Pyrimidinone derivatives as pesticidal compounds

Abstract

The present invention relates to compounds of formula (I) G (I), wherein the variables are defined in the description. The invention also relates to pesticidal mixtures comprising the compounds of formula (I); the use of a compound of formula (I) as an agrochemical pesticidal agent; a method for combating or controlling invertebrate pests; a method for protecting growing plants from attack or infestation by invertebrate pests; seed comprising the compound of formula (I); the use of the compound of formula (I) for protecting growing plants from invasion or infestation by invertebrate pests; and methods for treating or protecting an animal from infestation or infection by invertebrate pests. I) # imgabs0 #

Description

[0001] The present invention relates to a compound of formula (I) or an agrochemically or veterinarily acceptable salt, stereoisomer, tautomer, or N-oxide thereof

[0002]

[0003] wherein these variables are as defined below. The present invention also relates to the use of a compound of formula (I) as an agrochemical pesticidal agent; to a pesticidal composition comprising a compound of formula (I) and another pesticidal ingredient; to a method for combating or controlling invertebrate pests, which method comprises bringing the pests or their food supply, habitat or breeding ground into contact with a pesticidally effective amount of at least one compound of formula (I) or a pesticidal mixture; to a method for protecting growing plants from infestation or infection by invertebrate pests, which method comprises bringing the plant, or the soil or water in which the plant is growing, into contact with a pesticidally effective amount of at least one compound of formula (I) or a pesticidal mixture; and to seeds comprising a compound of formula (I) or a pesticidal composition in an amount of from 0.1 g to 10 kg per 100 kg of seeds; to the use of a compound of formula (I) or a pesticidal composition for protecting growing plants from infestation or infection by invertebrate pests; and to a method for treating or protecting animals from infestation or infection by invertebrate pests, which method comprises bringing the animals into contact with a pesticidally effective amount of a compound of formula (I).

[0004] Invertebrate pests and especially insects, arachnids and nematodes damage growing and harvested crops and infest wooden dwellings and commercial buildings, causing significant economic losses to food supplies and property. There is therefore a continuing need for new agents for combating invertebrate pests.

[0005] WO 2017 / 167832 and WO 2018 / 206479 disclose bicyclic pyrimidinone compounds and their pesticidal activity. The present invention differs from these disclosures in that the residue R 1 is halogen.

[0006] WO 2021 / 204577 and WO 2022128524 disclose bicyclic pyrimidinone compounds and their pesticidal activity, wherein the residue R 1 is especially selected from halogen, and wherein R 7 is especially selected from “-C(CN)R 7 R 8 and C3-C6-cycloalkyl, which is substituted by CN and which does not have any further substituents, or which is further substituted by one or more identical or different substituents R 9"substituted". WO '77 does not disclose R 1 is halogen and R 7 in the specific combinations required herein.

[0007] Due to the ability of target pests to develop resistance to pesticidal active agents, there is a continuing need to identify additional compounds suitable for combating invertebrate pests such as insects, arachnids and nematodes. In addition, there is a need for new compounds having high pesticidal activity and showing a broad spectrum of activity against a large number of different invertebrate pests, especially against insects, arachnids and nematodes that are difficult to control. In addition, there is a need for compounds that are environmentally friendly and show favorable toxicological properties.

[0008] Accordingly, it is an object of the present invention to identify and provide compounds that exhibit high pesticidal activity, have a broad spectrum of activity against invertebrate pests and show environmentally and toxicologically favorable properties.

[0009] It has been found that these objects can be achieved by: substituted bicyclic compounds of formula (I) as described and defined below, including their stereoisomers, their salts (especially their agriculturally or veterinarily acceptable salts), their tautomers and their N-oxides.

[0010] In a first aspect, the present invention relates to a compound of formula (I),

[0011]

[0012] wherein,

[0013] rings A and B are fully unsaturated.

[0014] Y is C═X, where X is O;

[0015] E is N(R 3 );

[0016] Q is N, N(R 5 ) or CH;

[0017] G is phenyl or pyridyl;

[0018] W is S, S(O), S(O)2, S(O)(NR W ), S(O)(NH);

[0019] R 1 is halogen;

[0020] R 3 、R 5independently is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated;

[0021] each R 7 independently is H, halogen, OH, CN;

[0022] C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, these groups are unsubstituted or halogenated;

[0023] a 3- to 12-membered saturated, partially unsaturated or fully unsaturated heterocycle or ring system, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O, N, or S, and is unsubstituted or substituted by one or more R H substituted;

[0024] phenyl, which is unsubstituted or substituted by one or more R J substituted;

[0025] OR K ;

[0026] -C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0027] each R H independently is halogen, CN; C1-C3-alkyl, C1-C3-haloalkyl;

[0028] each R J independently is halogen, CN; C1-C6-alkyl, C1-C6-alkoxy, these groups are unsubstituted or halogenated; or in the case where two adjacent substituents R J are C1-C6-alkoxy, these substituents form an alkyl bridge between the two oxygens, which is unsubstituted or halogenated;

[0029] each R K is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, these groups are unsubstituted or substituted by one or more identical or different substituents selected from halogen, CN;

[0030] each R W independently is C1-C4-alkyl, or cyclopropyl;

[0031] if G is phenyl, then the subscript n is 1, 2, or 3, or 4, or if G is pyridyl, then the subscript n is 1, 2, or 3;

[0032] and its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

[0033] In another aspect, the present invention relates to a compound of formula (I),

[0034]

[0035] wherein,

[0036] rings A and B are completely unsaturated.

[0037] Y is C═X, where X is O;

[0038] E is N(R 3 );

[0039] Q is N, N(R 5 ), or CH;

[0040] G is phenyl or pyridyl;

[0041] W is S, S(O), S(O)2, S(O)(NR W );

[0042] R 1 is halogen;

[0043] R 3 , R 5 are independently C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated;

[0044] each R 7 is independently H, halogen, OH, CN;

[0045] C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, these groups are unsubstituted or halogenated;

[0046] a 3- to 12-membered saturated, partially unsaturated or completely unsaturated heterocycle or ring system, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O, N, or S, and is unsubstituted or substituted by one or more R H ;

[0047] phenyl, which is unsubstituted or substituted by one or more R J ;

[0048] OR K ;

[0049] -C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0050] Each R H independently is halogen, CN; C1-C3-alkyl, C1-C3-haloalkyl;

[0051] Each R J independently is halogen, CN; C1-C6-alkyl, C1-C6-alkoxy, these groups being unsubstituted or halogenated;

[0052] Each R K is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, these groups being unsubstituted or substituted by one or more identical or different substituents selected from halogen, CN;

[0053] Each R W independently is C1-C4-alkyl, cycloalkyl, or cyclopropyl;

[0054] If G is phenyl, the subscript n is 1, 2, or 3, or 4, or if G is pyridyl, the subscript n is 1, 2, or 3;

[0055] and its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

[0056] The compounds of formula (I) and their agriculturally acceptable salts are highly active against animal pests (i.e., harmful arthropods and nematodes), especially against insects and mites that are difficult to control by other means.

[0057] Furthermore, the present invention relates to and includes the following embodiments:

[0058] - Compositions that contain at least one compound of formula (I) as defined above and a liquid or solid carrier;

[0059] - Agricultural and veterinary compositions that contain an amount of at least one compound of formula (I) as defined above or its enantiomers, diastereomers or salts;

[0060] - A method for combating invertebrate pests, infested or infected by invertebrate pests, which method comprises bringing the pests or their food supply, habitat or breeding ground into contact with a pesticidal effective amount of at least one compound of formula (I) as defined above or its composition;

[0061] - A method for controlling invertebrate pests, or for treating or preventing infestation or infection by invertebrate pests, which method comprises contacting said pests or their food supply, habitat or breeding ground with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0062] - A method for preventing or protecting against invertebrate pests, which methods comprise contacting said invertebrate pests or their food supply, habitat or breeding ground with a substituted imidazolium compound of general formula (I) as defined above or a composition comprising at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0063] - A method for protecting crops, plants, plant propagation materials and / or growing plants against infestation or infection by invertebrate pests, which methods comprise contacting or treating said crops, plants, plant propagation materials and growing plants or the soil, material, surface, space, area or water body in which said crops, plants, plant propagation materials are stored or in which said plant grows with a pesticidally effective amount of at least one compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0064] - A non-therapeutic method for treating an animal infested or infected with a parasite or for preventing an animal from being infected or infested with a parasite or for protecting an animal against infestation or infection by a parasite, which method comprises orally, topically or parenterally administering or applying to the animal a parasitocidally effective amount of a compound of formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0065] - A method for treating, controlling, preventing or protecting an animal against infestation or infection by a parasite, which methods comprise orally, topically or parenterally administering or applying to the animal a compound of general formula (I) as defined above or a composition comprising at least one compound of formula (I);

[0066] - Seeds which comprise a compound of formula (I) as defined above in an amount of from 0.1 g to 10 kg per 100 kg of seeds;

[0067] - Use of a compound of formula (I) as defined above for protecting growing plants or plant propagation materials against infestation or infection by invertebrate pests;

[0068] - Use of a compound of formula (I) or an enantiomer, diastereomer or veterinarily acceptable salt thereof for combating parasites in and on animals;

[0069] - A method for preparing a veterinary composition for treating, preventing, protecting animals from parasite infestation or infection, the method comprising adding a parasitically effective amount of a compound of formula (I) or its enantiomers, diastereomers and / or veterinarily acceptable salts to a carrier composition suitable for veterinary use;

[0070] - Use of a compound of formula (I) or its enantiomers, diastereomers and / or veterinarily acceptable salts for the preparation of a medicament for treating, preventing, protecting animals from parasite infestation or infection.

[0071] All compounds of formula (I) and, where applicable, their stereoisomers, their tautomers, their salts or their N-oxides and their compositions are particularly useful for controlling invertebrate pests, especially for controlling arthropods and nematodes and especially insects. Accordingly, the present invention relates to the use of compounds of formula (I) as agrochemical pesticides, preferably for combating or controlling invertebrate pests, especially insects, arachnids or nematodes.

[0072] As used herein, the term "compound according to the invention" or "compound of formula (I)" means and includes the compounds as defined herein and / or their stereoisomers, salts, tautomers or N-oxides. The term "compounds of the invention" should be understood as being equivalent to the term "compounds according to the invention" and thus also includes the stereoisomers, salts, tautomers or N-oxides of the compounds of formula (I). As used herein, the term "compounds of the invention" or "compounds according to the invention" means the compounds of formula (I) as defined above, which are also referred to as "compounds of formula I" or "compound I" or "formula I compounds", and includes their salts, tautomers, stereoisomers, and N-oxides.

[0073] The term "composition according to the invention" or "composition of the invention" encompasses such compositions which comprise at least one compound of formula (I) according to the invention as defined above and thus also includes the stereoisomers, agriculturally or veterinarily acceptable salts, tautomers or N-oxides of the compounds of formula (I).

[0074] The compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) or may have modified forms with different macroscopic properties such as stability or may exhibit different biological properties such as activity. The present invention includes both amorphous and crystalline compounds of formula (I), mixtures of different crystalline states or modified forms of the corresponding compound I, and their amorphous or crystalline salts.

[0075] Compounds of formula (I) can have one or (depending on the substitution pattern) more chiral centers, in which case they exist as mixtures of enantiomers or diastereomers. The present invention provides the individual pure enantiomers or pure diastereomers of the compounds of formula (I) and mixtures thereof, as well as the use according to the invention of the pure enantiomers or pure diastereomers or mixtures thereof of the compounds of formula (I). Suitable compounds of formula (I) also include all possible geometric stereoisomers (cis / trans isomers) and mixtures thereof. Cis / trans isomers can exist with respect to olefins, carbon-nitrogen double bonds or amide groups. The term "stereoisomers" encompasses optical isomers, such as enantiomers or diastereomers (the latter existing due to more than one chiral center in the molecule), as well as geometric isomers (cis / trans isomers). The present invention relates to each possible stereoisomer of the compounds of formula (I), i.e., a single enantiomer or diastereomer, and mixtures thereof.

[0076] Depending on the substitution pattern, compounds of formula (I) can exist in the form of their tautomers. Accordingly, the present invention also relates to the tautomers of formula (I) and the stereoisomers, salts, tautomers and N-oxides of said tautomers.

[0077] Salts of the compounds of formula (I) are preferably agriculturally and / or veterinarily acceptable salts. They can be formed by conventional methods, for example, if the compound of formula (I) has a basic functional group, by reacting the compound with an acid of the anion in question, or by reacting an acidic compound of formula (I) with a suitable base.

[0078] Suitable agriculturally or veterinarily acceptable salts are especially those salts of cations or acid addition salts of those acids, the cations and anions of which respectively have no adverse effect on the action of the compounds according to the invention. Suitable cations are in particular alkali metal (preferably lithium, sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium and barium) ions and transition metal (preferably manganese, copper, zinc and iron) ions, and also ammonium (NH4 + ) and substituted ammonium, where 1 to 4 hydrogen atoms are replaced by C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl. Examples of substituted ammonium ions include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium. In addition, there are also phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.

[0079] The anions of the available acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting the compounds of formula I with acids of the corresponding anions, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0080] The term "N-oxide" includes any compound of the invention having at least one tertiary nitrogen atom oxidized to an N-oxide moiety.

[0081] The organic moiety groups mentioned in the above definitions of the variables - like the term halogen - are collective terms for a single listing of the individual group members. The prefix C x -C y indicates in each case the possible number of carbon atoms in the group. "Halogen" shall mean F, Cl, Br, and I, preferably F.

[0082] The terms "compounds of formula (x)" and "compound (x)" (where x is a Roman or Arabic numeral) are used interchangeably herein and refer to a single or several compounds as defined by the corresponding formula (x).

[0083] For example, the term "substituted by" as used in "substituted in part or completely by" means that one or more, for example 1, 2, 3, 4, or 5 or all of the hydrogen atoms of a given group are replaced by one or more identical or different substituents as defined subsequently. Thus, for a substituted cyclic moiety, for example 1-cyanocyclopropyl, one or more of the hydrogen atoms of the cyclic moiety can be replaced by one or more identical or different substituents.

[0084] The term "halogen" means fluorine, chlorine, bromine, iodine, preferably fluorine, chlorine, bromine. Unless otherwise specified, other groups can be substituted by halogen, i.e., halogenated, which is to be understood as being completely or partially substituted by one or more halogen atoms.

[0085] As used herein (and also in C x -C y -alkylamino, di-C x -C y -alkylamino, C x -C y -alkylaminocarbonyl, di-(C x -C y -alkylamino)carbonyl, C x -C y -alkylthio, C x -C y-alkylsulfinyl and C x -C y -alkylsulfonyl) the term "C x -C y -alkyl" refers to a branched or unbranched saturated hydrocarbon group having from n to m (e.g., from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms), such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, nonyl and decyl and their isomers. For example, C1-C4-alkyl means methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl.

[0086] As used herein (and also in C x -C y -haloalkylsulfinyl and C x -C y -haloalkylsulfonyl) the term "C x -C y -haloalkyl" refers to a straight-chain or branched alkyl group having from n to m carbon atoms (e.g., from 1 to 10, especially from 1 to 6 carbon atoms) as mentioned above, where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, such as C1-C4-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, etc. The term C1-C 10 -haloalkyl specifically includes C1-C2-fluoroalkyl, which is synonymous with methyl or ethyl, where 1, 2, 3, 4 or 5 hydrogen atoms are replaced by fluorine atoms, such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl and pentafluoromethyl.

