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WO2016198611A1 - Composés hétérocycliques n-(thio)acylimino - Google Patents

Composés hétérocycliques n-(thio)acylimino Download PDF

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Publication number
WO2016198611A1
WO2016198611A1 PCT/EP2016/063316 EP2016063316W WO2016198611A1 WO 2016198611 A1 WO2016198611 A1 WO 2016198611A1 EP 2016063316 W EP2016063316 W EP 2016063316W WO 2016198611 A1 WO2016198611 A1 WO 2016198611A1
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Prior art keywords
alkyl
het
group
alkoxy
spp
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Inventor
Karsten KÖRBER
Martin John MCLAUGHLIN
Birgit GOCKEL
Wolfgang Von Deyn
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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to N-(thio)acylimino heterocyclic compounds, including their stereoisomers, tautomers and salts, and to compositions comprising such compounds.
  • the invention also relates to the use of the N-(thio)acylimino heterocyclic compounds, 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 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.
  • EP 259738 discloses compounds of the formula A, which have insecticidal activity:
  • W is a substituted pyridyl radical or a 5-or 6-membered heterocyclic radical
  • R is hydrogen or alkyl
  • Y is inter alia a nitrogen atom
  • Z is an electron withdrawing group selected from nitro and cyano.
  • Pesticidal compounds which are similar to those of EP 259738, are known from
  • EP 639569 where the moiety Z is an electron withdrawing group such as alkoxcarbonyl, arylcarbonyl, heterocyclic carbonyl, Ci-C4-alkylsulfonyl, sulfamoyl or Ci-C4-acyl.
  • Ar is an aryl or 5- or 6-membered heterocyclic group
  • R a is hydrogen or alkyi
  • Y' is hydrogen, halogen, a hydroxyl group, an alkyi group or an alkoxy group
  • Rb is an alkyi group substituted with halogen or an alkoxy group, optionally substituted with halogen.
  • Pesticidal compounds which are similar to those of US 2013/0150414, are known from WO 2013/129688.
  • WO 2015/028630 describes compounds similar to the compounds of formula (B), where Ar is an optionally substituted 3-tetrahydrofuryl radical and Rb is a heterocyclic radical.
  • 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-substituted (thio)acyl-imino compounds of the general formula (I) described below by their stereoisomers, their tautomers and their salts. Therefore, the present invention relates to N-(thio)acylimino compounds of formula (I):
  • heteroaromatic ring comprising 1 , 2, 3 or 4 heteroatoms selected from sulfur, oxygen and nitrogen as ring members, wherein the heteroaromatic ring is optionally substituted by 1 , 2, 3 or 4 identical or different substituents R 6a ;
  • R 2 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, nitro, SCN, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6- alkynyl, wherein the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals may be partly or completely halogenated and/or may carry one or more radicals R 7 ;
  • a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 substituents R 10 , and wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 1 and R 2 form, together with the carbon atom they are attached to, a 3-, 4-, 5- or 6-membered saturated or partly unsaturated carbocyclic or heterocyclic ring containing 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein the cycle is unsubstituted or may carry 1 or 2 radicals R 10 ; or
  • R 3d may further be NR 9a R 9b ;
  • R 3b and R 3c may further be selected from OH, Ci-C6-alkoxy, C3-C6- cycloalkoxy, (C3-C6-cycloalkyl)-Ci-C4-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, (Ci-C6-alkoxy)-Ci-C6-alkoxy, where the aliphatic and cycloaliphatic moieties in the 6 last-mentioned radicals are unsubstituted or are partly or completely halogenated; and phenoxy which is unsubstituted or substituted by 1 , 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; or
  • R 3c together with the nitrogen atom to which they are bound, form an N-bound, mono- or bicyclic 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximally unsaturated heterocyclic radical which may comprise 1 , 2 or 3 further heteroatoms selected from N, O and S as ring members, where the heterocyclic radical is unsubstituted or substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and
  • R 5 independently of each other, are selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, SCN, SF 5 , Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- alkenyl, C2-Cio-alkynyl, wherein the 4 last-mentioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated and/or may carry one or more radicals R 7 ;
  • each R 6 is independently 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, wherein the 4 last-mentioned radicals may be partly or completely halogenated and/or may carry one or more
  • phenyl where the phenyl ring is optionally substituted with 1 , 2, 3, 4 or 5 identical or different substituents R 10 ,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 substituents R 10 , and wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • heterocyclic ring has 1 or 2 heteroatoms as ring members which are selected from the group consisting of O, S, and N, wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized and where said carbo- or heterocyclic ring is unsubstituted or carries 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl,
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 substituents R 10 , and wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized,
  • R 7 bound on the same or adjacent carbon atom(s), together with the carbon atom(s) they are bound to, may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 7 as a substituent on a cycloaliphatic radical is additionally selected from the group
  • each R 7a is independently selected from the group consisting of hydrogen, halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cyclo
  • phenyl phenyl-Ci-C-4-alkyl, where the phenyl ring in the two last-mentioned radicals is optionally substituted with 1 , 2, 3, 4 or 5 substituents R 10 , and
  • a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 substituents R 10 , and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized; and R 8 as a substituent on a sulfur atom is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy; R 9a , R 9b , independently of each other, are selected from the group consisting of hydrogen,
  • phenyl benzyl, 1-phenethyl, 2-phenethyl, where the phenyl ring in the four last-mentioned radicals is unsubstituted or substituted with 1 , 2, 3, 4 or 5 substituents R 10 , and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or maximally unsaturated C-bound heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, where the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 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 together with the nitrogen atom they are bound to, form a 3-, 4-, 5-, 6-, 7- or
  • heterocyclic ring 8-membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring, where the heterocyclic ring may contain one or two further heteroatoms selected from oxygen, sulfur and nitrogen as ring members, and wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, and where the heterocyclic ring may be substituted with 1 , 2, 3 or 4 radicals selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, phenyl
  • unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, where the heterocyclic ring is unsubstituted or may be substituted with 1 , 2, 3, 4 or 5 substituents independently selected from halogen, cyano, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may optionally be oxidized;
  • R 12 independently of their occurrence and independently of each other, are
  • Ci-C6-alkyl selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C4-alkyl, Ci-C6-haloalkoxy-Ci-C4- alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8-cycloalkyl-Ci-C4-alkyl, C3-C8- halocycloalkyl-Ci-C4-alkyl, phenyl and benzyl, where phenyl ring in last two radicals is unsubstituted or substituted with 1 , 2, 3, 4
  • R 13 , R 14 independently of each other, are selected from the group consisting of
  • phenyl, benzyl and pyridyl wherein the last three radicals may be unsubstituted or may carry 1 , 2, 3, 4 or 5 substituents independently selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, (Ci-C6-alkoxy)carbonyl,
  • each R 17 is independently selected from the group consisting of hydrogen, trimethylsilyl, triethylsilyl, fe/ibutyldimethylsilyl,
  • Ci-C6-alkyl C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4- alkyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Cs-Cs-cycloalkoxy, C3-C8- cycloalkyl-Ci-C4-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl wherein the 13 last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may carry 1 or 2 radicals independently selected from
  • R 17a , R 17b independently of each other, are selected from the group consisting of
  • R 17a and R 17b together with the nitrogen atom they are bound to, form a 3-, 4-, 5-, 6- or 7-membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may contain 1 or 2 further heteroatoms selected from oxygen, sulfur or nitrogen, and wherein the heterocyclic ring may be substituted with one or more substituents independently selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy, and wherein the nitrogen and/or the sulfur atom(s) of the heterocyclic ring may be oxidized;
  • phenyl optionally substituted with 1 , 2, 3, 4 or 5 substituents selected from CN, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and a 3-, 4-, 5-, 6- or 7- membered saturated, partly unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members, wherein the heterocyclic ring is optionally substituted with 1 , 2, 3 or 4 substituents selected from CN, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy; and wherein the nitrogen and the sulfur atom(s) of the heterocyclic ring may optionally be oxidized, or
  • R 19 bound on the same or adjacent carbon atom(s), together with the carbon atom(s) they are bound to, may form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partly unsaturated carbocyclic or heterocyclic ring comprising 1 , 2 or 3 heteroatoms selected from oxygen, nitrogen and sulfur as ring members; and where the carbocyclic or heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5 substituents selected from CN, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and C1-C6- haloalkoxy;
  • R 19 as a substituent on a cycloaliphatic radical is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl and C2-C6-haloalkynyl; and n is an integer selected independently from 0, 1 and 2; and the stereoisomers, tautomers and the agriculturally or veterinarily acceptable salts thereof.
  • the present invention relates to N-(thio)acylimino compounds of the general formula (I), to their agriculturally or veterinarily acceptable/useful salts, their enantiomers or diastereomers.
