with water. For seed treatment purposes, such products may be
applied to the seed diluted or undiluted.
A) Water-soluble concentrates (SL, LS)
10 parts by weight of the active compound is dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound dissolves upon dilution with water, whereby a formulation with 10 % (w/w) of active compound is obtained.
B) Dispersible concentrates (DC)
20 parts by weight of the active compound is dissolved in 70 parts by weight of
cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compounds is obtained.
C) Emulsifiable concentrates (EC)
15 parts by weight of the active compounds is dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compounds is obtained.
D) Emulsions (EW, EO, ES)
25 parts by weight of the active compound is dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound is obtained.
E) Suspensions (SC, OD, FS)
In an agitated ball mill, 20 parts by weight of the active compound is comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w/w) of active compound is obtained.
F) Water-dispersible granules and water-soluble granules (WG, SG)
50 parts by weight of the active compound is ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 50% (w/w) of active compound is obtained.
G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)
75 parts by weight of the active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound, whereby a formulation with 75% (w/w) of active compound is obtained.
H) Gel-Formulation (GF)
In an agitated ball mill, 20 parts by weight of the active compound is comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of a gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound, whereby a formulation with 20% (w/w) of active compound is obtained.
2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.
I) Dustable powders (DP, DS) 5 parts by weight of the active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound.
J) Granules (GR, FG, GG, MG)
0.5 part by weight of the active compound is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
K) ULV solutions (UL)
10 parts by weight of the active compound is dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound, which is applied undiluted for foliar use.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 %.
The active ingredients may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.
In the method of this invention compounds of formula (I) may be applied with other active ingredients, for example with other pesticides, insecticides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators, safeners and nematicides. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a
composition of this invention either before or after being treated with other active ingredients.
M.1 Acetylcholine esterase (AChE) inhibitors from the class of
M.1A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb,
butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of
M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;
M.2. GABA-gated chloride channel antagonists such as:
M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
M.3 Sodium channel modulators from the class of
M.3A pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, meperfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and transfluthrin; or
M.3B sodium channel modulators such as DDT or methoxychlor;
M.4 Nicotinic acetylcholine receptor agonists (nAChR) from the class of
M.4A neonicotinoids, for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds
M.4A.1 : 1 -[(6-chloro-3-pyridinyl)methyl]-2,3,5,6,7,8-hexahydro-9-nitro-(5S,8R)-5,8-Epoxy- 1 H-imidazo[1 ,2-a]azepine; or
M.4A.2: 1 -[(6-chloro-3-pyridyl)methyl]-2-nitro-1 -[(E)-pentylideneamino]guanidine; or
M4.A.3: 1 -[(6-chloro-3-pyridyl)methyl]-7-methyl-8-nitro-5-propoxy-3,5,6,7-tetrahydro-2H- imidazo[1 ,2-a]pyridine;
or M.4B nicotine.
M.5 Nicotinic acetylcholine receptor allosteric activators from the class of spinosyns, for example spinosad or spinetoram;
M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
M.7 Juvenile hormone mimics, such as
M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
M.8 miscellaneous non-specific (multi-site) inhibitors, for example
M.8A alkyl halides as methyl bromide and other alkyl halides, or
M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
M.9 Selective homopteran feeding blockers, for example
M.9B pymetrozine, or M.9C flonicamid; M.10 Mite growth inhibitors, for example
M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
M.1 1 Microbial disruptors of insect midgut membranes, for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israe/ensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
M.12 Inhibitors of mitochondrial ATP synthase, for example
M.12A diafenthiuron, or
M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;
M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, for example chlorfenapyr, DNOC or sulfluramid;
M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
M.16 Inhibitors of the chitin biosynthesis type 1 , as for example buprofezin;
M.17 Moulting disruptors, Dipteran, as for example cyromazine;
M.18 Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
M.19 Octopamin receptor agonists, as for example amitraz;
M.20 Mitochondrial complex III electron transport inhibitors, for example
M.20A hydramethylnon, or M.20B acequinocyl, or M.20C fluacrypyrim;
M.21 Mitochondrial complex I electron transport inhibitors, for example
M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone;
M.22 Voltage-dependent sodium channel blockers, for example
M.22A indoxacarb, or M.22B metaflumizone, or M.22C 1 -[(E)-[2-(4-cyanophenyl)-1 -[3-
(trifluoromethyl)phenyl]ethylidene]amino]-3-[4-(difluoromethoxy)phenyl]urea;
M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
M.24 Mitochondrial complex IV electron transport inhibitors, for example
M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide.
M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
M.28 Ryanodine receptor-modulators from the class of diamides, as for example flubendiamide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), or the phthalamide compounds M.28.1 : (R)-3-Chlor-NH2-methyM-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2- (1 -methyl-2-methylsulfonylethyl)phthalamid and
M.28.2: (S)-3-Chlor-N1 -{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2- (1 -methyl-2-methylsulfonylethyl)phthalamid, or the compound
M.28.3: 3-bromo-N-{2-bromo-4-chloro-6-[(1 -cyclopropylethyl)carbamoyl]phenyl}-1 -(3- chlorpyridin-2-yl)-1 H-pyrazole-5-carboxamide (proposed ISO name: cyclaniliprole), or the compound
M.28.4: methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5- yl]carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; or a compound selected from M.28.5a) to M.28.5I):
M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2- (3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5c) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-
2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5e) N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide;
M.28.5f) N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5g) N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3- chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;
Μ.28.5Ϊ) N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-5-bromo-2-(3- chloro-2-pyridyl)pyrazole-3-carboxamide;
M.28.5j) 5-chloro-2-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[(1 -cyano-1 -methyl- ethyl)carbamoyl]phenyl]pyrazole-3-carboxamide;
M.28.5k) 5-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloro-2- pyridyl)pyrazole-3-carboxamide;
M.28.5I) N-[2-(tert-butylcarbamoyl)-4-chloro-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (fluoromethoxy)pyrazole-3-carboxamide; or a compound selected from
M.28.6 N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)-3-iodo-phthalamide; or
M.28.7 3-chloro-N2-(1 -cyano-1 -methyl-ethyl)-N1 -(2,4-dimethylphenyl)phthalamide;
M.UN.X insecticidal active compounds of unknown or uncertain mode of action, as for example afidopyropen, azadirachtin, amidoflumet, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, flufenerim, flometoquin, fluensulfone, flupyradifurone, piperonyl butoxide, pyridalyl, pyrifluquinazon, sulfoxaflor, pyflubumide or the compounds M.UN.X.1 : 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl- N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide, or the compound
M.UN.X.2: 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N- [2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]naphthalene-1 -carboxamide, or the compound
M.UN.X.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1 -en-10-one, or the compound
M.UN.X.4: 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3- en-2-one, or the compound
M.UN.X.5: 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)- 1 H-1 ,2,4-triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582); or
M.UN.X.6; a compound selected from the group of
M.UN.X.6a) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
M.UN.X.6b) (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
M.UN.X.6c) (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyridylidene]acetamide; M.UN.X.6d) (E/Z)-N-[1 -[(6-bromo-3-pyridyl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
M.UN.X.6e) (E/Z)-N-[1 -[1 -(6-chloro-3-pyridyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide;
M.UN.X.6†) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; M.UN.X.6g) (E/Z)-2-chloro-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2-difluoro- acetamide;
M.UN.X.6h) (E/Z)-N-[1 -[(2-chloropyrimidin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro- acetamide and
M.UN.X.6i) (E/Z)-N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro- propanamide.); or of the compounds
M.UN.X.7: 3-[3-chloro-5-(trifluoromethyl)phenyl]-4-oxo-1 -(pyrimidin-5-ylmethyl)pyrido[1 ,2- a]pyrimidin-1 -ium-2-olate; or
M.UN.X.8: 8-chloro-N-[2-chloro-5-methoxyphenyl)sulfonyl]-6-trifluoromethyl)-imidazo[1 ,2- a]pyridine-2-carboxamide; or
M.UN.X.9: 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 - oxothietan-3-yl)benzamide; or
M.UN.X.10: 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole.
The commercially available compounds of the group M listed above may be found in The Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications.
The quinoline derivative flometoquin is shown in WO 2006/013896. The aminofuranone compounds flupyradifurone is known from WO 2007/1 15644. The sulfoximine compound sulfoxaflor is known from WO 2007/149134. The pyrethroid momfluorothrin is known from US 6908945. The pyrazole acaricide pyflubumide is known from WO 2007/020986. The isoxazoline compounds have been described likewise M.UN.X.1 in WO 2005/085216, M.UN.X2. in WO 2009/002809 and in WO 201 1/149749 and the isoxazoline M.UN.X.9 in WO
2013/050317. The pyripyropene derivative afidopyropen has been described in WO
2006/129714. The spiroketal-substituted cyclic ketoenol derivative M.UN.X.3 is known from WO 2006/089633 and the biphenyl-substituted spirocyclic ketoenol derivative M.UN.X.4 from WO 2008/06791 1 . Finally triazoylphenylsulfide like M.UN.X.5 have been described in WO
2006/043635 and biological control agents on basis of bacillus firmus in WO 2009/124707. The neonicotionids 4A.1 is known from WO 20120/069266 and WO 201 1/06946, the M.4.A.2 from WO 2013/003977, the M4.A.3.from WO 2010/069266.
The Metaflumizone analogue M.22C is described in CN 10171577. The phthalamides
M.28.1 and M.28.2 are both known from WO 2007/101540. The anthranilamide M.28.3 has been described in WO 2005/077934. The hydrazide compound M.28.4 has been described in WO 2007/043677. The anthranilamides M.28.5a) to M.28.5h) can be prepared as described in WO 2007/006670, WO 2013/024009 and WO 2013/024010, the anthranilamide Μ.28.5Ϊ) is described in WO 201 1/085575, the M.28.5j) in WO 2008/134969, the M.28.5k) in US
201 1/046186 and the M.28.5I) in WO 2012/034403. The diamide compounds M.28.6 and M.28.7 can be found in CN 102613183.
The compounds M.UN.X.6a) to M.UN.X.6i) listed in M.UN.X.6 have been described in WO 2012/029672. The mesoionic antagonist compound M.UN.X.7 was described in
WO 2012/0921 15, the nematicide M.UN.X.8 in WO 2013/055584 and the Pyridalyl-type analogue M.UN.X.10 in WO 2010/060379.
In another embodiment of the invention, the compounds of formula (I), or their
stereoisomers, salts, tautomers and N-oxides, may also be applied with fungicides as compound II.