[0087] Similarly, "C x -C y -alkoxy" and "C x -C y -alkylthio" (or, respectively, C x -C y -alkylsulfinyl) refers to a straight-chain or branched alkyl group having from n to m carbon atoms (e.g., from 1 to 10, especially from 1 to 6 or from 1 to 4 carbon atoms) bonded via an oxygen (or, respectively, a sulfur linkage) bond at any bond in the alkyl group (as mentioned above). Examples include C1-C4-alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy, and tert-butoxy, and also C1-C4-alkylthio groups such as methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

[0088] Thus, the terms "C x -C y -haloalkoxy" and "C x -C y -haloalkylthio" (or, respectively, C x -C y -haloalkylsulfinyl) each refer to a straight-chain or branched alkyl group having from n to m carbon atoms (e.g., from 1 to 10, especially from 1 to 6 or from 1 to 4 carbon atoms) bonded via an oxygen or sulfur linkage bond at any bond in the alkyl group (as mentioned above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above, e.g., C1-C2-haloalkoxy groups such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, and pentafluoroethoxy, and also C1-C2-haloalkylthio groups such as chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, and pentafluoroethylthio, etc. Similarly, the terms C1-C2-fluoroalkoxy and C1-C2-fluoroalkylthio each refer to a C1-C2-fluoroalkyl group bonded via an oxygen atom or a sulfur atom to the remainder of the molecule.

[0089] As used herein, the term "C2-C y -alkenyl" means a branched or unbranched unsaturated hydrocarbon group having 2 to m (e.g., 2 to 10 or 2 to 6 carbon atoms) and a double bond at any position, such as vinyl, 1-propenyl, 2-propenyl, 1-methyl-vinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.

[0090] As used herein, the term "C2-C y"-alkynyl" refers to a branched or unbranched unsaturated hydrocarbon group having 2 to m (e.g., 2 to 10 or 2 to 6 carbon atoms) and containing at least one triple bond, such as ethynyl, propynyl, 1-butynyl, 2-butynyl, etc.

[0091] As used herein, the term "C x -C y -alkoxy-C x -C y -alkyl" refers to an alkyl group having n to m carbon atoms, such as the specific examples mentioned above, wherein one hydrogen atom of the alkyl group is replaced by C x -C y -alkoxy; where the values of x and y of the alkoxy are independently selected from the values of the alkyl group.

[0092] Thus, as used herein, the term "C x -C y -alkoxy-C x -C y -alkoxy" refers to an alkoxy group having n to m carbon atoms, such as methoxy or ethoxy, wherein one hydrogen atom of the alkoxy group is replaced by C x -C y -alkoxy; where the values of x and y of the alkoxy are independently selected from the values of the alkoxy group.

[0093] The suffix "-carbonyl" or "C(=O)" in each group indicates that the group is bonded to the remainder of the molecule via the carbonyl C=O bond. For example, in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylcarbonylamino, and hydroxycarbonyl, it is exactly so. For example, hydroxycarbonyl refers to the carbonate group -C(=O)OH, and aminocarbonyl refers to the amide group -C(=O)NH2, both of which are bonded to the remainder of the molecule via the carbonyl "C=O" bond.

[0094] As used herein, the term "aryl" refers to a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon group, such as phenyl or naphthyl, especially phenyl (also known as C6H5 as a substituent).

[0095] As used herein, the term "C3-C y -cycloalkyl" refers to a monocyclic 3- to y-membered saturated alicyclic group, such as cyclopropyl (cC3H5), cyclobutyl (cC4H7), cyclopentyl (cC5H9), cyclohexyl (cC6H 11 )), cycloheptyl, cyclooctyl, and cyclodecyl.

[0096] Thus, as used herein, the term "C3-C y -cycloalkoxy" refers to "C3-C y”-cycloalkyl moiety, which is bonded to the remainder of the molecule via an oxygen atom, such as in cyclopropoxy, cyclobutoxy, cyclopentyloxy, and cyclohexyloxy.

[0097] The term "C3-C y -cycloalkoxy-C x -C y -alkyl" refers to a C x -C y -alkyl moiety in which one hydrogen atom is replaced by a C3-C y -alkoxy, and wherein the subscripts x and y are independently selected according to the indicated meanings.

[0098] The term "cycloalkylalkyl" and the term "alkyl which may be substituted by cycloalkyl" denote an alkyl which is substituted by a cycloalkyl ring, wherein the alkyl and the cycloalkyl are as defined herein.

[0099] As used herein, the term "C3-C y -cycloalkenyl" refers to a monocyclic 3- to y-membered partially unsaturated alicyclic group.

[0100] The term "cycloalkylcycloalkyl" and the term "cycloalkyl which may be substituted by cycloalkyl" denote a cycloalkyl substituted on another cycloalkyl ring, wherein each cycloalkyl ring independently has 3 to 7 carbon atom ring members, and these cycloalkyls are linked by a single bond or have a common carbon atom. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (e.g., 1,1'-bicyclopropyl-2-yl); cyclohexylcyclohexyl, wherein the two rings are linked by a single common carbon atom (e.g., 1,1'-bicyclohexyl-2-yl); cyclohexylcyclopentyl, wherein the two rings are linked by a single bond (e.g., 4-cyclopentylcyclohexyl) and its different stereoisomers, such as (1R,2S)-1,1'-bicyclopropyl-2-yl and (1R,2R)-1,1'-bicyclopropyl-2-yl. Unless otherwise specified, the term "carbocyclic" or "carbocyclic group" generally includes 3- to 12-membered, preferably 3- to 8-membered or 5- to 8-membered, more preferably 5- or 6-membered monocyclic rings containing 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms.

[0101] The carbocyclic group may be saturated, partially unsaturated, or fully unsaturated. Preferably, the term "carbocyclic" encompasses cycloalkyl and cycloalkenyl as defined above, such as cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings. When referring to a "fully unsaturated" carbocyclic ring, the term also includes an "aromatic" carbocyclic ring. In certain preferred embodiments, the fully unsaturated carbocyclic ring is an aromatic carbocyclic ring as defined below, preferably a 6-membered aromatic carbocyclic ring.

[0102] The term "heteroaryl" or "aromatic heterocycle" or "aromatic heterocyclic ring" includes monocyclic 5- or 6-membered heteroaromatic groups containing 1, 2, 3, or 4 heteroatoms selected from N, O, and S as ring members. Examples of 5- or 6-membered heteroaromatic groups include pyridyl, i.e., 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e., 2-, 4-, or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e., 3- or 4-pyridazinyl, thienyl, i.e., 2- or 3-thienyl, furyl, i.e., 2- or 3-furyl, pyrrolyl, i.e., 2- or 3-pyrrolyl, oxazolyl, i.e., 2-, 3-, or 5-oxazolyl, isoxazolyl, i.e., 3-, 4-, or 5-isoxazolyl, thiazolyl, i.e., 2-, 3-, or 5-thiazolyl, isothiazolyl, i.e., 3-, 4-, or 5-isothiazolyl, pyrazolyl, i.e., 1-, 3-, 4-, or 5-pyrazolyl, i.e., 1-, 2-, 4-, or 5-imidazolyl, oxadiazolyl, such as 2- or 5-[1,3,4]oxadiazolyl, 4- or 5-(1,2,3-oxadiazolyl), 3- or 5-(1,2,4-oxadiazolyl), 2- or 5-(1,3,4-thiadiazolyl), thiadiazolyl, such as 2- or 5-(1,3,4-thiadiazolyl), 4- or 5-(1,2,3-thiadiazolyl), 3- or 5-(1,2,4-thiadiazolyl), triazolyl, such as 1H-, 2H-, or 3H-1,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or 4H-1,2,4-triazolyl, and tetrazolyl, i.e., 1H- or 2H-tetrazolyl.

[0103] Unless otherwise specified, "heterocycle", "heterocyclic group" or "heterocyclic ring" generally includes monocyclic heterocyclic groups having 3 to 12 members, preferably 3 to 8 members, 3 to 7 members, or 5 to 8 members, more preferably 5 or 6 members, especially 6-membered. The heterocyclic group can be saturated, partially unsaturated, or fully unsaturated. As used in this context, the term "fully unsaturated" also includes "aromatic". In a preferred embodiment, the fully unsaturated heterocycle is thus an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle containing one or more (e.g., 1, 2, 3, or 4, preferably 1, 2, or 3) heteroatoms selected from N, O, and S as ring members. Examples of aromatic heterocycles are provided above in connection with the definition of "heteroaryl". Unless otherwise specified, "heteroaryl" is thus encompassed by the term "heterocycle". Heterocyclic non-aromatic groups generally contain 1, 2, 3, 4, or 5, preferably 1, 2, or 3 heteroatoms selected from N, O, and S as ring members, where the S-atom as a ring member can be present as S, SO, or SO2, and the N-atom can be oxidized or unoxidized. Examples of 5- or 6-membered heterocyclic groups include saturated or unsaturated non-aromatic heterocycles such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxide (S-oxothietanyl), thietanyl-S-dioxide (S-dioxothietanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S-oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl, etc. Examples of heterocycles containing 1 or 2 carbonyls as ring members include pyrrolidin-2-one, pyrrolidine-2,5-dione, imidazolidin-2-one, oxazolidin-2-one, thiazolidin-2-one, etc.

[0104] The terms "alkylene", "alkenylene", and "alkynylene" respectively refer to alkyl, alkenyl, and alkynyl groups as defined above, which are bonded to the remainder of the molecule via two atoms of the corresponding group, preferably via two carbon atoms of the corresponding group, and thus they represent a linker between two parts of the molecule. In particular, the term "alkylene" may refer to an alkyl chain such as CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2. Similarly, "alkenylene" and "alkynylene" may refer to alkenyl and alkynyl chains respectively.

[0105] As used herein, the term "5- to 6-membered carbocyclic ring" refers to cyclopentane and cyclohexane rings.

[0106] Examples of 5- or 6-membered saturated heterocycles include: 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl.

[0107] Examples of 5- or 6-membered partially unsaturated heterocyclic groups or heterocycles include: 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-dihydro- or tetrahydropyridyl, 3-dihydro- or tetrahydropyridazinyl, 4-dihydro- or tetrahydropyridazinyl, 2-dihydro- or tetrahydropyrimidinyl, 4-dihydro- or tetrahydropyrimidinyl, 5-dihydro- or tetrahydropyrimidinyl, dihydro- or tetrahydropyrazinyl, 1,3,5-dihydro- or tetrahydrotriazin-2-yl.

[0108] Examples of 5- or 6-membered fully unsaturated heterocycles (heteroaryl) or heteroaromatic rings are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

[0109] “C2-C y -alkylene” is a divalent branched or preferably unbranched saturated aliphatic chain having from 2 to m, for example from 2 to 7 carbon atoms, such as CH2CH2, -CH(CH3)-, CH2CH2CH2, CH(CH3)CH2, CH2CH(CH3), CH2CH2CH2CH2, CH2CH2CH2CH2CH2, CH2CH2CH2CH2CH2CH2, and CH2CH2CH2CH2CH2CH2CH2.

[0110] As used herein, the term "alkylamino" refers to a straight-chain or branched-chain saturated alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms, which is bonded via a nitrogen atom (such as an -NH- group).

[0111] As used herein, the term "dialkylamino" refers to a straight-chain or branched-chain saturated alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms, which is bonded via a nitrogen atom that is substituted by another straight-chain or branched-chain saturated alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms, such as methylamino or ethylamino.

[0112] As used herein, the term "alkylthio" (alkylthioalkyl: alkyl-S-) refers to a straight-chain or branched-chain saturated alkyl group having from 1 to 10 carbon atoms, preferably from 1 to 4 carbon atoms (= C1-C4-alkylthio), more preferably from 1 to 3 carbon atoms, which is attached via a sulfur atom. Examples include methylthio, ethylthio, propylthio, isopropylthio, and n-butylthio.

[0113] As used herein, the term "haloalkylthio" refers to an alkylthio as mentioned above, in which a hydrogen atom is partially or completely substituted by fluorine, chlorine, bromine, and / or iodine. Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, and pentafluoroethylthio, among others.

[0114] As used herein, the term "alkylsulfinyl" (alkylsulfinyl: C1-C6-alkyl-S(=O)-) refers to a straight-chain or branched-chain saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms, bonded via the sulfur atom of the sulfinyl group at any position in the alkyl group (as mentioned above).

[0115] As used herein, the term "(halo)alkylsulfonyl" (alkyl-S(=O)2-) refers to a straight-chain or branched-chain saturated (and halo)alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-(halo)alkylsulfonyl), preferably 1 to 3 carbon atoms, bonded via the sulfur atom of the sulfonyl group at any position in the (halo)alkyl group.

[0116] As used herein, the term "(halo)alkylthio" (alkyl-S-) refers to a straight-chain or branched-chain saturated (and halo)alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-(halo)alkylthio), preferably 1 to 3 carbon atoms, bonded via the sulfur atom of the alkylthio group at any position in the (halo)alkyl group.

[0117] As used herein, the term "(halo)alkylsulfinyl" (alkyl-S(=O)-) refers to a straight-chain or branched-chain saturated (and halo)alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (=C1-C4-(halo)alkylsulfinyl), preferably 1 to 3 carbon atoms, bonded via the sulfur atom of the sulfinyl group at any position in the (halo)alkyl group.

[0118] Thus, the terms (halo)alkylthioalkyl, (halo)alkylsulfinylalkyl, and (halo)sulfonylalkyl as used, for example, in "C1-C4-alkylthio-C1-C4-alkyl", "C1-C4-alkylsulfinyl-C1-C4-alkyl", and "C1-C4-alkylsulfonyl-C1-C4-alkyl" refer to (halo)alkylthio-, (halo)alkylsulfinyl-, or (halo)alkylsulfonyl- bonded via the sulfur atom of the alkylthio, sulfinyl, or sulfonyl group, respectively, to an alkyl group which is in turn bonded to the remainder of the molecule.

[0119] The term "alkylcarbonyl" (C1-C6-C(=O)-) refers to a straight-chain or branched-chain alkyl group as defined above, bonded to the remainder of the molecule via the carbon atom of the carbonyl group (C=O).

[0120] The term "alkoxycarbonyl" refers to an alkoxy group as defined above, bonded to the remainder of the molecule via the carbon atom of the carbonyl group (C=O).

[0121] The term "alkylaminocarbonyl" (C1-C6-NH-C(=O)-) refers to a straight-chain or branched-chain alkylamino as defined above, which is bonded to the remainder of the molecule via the carbon atom of the carbonyl group (C=O). Similarly, the term "dialkylaminocarbonyl" refers to a straight-chain or branched-chain saturated alkyl as defined above, which is bonded to a nitrogen atom that is substituted by another straight-chain or branched-chain saturated alkyl as defined above, and the nitrogen atom is in turn bonded to the remainder of the molecule via the carbonyl group (C=O).

[0122] The term "S(O)(NR W )" refers to the group

[0123]

[0124] wherein R W is as defined for formula (I), and wherein the symbols "&" and "§" denote attachment to the remainder of the molecule. Thus, the group R W -W attached to the ring "G" can have the meaning R W -S(O)(NR W ), which refers to the group

[0125]

[0126] where each R W is independently as defined for formula (I), and wherein the symbol "§" denotes attachment to the remainder of the molecule (i.e., the ring "G").

