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WO2015162244A1 - Composés n-acylamidine - Google Patents

Composés n-acylamidine Download PDF

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Publication number
WO2015162244A1
WO2015162244A1 PCT/EP2015/058886 EP2015058886W WO2015162244A1 WO 2015162244 A1 WO2015162244 A1 WO 2015162244A1 EP 2015058886 W EP2015058886 W EP 2015058886W WO 2015162244 A1 WO2015162244 A1 WO 2015162244A1
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alkyl
radicals
alkoxy
unsubstituted
group
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Birgit GOCKEL
Martin John MCLAUGHLIN
Karsten KÖRBER
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
    • A01N43/34—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

Definitions

  • the present invention relates to N-acylamidine compounds 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-acylamidine compounds 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 N-acylamidine compounds.
  • 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
  • F3 ⁇ 4 is, inter alia, hydrogen, alkyl, carbamoyl, F3 ⁇ 4 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, R2 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.
  • N-acylamidine compounds of the general formula (I) described below by their stereoisomers, their tautomers and their salts. Therefore, the present invention relates to N-acylamidine compounds of formula (I)
  • X is O or S, in particular O;
  • 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 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 R 6 , 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 R 7 ,
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-,
  • C3-C6-cycloalkyl which is unsubstituted or may carry any combination of 1 , 2, 3, 4 or 5 radicals R 10 ,
  • Cyc 1 -Q 1 where 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 radicals R 4a , R 4b , R 4c and R 4d , where
  • R 4a is selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C10- 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 5a ,
  • Cyc 3 is phenyl or 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 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 a single bond, Ci-C4-alkanediyl or C2-C4-alkenediyl;
  • R 4b is 0-R 5b ;
  • R 4c is S-R 5c ;
  • 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 5a 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 5a 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 ;
  • R 5c independently of each other are selected from the group consisting of Ci-Cio-alkyl, C 2 -Cio-alkenyl, C 2 -Cio-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 5a ,
  • 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 5d , R 5e independently of each other are selected from the group consisting of hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-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 5a , C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • R 5d and R 5e 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 four aforementioned radicals are unsubstituted or may carry 1 , 2, 3 or 4 radicals R 7c , provided that at least one of the radicals R 5d and R 5e is different from hydrogen; where, independently of their occurrence, n is 0, 1 or 2;
  • R 6 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 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-C6- cyclo
  • 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, 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- halocyclo
  • phenyl and benzyl wherein the phenyl ring of the two last-mentioned radicals 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,
  • 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, 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
  • 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-cycloalkyl, Cs-Cs-halocycloalkyl, C3- C8-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-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C2-C6-haloalkyn
  • 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- C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl
  • R 10a 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 three aforementioned aliphatic 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, Cs-Ce-cycloalkyl, Ci-Ce- haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl
  • 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-
  • C6-alkyl)amino di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyl- oxy and (Ci-C6-alkoxy)carbonyl,
  • R 12 independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, C 2 -C 6 - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C 4 -alkyl, C3-C8-halocycloalkyl-Ci-C 4 - alkyl, Ci-C6-haloalkoxy-Ci-C 4 -alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or carry 1 , 2, 3 or 4 substitu
  • R 13 , R 14 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; R 15 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, SF 5 , OH, Ci-C6-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, (C1-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl;
  • 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-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 R 7 , and
  • Cyc 4 is phenyl or 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 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
  • R 16a independently of its occurrence, is selected from the group consisting of
  • phenyl, benzyl, pyridyl and pyridylmethyl wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF 5 , OH, Ci-Ce-alkyl, C 3 -C 6 -cycloalkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 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 (
  • R 17b 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/7-butyldimethylsilyl,
  • 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;
  • 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 -Ce-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, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci
  • the present invention relates to N-acylamidine compounds of formula (I):
  • X is O or S, in particular O, 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 R 6 , 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 R 7 ,
  • 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
  • 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; is selected from the group consisting of hydrogen, CN, Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or carries any
  • 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; is selected from radicals R 4a , R 4b , R 4c and R 4d , where
  • R 4a is selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-C10- 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 5a ,
  • Cyc 3 is phenyl or 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 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 ,
  • 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 5a 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 5a 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 ;
  • R 5b , R 5c independently of each other are selected from the group consisting of Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-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 5a ,