The following list F of active substances, in conjunction with which the compounds according to the invention can be used, is intended to illustrate the possible combinations but does not limit them:
F.I) Respiration Inhibitors
F.1-1 ) Inhibitors of complex III at Qo site:
strobilurins: azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin,
enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb/chlorodincarb, trifloxystrobin, 2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2 (2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N methyl-acetamide;
oxazolidinediones and imidazolinones: famoxadone, fenamidone;
F.I-2) Inhibitors of complex II (e.g. carboxamides):
carboxanilides: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fenhexamid, fluopyram, flutolanil, furametpyr, isopyrazam, isotianil, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, tiadinil, 2-amino-4 methyl-thiazole- 5-carboxanilide, N-(3',4',5' trifluorobiphenyl-2 yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4 carboxamide (fluxapyroxad), N-(4'-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1 -methyl-1 H pyrazole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5 fluoro-1 H-pyrazole- 4 carboxamide, 3-(difluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 3-(trifluoromethyl)-1 -methyl-N-(1 , 1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5- dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide, 3-(trifluoromethyl)-1 -methyl-N-(1 , 1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3-dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5- dimethyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1 ,3,5-trimethyl-N-(1 ,1 ,3-trimethylindan-4- yl)pyrazole-4-carboxamide;
F.I-3) Inhibitors of complex III at Qi site: cyazofamid, amisulbrom, [(3S,6S,7R,8R)-8-benz- yl-3-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(acetoxymethoxy)-4-methoxy-pyridine- 2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)- 8-benzyl-3-[(3-isobutoxycarbonyloxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yl] 2-methylpropanoate, [(3S,6S,7R,8R)-8-benzyl-3-[[3-(1 ,3-benzodioxol-5- ylmethoxy)-4-methoxy-pyridine-2-carbonyl]amino]-6-methyl-4,9-dioxo-1 ,5-dioxonan-7-yl] 2- methylpropanoate, 35,65,7 ?,8 )-3-[[(3-hydroxy-4-methoxy-2-pyridinyl)carbonyl]amino]- 6-methyl-4,9-dioxo-8-(phenylmethyl)-1 ,5-dioxonan-7-yl 2-methylpropanoate;
F.I-4) Other respiration inhibitors (complex I, uncouplers) diflumetorim; (5,8-difluoro- quinazolin-4-yl)-{2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl}-amine;
tecnazen;ametoctradin; silthiofam; nitrophenyl derivates: binapacryl, dinobuton, dinocap, fluazinam, ferimzone, nitrthal-isopropyl,
and including organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide;
F.ll) Sterol biosynthesis inhibitors (SBI fungicides)
F.II-1 ) C14 demethylase inhibitors (DMI fungicides, e.g. triazoles, imidazoles)
triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil,
paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, 1 -[reA(2^3 ^-3-(2-chloro- phenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H-[1 ,2,4]triazole, 2-[reA(2^3 )-3- (2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-2H-[1 ,2,4]triazole-3-thiol;
imidazoles: imazalil, pefurazoate, oxpoconazole, prochloraz, triflumizole;
pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine, 1 -[rel- (2^3 )-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]-5-thiocyanato-1 H- [1 ,2,4]triazole, 2-[rel-(2S;3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-oxiranylmethyl]- 2H-[1 ,2,4]triazole-3-thiol;
F.II-2) Delta14-reductase inhitors (Amines, e.g. morpholines, piperidines)
morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; piperidines: fenpropidin, piperalin; spiroketalamines: spiroxamine;
F.II-3) Inhibitors of 3-keto reductase: hydroxyanilides: fenhexamid;
F.lll) Nucleic acid synthesis inhibitors
F.III-1 ) RNA, DNA synthesis
phenylamides or acyl amino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
isoxazoles and iosothiazolones: hymexazole, octhilinone;
F.III-2) DNA topisomerase inhibitors: oxolinic acid;
F.III-3) Nucleotide metabolism (e.g. adenosin-deaminase), hydroxy (2-amino)-pyrimidines bupirimate;
F.IV) Inhibitors of cell division and or cytoskeleton
F.IV-1 ) Tubulin inhibitors: benzimidazoles and thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl;
triazolopyrimidines: 5-chloro-7 (4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)- [1 ,2,4]triazolo[1 ,5 a]pyrimidine;
F.IV-2) Other cell division inhibitors
benzamides and phenyl acetamides: diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide;
F.IV-3) Actin inhibitors: benzophenones: metrafenone; pyriofenone;
F.V) Inhibitors of amino acid and protein synthesis
F.V-1 ) Methionine synthesis inhibitors (anilino-pyrimidines)
anilino-pyrimidines: cyprodinil, mepanipyrim, nitrapyrin, pyrimethanil;
F.V-2) Protein synthesis inhibitors (anilino-pyrimidines)
antibiotics: blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
F.VI) Signal transduction inhibitors
F.VI-1 ) MAP / Histidine kinase inhibitors (e.g. anilino-pyrimidines)
dicarboximides: fluoroimid, iprodione, procymidone, vinclozolin;
phenylpyrroles: fenpiclonil, fludioxonil;
F.VI-2) G protein inhibitors: quinolines: quinoxyfen;
F.VI I) Lipid and membrane synthesis inhibitors
F.VI 1-1 ) Phospholipid biosynthesis inhibitors
organophosphorus compounds: edifenphos, iprobenfos, pyrazophos;
dithiolanes: isoprothiolane;
F.VII-2) Lipid peroxidation: aromatic hydrocarbons: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole; F.VII-3) Carboxyl acid amides (CAA fungicides)
cinnamic or mandelic acid amides: dimethomorph, flumorph, mandiproamid, pyrimorph; valinamide carbamates: benthiavalicarb, iprovalicarb, pyribencarb, valifenalate and N-(1 - (1 -(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester;
F.VII-4) Compounds affecting cell membrane permeability and fatty acids:
1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1 -piperidinyl]-2-[5- methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone, carbamates: propamocarb, propamocarb- hydrochlorid,
F.VII-5) fatty acid amide hydrolase inhibitors: 1 -[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro- 3-isoxazolyl]-2-thiazolyl]-1 -piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]ethanone;
F.VIII) Inhibitors with Multi Site Action
F.VIII-1 ) Inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur;
F.VIII-2) Thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam,
methasulphocarb, metiram, propineb, thiram, zineb, ziram;
F.VIII-3) Organochlorine compounds (e.g. phthalimides, sulfamides, chloronitriles):
anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole and its salts, phthalide, tolylfluanid, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfonamide;
F.VIII-4) Guanidines and other: guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), 2,6- dimethyl-1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone;
F.VIII-5) Anthraquinones: dithianon;
F.IX) Cell wall synthesis inhibitors
F.IX-1 ) Inhibitors of glucan synthesis: validamycin, polyoxin B;
F.IX-2) Melanin synthesis inhibitors: pyroquilon, tricyclazole, carpropamide, dicyclomet, fenoxanil;
F.X) Plant defence inducers
F.X-1 ) Salicylic acid pathway: acibenzolar-S-methyl;
F.X-2) Others: probenazole, isotianil, tiadinil, prohexadione-calcium;
phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts;
F.XI) Unknown mode of action:bronopol, chinomethionat, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover, flusulfamide, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxathiapiprolin, oxin-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3- propylchromen-4-one, N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)- methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N- ethyl-N methyl formamidine, N' (4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N- ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)- phenyl)-N-ethyl-N-methyl formamidine, N'-(5-difluoromethyl-2 methyl-4-(3-trimethylsilanyl- propoxy)-phenyl)-N-ethyl-N-methyl formamidine, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 - yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic acid methyl-(1 ,2,3,4-tetrahydro-naphthalen-1 -yl)- amide, 2-{1 -[2-(5-methyl-3-trifluoromethyl-pyrazole-1 -yl)-acetyl]-piperidin-4-yl}-thiazole-4- carboxylic acid methyl-( ^-1 ,2,3,4-tetrahydro-naphthalen-1 -yl-amide, methoxy-acetic acid 6-tert- butyl-8-fluoro-2,3-dimethyl-quinolin-4-yl ester and N-Methyl-2-{1 -[(5-methyl-3-trifluoromethyl-1 H- pyrazol-1 -yl)-acetyl]-piperidin-4-yl}-N-[(1 ,2,3,4-tetrahydronaphthalen-1 -yl]-4- thiazolecarboxamide, 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine,
pyrisoxazole, 5-amino-2-isopropyl-3-oxo-4-ortho-tolyl-2,3-dihydro-pyrazole-1 carbothioic acid S- allyl ester, N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic acid amide, 5-chloro-1 (4,6- dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chloro-phenyl)-N-[4-(3,4- dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxyacetamide;
F.XI) Growth regulators: abscisic acid, amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid, maleic hydrazide, mefluidide, mepiquat (mepiquat chloride), naphthaleneacetic acid, N 6-benzyladenine, paclobutrazol, prohexadione (prohexadione-calcium), prohydrojasmon, thidiazuron,
triapenthenol, tributyl phosphorotrithioate, 2,3,5 tri iodobenzoic acid, trinexapac-ethyl and uniconazole;
F.XI I) Biological control agents
Ampelomyces quisqualis (e.g. AQ 10® from Intrachem Bio GmbH & Co. KG, Germany),
Aspergillus f/avus (e.g. AFLAGUARD® from Syngenta, CH), Aureobasidium pullulans (e.g.