[0127] The compounds of formula (I) can be prepared by standard methods of organic chemistry. If certain derivatives cannot be prepared by the methods outlined below, they can be obtained by derivatization of other compounds of formula (I) obtainable by these methods.

[0128] Methods for preparing the compounds of formula (I) that are generally applicable have been disclosed in WO 2017 / 167832, especially on pages 4-6 and in the experimental section; WO 2021 / 204577, especially on pages 15-26 and in the experimental section; WO 2021 / 099240 and WO 2022128524. In the methods and schemes depicted below, unless otherwise described, the variables of the formula have the meanings as defined for formula (I). The variable "LG" refers to a leaving group such as Cl, Br, I, trifluoromethanesulfonate, tosylate, etc. The variables R 71 and R 72 each independently have the meanings as defined for R 7 in formula (I)--unless otherwise specified. The variable A is N or CH.

[0129] Compounds of formula (II) corresponding to the compounds of formula (I) where Q is CH can be prepared by the reaction of a compound of formula (III) with a compound of formula (IV), as shown in Method 1.

[0130] Method 1:

[0131]

[0132] All variables in formulas (III), (IV) and (II) have the meanings as defined for formula (I). This type of reaction has been described in EP 3257853 A1 and WO 2018206479. The reaction is typically carried out at a high temperature of 50 °C - 160 °C in an inert solvent. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C 10 - hydrocarbons such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3 (MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetrahydrofuran (THF), and diethylene glycol; nitriles such as CH3CN, and CH3CH2CN; alcohols such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), CH3CH(OH)CH2OH; amide and urea derivatives such as dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), dimethylacetamide (DMA), 1,3-dimethyl-2-imidazolidinone (DMI), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), hexamethylphosphoramide (HMPA); in addition, dimethyl sulfoxide (DMSO), sulfolane, and water. Mixtures of the above solvents are also possible.

[0133] This reaction can be carried out in the presence of a catalyst (such as an acid or a base, preferably a base). Suitable bases are usually inorganic bases such as LiOH, NaOH, KOH, and Ca(OH)₂; alkali metal and alkaline earth metal oxides such as Li₂O, Na₂O, CaO, and MgO; alkali metal and alkaline earth metal hydrides such as LiH, NaH, KH, and CaH₂; alkali metal and alkaline earth metal carbonates such as Li₂CO₃, K₂CO₃, and CaCO₃; alkali metal bicarbonates such as NaHCO₃; organic bases such as pyrrolidine; tertiary amines such as diisopropylethylamine, trimethylamine, triethylamine, triisopropylamine, and N-methylpiperidine, imidazole, pyridine; substituted pyridines such as collidine, lutidine, and 4-dimethylaminopyridine, and polycyclic amides and amidines such as 1,8-diazabicycloundec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO); alkali metal salts of secondary amines such as alkali metal diisopropylamides, alkali metal bis(trimethylsilyl)amides, alkali metal tetramethylpiperidines; alkoxides such as alkali metal methoxides, alkali metal ethoxides, alkali metal isopropoxides, alkali metal tert-butoxides; alkali metal-alkyl and alkali metal-aryl salts such as n-butyllithium, tert-butyllithium, phenyllithium. Mixtures of the above bases are also possible. The bases are usually used in catalytic amounts; however, they can also be used in equimolar amounts, in excess, or (if appropriate) as solvents. The compounds of formula (III) and the compounds of formula (IV) typically react with each other in equimolar amounts. In terms of yield, it may be advantageous to use an excess of the compound of formula (IV).

[0134] Compounds of formula (IVa) that fall under the definition of formula (IV) where n is 1, W is S(O)₂ and R 7 in the para position can be prepared, for example, as described in Scheme 1.

[0135]

[0136] The variable A in Scheme 1 is N or CH, and R 71 and R 72 independently fall under the definition of R 7 as defined.

[0137] Scheme 1:

[0138]

[0139] Compound VI can be obtained by reacting a nitro group (which can also be any other suitable leaving group such as Cl, Br, I, F, -OTf, -OTs (tosylate), etc.) with HS-R in the presence of a base (such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, etc.) in a solvent like DMF, THF, and DMSO while cooling to ambient temperature WCompound V is treated by a substitution reaction, where X is Cl, Br, I, -OTf (trifluoromethanesulfonate), or a leaving group. This method has been similarly described in the literature such as Tetrahedron Letters, 2014, Vol. 55, No. 22, pp. 3295 - 3298.

[0140] Compound VII can be prepared by converting the cyano group to a keto group by reacting compound VI with the corresponding Grignard reagent. For this purpose, the nitrile compound (VI) can be dissolved in a suitable solvent such as THF, MTBE or toluene at 0 °C, then treated with CH3MgBr, CH3MgCl and stirred at 20 °C to 25 °C, as described in WO 2018095795, WO 2016012395 and Tetrahedron Letters 1981, Vol. 22, 3815 - 3818.

[0141] Compound VII can be further oxidized to SO2 (sulfone) by an oxidation reaction that involves reagents such as m-chloroperoxybenzoic acid, hydrogen peroxide, potassium peroxymonosulfate formulation, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite and solvents used for the oxidation include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. The amount of the oxidizing agent used for this reaction is usually 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compound VII that forms the sulfoxide compound, and preferably 2 to 2.2 moles of the oxidizing agent relative to 1 mole of the sulfide compound VII, as described in WO 2015 / 091945 A1, WO 2016107742 and WO 2018095795.

[0142] Compound X can be prepared by reacting compound VIII (where X is a leaving group such as chlorine, bromine or iodine (preferably bromine) or an aryl-, alkyl- or haloalkyl sulfonate such as trifluoromethanesulfonate) with the reagent R 71 -B(OH)2, R 71 -B(OR)2 (where R can be an alkyl, aryl, cycloalkyl or pinacol-type cyclic group of formula IX).

[0143] This reaction can be catalyzed preferably under an inert atmosphere in a solvent or solvent mixture, such as dioxane, 1,2-dimethoxyethane or toluene, in the presence of a base, such as sodium carbonate, potassium carbonate or cesium carbonate, or sodium tert-butoxide or potassium tert-butoxide, by a palladium-based catalyst, such as bis(diphenylphosphino)ferrocene]dichloropalladium(II)(1:1)(Pd(dppf)Cl2).DCM complex, tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0)(Pd(dba)2), tris(dibenzylideneacetone)dipalladium(0)(Pd2(dba)3; optionally in the form of its chloroform adduct), or palladium(II) acetate, and a ligand, such as XantPhos((5-diphenylphosphino-9,9-dimethyl-xanthen-4-yl)diphenylphosphine), RuPhos(2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl), JohnPhos([1,1-biphenyl]-2-ylbis(1,1-dimethylethyl)phosphine), BINAP(2,2'-bis(diphenylphosphino)-1,1'-binaphthalene), tol-BINAP([2,2'-bis(di-p-tolyl-phosphino)-1,1'-binaphthalene]) or tris(o-tolyl)phosphine. The reaction temperature can preferably be in the range from room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such reactions have been described, for example, in Molecules 2012, 17, 4508-4521; Advanced Synthesis & Catalysis (2015), 357(2-3), 361-365; WO 2022025242 A1; Org. Lett., 2001, 3, 2757-2759; or Synlett, 2009, 1761-1764.

[0144] The reaction temperature can preferably be in the range from 20 °C to 25 °C to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such reactions have been described, for example, in Advanced Synthesis & Catalysis, 350(3), 391-394; 2008. Compound IVa can be prepared by dissolving compound X in a possible solvent used and a possible reagent used at ambient temperature or when heated to 60 °C during monitoring to obtain bromoketone IV. These solvents are ethyl acetate, chloroform or DCM, and these reagents are copper(II) bromide CuBr2, Br2, HBr in acetic acid, trimethylphenylammonium tribromide. This procedure can be seen in WO 2016107742.

[0145] Compounds of Formulas IX and XII are commercially available known compounds or can be prepared by known methods described in the literature, for example, Green Chemistry (2009), 11(10), 1610 - 1617; Angewandte Chemie, International Edition (2010), 49(10), 1846 - 1849; Organic Letters (2011), 13(13), 3312 - 3315; WO 2011149950 A2, etc.

[0146] Method 2:

[0147]

[0148] Alternatively, the compounds of formula (II) falling under the definition of formula (I) can be prepared by reacting a compound of formula (III) with a compound of formula (XI) to produce formula (XIII) as shown in Method 2. The condensation reaction can be carried out as described above to produce compound (II). Compound (XIII) can be further subjected to a Suzuki, Negishi or Sonogashira type C - C coupling reaction with R 71 -B(OH)2, R 71 -B(OR)2 as described above for the synthesis of intermediate (X) in Method 1.

[0149] Compounds of formula (XVII) corresponding to the compounds of formula (I) where Q is NR 5 can be prepared as shown in Method 3 below.

[0150] Method 3:

[0151]

[0152] This type of reaction has been described in EP 3257853 A1, WO 2019 / 234160 and WO 2016162318 A1. The reaction is typically carried out at a high temperature (e.g., 60 °C to 160 °C) in an inert solvent, optionally in the presence of an acid or a coupling agent and a base. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, o - xylene, m - xylene and p - xylene; halogenated hydrocarbons, or halogenated aromatic C6 - C 10- Hydrocarbons such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3 (MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetrahydrofuran (THF), and diethylene glycol; nitriles such as CH3CN and CH3CH2CN; alcohols such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH. Mixtures of the above solvents are also possible.

[0153] Suitable acids are generally inorganic acids such as HF, HCl, HBr, H2SO4, and HClO4; Lewis acids such as BF3, AlCl3, FeCl3, SnCl4, TiCl4, and ZnCl2, and in addition organic acids such as HCOOH, CH3COOH, CH3CH2COOH, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, and CF3COOH.

[0154] Suitable coupling agents are selected from carbodiimides such as DCC (dicyclohexylcarbodiimide) and DIC (diisopropylcarbodiimide), benzotriazole derivatives such as HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), HBTU ((O-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate), and HCTU (1H-benzotriazolium-1-[bis(dimethylamino)methylene]-5-chlorotetrafluoroborate), and phosphonium-derived activators such as BOP ((benzotriazol-1-yloxy)-tris(dimethylamino)phosphonium hexafluorophosphate), PyBOP ((benzotriazol-1-yloxy)-tripyrrolidinophosphonium hexafluorophosphate), and PyBrOP (bromotripyrrolidinophosphonium hexafluorophosphate). Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or petroleum ether; aromatic hydrocarbons such as benzene, toluene, o-xylene, m-xylene, and p-xylene; halogenated hydrocarbons, or halogenated aromatic C6-C 10- Hydrocarbons such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3 (MTBE), CH3OCH3 (DME), CH3OCH2CH2OCH3, CH3OC(CH3)2CH2CH3, dioxane, anisole, 2-methyltetrahydrofuran, tetrahydrofuran (THF), and diethylene glycol; nitriles such as CH3CN and CH3CH2CN; alcohols such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, and C(CH3)3OH, CH2(OH)CH2(OH), and CH3CH(OH)CH2OH. Mixtures of the above solvents are also possible. In the presence of a suitable base, to produce the compound of formula XXII, these bases being those listed above for Method 1. Subsequently, the condensation described in Method 1 is carried out to produce the compound of formula XVI.

[0155] Alternatively, the compound of formula (XV) can be replaced by its corresponding acid halide (e.g., acyl chloride). In this case, the reaction is typically carried out in the presence of a base. Suitable bases are those listed above for Method 1.

[0156] The compound of formula (XIV) and the compound of formula (XV) typically react with each other in equimolar amounts. In terms of yield, it may be advantageous to use an excess of the compound of formula (XV).

[0157] The compound of formula (XV) can be prepared as described in WO 2019 / 234160 A1. The compound of formula (XIV) can be prepared as described in WO 2017 / 167832 A1, Example C-4 or Bashandy et al. Journal of Enzyme Inhibition and Medicinal Chemistry, 29(5), 619 - 627, 2014.

[0158] Method 4a:

[0159]

[0160] Thus, the compound of formula (XV) can be prepared, for example, as follows. Compound VI can be oxidized to SO2 (sulfone) by an oxidation reaction involving reagents such as m-chloroperoxybenzoic acid, hydrogen peroxide, potassium peroxymonosulfate formulation, sodium periodate, sodium hypochlorite or tert-butyl hypochlorite and solvents used for the oxidation include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water. The amount of the oxidizing agent used in this reaction is generally 1 to 3 moles, preferably 1 to 1.2 moles, relative to 1 mole of the sulfide compound VI that forms the sulfoxide compound, and preferably 2 to 2.2 moles of the oxidizing agent relative to 1 mole of the sulfide compound VI, as described in WO 2015 / 091945A1, WO 2016107742 and WO 2018095795. By heating (XVIII) in a concentrated acid such as concentrated hydrochloric acid HCl or concentrated sulfuric acid H2SO4, preferably in the presence of water, optionally in the presence of an inert solvent such as acetic acid or an ether (e.g., tetrahydrofuran, ethylene glycol dimethyl ether or 1,4-dioxane), the compound of formula (XVIII) as defined in formula I and wherein X is a leaving group, especially those compounds wherein X is a halogen (even more preferably chlorine, bromine or iodine), is hydrolyzed to give XIX. Such hydrolysis conditions and their variants are known to those skilled in the art. Suzuki coupling (as described for the synthesis of compound II or X) can be used to produce compound XV, which has the meaning as defined for formula (I), by reacting it with compound XIV to produce (XVII) by a direct condensation reaction or via an intermediate XVI by an amide formation reaction followed by a condensation reaction.

[0161] The compound of formula (XXI) can be prepared by the reaction of a compound of formula (XIV) with a compound of formula (XIX), as shown in Method 5.

[0162] Method 5:

[0163]

[0164] The amide formation reaction yields a compound of formula (XX), followed by condensation to yield a compound of formula XXI, and / or the direct reaction of compound XIV with XIX to produce XXI can be carried out as discussed in Method 4.

[0165] Method 5a:

[0166]

[0167] The compound of formula (XXII) falling under the definition of formula (I) can be prepared by reacting a compound of formula (XXI) with a compound of formula (IX or XII) under a Suzuki-type coupling reaction as described for the production of compound XXI or II under Method 1.

[0168] Method 6:

[0169]

[0170] The compound of formula (XV) can be prepared as follows (Method 6): Under conditions known to those skilled in the art, for example, under acidic conditions, by refluxing in ethanol, methanol or other alcohol solvents, or under basic conditions using potassium carbonate, cesium carbonate, sodium carbonate, sodium hydroxide, potassium hydroxide and by adding an electrophilic reagent containing the corresponding alkyl halide Rd-X to esterify the compound of formula (XIX) to produce compound XXII, where Rd is a C1-C6-alkyl. Then, compound XXII is converted to compound XXIII by a Suzuki-type C-C coupling with boric acid XII or borate ester IX (as described in Method 1) to produce compound (XXIII). Subsequently, compound XXIII is converted to compound XIV by saponification of compound XXIII under conditions known to those skilled in the art (using, for example, the following conditions, such as an aqueous solution of sodium hydroxide, potassium hydroxide or lithium hydroxide in methanol, ethanol or dioxane at room temperature or up to reflux conditions) to provide the compound of formula (XV) as defined in formula I.