  • compositions comprising at least one compound of the formula (I) or a stereoisomer, tautomer or salt thereof;
  • a method for protecting growing plants from attack or infestation by invertebrate pests comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound of the formula (I) or a stereoisomer, a tautomer or salt thereof, in particular a method protecting crop plants from attack or infestation by animal pests, which comprises contacting the crop plants with a pesticidally effective amount of at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • a method for the protection of plant propagation material, especially seeds, from soil insects and of the seedlings' roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with at least one compound of the formula (I) or stereoisomer, a tautomer or salt thereof;
  • seeds comprising a compound of the formula (I) or an enantiomer, diastereomer or salt thereof;
  • a method for treating animals infested or infected by parasites or preventing animals of getting infected or infested by parasites or protecting animals against infestation or infection by parasites which comprises administering or applying to the animals a parasiticidally effective amount of a compound of formula (I) or the stereoisomers and/or salts, in particular veterinary acceptable salts, thereof;
  • a process for the preparation of a veterinary composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises formulating a compound of formula (I) or a stereoisomer, tautomer and/or veterinary acceptable salt thereof with a carrier composition suitable for veterinary use; the use of a compound of formula (I) or the stereoisomers, tautomers and/or veterinary acceptable salt thereof for the preparation of a medicament for treating, controlling, preventing or protecting animals against infestation or infection by parasites.
  • the present invention also relates to plant propagation materials, in particular as mentioned above to seeds, containing at least one compound of formula (I), a stereoisomer, a tautomer and/or an agriculturally acceptable salt thereof.
  • the 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.
  • the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound of the formula (I) or its mixtures.
  • 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 stereoisomers or tautomers, as well as amorphous or crystalline salts thereof.
  • Salts of the compounds of the formula (I) are preferably agriculturally salts as well as veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula (I) has a basic functionality or by reacting an acidic compound of formula (I) with a suitable base.
  • Suitable agriculturally or veterinary useful salts are especially the salts of those cations or anions, in particular the acid addition salts of those acids, whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NhV) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci- C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • invertebrate pest also termed “animal pest” as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant.
  • the plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • plants comprises any types of plants including “non-cultivated plants” and in particular "cultivated plants”.
  • non-cultivated plants refers to any wild type species or related species or related genera of a cultivated plant.
  • cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
  • organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
  • the prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.
  • Halogen will be taken to mean fluoro, chloro, bromo and iodo.
  • partially or fully 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 fully halogenated alkyl is also termed haloalkyl
  • partially or fully halogenated cycloalkyl is also termed halocycloalkyl
  • partially or fully halogenated alkylenyl is also termed haloalkenyl
  • partially or fully halogenated alkylynyl is also termed haloalkynyl
  • partially or fully halogenated alkoxy is also termed haloalkoxy
  • partially or fully halogenated alkylthio is also termed haloalkthio
  • partially or fully halogenated alkylsulfinyl is also termed haloalkylsulfinyl
  • partially or fully halogenated alkylsulfonyl is also termed haloalsulfonyl
  • partially or fully halogenated cycloalkylalkylalkyl is also termed halocycloalkylalkyl.
  • alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, dialkylamino and the like refers to saturated straight-chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 (“Ci-C 3 -alkyl”),1 to 4 (“Ci-C 4 -alkyl”), 1 to 6 (“Ci-C 6 -alkyl”), 1 to 8 (“Ci-C 8 -alkyl”) or 1 to 10 (“Ci- Cio-alkyl”) carbon atoms.
  • Ci-C2-Alkyl is methyl or ethyl.
  • Ci-C3-Alkyl is additionally propyl and isopropyl.
  • Ci-C 4 -Alkyl is additionally n-butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl
  • Ci-C6-Alkyl is additionally also, for example, pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,
  • Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2-ethylhexyl and positional isomers thereof.
  • haloalkyi as used herein, which is also expressed as “alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C 2 - haloalkyi”), 1 to 3 (“Ci-Cs-haloalkyI”), 1 to 4 (“Ci-C 4 -haloalkyl”), 1 to 6 (“Ci-Ce-haloalkyI”), 1 to 8 (“Ci-Ce-haloalkyl”) or 1 to 10 (“Ci-Cio-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl,
  • dichloromethyl trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,
  • Ci-C3-haloalkyl is additionally, for example, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1-difluoropropyl,
  • Ci-C 4 -haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
  • Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
  • alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 -C 3 -alkenyl"), 2 to 4 (“C 2 -C 4 -alkenyl"), 2 to 6 (“C 2 -C 6 - alkenyl”), 2 to 8 (“C 2 -C 8 -alkenyl”) or 2 to 10 (“C 2 -Cio-alkenyl”) carbon atoms and a double bond in any position, for example C 2 -C3-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl or
  • 2- methyl-2-propenyl 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1- pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl
  • haloalkenyl as used herein, which is also expressed as “alkenyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C 2 -C 3 -haloalkenyl"), 2 to 4 (“C 2 -C 4 -haloalkenyl"), 2 to 6 (“C 2 -C 6 - haloalkenyl”), 2 to 8 (“C 2 -C 6 -haloalkenyl”) or 2 to 10 (“C 2 -Cio-haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), 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 chlorovinyl, chloroallyl and the like.
  • alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C 3 -alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl”), 2 to 6 (“C 2 -C 6 -alkynyl”), 2 to 8 (“C 2 -C 8 - alkynyl”), or 2 to 10 (“C 2 -Cio-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C 2 -C3-alkynyl, such as ethynyl, 1-propynyl or 2-propynyl; C 2 -C 4 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C 2 -C6-alkynyl
  • haloalkynyl as used herein, which is also expressed as “alkynyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 ("C 2 -C 3 -haloalkynyl"), 2 to 4 ("C 2 -C 4 -haloalkynyl"), 3 to 4 ("C 3 -C 4 - haloalkynyl”), 2 to 6 (“C 2 -C 6 -haloalkynyl”), 2 to 8 (“C 2 -C 8 -haloalkynyl”) or 2 to 10 (“C2-C10- haloalkynyl”) carbon atoms and one or two triple bonds in any position (as mentioned above), 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;
  • cycloalkyl refers to mono- or bicyclic saturated hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl”), in particular 3 to 6 (“C3-C6-cycloalkyl”) or 3 to 5 (“C3-C5-cycloalkyl”) or 3 to 4 (“C3-C4-cycloalkyl”) carbon atoms.
  • Examples of monocyclic radicals having 3 to 4 carbon atoms comprise cyclopropyl and cyclobutyl.
  • monocyclic radicals having 3 to 5 carbon atoms comprise cyclopropyl, cyclobutyl and cyclopentyl.
  • Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Examples of monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.
  • the term cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
  • halocycloalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers to mono- or bicyclic saturated hydrocarbon groups having 3 to 8 (“Cs-Cs-halocycloalkyl” ) or preferably 3 to 6 (“C 3 -C 6 -halocycloalkyl") or 3 to 5 (“C3-C5- halocycloalkyl”) or 3 to 4 (“C3-C4-halocycloalkyl”) carbon ring members (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.
  • cycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group ("C3-Cs-cycloalkyl-Ci- C4-alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl”), more preferably a C3-C4-cycloalkyl group (“C3-C4-cycloalkyl-Ci-C4-alkyl”) as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Examples for C3-C4-cycloalkyl-Ci-C4-alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl and cyclobutylpropyl
  • Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4- alkyl, are cyclopentylmethyl, cyclopentylethyl, cyclopentyl propyl, cyclohexylmethyl,
  • C3-C8-cycloalkyl-Ci-C4-alkyl apart those mentioned for C3-C6-cycloalkyl-Ci-C4-alkyl, are cycloheptyl methyl, cycloheptylethyl,
  • C3-C6-cycloalkyl-methyl refers to a C3-C6-cycloalkyl group which is bound to the remainder of the molecule via a methylene group (CH2). Examples are cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl.
  • C3-C8-halocycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • C3-C6-halocycloalkyl-Ci-C4-alkyl refers to a C3-C6-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-alkoxy is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
  • Ci-C2-Alkoxy is methoxy or ethoxy.
  • Ci-C3-Alkoxy is additionally, for example, n-propoxy and 1-methylethoxy (isopropoxy).
  • Ci-C4-Alkoxy is additionally, for example, butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1-dimethylethoxy (tert-butoxy).
  • Ci-C6-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy,
  • Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.
  • Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
  • Ci-C2-haloalkoxy is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C3-haloalkoxy is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C4-haloalkoxy is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-C6-haloalkoxy is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom.
  • Ci-Cio-haloalkoxy is a
  • Ci-Cio-haloalkyl group as defined above, attached via an oxygen atom.
  • Ci-C2-Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHC , OCCI 3 , chlorofluoromethoxy,
  • dichlorofluoromethoxy chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy,
  • Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
  • C1-C4- Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • Ci-C6-Haloalkoxy is additionally, for example, 5-fluoropentoxy,
  • Ci-C4-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
  • 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,
  • Ci-C4-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
  • Ci-C6-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methoxymethyl, ethoxymethyl, propoxymethyl,
  • Ci-C6-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-C6-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.
  • 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.
  • C2-C6-alkenyloxy is a C2-C6-alkenyl group, as defined above, attached via an oxygen atom. Examples are ethenyloxy, propen-1-yloxy, allyloxy (propen-2-yl-oxy), buten-1-oxy, buten-2-oxy, buten-3-oxy, and the like.
  • C2-C6-haloalkenyloxy is a C2-C6-haloalkenyl group, as defined above, attached via an oxygen atom.