BOTECTOR® from bio-ferm GmbH, Germany), Bacillus pumi/us (e.g. NRRL Accession No. B-30087 in SONATA® and BALLAD® Plus from AgraQuest Inc., USA), Bacillus subtilis (e.g. isolate NRRL-Nr. B-21661 in RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest Inc., USA), Bacillus subtiHs Mdx. amyloliquefaciens FZB24 (e.g. TAEGRO® from Novozyme Biologicals, Inc., USA), Candida oleophila I-82 (e.g. ASPIRE® from Ecogen Inc., USA), Candida saitoana (e.g. BIOCURE® (in mixture with lysozyme) and BIOCOAT® from Micro Flo Company, USA (BASF SE) and Arysta), Chitosan (e.g. ARMOUR-ZEN from BotriZen Ltd., NZ), Clonostachys rosea f. catenulata, also named Gliocladium catenulatum (e.g. isolate J 1446: PRESTOP® from Verdera, Finland), Coniothyrium minitans (e.g. CONTANS® from Prophyta, Germany), Cryphonectria parasitica (e.g. Endothia parasitica from CNICM, France),
Cryptococcus albidus (e.g. YIELD PLUS® from Anchor Bio-Technologies, South Africa), Fusarium oxysporum (e.g. BIOFOX® from S.I.A.P.A., Italy, FUSACLEAN® from Natural Plant Protection, France), Metschnikowia fructicola (e.g. SHEMER® from Agrogreen, Israel),
Microdochium dimerum (e.g. ANTIBOT® from Agrauxine, France), Phlebiopsis gigantea (e.g. ROTSOP® from Verdera, Finland), Pseudozyma flocculosa (e.g. SPORODEX® from Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (e.g. POLYVERSUM® from Remeslo SSRO, Biopreparaty, Czech Rep.), Reynoutria sachlinensis (e.g. REGALIA® from Marrone Biolnnovations, USA), Talaromyces flavus^^ M (e.g. PROTUS® from Prophyta, Germany), Trichoderma asperellum SKT -1 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.,
Japan), T. atroviride LC52 (e.g. SENTINEL® from Agrimm Technologies Ltd, NZ), T. harzianum T-22 (e.g. PLANTSHIELD® der Firma BioWorks Inc., USA), T. harzianum JH 35 (e.g. ROOT
PRO® from Mycontrol Ltd., Israel), T. harzianum l-39 (e.g. TRICHODEX® and TRICHODERMA
2000® from Mycontrol Ltd., Israel and Makhteshim Ltd., Israel), T. harzianum and T. v/ride (e.g.
TRICHOPEL from Agrimm Technologies Ltd, NZ), T. harzianum ICC012 and T. viride ICC080 (e.g. REMEDIER® WP from Isagro Ricerca, Italy), T. polysporum and T. harzianum (e.g.
BINAB® from BINAB Bio-Innovation AB, Sweden), T. stromaticum {e.g. TRICOVAB® from
C.E.P.L.A.C., Brazil), T. virens GL-2 (e.g. SOILGARD® from Certis LLC, USA), T. viride {e.g.
TRIECO® from Ecosense Labs. (India) Pvt. Ltd., Indien, BIO-CURE® F from T. Stanes & Co.
Ltd., Indien), T. viride ~V^\ (e.g. T. viride TV1 from Agribiotec srl, Italy), Ulocladium oudemansii HRU3 (e.g. BOTRY-ZEN® from Botry-Zen Ltd, NZ).
The commercially available compounds II of the group F listed above may be found in The
Pesticide Manual, 15th Edition, C. D. S. Tomlin, British Crop Protection Council (201 1 ) among other publications. Their preparation and their activity against harmful fungi is known (cf.:
http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their fungicidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031 ;
EP A 226 917; EP A 243 970; EP A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125;
EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP 2002316902; DE 19650197;
DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ;
WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103;
WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804;
WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772;
WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 1 1/028657).
The invertebrate pest, e.g. the insects, arachnids and nematodes, the plant, soil or water in which the plant is growing can be contacted with the present compounds of formula (I), including their stereoisomers and tautomers, as well the salts thereof, or composition(s) containing them by any application method known in the art. As such, "contacting" includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the
compounds/compositions to the locus of the animal pest or plant).
The compounds of formula (I), including their stereoisomers and tautomers, as well the salts thereof, or the pesticidal compositions comprising them may be used to protect growing plants and crops from attack or infestation by animal pests, especially insects, acaridae or arachnids by contacting the plant/crop with a pesticidally effective amount of compounds of formula (I). The term "crop" refers both to growing and harvested crops.
The compounds of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants, such as cereal, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
The compounds of the present invention are employed as such or in form of compositions by treating the insects or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with a insecticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.
The present invention also includes a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one active compound of the formula (I), a stereoisomers, a tautomere or a salt thereof.
Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of compounds of formula (I), a stereoisomer, a tautomere or a salt thereof. As such, the application may be carried out before or after the infection of the locus, growing crops, or harvested crops by the pest.
The compounds of the invention can also be applied preventively to places at which occurrence of the pests is expected.
The compounds of formula (I), including their stereoisomers and their tautomers, as well as their salts may be also used to protect growing plants from attack or infestation by pests. The use includes contacting the plant with a pesticidally effective amount of compounds of formula (I), a stereoisomer, a tautomere or a salt thereof. As such, "contacting" includes both direct contact, i.e. applying the compounds/compositions directly on the pest and/or plant - typically to the foliage, stem or roots of the plant, and indirect contact, i.e. applying the
compounds/compositions to the locus of the pest and/or plant.
"Locus" means a habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest or parasite is growing or may grow.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s) (oligo- or polypeptides) poly for example by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties(e.g. as disclosed in
Biotechnol Prog. 2001 Jul-Aug;17(4):720-8., Protein Eng Des Sel. 2004 Jan;17(1 ):57-66, Nat Protoc. 2007;2(5):1225-35., Curr Opin Chem Biol. 2006 Oct;10(5):487-91 . Epub 2006 Aug 28., Biomaterials. 2001 Mar;22(5):405-17, Bioconjug Chem. 2005 Jan-Feb;16(1 ):1 13-21 ).
The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as
hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e. g. EP-A-0242236, EP-A-242246) or oxynil herbicides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus
thuringiensis, such as a-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such
Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP- glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701 ). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are dis-closed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins protection from harmful pests from certain taxonomic groups of arthropods, particularly to beetles (Coleoptera), flies (Diptera), and butterflies and moths (Lepidoptera) and to plant parasitic nematodes (Nematoda).
The term "cultivated plants" is to be understood also including plants that are, e.g. by the use of recombinant DNA techniques, capable of synthesizing one or more proteins in order to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis-related proteins", also termed PR proteins - see, for example EP-A 0 392 225 -, or plant disease resistance genes - for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum - or T4-lysozym - e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
The term "cultivated plants" is to be understood also including plants that are, e.g. by the use of recombinant DNA techniques, capable of synthesizing one or more proteins to increase the productivity, e. g. bio mass production, grain yield, starch content, oil content or protein content, or to improve tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for ex-ample oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).
The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato).
In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various
compounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound per m2 treated material, desirably from 0.1 g to 50 g per m2.
Insecticidal compositions for use in the impregnation of materials typically contain from
0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.
For use in treating crop plants, the rate of application of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 5 g to 500 g per hectare, more desirably from 5 g to 200 g per hectare.
The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are effective through both contact, e.g. via soil, glass, wall, bed net, carpet, plant parts or animal parts, and ingestion, e.g. via ingestion of bait or plant part.
The compounds of the invention may also be applied against non-crop insect pests, such as ants, termites, wasps, flies, mosquitos, crickets, or cockroaches. For use against said non- crop pests, compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are preferably used in a bait composition.
The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
The bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
For use in bait compositions, the typical content of active ingredient is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound. Formulations of compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, as aerosols, e.g in spray cans, oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents such as lower alcohols, e.g. methanol, ethanol, propanol or butanol, ketones, e.g. acetone, methyl ethyl ketone, paraffin hydrocarbons, e.g. kerosenes or mineral oils, having boiling ranges of approximately 50 to 250°C, dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propellants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
The oil spray formulations differ from the aerosol recipes in that no propellants are used.
For use in spray compositions, the content of active ingredient is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, and their respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
Methods to control infectious diseases transmitted by insects, such as malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis, with compounds of formula (I) or the stereoisomers, tautomers or salts thereof, and with their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. Suitable repellents for example are Ν,Ν-Diethyl-meta-toluamide (DEET), N,N-diethylphenylacetamide (DEPA), 1 -(3-cyclohexan-1 -yl-carbonyl)-2-methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-1 ,3-hexandiol, indalone, Methylneodecanamide (MNDA), a pyrethroid not used for insect control such as {(+/-)-3-allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans- chrysantemate (Esbiothrin), a repellent derived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1 ), (-)-l -epi-eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of aliphatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2- ethylhexylacrylate, and methyl acrylate, mono- and di-ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadiene. The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.
The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, and their compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being, e.g. when the pests invade into houses and public facilities. The compounds of formula (I), their stereoisomers, their tautomers or their salts are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are also suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plant's roots and shoots against soil pests and foliar insects.
The compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, are particularly useful for the protection of the seed from soil pests and the resulting plant's roots and shoots against soil pests and foliar insects. The protection of the resulting plant's roots and shoots is preferred. More preferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.
The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with a compound of the general formula (I), a tautomer, a stereosiomer or a salt thereof. Particularly preferred is a method, wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.
The term seed includes seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
The term seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
The present invention also relates to seeds coated with or containing the active compound of the present invention, i.e. containing a compound of formula (I), a stereoisomer, a tautomer or a salt thereof. The term "coated with and/or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
Suitable seed is seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
In addition, the compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, may also be used for the treatment seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic
engineering methods.
For example, the compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate- ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No.
5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A- 0142924, EP-A-0193259),
Furthermore, the compounds of formula (I), including the tautomers and stereoisomers, as well as their salts, can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant
procedures). For example, a number of cases have been described of recombinant
modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/1 1376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).
The seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
Compositions which are especially useful for seed treatment are e.g.:
A Soluble concentrates (SL, LS)
D Emulsions (EW, EO, ES)
E Suspensions (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)
G Water-dispersible powders and water-soluble powders (WP, SP, WS) H Gel-Formulations (GF)
I Dustable powders (DP, DS)
Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These
formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter
In a preferred embodiment a FS formulation is used for seed treatment. Typcially, a FS formulation may comprise 1 -800 g/l of active ingredient, 1 -200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
Especially preferred FS formulations of a compound of formula (I), a stereoisomer, a tautomer or a salt, for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the the compound of formula (I), including its tautomers and stereoisomers, or a salt thereof, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
Seed Treatment formulations may additionally also comprise binders and optionally colorants.
Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are homo- and copolymers from alkylene oxides like ethylene oxide or propylene oxide, polyvinylacetate, polyvinylalcohols, polyvinylpyrrolidones, and copolymers thereof, ethylene-vinyl acetate copolymers, acrylic homo- and copolymers, polyethyleneamines, polyethyleneamides and polyethyleneimines, polysaccharides like celluloses, tylose and starch, polyolefin homo- and copolymers like olefin/maleic anhydride copolymers, polyurethanes, polyesters, polystyrene homo and copolymers
Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 1 12, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
Examples of a gelling agent is carrageen (Satiagel®) In the treatment of seed, the application rates of the compounds of formula (I) are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed.
