Heterocyclic compounds for combating invertebrate pests

Abstract

The invention relates to heterocyclic compounds of formula I [Formula should be inserted here] wherein the variables have the meanings as defined in the specification, to compositions comprising them, to active compound combinations comprising them, and to their use for protecting growing plants and animals from attack or infestation by invertebrate pests, furthermore, to seed comprising such compounds.

Description

[0001] 241142

[0002] 1

[0003] Heterocyclic compounds for combating invertebrate pests

[0004] Description

[0005] The invention relates to heterocyclic compounds of formula I

[0006]

[0007] wherein

[0008] R1ais Ci-C4-alkoxy, Ci-C4-haloalkoxy or halogen;

[0009] R1bis H or halogen;

[0010] R2is halogen; and

[0011] the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

[0012] The invention also provides an agricultural composition comprising at least one compound of formula I, a stereoisomer thereof and / or an agriculturally acceptable salt thereof and at least one liquid and / or solid carrier, especially at least one inert liquid and / or solid agriculturally acceptable carrier.

[0013] The invention also provides a veterinary composition comprising at least one compound of formula I, a stereoisomer thereof and / or a veterinarily acceptable salt thereof and at least one liquid and / or solid carrier, especially at least one inert veterinarily liquid and / or solid acceptable carrier. The invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein.

[0014] The present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and / or an agriculturally acceptable salt thereof.

[0015] The invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of formula I or a veterinarily acceptable salt thereof. Bringing the animal in contact with the compound I, its salt orthe veterinary composition of the invention means applying or administering it to the animal.

[0016] WO 2014 / 158639, WO 2014 / 158641 and WO 2014 / 163932 describe structurally closely related compounds. These compounds are mentioned to be process intermediates and lack a substitution on the phenyl ring adjacent to the nitro group.

[0017] There remains a need for highly effective and versatile agents for combating invertebrate pests. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control pests, such as insects.241142

[0018] 2

[0019] It has been found that these objectives can be achieved by compounds of formula I as depicted and defined below, and by their stereoisomers, salts, tautomers and N-oxides, in particular their agriculturally acceptable salts.

[0020] Compounds of formula I can be obtained from Compounds III via reaction with compound II.

[0021]

[0022] This transformation is usually carried out at temperatures of from -20°C to 110°C, preferably from 0°C to 50°C, in an inert solvent, in the presence of a base [cf. WO2014163932], Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, and chlorobenzene, ethers such as diethylether, diisopropylether, tert. -butylmethylether (MTBE), dioxane, anisole, and tetrahydrofurane (THF), alcohols such as methanol (MeOH), ethanol (EtOH), n-propanol, isopropanol, n-butanol, and tert.-butanol, moreover dimethyl sulphoxide (DMSO), dimethyl formamide (DMF), and dimethylacetamide (DMA), preferably aromatic hydrocarbons such as toluene. It is also possible to use mixtures of the solvents mentioned.

[0023] Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to pyridine. The bases are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent. The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of III, based on II.

[0024] Compounds III can be obtained from Compound IV via an alcohol addition reaction.

[0025]

[0026] This transformation is usually carried out at temperatures of from -20°C to 110°C, preferably from 0°C to 50°C, in an inert solvent, in the presence of an acid [cf. WO2014163932], Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and petrol ether, aromatic hydrocarbons such as toluene, o-, m-, and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform, and chlorobenzene, ethers such as diethylether, diisopropylether, tert. -butylmethylether (MTBE), dioxane, anisole, and tetrahydrofurane (THF), alcohols such as methanol (MeOH), ethanol (EtOH), n-propanol, isopropanol, n-butanol, and tert.-butanol, moreover dimethyl sulphoxide (DMSO), dimethyl formamide (DMF), and dimethylacetamide (DMA), preferably alcohols such as methanol (MeOH) and ethanol (EtOH). It is also possible to use mixtures of the solvents mentioned.241142

[0027] 3

[0028] Suitable acids and acidic catalysts are in general inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulphuric acid und perchloric acid, Lewis acids, such as boron tri fluoride, aluminium tri chloride, iron III chloride, tin IV chloride, titanium IV chloride and zinc II chloride, moreover organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluene sulphonic acid, benzene sulphonic acid, camphor sulphonic acid, citric acid, and trifluoro acetic acid. The acids are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess or, if appropriate, as solvent.

[0029] The starting materials are generally reacted with one another in equimolar amounts. In terms of yield, it may be advantageous to employ an excess of ethanol, based on IV.

[0030] The starting materials required for preparing the compounds I are commercially available or known from the literature [cf. Su, Y.; Sun, X.; Wu, G.; Jiao, N., Angew. Chem., Int. Ed. (2013), 52(37), 9808-9812 and Dong, Y.; Breit, B., Org. Lett. (2021), 23(17), 6765-6769] or can be prepared in accordance with the literature cited.

[0031] The reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are purified or freed from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

[0032] If individual compounds I cannot be obtained by the routes described above, they can be prepared by derivatization of other compounds I.

[0033] However, if the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (for example under the action of light, acids or bases). Such conversions may also take place after use, for example in the treatment of plants in the treated plant, or in the harmful fungus I invertebrate pest to be controlled.

[0034] The compounds of formula I may exist in different geometric or optical isomers ortautomeric forms. This invention covers all such isomers and tautomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.

[0035] The compounds according to the invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention relates to amorphous and crystalline compounds according to the invention, mixtures of different crystal line states of the respective compounds according to the invention, as well as amorphous or crystalline salts thereof.

[0036] The organic moieties groups mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members. The prefix Cn-Cm indicates in each case the possible number of carbon atoms in the group.

[0037] The term “partially or fully substituted” by a radical means that in general the group is substituted with same or different radicals.

[0038] The term “halogen” denotes in each case fluorine, bromine, chlorine, or iodine, in particular fluorine, chlorine, or bromine.

[0039] The term "alkyl" as used herein and in the alkyl moieties of alkylamino, alkylcarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl and alkoxyalkyl denotes in each case a straight-chain or branched241142

[0040] 4

[0041] alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, more preferably from 1 to 3 carbon atoms. Examples of an alkyl group are methyl (Me), ethyl (Et), n-propyl (n-Pr), iso-propyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 , 1 -dimethyl-propyl, 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-di-methylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1,2,2-trime-thylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

[0042] The term "haloalkyl" as used herein and in the haloalkyl moieties of haloalkylcarbonyl, haloalkoxycarbonyl, haloalkylthio, haloalkylsulfonyl, haloalkylsulfinyl, haloalkoxy and haloalkoxy-alkyl, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from Ci-C4-haloalkyl, more preferably from Ci-C3-haloalkyl or Ci-C2-haloalkyl, in particular from Ci-C2-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2 difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.

[0043] The term "alkoxy" as used herein denotes in each case a straight-chain or branched alkyl group which is bonded via an oxygen atom and has usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert. -butyloxy, and the like.

[0044] The term "alkoxyalkyl" as used herein refers to alkyl usually comprising 1 to 10, frequently 1 to 4, preferably 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are CH2OCH3, CH2-OC2H5, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.

[0045] The term "haloalkoxy" as used herein denotes in each case a straight-chain or branched alkoxy group having from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. Preferred haloalkoxy moieties include Ci-C4-haloal-koxy, in particular Ci-C2-fluoroalkoxy, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, 1 fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoro-ethoxy, 2,2dichloro-2-fluorethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and the like.