  • R 5d , R 5e independently of each other are selected from the group consisting of hydrogen, Ci-Cio-alkyl, C2-Cio-alkenyl, C2-Cio-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 5a , C3-Cio-Cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • R 5d and R 5e 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 7c ,
  • radicals R 5d and R 5e are different from hydrogen; where, independently of their occurrence, n is 0, 1 or 2; R 6 is selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF 5 , Ci-
  • 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
  • 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,
  • 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 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
  • 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 ; 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 - C8-cycloalkyl-Ci-C4-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 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 aromaticring 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 haloal
  • heterocyclic ring 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,
  • 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,
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 identical or different radicals selected from halogen, OH , CN , N0 2 , SCN , SF 5 , OH , Ci-C 6 -alkyl, C 3 -C 6 -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
  • 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 , SF 5 , OH , d-Ce-alkyl, C 3 -C 6 -cycloalkyl, Ci-Ce-haloalkyI, Ci-Ce-alkoxy, Ci-C 6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(C
  • R 12 independently of their occurrence, are selected from the group consisting of d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkoxy-Ci-C 4 -alkyl, C 2 -C 6 - alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C3-C8-cycloalkyl-Ci-C 4 -alkyl, C3-Cs-halocycloalkyl-Ci-C 4 - alkyl, Ci-C6-haloalkoxy-Ci-C 4 -alkyl, phenyl and benzyl, where the phenyl ring in last two radicals are unsubstituted or carry 1 , 2, 3 or 4 substitu
  • R 14 independently of their occurrence, are selected from the group consisting of hydrogen, halogen, CN, Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C 4 -alkoxy-Ci-C 4 - 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-C 4 - 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-C 4 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-C6- alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbony
  • Cyc 4 is phenyl or 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 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;
  • R 16a independently of its occurrence, is selected from the group consisting of
  • 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-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)- carbonyloxy and (Ci-C6-alkoxy)carbonyl,
  • phenyl, benzyl, pyridyl and pyridylmethyl wherein the last four radicals may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, SCN, SF 5 , OH, d-Ce-alkyl, C 3 -C 6 -cycloalkyl, d-Ce-haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-halo- alkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C6-alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci- C6-alkyl)carbonyloxy and (
  • R 17 independently of its occurrence, is selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
  • 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, 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, partially or fully halogenated and/or oxygenated and/or may carry 1 or 2 radicals selected from Ci-C4-alkoxy, phenyl, benzyl, pyridyl and phenoxy, wherein
  • 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;
  • 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, partially or fully halogenated and/or to carry 1 , 2 or 3 substituents selected from Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalk
  • R 18a , R 18b are each independently from one another selected from the group consisting of hydrogen, Ci-C6-alkyl, Cs-Cs-cycloalkyl, 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 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,
  • 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 aromaticring 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 haloal
  • the present invention relates to and includes the following embodiments:
  • 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;
  • 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 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.
  • 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
  • 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 (NH 4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C 4 -hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Ci- C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
  • 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 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, 3,3-dimethylbutylthio, 1 -ethylbutylthio,
  • Ci-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 Ci-Cs-alkylthio and also includes, for example, nonylthio, decylthio and positional isomers thereof.
  • 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.
  • 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, cydobutyl, 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 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 - fluorocycloprpyl, 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, cyclobutyl methyl, 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-dihydrofur-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-isox
  • Examples of 5- or 6-membered aromatic heterocyclic rings also termed heteroaromatic rings 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 X, Het, R 1 ,R 2 , R 3a , R 3b , R 4 , including the variables R 4a , R 4b , R 4c and R 4d , 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 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:
  • 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-C4-haloalkyl, even more preferably from fluorine, chlorine, Ci-C2-alkyl, such as methyl or ethyl
  • 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, 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 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
  • 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, 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-trifluor
  • 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 or halogen, in particular 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, 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 difluoro
  • 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 or 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.
  • variable Cyc 1 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridiyl, 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-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 N0 2 , CN and Ci-C 4 -alkoxy.
  • halogen such as fluorine, chlorine or bromine
  • 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, 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.