The invention therefore also relates to seed comprising a compound of the formula (I), a tautomer, a stereoisomer or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the formula (I) or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are in particular also suitable for being used for combating parasites in and on animals.
An object of the present invention is therfore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.
The invention also relates to compositions containing a parasiticidally effective amount of a compound of formula (I) or a stereoisomer or a tautomer or a veterinarily acceptable salt thereof and an acceptable carrier, for combating parasites in and on animals.
The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) or a stereoisomer or a tautomer or a veterinarily acceptable salt thereof or a composition comprising it.
The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a compound of formula (I) or a stereoisomer or a tautomer or a veterinarily acceptable salt thereof or a composition comprising it.
Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non- emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.
Surprisingly it has now been found that compounds of formula (I), including their stereoisomers and tautomers, and the salts thereof, are suitable for combating endo- and ectoparasites in and on animals.
Compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof, and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals, including humans, and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
Compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.
Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.
The compounds of formula (I) including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are especially useful for combating ectoparasites.
The compounds of formula (I), including their stereoisomers and their tautomers, and the veterinarily acceptable salts thereof are especially useful for combating parasites of the following orders and species, respectively:
fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides cam's, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus;
cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae,
Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Peri plan eta australasiae, and Blatta orien talis;
flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans,
Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pip/ens, Culex nig palpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Derma tobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina pa/pa/is, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris,
Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor,
Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys caicitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus simiiis; lice (Phthiraptera), e.g. Pedicu/us human us capitis, Pedicu/us human us corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephaius sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi,
Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus ga/linae;
Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp.,
Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp.,
Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., and Laminosioptes spp;
Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus;
Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.;
Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp;
Roundworms Nematoda:
Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), ^Trichuridae^ Trichuris spp., Capillaria spp.;
Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp;
Strongylida, e.g. Strongylus spp., Ancyiostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp. , Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanus spp., Chabertia spp., Stephanurus dentatus , Syngamus trachea, Ancyiostoma spp., Uncinaria spp., Giobocephaius spp., Necator spp., Metastrongyius spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale;
Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Para sea ris equorum, Enterobius vermicularis (Threadworm), Toxocara can is, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi;
Camallanida, e.g. Dracunculus medinensis (guinea worm);
Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetaionema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.;
Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp.,
Macracanthorhynchus hirudinaceus and Oncicola spp;
Planarians (Plathelminthes):
Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp.,
Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp.,
Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.
The compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.
Moreover, the use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating mosquitoes is especially preferred.
The use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating flies is a further preferred embodiment of the present invention.
Furthermore, the use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating fleas is especially preferred.
The use of the compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof and compositions containing them for combating ticks is a further preferred embodiment of the present invention.
The compounds of formula (I), including their stereoisomers and their tautomers, and the salts thereof also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).
Administration can be carried out both prophylactically and therapeutically.
Administration of the active compounds is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.
For oral administration to warm-blooded animals, the compounds of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds of the present invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula (I) compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
Alternatively, the compounds of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The compounds of the present invention may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds of the present invention may be formulated into an implant for subcutaneous administration. In addition the compounds of the present invention may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of a compound of the present invention. The compounds of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds of the present invention. In addition, the compounds of the present invention may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
Suitable preparations are:
Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
- Emulsions and suspensions for oral or dermal administration; semi-solid preparations;
Formulations in which the active compound is processed in an ointment base or in an oil-in- water or water-in-oil emulsion base;
Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.
Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl- pyrrolidone, 2-pyrrolidone, and mixtures thereof.
The compounds of the present invention can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.
Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.
Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, solketal, propylencarbonate, and mixtures thereof. It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.
Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. The thickeners employed are the thickeners given above.
Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.
Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.
Suitable solvents are, for example, water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, n-alkylpyrrolidones such as methylpyrrolidone, n- butylpyrrolidone or n-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy- methylene-1 ,3-diox- olane and glycerol formal.
Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.
Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.
Suitable antioxidants are, for example, sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.
Suitable light stabilizers are, for example, novantisolic acid.
Suitable adhesives are, for example, cellulose derivatives, starch derivatives,
polyacrylates, natural polymers such as alginates, gelatin.
Emulsions can be administered orally, dermally or as injections.
Emulsions are either of the water-in-oil type or of the oil-in-water type.
They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.
Suitable hydrophobic phases (oils) are, for example: liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length Cs- Ci2 or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the Cs-C-io fatty acids, fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C16-C18, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C12-C18, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.
Suitable hydrophilic phases are, for example, water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.
Suitable emulsifiers are, for example,
- non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan
monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin; anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt; cation-active surfactants, such as cetyltrimethylammonium chloride.
Suitable further auxiliaries are substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.
Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances,
preservatives, antioxidants, light stabilizers.
Liquid suspending agents are all homogeneous solvents and solvent mixtures.
Suitable wetting agents (dispersants) are the emulsifiers given above.
Other auxiliaries, which may be mentioned, are those given above.
Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.
Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.
Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.
In general, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of a compound of formula (I), a stereoisomer, a tautomer or a salt thereof.
Generally it is favorable to apply the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
Furthermore, the preparations for controlling endoparasites comprise a compound of the present invention usually in concentrations of 10 ppm to 2 per cent by weight, preferably of 0.05 to 0.9 per cent by weight, very particularly preferably of 0.005 to 0.25 per cent by weight.
In a preferred embodiment of the present invention, the compositions comprising the a compound of the present invention are applied dermally / topically.
In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
Generally it is favorable to apply solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of the present invention. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.
The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.
The following abbreviations are used:
TFA: trifluoroacetic acid
EtOAc: ethyl acetate
HPLC: High Performance Liquid Chromatography
MS: Mass spectrometry
MeOH: Methanol
t.R = retention time
The compound examples were characterized by coupled High Performance Liquid Chromatography with mass spectrometry (HPLC/MS) or by their melting point.
HPLC method 1 : Phenomenex Kinetex 1 .7 μηη XB-C18 100A; 50 x 2.1 mm; mobile phase: A: water + 0.1 % trifluoroacetic acid (TFA); B: acetonitrile + 0.1 % TFA; gradient: 5-100% B in 1 .50 minutes; 100% B 0.20 min; flow: 0.8-1.Oml/min in 1.50 minutes at 60°C.
HPLC method 3: Analytical HPLC column 1 : RP-18 column Chromolith Speed ROD (from Merck KgaA, Germany). Elution: acetonitrile + 0.1 % TFA acid/ water + 0.1 % TFA in a ratio of from 5:95 to 95:5 in 5 minutes at 40 °C.
HPLC method 4: Analytical UPLC column Aquity BEH C18, 1 .7 μηι, 2.1 x 50 m; mobile phase A: 0.05% formic acid in water, B: 0.05 % formic acid in acetonitrile. Gradient: time/A%: 0/07, 0.3/97, 3.5/2, 4.8/2, 5/97, 5.01/97; flow: 0.6 ml/min; temp: 35°C.
MS-Method 1 (for HPLC-Methods 1 and 3): ESI positive.
MS-Method 2 (for HPLC-Method 4): quadrupole electrospray ionization, 80 V (positive mode).
Preparation Examples:
Example 1 : Synthesis of 1 -[(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino]- 3-(2,2,2-trifluoroethyl)urea (Compound 1 -1 )
Step 1 : N-[(6-chloro-3-pyridyl)methyl]-N-methyl-acetamide
To a solution of 1 -(6-chloro-3-pyridyl)-N-methyl-methanamine (0.500 g, 3.19 mmol, 1.05 equiv.) and thriethylamine (0.61 mL, 0.45 g, 4.4 mmol, 1.45 equiv.) in dichloromethane (5 mL) was added a solution of acetic anhydride (0.29 mL, 0.31 g, 3.0 mmol, 1.00 equiv.) in
dichloromethane (3 mL) dropwise at 0-5°C. The mixture was allowed to warm to room temperature over night and sequentially washed with aqueous NaOH (1 %, 0°C), water, hydrochloric acid (1 %) and water. The organic layer was dried over sodium sulfate, filtered and concentrated to yield the title compound (0.56 g, 93%).
Characterization by HPLC-MS: 0.690 min, m/z = 199.4
Step 2: 1 -[(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino]-3-(2,2,2- trifluoroethyl)urea
To a solution of N-[(6-chloro-3-pyridyl)methyl]-N-methyl-acetamide (obtained in step 1 of Example 1 , 0.310 g, 1.56 mmol, 1 .00 equiv.) in acetonitrile (10 ml.) was added POCI3 (0.16 ml_, 0.26 g, 1.69 mmol, 1.1 equiv.) and heated at 80°C for 30 min. A suspension of 1 -amino-3- (2,2,2-trifluoroethyl)urea (0.250 g, 1.56 mmol, 1 .00 equiv.) was added and the mixture was heated at this temperature for 5 h. After cooling, NaHC03 (2 equiv.) were added and stirring was continued for 30 min. All solids were filtered off, washed with acetonitrile and the organic layers were combined and evaporated to dryness. Flash chromatography on reverse phase with methanol/water yielded the title compound (50 mg, 9%).
Characterization by H-NMR (400 MHz, CD3OD): 5[delta] = 2.18 (s, 3H), 2.97 (s, 3H), 3.85 (q, 2H), 4.60 (s, 2H), 7.43 (d, 1 H), 7.75 (m, 1 H), 8.27 (s, 1 H).
Characterization by HPLC-MS: 0.694 min, m/z = 337.8
Example 2: Synthesis of E/Z-[1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]-2,2,2-trifluoro- ethylidene]amino] 1 -cyanocyclopropanecarboxylate (Compound I-2) as a mixture of isomers.
Figure imgf000135_0001
Step 1 : [(2,2,2-Trifluoroacetyl)amino] 2,2,2-trifluoroacetate
Hydroxylamine hydrochloride (2.8 g) was placed in a three necked round bottom flask with dry ice condenser. Trifluoroacetic acid chloride (18.62 g) was added at such a rate that no hydrogen chloride evolved. The mixture was stirred over night. All volatiles were removed in vacuum and the residie was dried to yield the title compound (7.63 g, 84%), which was used in the next step as such.
Step 2: [(1 -Chloro-2,2,2-trifluoro-ethylidene)amino] 2,2,2-trifluoroacetate A mixture of [(2,2,2-trifluoroacetyl)amino] 2,2,2-trifluoroacetate from step 1 (7.63 g) and PCIs (7.62 g) was slowly heated to 60°C until the gas evolution ceased. Under reduced pressure, the title compound (6.25 g) distilled at room temperature into a cooled flask and was used in the next step as such.