[0046] The term "alkylthio" (alkylsulfanyl: alkyl-S-) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms

[0047] (= Ci-C4-alkylthio), more preferably 1 to 3 carbon atoms, which is attached via a sulfur atom. The term "haloalkylthio" as used herein refers to an alkylthio group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine. The term "alkylsulfinyl" (alkylsulfoxyl: Ci-C6-alkyl-S(O)-), as used herein refers to a straightchain or branched saturated alkyl group (as mentioned above) having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkylsulfinyl), more preferably 1 to 3 carbon atoms bonded through the sulfur atom of the sulfinyl group at any position in the alkyl group.241142

[0048] 5

[0049] The term "haloalkylsulfinyl" as used herein refers to an alkylsulfinyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine.

[0050] The term "alkylsulfonyl" (alkyl-S(O)2-) as used herein refers to a straight-chain or branched saturated alkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms (= Ci-C4-alkyl-sulfonyl), preferably 1 to 3 carbon atoms, which is bonded via the sulfur atom of the sulfonyl group at any position in the alkyl group.

[0051] The term "haloalkylsulfonyl" as used herein refers to an alkylsulfonyl group as mentioned above wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine.

[0052] The term "alkylcarbonyl" refers to an alkyl group as defined above, which is bonded via the carbon atom of a carbonyl group (C=O) to the remainder of the molecule.

[0053] The term "haloalkylcarbonyl" refers to an alkylcarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine. The term "alkoxycarbonyl" refers to an alkylcarbonyl group as defined above, which is bonded via an oxygen atom to the remainder of the molecule.

[0054] The term "haloalkoxycarbonyl” refers to an alkoxycarbonyl group as mentioned above, wherein the hydrogen atoms are partially or fully substituted by fluorine, chlorine, bromine and / or iodine. The term "alkenyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. vinyl, allyl (2-propen-1-yl), 1-propen-1-yl, 2 propen-2-yl, methallyl (2-methylprop-2-en-1-yl), 2-buten-1-yl, 3-buten-1-yl, 2-penten-1-yl, 3-penten-1-yl, 4-penten-1-yl, 1-methylbut-2-en-1-yl, 2-ethylprop-2-en-1-yl and the like.

[0055] The term "haloalkenyl" as used herein refers to an alkenyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.

[0056] The term "alkynyl" as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 10, frequently 2 to 6, preferably 2 to 4 carbon atoms, e.g. ethynyl, pro-par-gyl (2-propyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl, 4-pentyn-1-yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl and the like.

[0057] The term "haloalkynyl" as used herein refers to an alkynyl group as defined above, wherein the hydrogen atoms are partially or totally replaced with halogen atoms.

[0058] The term "cycloalkyl" as used herein and in the cycloalkyl moieties of cycloalkoxy and cyclo-al-kylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl (c-C3H5), cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyl and cy-clo-hexyl.

[0059] The term "halocycloalkyl" as used herein and in the halocycloalkyl moieties of halocycloalkoxy and halocycloalkylthio denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 C atoms or 3 to 6 C atoms, wherein at least one, e.g. 1 , 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-flu-orocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1 ,2,2-trifluorocyclopropyl, 2,2,3,3-tetra-fluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1 ,2,2-trichlo-rocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-,241142

[0060] 6

[0061] 3,4-, 2,5-difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlo-rocyclopentyl and the like.

[0062] The term “halocycloalkenyl” as used herein and in the halocycloalkenyl moieties of halocycloal-kenyloxy and halocycloalkenylthio denotes in each case a monocyclic singly unsaturated nonaromatic radical having usually from 3 to 10, e.g. 3 or 4 or from 5 to 10 carbon atoms, preferably from 3- to 8 carbon atoms, wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms, are replaced by halogen, in particular by fluorine or chlorine. Examples are 3,3-difluorocyclopropen-1-yl and 3,3-dichlorocyclopropen-1-yl.

[0063] The term "cycloalkenylalkyl" refers to a cycloalkenyl group as defined above which is bonded via an alkyl group, such as a Ci-C5-alkyl group or a Ci-C4-alkyl group, in particular a methyl group (= cycloalkenylmethyl), to the remainder of the molecule.

[0064] The term “carbocycle” or “carbocyclyl” includes in general a 3- to 12-membered, preferably a 3-to 8-membered or a 5- to 8-membered, more preferably a 5- or 6-membered monocyclic, nonaromatic ring comprising 3 to 12, preferably 3 to 8 or 5 to 8, more preferably 5 or 6 carbon atoms. Preferably, the term “carbocycle” covers cycloalkyl and cycloalkenyl groups as defined above.

[0065] The term “heterocycle” or "heterocyclyl" includes in general 3- to 12-membered, preferably 3- to 6-membered, in particular 6-membered monocyclic heterocyclic non-aromatic radicals. The heterocyclic non-aromatic radicals usually comprise 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3 hetero-,at-oms selected from N, O and S as ring members, wherein S-atoms as ring members may be present as S, SO or SO2. Examples of 5- or 6-membered heterocyclic radicals comprise saturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxo-'thiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, ox-athiolanyl, piperidinyl, piperazinyl, pyranyl, di hydro pyranyl, tetrahydropyranyl, 1,3- and 1,4-diox-anyl, thiopyranyl, S. oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopy-ranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotet-rahydrothiopyranyl, morpholinyl, thiomorpholinyl, S-oxothiomorpholinyl, S-dioxothiomorpholinyl, thiazinyl and the like. Examples for heterocyclic ring also comprising 1 or 2 carbonyl groups as ring members comprise pyrrolidin-2-onyl, pyrrolidin-2,5-dionyl, imidazolidin-2-onyl, oxazolidin-2-onyl, thiazolidin-2-only, and the like.

[0066] The term "hetaryl" includes monocyclic 5- or 6-membered heteroaromatic radicals comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S. N- or S-containing hetaryl groups may be present as positively charged onium, and form together with a neighbouring atom a mesoionic entity. Examples of 5- or 6 membered heteroaromatic radicals 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, oxa-zolyl, i.e. 2-, 3- or 5-oxazolyl, isoxazolyl, i.e. 3-, 4- or 5-isoxazolyl, thiazolyl, i.e. 2-, 3- or 5-thia-zolyl, 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, e.g. 2- or 5 [1 ,3,4]oxadiazolyl, 4- or 5-(1 ,2,3-oxa_'diazol)yl, 3- or 5-(1,2,4-oxadiazol)yl, 2- or 5 (1 ,3,4-thiadiazol)yl, thiadiazolyl, e.g. 2- or 5-(1 ,3,4-thia_,diazol)yl, 4-or 5 (1 ,2,3 thiadiazol)yl, 3- or 5-(1 ,2,4-thiadiazol)yl, triazolyl, e.g. 1 H-, 2H- or 3H 1 ,2,3 triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or4H-1,2,4-triazolyl and tetrazolyl, i.e. 1H- or2H tetrazolyl. The241142

[0067] 7

[0068] term "hetaryl" also includes bicyclic 8 to 10-membered heteroaromatic radicals comprising as ring members 1 , 2 or 3 heteroatoms selected from N, O and S, wherein a 5- or 6-membered heteroaromatic ring is fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical. Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzo-'thienyl, indolyl, ind-'azolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, iso-chinolinyl, purinyl, 1 ,8-naphthyridyl, pteridyl, pyrido[3,2 d]pyrimidyl or pyridoimidazolyl and the like. These fused hetaryl radicals may be bonded to the remainder of the molecule via any ring atom of 5- or 6-membered heteroaromatic ring or via a carbon atom of the fused phenyl moiety. The terms "heterocyclylalkyl" and "hetarylalkyl" refer to heterocyclyl or hetaryl, respectively, as defined above which are bonded via a Ci-C5-alkyl group or a Ci-C4-alkyl group, in particular a methyl group (= heterocyclylmethyl or hetarylmethyl, respectively), to the remainder of the molecule.