[0171] The compound of formula (XXIV) can be converted to compound XXV by rearrangement as shown below, where # represents the connection to residue G as defined in formula (I).

[0172] Method 7:

[0173]

[0174] This type of reaction has been described in Potts K.T., Surapaneni C.R., 1970, Journal of Heterocyclic Chemistry or Nagamatsu T., Fujita T., 2002, Heterocycles, 57(4), 631-636. The reaction is typically carried out in the presence of a catalyst, usually an acid or a base, such as NaOH or formic acid, in an inert organic solvent or water, at a temperature of 0 °C to 80 °C. If no catalyst is used, the reaction can be carried out at an elevated temperature, for example, 30 °C to 100 °C.

[0175] The compound of formula (XXIV) can be prepared by the reaction of a hydrazine compound of formula (XXVI) as shown in Method 8 below, where # represents the connection to residue G as defined in formula (I).

[0176] Method 8:

[0177]

[0178] This type of reaction has been described by Glushkov V.A. et al., 1998, Pharmaceutical Chemistry Journal, Vol. 32(5), pp. 29 - 32, or WO 2012148808, p. 143. This reaction is typically carried out in an inert organic solvent in the presence of a Lewis acid such as FeCl3 or AlCl3 at a high temperature of 50 °C to 150 °C. This reaction can be carried out in the presence of an oxidizing agent, such as H2O2 or CuCl2.

[0179] The compound of formula (XXVI) can be obtained by the reaction of a hydrazine compound of formula (XXVII) with an aldehyde compound of formula (XXVIII), as shown in Method 9 below.

[0180] Method 9:

[0181]

[0182] # represents the connection to the residue G as defined in formula (I).

[0183] This reaction is typically carried out in an inert organic solvent in the presence of an acid catalyst such as toluenesulfonic acid. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, or petroleum ether; or aromatic hydrocarbons such as benzene, toluene, o - xylene, m - xylene, and p - xylene. Mixtures of the above solvents are also possible.

[0184] The hydrazine derivatives of formula (XXVII) are commercially available or can be derived from commercially available compounds. Alternatively, the compounds of formula (XXVII) can also be prepared by the reaction of hydrazine with compounds of formula (XXIX), as shown in Method 10 below.

[0185] Method 10:

[0186]

[0187] where LG is a leaving group and all other variables have the meanings as defined for formula (I). Typical leaving groups are trifluoromethanesulfonate, iodine, and chlorine. This type of reaction has been described in Mao, Y. et al., 2014, Journal of Heterocyclic Chemistry, 51(3), pp. 594 - 597. This reaction is typically carried out in a polar solvent such as CH3CH2OH at a high temperature of 50 °C to 100 °C. The compounds of formula (XXXV) are commercially available or can be prepared by standard methods of organic chemistry.

[0188] Similarly, compound IIa falling under the definition of formula II can be prepared as shown in Method 11 below.

[0189] Method 11:

[0190]

[0191] The compound of formula (XXX) is commercially available or can be prepared by standard methods of organic chemistry. The compound XXX is condensed with aldehyde XXXI by a method similar to that described in Wade et al., US 4503050, May 05, 1985, to produce compound XXXII. The R (Cl, -OMe) present in compound XXXII is hydrolyzed under conditions known in the literature to produce compound XXVI. Compound XXVI can be prepared from XXXIII by an N-alkylation reaction under basic conditions or copper-catalyzed conditions, as described in Bioorganic & Medicinal Chemistry Letters, 25(6), 1310 - 1317; 2015. The rearrangement of XXIV is carried out as described in Method 7 to give compound IIa.

[0192] Alternatively, compound IIa can be obtained as shown in Scheme 2 below.

[0193] Scheme 2

[0194]

[0195] Compound XXXVII (where PG represents a protecting group) can be obtained by the reaction of commercially available compound XXXIV with compound XXV in an inert solvent such as DCM, THF, DMF or dioxane and in the presence of a base such as triethylamine (TEA) at 20 °C to 100 °C, as described in European Journal of Medicinal Chemistry (1990), 25(8), 653 - 8.

[0196] Compound XXXVIII can be obtained by reacting compound XXXVII with cyanoacetic acid in the presence of acetic anhydride, followed by reacting it under basic aqueous solution conditions (such as aqueous NaOH, aqueous KOH, aqueous Na2CO3, aqueous K2CO3, etc.), as described in CN 112125903 A and CN 111170951.

[0197] The protecting group is removed from intermediate XXXVIII under basic conditions (aqueous NaOH, aqueous KOH, aqueous Na2CO3, aqueous K2CO3), acidic conditions (aqueous HCl, aqueous H2SO4, AcOH) or under hydrogenation conditions in the presence of H2 and a metal catalyst such as Rh, Pd, Pt or by using a transfer hydrogenation reaction utilizing ammonium formate, potassium formate or sodium formate, resulting in the formation of compound XXXIX.

[0198] Compound XL can be prepared from compound XXXIX by reacting with POX3 (e.g., POCl3, POBr3) in the presence of a polar aprotic solvent such as THF, dioxane, DEE, etc., as described in Tetrahedron Letters (2003), 44(13), 2717 - 2720. Further condensation of compound XL with compound IV or XI using the method described in Method 1 produces compound XLI. Further Suzuki coupling reaction of XLI with IX or XII under the standard Suzuki-type conditions described in Method 1 produces compound XLII and / or IIa.

[0199] Alternatively, compound XXXIX can be condensed with intermediate IV or XI using the method described in Method I to obtain intermediate XLIII. Then the hydroxyl group can be converted to R by using methods known to those skilled in the art 1 (where X is a leaving group such as Cl, Br, -OTf, -Onf, tosyl, mesyl, etc.) to prepare compound XLIV. Further Suzuki coupling of XLIV with IX or XII can produce compound IIa and / or compound XLII.

[0200] Compounds of formula (XLV) falling under the definition of formula (I) (where R 71 is the group -C(CN)(CH3)2 or 1 - cyanocyclopropyl) can be prepared, for example, from compound XLVI by condensing it with compound XLVII (synthesized as described in WO 2021204577) according to the procedure described in Method 1 and as shown in Method 13 below:

[0201] Method 13:

[0202]

[0203] # represents the connection to the residue G as defined in formula (I).

[0204] The reaction mixture is worked up in a conventional manner, for example by mixing with water, phase separation and, if appropriate, chromatographic purification of the crude product. Some of the intermediates and end products are obtained in the form of a colorless or light brown viscous oil, which is purified or the volatile constituents are removed under reduced pressure and at a moderate elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0205] The N-oxides can be prepared from the compounds of the invention according to conventional oxidation methods, for example by treatment of the compound I with an organic peracid such as m-chloroperbenzoic acid (see WO 03 / 64572 or J. Med. Chem. [Journal of Medicinal Chemistry] 38(11), 1892 - 903, 1995); or with an inorganic oxidant such as hydrogen peroxide (see J. Heterocyc. Chem. [Journal of Heterocyclic Chemistry] 18(7), 1305 - 8, 1981) or potassium peroxymonosulfate preparation (see J. Am. Chem. Soc. [Journal of the American Chemical Society] 123(25), 5962 - 5973, 2001). The oxidation can give pure mono-N-oxides or mixtures of different N-oxides, which can be separated by conventional methods such as chromatography.

[0206] If a mixture of isomers is obtained on synthesis, separation is generally not necessarily required, since in some cases the individual isomers may interconvert during the work-up for use or during application (e.g. under the action of light, acids or bases). Such conversions can also occur after use, for example in the treated plants in the case of plant treatment or in the harmful fungi to be combated.

[0207] Those skilled in the art will readily understand that the preferred options for the variables defined herein in connection with compound I, and in particular the preferred options given in the following table for the corresponding substituents, apply accordingly to the intermediates (compounds II to XLVII). Thus, the substituents in each case independently of one another or more preferably in combination have the meanings as defined herein.

[0208] These variables each individually and in combination have the following preferred meanings.

[0209] In one embodiment of the compounds of formula (I), E is NR 3 and Q is CH. In another embodiment of the compounds of formula (I), E is NR 3 and Q is N.

[0210] In one embodiment of the invention, the compounds of formula (I) are compounds of formula (I.A) or compounds (I.B).

[0211]

[0212] wherein all variables have the meanings as defined for formula (I). In one embodiment, the compound of formula (I) is a compound of formula (I.A). In another embodiment, the compound of formula (I) is a compound of formula (I.B).

[0213] In one embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A), wherein,

[0214] G is phenyl or pyridyl;

[0215] W is S, S(O), S(O)2, S(O)(NRH);

[0216] R 1 is halogen;

[0217] R 3 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, and these groups are unsubstituted or halogenated;

[0218] each R 7 is independently H, halogen, OH, CN;

[0219] C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, and these groups are unsubstituted or halogenated;

[0220] a 3- to 12-membered saturated, partially unsaturated or fully unsaturated heterocycle or ring system, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O, N, or S, and is unsubstituted or substituted by one or more R H substituted;

[0221] phenyl, which is unsubstituted or substituted by one or more R J substituted;

[0222] OR K ;

[0223] C(CN)(CH3)2, or 1-cyanocyclopropyl;

[0224] each R H is independently halogen, CN; C1-C3-alkyl, C1-C3-haloalkyl;

[0225] each R J is independently halogen, CN; C1-C6-alkyl, C1-C6-alkoxy, and these groups are unsubstituted or halogenated; or for two adjacent substituents R JIn the case of being a C1-C6-alkoxy group, these substituents form an alkyl bridge between the two oxygens, which is unsubstituted or halogenated;

[0226] Each R K is a C1-C6-alkyl group, which is unsubstituted or substituted by one or more halogens;

[0227] Each R W is independently a C1-C4-alkyl group;

[0228] The subscript n is 1 or 2;

[0229] and its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

[0230] In one embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A), wherein,

[0231] G is phenyl or pyridyl;

[0232] W is S(O)2, S(O)(NRH);

[0233] R 1 is Cl or Br;

[0234] R 3 is a C1-C2-alkyl group, cyclopropyl, or cyclopropylmethyl;

[0235] Each R 7 is independently H, chlorine, bromine;

[0236] C1-C2-alkyl group, C3-C6-cycloalkyl group, these groups are unsubstituted or halogenated;

[0237] Pyridine, which is unsubstituted or substituted by one or more R H substituted;

[0238] Phenyl, which is unsubstituted or substituted by one or more R J substituted;

[0239] OR K ;

[0240] C(CN)(CH3)2, or 1-cyanocyclopropyl;

[0241] Each R H is independently halogen, CN; C1-C3-alkyl group, C1-C3-haloalkyl group;

[0242] Each R JIndependently is fluorine, chlorine, CN; C1-C6-alkyl, C1-C6-alkoxy, and these groups are unsubstituted or halogenated; or when two adjacent substituents R J are C1-C6-alkoxy, these substituents form an alkyl bridge between two oxygens, which is unsubstituted or halogenated;

[0243] Each R K is C1-C6-alkyl, which is unsubstituted or substituted by one or more halogens;

[0244] R W is ethyl or isopropyl;

[0245] The subscript n is 1 or 2;

[0246] And its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

[0247] In one embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A), wherein,

[0248] G is pyridyl;

[0249] W is S(O)2;

[0250] R 1 is Cl;

[0251] R 3 is methyl, cyclopropyl, or cyclopropylmethyl;

[0252] Each R 7 independently is H, chlorine, bromine;

[0253] C1-C2-alkyl, C3-C6-cycloalkyl, and these groups are unsubstituted or halogenated;

[0254] 1,3-benzodioxol-5-yl, which is unsubstituted or halogenated;

[0255] Pyridine, which is unsubstituted or substituted by one or more R H substituents;

[0256] Phenyl, which is unsubstituted or substituted by one or more R J substituents;

[0257] OR K ;

[0258] C(CN)(CH3)2, or 1-cyanocyclopropyl;

[0259] Each R HIndependently is halogen, CN; C1-C3-alkyl, C1-C3-haloalkyl;

[0260] Each R J Independently is fluorine, chlorine, CN; C1-C6-alkyl, C1-C6-alkoxy, these groups are unsubstituted or halogenated; or in the case where two adjacent substituents R J are C1-C6-alkoxy, these substituents form an alkyl bridge between two oxygens, which is unsubstituted or halogenated;

[0261] Each R K is C1-C6-alkyl, which is unsubstituted or substituted by one or more halogens;

[0262] R W is ethyl or isopropyl;

[0263] The subscript n is 1 or 2;

[0264] And its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

[0265] In a preferred embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A.1),

[0266]

[0267] wherein the variables R 1 , R 3 and R W have the meanings as defined for formula (I) or (I.A), and wherein the variables R 71 and R 72 have the meanings as defined for R 7 in formula (I).

[0268] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A.2),

[0269]

[0270] wherein the variables R 1 , R 3 and R W have the meanings as defined for formula (I) or (I.A), and wherein the variables R 71 and R 72 have the meanings as defined for R 7 in formula (I).

[0271] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I.A.3),

[0272]

[0273] wherein the variable R 1 , R 3 and R W have the meanings defined for formula (I) or (I.A), and wherein the variables R 71 and R 72 have the meanings defined for R 7 in formula (I).

[0274] R 1 is halogen, i.e., F, Cl, Br, or I, preferably F, Cl, or Br, more preferably Cl or Br. In one embodiment, R 1 is Cl. In another embodiment, R 1 is Br.

[0275] R 3 , R 5 are independently C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated. In one embodiment, R 3 , R 5 are independently C1-C3-alkyl, or C3-C6 cycloalkyl, these groups being unsubstituted or halogenated. In another embodiment, R 3 , R 5 are independently cyclopropyl. In one embodiment, R 3 is C1-C2-alkyl, cyclopropyl, or cyclopropylmethyl. Preferably, R 3 is cyclopropyl.

[0276] Ring G is phenyl or pyridyl. In one embodiment, G is phenyl. In another embodiment, G is pyridyl, more preferably 2-pyridyl.

[0277] Preferred ring G is shown by the following formulas A1 to A3, where "&" represents the connection to the tricyclic skeleton of the compound of formula (I). To avoid doubt, formulas A1 to A3 themselves and in combination with the following groups are preferred embodiments

[0278]

[0279] wherein "&" represents the connection to the tricyclic skeleton in formula (I). In other words, the substituents R W -W and (R 7 ) n in formulas A1 to A3 are merely illustrative, but not part of ring G.

[0280]

[0281] In one embodiment, G is A1. In another embodiment, G is A2. In another embodiment, G is A3.

[0282] The variable W is S, S(O), S(O)2 or S(O)(NR W ), preferably S(O)2. In one embodiment, the variable W is S(O)(NH). In one embodiment, the variable W is not S(O)NH, and the other variables have the meanings as described in the embodiments herein.

[0283] If G is phenyl, the subscript n is 1, 2, 3, or 4, or if G is pyridyl, the subscript n is 1, 2, or 3. Typically, n is 1 or 2. In another embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3.