  • C2-C6-alkynyloxy is a C2-C6-alkynyl group, as defined above, attached via an oxygen atom. Examples are ethynyloxy, propyn-1-yloxy, propargyloxy (propyn-2-yl-oxy), butyn-
  • C2-C6-haloalkynyloxy is a C2-C6-haloalkynyl group, as defined above, attached via an oxygen atom.
  • C3-C6-cycloalkoxy denotes a C3-C6-cycloalkyl group, as defined above, which is attached via an oxygen atom.
  • Cs-Cs-cycloalkoxy denotes a Cs-Cs-cycloalkyI group, as defined above, which is attached via an oxygen atom.
  • Examples of C3-C6-cycloalkoxy comprise cyclopropoxy, cyclobutoxy, cyclopentoxy and cyclohexoxy.
  • Examples of C3-C8- cycloalkoxy comprise, in addition to those mentioned for C3-C6-cycloalkoxy, cycloheptoxy and cyclooctyloxy.
  • C3-C6-halocycloalkoxy denotes a C3-C6-halocycloalkyl group, as defined above, which is attached via an oxygen atom.
  • Cs-Cs-halocycloalkoxy denotes a C3-C8-halocycloalkyl group, as defined above, which is attached via an oxygen atom.
  • C3-C8-Cycloalkyl-Ci-C4-alkoxy is Ci-C4-alkoxy, as defined above wherein one of the hydrogen atoms is replaced by a Cs-Cs-cycloalkyI group.
  • C3-C8-Halocycloalkyl-Ci-C4-alkoxy is Ci-C4-alkoxy, as defined above wherein one of the hydrogen atoms is replaced by a C3-Cs-cycloalkyl group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the cycloalkyi moiety or in the alkoxy moiety or in both) are replaced by halogen atoms.
  • Ci-C2-alkylthio is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-alkylthio is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-alkylthio is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-alkylthio is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-Cio-alkylthio is a Ci-Cio-alkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Alkylthio is methylthio or ethylthio.
  • Ci-C3-Alkylthio is additionally, for example, n-propylthio or 1-methylethylthio (isopropylthio).
  • Ci-C4-Alkylthio is additionally, for example, butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or
  • Ci-C6-Alkylthio is additionally, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1 ,1-dimethylpropylthio,
  • d-Cs- Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
  • Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
  • Ci-C2-haloalkylthio is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C3-haloalkylthio is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C4-haloalkylthio is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C6-haloalkylthio is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-Cio-haloalkylthio is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom.
  • Ci-C2-Haloalkylthio is, for example, SCH2F, SCHF2, SCF3, SCH2CI, SCHC , SCCIs, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethyl
  • Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.
  • Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio,
  • C 1 -C2-a I ky Is u If i nyl is a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-alkylsulfinyl is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C 1 -C6-a I ky Is u If i nyl" is a Ci-C6-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-Ci o-a I kylsu If i nyl is a C1-C10- alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
  • Ci-C4-Alkylsulfinyl is additionally, for example, n-propylsulfinyl,
  • C1-C6- Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl,
  • d-Cs-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2-ethylhexylsulfinyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
  • Ci-C2-haloalkylsulfinyl is a Ci-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C4-haloalkylsulfinyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C6-haloalkylsulfinyl is a C1-C6- haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • C1-C10- haloalkylsulfinyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
  • Ci-C 2 -Haloalkylsulfinyl is, for example, S(0)CH 2 F, S(0)CHF 2 , S(0)CF 3 , S(0)CH 2 CI, S(0)CHCI 2 , S(0)CCl3, chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl,
  • chlorodifluoromethylsulfinyl 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2- fluoroethylsulfinyl, 2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl,
  • Ci-C4-Haloalkylsulfinyl is additionally, for example,
  • Ci-C6-Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.
  • Ci-C 2 -alkylsulfonyl is a Ci-C 2 -alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C3-alkylsulfonyl is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C4-alkylsulfonyl is a Ci-C4-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C6-alkylsulfonyl is a C1-C6- alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • C1-C10- alkylsulfonyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
  • Ci-C 2 -Alkylsulfonyl is methylsulfonyl or ethylsulfonyl.
  • Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1-methylethylsulfonyl (isopropylsulfonyl).
  • Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl),
  • C1-C6- Alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl,
  • Ci-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.
  • Ci-Cio-Alkylsulfonyl is additionally, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.
  • Ci-C2-haloalkylsulfonyl is a Ci-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C3-haloalkylsulfonyl is a Ci-C3-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C4-haloalkylsulfonyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • C1-C6- haloalkylsulfonyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-Cio-haloalkylsulfonyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
  • Ci-C2-Haloalkylsulfonyl is, for example, S(0)2CH2F,
  • C1-C3- Haloalkylsulfonyl is additionally, for example, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2-chloropropylsulfonyl,
  • Ci-C4-Haloalkylsulfonyl is additionally, for example,
  • Ci-C6-Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl,
  • 6- fluorohexylsulfonyl 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl.
  • alkylcarbonyl is a Ci-C6-alkyl ("Ci-C6-alkylcarbonyl”), preferably a Ci-C4-alkyl
  • Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl,
  • haloalkylcarbonyl is a Ci-C6-haloalkyl ("Ci-C6-haloalkylcarbonyl”), preferably a
  • Ci-C4-haloalkyl (“Ci-C4-haloalkylcarbonyl”) group, as defined above, attached via a carbonyl
  • Ci-C6-haloalkoxycarbonyl a Ci-C6-haloalkoxycarbonyl
  • Ci-C4-haloalkoxycarbonyl Ci-C4-haloalkoxycarbonyl
  • Ci-C6-alkylamino is a group -N(H)Ci-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
  • di-(Ci-C6-alkyl)amino is a group -N(Ci-C6-alkyl)2. Examples are dimethylamino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropylamino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.
  • aminocarbonyl is a group -C(0)-NH2.
  • Ci-C6-alkylaminocarbonyl is a group -C(0)-N(H)Ci-C6-alkyl. Examples are methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylaminocarbonyl, butylaminocarbonyl and the like.
  • di-(Ci-C6-alkyl)-aminocarbonyl is a group -C(0)-N(Ci-C6-alkyl)2. Examples are dimethylaminocarbonyl, diethylaminocarbonyl, ethylmethylaminocarbonyl,
  • Ci-C6-alkylaminosulfonyl is a Ci-C6-alkylamino group as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group (S(0)2).
  • di-(Ci-C6-alkyl)-aminosulfonyl is a di-(Ci-C6-alkyl)-amino group as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group.
  • Ci-C6-alkoxysulfonyl is a Ci-C6-alkoxy group as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group.
  • phenylsulfonyl is a phenyl group as mentioned above, which is bound to the remainder of the molecule by a sulfonyl group.
  • phenylcarbonyl is a phenyl group, which is bound to the reminder molecule by a carbonyl group.
  • phenoxycarbonyl is a phenoxy group, which is bound to the reminder molecule by a carbonyl group.
  • phenylaminosulfonyl is a group -S(0)2-NH-R, where R is phenyl.
  • (Ci-C6-alkoxy)-Ci-C6-alkoxy is a Ci-C6-alkoxy group, in particular Ci-C4-alkoxy as defined above, such as methoxy or ethoxy, wherein 1 hydrogen atom is replaced by C1-C6- alkoxy as defined above, examples including methoxymethoxy, ethoxymethoxy,
  • n-propoxymethoxy butoxymethoxy, 2-methoxyethoxy, 2-ethoxyethoxy, 2-(n-propoxy)ethoxy and 2-butoxyethoxy.
  • (C3-C6-cycloalkyl)-Ci-C6-alkoxy is Ci-C6-alkoxy, in particular Ci-C4-alkoxy as defined above, such as methoxy or ethoxy, wherein 1 hydrogen atom is replaced by C3-C6- cyclolalkyl as defined above, examples including cyclopropylmethoxy (OCH 2 -cyclopropyl), cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1 -cyclopropylethoxy (0-CH(CH 3 )- cyclopropyl), 1-cyclobutylethoxy, 1-cyclopentylethoxy, 1-cyclohexylethoxy, 2-cyclopropylethoxy (OCH2CH2)-cyclopropyl), 2-cyclobutylethoxy, 2-cyclopentylethoxy and 2-cyclohexylethoxy.
  • Phenyl-Ci-C4-alkyl is a Ci-C4-alkyl group, as defined above, wherein one of the hydrogen atoms is replaced by a phenyl ring. Examples are benzyl, phenyl-1 -ethyl and phenethyl (phenyl- 2-ethyl).
  • Ci-Cio-Alkylene is a linear or branched divalent alkyl radical having 1 to 10 carbon atoms.
  • Examples are -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 )-, -CH 2 CH 2 CH 2 -,
  • (C 2 -C4-alkenyl)-Ci-C4-alkyl refers to a C 2 -C4-alkenyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • (C 2 -C4-alkynyl)-Ci-C4-alkyl refers to a C 2 -C4-alkynyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
  • the term "3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic rings containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 , as ring members” denotes a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 , as ring members.
  • Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s).
  • Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Partly unsaturated rings contain less conjugated C-C and/or C-N and/or N-N double bonds than maximally allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic. 7-membered rings cannot be aromatic; they are homoaromatic (3 double bonds).