[0069] The term “arylalkyl” and "phenylalkyl" refer to aryl as defined above and phenyl, respectively, which are bonded via Ci-C5-alkyl group or a Ci-C4-alkyl group, in particular a methyl group (= arylmethyl or phenylmethyl), to the remainder of the molecule, examples including benzyl, 1-phenylethyl, 2-phenylethyl, 2-phenoxyethyl etc.

[0070] The terms “alkylene”, “cycloalkylene”, “heterocycloalkylene”, “alkenylene”, “cycloalkenylene”, “heterocycloalkenylene” and “alkynylene” refer to alkyl, cycloalkyl, heterocycloalkyl, alkenyl, cycloalkenyl, heterocycloalkenyl and alkynyl as defined above, respectively, which are bonded to the remainder of the molecule, via two atoms, preferably via two carbon atoms, of the respective group, so that they represent a linker between two moieties of the molecule.

[0071] It is understood that the various embodiments of compounds of formula I also include the N-ox-ide, stereoisomer, tautomer, agriculturally or veterinarily acceptable salt thereof.

[0072] In a particular embodiment, the variables of the compounds of the formula I have the following meanings, these meanings, both on their own and in combination with one another, being particular embodiments of the compounds of the formula I.

[0073] Embodiments and preferred compounds of the invention for use in pesticidal methods and for insecticidal application purposes are outlined in the following paragraphs.

[0074] With respect to the variables, embodiments of the intermediates correspond to those of the compounds of the formula I.

[0075] In various embodiments, R2is halogen, preferably R2is F, Cl or Br, further preferably R2is F. In various embodiments, R1bis H or halogen, preferably R1bis H, F, Cl or Br, further preferably R1bis H.

[0076] In various embodiments, R1ais OCF3or OCHF2, preferably R1ais OCF3.

[0077] In various embodiments, R1ais OCF3, R1bis H and R2is F.241142

[0078] In various embodiments, the compounds I are present in form of a mixture of the tautomeric com-pounds I, I.E and I.Z, in particular a mixture of I.E and I.Z.

[0079]

[0080] In various embodiments, the compound I is compound 1-1 or the N-oxide, tautomers, oragricul-turally or veterinarily acceptable salt thereof. Tautomeric forms of 1-1 include 1-1 A, 1-1 E and 1-1 Z.

[0081]

[0082] In various embodiments, the compounds 1-1 are present in form of a mixture of compounds I-1A, 1-1 E and 1-1 Z, in particular a mixture of 1-1 E and 1-1 Z.

[0083] In various embodiments, the compounds 1-1 are present in form hydrochloride salts.

[0084] One particular embodiment relates to a process for the preparation of a compound of formula I, wherein the process optionally comprises step i)

[0085] i) reaction of a compound of formula III with a compound of formula II in the presence of a base

[0086]

[0087] wherein the process optionally further comprises step ii)

[0088] ii) an alcohol addition reaction of compound IV in presence of an acid

[0089]

[0090] One particular embodiment relates to a process for the preparation of a pesticidal compound, mixture or formulation thereof, comprising a compound of formula I preferably as an intermediate compound. Further preferably, wherein the pesticidal compound, mixture or formulation thereof, is a fungicidal, herbicidal or insecticidal compound, further preferably wherein the insecticidal compound is compound X.241142

[0091] 9

[0092] One particular embodiment relates to a compound of formula I for use in a process of preparing a pesticidal compound, mixture or formulation thereof. Preferably, wherein the pesticidal compound, mixture or formulation thereof, is a fungicidal, herbicidal or insecticidal compound, further preferably wherein the insecticidal compound is compound X.

[0093] One particular embodiment relates to an agricultural or veterinary composition comprising at least one compound of formula I and at least one fungicidal, herbicidal or insecticidal compound, preferably at least one insecticidal compound, further preferably wherein the insecticidal compound is compound X. Preferred are weight ratios of the compound of formula I to the fungicidal, herbicidal or insecticidal compound of 1:100, 1:250, 1:500, 1:1000 or 1 :5000. Also preferred are weight ratios for such agricultural or veterinary compositions from 5000:1 to 1 :5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly from 10:1 to 1:10.

[0094] One particular embodiment relates to an agricultural or veterinary composition comprising at least one compound of formula I and at least one fungicidal, herbicidal and / or insecticidal compound, preferably wherein the weight ratios of the compound of formula I to the fungicidal, herbicidal or insecticidal compound is from 5000:1 to 1:5000, further preferably 1:100 to 1:1000, further preferably wherein the insecticidal compound is compound X.

[0095] As used herein, the term “compound(s) of the invention” or “compound(s) according to the invention” refers to the compound(s) of formula (I) as defined above, which are also referred to as “compound(s) of formula I” or “compound(s) I” or “formula I compound(s)”, and includes their salts, tautomers, stereoisomers, and N-oxides.

[0096] Mixtures

[0097] The invention also relates to a mixture of at least one compound of the invention with at least one mixing partner. Preferred are binary mixtures of one compound of the invention as component I with one mixing partner herein as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1:5000, preferably from 1000:1 to 1:1000, more preferably from 100:1 to 1:100, particularly from 10:1 to 1:10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

[0098] Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers. Preferred mixing partners are insecticides, nematicides, and fungicides.

[0099] The following list M of pesticides, grouped according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC), together with which the compounds of the invention can be used and with which potential synergistic effects might be produced, illustrates the possible combinations:

[0100] M.1 AChE inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycar-boxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, azinphos-ethyl,241142

[0101] 10

[0102] azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifosmethyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenam-iphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimi-phos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, sulfoxamyl, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

[0103] M.2. GABA-gated chloride channel antagonists: cyclodiene organochlorine compounds: endosulfan, chlordane; phenylpyrazoles: ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;

[0104] M.3 Sodium channel modulators: pyrethroids: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cy-permethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cy-phenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flu-cythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin.meto-fluthrin, momfluorothrin, epsilon-momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tet-ramethrin, tralomethrin, transfluthrin, vinylfluthrin; sodium channel modulators, e.g.: DDT, methoxychlor;

[0105] M.4 Nicotinic Acetylcholine Receptor competitive modulators: acetamiprid, clothianidin, cyclox-aprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, (2E-)-1-[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentyli-denehydrazinecarboximidamide; 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor; flupyradifurone; dicloromezo-tiaz, triflumezopyrim, fenmezoditiaz, flupyrimin, 1-[(2-chlorothiazol-5-yl)methyl]-3-(3,5-dimethyli-soxazol-4-yl)pyrido[1 ,2-a]pyrimidine-2, 4-dione, flupymezotiaz;

[0106] M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spineto-ram;

[0107] M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

[0108] M.7 Juvenile hormone mimics, such as hydroprene, kino-prene, methoprene; fenoxycarb, or pyriproxyfen;

[0109] M.8 miscellaneous multi-site inhibitors: CH3Br, other alkyl halides, chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0110] M.9 Chordotonal organ TRPV channel modulators: afidopyropen, pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin, etoxazole;

[0111] M.11 Microbial disruptors of insect midgut membranes: bacillus thuringiensis, bacillus sphaeri-cus, and insecticdal proteins they produce e.g.: bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki, bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;M.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron, organotin miticides, e.g.: azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

[0112] M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;

[0113] M.14 nAChR channel blockers: nereistoxin analogues bensultap, cartap hydrochloride, thio-cyclam, thiosultap-sodium;

[0114] M.15 Inhibitors of the chitin biosynthesis type 0, e.g.: bistrifluron, chlorfluazuron, difluben-zuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