[0284] In one embodiment, R 7 is independently H, halogen, OH, CN; C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, which groups are unsubstituted or halogenated; a 3- to 12-membered saturated, partially unsaturated or fully unsaturated heterocycle or ring system, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O, N, or S, and is unsubstituted or substituted by one or more R H substituents; phenyl, which is unsubstituted or substituted by one or more R J substituents; OR K ; -C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0285] In another embodiment, R 7 is halogen; C1-C3-alkyl, cyclopropyl; a 6- to 9-membered saturated, partially unsaturated or fully unsaturated heterocycle or ring system, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O or N, and is unsubstituted or substituted by one or more substituents selected from halogen, CN, C1-C3-alkyl and C1-C3-haloalkyl; phenyl, which is unsubstituted or substituted by one or more R J substituents; or OR K , where R K is C1-C3-alkyl, which is unsubstituted or substituted by CN.

[0286] In another embodiment, R 7 is selected from -C(CN)(CH3)2 and 1-cyanocyclopropyl.

[0287] In another embodiment, R 7is halogen; CH3, cyclopropyl; pyridyl, which is substituted by CN; 1,3-benzodioxol-5-yl, which is substituted by halogen; phenyl, which is substituted by halogen or C1-C3-alkoxy, and the C1-C3-alkoxy is substituted by CN. In another embodiment, R 7 is selected from -C(CN)(CH3)2 and 1-cyanocyclopropyl.

[0288] In another embodiment, R 7 is halogen; CH3, cyclopropyl; pyridyl, which is substituted by CN; 1,3-benzodioxol-5-yl, which is substituted by halogen; phenyl, which is substituted by halogen, C1-C3-alkoxy, and the C1-C3-alkoxy is substituted by CN, -C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0289] In another embodiment, R 7 is halogen; CH3, cyclopropyl; pyridyl, which is substituted by CN; 1,3-benzodioxol-5-yl, which is substituted by halogen; phenyl, which is substituted by halogen, CN, C1-C6-alkyl, C1-C6-alkoxy, and the C1-C6-alkyl and C1-C6-alkoxy are unsubstituted or halogenated; C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0290] In a preferred embodiment, R 7 is chlorine, bromine, 4-fluorophenyl, 2,4-difluorophenyl, 3,5-difluorophenyl, 2,6-dichlorophenyl, 4-chlorophenyl, methyl, cyclopropyl or phenyl substituted by C1-C2-alkyl, C1-C2-alkoxy, and the C1-C2-alkyl and C1-C2-alkoxy are unsubstituted or halogenated.

[0291] Each R H is independently halogen, CN; C1-C3 alkyl, or C1-C3 haloalkyl. Preferably, each R H is independently CN or C1-C3-haloalkyl, more preferably CN or CF3.

[0292] Each R J is independently halogen, CN; C1-C3-alkyl, or C1-C3-alkoxy, and these groups are unsubstituted or halogenated. Preferably, each R J is independently halogen, CN, or C1-C3-haloalkoxy, more preferably halogen, CN, CF3O, or CHF2O, particularly preferably halogen, CF3O, or CHF2O.

[0293] In one embodiment, there are two adjacent substituents R J, which are C1-C6-alkoxy groups such that these substituents form an alkyl bridge between the two oxygens, which is unsubstituted or halogenated.

[0294] Adjacent substituents R forming an alkylene ether bridge J Examples are as follows:

[0295]

[0296] Each R K is a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, a C3-C6-cycloalkyl group, and these groups are unsubstituted or substituted by one or more identical or different substituents selected from halogen and CN. Preferably, each R K is a C1-C3-alkyl group substituted by CN, more preferably isopropyl substituted by CN, especially 1-cyanoisopropyl.

[0297] R W is a C1-C4-alkyl group or cyclopropyl, preferably ethyl or isopropyl.

[0298] Formula I.A.1 is a preferred embodiment falling under the definition of formula I.A, where n is 2, and where the residues R 71 and R 72 have the definitions according to R 7 .

[0299]

[0300] Table A below represents specific compounds in the combinations of definitions for the substituents R 1 and R 71 in lines L.1 to L.75. Each combination independently and all combinations collectively represent preferred embodiments. Each group mentioned for the substituents in the table by itself (independent of the combination in which it is mentioned) is furthermore a particularly preferred aspect of the substituents under discussion.

[0301]

[0302]

[0303]

[0304]

[0305] Table A: Preferred combinations I.1 to I.75 of R 1 and R 71

[0306] Particularly preferred embodiments of the invention are listed in Tables 1 to 4, corresponding to specific compounds falling under formula I.A.

[0307] Table 1: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is H, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0308] Table 2: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is CH3, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0309] Table 3: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is CH2CH3, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0310] Table 4: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is Cl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0311] Table 5: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is Br, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0312] Table 6: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is cyclopropyl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0313] Table 7: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is ethyl, R 72 is isopropyl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0314] Table 8: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is ethyl, R 72 is N - imidazolyl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0315] Table 9: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is ethyl, R 72 is N - triazolyl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0316] Table 10: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is isopropyl, R 72 is H, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0317] Table 11: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is isopropyl, R 72 is CH3, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0318] Table 12: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is isopropyl, R 72 is CH2CH3, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0319] Table 13: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is isopropyl, R 72 is Cl, and the combination of R 1 and R 71 is defined as in the rows of Table A.

[0320] Table 14: Compounds of formula I.A.1, wherein R 3 is cyclopropyl, R W is isopropyl, R 72 is Br, and the combination of R 1 and R71 The combination is defined in the rows of Table A.

[0321] Table 15: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is isopropyl, R 72 is cyclopropyl, and R 1 and R 71 The combination is defined in the rows of Table A.

[0322] Table 16: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is isopropyl, R 72 is isopropyl, and R 1 and R 71 The combination is defined in the rows of Table A.

[0323] Table 17: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is isopropyl, R 72 is N - imidazolyl, and R 1 and R 71 The combination is defined in the rows of Table A.

[0324] Table 18: Compounds of formula I.A.1, where R 3 is cyclopropyl, R W is isopropyl, R 72 is N - triazolyl, and R 1 and R 71 The combination is defined in the rows of Table A.

[0325] In a preferred embodiment, the compound of formula (I) is a compound of formula (I.A), where G is pyridyl,

[0326] R 1 is halogen;

[0327] R 3 is cyclopropyl;

[0328] R W is C1 - C4 - alkyl, cycloalkyl;

[0329] n is 1 or 2;

[0330] R 7 is selected from

[0331] halogen;

[0332] C1 - C3 - alkyl, cyclopropyl;

[0333] 6 to 9 yuan saturated, partially unsaturated or fully unsaturated heterocycles or ring systems, wherein the heterocycles or ring systems contain one or more identical or different heteroatoms O or N, and are unsubstituted or substituted by one or more substituents selected from halogen, CN, C1-C3-alkyl, and C1-C3-haloalkyl;

[0334] phenyl, which is unsubstituted or substituted by one or more R J substituents; or

[0335] OR K wherein R K is C1-C3-alkyl, which is unsubstituted or substituted by CN;

[0336] -C(CN)(CH3)2, and 1-cyanocyclopropyl.

[0337] In another preferred embodiment, the compound of formula (I) is a compound of formula (I.A), wherein G is pyridyl,

[0338] R 1 is halogen;

[0339] R 3 is cyclopropyl;

[0340] R W is C1-C4-alkyl, cycloalkyl;

[0341] n is 1 or 2;

[0342] R 7 is phenyl, in the case where two adjacent substituents R J are C1-C6-alkoxy, wherein two R J form an alkyl bridge between the two oxygens, which is unsubstituted or halogenated.

[0343] In another preferred embodiment, the compound of formula (I) is a compound of formula (I.A), wherein G is pyridyl,

[0344] R 1 is halogen;

[0345] R 3 is cyclopropyl;

[0346] R W is C1-C3-alkyl;

[0347] n is 1 or 2;

[0348] R 7 is selected from

[0349] halogen; CH3, cyclopropyl; pyridyl, which is substituted by CN; 1,3-benzodioxol-5-yl, which is substituted by halogen; phenyl, which is substituted by halogen, C1-C3-alkoxy, and the C1-C3-alkoxy is substituted by CN, -C(CN)(CH3)2, or 1-cyanocyclopropyl.

[0350] The term "compounds of the invention" refers to compounds of formula I, or "Compound I", and includes their salts, tautomers, stereoisomers, and N-oxides.

[0351] The invention also relates to an agrochemical composition comprising auxiliaries and at least one Compound I.

[0352] The agrochemical composition comprises a pesticidally effective amount of Compound I.

[0353] Compound I can be converted into common types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and mixtures thereof. Examples of 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, pills, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials (e.g., seeds). These and additional composition types are defined in "Catalogue of pesticide formulation types and international coding system [Catalogue of Pesticide Formulation Types and International Coding System]", Technical Monograph [Technical Monograph] No. 2, 6th Edition, May 2008, CropLife International. These compositions are prepared in a known manner, for example as described by: Mollet and Grubemann, Formulation technology [Formulation Technology], Wiley VCH [Wiley VCH Verlag], Weinheim, 2001; or Knowles, New developments in crop protection product formulation [New Developments in Crop Protection Product Formulation], Agrow Reports [Agrow Reports] DS243, T&F Informa [T&F Informa Verlag], London, 2005.

[0354] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezes, defoamers, colorants, tackifiers and binders.

[0355] Suitable solvents and liquid carriers are water and organic solvents. Suitable solid carriers or fillers are mineral soils.

[0356] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Edition or North American Edition). Suitable anionic surfactants are the alkali metal salts, alkaline earth metal salts, or ammonium salts of sulfonic acids, sulfuric acids, phosphoric acids, carboxylic acids. Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants. Suitable cationic surfactants are quaternary ammonium surfactants.

[0357] Agrochemical compositions generally contain an active substance in an amount of from 0.01% to 95% by weight, preferably from 0.1% to 90% by weight, and most preferably from 0.5% to 75% by weight. The active substance is used in a purity of from 90% to 100%, preferably from 95% to 100%.

[0358] Various types of oils, wetting agents, adjuvants, or fertilizers can be added as a premix or (if appropriate) added until immediately before use (tank mixing) to the active substance or the composition containing them. These reagents can be mixed with the composition according to the invention in a weight ratio of from 1:100 to 100:1.

[0359] The user generally applies the composition according to the invention by means of a pre-application device, a knapsack sprayer, a spray tank, a spray aircraft, or an irrigation system. Generally, the agrochemical composition is made up with water, a buffer and / or additional auxiliaries to the desired application concentration and thus a ready-to-use spray liquid or agrochemical composition according to the invention is obtained. Generally, 20 to 2000 liters of the ready-to-use spray liquid are applied per hectare of agricultural useful area.

[0360] Compound I is suitable for protecting crops, plants, plant propagation materials (such as seeds), or the soil or water body in which plants grow from being attacked or infested by animal pests. Accordingly, the present invention also relates to a method for plant protection, which comprises bringing into contact a crop, a plant, a plant propagation material (such as seeds), or the soil or water body in which plants grow, which is to be protected from being attacked or infested by animal pests, with a pest-killing effective amount of Compound I.

[0361] Compound I is also suitable for combating or controlling animal pests. Accordingly, the present invention also relates to a method for combating or controlling animal pests, which comprises bringing into contact an animal pest, its habitat, breeding ground, or food supply, or a crop, a plant, a plant propagation material (such as seeds), or the soil, or the area, material, or environment in which an animal pest grows or may grow, with a pest-killing effective amount of Compound I.

[0362] Compound I is effective for any and all developmental stages, such as eggs, larvae, pupae, and adults, by both contact and ingestion.

[0363] Compound I can be applied as such or in the form of compositions containing them.

[0364] Application can be carried out both before and after the crop, plant, or plant propagation material is infested by pests.

[0365] The term "contact" includes both direct contact (applying the compound / composition directly to the animal pest or the plant) and indirect contact (applying the compound / composition to the site).

[0366] The term "animal pest" includes arthropods, gastropods, and nematodes. Preferred animal pests according to the present invention are arthropods, preferably insects and arachnids, especially insects.

[0367] The term "plant" includes cereals such as durum wheat and other wheats, rye, barley, triticale, oats, rice, or maize (forage maize and sweet maize / sweet corn and field corn); sugar beet such as sugar beet or fodder beet; fruits such as pomes, drupes, or soft fruits such as apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants such as kidney beans, lentils, peas, alfalfa, or soybeans; oil plants such as rapeseed (oilseed rape), Brassica napus, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbitaceous plants such as squashes, pumpkins, cucumbers or melons; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as aubergines, spinach, lettuce (such as iceberg lettuce), chicory, cabbages, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; laurel plants such as avocados, cinnamon, or camphor; energy and raw material plants such as maize, soybeans, rapeseed, sugar cane or oil palms; tobacco; nuts such as walnuts; pistachios; coffee; tea; bananas; vines; hops; stevia (Stevia rebaudiana); natural rubber plants or ornamental and forestry plants, shrubs, broad-leaved trees or evergreens, eucalypts; turf; lawns; grasses. Preferred plants include potatoes, sugar beet, tobacco, wheat, rye, barley, oats, rice, maize, cotton, soybeans, rapeseed, beans, sunflowers, coffee, or sugar cane; fruits; vines; ornamental plants; or vegetables such as cucumbers, tomatoes, kidney beans or squashes.

[0368] The term "seed" includes seeds and plant propagules, including true seeds, seed pieces, suckers, bulbs, corms, fruits, tubers, grains, cuttings, cut shoots, and preferably means true seeds.

[0369] "Pest - killing effective amount" means the amount of the active ingredient required to achieve an observable effect on growth, the effect including necrosis, death, retardation, prevention and elimination, destruction or otherwise reduction in the occurrence and activity of the target organism. For the various compounds / compositions used in the present invention, the pest - killing effective amount can vary. The pest - killing effective amount of a composition also varies according to main conditions such as the desired pest - killing effect and duration, climate, target species, location, and application method.

[0370] For use in treating crop plants, for example, by foliar application, the application rate of the active ingredient of the present invention can range from 0.0001 g to 4000 g per hectare, such as from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, and ideally from 1 g to 100 g per hectare.

[0371] Compound I is also suitable for combating non-crop insect pests. For use in combating said non-crop pests, Compound I can be used as a bait composition, a gelling agent, a normal insect spray, an aerosol, for ultra-low volume application and in mosquito nets (by impregnation or surface application).

[0372] The term "non-crop insect pest" refers to pests that are particularly relevant to non-crop targets, such as ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches, such as: Aedes aegypti, Musca domestica, Tribolium spp.; termites, such as Reticulitermes flavipes, Coptotermes formosanus; cockroaches, such as Blattella germanica, Periplaneta Americana; ants, such as Solenopsis invicta, Linepithema humile, and Camponotus pennsylvanicus.

[0373] The bait can be a liquid, solid or semi-solid preparation (such as a gelling agent). For use in a bait composition, the typical content of the active ingredient is 0.001 wt% to 15 wt%, desirably 0.001 wt% to 5 wt% of the active compound.

[0374] Compound I and its compositions can be used to protect wooden materials, such as trees, wooden fences, sleepers, frames, works of art, etc., as well as buildings, and building materials, furniture, leather, fibers, vinyl products, wires and cables, etc., from ants, termites and / or beetles that damage wood or textiles, and for controlling the damage caused by ants and termites to crops or humans (for example when the pests invade houses and public facilities or nest in gardens, orchards or parks).

[0375] The conventional application rate in the protected material is, for example, 0.001 g to 2000 g or 0.01 g to 1000 g of the active compound per m 2 of the treated material, desirably 0.1 g to 50 g per m 2 .