  • the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
  • Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include: Oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin- 2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl,
  • Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-
  • Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2-thienyl,
  • homoaromatic radicals such as 1 H-azepine, 1 H-[1 ,3]-diazepine and 1 H-[1 ,4]- diazepine.
  • examples for 5- or 6-membered heteroaromatic rings containing 1 , 2 ,3 or 4 heteroatoms selected from O, S and N include 1 ,2,3,4-1 H-tetrazol-1-yl, 1 ,2,3,4-1 H-tetrazol-5-yl, 1 ,2,3,4-2H-tetrazol-2-yl, 1 ,2,3,4-21-1- tetrazol-5-yl, 1 ,2,3,4-tetrazin-5-yl, 1 ,2,4,5-tetrazin-3-yl and 1 ,2,3,5-tetrazin-4-yl.
  • One embodiment of the present invention are compounds of formula (I), wherein X is selected from O.
  • Another embodiment of the present invention are compounds of formula (I), wherein X is selected from S.
  • Preferred are compounds of formula (I), wherein Het is selected from the group consisting of radicals of formulae Het-1 to Het-7, 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-2, Het-4 and Het-7:
  • Het-7 wherein # denotes the attachment point to the remainder of the molecule and R 6a is as defined above.
  • j is 0, 1 or 2, especially 0 or 1.
  • k is especially 1.
  • R 6a is in particular selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as
  • R 6a is more particularly selected from halogen and Ci-C2-haloalkyl, and especially from chlorine, bromine and trifluoromethyl (CF3). Very especially, R 6a is chlorine.
  • Het is selected from the group consisting of radicals of formulae Het-1 , Het-2, Het-4 and Het-7a:
  • R 6a is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy. Irrespectively of its occurrence, R 6a is more particularly selected from halogen and Ci-C2-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy,
  • Het is selected from the group consisting of radicals of formulae Het-1 a, Het-4a and Het-7b:
  • R 6a is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy. Irrespectively of its occurrence, R 6a is more particularly selected from halogen and Ci-C2-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy,
  • 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 j is 0, 1 or 2, in particular 1 or 2 and especially 1 , and R 6a is as defined above and is in particular selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, Ci-C2-alkoxy, such as methoxy or ethoxy, and Ci-C
  • R 6a is more particularly selected from halogen and C1-C2- haloalkyl, and especially from chlorine, bromine and trifluoromethyl (CF3), and is very especially chlorine.
  • halogen and C1-C2- haloalkyl and especially from chlorine, bromine and trifluoromethyl (CF3), and is very especially chlorine.
  • CF3 trifluoromethyl
  • a particular subgroup 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 b:
  • R 6a is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy.
  • halogen such as fluorine, chlorine or bromine
  • Ci-C2-alkyl such as methyl or ethyl
  • Ci-C2-haloalkyl such as difluoromethyl,
  • R 6a is more particularly selected from halogen and Ci-C2-haloalkyl, and especially from chlorine, bromine and trifluoromethyl (CF3), and is very especially chlorine
  • R 6a1 is hydrogen or has one of the meanings given for R 6a , and is in particular selected from the group consisting of hydrogen, halogen, such as chlorine or fluorine, and Ci-C4-alkyl, such as methyl or ethyl.
  • Het-1 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 6a is selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy. Irrespectively of its occurrence, R 6a is more particularly selected from halogen and
  • a special embodiment of the radical Het-1 a is 6-chloropyridin-3-yl, i.e. R 6a is chlorine.
  • a further special embodiment of the radical Het-1 a is 6-(trifluoromethyl)pyridin-3-yl, i.e. R 6a 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-4, where j is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-4a:
  • R 6a is as defined above in particular selected from the group consisting of halogen, Ci-C4-alkyl, C1-C4- haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy. Irrespectively of its occurrence, R 6a is more particularly selected from halogen and Ci-C2-alkyl, C1-C4- haloalkyl, Ci-C
  • a special embodiment of the radical Het-4a is 2-chloropyrimidin-5-yl, i.e. R 6a is chlorine.
  • a further special embodiment of the radical Het-4a is 2-(trifluoromethyl)pyrimidin-5-yl, i.e. R 6a 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-7, where j is 0, 1 or 2, in particular 0 or 1 , and where Het is in particular a radical of formula Het-7b:
  • R 6a is selected from the group consisting of halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, even more preferably from halogen, such as fluorine, chlorine or bromine, Ci-C2-alkyl, such as methyl or ethyl, Ci-C2-haloalkyl, such as difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl or pentafluoroethyl, C1-C2- alkoxy, such as methoxy or ethoxy, and Ci-C2-haloalkoxy, such as difluoromethoxy or trifluoromethoxy. Irrespectively of its occurrence, R 6a is more particularly selected from halogen and Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy, and Ci
  • a special embodiment of the radical Het-7b is 2-chlorothiazol-5-yl, i.e. R 6a is chlorine.
  • R 1 and R 2 are independently of 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
  • R 1 and R 2 form, together with the carbon atom, which they attached to, a 3-, 4- or 5-membered saturated carbocyclic ring such as cyclopropyl, cyclobutyl or cyclopentyl.
  • R 1 and R 2 are independently of 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 3a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, (C3-C6- cycloalkyl)-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)-Ci-C 6 -alkyl, NR 9a R 9b -(Ci-C 6 -alkyl), where the aliphatic parts of the 7 last mentioned radicals are unsubstituted, partly or completely halogenated;
  • phenyl or phenyl-Ci-C6 alkyl wherein phenyl in the last 2 mentioned radicals is unsubstituted or substituted by 1 , 2, 3, 4 or 5 identical or different substituents selected from the group consisting of halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy and d-Ce-haloalkoxy;
  • R 3a is selected from the group consisting of hydrogen, Ci-C6-alkyl,
  • R 3a is selected from the group consisting of hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl;
  • R 3a is selected from the group consisting of hydrogen, Ci-C4-alkyl, such as CH3, CH3CH2, CH(CH 3 ) 2 , CH 2 CH(CH 3 )2, C(CH 3 ) 3 and Ci-C 4 -haloalkyl, such as
  • R 9a and R 9b are as defined above and are in particular independently selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C 3 -C8-cycloalkyl, C 3 -C8-halocycloalkyl, C 3 -C8-cycloalkyl-Ci-C 4 -alkyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, phenyl and benzyl,
  • R 9a and R 9b are independently selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl,
  • R 9a and R 9b are independently selected from the group consisting of hydrogen and Ci-C 4 -alkyl
  • radicals R 9a and R 9b are hydrogen, and specifically R 9a and R 9b are both hydrogen.
  • R 3b and R 3c are independently of one another selected from Ci-C6-alkyl, C 2 -C6-alkenyl, C 2 -C6-alkynyl, C 3 -C6- cycloalkyl, (C 3 -C 6 -cycloalkyl)-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)-Ci-C 6 -alkyl, NR 9a R 9 -(Ci-C 6 -alkyl), where the aliphatic parts of the 7 last mentioned radicals are unsubstituted, partly or completely halogenated; phenyl and phenyl-Ci-C6-alkyl, wherein phenyl in the last 2 mentioned radicals is unsubstituted or substituted by 1 ,
  • R 3b and R 3c are independently of one another selected from the group consisting of hydrogen, Ci-C6-alkyl, (Ci-C6-alkoxy)-Ci-C6-alkyl, C 3 -C6-cycloalkyl and (C 3 -C6- cycloalkyl)-Ci-C6-alkyl, where the aliphatic parts of the last 4 mentioned radicals unsubstituted, partly or completely halogenated;
  • R 3b and R 3c are independently of one another selected from the group consisting of hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl;
  • R 3b and R 3c are independently of one another selected from the group consisting of hydrogen, Ci-C 4 -alkyl, such as CH 3 , CH 3 CH 2 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , or C(CH 3 ) 3 , and Ci-C 4 -haloalkyl, such as CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , CF(CH 3 ) 2 , CH(CF 3 ) 2 or CH(CH 3 )CF 3 .
  • Ci-C 4 -alkyl such as CH 3 , CH 3 CH 2 , CH(CH 3 ) 2 , CH 2 CH(CH 3 ) 2 , or C(CH 3 ) 3
  • Ci-C 4 -haloalkyl such as CF 3 , CHF 2 , CH 2 F, CH 2 CF 3 , CF(CH 3 ) 2 , CH(CF 3 ) 2 or CH(CH 3 )CF 3 .