Step 3: 2,2,2-Trifluoro-N-hydroxy-acetimidoyl chloride
[(1 -Chloro-2,2,2-trifluoro-ethylidene)amino] 2,2,2-trifluoroacetate from step 2 (6.25 g) was placed in a round bottom flask and slowly treated with anhydrous methanol (0.84 g, 1.07 mL) at 0°C. After warming to room temperature, all volatiles were removed in vacuum and the residue contained the title compound (4.0 g, containing impurities) and was used in step 5 directly.
Step 4: 1 -(6-Chloro-3-pyridyl)-N-methyl-methanamine A mixture of 2-chloro-5-(chloromethyl)pyridine (50 g) and methylamine (239.61 g of a 40% solution in water) was dissolved in ethanol (50 mL) and heated at reflux for 5 h. After cooling, the volatiles were removed in vacuum and the residue was taken up in ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate solution, water and brine, dried over sodium sulfate and concentrated in vacuum to obtain the title compound 40 g).
Step 5: N-[(6-Chloro-3-pyridyl)methyl]-2,2,2-trifluoro-N'-hydroxy-N-methyl-acetamidine
To a mixture of 1 -(6-chloro-3-pyridyl)-N-methyl-methanamine from step 4 (3.93 g) and triethyl amine (2.70 g) in dichloromethane (30 mL) was adeded 2,2,2-trifluoro-N-hydroxy-acetimidoyl chloride from step 3 (3.7 g) in dichloromethane (5 mL) at 10-15°C. The mixture was allowed to reach room temperature and stirred over night. Saturared aqueous ammonium chloride was added and the layers were separated. The organic layer was dried over sodium sulfate and concentrated in vacuum. Flash chromatography on reverse phase RP18 with water/methanol yielded the title compound (3.5 g).
H-NMR (400 MHz, CDC ): 5[delta] = 2.81 (s, 3H), 4.45 (s, 2H), 7.34 (d, 1 H), 7.58 (s, 1 H), 7.72 (m, 1 H), 8.36 (m, 1 H).
Step 6: E/Z- 1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]-2,2,2-trifluoro-ethylidene]amino] 1 - cyanocyclopropanecarboxylate (Compound I-2)
To a solution of 1 -cyanocyclopropanecarboxylic acid (70 mg) in dichloromethane (10 mL) was added 1 -chloro-N,N,2-trimethyl-prop-1 -en-1 -amine (90 mg) at room temperature and stirred for 90 min. To this mixture, a solution of N-[(6-chloro-3-pyridyl)methyl]-2,2,2-trifluoro-N'-hydroxy-N- methyl-acetamidine from step 5 (0.15 g) in dichloromethane (2 mL) was added and the solution was stirred over night. Water was added and the layers were separated. The organic layer was dried over sodium sulfate and concentrated in vacuum. The residue was purified via column chromatography on silica gel with ethyl acetate and cyclohexane to yield the title compound 90 mg, 46%).
H-NMR (400 MHz, CDCI3): 5[delta] = 1 .72 (m, 2H), 1 .80 (m, 2H), 2.82 and 3.12 (2xs, 3H), 4.48 and 4.72 (2xs, 2H), 7.34 and 7.38 (2xd, 1 H), 7.60 and 7.75 (2xm, 1 H), 8.35 (m, 1 H). The E/Z-isomers were not assigned.
Example 3: Synthesis of [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino] 2- cyanoacetate (compound I-6)
Figure imgf000137_0001
Step 1 : N-[(6-chloro-3-pyridyl)methyl]-N'-hydroxy-N-methyl-acetamidine
The title compound was prepared in analogy to N-[(6-chloro-3-pyridyl)methyl]-2,2,2-trifluoro-N'- hydroxy-N-methyl-acetamidine using 1 -(6-chloro-3-pyridyl)-N-methyl-methanamine and N- hydroxy-acetimidoyl chloride.
HPLC-MS: 1 .12 min, m/z = 214.4 (method 4)
Step 2: [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino] 2-cyanoacetate A portion of 2-cyanoacetic acid (175 mg) was suspended in dichloromethane (10 mL). To this mixture, 1 -chloro-N,N,2-trimethyl-prop-1 -en-1 -amine (Ghosez's reagent, 300 mL, 300 mg) was added dropwise and the mixture turned into a red solution. After 1.5 h at room temperature, a solution of N-[(6-chloro-3-pyridyl)methyl]-N'-hydroxy-N-methyl-acetamidine (400 mg) in dichloromethane (5 mL) was added and kept at this temperature for 12 h. Water was added and the layers were separated. The organic layer was dried over sodium sulfate and concentrated in vacuum. Flash chromatography on silica gel yielded the title compound (180 mg).
H-NMR (400 MHz, CDC ): 5[delta] = 2.17 (s, 3H), 2.93 (s, 3H), 3.56 (s, 2H), 4.51 (s, 2H), 7.32 (d, 1 H), 7.71 (m, 1 H), 8.32 (s, 1 H).
Example 4: Synthesis of [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino] 2- cyano-2-methyl-propanoate (compound I-7)
Figure imgf000137_0002
Following an analogous procedure as described above for [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl- methyl-amino]ethylideneamino] 2-cyanoacetate (compound I-6) using 2-cyano-2-methyl- propanoic acid as coupling agent, the title compound was obtained.
H-NMR (400 MHz, CDCI3): 5[delta] = 2.18 (s, 3H), 2.94 (s, 6H), 3.06 (s, 3H), 4.51 (s, 2H), 7.32 (d, 1 H), 7.74 (m, 1 H), 8.32 (s, 1 H).
Example 5: Synthesis of [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl-methyl-amino]ethylideneamino] ( -2-cyano-2-methoxyimino-acetate (compound I-8)
Figure imgf000138_0001
Following an analogous procedure as described above for [(E/Z)-1 -[(6-chloro-3-pyridyl)methyl- methyl-amino]ethylideneamino] 2-cyanoacetate (compound I-6) using potassium salt of 2- cyano-2-methoxyimino-acetate as coupling agent, the title compound was obtained.
H-NMR (400 MHz, CDC ): 5[delta] = = 2.19 (s, 3H), 2.97 (s, 3H), 4.33 (s, 3H), 4.53 (s, 2H), 7.31 (d, 1 H), 7.75 (m, 1 H), 8.31 (m, 1 H).
The compounds of formula (l-A) (i.e. compounds of formula I , where Het is 6-chloropyridin-3-yl, R1 = R2 = H) summarized in table C.1 below can be prepared in analogy to the methods described above
Figure imgf000138_0002
Table d
m/z
No. R3a R3b Y tR [min] method
[M+H]+
1-1 CHs CHs 2,2,2-trifluoroethylcarbamoylamino 0.694 337.8 1
I-2 CHs CFs (l -cyanocyclopropanecarbonyl)oxy 2.960 361 .1 3
I-3 CHs CHs acetoxy 2.09 256.4 4
I-4 CHs CHs (l -cyanocyclopropanecarbonyl)oxy 2.36 307.4 4
I-5 CHs CHs (2-methoxyiminoacetyl)oxy 1 .83 299.3 4 m/z
No. R3a R3b Y tR [min] method
[M+H]+
I-6 CHs CHs (2-cyanoacetyl)oxy 0.848 280.9 1
I-7 CHs CHs (2-cyano-2-methyl-propanoyl)oxy 0.979 309.0 1
I-8 CHs CHs (2-cyano-2-methoxyimino-acetyl)oxy 1 .019 323.9 1
I-9 CHs CHs 2,2,2-trifluoroethylcarbamoyloxy 2.44 339.5 4
1-10 CHs CHs ethylcarbamoyloxy 2.17 285.5 4
1-1 1 CHs CFs acetamido 1 .85 309.1 4
1-12 CHs CFs tert-butoxycarbonylamino 3.01 367.2 4
1-13 CHs CFs 2,2-dimethylpropanoylamino 2.60 351 .3 4
B Biological Examples
The biological activity of the compounds of formula I of the present invention may be evaluated in biological tests as described in the following.
General conditions: If not otherwise specified, most test solutions are to be prepared as follows: The active compound is to be dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water:acteon. Further, the test solutions are to be prepared at the day of use (and, if not otherwised specified, in general at concentrations wt/vol).
B.1 Green Peach Aphid (Myzus persicae)
For evaluating control of green peach aphid {Myzus persicae) through systemic means, the test unit consists of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.
The compounds are formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds are pipetted into the aphid diet, using a custom built pipetter, at two replications.
After application, 5 - 8 adult aphids are placed on the artificial membrane inside the microtiter plate wells. The aphids are then allowed to suck on the treated aphid diet and incubated at about 23 + 1 °C and about 50 + 5 % relative humidity for 3 days. Aphid mortality and fecundity is then visually assessed.
In this test, compounds , I-6, I-7, I-8 and 1-10 at 2500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.2 Vetch aphid (Megoura viciae)
The active compounds were formulated in 3:1 (vohvol) water : DMSO with different concentrations of formulated compounds.
Bean leaf disks were placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf disks were sprayed with 2.5 μΙ of the test solution and 5 to 8 adult aphids were placed into the microtiter plates which were then closed and kept at 23 ± 1 °C and 50 ± 5% relative humidity under fluorescent light for 6 days. Mortality was assessed on the basis of vital, reproduced aphids. Aphid mortality and fecundity was then visually assessed.
In this test, compounds I-4, I-5, I-6 and I-8 at 2500 ppm showed at least 75% mortality in comparison with untreated controls.
B.3 Cotton aphid {Aphis gossypii)
The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in 1 .3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 1 :1 (vohvol) water : aceton. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v).
Cotton plants at the cotyledon stage were infested with aphids prior to treatment by placing a heavily infested leaf from the main aphid colony on top of each cotyledon. Aphids were allowed to transfer overnight to accomplish an infestation of 80-100 aphids per plant and the host leaf was removed. The infested plants were then sprayed by an automated
electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed from the sprayer, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at 25°C and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.
In this test, compound I-8 at 300 ppm showed at least 75 % mortality in comparison with untreated controls. B.4 Cowpea aphid {Aphis craccivora)
The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1 % (vol/vol). The test solution is prepared at the day of use.
Potted cowpea plants are colonized with approximately 50 - 100 aphids of various stages by manually transferring a leaf tissue cut from infested plant 24 hours before application. Plants are sprayed after the pest population has been recorded. Treated plants are maintained on light carts at about 28°C. Percent mortality is assessed after 72 hours.