  • 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-C 4 -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, Ci-C4-alkylcarbonyl,
  • Ci-C4-haloalkylcarbonyl Ci-C4-alkoxycarbonyl
  • 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 R 10 , phenylcarbonyl, phenoxycarbonyl, wherein the last two 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, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalky
  • 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
  • R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is
  • radical R 10 is 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
  • NO2 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.
  • 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 .
  • the variable R 7 is in particular selected 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, 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 N0 2 , CN, cyclopropyl and Ci-C 4 -alkoxy.
  • 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.
  • variable Cyc 2 is in particular selected from the group consisting of phenyl and 5- or 6-membered hetaryl, such as pyridiyl, 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-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 N0 2 , CN and Ci-C 4 -alkoxy.
  • halogen such as fluorine, chlorine or bromine
  • 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-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.
  • 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 haloalkyl 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
  • variable R 4 is a radical R 4a as defined above.
  • variable R 4a is in particular selected from the group consisting of
  • 6-membered heteroaryl having 1 , 2 or 3 nitrogen atoms as ring members and where heteroaryl is unsubstituted or may be substituted with 1 , 2, 3 or 4 identical or different substituents R 10 ;
  • variable R 5a is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:
  • variable R 5a is especially selected from the group consisting of CN, N0 2 , Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, S(0) n R 8a and S(0) n NR 17a R 17 .
  • variable R 10 is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:
  • halogen CN, OH, SH, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C1-C4- alkylcarbonyl, Ci-C 4 -haloalkylcarbonyl, Ci-C 4 -alkoxycarbonyl, NH2-C(0), Ci-C 4 -alkylthio, C1-C4- alkylsulfonyl, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfonyl, SO2NH2, Ci-C4-alkylaminocarbony and di-(Ci-C4-alkyl)aminocarbonyl.
  • variable R 10a is as defined above and, irrespectively of its occurrence, has in particular one of the following meanings:
  • variable R 4 is different from trifluoromethyl.
  • variable R 4 is different from Ci-C6-alkyl and Ci-C6-haloalkyl.
  • variable R 4 is different from Ci-C6-alkyl, Ci-C6-haloalkyl and phenyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 .
  • R 7a 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 R 10 , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci- C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amin
  • R 8 is selected from the group consisting of Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkoxycarbonyl,
  • 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 R 10 , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, 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)amino,
  • phenylaminocarbonyl wherein the last mentioned radical may be unsubstituted or carry 1 , 2, 3 or 4 substituents selected from halogen, OH, CN, NO2, 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;
  • 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 , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-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-
  • R 9a is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is
  • R 10 unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-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;
  • R 9b is selected from the group consisting of hydrogen, Ci-C4-alkyl and phenyl, which is
  • R 10 unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are identical or different and in particular selected from the group consisting of halogen, OH, CN, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 -haloalkylthio, Ci-C 6 - 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;
  • R 10 is selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci- C 4 -alkoxycarbonyl, NH 2 -C(0), Ci-C 4 -alkylthio, Ci-C 4 -alkylsulfonyl, Ci-C 4 -haloalkylthio, Ci-
  • R 10a is selected from the group consisting of halogen, CN, NO2, OH, SH, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci- C 4 -alkoxycarbonyl, NH 2 -C(0), S(0) n R 8a , SO2NH2, Ci-C 4 -alkylaminocarbonyl and di-(Ci-C 4 - alkyl)aminocarbonyl, or
  • 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, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, C1-C6 haloalkoxy, (Ci-C6-alkyl)carbonyl and
  • R 16 is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two
  • R 16a is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two
  • radicals are unsubstituted, partly or completely halogenated
  • benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 2 , Ci-Ce-alkyI, Ci-C 6 -haloalkyl, Ci-Ce-alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 -alkylthio, Ci C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy 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 unsbustituted or carries 1 , 2, 3 or 4 radicals selected from halogen, OH, CN, N0 2 , Ci-Ce-alkyI, Ci-C 6 -haloalkyl, Ci-Ce-alkoxy, Ci-C 6 haloalkoxy, (d- 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-C 4 -alkyl
  • R 9b is selected from the group consisting of hydrogen and Ci-C 4 -alkyl
  • R 10 is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci
  • Ci-C 4 -alkyl Ci-C 4 -haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio and Ci-
  • R 10a is selected from the group consisting of halogen, CN, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C4-alkylthio, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylthio and Ci- C4-haloalkylsulfonyl;
  • R 15 is selected from the group consisting of hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl;
  • R 16 is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, where the two
  • R 16a is selected from the group consisting of Ci-C6-alkyl and C2-C6-alkenyl, where the two aforementioned radicals are selected from halogen, OH, CN, N0 2 , d-Ce-alkyl, d-Ce-haloalkyl, Ci-Ce-alkoxy, d-C 6 haloalkoxy, Ci-C 6 -alkylthio, C C6-haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)amino, di-(Ci-C alkyl)amino, (Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)carbonyloxy and (Ci-C6-alkoxy)carbonyl; R 16a is selected from the group consisting of Ci-C6-alkyl and C2-C
  • variable R 4 is Ci-C6-alkyl, which is unsubstituted, partly or completely halogenated and/or may carry any combination of 1 , 2 or 3 radicals R 5a , where R 5a is as defined above and in particular selected from the group consisting of CN, N0 2 , Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and S(0) n NR 17a R 17b .