  • N-bound saturated monoheterocyclic radical which may have 1 or 2 further heteroatoms which are selected from N and O as ring members, which heterocyclic radical is unsubstituted or substituted by 1 , 2, 3, or 4 identical or different substituents selected from the group consisting of halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy, in particular selected from the group consisting of halogen, CN, NO2, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C2-haloalkoxy;
  • R 3b and R 3c together with the nitrogen atom to which they are bound, form an N-bound saturated mono- or bicyclic heterocyclic radical which is selected from the group consisting of 1-aziridinyl, 1-azetidinyl, 1-piperidinyl, 1-pyrrolidinyl, azepan-1-yl, azocan-1-yl, morpholin-4-yl, isoxazolidine-2-yl, oxazolidine-3-yl, piperazine-1-yl, octahydroisoindol-2-yl, octahydroindol-1-yl, octahydro-2H-quinolin-1-yl, azabicyclo[2.2.1]heptan-3-yl and
  • azabicyclo[2.2.1]heptan-7-yl where the aforementioned radicals are unsubstituted or substituted by one or more identical or different substituents selected from the group consisting of halogen, CN, NO2, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C2-haloalkoxy;
  • R 3b and R 3c together with the nitrogen atom to which they are bound, form an N-bound saturated monocyclic heterocyclic radical which is selected from the group consisting of 1-piperidinyl, 1-pyrrolidinyl, azepan-1-yl, azocan-1-yl and morpholin-4-yl, where the aforementioned radicals are unsubstituted or substituted by one or more identical or different substituents selected from the group consisting of halogen, CN, NO2, Ci-C2-alkyl, Ci-C2-haloalkyl, Ci-C2-alkoxy and Ci-C2-haloalkoxy.
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6- cycloalkyl, (C 3 -C 6 -cycloalkyl)-Ci-C 6 -alkyl, (Ci-C 6 -alkoxy)-Ci-C 6 -alkyl, NR 9a R 9 -(Ci-C 6 -alkyl) and NR 9a R 9b , where the aliphatic parts of the 7 last mentioned radicals are unsubstituted, partly or completely halogenated; phenyl and phenyl-Ci-C6 alkyl, wherein phenyl in the last 2 mentioned radicals is unsubstituted or
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl,
  • R 3d is selected from the group consisting of hydrogen, Ci-C6-alkyl and C1-C6- haloalkyl;
  • R 3d is selected from the group consisting of hydrogen, Ci-C4-alkyl, such as CH3, CH3CH2, CH(CH 3 ) 2 , CH 2 CH(CH 3 )2 or C(CH 3 ) 3 , and Ci-C 4 -haloalkyl, such as CF 3 , CHF 2 , CH2F, CH2CF3, CF(CH 3 ) 2 , CH(CF 3 ) 2 or CH(CH 3 )CF 3 .
  • variable m is preferably 0 or 2 and especially 0.
  • R 4 and R 5 are independently of each other selected from the group consisting of hydrogen, halogen, CN, azido, nitro, SCN, SF 5 , Si(R 11 ) 2 R 12 , OR 8 , Ci-C 6 -alkyl, C 3 -C 8 -cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the 4 last-mentioned aliphatic and cycloaliphatic radicals may be partly or completely halogenated and/or may carry one or more radicals R 7 , wherein R 7 is as defined above;
  • R 4 and R 5 independently of each other, are selected from the group consisting of hydrogen, halogen, CN, Si(Ci-C6-alkyl)3, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, wherein the aliphatic and cycloaliphatic moieties of the 6 last-mentioned radicals may be partly or completely halogenated and/or may carry one or more radicals R 7 , wherein R 7 is selected from Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6-
  • W.Het-1 is selected from the group consisting of radicals of formulae: W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11 , W.Het-12, W.Het-13, W.Het 14, W.Het 15, W.Het 16 and W.Het 17:
  • R 6 is as defined above and is in particular selected from the group consisting of halogen, such as fluorine or chlorine, CN, Ci-C4-alkyl, such as methyl, ethyl, n-propyl and isopropyl, C1-C4- haloalkyl, in particular Ci-C2-haloalkyl, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular C1-C2- haloalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1
  • W.Het is selected from the group consisting of W.Het-1 , W.Het-2, W.Het-3, W.Het 4 and W.Het 13, wherein R 6 is as defined above and in particular selected from the group consisting of halogen, such as fluorine or chlorine, 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 -d if I uoroethyl , 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, eth
  • the heterocycle Het is in particular selected from the group consisting of the radicals of formulae Het-1 to Het-7, as defined above, and in particular selected from the group consisting of the radicals of the formulae Het-1 or Het-1 a, Het-4 or Het-4a and Het-7a or Het-7b.
  • the radicals R 1 and R 2 are, independently of each other, in particular 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,
  • the radicals R 1 and R 2 are, independently of each other, more particularly selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl, ethyl or isopropyl, and Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at least one of the radicals R 1 and R 2 is hydrogen.
  • R 1 and R 2 in the moieties W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-11 , W.Het-12, W.Het-13, W.Het 14, W.Het 15, W.Het 16 and W.Het 17 are both hydrogen.
  • a particular group (a) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-1 , wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-4 and Het-7a.
  • a particular group (b) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-2, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-4 and Het-7a.
  • a particular group (c) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-3, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-4 and Het-7a.
  • a particular group (d) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-4, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-4 and Het-7a.
  • a particular group (e) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-13, wherein Het is selected from the group consisting of radicals of formulae Het-1 , Het-4 and Het-7a.
  • a special group (aa) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W. Het-1 , wherein Het is a radical of formula Het-1 a.
  • a further special group (ba) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-2, wherein Het is a radical of formula Het-1 a.
  • a further special group (ca) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-3, wherein Het is a radical of formula Het-1 a.
  • a further special group (da) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W. Het-4, wherein Het is a radical of formula Het-1 a.
  • a further special group (ea) of embodiments relates to compounds of the formula (I), to their stereoisomers, their tautomers and their salts, and likewise to the compounds of groups (1 ), (2), (2a) and (3) embodiments, wherein the moiety of W.Het represents a radical selected from the group consisting of W.Het-13, wherein Het is a radical of formula Het-1 a.
  • the radical R 6 is as defined above and in particular selected from the group consisting of halogen, such as fluorine or chlorine, 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 -d if I uoroethyl , 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, Ci-C4-alkoxy, such as methoxy, ethoxy, n-propoxy and isopropoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy, such as fluorometh
  • radicals R 1 and R 2 are, independently from each other, in particular 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
  • radicals R 1 and R 2 are, independently of each other, more particularly selected from the group consisting of hydrogen, halogen, cyano, Ci-C3-alkyl, such as methyl, ethyl or isopropyl, and Ci-C3-haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 ,1-difluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl or 2,2,2-trifluoroethyl, where in particular at least one of the radicals R 1 and R 2 is hydrogen and where especially both R 1 and R 2 are hydrogen.
  • W. Het is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het- 9, W.Het-10, W.Het-11 , W.Het-12, W.Het-13, W.Het-14, W.Het-15, W.Het-16 and W.Het 17 and likewise in groups (1 ), (2), (2a), (3), (a), (b), (c), (d), (e), (aa), (ba), (ca), (da), and (ea) of embodiments, the variables R 1 , R 2 , R 4 , R 5 and Z are as defined above and in particular have the preferred meanings.
  • the variables R 1 , R 2 independently of each other or in particular in combination, in particular 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
  • X is in particular O.
  • X is in particular S.
  • W.Het is selected from the moieties of formulae W.Het-1 , W.Het-2, W.Het-3, W.Het-4, W.Het-5, W.Het-6, W.Het-7, W.Het-8, W.Het-9, W.Het-10, W.Het-
  • the variables R 1 , R 2 independently of each other or in particular in combination, more particularly 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, where in particular at
  • R 7 irrespectively of its occurrence, is selected from the group consisting of CN, C1-C6- alkoxy, Ci-C6-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, C1-C6- haloalkylsulfonyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, Ci-C6-alkoxycarbonyl, C1-C6- haloalkoxycarbonyl.
  • 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-difluoroeth
  • R 8 irrespectively of its occurrence, is selected from the group consisting of hydrogen
  • halogen such as chlorine or fluorine
  • R 9a and R 9b are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, and Ci-C4-haloalkyl, 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-C4-alkyl and Ci-C4-haloalkyl.
  • heterocyclic radicals NR 9a R 9b include, but are not limited to 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinly, 4-methyl-1-piperazinly and 4-morpholinyl.
  • R 10 irrespectively of its occurrence, is selected from the group consisting of halogen, such as chlorine or fluorine, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl,
  • Ci-C4-alkoxy and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy.
  • 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 rings 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, C1-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, C3-C6-cycloalkyl, and phenyl.
  • R 16 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, CN, C1-C4- alkyl, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy.
  • 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, Ci-C4-haloalkyl, in particular Ci-C2-haloalkyl, Ci-C4-alkoxy, and Ci-C4-haloalkoxy, in particular Ci-C2-haloalkoxy.
  • halogen such as chlorine or fluorine
  • R 17a and R 17b irrespectively of their occurrence, are preferably selected from the group consisting of hydrogen, Ci-C4-alkyl, and Ci-C4-haloalkyl, 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-C4-alkyl and Ci-C4-haloalkyl.
  • heterocyclic radicals NR 17a R 17b include, but are not limited to 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinly, 4-methyl-1-piperazinly and 4-morpholinyl.
  • R 18 irrespectively of its occurrence, is selected from the group consisting of C1-C4- alkyl and Ci-C4-alkoxy.
  • R 19 irrespectively of its occurrence, is selected from the group consisting of CN,
  • a special group of embodiments relates to the compounds of formulae la.1 to la.8, wherein R 3a , R 4 , R 5 , and R 6a have one of the meanings given above.
  • Examples of preferred compounds are the individual compounds compiled in the tables 1 to 815 below.
  • the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in uestion.