[0115] M.16 Inhibitors of the chitin biosynthesis type 1: buprofezin;

[0116] M.17 Moulting disruptors: Dipteran, cyromazine;

[0117] M.18 Ecdyson receptor agonists, e.g.: methoxyfenozide, tebufenozide, halofenozide, fufeno-zide, chromafenozide;

[0118] M.19 Octopamin receptor agonists: amitraz;

[0119] M.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim; bifenazate;

[0120] M.21 METI acaricides and insecticides, e.g.: fenazaquin, fen pyroxi mate, pyrimidifen, pyrida-ben, tebufenpyrad, tolfenpyrad, rotenone;

[0121] M.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, N-(3-chloro-2-methyl-phenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-methylene]-hydra-zinecarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide;

[0122] M.23 Inhibitors of the of acetyl CoA carboxylase, e.g.: spirodiclofen, spiromesifen, spirotetramat; spiropidion; spirobudifen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-aza-dispiro[4.2.4.2]tetradec-11-en-10-one, spidoxamat;

[0123] M.24 Mitochondrial complex IV electron transport inhibitors: e.g. aluminium phosphide, calcium phosphide, zinc phosphide, cyanide;

[0124] M.25 Mitochondrial complex II electron transport inhibitors, e.g.: cyenopyrafen, cyflumetofen, cyetpyrafen, pyflubumide;

[0125] M.28 Ryanodine receptor-modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, fluben-diamide, fluchlordiniliprole, (R)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluorome-thyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid, (S)-3-chloro-N1-{2-methyl-4-[1 , 2,2, 2-tetrafluoro-1 -(trifluoromethyl) ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthal-amide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}ami-no)benzoyl]-1,2-dimethylhydrazine-carboxylate; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl-phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyra-zole-5-carboxamide; tetrachlorantraniliprole; tetraniliprole; tiorantraniliprole; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methyl-phenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; cyhalodiamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, pioxaniliprole; M.29: Chordotonal organ Modulators: flonicamid, flumetnicam;M.30: broflanilide; fluxametamide, isocycloseram, piperflanilide, cyproflanilide, isoflualanam, tri-oxyflanilide;

[0126] M.33 acynonapyr;

[0127] M.34 mitochondrial complex III electron transport inhibitors - Qi site: flometoquin;

[0128] M.35 RNA interference mediated target suppressors: Ledprona;

[0129] M.36 Chordotonal organ Modulators: dimpropyridaz;

[0130] M.37 vesicular acetylchloline transporter (VAChT) inhibitor: cybenzoxasulfyl, oxazosulfyl;

[0131] M.UN. Unknown mode of action: afoxolaner, azadirachtin, amidoflumet, benzoximate, bromopropylate, chinomethionat, cryolite, dicofol, flufenerim, fluensulfone, fluhexafon, fluopyram, flu-ralaner, metaldehyde, metoxadiazone, mivorilaner, modoflaner, piperonyl butoxide, pyridalyl, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-di-oxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hy-droxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfi-nyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, actives on basis of bacillus firmus (Vo-tivo, 1-1582); fluazaindolizine; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluorome-thyl)-propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cy-ano-5-[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)-propyl]phenyl]carbamoyl]phe-nyl]-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoro-methyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1, 2,2,2-tetrafluoro-1 -(trifluoromethyl) ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-ben-zamide;

[0132] 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-ni-tro-imidazo[1,2-a]pyridine; 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; tyclopyrazoflor; sarolaner, lotilaner; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-me-thyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1, 1,2,2, 2-pentafluoroethyl)-4-(trifluorome-thyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(tri-fluoromethyl)imid-azo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)im-idazo[4,5-b]pyridine; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pen-tafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide, N-[4-chloro-3-[(1-cyanocyclopro-pyl)carbamoyl]phenyl]-2-methyl-5-(1, 1,2,2, 2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-car-boxamide; benzpyrimoxan; tigolaner; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tet-rahydropyran-2-yl] N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(trifluorometh-oxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl] N-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl] N-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-iso-propylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydra-zono]thiazolidin-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1 -[4-(1 , 1 ,2,2,2-pentafluoroeth-oxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one, (2Z)-3-(2-iso-propylphenyl)-2-[(E)-[4-[1-[4-(1 ,1 ,2,2,2-pentafluoroethoxy)phenyl]-1 ,2,4-triazol-3-13 yl]phenyl]methylenehydrazono]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyri-din-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imid-azo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyri-dine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imid-azo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoro-methyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imid-azo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyra-zolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluorome-thyl)pyrrolidin-1-yl]phenyl]methyl]cyclopropanecarboxamide; sulfiflumin; flupentiofenox, N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-2-methylsulfonyl-propanamide, cyclobutrifluram; N-[4-chloro-3-[(1 -cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1 , 1 ,2,2,2-pentafluoro-ethyl)pyrazole-3-carboxamide, nicofluprole; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2h-indazol-5-yl]-1, 2, 4-triazolidine-3, 5-dione, indazapyroxamet, tiapyrachlor, N-cyclopropyl-5-[(5S)-5-(3,5-di-chloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)iso-quinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-Bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]di-oxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5-cyclopro-pyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole, Flupy-roxystrobin, 3,5-bis(trifluoromethyl)-N-[(1S)-1-[1-[6-(trifluoromethyl)-4-pyrimidinyl]-1H-1,2,4-tria-zol-5-yl]ethyl]-benzamide, 2-(3-ethylsulfonyl-2-pyridyl)-5-(2,2,3,3,3-pentafluoropropoxy)pyrazine, 2-[3-ethylsulfonyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imid-azo[4,5-b]pyridine, 9-(methoxymethyl)-5-(3-pyridyl)-2-oxa-5,6,9, 14-tetrazatricy-clo[8.4.0.0A{3,7}]tetradeca-1(10),3,6,11,13-pentaen-8-one, bisulfufen, 2-[5-[(E)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-1-methyl-imidazol-2-yl]-5-cyclopropyl-3-ethylsulfonyl-pyridine ;

[0133] Bentioflumin, Vadescana, (3Z)-1-[2-fluoro-4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]-3-[3-[5-methyl-2-(2,2,2-trifluoroethoxymethyl)phenyl]-4-oxo-1,3-thiazolidin-2-yli-dene]urea (compound X), 1-[6-(2,2-difluoro-8-oxo-[1,3]dioxolo[4,5-g]chromen-7-yl)-5-ethyl-sulfonyl-3-pyridyl]cyclopropanecarbonitrile, 2-chloro-N-[(1S)-2-ethyl-1-methyl-butyl]furan-3-car-boxamide, galquin, [5-cyclopropyl-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]-3-pyridyl]-ethyl-hydroxy-oxo-A6-sulfane, 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-[1 -(2,2,2-trifluoroethylcarbamoyl)cyclopropyl]benzamide, , 1 -[4-[5-ethylsulfonyl-1-methyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazol-2-yl]phe-nyl]cyclopropanecarbonitrile, 1-(1,2-dimethylpropyl)-5-methyl-N-prop-2-ynyl-N-(3-pyridyl)pyra-zole-4-carboxamide, 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]isoindolin-1-one.The commercially available compounds M listed above may be found in The Pesticide Manual, 18th Edition, C. MacBean, British Crop Protection Council (2018), or http: / / bcpcdata.com / pesti-cide-manual.html, http: / / www.alanwood.net / pesticides.