  • variable R 4 is in particular Ci-C6-alkyl, which carries any combination of 1 , 2 or 3 radicals R 5a , where R 5a is as defined above and in particular selected from the group consisting of CN, N0 2 , Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and S(0) n NR 17a R 17b and where Ci-C 6 - alkyl may further carry 1 , 2 or 3 halogen atoms.
  • radicals R 4 examples include the following radicals R-4.1 to R-4.12
  • variable R 4 is in particular Ci-C6-alkyl, which carries any combination of 1 , 2 or 3 radicals R 5a , where R 5a is as defined above and in particular selected from the group consisting of CN, NO2, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy and S(0) n NR 17a R 17b and where Ci-C6-alkyl may further carry 1 , 2 or 3 halogen atoms.
  • 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 unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , which are in particular selected from halogen, CN, NO2, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C1-C4- alkoxy and Ci-C 4 -haloalkoxy.
  • R 4 examples include 2-thiazolyl (R-40.1 ) and 2-pyrazinyl (R-40.2).
  • R-40.1 2-thiazolyl
  • R-40.2 2-pyrazinyl
  • A is CH 2 , CH 2 CH2 or CH2CH 2 CH2,
  • Rioaa j s hydrogen or a radical R 10a as defined above, wherein R 10aa is in particular selected from hydrogen, halogen, especially fluorine, S(0) n R 8a , CN and N0 2 , where n is 0, 1 or 2 and R 8a is as defined above an in particular selected from Ci-C4-alkyl and Ci-
  • 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-41.4 1 -fluorocyclobutyl
  • R-41.5 1 -cyanocyclopropyl
  • R-41.10 1 -(methylsulfinyl)cyclopropyl
  • R-41.1 1 1 -(methylsulfonyl)cyclopropyl
  • R-41.12 1 -(ethylthio)cyclopropyl
  • R-41.13 1 -(ethylsulfinyl)cyclopropyl
  • R-41.14 1 -(ethylsulfonyl)cyclopropyl
  • R-41.16 1-(methylsulfinyl)cyclobutyl
  • R-41.17 1 -(methylsulfonyl)cyclobutyl
  • R-41.18 1 -(ethylthio)cyclobutyl
  • R-41.19 1 -(ethylsulfinyl)cyclobutyl
  • R-41.20 1 -(ethylsulfonyl)cyclobutyl
  • R-42.5 2-cyano-2-oxiranyl
  • variable R 4 is a radicalmula R-43:
  • n 0, 1 or 2;
  • R 8a is as defined above and in particular Ci-C4-alkyl, such as methyl or ethyl, or Ci-C 4 - haloalkyl such as trifluoromethyl, 2,2,2-trifluoroethyl, 1 ,1 ,2,2-tetrafluoroethyl or
  • radicals R-43 are the radicals R-43.1 to R-43.2:
  • R-43.2 CF 2 -S(0)-CH 3 ,
  • R-43.3 CF 2 -S(0) 2 -CH 3 ,
  • R-43.4 CF 2 -S-C 2 H 5 ,
  • R-43.6 CF 2 -S(0) 2 -C 2 H 5 .