  • the compounds of formula (I) according to the present invention can be prepared e.g. according the preparation methods and preparation schemes as described below.
  • Compounds of formula (I) according to the present invention can be prepared by standard methods of organic chemistry e.g. by the preparation methods and preparation schemes as described below.
  • the definitions of Het, X, Z, R 1 , R 2 , R 4 , R 5 , R 6 and k of the molecular structures given in the schemes are as defined above.
  • Room temperature means a temperature range between about 20 and 25 °C.
  • the synthesis of compounds of formula 5 can be achieved by acylation of the amine functionality in compounds of formula 3 using carboxylic acid derivatives 4 which may or may not be activated in situ.
  • the transformation is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyrolidinone or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room
  • polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N-dimethylformamide, ⁇ , ⁇ -dimethylacetamide, N-methylpyrolidinone
  • an inert solvent such as dichloromethane, 1 ,2-
  • LG 2 Suitable leaving groups in formula 4 include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphoante, halophosphate and various activated esters derived from the reaction of a free carboxylic acid with a peptide coupling reagent in the presence of an amine base (Chem. Rev., 2011 , 777 (11), 6557-6602). A reversal of the order of these two steps would also result in an acceptable synthesis of the desired compounds.
  • heterocyclic element 3 present in compounds of formula (I) can be achieved, for example, by alkylation of the appropriate 2-amino heterocycle precursor 1 with the appropriate reagent of formula 2.
  • the transformation is preferably carried out in polar solvents such as acetonitrile, acetone, dichloromethane, 1 ,4-dioxane, tetrahydrofuran,
  • Representative reaction conditions for the alkylation of compounds analogous to formula 1 are given in Tett. Lett. 2011 , 52(23), 3033-3037.
  • the synthesis of compounds of formula 5 can be achieved by acylation of the amine functionality in compounds of formula 3 using carboxylic acid derivatives 4 which are activated in situ. The transformation is preferably carried out in polar solvents such as acetonitrile, acetone, 1 ,4-dioxane, tetrahydrofuran, N,N-dimethylformamide,
  • LG 2 examples include, but are not limited to: halogen, alkyl sulfonate, haloalkyl sulfonate, aryl sulfonate, alkyl phosphoante and various activated esters derived from the reaction of a free carboxylic acid with a peptide coupling reagent in the presence of an amine base;
  • the carbonyl compound 5 is transformed into the thiocarbonyl compound 7.
  • the transformation is preferably carried out using a reagent of substructure 8 in polar solvents such as acetonitrile, acetone, tetrahydrofuran, ⁇ , ⁇ -dimethylformamide, or in an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • polar solvents such as acetonitrile, acetone, tetrahydrofuran, ⁇ , ⁇ -dimethylformamide
  • an inert solvent such as dichloromethane, 1 ,2-dichloroethane, or 1 ,2-dimethoxyethane at temperatures ranging between room temperature and the reflux temperature of the solvent.
  • Suitable R p groups in compounds of formula 8 are: thio, Ci-C4-alkyl, aryl, such as phenyl which is unsubstituted or substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl or Ci-C4-alkoxy.
  • Representative reaction conditions for thionation analogous substrates are given in European Journal of Organic Chemistry, 2000, 3273-3278, and Chemical Reviews, 2007, 107, 5210-5278.
  • reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by
  • intermediates and end products may be obtained in the form of colorless or pale brown viscous oils, which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or digestion.
  • the compounds of the present invention may be used for controlling invertebrate pests.
  • the present invention also provides a method for combatting or controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of the present invention or a composition as defined above.
  • the invention also relates to the use of a compound of the invention, of a stereoisomer and/or of an agriculturally or veterinarily acceptable salt thereof for combating invertebrate pests
  • the method of the invention serves for protecting plant propagation material
  • the method of the invention is not limited to the protection of the "substrate" (plant, plant propagation materials, soil material etc.) which has been treated according to the invention, but also has a preventive effect, thus, for example, according protection to a plant which grows from a treated plant propagation materials (such as seed), the plant itself not having been treated.
  • the method of the invention serves for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the invention, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.
  • invertebrate pests are preferably selected from arthropods, gastropods and nematodes, more preferably from harmful insects, arachnids and nematodes, and even more preferably from insects, acarids and nematodes. In the sense of the present invention, “invertebrate pests” are most preferably insects.
  • the invention further provides an agricultural composition for combating invertebrate pests, which comprises such an amount of at least one compound according to the invention and at least one inert liquid and/or solid agronomically acceptable carrier that has a pesticidal action and, if desired, at least one surfactant.
  • compositions may comprise a single active compound of the present invention or a mixture of several active compounds of the present invention.
  • the composition according to the present invention may comprise an individual isomer or mixtures of isomers or a salt as well as individual tautomers or mixtures of tautomers.
  • the compounds of the present invention are in particular suitable for efficiently controlling animal pests such as arthropods, gastropods and nematodes including but not limited to:
  • insects from the order of Lepidoptera for example Achroia grisella, Aden ' s spp. such as A. fimbriana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.
  • Austroasca viridigrisea Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedellia spp., Bonagota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C.
  • Dendrolimus spp. such as D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiose/la, Diatraea saccharalis, Diphthera festiva, Ear/as spp. such as E. insu/ana, E.
  • kuehniella kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eu/ia spp., Eupoecilia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bou liana, Faronta albilinea, Feltia spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapho/ita spp. such as G.
  • H. armigera Heliothis armigera
  • H. zea Heliothis zea
  • Heliothis spp. such as H. assuita, H. subfiexa, H. virescens
  • Hellula spp. such as H. undalis, H.
  • M. neustria M. neustria
  • Mamestra spp. such as M. brassicae, M. configurata
  • Mamstra brassicae Manduca spp.
  • M. quinquemaculata M. sexta
  • Mods spp. such as M. lapites, M.
  • operculella Phyllocnistis citrella, Phyllonorycter spp. such as P. blancardella, P. crataegeiia, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P.
  • Thaumetopoea pityocampa Thecla spp., Theresimima ampelophaga, Thyrinteina spp, Tildenia inconspicuella, Tinea spp. such as T. cloacella, T. pellionella; Tineola bisselliella, Tortrix spp. such as T. viridana; Trichophaga tapetzella, Trichoplusia spp. such as T. ni; Tuta
  • insects from the order of Coleoptera for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anxius, A. planipennis, A. sinuatus; Agriotes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimaiius soistitiaiis, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomala diverenta, Anomala rufocuprea, Anoplophora spp. such as A.
  • Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum
  • Anthrenus spp. Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis
  • Attagenus spp. Aulacophora fern oral is, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B.
  • Curculio spp. Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa ba/yi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. longicornis, D. semipunctata, D. virgifera; Diaprepes abbreviates, Dichocrocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra stigmaticollis), Enaphalodes rufulus, Epilachna spp. such as E. varivestis, E.
  • vigintioctomaculata Epitrix spp. such as E. hirtipennis, E. similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brunneipennis, H.
  • hypomeces squamosus Hypothenem us spp., Ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decern lineata; Leptispa pygmaea, Limonius californicus,
  • Lissorhoptrus oryzophilus Lixus spp., Luperodes spp., Lyctus spp. such as L. bruneus;
  • Liogenys fuscus Macrodactylus spp. such as M. subspinosus
  • Maladera matrida Megapiatypus mutates, Megascelis spp., Me/anotus communis, Meligethes spp. such as M. aeneus
  • M. subspinosus Maladera matrida, Megapiatypus mutates, Megascelis spp., Me/anotus communis, Meligethes spp. such as M. aeneus
  • Meioiontha spp. such as M. hippocastani, M. meioiontha; Metamasius hemipterus, Microtheca spp., Migdolus spp. such as M. fryanus, Monochamus spp. such as M. alternatus; Naupactus xanthographus, Niptus hololeucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros,
  • chrysocephala P. nemorum, P. striolata, P. vittula; Phyllopertha horticola, Pop/ilia japonica, Premnotrypes spp., Psacothea hilaris, Psylliodes chrysocephala, Prostephanus truncates, Psylliodes spp., Ptinus spp., Pulga saltona, Rhizopertha dominica, Rhynchophorus spp. such as R. billineatus, R. ferrugineus, R. palmarum, R. phoenicis, R.
  • Saperda Candida Scolytus schevyrewi, Scyphophorus acupunctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp. such as T.
  • Trogoderm a spp. Tychius spp.
  • Xylotrechus spp. such as X. pyrrhoderus
  • Zabrus spp. such as Z. tenebrioides
  • insects from the order of Diptera for example Aedes spp. such as A. aegypti, A.
  • albopictus A. vexans
  • Anastrepha ludens Anopheles spp.