In this test, compounds I-6, I-7 and I-8 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.5 Orchid thrips (dichromothrips corbetti)
Dichromothrips corbetti a6u\\s used for bioassay are obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1 :1 mixture of acetone:water (vohvol), plus 0.01 % vol/vol Alkamuls® EL 620 surfactant.
Thrips potency of each compound is evaluated by using a floral-immersion technique.
Plastic petri dishes are used as test arenas. All petals of individual, intact orchid flowers are dipped into treatment solution and allowed to dry. Treated flowers are placed into individual petri dishes along with about 20 adult thrips. The petri dishes are then covered with lids. All test arenas are held under continuous light and a temperature of about 28°C for duration of the assay. After 3 days, the numbers of live thrips are counted on each flower, and along inner walls of each petri dish. The percent mortality is recorded 72 hours after treatment.
In this test, compound I-8 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.6 Rice green leafhopper (Nephotettix virescens)
Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds are formulated in 50:50 acetone:water (vohvol), and 0.1 % vol/vol surfactant (EL 620) is added.
Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.
In this test, compounds I-6 and I-8 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.7 Rice brown plant hopper (Nilaparvata lugens)
Rice seedlings are cleaned and washed 24 hours before spraying. The active compounds is formulated in 50:50 acetone:water (vohvol) and 0.1 % vol/vol surfactant (EL 620) was added. Potted rice seedlings are sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants are kept at about 28-29°C and relative humidity of about 50-60%. Percent mortality is recorded after 72 hours.
In this test, compound 1-1 1 at 500 ppm showed at least 75 % mortality in comparison with untreated controls.
B.8 Boll weevil {Anthonomus grandis)
The compounds were formulated in 3:1 (vohvol) water : DMSO.
For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24- well-microtiter plates containing an insect diet and 20-30 A. grandis eggs. Different
concentrations of formulated compounds were sprayed onto the insect diet at 20 μΙ, using a custom built micro atomizer, at two replications. After application, the microtiter plates were incubated at 23 ± 1 °C and 50 ± 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
In this test, compounds I-8 and 1-10 at 2500 ppm showed at least 75% mortality in comparison with untreated controls.
B.9 Diamond back moth (Plutella xylostella) The active compound is dissolved at the desired concentration in a mixture of 1 :1 (vohvol) distilled water : aceteone. Surfactant (Kinetic HV) is added at a rate of 0.01 % (vol/vol).The test solution is prepared at the day of use. Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0- 100%. B.10 Mediterranean fruitfly ( Ceratitis capitata)
For evaluating control of Mediterranean fruitfly {Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed. B.1 1 Silverleaf whitefly (Bemisia argentifolii)
The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects. Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was pla-ced into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants. B.12 Southern armyworm {Spodoptera eridania), 2nd instar larvae
The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 5 or 10ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01 % (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.
Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1 st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 1 1 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25°C and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
B.13 Tobacco budworm {Heliothis virescens)
For evaluating control of tobacco budworm {Heliothis virescens) the test unit consisted of 96- well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.
The compounds were formulated using a solution containing 75% v/v water and 25% v/v
DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at about 28 + 1 °C and about 80 + 5 % relative humidity for 5 days. Egg and larval mortality was then visually assessed.
B.14 Yellow fever mosquito (Aedes aegypti)
For evaluating control of yellow fever mosquito {Aedes aegypti) the test unit consisted of 96- well-microtiter plates containing 200μΙ of tap water per well and 5-15 freshly hatched A. aegypti larvae.
The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5μΙ, using a custom built micro atomizer, at two replications.
After application, microtiter plates were incubated at 28 + 1 °C, 80 + 5 % RH for 2 days. Larval mortality was then visually assessed.

Claims

Claims
1 . A compound of formula (I):
Figure imgf000144_0001
wherein
Y is a radical Y , Y2, Y3, Y4 or Y5, where
Y1 is 0-C(=X)-R4;
Y2 is S-C(=X)-R4;
Y3 is N(R5a)-C(=X)-R4;
Y4 is N(R5a)-S(=0)-R5b;
Y5 is N(R5a)-S(=0)2-R5b; and where X is O or S; is a 5- or 6-membered carbon-bound or nitrogen-bound, saturated, partly unsaturated or aromatic heterocyclic radical comprising 2, 3, 4 or 5 carbon atoms and 1 , 2 or 3 heteroatoms as ring members, which are independently selected from sulfur, oxygen and nitrogen, wherein the sulfur and nitrogen ring members can independently be partly or fully oxidized, and wherein each ring is optionally substituted by k identical or different substituents R6, wherein k is an integer selected from 0, 1 , 2, 3 or 4; are independently from each other selected from the group consisting of hydrogen, halogen, CN, SCN, nitro, Ci-C6-alkyl, C3-C6-cycloalkyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7
Si(R11)2R12, OR8, OS02R8a, S(0)nR8a, S(0)nNR9aR9b, NR9aR9b, C(=0)NR9aR9 , C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a, phenyl, benzyl, where the phenyl ring in the last two radicals is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
R1 and R2 form, together with the carbon atom, which they attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring, wherein each of the carbon atoms of said cycle are unsubstituted or may carry any combination of 1 or 2 identical or different radicals R7, or
R and R2 may together be =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9b; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any
combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10,
NR9aR9b, C(=0)NR9aR9b, C(=S)NR9aR9b, OR8, S(0)nR8a, C(=0)OR8, C(=0)R7a, C(=S)R7a,
Cyc1-Q1, where
Cyc1 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q1 is Ci-C4-alkanediyl or C2-C4-alkenediyl; R3b is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R10,
OR8, S(0)nR8a, C(=N-0-R16a)R15,
Cyc2-Q2, where
Cyc2 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q2 is Ci-C4-alkanediyl or C2-C4-alkenediyl;
R4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, S(0)nR8a, S(0)nNR9aR9b, NR18aR18b, C(=0)NR9aR9b, C(=S)NR aR , C(=0)OR8, C(=0)R7a, C(=S)R7a, and
Cyc3-Q3, where
Cyc3 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,and where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
Q3 is a single bond, Ci-C4-alkanediyl or C2-C4-alkenediyl; R4 and R5a, if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the two aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b;
R5a if present, is selected from the group consisting of hydrogen, OH, CN, C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3- C8-cycloalkyl-Ci-C4-alkoxy, wherein each of the 10 last mentioned radicals are unsubstituted, partly or completely halogenated,
C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10;
R5b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl,
C2-C6-alkynyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Si(R11)2R12, OR8, NR9aR9 , C(=0)NR9aR9 , C(=S)NR9aR9 , C(=0)OR8, C(=0)R7a, C(=S)R7a,
Cyc4-Q4, where
Cyc4 is phenyl or a 3-, 4-, 5-, 6- or 7-membered, saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the phenyl ring and the heterocyclic ring are unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Q4 is Ci-C4-alkanediyl or C2-C4-alkenediyl; or
R5a and R5b, if present, together may also form a bivalent radical, selected from the group consisting of C2-C6-alkanediyl and C2-C6-alkenediyl, wherein the carbon atom in the two aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R7b; where, independently of their occurrence, n is 0, 1 or 2; R6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF5, Ci-
Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, and wherein the carbon atoms of the last 4 aliphatic and cycloaliphatic radicals may be partially or completely halogenated and/or further substituted independently from one another with 1 , 2 or 3 radicals R7,
OR8, NR17aR17b, S(0)nR8a, S(0)nNR 7aR 7b, C(=0)R7a, C(=0)NR 7aR 7b, C(=0)OR8,
C(=S)R7a, C(=S)NR 7aR 7b, C(=S)OR8, C(=S)SR8a, C(=NR 7)R7a, C(=NR 7)NR 7aR 7 , Si(R11)2R12;
phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents
R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R6 present on one ring carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b,
or two R6 together form a linear C2-C7-alkylene chain, thus forming, together with the ring atom(s) to which they are bound, a 3-, 4-, 5-, 6-, 7- or 8-membered ring, where 1 or 2 CH2 moieties of the alkylene chain may be replaced by 1 or 2 heteroatom moieties selected from O, S and NR17c and/or 1 or 2 of the CH2 groups of the alkylene chain may be replaced by a group C=0, C=S and/or C=NR17; and where the alkylene chain is unsubstituted or may be substituted with 1 , 2, 3, 4, 5 or 6 radicals selected from the group consisting of halogen, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-
Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, phenyl which may be substituted with 1 , 2, 3, 4 or 5 radicals R10, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 radicals R10;
R7 independently of its occurrence, is selected from the group consisting of cyano, azido, nitro, -SCN, SF5, d-C6-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl,
Si(R11)2R12, OR8, OS02R8a, S(0)nR8a, S(0)nNR 7aR 7 , NR17aR17b, C(=0)NR 7aR 7 , C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15, C(=S)R15, C(=NR 7)R15, NR 7a-C(=0)R7a, NR 7a-C(=S)R7a, NR 7a-C(=0)OR8, NR 7a-C(=0)NR 7aR 7b,
phenyl, phenoxy, phenyl-Ci-C4-alkyl, where the phenyl ring in the last three groups is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two R7 present on one carbon atom may together form =0, =CR13R14, =S, =NR17, =NOR16 or =NNR9aR9b,
or two R7 may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring together with the carbon atoms to which the two R7 are bonded, where the heterocyclic ring comprises 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10; independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C6- cycloalkyl-Ci-C4-alkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, C2-C6 haloalkynyl,
phenyl, benzyl, where the phenyl ring in the two last-mentioned radicals is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; independently of its occurrence, is selected from the group consisting of halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or two of R7b present on one carbon may together form =0, =CR13R14, =S, =NR17, =NOR16, =NNR9aR9b; independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, C(=0)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR16,
phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, independently of its occurrence, is selected from the group consisting of hydrogen, d-Ce-alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, phenyl, phenyl-Ci-C-4-alkyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
a 5- or 6-membered aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10;
R9b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3- C8-cycloalkyl-Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2- C6-haloalkynyl,
S(0)nR16, -S(0)nNR 7aR 7 , C(=0)R15, C(=0)OR16, C(=0)NR 7aR 7 , C(=S)R15, C(=S)SR16, C(=S)NR 7aR 7 , C(=NR 7)R15; phenyl, benzyl, 1 -phenethyl or 2-phenethyl, where the phenyl ring in the last four mentioned radicals is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10; and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C- bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R9a and R9b are together a C2-C7 alkylene-chain and form a 3-, 4-, 5-, 6-, 7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyI, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or