  • variable R 4 is a radical of formula R-44:
  • R x is hydrogen, halogen, CN , N0 2 , Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, N R 17a R 17b or
  • R 16 is benzyl which is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from
  • halogen OH , CN , N0 2 , Ci-Ce-alkyI, d-Ce-haloalkyl, Ci-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.
  • R 16 is especially selected from the group consisting of Ci-C 4 -alkyl, C1-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 , d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkoxy, Ci-C 6 haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, (Ci-C6-alkyl)a
  • radicals R-44 are the radicals R-44.1 to R-44.40, where R x and R 16 are as defined in the rows of the following table A:
  • R 8 , R 8a , R 15 , R 17a , R 17b irrespectively of their occurrence, have especially one of the following meanings:
  • R 7a is selected from the group consisting of hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C3-
  • R 8 is selected from the group consisting of Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C1-C4- alkylcarbonyl, Ci-C 4 -haloalkylcarbonyl, Ci-C 4 -alkoxycarbonyl,
  • Ci-C 4 -alkylaminocarbonyl di-(Ci-C 4 -alkyl)aminocarbonyl, phenyl, benzyl, where the phenyl ring in the last five mentioned radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 , phenylcarbonyl, phenoxycarbonyl, wherein the last two 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, C 3 -C 6 -cycloalkyl, Ci-C 6 - haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci- C6-alkylsulfony
  • R 8a is selected from the group consisting of Ci-C 4 -alkyl, Ci-C 4 -haloalkyl and phenyl, which is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • R 10 is selected from the group consisting of halogen, CN, OH, SH, Ci-C4-alkoxy, C1-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
  • 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, NO2, d-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, Ci-Ce haloalkoxy, (Ci-C6-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 unsbustituted 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.
  • variable R 4 is a radical 0-R 5b or S-R 5c , where R 5b and R 5c are as defined above.
  • the variables R 5b and R 5c independently of each other, are in particular selected from the group consisting of C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-Ci-C4-alkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated, and C3-C6- cycloalkyl, which is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 , where R 10 is as defined above and in particular selected from the group consisting of halogen, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkyl and Ci-C
  • the variables R 5b and R 5c are especially selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloa I kyl-C-i -C 4 -a I kyl .
  • variable R 4 is a radical NR 5d R 5e , where R 5d and R 5e are as defined above.
  • the variables R 5d and R 5e independently of each other, have in particular the following meanings.
  • R 5d is selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-
  • C3-C6-cycloalkyl which is unsubstituted or may be substituted with 1 , 2, 3, 4 or
  • R 5e is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, C3-C6-cycloalkyl-Ci-C 4 -alkyl, wherein each of the three aforementioned radicals are unsubstituted, partly or completely halogenated,
  • C3-C6-cycloalkyl which is unsubstituted or may be substituted with 1 , 2, 3, 4 or
  • R 5d and R 5e may also form a bivalent radical, selected from the group
  • variables R 5d and R 5e independently of each other, have in especially the following meanings.
  • R 5d is selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl and C3-C6-cycloa I kyl-Ci -C 4 -a I kyl ;
  • R 5e is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C3-
  • R 5d and R 5e may also form a bivalent radical, selected from the group
  • R 7a , R 7c and R 10 are as defined above and irrespectively of their occurrence, have especially one of the following meanings:
  • R 7c is selected from the group consisting of hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C3-C6- cycloalkyl, C3-C6-cycloalkyl-Ci-C 4 -alkyl, phenyl and benzyl, where the phenyl ring in the last two radicals is unsubstituted or carries 1 , 2, 3 or 4 radicals R 10 ;
  • R 10 is selected from the group consisting of halogen, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci- C 4 -alkyl and Ci-C 4 -haloalkyl.
  • variable X is preferably O.
  • 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 ,
  • 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 .
  • Particularly preferred are also compounds of the formula (I), in particular the compounds of groups (1 ), (1 a), (1 b), (1 c), (1 d), (1 e), (2) and (3) 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
  • 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-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.