[0134] The active compounds described by IUPAC nomenclature are known from CN103814937; WO2013 / 003977, W02007 / 101369, WO2018 / 177970, CN10171577, CN102126994, W02007 / 101540, W02007 / 043677, WO2011 / 085575, W02008 / 134969, WO2012 / 034403, W02006 / 089633, W02008 / 067911 , W02006 / 043635, W02009 / 124707, WO2013 / 050317, WO2010 / 060379, WO2010 / 127926, WO2010 / 006713, WO2012 / 000896, W02007 / 101369, WO2012 / 143317, WO2015 / 038503, EP2910126, WO2015 / 059039, W02015 / 190316, WO2012 / 126766, W02009 / 102736, WO2013 / 116053, WO2018 / 052136, WO2015150252, W02020055955, WO2021158455, WO2013092350, WO201811111, EP3608311 , WO2019236274, WO2013092350, WO 2018052136, W02009102736, WO2016174049, WO2012126766, CN106554335, WO2017054524, CN105153113, W02022072650;

[0135] WO2018071327, W02022101502, WO2012158396, W02007079162, W02020013147, W02020097414, EP242081 , WO2023058748, WO2017065228, EP3428166, WO2021029308, W02022009058, WO2017067500, W02020090585, WO2017146226, W02021043115, WO2023016278, W02021011722, WO2024126388, WO2024137594, EP4389739, WO2016096584, WO2024120137, WO2024188755, CN115925576, WO2024087613,

[0136] CN 117770270, WO2025098876, W02009027393, WO2023160316, WO2019233321.

[0137] The following list of fungicides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:

[0138] A) Respiration (C)

[0139] complex III at Qosite (Qol, C3): azoxystrobin (A.1.1), bifemetstrobin (A.1.24), bifujunzhi (A.1.37), coumethoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestro- burin (A.1.5), famoxadone (A.1.21), fenamidone (A.1.23), fenaminstrobin (A.1.6), flufen- oxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metcyclofenstrobin (A.1.26), metominostrobin (A.1.11), metyltetraprole (A.1.25); member of MoA subgroup A), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), pyribencarb (A.1.19), pyriminostrobin (A.1.36), triclopyricarb (A.1.20), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-me- thyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- / V-methyl-acetamide (A.1.18), me- thyl- / V-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]- / V-methoxy-carbamate (A.1.22), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino- / V,3-dimethyl- pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino- A / ,3-dimethyl-pent-3-enamide (A.1.35), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)- 3-methoxy-acrylic acid methylester (A.1.38), methyl / V-[[5-[1-(2,6-difluoro-4-isopropylphenyl)- pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl / V-[[5-[1-(4-cyclopropyl-2,6-difluoro- phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl / V-[[5-[1 -(4-chloro-2,6-di- fluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate, methyl A / -[[5- [ 1 -[2,6-di-fluoro- 4-(trifluoromethyl)phenyl]pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate;

[0140] - complex III at Qi site (Qil, C4): cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-ben- zyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan- 7-yl]-2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4), florylpicoxamid (A.2.5),metarylpicoxamid (A.2.6);

[0141] - complex II (SDHI, C2): benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), cyclobutrifluram (A.3.24), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), inpyrfluxam (A.3.22), isofetamid (A.3.11), isoflucypram (A.3.31), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrapropoyne (A.3.23), pyraziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), fluindapyr (A.3.28), / V-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluorome- thyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2-methyl- phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), 2-(difluoromethyl)- / V-(1 ,1 ,3-tri- methyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)- / V-[(3R)-1 ,1 ,3-trime- thylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)- / V-(3-ethyl-1 ,1-dimethyl- indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)- / V-[(3R)-3-ethyl-1 ,1-dimethyl- indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)- / V-(1 ,1-dimethyl-3-propyl-in- dan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)- / V-[(3R)-1 ,1-dimethyl-3-propyl- indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)- / V-(3-isobutyl-1 ,1-dimethyl- indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)- / V-[(3R)-3-isobutyl-1 ,1-dime- thyl-indan-4-yl]pyridine-3-carboxamide (A.3.39);

[0142] - complex I NADH oxido-reductase (C1): diflumetorim (A.4.1);

[0143] - uncouplers (C5): binapacryl (A.4.2), dinobuton (A.4.3), dinocap (AAA), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7);

[0144] - inhibitors of ox. phosphorylation (C6): fentin salts, e.g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10);

[0145] - ATP transport: silthiofam (A.4.11);

[0146] - quinone inside and outside inhibitor stigmatellin binding type (QioSI; C8): ametoctradin (A.5.1);

[0147] B) Sterol biosynthesis (G)

[0148] - C14 demethylase (DMI, G1): triazoles: azaconazole (B.1.1), bitertanol (B.1.2), bromucona- zole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1.6), dinicona- zole-M (B.1.7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluoxytioconazole (B.1.33), flu- quinconazole (B.1.10), flusilazole (B.1.11), flutriafol (B.1.12), hexaconazole (B.1.13), imiben- conazole (B.1.14), ipconazole (B.1.15), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutra- zole (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), sime- conazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triad- imenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)- 1 , 1 -difluoro-3-(tetrazol-1 -yl)- 1 -[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]- 2-pyridyl]propan-2-ol (B.1.32), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1 ,2,4-triazol- 1-ylmethyl)cyclopentanol (B.1.43), 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy- 3-(1 ,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)-2-(tri- fluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)- 2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol (B.1.55), (2R)-2-[4-(4-chloro- phenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlo-16

[0149] rophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol, methyl 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate (B.1.56), 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid (B.1.57); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); pyrimidines, pyridines, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51),

[0150] [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

[0151] - delta14-reductase (G2): aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropidin (B.2.6), fenpropimorph (B.2.4), piperalin (B.2.7), spiroxamine (B.2.8), tridemorph (B.2.5);

[0152] - 3-keto reductase (G3): fenhexamid (B.3.1), fenpyrazamine (B.3.2);

[0153] - other: chlorphenomizole (B.4.1);

[0154] C) Nucleic acids metabolism (A)

[0155] - RNA polymerase I (A1): benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

[0156] - adenosine deaminase (A2): bupirimate (C.2.4), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2-(4-chloro- phenylmethoxy)pyrimidin-4-amine (C.2.8);

[0157] - DNA / RNA synthesis (A3): 5-fluorocytosine (C.2.5), hymexazole (C.2.1), octhilinone (C.2.2), - gyrase (A4): oxolinic acid (C.2.3);

[0158] - dihydroorotate dehydrogenase (DHODH; A5): ipflufenoquin (C.5.1), quinofumelin (C.5.2), feneptamidoquin (C.5.3), quinaminoprole (C.5.4);

[0159] D) Cytoskeleton and motor protein (B)

[0160] - tubulin polymerization (MBC; B1): benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), pyridachlometyl (D.1.6), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), / V-ethyl- 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), / V-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-propyl-bu- tanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy- / V-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl- / V-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- / V-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)- / V-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol- 3-amine (D.1.16), 4-(2-bromo-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1 / - / -py- razol-5-amine, 4-(2-chloro-4,6-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1 / - / -py- razol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-3-ethyl-1-methyl-1 / - / -py- razol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine, 4-(2-chloro-4-fluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1,3-dimethyl- 1 H-pyrazol-5-amine, 4-(2,4-difluorophenyl)- / V-(2-fluoro-6-nitrophenyl)-1 ,3-dimethyl-1 H-pyra- zol-5-amine;

[0161] - tubulin polymerization (B2): diethofencarb (D.2.1),

[0162] - tubulin polymersation (B3): ethaboxam (D.2.2), zoxamide (D.2.5);

[0163] - cell division (B4): pencycuron (D.2.3);

[0164] - spectrin-like proteins (B5): fluopicolide (D.2.4), fluopimomide (D.2.9);241142