  • A. albimanus A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A. sinensis
  • Bactrocera invadens Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. macellaria;
  • Contarinia spp. such as C. sorghicola
  • Cordylobia anthropophaga Culexspp. such as C. nigripalpus, C. pip/ens, C. quinquefasciatus, C. tarsalis, C. tritaeniorhynchus;
  • Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectoralis, Mansonia titillanus, Mayetiola spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. such as O. ovis;
  • Opomyza florum Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami,
  • Phlebotomus argentipes Phorbia spp. such as P. antiqua, P. brassicae, P. coarctata;
  • insects from the order of Thysanoptera for example, Basothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femora/is, Kakothrips spp., Microcephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus,
  • Stenchaetothrips spp Taeniothrips cardamom, ' Taeniothrips inconsequens, Thrips spp. such as
  • insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Adelges laricis, Adelges tsugae, Adelphocoris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Auiacorthum soiani, Aleurocanthus woglumi, Aleurodes spp., Aleurodicus disperses,
  • Aspidiotus spp. Atanus spp., Auiacaspis yasumatsui, Auiacorthum soiani, Bactericera cockereiii
  • Bemisia spp. such as B. argentifolii, B. tabaci (Aleurodes tabaci); Blissus spp. such as B. leucopterus; Brachycaudus spp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola; Brachycolus spp., Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C.
  • C. hemipterus, C. lectularius Coccomytilus halli, Coccus spp. such as C hesperidum, C. pseudomagnoliarum, Corythucha arcuata, Creontiades dilutus, Cryptomyzus ribis, Chrysomphalus aonidum, Cryptomyzus ribis, Ctenarytaina spatuiata, Cyrtopeltis notatus, Dalbulus spp., Dasynus piperis, Dialeurodes spp. such as D. citrifolii;
  • Diaphorina spp. such as D. citri
  • Diaspis spp. such as D. bromeliae
  • Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola
  • Dysaulacorthum pseudoso/ani Dysdercus spp. such as D. cingulatus, D.
  • Dysmicoccus spp. Edessa spp., Geocoris spp., Empoasca spp. such as E. fabae, E. solana; Epidiaspis leperii, Eriosoma spp. such as E. lanigerum, E. pyricola; Erythroneura spp., Eurygaster spp. such as E. integriceps; Euscelis bilobatus, Euschistus spp. such as E. heros, E. impictiventris, E.
  • Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; Heliopeltis spp., Homalodisca vitripennis ( H. coagulata), Horcias nobilellus, Hyalopterus pruni, Hyperomyzus lactucae, lcerya spp. such as /. purchase; Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepidosaphes spp. such as L. ulmi; Leptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L.
  • Nephotettix spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viridula;
  • Parthenolecanium spp. such as P. corn/, P. persicae; Pemphigus spp. such as P. bursar/us, P. popuiivenae; Peregrinus maidis, Perkinsiella saccharic/da, Phenacoccus spp. such as P. aceris, P. gossypii; Ph/oeomyzus passer/nil, Phorodon humu/i, Phylloxera spp. such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P.
  • Trialeurodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,
  • Iridomyrmex humilis Lasius spp. such as L. niger, Linepithema humile, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nylandria fulva, Pachycondyla chinensis, Paratrechina longicornis, Paravespula spp., such as . germanica, P. pennsyivanica, P. vulgaris; Pheidoie spp. such as P. megacephala; Pogonomyrmex spp. such as . barbatus, P.
  • Tetramorium spp. such as T. caespitum, T. bicarinatum, Vespa spp. such as V. crabro; Vespula spp. such as V. squamosal; Wasmannia auropunctata, Xy loco pa sp;
  • Chortoicetes terminifera Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardalina; Meianopius spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M.
  • Pests from the Class Arachnida for example Acari, e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A americanum, A. variegatum, A.
  • Argas spp. such as A. persicu
  • Boophilus spp. such as B. annulatus, B.
  • Eriophyidae including Acer/a spp. such as A. she/doni, A. anthocoptes, Acallitus spp., Aculops spp. such as A. iycopersici, A. pe/ekassi, Acu/us spp. such as A. sch/echtenda/i; Colomerus vitis, Epitrimerus pyri, Phyllocoptruta oleivora; Eriophytes ribis and Eriophyes spp.
  • Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae, Bryobia praetiosa, Panonychus spp. such as P. ulmi, P. citri,
  • Metatetranychus spp. and O/igonychus spp. such as O. pratensis, O. perseae, Vasates
  • Iycopersici Raoiella indica, /3 ⁇ 4/77// Carpoglyphidae including Carpoglyphus spp.; Penthaleidae spp. such as a/otydeus destructor, Family Demodicidae with species such as Demodexspp:, Family Trombicidea including Trombicula spp:, Family Cellyssidae including Ornothonyssus spp:, Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae; Family Acaridae including Acarus siro; Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles rec/usa;
  • Pests from the Phylum Nematoda for example, plant parasitic nematodes such as root- knot nematodes, Meloidogyne spp. such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifo/ii; Seed gall nematodes, Anguina spp:, Stem and foliar
  • nematodes Aphe/enchoides spp. such as A. besseyi; Sting nematodes, Be/ono/aim us spp. such as B. longicaudatus; Pine nematodes, Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ring nematodes, Criconema spp., Criconemella spp. such as C. xenop/axand C. ornata; and, Criconemoides spp. such as Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Ditylenchus spp.
  • brachyurus P. neglectus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as R. similis; Rhadopholus spp.; Rhodopholus spp.; Reniform
  • nematodes Rotylenchus spp. such as R. robustus, R. reniformis; Scutellonema spp.; Stubby- root nematode, Trichodorus spp. such as T. obtusus, T. primitivus; Paratrichodorus spp. such as . minor; Stunt nematodes, Tylenchorhynchus spp. such as 7! claytoni, T. dub/us; Citrus nematodes, Tylenchulus spp. such as 7! semipenetrans; Dagger nematodes, Xiphinema spp.; and other plant parasitic nematode species;
  • Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticollis, Z. nevadensis, Reticulitermes spp. such as R. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R.
  • Insects from the order Blattaria for example Blatta spp. such as B. orientalis, B. lateralis; Blattella spp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchlora nivea,
  • Peripianeta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuiigginosa, P. japonica; Supella longipaipa, Parcobiatta pennsylvanica, Eurycotis floridana, Pycnoscelus surinamensis, Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. such as C. felis, C. cam ' s, Xenopsylla cheopis, Pulex irritans,
  • Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Therm obia domes tica,
  • Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata, Pests from the class Diplopoda for example Blaniulus guttulatus, Ju/us spp., Narceus spp.,
  • Pests from the class Symphyla for example Scutigerella immaculata
  • Onychiurus spp. such as Onychiurus armatus
  • Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,
  • Pedicuius spp. such as Pedicuius humanus capitis, Pedicuius humanus corporis, Pedicuius humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis,
  • Linognathus spp. such as Linognathus vituii; Bovicoia bovis, Menopon gaiiinae, Menacanthus stramineus and Solenopotes capillatus, Trichodectes spp.,
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp:, class
  • Gastropoda for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, for example, Ancyiostoma duodenale, Ancyiostoma ceylanicum, Acylostoma braziiiensis, Ancyiostoma spp., Ascaris lubricoides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., C ha bertia spp., Clonorchis spp., Cooper/a spp., Dicrocoelium spp.,
  • Dictyocaulus filaria Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.
  • Haemonchus contortus such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni,
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount" is defined below.
  • the compounds of the present invention or the mixtures thereof can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • suspensions e.g. SC, OD, FS
  • emulsifiable concentrates e.g. EC
  • emulsions e.g. EW, EO, ES, ME
  • capsules e.g. CS, ZC
  • compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfatants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin,
  • tetrahydronaphthalene alkylated naphthalenes
  • alcohols e.g. ethanol, propanol, butanol, benzylalcohol, cyclo ⁇ hexanol
  • glycols DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates;
  • amines e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch;
  • fertilizers e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas
  • products of vegetable origin e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 :
  • Emulsifiers & Detergents McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and
  • tridecylbenzenes sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water-soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I according to the invention 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%.
  • the active substance dissolves upon dilution with water.
  • a compound I according to the invention 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvinylpyrrolidone
  • organic solvent e.g. cyclohexanone
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • Emulsions EW, EO, ES 5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water- insoluble organic solvent (e.g. aromatic hydrocarbon).
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water- insoluble organic solvent e.g. aromatic hydrocarbon
  • lignosulfonate and alcohol ethoxylate 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance.
  • wt% binder e.g.
  • polyvinylalcohol is added.
  • 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a compound I according to the invention In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. carboxymethylcellulose
  • 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • Microcapsules An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4'-diisocyanatae are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of a polyurea microcapsule.
  • the monomers amount to 1-10 wt%.
  • the wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray- drying or the fluidized bed.
  • solid carrier e.g. silicate
  • 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • organic solvent e.g. aromatic hydrocarbon.
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • auxiliaries such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions cormprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above or below, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above or below, can be applied jointly (e.g. after tank mix) or consecutively.
  • the compounds of the present invention are suitable for use in protecting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the present invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, such as seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are also suitable for use in combating or controlling animal pests. Therefore, the present invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, such as seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are effective through both contact and ingestion.
  • the compounds of the present invention can be applied to any and all
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and
  • the term "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • crop refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias,
  • geranium/pelargoniums pansies and impatiens
  • shrubs broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including wild type plants and plants which have been modified by either conventional breeding or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
  • rapeseed e.g. oilseed rape
  • the one or more mutagenized or integrated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • Such properties include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • mutagenesis for example Clearfield® oilseed rape being tolerant to imidazolinones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance.
  • Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thuringiensis (Bt), and code for the respective Bt toxins.
  • Genetically modified plants with insect resistance are commercially available under trade names including WideStrike®, Bollgard®, Agrisure®, Herculex®, YieldGard®, Genuity®, and Intacta®. Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance.
  • all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations "International Service for the Acquisition of Agribiotech Applications (ISAAA)"
  • the pesticidal activity of the compounds of the present invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant.
  • seedlings and young plants which are to be transplanted after germination or after emergence from soil, may also be included.
  • These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
  • the present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermination with a compound of the present invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in- furrow application methods.
  • seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the present invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the
  • propagation product depending on the method of application.
  • the said propagation product When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias,
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having
  • the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20% by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40% by weight, e.g.
  • a binder optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100% by weight.
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the present invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the compounds of the present invention may also be used for improving the health of a plant. Therefore, the present invention also relates to a method for improving plant health by treating a plant, plant propagation material and/or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the present invention.
  • an effective and non-phytotoxic amount means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil.
  • plant and “plant propagation material” are defined above.
  • Plant health is defined as a condition of the plant and/or its products which is determined by several aspects alone or in combination with each other such as yield (for example increased biomass and/or increased content of valuable ingredients), quality (for example improved content or composition of certain ingredients or shelf life), plant vigour (for example improved plant growth and/or greener leaves ("greening effect"), tolerance to abiotic (for example drought) and/or biotic stress (for example disease) and production efficiency (for example, harvesting efficiency, processability).
  • yield for example increased biomass and/or increased content of valuable ingredients
  • quality for example improved content or composition of certain ingredients or shelf life
  • plant vigour for example improved plant growth and/or greener leaves ("greening effect")
  • tolerance to abiotic for example drought
  • biotic stress for example disease
  • production efficiency for example, harvesting efficiency, processability
  • the above identified indicators for the health condition of a plant may be interdependent and may result from each other.
  • Each indicator is defined in the art and can be determined by methods known to a skilled person.
  • the compounds of the invention are also suitable for use against non-crop insect pests.
  • compounds of the present invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.
  • non-crop insect pest refers to pests, which are particularly relevant for non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitos, crickets, or cockroaches.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • the bait employed in the composition is a product, which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
  • the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
  • Food stimulants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature (e.g. http://www.pherobase.com), and are known to those skilled in the art.
  • the typical content of active ingredient is from 0.001 weight% to 15 weight%, desirably from 0.001 weight% to 5% weight% of active compound.
  • Formulations of the compounds of the present invention as aerosols e.g in spray cans), oil sprays or pump sprays are highly suitable for the non-professional user for controlling pests such as flies, fleas, ticks, mosquitos or cockroaches.
  • Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries such as emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.
  • the oil spray formulations differ from the aerosol recipes in that no propellants are used.
  • the content of active ingredient is from 0.001 to 80 weights%, preferably from 0.01 to 50 weight% and most preferably from 0.01 to 15 weight%.
  • the compounds of the present invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
  • Methods to control infectious diseases transmitted by insects e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis
  • compounds of the present invention and its respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like.
  • Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder.
  • the compounds of the present invention and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
  • Customary application rates in the protection of materials are, for example, from
  • Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight%, preferably from 0.1 to 45 weight%, and more preferably from 1 to 25 weight% of at least one repellent and/or insecticide.
  • the compounds of the present invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the present invention also relates to the use of a compound of the present invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites.
  • the present invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the present invention.
  • the present invention also relates to the non-therapeutic use of compounds of the present invention for treating or protecting animals against infestation and infection by parasites.
  • the present invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
  • the compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the present invention relates to a method of combating or controlling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the present invention.
  • the present invention also relates to the non-therapeutic use of compounds of the present invention for controlling or combating parasites. Moreover, the present invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the present invention.
  • the compounds of the present invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the present invention can be applied to any and all developmental stages.
  • the compounds of the present invention can be applied as such or in form of
  • compositions comprising the compounds of the present invention.
  • the compounds of the present invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics such as Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin,
  • the compounds of the present invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally.
  • the compounds of the present invention can be systemically or non-systemically effective.
  • the application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.
  • the term "contacting" includes both direct contact (applying the compounds/compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at it's locus for the latter) and indirect contact (applying the compounds/compositions to the locus of the parasite).
  • the contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the present invention.
  • locus means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.
  • parasites includes endo- and ectoparasites. In some embodiments of the present invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.
  • the compounds of the present invention are especially useful for combating parasites of the following orders and species, respectively:
  • fleas e.g. Ctenocephalides felis, Ctenocephalides cam ' s, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus
  • cockroaches e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis
  • flies mosquitoes (Diptera), e.g.
  • Hippelates spp. Hypoderma lineata, Leptoconops torrens, Lu cilia caprina, Lu cilia cuprina, Lu cilia sericata, Lycoria pectoral is, Mansonia spp., Musca domes tica, Muscina stab u I an s, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis; lice (Phthiraptera), e.g.
  • Pediculus humanus capitis Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capHlatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g.
  • Haematopinus spp. Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and
  • Trichinosis Trichosyringida
  • Trichinellidae Trichinella spp.
  • Trichuridae Trichuridae
  • Trichuris spp. Capillaria spp.
  • Rhabditida e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.
  • Rhabditida e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.
  • Strongylida e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus, Ostertagia spp., Cooper/a spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp.,
  • Acanthocephala e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.
  • Planarians Plathelminthes: Flukes (Trematoda), e.g.
  • Faciola spp. Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis busk/, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp:, Cercomeromorpha, in particular Cestoda (Tapeworms), e.g.
  • animal includes warm-blooded animals (including humans) and fish.
  • mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur- bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.
  • domestic animals such as dogs or cats.
  • parasiticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the parasiticidally effective amount can vary for the various compounds/compositions used in the invention.
  • a parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.
  • the compounds of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.
  • the formula I compounds may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules.
  • the formula I compounds may be administered to the animals in their drinking water.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.
  • the formula I compounds may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection.
  • the formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection.
  • the formula I compounds may be formulated into an implant for subcutaneous administration.
  • the formula I compound may be transdermally administered to animals.
  • the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound.
  • the formula I compounds may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions.
  • dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the formula I compound.
  • the formula I compounds may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.
  • Suitable preparations are:
  • Solutions such as oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;
  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.
  • compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further auxiliaries such as acids, bases, buffer salts, preservatives, and solubilizers.
  • auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.
  • Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.
  • Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.
  • Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.
  • Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.
  • Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures.
  • suitable skin-compatible solvents or solvent mixtures If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.
  • Emulsions can be administered orally, dermally or as injections.
  • Emulsions are either of the water-in-oil type or of the oil-in-water type. They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.
  • suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.
  • Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances,
  • Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.
  • Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.
  • the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.
  • suitable auxiliaries for this purpose are known in the art.
  • compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the present invention.
  • Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 per cent by weight, preferably from 0.1 to 65 per cent by weight, more preferably from 1 to 50 per cent by weight, most preferably from 5 to 40 per cent by weight.
  • Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90 per cent by weight, preferably of 1 to 50 per cent by weight.
  • Topical application may be conducted with compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.
  • solid formulations which release compounds of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.
  • the present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • compounds of formula (I) may be applied with other active ingredients (mixing partners). These additional ingredients may be used
  • compositions if appropriate also added only immediately prior to use (tank mix).
  • the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • M.1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1 A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xyly
  • GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
  • M.3 Sodium channel modulators from the class of M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpro
  • M.3B sodium channel modulators such as DDT or methoxychlor
  • nAChR Nicotinic acetylcholine receptor agonists
  • neonicotinoids for example acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M.4A.2: (2E-)-1-[(6-Chloropyridin- 3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin- 3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; or from the class M.4B nicotine;
  • M.6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin; M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues as hydroprene, kinoprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
  • M.8 miscellaneous non-specific (multi-site) inhibitors for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M.8E tartar emetic;
  • M.9 Selective homopteran feeding blockers for example M.9B pymetrozine, or M.9C flonicamid;
  • M.10 Mite growth inhibitors for example M.10A clofentezine, hexythiazox and diflovidazin, or M.10B etoxazole;
  • M.11 Microbial disruptors of insect midgut membranes for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israe/ensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • M.12 Inhibitors of mitochondrial ATP synthase for example M.12A diafenthiuron, or
  • M.12B organotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M.12D tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • benzoylureas as for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron or triflumuron;
  • M.16 Inhibitors of the chitin biosynthesis type 1 as for example buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
  • Octopamin receptor agonists as for example amitraz

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Abstract

La présente invention concerne des composés N-(thio)acylimino de formule (I) dont les variables sont telles que définies dans les revendications et la description, ainsi que leurs stéréoisomères, tautomères et sels. Des compositions à visée agricole ou vétérinaire comprenant lesdits composés, l'utilisation desdits composés pour lutter contre des invertébrés nuisibles, et des procédés de lutte contre les invertébrés nuisibles comprenant l'application desdits composés, sont en outre décrits.
PCT/EP2016/063316 2015-06-11 2016-06-10 Composés hétérocycliques n-(thio)acylimino Ceased WO2016198611A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

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