[0376] The insecticidal composition for use in impregnated materials typically contains 0.001 wt% to 95 wt%, preferably 0.1 wt% to 45 wt%, and more preferably 1 wt% to 25 wt% of at least one repellent and / or insecticide.

[0377] Pest

[0378] The compounds of the present invention are particularly suitable for effectively combating animal pests, such as arthropods and nematodes, including:

[0379] Insects from the following suborders: Auchenorrhyncha, such as Amrasca biguttula, Empoasca spp., Nephotettix virescens, Sogatella furcifera, Mahanarva spp., Laodelphax striatellus, Nilaparvata lugens, Diaphorina citri;

[0380] Lepidoptera, such as Helicoverpa spp., Heliothis virescens, Lobesia botrana, Ostrinia nubilalis, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Spodoptera spp., Trichoplusia ni, Tuta absoluta, Cnaphalocrocis medialis, Cydia pomonella, Chilo suppressalis, Anticarsia gemmatalis, Agrotis ipsilon, Chrysodeixis includens;

[0381] True bugs, such as Lygus spp., Stink bugs such as Euschistus spp., Halyomorpha halys, Nezara viridula, Piezodorus guildinii, Dichelops furcatus;

[0382] Thrips, such as species of Frankliniella spp., Thrips spp., Dichromothrips corbettii;

[0383] Aphids, such as Acyrthosiphon pisum, Aphis spp, Myzus persicae, Rhopalosiphum spp., Schizaphis graminum, Megoura viciae;

[0384] Whiteflies, such as Trialeurodes vaporariorum, Bemisia spp.;

[0385] Coleoptera, such as Phyllotreta spp., Melanotus spp., Meligethes aeneus, Leptinotarsa decemlineata, Ceutorhynchus spp., Diabrotica spp., Anthonomus grandis, Atomaria linearia, Agriotes spp., Epilachna spp.;

[0386] Flies, such as Delia spp., Ceratitis capitate, Bactrocera spp., Liriomyza spp.;

[0387] Coccoidea, such as Aonidiella aurantii, Ferrisia virgate;

[0388] Arachnida arthropods (mites), such as Penthaleus major, Tetranychus spp.;

[0389] Nematodes, such as Heterodera glycines, Meloidogyne spp., Pratylenchus spp., Caenorhabditis elegans.

[0390] In one embodiment, the pest is selected from Phyllophaga spp, Limonius spp, Popillia japonica.

[0391] Animal health

[0392] Compound I is suitable for treating or protecting animals against parasite infestation or infection. Accordingly, the present invention also relates to the use of the compounds of the present invention for the manufacture of a medicament for treating or protecting animals against parasite infestation or infection. In addition, the present invention relates to a method of treating or protecting animals against parasite infestation and infection, the method comprising orally, topically or parenterally administering or applying to the animal a parasitically effective amount of Compound I.

[0393] The present invention also relates to the non-therapeutic use of the compounds of the present invention for treating or protecting animals against parasite infestation and infection. In addition, the present invention relates to a non-therapeutic method of treating or protecting animals against parasite infestation and infection, the non-therapeutic method comprising applying to a locus a parasitically effective amount of Compound I.

[0394] The compounds of the present invention are further suitable for use in combating or controlling parasites in and on animals. In addition, the present invention relates to a method of combating or controlling parasites in and on animals, the method comprising bringing the parasites into contact with a parasitically effective amount of Compound I.

[0395] The present invention also relates to the non-therapeutic use of Compound I for controlling or combating parasites. In addition, the present invention relates to a non-therapeutic method of combating or controlling parasites, the non-therapeutic method comprising applying to a locus a parasitically effective amount of Compound I.

[0396] Compound I can be effective by both contact (via soil, glass, walls, mosquito nets, carpets, blankets or animal parts) and ingestion (e.g., bait). In addition, Compound I can be applied to any and all developmental stages.

[0397] Compound I can be applied as such or in the form of a composition containing them.

[0398] The term "locus" means a habitat, food supply, breeding ground, area, material or environment in which the parasite grows or may grow outside the animal.

[0399] As used herein, the term "parasite" includes endoparasites and ectoparasites. In some embodiments of the present invention, endoparasites may be preferred. In other embodiments, ectoparasites may be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bot fly larvae of sheep, ked of sheep, stable flies, house flies, flies, maggot fly larvae, chiggers, black flies, mosquitoes and fleas.

[0400] The compounds of the present invention are particularly useful against the following parasites: Cimex lectularius, Rhipicephalus sanguineus, and Ctenocephalides felis.

[0401] As used herein, the term "animal" includes warm-blooded animals (including humans) and fish. Mammals are preferred, such as cattle, sheep, pigs, camels, deer, horses, swine, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks, and fish such as freshwater fish and saltwater fish such as salmon, carp and eels. Domestic animals such as dogs or cats are particularly preferred.

[0402] Compound I can be administered in a total amount of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day.

[0403] For oral administration to warm-blooded animals, Compound I can be formulated as animal feed, animal feed premix, animal feed concentrate, pills, solutions, pastes, suspensions, infusions, gels, tablets, boluses and capsules. For oral administration, the dosage form selected should provide the animal with Compound I at 0.01 mg / kg to 100 mg / kg of animal body weight per day, preferably 0.5 mg / kg to 100 mg / kg of animal body weight per day.

[0404] Alternatively, Compound I can be administered parenterally to animals, for example by intracavitary, intramuscular, intravenous or subcutaneous injection. For subcutaneous injection, Compound I can be dispersed or dissolved in a physiologically acceptable carrier. Alternatively, Compound I can be formulated as an implant for subcutaneous administration. Additionally, Compound I can be administered transdermally to animals. For parenteral administration, the dosage form selected should provide the animal with Compound I at 0.01 mg / kg to 100 mg / kg of animal body weight per day.

[0405] Compound I can also be administered topically to animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-ons, and pour-ons, as well as in the form of ointments or oil-in-water or water-in-oil emulsions. For topical administration, dips and sprays generally contain from 0.5 ppm to 5,000 ppm, and preferably from 1 ppm to 3,000 ppm of Compound I. Additionally, Compound I can be formulated into ear tags for animals, especially quadrupeds (such as cattle and sheep).

[0406] The oral solution is administered directly.

[0407] The solution for use on the skin is dropped, applied, rubbed, sprinkled, or sprayed.

[0408] The gel is applied or spread on the skin or introduced into body cavities.

[0409] The pour-on formulation is poured or sprayed onto a defined area of the skin, and the active compound penetrates the skin and acts systemically. The pour-on formulation is prepared by dissolving, suspending, or emulsifying the active compound in a suitable skin-compatible solvent or solvent mixture.

[0410] The emulsion can be administered orally, transdermally, or as an injection.

[0411] The suspension can be administered orally or topically / transdermally.

[0412] The semi-solid preparation can be administered orally or topically / transdermally.

[0413] To produce solid preparations, the active compound is mixed with suitable excipients, and if appropriate, additives are added, and the desired dosage form is prepared.

[0414] The compositions that can be used in the present invention generally can contain from about 0.001% to 95% of Compound I.

[0415] Ready-to-use preparations contain, at a concentration of from 10 ppm to 80% by weight, preferably from 0.1% to 65% by weight, more preferably from 1% to 50% by weight, and most preferably from 5% to 40% by weight, a compound that acts against parasites, preferably ectoparasites.

[0416] Preparations to be diluted before use contain, at a concentration of from 0.5% to 90% by weight, preferably from 1% to 50% by weight, a compound that acts against ectoparasites.

[0417] In addition, the preparations contain, at a concentration of from 10 ppm to 2% by weight, preferably from 0.05% to 0.9% by weight, and very particularly preferably from 0.005% to 0.25% by weight, a compound of formula I that acts against endoparasites.

[0418] Solid formulations that can release the compounds of the present invention in a total amount of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, and most preferably 25 mg / kg to 160 mg / kg of the body weight of the treated animals within three weeks can be administered.

[0419] The following examples illustrate the present invention.

[0420] A. Preparation of Compounds

[0421] Materials: Unless otherwise indicated, reagents and solvents were purchased in the highest commercial quality and used without further purification.

[0422] All reactions were monitored by thin layer chromatography (TLC) using Merck silica gel 60F254 pre-coated plates (0.25 mm). Flash chromatography was performed using Agela technologies silica gel (Agela techno, silica irregular 40 - 60 μm , 60A, catalog number C - CS1400).

[0423] 1 1H NMR spectra were recorded on a Bruker (500 MHz). Chemical shifts are expressed in ppm downfield from the internal solvent peaks of DMSO - d6 ( 1 1H; δ = 2.50 ppm) ( 1 1H; δ = 2.50 ppm) and CD3OD ( 1 1H; δ = 3.30 ppm), and coupling constants J are given in Hertz. The following abbreviations are used to explain multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, dd = double doublet, dt = double triplet, m = multiplet, br = broad peak. High resolution mass spectra were measured on a JEOL JMS - T100LP.

[0424] Characterization: Compounds were characterized by high performance liquid chromatography coupled with mass spectrometry (HPLC / MS).

[0425] Method A: UHPLC - MS, on a Shimadzu LCMS2020ESI. Analytical UHPLC column: C - 18, 50 mm, 4.6 mm, 5 μm; mobile phase: 100 mM ammonium formate, B: acetonitrile, flow rate: 1.2 mL / min, injection volume: 1 μL, within 1.50 min; gradient: 10% B to 100% B within 1.5 min, hold 100% B for 1 min, 10% B at 2.51 min; run time: 3 min at 400 °C. MS method: ESI positive; mass range (m / z) 100 - 800.

[0426] Method B: Waters (ACQUITY-H Class UPLC, analytical UHPLC column), mass detector 3100: BEH-C-18, 50 mm, 2.1 mm, 1.7 µm; mobile phase: A: 0.1% formic acid, 10% IPA in water. B: 0.1% formic acid in acetonitrile. C: 20 mM ammonium formate in water. Flow rate: 1.2 mL / min, injection volume: 1 µL, within 1.50 minutes; gradient: 10% A to 100% B in 1.5 min, hold 100% B for 1 min, 10% B at 2.51 min; run time: 3 min at 400 °C. MS method: ESI positive; mass range (m / z) 100 - 800.

[0427] Abbreviations used: min is minute; ACN is acetonitrile; DCM is dichloromethane; DMF is dimethylformamide; THF is tetrahydrofuran; mL is milliliter; min is minute; h is hour

[0428] Synthesis Example 1: Preparation of 7-chloro-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridinyl]imidazo [1,2-c]pyrimidin-5-one (Compound I.1)

[0429] Step - 1: Preparation of 5-bromo-3-ethylthio-pyridine-2-carbonitrile

[0430] Under a N2 atmosphere, at a holding temperature between -40 °C and -50 °C, over a period of 30 min, sodium ethanethiolate (11 g, 0.105 mol) was added in portions to a stirred solution of 5-bromo-3-nitro-pyridine-2-carbonitrile (20 g, 0.087 mol) in DMF (200 mL) at -40 °C. The resulting reaction mixture was stirred at the same temperature for 10 minutes and then gradually allowed to reach a temperature of 20 °C to 25 °C while continuing to stir for 1 h. After completion of the reaction, the above reaction mixture was quenched, extracted, and the organic layer was washed. The combined organic layers were dried and concentrated under reduced pressure to obtain a crude material, which was purified by column chromatography to obtain 5-bromo-3-ethylthio-pyridine-2-carbonitrile as a yellow solid (17 g, 82% yield). H 1 NMR (500 MHz, CDCl3): δ 8.52 (s, 1H), 7.85 (s, 1H), 3.07 (q, 2H, J = 10 Hz), 1.43 (t, 3H, J = 7.3 Hz). LC-MS: [M + H] + Calculated mass value: 243, measured value: 244.

[0431] Step - 2: Preparation of 1-(5-bromo-3-ethylthio-2-pyridyl)ethanone

[0432] At 0 °C to -5 °C, under a N2 atmosphere, over a period of 30 min, methylmagnesium bromide (2 equivalents) was added dropwise to a stirred solution of 5-bromo-3-ethylthio-pyridine-2-carbonitrile (17 g, 0.069 mol) in THF (170 mL) at 0 °C. The resulting reaction mixture was allowed to stir at 0 °C for 2 h. After completion of the reaction, the above reaction mixture was quenched with 1 N aqueous HCl (250 mL) and extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure to obtain a crude material, which was purified by crystallization. The obtained solid was filtered and dried under reduced pressure to obtain 1-(5-bromo-3-ethylthio-2-pyridyl)ethanone as a yellow solid (14 g, 82% yield). H 1 NMR (500 MHz, DMSO): δ 8.57 (s, 1H), 8.05 (s, 1H), 3.01 (q, 2H, J = 10 Hz), 2.59 (s, 3H), 1.26 (t, 3H, J = 7.3 Hz). LC-MS: [M+H] + Calculated mass value: 260, measured value: 261.

[0433] Step - 3: Preparation of 1-(5-bromo-3-ethylsulfonyl-2-pyridyl)ethanone

[0434] To a stirred solution of 1-(5-bromo-3-ethylthio-2-pyridyl)ethanone (3.9 g, 0.018 mol) in DCM (40 mL) at 0 °C was added m-chloroperbenzoic acid (9.7 g, 0.039 mol). The resulting reaction mixture was stirred at 20 °C to 25 °C for 3 - 4 h. After completion of the reaction, the above reaction mixture was quenched and extracted. The organic layer was washed, dried and concentrated under reduced pressure to obtain 1-(5-bromo-3-ethylsulfonyl-2-pyridyl)ethanone as an off-white solid (3.2 g, 82% yield). H 1 NMR (500 MHz, CDCl3): δ 9.12 (s, 1H), 8.55 (s, 1H), 3.55 (q, 2H J = 12 Hz), 2.5 (s, 3H), 1.20 (t, 3H, J = 7 Hz). LC-MS: [M+H] + Calculated mass value: 291, measured value: 292.

[0435] Step - 4: Preparation of 1-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]ethanone

[0436] To a stirred solution of 1-(5-bromo-3-ethylsulfonyl-2-pyridyl)ethenone (10 gm, 0.342 mol) in dioxane (95 ml) was added 4-fluorophenylboronic acid (4.7 gm, 0.342 mol) and stirred for a few minutes until a clear solution was obtained. 5 ml of H2O was added to the reaction mass, followed by K2CO3 (14.919 gm, 1.026 mol) and allowed to stir for 5 min under continuous N2 purge via gas injection. Finally, Pd(PPh3)4 (1.977 gm, 0.0171 mol) was added to the reaction mass. Then the reaction was allowed to stir for a period of 2 hours at 100 °C. After completion of the reaction, the above reaction mass was cooled, quenched and extracted. Then, the organic layer was washed, dried and concentrated under reduced pressure to obtain the crude material, which was purified by column to obtain 1-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]ethanone as an off-white solid (8 g, 82% yield). 1 H NMR (300 MHz, DMSO-d6) δ 9.25 (d, J = 2.1 Hz, 1H), 8.52 (d, J = 2.1 Hz, 1H), 8.02 - 7.89 (m, 2H), 7.49 - 7.35 (m, 2H), 3.60 (q, J = 7.4 Hz, 2H), 2.54 (s, 3H), 1.25 (t, J = 7.4 Hz, 3H). LC-MS: C 15 H 14 FNO3S [M] + Calculated mass for: 307, found: 308.