[0165] 17

[0166] - actin / myosin / fimbrin function (B6): metrafenone (D.2.6), phenamacril (D.2.8), pyriofenone (D.2.7);

[0167] E) Amino acids and protein synthesis (D)

[0168] - methionine synthesis (D1): cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - ribosome, termination step (D2): blasticidin-S (E.2.1);

[0169] - ribosome initiation step (D3): kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3);

[0170] - ribosome initiation step (D4): streptomycin (E.2.5);

[0171] - ribosome elongation step (D5): mildiomycin (E.2.4), oxytetracyclin (E.2.6);

[0172] F) Signal transduction

[0173] - mechanism unknown (E1): proquinazid (F.2.2), quinoxyfen (F.2.1);

[0174] - MAP / histidine kinase os-2 (E2): fludioxonil (F.1.5);

[0175] - MAP / histidine kinase os-1 (E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4); G) Lipid synthesis or transport / membrane (F)

[0176] - methyl transferase (F2): edifenphos (G.1.1), iprobenfos (G.1.2), isoprothiolane (G.1.4); pyrazophos (G.1.3);

[0177] - cell peroxidation (F3): biphenyl (G.2.5), chloroneb (G.2.6), dicloran (G.2.1), etridiazole (G.2.7), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4);

[0178] - cell membrane permeability (F4): propamocarb (G.4.1);

[0179] - ergosterol binding (F8): natamycin;

[0180] - oxysterol binding protein (F9): fluoxapiprolin (G.5.3), oxathiapiprolin (G.5.1), 4-[1-[2-[3-(di- fluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]- / V-tetralin-1 -yl-pyri- dine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]- 4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine- 2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyra- zol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclo- propyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- / V-tetralin-1-yl-pyridine-2-carbox- amide (G.5.11), (1-(4-(4-(5-(2,6-dichlorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperi- din-1-yl)-2-((3-trifluoromethyl)pyrazin-2-yl)oxy)ethan-1-one, 1-(4-(4-(5-(2-chloro-6-fluoro- phenyl)-4,5-dihydroisoxazol-3-yl)thiazol-2-yl)piperidin-1-yl)-2-((3-trifluoromethyl)pyridin-2-yl)- oxy)ethan-1-one, tert-butyl 4-(4-(5-(2-bromo-6-fluorophenyl)-4,5-dihydroisoxazol-3-yl)thiazol- 2-yl)piperidin-1 -carboxylate, ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 H-pyrazol-1 -yl)acetyl)pi- peridin-4-yl)thiazol-4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfa- none, ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 / - / -pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol- 4-yl)-4,5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)dimethyl-A6-sulfanone,

[0181] ((2-(3-(2-(1 -(2-(3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4.5-dihydroisoxazo-5-yl)-3-chorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone,

[0182] ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4.5-dihydroisoxazo-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-A6-sulfanone,

[0183] ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl)acetyl)piperidin-4-yl)thiazol-4-yl)-241142

[0184] 18

[0185] 4.5-dihydroisoxazo-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-A6-sulfanone, ((3-fluoro- 2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1 / - / -pyrazol-1-yl)acetyl)piperidin-4-yl)thiazol-4-yl)- 4.5-dihydroisoxazo-5-yl)-phenyl)imino)dimethyl-A6-sulfanone;

[0186] H) Multi Site Activity (M)

[0187] - inorganics (M01): Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - dithiocarbamates and relatives: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9), zinc thiazole (H.2.10);

[0188] - organochlorine compounds (M04, M05, M06, M08): anilazine (H.3.1), captafol (H.3.3), captan (H.3.4), chlorothalonil (H.3.2), dichlofluanid (H.3.6), dichlorophen (H.3.7), folpet (H.3.5), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11);

[0189] - guanidines, quinones, quinoxalines, maleimides, thiocarbamates (M07, M09, M10, M11, M12): chinomethionat (H.4.13), dithianon (H.4.9), fluoroimide (H.4.11), guanidine (H.4.1), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), methasulfocarb (H.4.12), 2,6-dimethyl- 1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10),

[0190] I) Cell wall biosynthesis (H) and melanin synthesis in cell wall (I)

[0191] - chitin synthase (H4): polyoxin B (1.1.2);

[0192] - cellulose synthase (H5): benthiavalicarb (1.3.5), dimethomorph (1.3.1), flumorph (1.3.2), iprov- alicarb (1.3.6), mandipropamid (1.3.3), pyrimorph (1.3.4), valifenalate (1.3.7);

[0193] - reductase in melanin synthesis (MBI-R; 11) pyroquilon (1.2.1), tricyclazole (1.2.2);

[0194] - dehydratase in melanin synthesis (MBI-D, I2); carpropamid (1.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);

[0195] - polyketide synthase in melanin synthesis (MBI-P, I3): tolprocarb (1.2.6);

[0196] J) Plant defence induction (P1 to P8)

[0197] - salicylate-related (P01-P03, P08): acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), dichlobentiazox (J.1.13); phosphonates (P07): fosetyl (J.1.6), fosetyl- aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12); others: potassium or sodium bicarbonate (J.1.9), 4-cyclopro- pyl- / V-(2,4-di-,methoxy-,phenyl)thiadiazole-5-carboxamide (J.1.10);

[0198] K) Unknown mode of action (U)

[0199] - aminopyrifen (K.1.54), benziothiazolinone (K.1.48), bromothalonil (K.1.49), bronopol (K.1.1), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclomezine (K.1.8), difenzoquat (K.1.9), difenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.11), dodine, dodine free base (K.1.18), fenitropan (K.1.12), flufenoxadiazam (K.1.58) [MoA proposed: class II histone deacetylase inhibitor], flumetover (K.1.14), flumetylsulforim (K.1.60), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1.17), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), oxine-copper (K.1.22), picarbutrazox (K.1.41), pyrisoxazole (K.1.37), seboctyla- mine (K.1.61), tebufloquin (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), validamycin (K.1.2); / V-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.27), / V-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- / V-eth- yl- / V-methyl formamidine (K.1.28), / V-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]-241142

[0200] 19

[0201] oxy]-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.29), / V-(5-bromo-6-indan-2-yl-oxy-2-methyl-3-pyridyl)- / V-ethyl- / V-methyl-formamidine (K.1.30), / V-[5-bromo-6-[1-(3,5-difluor-ophenyl)ethoxy]-2-methyl-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.31), / V-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.32), / V-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.33), / V-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.34), / V-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- / V-ethyl- / V-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)- / V-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 / - / -benzoimidaz-ole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), pentyl

[0202] / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl / V-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]- 2-pyridyl]carbamate (K.1.43), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro- 4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), / V-(2,5-dimethyl-4-phenoxy-phe-nyl)- / V-ethyl- / V-methyl-formamidine (K.1.53), / V-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]- / V-ethyl- / V-methyl-formamidine (K.1.56), / V'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.57), / V-methyl-4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]benzenecarbothioamide (K.1.59), / V-methoxy- / V-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.61), / V-((4-[5-(trifluorome-thyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-trifluoro- / V-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-tri-fluoro- / V-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.64), / V-[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzyl]butanamide (K.1.65), / V-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-tri-fluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]urea (K.1.67), 1 , 1 -diethyl-3-[[4-[5-[trifluoromethyl]- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), / V,2-dimethoxy- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol- 3-yl]phenyl]methyl]propanamide (K.1.69), / V-ethyl-2-methyl- / V-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-1-[[4-[5-(tri-fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoro-methyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluorome-thyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(tri-fluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl- 1 -[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4.4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin- 2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole- 4-carboxylate (K.1.83), / V-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-241142