R9a and R9b together may form =CR13R14, =NR17 or =NOR16 moiety; R10 independently of its occurrence, is selected from the group consisting of halogen, cyano, azido, nitro, SCN , SF5, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the carbon atoms of the aforementioned aliphatic and cycloaliphatic radicals may optionally be substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF5, OH, CN , NO2, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci- C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl,
Cs-Cs-cycloalkyI, which is unsubstituted or carries 1 , 2, 3, 4 or 5 identical or different radicals selected from the group consisting of halogen, azido, SCN , SF5, OH, CN , NO2, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,
Si(R11)2R12, OH, SH, OR16, OS(0)nR16a, -S(0)nR16a, S(0)nNR 7aR 7b, NR17aR17b, C(=0)R15, C(=S)R15, C(=0)OR16, -C(=NR 7)R15, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl,
Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)- amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents selected independently from one another from halogen, OH, CN, NO2, SCN, SF5, OH, C1-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
two R10 present together on one carbon ring atom of a saturated or partly unsaturated heterocyclic radical may form =0, =CR13R14, =S, =NR17, =NOR16, =NNR17aR17b;
or,
two R10 on adjacent carbon ring atoms may also be a bivalent radical selected from CH2CH2CH2CH2, CH=CH-CH=CH, N=CH-CH=CH, CH=N-CH=CH, N=CH-N=CH, OCH2CH2CH2, OCH=CHCH2, CH2OCH2CH2, OCH2CH2O, OCH2OCH2, CH2CH2CH2 CH=CHCH2, CH2CH2O, CH=CHO, CH2OCH2, CH2C(=0)0, C(=0)OCH2, 0(CH2)0, SCH2CH2CH2, SCH=CHCH2, CH2SCH2CH2, SCH2CH2S, SCH2SCH2, CH2CH2S, CH=CHS, CH2SCH2, CH2C(=S)S, C(=S)SCH2, S(CH2)S, CH2CH2NR17, CH2CH=N, CH=CH-NR17, OCH=N , SCH=N and form together with the carbon atoms to which the two R10 are bonded to a 5-membered or 6-membered partly saturated or unsaturated, aromatic carbocyclic or heterocyclic ring, wherein the ring may optionally be substituted with one or two substituents selected from =0, OH, CH3, OCH3, halogen, cyano, halomethyl and halomethoxy;
R11 , R12 independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-Cs-halocycloalkyl-Ci-C4- alkyl, Ci-C6-haloalkoxy-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-
C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci- C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R13, R14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and benzyl; R15 independently of its occurrence, is selected from the group consisting of hydrogen,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4 alkoxy;
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-Ce- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R16 independently of its occurrence, is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals R7, phenyl, benzyl, 5- or 6-membered hetaryl or 5- or 6-membered hetaryl-methyl, wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, d-Ce-alkyl, Cs-Ce-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;
R16a independently of its occurrence, is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from C1-C4 alkoxy,
phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH,
Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R17 independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, wherein the 1 1 last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl, phenoxy, benzyloxy and pyridyloxy, wherein the six last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-Ce-alkyI, C3-C6-cycloalkyl, Ci-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylthio, trimethylsilyl, triethylsilyl, te/ibutyldimethylsilyl,
Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF5, OH, Ci-Ce-alkyI, Cs-Ce-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen,
OH , CN , N02, SCN , SF5, OH , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl,
or,
R17a and R17b may together be a C2-C6 alkylene chain forming a 3- to 7- membered saturated, partly saturated or unsaturated ring together with the nitrogen atom R17a and R17b are bonded to, wherein the alkylene chain may contain 1 or 2 heteroatoms selected, independently of each other, from oxygen, sulfur and nitrogen, and may optionally be substituted with halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; or
R17a and R17b together may form =CR13R14, =N R17 or =NOR16 moiety;
R17c independently of its occurrence, is selected from the group consisting of hydrogen, CN , d-Ce-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-Ci- C4-alkyl, wherein the five last mentioned aliphatic and cycloaliphatic radicals may be unsubstituted, partially or fully halogenated and/or oxygenated and/or may carry
1 or 2 radicals selected from C1-C4 alkoxy, phenyl, benzyl and pyridyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH , CN , NO2, SCN , SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; R18a, R18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein each of the four aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, OR16, S(0)nR16a, -S(0)nN R 7aR 7b, C(=0)R15, C(=0)OR16, C(=0)N R 7aR 7b, C(=S)R15, C(=S)SR16a, C(=S)N R 7aR 7b, C(=N R 7) R15; phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 ,
2,
3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
or,
R18b are together a C2-C7-alkylene chain and form a 3-,
4-,
5-,
6-,
7- or 8- membered saturated, partly unsaturated or aromatic ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C3-C8-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6 haloalkynyl, phenyl, optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; the stereoisomers, tautomers and the salts thereof.
The compound of claim 1 , wherein
Het is selected from the group consisting of radicals of the following formula Het-1 to Het-24:
Figure imgf000156_0001
Het-1 Het-2 Het-3 Het-4 Het-5
Figure imgf000157_0001
Het-6 Het-7 Het-9 Het-10
Figure imgf000157_0002
Het-11 Het-12 Het-13 Het-14 Het-15
Figure imgf000157_0003
Het-16 Het-17 Het-18 Het-19 Het-20
Figure imgf000157_0004
Het-21 Het-22 Het-23 Het-24 wherein # denotes the bond in formula (I), and wherein
k is 0, 1 or 2; and
R6A is hydrogen or has one of the meanings given for R6 and
R6B is hydrogen, Ci-C4-alkyl or Ci-C4-haloalkyl.
The compound of claim 2, wherein
Het is selected from the group consisting of radicals of formulae Het-1 , Het-1 1 a and Het-24,
Figure imgf000157_0005
Het-1 Het-11a Het-24
wherein # denotes the bond in formula (I), and wherein R6 is selected from halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and C1-C4- haloalkyl;
R6a is selected from hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and
Ci-C4-haloalkyl; and
k is 0, 1 or 2.
The co , wherein Het is Het-1 a
Figure imgf000158_0001
Het-1a
wherein # denotes the bond in formula (I),
R6 is selected from halogen, Ci-C4-alkyl and Ci-C4-haloalkyl and
R6a is hydrogen or halogen, in particular hydrogen.
The compound of any of the preceding claims, wherein
R1 , R2 are independently from each other selected from the group consisting of hydrogen, halogen, CN , Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, C3-C6- halocycloalkyl;
or
R1 and R2 may together be =CR13R14;
or
R1 and R2 form, together with the carbon atom, which they attached to, a 3- to
5-membered saturated carbocyclic ring,
and wherein both R1 and R2 are in particular hydrogen.
The compound of any of the preceding claims, wherein
R3a is Ci-C6-alkyl, Ci-C6-haloalkyl, where the two radicals may carry 1 , 2 or 3 further radicals R7, which are selected from NO2, cyclopropyl, CN and Ci-C6-alkoxy, which is unsubstituted, partly or completely halogenated, or
C3-C6-cycloalkyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen and Ci-C4-alkyl,
in particular methyl, ethyl, difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, cyclopropyl, cyclopropylmethyl, CH2CN, CH2CH2CN, CH2NO2 and
The compound of any of the preceding claims, wherein
R3b is Ci-C6-alkyl or Ci-C6-haloalkyl, where the two radicals may carry 1 , 2 or 3 further radicals R7, which are, independently of each other, selected from the group consisting of NO2, CN, C3-C6-cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, =N-0-Ci- C4-alkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl, where the last three radicals are unsubstituted, partly or completely halogenated.
8. The compound of claim 7, wherein
R3b is selected from the group consisting of methyl, ethyl, difluoromethyl and
trifluoromethyl.
9. The compound of any of the preceding claims, where in the radicals Y1, Y2 and Y3
R4 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R7,
C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
OR8, NR18aR18b, C(=0)NR9aR9b, C(=S)NR9aR9b, C(=0)OR8, C(=0)R7a,
C(=S)R7a,
phenyl, which is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized.
10. The compound of claim 9, wherein
R4 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C2-C4-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
OR8, NR18aR18b,
C3-C6-cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
phenyl, which is unsubstituted or optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10, and
a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or aromatic heterocyclic ring comprising 1 , 2 or 3 identical or different heteroatoms as ring members, which are selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, where, irrespectively of their occurrence,
R7 is selected from the group consisting of CN, nitro, OH, Ci-C4-alkoxy, Ci- C4-haloalkoxy, C3-C6-cycloalkyl, S(0)nR8a, S(0)nNR 7aR 7 , NR17aR17b, C(=0)NR 7aR 7b, C(=S)NR 7aR 7b, C(=0)OR8, C(=0)R15,
NR 7a-C(=0)R7a, NR 7a-C(=0)OR8, NR 7a-C(=0)NR 7aR 7 , phenyl and phenoxy, where the phenyl ring in the last two mentioned radicals is unsubstituted or carriers 1 , 2, 3, 4 or 5 radicals R10, or
two R7 present on one carbon atom may together form =NOR16 or =N- NR9aR9b;
R7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R10,
phenylcarbonyl, phenoxycarbonyl and phenylaminocarbonyl, wherein the last three radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, d-Ce-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and
phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and
phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
NR9aR9b may also be a saturated N-bound 3-, 4-, 5- or 6-membered
heterocycle, which in addition to the nitrogen atom may have 1 further heteroatom as ring members, which is selected from O and N and where the N-bound 3-, 4-, 5- or 6-membered heterocycle may be unsubstituted or carry 1 , 2, 3 or 4 radicals selected from Ci-C4-alkyl and Ci-C4- haloalkyl;
R10 is selected from the group consisting of halogen, CN, OH, SH, Ci-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0),
Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4- haloalkylsulfonyl, SO2NH2, Ci-C4-alkylaminocarbonyl and di-(Ci-C4- alkyl)aminocarbonyl or two R10 present on one carbon atom may together form =NOR16 or =N-NR17aR17b;
R15 is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from the group consisting of halogen, CN, NO2, C1-C4- alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4 haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl, (Ci- C4-alkyl)amino and di-(Ci-C4-alkyl)amino;
R16 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R7, which are selected from the group consisting of NO2, CN, OR8, S(0)nR8a, NR17aR17b, C(=0)NR 7aR 7b, C(=0)OR8, C(=0)R15 and NR 7a-C(=0)R7a, and
benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;
R17a, R17b are each independently from one another selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substitutents is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from the group consisting of halogen, CN, N02, Ci-C4-alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylsulfonyl, (Ci-C4-alkyl)amino and di-(Ci-C4- alkyl)amino;
R18a, R18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7, C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or
5 identical or different substituents R10,
Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), C1-C4- alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, NH2-S(0)2, C1-C4- alkylsulfonyl, Ci-C4-haloalkylsulfonyl, Ci-C4-alkylaminosulfonyl, di-(Ci- C4-alkyl)aminosulfonyl,
phenyl, which is unsubstituted or carry 1 , 2, 3 or 4 radicals R10, phenoxy, which is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6- cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
and a 5- or 6-membered aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10,
or,
R18a and R18b are together a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7-membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio and Ci-C6-haloalkylthio.