  • 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; 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 15 , R 16a , R 17 , R 17a , R 17b , R 17c irrespectively of their occurrence, in particular have the following meanings, if not stated otherwise:
  • 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-difluoroethyl
  • 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 2,
  • 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 -piperazinyl, 4-methyl-1 -piperazinyl 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- 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.
  • 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 -piperazinyl, 4-methyl-1 -piperazinyl 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-difluoroethy
  • 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- haloalkyi, 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
  • 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 R 4a , in particular a radical R 4 as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d) or (1 e).
  • 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-C 4 -alkyl.
  • R 4 is a radical R 4a , in particular a radical R 4 as defined for the groups of embodiments (1 a), (1 b), (1 c), (1 d) or (1 e).
  • R 1 , R 3a , R 3b and R 4 are as defined below: is hydrogen or methyl and especially hydrogen;
  • 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, CH2CN, CH2CH2CN, CH2NO2 and CH2CH2NO2; 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.
  • 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 and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds I-A.1 a.1 to I-A.1 a.880).
  • 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 and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.2a.1 to l-A.2a.880).
  • 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 and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.3a.1 to l-A.3a.880).
  • 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 and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.4a.1 to l-A.4a.880).
  • a special group of embodiments relates to the compounds of formula (I-A.5), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.5a.1 to l-A.5a.880).
  • a further special group of embodiments relates to the compounds of formula (I-A.6), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.6a.1 to l-A.6a.880).
  • a further special group of embodiments relates to the compounds of formula (I-A.7), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.7a.1 to l-A.7a.880).
  • a further special group of embodiments relates to the compounds of formula (I-A.8), to their tautomers, to their stereoisomers and to their salts, where R 1 is hydrogen and where R 3a , R 3b and R 4 are as defined in lines 1 to 880 of the following table B (compounds l-A.8a.1 to l-A.8a.880).

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Abstract

La présente invention concerne des composés N-acylamidine de formule (I) telle que définie dans la description, y compris leurs stéréo-isomères, leurs tautomères et leurs sels, ainsi que des compositions comprenant de tels composés. La présente invention concerne également l'utilisation des composés N-acylamidine de formule (I), de leurs stéréoisomères, de leurs tautomères et de leurs sels, pour lutter contre des parasites invertébrés. Elle concerne encore des procédés de lutte contre les parasites invertébrés qui comprennent l'application de ces composés N-acylamidine.
PCT/EP2015/058886 2014-04-25 2015-04-24 Composés n-acylamidine Ceased WO2015162244A1 (fr)

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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
US11297837B2 (en) 2016-02-19 2022-04-12 Basf Se Pesticidally activi mixtures comprising anthranilamide compounds
US11247986B2 (en) 2016-06-13 2022-02-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11739065B2 (en) 2016-06-13 2023-08-29 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10981881B2 (en) 2016-06-13 2021-04-20 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US12358903B2 (en) 2016-06-13 2025-07-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10421730B2 (en) 2016-06-13 2019-09-24 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10329286B2 (en) 2016-06-13 2019-06-25 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US10774054B2 (en) 2016-06-13 2020-09-15 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11833150B2 (en) 2017-03-28 2023-12-05 Gilead Sciences, Inc. Methods of treating liver disease
US11225473B2 (en) 2019-01-15 2022-01-18 Gilead Sciences, Inc. FXR (NR1H4) modulating compounds
US11524005B2 (en) 2019-02-19 2022-12-13 Gilead Sciences, Inc. Solid forms of FXR agonists
US12102625B2 (en) 2019-02-19 2024-10-01 Gilead Sciences, Inc. Solid forms of FXR agonists
US11834441B2 (en) 2019-12-06 2023-12-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
US11919887B2 (en) 2019-12-06 2024-03-05 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
US12247021B2 (en) 2019-12-06 2025-03-11 Vertex Pharmaceuticals Incorporated Substituted tetrahydrofurans as modulators of sodium channels
US11827627B2 (en) 2021-06-04 2023-11-28 Vertex Pharmaceuticals Incorporated N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamides as modulators of sodium channels
US12258333B2 (en) 2021-06-04 2025-03-25 Vertex Pharmaceuticals Incorporated N-(hydroxyalkyl (hetero)aryl) tetrahydrofuran carboxamides as modulators of sodium channels

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