[0203] 20

[0204] phenyl]methyl]pyrazole-4-carboxamide (K.1.84), / V, / V-dimethyl-1-[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]benzyl]-1 H-1 ,2,4-triazol-3-amine (K.1.85), / V-methoxy- / V-methyl- 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-car-boxamide (K.1.87), / V-methoxy-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]me-thyl]pyrazole-4-carboxamide (K.1.88), / V-allyl- / V-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)- 1.2.4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1 ,3-dimethoxy-1-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.91), / V-allyl- / V-[[4-[5-(trifluoromethyl)-1 ,2,4-oxa-diazol-3-yl]phenyl]methyl]acetamide (K.1.92), / V-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadia-zol-3-yl]phenyl]methyl]urea (K.1.94), / V'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.95), / V-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.96), / V'-[2-chloro-4-[(4-cyano-phenyl)methyl]-5-methyl-phenyl]- / V-ethyl- / V-methyl-formamidine (K.1.97), / V'-[2,5-dimethyl-4-(o-tolylmethyl)-phenyl]- / V-ethyl-N-methyl-formamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluoro-phenoxy)-6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]- 5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro- / V-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)- / V-[2-(3,4-dimethylphenyl)-2,2-diflu-oro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phen-oxy)- / V-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), / V-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-flu-oro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104), 2-[cyano-(2,6-difluoro-4-pyri-dyl)amino]-5-methyl- / V-spiro[3.4]octan-3-yl-thiazole-4-carboxamide, 2-[acetyl-(2,6-difluoro- 4-pyridyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, 2-[(2,6-di-fluoro-4-pyridyl)-(2-methoxyacetyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-car-boxamide, 2-[cyano-(2,6-difluoro-4-pyridyl)amino]- / V-(2,2-dimethylcyclobutyl)-5-methyl-thia-zole-4-carboxamide, / V-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / \ / -iso-propoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2-methyl-propanamide, / V-[1-[[3 2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2,2-dimethyl-pro-panamide, / V-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)- / \ / -isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, / V-[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, / V-[2-[3-[2-(2-cyanoethoxy)- 2-(5-fluoro-2-methoxy-phenyl)ethyl]-5-[(Z)- / V-isopropoxy-C-methyl-carbonimidoyl]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propanamide, rac-3-[3-(3-chloro-2-fluoro-phenoxy)- 6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4 / - / -1,2,4-oxadia-zine, (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4 / - / -1,2,4-oxadia-zine, 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone,241142

[0205] 21

[0206] 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanone, 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethenone, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1 / - / -pyrazole-4-carbox- ylate, ethyl 1 -[[4-[[(1 Z)-2-ethoxy-3, 3, 3-trifluoro-1 -propen-1 -yl]oxy]phenyl]methyl]-1 H-pyra- zole-4-carboxylate;

[0207] The fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http: / / www.alanwood.net / pesticides / ); these substances are commercially available.

[0208] The active substances, their preparation and their activity e.g. against fungi is known (www.bcpcpesticidecompendium.bcpc.org / ); many of them are commercially available. Compounds defined by IUPAC nomenclature, their preparation and pesticidal activity are also known (e.g. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-141 317; EP-152031; EP-226917;

[0209] EP-243970; EP-256503; EP-428941; EP-532022; EP-1 028 125; EP-1 035 122;

[0210] EP-1 201 648; EP-1 122244, JP2002316902; DE19650197; DE10021412; DE102005009458; US 3,296,272; US 3,325,503; WO 98 / 46608; WO 99 / 14187; WO 99 / 24413; WO 99 / 27783; WO 00 / 29404; WO 00 / 46148; WO 00 / 65913; WO 01 / 54501; WO 01 / 56358; WO 02 / 22583; WO 02 / 40431; WO 03 / 10149; WO 03 / 11853; WO 03 / 14103; WO 03 / 16286; WO 03 / 53145; WO 03 / 61388; WO 03 / 66609; WO 03 / 74491; WO 04 / 49804; WO 04 / 83193; WO 05 / 120234; WO 05 / 123689; WO 05 / 123690; WO 05 / 63721; WO 05 / 87772; WO 05 / 87773; WO 06 / 15866; WO 06 / 87325; WO 06 / 87343; WO 07 / 82098; WO 07 / 90624, WO 10 / 139271 , WO 11 / 028657, WO 12 / 168188, WO 07 / 006670, WO 11 / 77514; WO 13 / 047749, WO 10 / 069882, WO 13 / 047441, WO 03 / 16303, WO 09 / 90181, WO 13 / 007767, WO 13 / 010862, WO 13 / 127704, WO 13 / 024009, WO 13 / 24010, WO 13 / 047441, WO 13 / 162072, WO 13 / 092224,

[0211] WO 11 / 135833, CN 1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024, WO 09094442, WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP 2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO 16 / 162265, WO 23 / 99460, WO 21 / 244950, WO 21 / 244951,

[0212] WO 22 / 130188, WO 22 / 243810, WO 21 / 255070, WO 21 / 176057, WO 21 / 153754, JP2023064110, JP2022153603, JP2022046550, JP2022031355, WO 22 / 249074,

[0213] WO 23 / 046861, WO 18 / 177894, WO 20 / 212513, WO 20 / 097012, WO 21 / 011722,

[0214] US 2023 / 0069915, WO 24 / 126388, WO 24 / 137594, EP4389739, WO 16 / 096584,

[0215] WO 24 / 120137, WO 24 / 188755, CN115925576, WO 24 / 087613.

[0216] Suitable mixing partners for the compounds of the invention also include biopesticides.

[0217] Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, e.g. metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two major classes, microbial and biochemical pesticides:

[0218] (1) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.

[0219] (2) Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that241142

[0220] 22

[0221] control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (e.g. growth or developmental regulation, attractants, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.

[0222] The following list of biopesticides, in conjunction with which the compounds of the invention can be used, illustrates the possible combinations:

[0223] L) Biopesticides

[0224] L1) Microbial pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleo- phila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium ox- ysporum, Clonostachys rosea f. catenulate (also named Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma floc- culosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomy- ces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzi- anum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulo- cladium oudemansii, Verticillium dahliae, zucchini yellow mosaic virus (avirulent strain); L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and / or plant defense activator activity: harpin protein, plant oils (BM3): tea tree oil, orange oil (L.2.1), eugenol, limonene (L.2.2), geraniol (L.2.3), thymol (L.2.4); Reynoutria sachalinensis extract, au- reobasidin (in particular aureobasidin A (L.2.5)), ambruticin (L.2.6), bafilomycin (L.2.7) (in particular bafilomycin A1 , B1 and C1), chlorflavonin (L.2.8), cinnamaldehyde (L.2.9), natamycin (L.2.10; F8);

[0225] L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and / or nematicidal activity:

[0226] Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tene- brionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium sub- tsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumoso- rosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoro- seus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Strep- tomyces galbus, S. microflavus- L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and / or241142

[0227] 23

[0228] nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl-1 -butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone,

[0229] (E,Z,Z)-3,8,11 -tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate,

[0230] (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetra- decen-1-ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

[0231] L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B.japoni- cum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizo- bium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropic!, Sinorhizobium meliloti

[0232] The biopesticides from group L1) and / or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L3) and / or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and / or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and / or nematicidal activity.