The compound of claim 10, wherein
R4 is selected from the group consisting of
Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R7, where R7 is selected from CN, NO2, Ci-C4-alkoxy, Ci-C4-haloalkoxy, S(0)nR8a and S(0)nNR 7aR 7b,
6-membered heteroaryl selected from the group consisting of pyridinyl, pyrimidinyl, pyrazinyl and pyridazinyl, wherein 6-membered heteroaryl is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, CN, NO2, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy,
the radicals of formula R-41 and R-42:
Figure imgf000162_0001
R-41 R-42
wherein # indicates the bond to the carbonyl group in formula (I) A is CH2, CH2CH2 or CH2CH2CH2,
Rioaa js hydrogen, halogen, S(0)nR16a, CN or N02 and
n is 0, 1 or 2;
the radical of formula R-43
Figure imgf000163_0001
R-43
wherein # indicates the bond to the carbonyl group in formula (I)
Rx is hydrogen, halogen, CN, N02, Ci-C4-alkyl, Ci-C4-haloalkyl, NR17aR17b,
S(0)2NR 7aR 7 , S(0)2R8a or C(=0)OR8;
R16 is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, where the two aforementioned radicals are unsubstituted, partly or completely halogenated and/or may carry 1 or 2 radicals R7, which are selected from the group consisting of N02, CN, OR8, S(0)nR8a, NR17aR17b, C(=0)NR 7aR 7b, C(=0)OR8, C(=0)R15 and NR 7a-C(=0)R7a, and
benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; and the radical NR18aR18b, wherein
R18a, R18b are each independently from one another selected from the group
consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, wherein each of the two aforementioned radicals are unsubstituted, partly or completely halogenated or may carry any combination of 1 , 2 or 3 radicals R7,
C3-Cio-cycloalkyl, which is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10,
Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4- alkyl)aminocarbonyl, NH2-S(0)2, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl,
Ci-C4-alkylaminosulfonyl, di-(Ci-C4-alkyl)aminosulfonyl, phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10,
phenoxy, which may be unsubstituted or may carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6- cycloalkyi, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-
C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl,
and a 5- or 6-membered aromatic C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms as ring members, which are identical or different and selected from oxygen, nitrogen and sulfur, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 identical or different substituents R10,
or,
R18a and R18b are together a C2-C6-alkylene chain and form a 3-, 4-, 5-, 6- or 7- membered saturated ring together with the nitrogen atom they are bonded to, wherein the alkylene chain may contain one or two heteroatoms, which are, independently of each other, selected from oxygen, sulfur and nitrogen, and where the alkylene chain may optionally be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci- C6-haloalkoxy, Ci-C6-alkylthio and Ci-C6-haloalkylthio; where, irrespectively of their occurrence,
R7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last two mentioned radicals is
unsubstituted or carries 1 , 2, 3 or 4 radicals R10; phenylcarbonyl,
phenoxycarbonyl and phenylaminocarbonyl where the phenyl ring in the last three mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4
substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, d-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (C1-C6- alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
R8a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and
phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R10 is selected from the group consisting of halogen, CN, OH , SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, C1-C4- alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl, or
two R10 present on one carbon atom may together form =NOR16; R15 is selected from the group consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N02, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6 haloalkoxy, (Ci-C6-alkyl)carbonyl and (Ci-C6-alkoxy)carbonyl;
R16a is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl and
phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6- alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (C1-C6- alkoxy)carbonyl;
R17a, R17b are each independently from one another selected from the group
consisting of hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, phenyl and benzyl, where the phenyl ring in the last two substituents is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkyl)carbonyl and (C1-C6- alkoxy)carbonyl.
The compound of any of the preceding claims, where in the radicals Y3, Y4 and Y5,
R5a if present, is selected from the group consisting of hydrogen, OH, Ci-C6-alkyl,
Ci-C6-alkoxy, C2-C6-alkenyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein each of the six last mentioned radicals are unsubstituted, partly or completely halogenated,
C(=0)OR8, C(=0)R7a, C(=S)R7a,
phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10.
The compound of claim 12, wherein
R5a if present, is selected from the group consisting of hydrogen, OH, Ci-C6-alkyl,
Ci-C6-alkoxy, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein each of the three last mentioned radicals are unsubstituted, partly or completely halogenated, C(=0)OR8, C(=0)R7a and C(=S)R7a,
where, irrespectively of their occurrence,
R7a is selected from the group consisting of hydrogen, Ci-C4-alkyl, C1-C4- haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R10;
R8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci- C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl, NH2-C(0), Ci-C4-alkylaminocarbonyl, di-(Ci-C4-alkyl)aminocarbonyl, phenyl, benzyl, , where the phenyl ring in the last two mentioned radicals is unsbustituted or carries 1 , 2, 3 or 4 radicals R10, phenylcarbonyl, phenoxycarbonyl and phenylaminocarbonyl, where the phenyl ring in the last three mentioned radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, N02, SCN, SF5, OH, Ci-C6- alkyl, C3-C6-cycloalkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, d-Ce-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (C1-C6- alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
14 The compounds of any of the preceding claims, wherein Y is Y1. 15 The compounds of claims 1 to 13, wherein Y is Y3. 16 The compound of any of claims 1 to 8, 12 or 13, where in the radicals Y4 and Y5,
R5b is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C3-C8- cycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, wherein each of the five last mentioned radicals are unsubstituted, partly or completely halogenated, phenyl and phenyl-Ci-C4-alkyl, where the phenyl ring in the last two mentioned groups is unsubstituted or substituted with 1 , 2, 3, 4 or 5 identical or different substituents R10.
17 The compound of any of the preceding claims, wherein
X if present, is O.
18 An agricultural or veterinary composition for combating animal pests comprising at least one compound as defined in any of claims 1 to 17 and at least one inert liquid and/or solid acceptable carrier and optionally, if desired, at least one surfactant. 19 The use of a compound as defined in any of claims 1 to 17 for combating or controlling invertebrate pests, for protecting growing plants from attack or infestation by invertebrate pests, for protecting plant propagation material, especially seeds, from soil insects, or for protect the seedlings roots and shoots of plants from soil and foliar insects.
20 The compound as defined in any of claims 1 to 17 for the use in the treatment animals infested or infected by parasites, for preventing animals of getting infected or infested by parasites or for protecting animals against infestation or infection by parasites.
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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10206397B2 (en) 2013-09-19 2019-02-19 Basf Se N-acylimino heterocyclic compounds
US10220027B2 (en) 2011-07-13 2019-03-05 Gilead Sciences, Inc. FXR (NR1H4) binding and activity modulating compounds
US10329286B2 (en) 2016-06-13 2019-06-25 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10421730B2 (en) 2016-06-13 2019-09-24 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
CN111808018A (en) * 2020-08-14 2020-10-23 青岛恒宁生物科技有限公司 Production process of acetamiprid
US11225473B2 (en) 2019-01-15 2022-01-18 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds
US11524005B2 (en) 2019-02-19 2022-12-13 Gilead Sciences, Inc. Solid forms of FXR agonists
US11833150B2 (en) 2017-03-28 2023-12-05 Gilead Sciences, Inc. Methods of treating liver disease
US11938134B2 (en) 2017-03-10 2024-03-26 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US12528767B2 (en) 2019-07-30 2026-01-20 Eikonizo Therapeutics, Inc. HDAC6 inhibitors and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097604A1 (en) * 2002-05-16 2003-11-27 Bayer Cropscience Gmbh Pyridine carboxamide derivatives and their use as pesticides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003097604A1 (en) * 2002-05-16 2003-11-27 Bayer Cropscience Gmbh Pyridine carboxamide derivatives and their use as pesticides

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
LI X. ET AL.: "The synthesis and biological activities of 1,2,4-triazole-5-thiones bearing 2-chloropyrid-5-methyl", HUAXUE TONGBAO, vol. 65, no. 2, 1 January 2002 (2002-01-01), pages W013/1 - W013/4, XP009185440 *
LI X. Z. ET AL.: "Synthesis and biological activities of 3-(2-furyl)-4-aryl-1,2,4-triazole-5-thiones", CHINESE CHEMICAL LETTERS, vol. 13, no. 2, 1 January 2002 (2002-01-01), pages 129 - 132, XP009185441 *
YE D.J. ET AL.: "Synthesis and fungicidal activities of thiourea derivatives containing pyridine moiety", HUAXUE SHIJI, vol. 32, no. 5, 1 January 2010 (2010-01-01), pages 411 - 412, 454, XP009185439 *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10220027B2 (en) 2011-07-13 2019-03-05 Gilead Sciences, Inc. FXR (NR1H4) binding and activity modulating compounds
US10485795B2 (en) 2011-07-13 2019-11-26 Gilead Sciences, Inc. FXR (NR1H4) binding and activity modulating compounds
US10757938B2 (en) 2013-09-19 2020-09-01 Basf Se N-acylimino Heterocyclic Compounds
US10206397B2 (en) 2013-09-19 2019-02-19 Basf Se N-acylimino heterocyclic compounds
US10440953B2 (en) 2015-08-07 2019-10-15 Basf Se Control of pests in maize by ginkgolides and bilobalide
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US10981881B2 (en) 2016-06-13 2021-04-20 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10774054B2 (en) 2016-06-13 2020-09-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11247986B2 (en) 2016-06-13 2022-02-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10421730B2 (en) 2016-06-13 2019-09-24 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US12358903B2 (en) 2016-06-13 2025-07-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10329286B2 (en) 2016-06-13 2019-06-25 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US12370194B2 (en) 2017-03-10 2025-07-29 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US11938134B2 (en) 2017-03-10 2024-03-26 Eikonizo Therapeutics, Inc. Metalloenzyme inhibitor compounds
US11833150B2 (en) 2017-03-28 2023-12-05 Gilead Sciences, Inc. Methods of treating liver disease
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