[0437] Step - 5: Preparation of 2-bromo-1-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]ethanone

[0438] To a stirred solution of 1-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]ethanone (3 g, 0.010 mol) in chloroform (30 mL) at 0 °C was added CH3COOH (30 mL) and HBr in acetic acid (30 mL) and stirred for a few minutes. Then bromine (2 g, 0.012 mol) in CHCl3 was added. The resulting reaction mixture was heated to 60 °C for 1 h. After completion of the reaction, the above reaction mixture was quenched, extracted, and the organic layer was washed. The combined organic layers were dried and concentrated under reduced pressure to obtain the crude material, which was purified by column chromatography to obtain 2-bromo-1-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]ethanone as an off-white solid (2.2 g, 82% yield). 11H NMR (300 MHz, DMSO-d6) δ 9.23 (d, J = 2.1 Hz, 1H), 8.61 (m, 1H), 7.92 (ddd, J = 8.7, 5.3, 2.7 Hz, 2H), 7.43 - 7.29 (m, 2H), 4.90 (s, 2H), 3.57 (q, J = 7.4 Hz, 2H), 1.18 (t, J = 7.4 Hz, 3H). LC-MS: C 15 H 13 BrFNO3S [M] + Calculated mass for: 386, found: 386.1.

[0439] Step - 6: Preparation of 1-benzyl-3-cyclopropyl-urea

[0440] At 0 °C, a solution of benzyl isocyanate (25 g, 0.187 mol, 1 equiv) in DCM (dichloromethane) (100 mL) was added to a solution of cyclopropylamine (16 g, 0.281 mol, 1.5 equiv) and triethylamine (51 mL, 0.375 mol, 2 equiv) in DCM (dichloromethane) (1 L). The reaction mixture was gradually warmed to 20 °C to 25 °C and stirred for 1 h. After completion of the reaction, it was diluted with DCM until a clear solution was observed. The organic layer was treated with 1 M aqueous HCl (500 ml), followed by treatment with saturated aqueous NaHCO3 (500 mL). The combined organic extracts were washed with water and brine. Then it was dried and concentrated to give 1-benzyl-3-cyclopropyl-urea as a white solid (35 g, 97%).

[0441] 1 1H NMR (300 MHz, DMSO-d6) δ 7.37 - 7.16 (m, 5H), 6.39 (t, J = 6.1 Hz, 1H), 6.21 (d, J = 2.6 Hz, 1H), 4.22 (d, J = 6.1 Hz, 2H), 2.43 (tq, J = 6.8, 3.4 Hz, 1H), 0.67 - 0.49 (m, 2H), 0.40 - 0.29 (m, 2H). LC-MS: C 11 H 14 N2O [M] + Calculated mass for: 190, found: 191.

[0442] Step - 7: Preparation of 6-amino-1-benzyl-3-cyclopropyl-pyrimidine-2,4-dione

[0443] At 0 °C, acetic anhydride was slowly added to a stirred solution of 1-benzyl-3-cyclopropyl-urea (65 g, 0.3684 mol, 1 equiv) and cyanoacetic acid (37.57 g, 0.4421 mol, 1.2 equiv). The resulting reaction mixture was stirred at 100 °C for 3 - 4 h. After completion of the reaction, the above reaction mixture was quenched and extracted. The organic layer was washed with water, dried and concentrated under reduced pressure to obtain an intermediate, which was purified by column chromatography to obtain the desired intermediate (45 gm, 51%). The intermediate was then taken up in 10 volumes of water and subsequently treated with an aqueous solution of 2N NaOH (4 volumes) at 20 °C to 25 °C. The resulting reaction mixture was stirred at 20 °C to 25 °C for 30 min, the precipitated white solid was separated, filtered through a Buchner funnel, and the obtained solid cake was washed with water and dried under reduced pressure to obtain 6-amino-1-benzyl-3-cyclopropyl-pyrimidine-2,4-dione as a white solid (42 g, 47%).

[0444] 1 H NMR (500 MHz, chloroform-d) δ 7.45 - 7.31 (m, 4H), 7.31 - 7.25 (m, 1H), 5.19 (s, 2H), 5.01 (s, 1H), 2.74 (tt, J = 7.1, 4.0 Hz, 1H), 1.22 - 1.10 (m, 2H), 0.94 - 0.83 (m, 2H). LC-MS: C 14 H 15 N3O2 [M] + Calculated mass for: 257, Found: 258.

[0445] Step - 8: Preparation of 6-amino-3-cyclopropyl-1H-pyrimidine-2,4-dione

[0446] To a stirred solution of 6-amino-1-benzyl-3-cyclopropyl-pyrimidine-2,4-dione (7 g, 0.0272 mol, 1 equiv) in CH3OH (350 mL) at 25 °C was added potassium formate (22.87 g, 0.2723 mol, 10 equiv) to observe a clear solution, and then 10% Pd / C (1.44 gm, 0.05 equiv) was added at 20 °C to 25 °C while maintaining an inert atmosphere. The resulting reaction mixture was heated to 70 °C for 1.5 h. After consumption of the starting material was observed by TLC, the reaction mass was allowed to rise to 50 °C, and then the reaction mixture was filtered through a bed of diatomaceous earth at 50 °C. Subsequently, the bed of diatomaceous earth was washed with hot CH3OH (50 °C), the filtrate containing the reaction mass was concentrated to dryness, and 10 volumes of water was added to the concentrate. Subsequently, at a temperature of 0 °C, the pH was adjusted to the range of 5 to 6 with 6N HCl. The solid obtained was filtered and washed with water to give 6-amino-3-cyclopropyl-1H-pyrimidine-2,4-dione as a white solid (80% to 90% yield). 1 H NMR (500 MHz, DMSO-d6) δ 10.10 (s, 1H), 6.03 (s, 1H), 4.42 (d, J = 1.7 Hz, 1H), 2.33 (td, J = 7.1, 3.6 Hz, 1H), 0.79 (t, J = 6.9 Hz, 2H), 0.55 (p, J = 5.2 Hz, 2H). LC-MS: C7H9N3O2 [M] + Calculated mass for: 167, found: 168.

[0447] Step - 9: Preparation of 6-amino-4-chloro-3-cyclopropyl-1,6-dihydropyrimidin-2-one

[0448] At 20 °C to 25 °C, POCl3 (1 mL) was slowly added to 6-amino-3-cyclopropyl-1H-pyrimidine-2,4-dione (0.5 gm), and then the reaction mixture was gradually heated to 130 °C and stirred for 12 h. The reaction was concentrated under reduced pressure to remove POCl3, and then the reaction mixture was slowly added to 4 volumes of ice water and adjusted (pH = 10) with 6N aqueous NaOH to precipitate a solid. The solid was separated, filtered through a Buchner funnel, washed with water, and evaporated to dryness to give 6-amino-4-chloro-3-cyclopropyl-1,6-dihydropyrimidin-2-one as a yellow solid (60% yield). 1 H NMR (500 MHz, DMSO-d6) δ 10.45 (s, 1H), 7.13 (d, J = 2.1 Hz, 1H), 3.57 (d, J = 2.1 Hz, 1H), 2.92 (s, 1H), 0.84 (s, 2H), 0.64 (s, 2H). LC-MS: C7H8ClN3O [M]+ Calculated mass value: 185, measured value: 186.

[0449] Step - 10: Preparation of 7-chloro-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridyl]imidazo[1,2-c]pyrimidin-5-one (Compound I.1)

[0450] To a stirred solution of 6-amino-4-chloro-3-cyclopropyl-1,6-dihydropyrimidin-2-one (1 g, 5.34 mmol) in tert-butanol (10 mL) was added 2-bromo-1-[2-ethylsulfonyl-4-(4-fluorophenyl)phenyl]ethanone (2.04 g, 5.34 mmol). Molecular sieves were added to the above reaction mixture (1 g) and the resulting reaction mixture was heated to 95 °C for 16 h. After completion of the reaction, the above reaction mixture was filtered through a bed of diatomaceous earth, the filtrate was collected and concentrated under reduced pressure to give a crude product. The crude product was purified by column chromatography to give 7-chloro-6-cyclopropyl-2-[2-ethylsulfonyl-4-(4-fluorophenyl)phenyl]imidazo[1,2-c]pyrimidin-5-one as a yellow solid (0.75 g, 30.08% yield).

[0451] 1 H NMR (300 MHz, DMSO-d6) 1 H NMR (300 MHz, DMSO-d6) δ 9.25 (d, J = 2.2 Hz, 1H), 8.54 (d, J = 2.2 Hz, 1H), 8.15 (s, 1H), 7.99 - 7.89 (m, 2H), 7.42 (t, J = 8.8 Hz, 2H), 7.12 (s, 1H), 4.08 (q, J = 7.4 Hz, 2H), 3.09 (s, 1H), 1.25 (m, 5H), 1.06 (m, 2H). LC-MS: C 22 H 18 ClFN4O3S [M] + Calculated mass value: 472, measured value: 473.

[0452] Synthesis Example 2: Preparation of 7-bromo-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridinyl]imidazo [1,2-c]pyrimidin-5-one (Compound I.4)

[0453] To a stirred solution of 7-chloro-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridinyl]imidazo[1,2-c]pyrimidin-5-one (Compound I.1, 0.6 g, 1.2 mmol) in CH3COOH (6 mL) was added HBr in CH3COOH (0.6 mL, 1.9 mmol), and the resulting reaction mixture was heated to 120 °C for 16 h. After completion of the starting material, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give the crude material. The crude material was then purified by column chromatography to give 7-bromo-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-2-pyridinyl]imidazo[1,2-c]pyrimidin-5-one as a beige solid (0.5 g, 75% yield). 1H NMR (500 MHz, DMSO-d6) δ 9.26 - 9.22 (m, 1H), 8.54 (t, J = 1.9 Hz, 1H), 8.15 (s, 1H), 7.97 - 7.91 (m, 2H), 7.42 (td, J = 8.0, 7.3, 1.8 Hz, 2H), 7.26 (s, 1H), 4.08 (q, J = 7.4 Hz, 2H), 3.25 (s, 1H), 1.25 (m, 3H), 1.21 (m, 2H), 1.06 (m, 2H). LC-MS: C 22 H 18 BrFN4O3S [M] + Calculated mass for: 517.3, found: 519.2 [M+2].

[0454] Synthesis Example 3: Preparation of 7-chloro-6-cyclopropyl-2-[3-ethylsulfonyl-5-(4-fluorophenyl)-6-methyl-2-pyridinyl] imidazo[1,2-c]pyrimidin-5-one (Compound I.5)

[0455] Step - 1: Preparation of 5-fluoro-2-methyl-pyridin-3-amine

[0456] A stirred solution of 2-bromo-5-fluoro-pyridin-3-amine (15 g, 78.53 mmol), 50% trimethylcyclotriboroxane in THF (39.4 mL, 157.1 mmol) and K2CO3 (27.13 g, 196.734 mmol) in 1,4-dioxane (120 mL) and H2O (20 mL) was degassed under N2 atmosphere for 15 min and then [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (3.02 g, 3.92 mmol) was added. The resulting reaction mixture was heated to 120 °C for 6 - 7 h. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give the crude material. The crude material was purified by column chromatography to give 5-fluoro-2-methyl-pyridin-3-amine (7 g, 60% yield).1 1H NMR (500 MHz, DMSO-d6) δ: 8.15 (dd, J = 8.1, 1.9 Hz, 1H), 8.11 (dd, J = 8.1, 1.9 Hz, 1H), 3.61 (q, J = 7.3 Hz, 2H), 2.37 (s, 3H). LC-MS: C6H7FN2 [M] + Calculated mass of : 126.1, measured value: 127.5 [M+1].

[0457] Step - 2: Preparation of 6-bromo-5-fluoro-2-methyl-pyridin-3-amine

[0458] To a stirred solution of 5-fluoro-2-methyl-pyridin-3-amine (9 g, 71.35 mmol) in CH2Cl2 (120 mL) at 0 °C was added N-bromosuccinimide (12.7 g, 71.35 mmol). The resulting reaction mixture was stirred at the same temperature for 10 min. After completion of the reaction, the reaction mixture was poured into water and extracted with CH2Cl2. The organic layer was washed with a saturated aqueous solution of sodium thiosulfate, the separated organic layer was dried, and concentrated to obtain a crude product. The crude product was purified by column chromatography to obtain 6-bromo-5-fluoro-2-methyl-pyridin-3-amine (9 g, 60% yield). 1 1H NMR (500 MHz, DMSO-d6) δ: 8.11 (dd, J = 8.1, 1.9 Hz, 1H), 3.61 (q, J = 7.3 Hz, 2H), 2.37 (s, 3H). LC-MS: C6H6BrFN2 [M] + Calculated mass of : 205, measured value: 207 [M+2].

[0459] Step - 3: Preparation of 1-(5-amino-3-fluoro-6-methyl-2-pyridyl)ethanone

[0460] A stirred solution of 6-bromo-5-fluoro-2-methyl-pyridin-3-amine (9 g, 2.03 mmol) and tributyl(1-ethoxyvinyl)tin (23.78 mL, 2.03 mmol) in toluene (10V, 100 mL) was degassed under N2 atmosphere for 10 min and then tetrakis-triphenylphosphine-palladium (2.53 g, 32.19 mmol) was added. The resulting reaction mixture was heated to 120 °C for 6 - 7 h. After completion of the reaction mixture, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to obtain a crude product. The crude product was purified by column chromatography to obtain 1-(5-amino-3-fluoro-6-methyl-2-pyridyl)ethanone (5 g, 50% yield). 11H NMR (500 MHz, DMSO-d6) δ: 8.11 (dd, J = 8.1, 1.9 Hz, 1H), 3.61 (q, J = 7.3 Hz, 2H), 2.37 (s, 3H), 1.15 - 1.08 (m, 3H). LC-MS: C8H9FN2O [M] + Calculated mass for: 168, found: 168.1.

[0461] Step - 4: Preparation of 1-(5-bromo-3-fluoro-6-methyl-2-pyridyl)ethanone

[0462] To a stirred solution of 1-(5-amino-3-fluoro-6-methyl-2-pyridyl)ethanone (4.2 g, 24.97 mmol) in ACN (50 mL) at 0 °C was added Cu(I)Br (3.58 g, 24.97 mmol) and isoamyl nitrite (4.38 g, 37.46 mmol). The resulting reaction mixture was stirred at the same temperature for 10 minutes and then at 20 °C to 25 °C for 1 h. After completion of the reaction, the reaction mixture was filtered through a pad of diatomaceous earth, the filtrate was poured into H2O and extracted. The organic layer was separated, dried and concentrated to give a crude product. The crude product was purified by column chromatography to give 1-(5-bromo-3-fluoro-6-methyl-2-pyridyl)ethanone (2.5 g, 40% yield). 1 1H NMR (500 MHz, DMSO-d6) δ: 8.11 (dd, J = 8.1, 1.9 Hz, 1H), 2.37 (s, 3H), 1.15 - 1.08 (m, 3H). LC-MS: C8H7BrFNO [M] + Calculated mass for: 232, found: 234 [M+2].[[]END]

[0463] Step 5: Preparation of 1-[3-fluoro-5-(4-fluorophenyl)-6-methyl-2-pyridyl]ethanone

[0464] A stirred solution of 1-(5-bromo-3-fluoro-6-methyl-2-pyridyl)ethanone (1.5 g, 6.46 mmol), (4-fluorophenyl)boronic acid (1.35 g, 9.69 mmol) and K2CO3 (1.78 g, 12.92 mmol) in 1,4-dioxane (10 mL) and water (2 mL) was degassed for 15 min under a N2 atmosphere, and then a complex of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) with DCM (0.373 g, 0.323 mmol) was added. The resulting reaction mixture was heated to 120 °C for 6 h. After completion of the reaction, the reaction mixture was poured into water and extracted. The organic layer was separated, dried and concentrated to give a crude product. The crude product was purified by column chromatography to give 1-[3-fluoro-5-(4-fluorophenyl)-6-methyl-2-pyridyl]ethanone (0.9 g, 66% yield). 1 H NMR (300 MHz, chloroform-d) δ 8.15 (s, 1H), 7.46 - 7.05 (m, 4H), 2.63 (s, 3H), 1.53 (s, 3H). LC-MS: C 14 H 11 F2NO[M] + Calculated mass for: 247.2, found 248.1 [M+1].

[0465] Step - 6: Preparation of 1-[3-ethylsulfonyl-5-(4-fluorophenyl)-6-methyl-2-pyridyl]ethanone

[0466] To a stirred solution of 1-[3-fluoro-5-(4-fluorophenyl)-6-methyl-2-pyridyl]ethanone (0.8 g, 3.39 mmol) and sodium ethanesulfonate (0.898 g, 6.79 mmol) in dimethylacetamide (10 mL). The resulting reaction mixture was heated to 120 °C for 2 h. After completion of the reaction, the reaction mixture was diluted with water and extracted. The organic layer was separated, dried and concentrated to give a crude product. The crude product was purified by column chromatography to give 1-[3-ethylsulfonyl-5-(4-fluorophenyl)-6-methyl-2-pyridyl]ethanone as a pale yellow solid (0.88 g, 95% yield). 1 H NMR (300 MHz, chloroform-d) δ 8.15 (s, 1H), 7.46 - 7.05 (m, 4H), 3.59 (q, J = 7.5 Hz, 2H), 2.63 (s, 3H), 1.53 (s, 3H), 1.36 (t, J = 7.5 Hz, 3H). LC-MS: C 16 H 16 FNO3S[M] + Calculated mass for: 321.3, found 322.1 [M+1].

[0467] Step - 7: Preparation of 2 - Bromo - 1 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] ethanone

[0468] To a stirred solution of 1 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] ethanone (0.9 g, 3.39 mmol) and pyridinium perbromide (0.94 g, 6.79 mmol) in dioxane (10 mL). The resulting reaction mixture was heated to 90 °C for 1.5 h. After completion of the reaction, the reaction mixture was diluted with ice - cold water (100 mL) and extracted. The organic layer was separated, dried and concentrated to give the crude material. The crude material was purified by column chromatography to give 2 - Bromo - 1 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] ethanone as a pale yellow solid (0.74 g, 60% yield). 1 1H NMR (300 MHz, chloroform - d) δ 8.15 (s, 1H), 7.46 - 7.05 (m, 4H), 4.96 (s, 2H), 3.59 (q, J = 7.5 Hz, 2H), 2.63 (s, 3H), 1.36 (t, J = 7.5 Hz, 3H). LC - MS: C 16 H 15 BrFNO3S [M] + Calculated mass for: 400.2, Found: 402.0 [M + 2].

[0469] Step - 8: Preparation of 7 - Chloro - 6 - cyclopropyl - 2 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] imidazo[1,2 - c] pyrimidin - 5 - one

[0470] To a stirred solution of 4 - amino - 6 - chloro - 1 - cyclopropyl - pyrimidin - 2 - one (0.4 g, 2.155 mmol) in tert - butanol (2 mL) was added 2 - Bromo - 1 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] ethanone (1.03 g, 2.58 mmol). Molecular sieves were added to the above reaction mixture (0.1 g) and the resulting reaction mixture was heated to 100 °C for 24 h. After completion of the reaction, the above reaction mixture was filtered through a bed of diatomaceous earth, the filtrate was collected and concentrated under reduced pressure to give the crude material, which was purified by column chromatography to give 7 - Chloro - 6 - cyclopropyl - 2 - [3 - ethylsulfonyl - 5 - (4 - fluorophenyl) - 6 - methyl - 2 - pyridyl] imidazo[1,2 - c] pyrimidin - 5 - one as a yellow solid (0.15 g, 30% yield). 1HNMR (300 MHz, DMSO-d6) δ 8.11 (d, J = 8.9 Hz, 2H), 7.61 (dd, J = 8.5, 5.5 Hz, 2H), 7.39 (t, J = 8.8 Hz, 2H), 7.12 (s, 1H), 4.01 (q, J = 7.4 Hz, 2H), 2.58 (s, 3H), 1.22 (m, 6H), 1.06 (s, 2H). LC-MS: C 23 H 20 ClFN4O3S [M] + Calculated mass for: 486.9, found: 487.1.

[0471] By appropriately changing the starting materials or their intermediates, the procedures described in the above preparation examples are used to obtain additional compounds of formula I.A.1 with their physical data listed in Table B.

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490] B. Biological Examples

[0491] The activity of the compounds of formula (I) according to the invention can be demonstrated and evaluated in the biological tests described below. Unless otherwise stated, the test solutions are prepared as follows: The active compound is dissolved in a 1:1 (v / v) mixture of distilled water:acetone at the desired concentration. The test solutions are prepared on the day of use. Test solutions at concentrations of 2500 ppm, 800 ppm and 300 ppm (wt / vol) are generally prepared.

[0492] B.1 Boll weevil

[0493] To evaluate the control of the boll weevil, the test unit consists of a 96-well microtiter plate containing insect feed and 5 - 10 boll weevil eggs. The compounds are formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds are sprayed onto the insect feed at 5 μl each using a customized microatomizer, and repeated twice. After application, the microtiter plate is incubated at about 25 °C ± 1 °C and about 75% ± 5% relative humidity for 5 days. Then, the mortality of the eggs and larvae is visually evaluated. In this test, compared with the untreated control, Compounds I.1, I.2, I.3, I.4, I.5, I.6, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.15, I.16, I.17, I.18, I.19, I.20, I.21, I.22, I.25, I.26, I.27, I.28, I.29, I.32, I.33, I.46, I.47, I.48, I.49, I.50 showed a mortality rate of over 75% at 800 ppm, respectively.

[0494] B.2 Tobacco budworm

[0495] To evaluate the control of the tobacco budworm (Heliothis virescens), the test unit consisted of 96-well microtiter plates containing insect diet and 15 - 25 eggs of Heliothis virescens. Compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were sprayed onto the insect diet at 10 μl using a custom-made microatomizer, and repeated twice. After application, the microtiter plates were incubated at approximately 28 °C ± 1 °C and approximately 80% ± 5% relative humidity for 5 days. Then, the egg and larval mortalities were visually evaluated. In this test, compared with the untreated control, Compounds I.1, I.4, I.5, I.6, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.15, I.16, I.17, I.18, I.19, I.20, I.21, I.22, I.23, I.25, I.26, I.27, I.28, I.29, I.30, I.32, I.36, I.37, I.47, I.48, I.49, I.50 showed mortalities of over 75% at 800 ppm, respectively.

[0496] B.3 Green Peach Aphid (Myzus persicae)

[0497] To evaluate the control of the green peach aphid (Myzus persicae) by a systematic method, the test device consisted of 96-well microtiter plates containing liquid artificial diet under an artificial membrane. Compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO. Different concentrations of the formulated compounds were pipetted onto the aphid diet, and repeated twice. After application, 5 - 8 adult aphids were placed on the artificial membrane in the microtiter plate wells. Then, the aphids were allowed to suck the treated aphid diet and incubated at approximately 23 °C ± 1 °C and approximately 50% ± 5% relative humidity for 3 days. Then, the aphid mortality and fecundity were visually evaluated. In this test, compared with the untreated control, Compounds I.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.10, I.11, I.12, I.13, I.14, I.16, I.17, I.18, I.19, I.20, I.21, I.25, I.26, I.27, I.28, I.29, I.31, I.32, I.33, I.36, I.37, I.46, I.47, I.48, I.49 showed mortalities of over 75% at 800 ppm, respectively.

[0498] B.4 Diamond back moth (Plutella xylostella)

[0499] The active compound was dissolved at the desired concentration in a 1:1 (v / v) mixture of distilled water:acetone. A surfactant (Kinetic) was added at a rate of 0.01% (v / v). The test solution was prepared on the day of use. Cabbage leaves (60 mm diameter) were dipped into the test solution and air-dried. The treated leaves were placed in Petri dishes lined with moist filter paper and inoculated with ten 3rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damage was also recorded using a 0 - 100% scale. In this test, compared to the untreated control, Compounds I.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.15, I.16, I.17, I.18, I.19, I.20, I.21, I.22, I.23, I.25, I.26, I.27, I.28, I.29, I.30, I.31, I.32, I.33, I.36, I.37, I.45, I.46, I.47, I.48, I.49, I.50 showed mortality of over 75% at 800 ppm respectively.

[0500] B.5 Subtropical armyworm (Spodoptera eridania), 2nd instar larvae

[0501] The active compound was formulated into a 10,000 ppm solution supplied in tubes in 100% cyclohexanone by a Tecan liquid handler. This 10,000 ppm solution was serially diluted in 100% cyclohexanone to prepare intermediate solutions. These were used as stock solutions and were made into final dilutions in 50% acetone:50% water (v / v) in 10 or 20 ml glass vials by Tecan. Nonionic surfactant It is included in the solution at a volume of 0.01% (v / v). Then the vial is inserted into an automatic electrostatic sprayer equipped with an atomizing nozzle for application to plants / insects. Two lima bean plants (variety Sieva) are planted in pots and selected for treatment at the first true leaf stage. The test solution is sprayed onto the leaf surface by an automatic electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants are dried in the sprayer fume hood and then removed from the sprayer. Each pot is placed in a perforated plastic bag with a zip closure. Ten to eleven armyworm larvae are placed in the bag and the bag is zipped closed. The test plants are kept in a growth chamber at about 25 °C and about 20%-40% relative humidity for 4 days, avoiding direct exposure to fluorescence (14:10 light:dark photoperiod) to prevent heat from being trapped inside the bag. Mortality and feeding reduction are evaluated 4 days after treatment compared to untreated control plants. In this test, compared to the untreated control, Compounds I.1, I.2, I.3, I.4, I.5, I.6, I.7, I.8, I.9, I.10, I.11, I.12, I.13, I.14, I.15, I.16, I.17, I.18, I.19, I.20, I.21, I.22, I.25, I.26, I.27, I.28, I.29, I.30, I.31, I.32, I.34, I.35, I.36, I.37, I.38, I.39, I.40, I.41, I-44, I.45, I.46, I.47, I.48, I.49, I.50 showed a mortality rate of over 75% at 300 ppm.

[0502] Comparative data:

[0503]

[0504] The comparative data show that despite the small structural differences (in this case, Cl / CF3), the compounds of the present application have significantly better activity.

Claims

1. A compound of formula (I), wherein, rings A and B are fully unsaturated; Y is C═X, where X is O; E is N(R 3 )); Q is N, N(R 5 ), or CH; G is phenyl or pyridyl; W is S, S(O), S(O)2, S(O)(NR W ), S(O)(NH); R 1 is a halogen; R 3 、R 5 independently is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, which are unsubstituted or halogenated; Each R 7 is independently H, halogen, OH, CN; C1-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, these groups being unsubstituted or halogenated; A saturated, partially unsaturated or fully unsaturated heterocycle or ring system having 3 to 12 ring members, wherein the heterocycle or ring system contains one or more identical or different heteroatoms O, N, or S and is unsubstituted or substituted by one or more R H groups; phenyl, which is unsubstituted or substituted by one or more R J substituted; OR K ; -C(CN)(CH3)2, or 1-cyanocyclopropyl; Each R H independently is halogen, CN; C1-C3-alkyl, C1-C3-haloalkyl; Each R J independently is halogen, CN; C1-C6-alkyl, C1-C6-alkoxy, these groups being unsubstituted or halogenated; or in the case where two adjacent substituents R J are C1-C6-alkoxy, these substituents form an alkyl bridge between the two oxygens, which is unsubstituted or halogenated; Each R K is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, where these groups are unsubstituted or substituted by one or more identical or different substituents selected from halogen and CN; Each R W independently is C1-C4-alkyl, or cyclopropyl; if G is phenyl, the subscript n is 1, 2, or 3, or 4, or if G is pyridyl, the subscript n is 1, 2, or 3; and its N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts.

2. The compound of formula (I) according to claim 1, wherein, The compound of formula (I) is a compound of formula (I.A); wherein all variables have the meanings as defined for formula (I).

3. The compound of formula (I.A) according to claim 2, wherein, R 3 is a C1-C3-alkyl group or a C3-C6-cycloalkyl group, where these groups are unsubstituted or halogenated.

4. A compound of formula (I) according to any one of claims 1 to 3, wherein, G is 2-pyridyl.

5. The compound of formula (I) according to any one of claims 1 to 4, wherein, R W is a C1-C3-alkyl group.

6. A compound of formula (I) according to any one of claims 1 to 5, wherein, the subscript n is 1 or 2.

7. A compound of formula (I) according to any one of claims 1 to 6, wherein, R 7 Yes Halogen; C1-C3-alkyl, cyclopropyl; a 6- to 9-membered saturated, partially unsaturated or fully unsaturated heterocycle or ring system, wherein said heterocycle or ring system contains one or more identical or different heteroatoms O or N and is unsubstituted or substituted by one or more substituents selected from halogen, CN, C1-C3-alkyl, and C1-C3-haloalkyl; phenyl, which is unsubstituted or substituted by one or more R J substituted; or OR K , wherein R K is a C1-C3-alkyl which is unsubstituted or substituted by CN.

8. A compound of formula (I) according to any one of claims 1 to 7, wherein, R 7 Selected from -C(CN)(CH3)2 and 1-cyanocyclopropyl.

9. A pesticidal composition comprising a compound of formula (I) according to any one of claims 1 to 8, its N-oxide or an agriculturally acceptable salt and an additional pesticidal ingredient.

10. Use of a compound of formula (I) according to any one of claims 1 to 8 as an agrochemical pesticidal agent.

11. A method for combating or controlling invertebrate pests, which method comprises bringing the pests or their food supply, habitat or breeding ground into contact with a pesticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 8 or a composition according to claim 9.

12. A method for protecting growing plants from infestation or infection by invertebrate pests, which method comprises bringing the plants or the soil or water in which the plants are growing into contact with a pesticidally effective amount of at least one compound of formula (I) according to any one of claims 1 to 8 or a composition according to claim 9.

13. A seed comprising a compound of formula (I) according to any one of claims 1 to 8 or a composition according to claim 9 in an amount of 0.1 g to 10 kg per 100 kg of seeds.

14. Use of a compound of formula (I) according to any one of claims 1 to 8 or a composition according to claim 9 for protecting growing plants from infestation or infection by invertebrate pests.

15. A method for treating or protecting an animal against infestation or infection by invertebrate pests, the method comprising contacting the animal with a pest - killing effective amount of a compound of formula (I) according to any one of claims 1 to 8 or a composition according to claim 9.

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