[0233] Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices e.g. ATCC or DSM refer to the acronym of the respective culture collection, for details see e.g. here: http: / / www. wfcc.info / ccinfo / collection / by_acronym / ), are referred to in literature, registered and / or are commercially available: mixtures of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e.g. blastospores in Blossom-Protect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e.g. GELFIX® Gram neas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil orSimbiose-Malz®from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US8,445,255); B. amylo-liquefa-ciens ssp. plantarum strains formerly also sometimes referred to as B. subtilis, recently together with B. methylotrophicus, and B. velezensis classified as B. velezensis (Int. J. Syst. Evol. Microbiol. 66, 1212-1217, 2016): B. a. ssp. plantarum or B. velezensis D747 isolated from air in Kiku-gawashi, Japan (US 20130236522 A1; FERM BP 8234; e.g. Double Nickel™ 55 WDG from Certis LLC, USA), B. a. ssp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. Taegro®from Novozyme Biologicals, Inc., USA), B. a. ssp. plantarum or B. velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. a. ssp. plantarum or B. vele-zen-sis MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B 50595; US 2012 / 0149571 A1; e.g. Integral® from BASF Corp., USA), B. a. ssp. plantarum or B. velezensis QST-713 isolated from peach orchard in 1995 inCalifornia, U.S.A. (NRRL B 21661; e.g. Serenade® MAX from Bayer Crop Science LP, USA), B. a. ssp. plantarum or B. velezensis TJ1000 isolated in 1992 in South Dakoda, U.S.A, (also called 1BE; ATCC BAA-390; CA 2471555 A1; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA); B. firmus CNCM 1-1582, a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009 / 126473, US6,406,690; e.g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizo-sphere in Mexico (IDAC 260707-01 ; e.g. PRO-MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU F22 and BU-F33 isolated at least be-fore 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; e.g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B 30087; e.g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; US2010 / 0260735; WO 2011 / 109395); B. thuringiensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG 6346; ATCC SD-1372; e.g. XenTari®from BioFa AG, Munsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e.g. Dipel® DF from Valent BioSciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e.g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1, a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585215 B1; e.g. Novo-dor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g. Naturalis® from CBC (Europe) S.r.l. , Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g. in Rhizoflo®, His-tick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fer-til. Soils 47, 81-89, 2011); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Em-brapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e.g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013 / 032693; MarroneBio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91-08 isolated from oilseed rape (WO 1996 / 021358; DSM 9660; e.g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g. Messenger™ or HARP-N Tekfrom Plant Health Care pic, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e.g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e.g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhi-zium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e.g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e.g. formerly Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO1991 / 02051 ; Crop Protection 27, 352-361, 2008; e.g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European locations including Germany: P. epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD 5833; Federal Register 76(22), 5808, February 2, 2011; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1; e.g. Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also referred to as T. fertile; e.g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

[0234] According to the invention, the solid material (dry matter) of the biopesticides (with the ex-cep-tion of oils e.g. Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).26

[0235] In accordance with the invention, the weight ratios and percentages used herein for a biological extract e.g. Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

[0236] The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1x1010CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here “CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, e.g. Steinernema feltiae.

[0237] When mixtures comprising microbial pesticides are employed in crop protection, the application rates range from 1x106to 5x1016(or more) CFU / ha, preferably from 1x108to 1x1013CFU / ha, and even more preferably from 1x109to 5x1015CFU / ha and in particular from 1x1012to 5x1014CFU / ha. In the case of nematodes as microbial pesticides (e.g. Steinernema feltiae), the application rates regularly range from 1x105to 1x1012(or more), preferably from 1x108to 1x1011, more preferably from 5x108to 1x1010individuals (e.g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

[0238] When mixtures comprising microbial pesticides are employed in seed treatment, the application rates generally range from 1x106to 1x1012(or more) CFU / seed, preferably from 1x106to 1x109CFU / seed. Furthermore, the application rates with respect to seed treatment generally range from 1x107to 1x1014(or more) CFU per 100 kg of seed, preferably from 1x109to 1x1012CFU per 100 kg of seed.

[0239] Formulations

[0240] The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the invention or a mixture thereof.

[0241] An agrochemical composition comprises a pesticidally effective amount of a compound of the invention or a mixture thereof.

[0242] The compounds of the invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e.g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials e.g. seeds (e.g. GF). These and further compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

[0243] The compositions are prepared in a known manner, e.g. described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0244] Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective241142

[0245] 27

[0246] colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

[0247] Suitable solvents and liquid carriers are water and organic solvents, e.g. mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; hydrocarbons, e.g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

[0248] Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, CaSO4, MgSO4, MgO; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. (NH4)2SO4, (NH4)3PO4, NH4NO3, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

[0249] Suitable surfactants are surface-active compounds, e.g. anionic, cationic, nonionic and am-pho-teric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col-loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International or North American Ed.).

[0250] Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

[0251] Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds e.g. alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and / or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanola-mides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylal-cohols, or vinylacetate.

[0252] Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable241142

[0253] 28

[0254] polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines, or polyethyleneamines.

[0255] Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapters.

[0256] Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0257] Suitable bactericides are bronopol and isothiazolinone derivatives e.g. alkylisothiazolinones and benzisothiazolinones.

[0258] Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.

[0259] Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0260] Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).

[0261] Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0262] Examples for composition types and their preparation are:

[0263] i) Water-soluble concentrates (SL, LS)

[0264] 10-60 wt% of a compound I according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and / or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The active substance dissolves upon dilution with water.

[0265] ii) Dispersible concentrates (DC)

[0266] 5-25 wt% of a compound I according to the invention and 1-10 wt% dispersant (e.g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.

[0267] iii) Emulsifiable concentrates (EC)

[0268] 15-70 wt% of a compound I according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.

[0269] iv) Emulsions (EW, EO, ES)

[0270] 5-40 wt% of a compound I according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

[0271] v) Suspensions (SC, OD, FS)

[0272] In an agitated ball mill, 20-60 wt% of a compound I according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.241142

[0273] 29

[0274] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0275] 50-80 wt% of a compound I according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

[0276] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0277] 50-80 wt% of a compound I according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solution of the active substance.

[0278] viii) Gel (GW, GF)

[0279] In an agitated ball mill, 5-25 wt% of a compound I according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0280] ix) Microemulsion (ME)

[0281] 5-20 wt% of a compound I according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

[0282] x) Microcapsules (CS)

[0283] An oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. di-phenylme-thene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the for-ation of a polyurea microcapsule. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition.

[0284] xi) Dustable powders (DP, DS)

[0285] 1-10 wt% of a compound I according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.

[0286] xii) Granules (GR, FG)

[0287] 0.5-30 wt% of a compound I according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.

[0288] xiii) Ultra-low volume liquids (UL)

[0289] 1-50 wt% of a compound I according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.241142

[0290] 30

[0291] The compositions types i) to xi) may optionally comprise further auxiliaries, e.g. 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.

[0292] The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

[0293] Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10:1.

[0294] The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agro-chemical composition is made up with water, buffer, and / or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

[0295] According to one embodiment, individual components of the composition of the invention e.g. parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

[0296] In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the invention and / or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added.

[0297] In a further embodiment, either individual components of the composition according to the invention or partially premixed components, e.g. components comprising compounds of the invention and / or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

[0298] Application methods

[0299] The compounds of the invention are suitable for use in protecting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, from attack or infestation by animal pests. Therefore, the invention also relates to a plant protection method, which comprises contacting crops, plants, plant propagation materials, e.g. seeds, or soil or water, in which the plants are growing, to be protected from attack or infestation by animal pests, with a pesticidally effective amount of a compound of the invention.

[0300] The compounds of the invention are also suitable for use in combating or controlling animal pests. Therefore, the invention also relates to a method of combating or controlling animal pests, which comprises contacting the animal pests, their habitat, breeding ground, or food supply, or the crops, plants, plant propagation materials, e.g. seeds, or soil, or the area, material or environment in which the animal pests are growing or may grow, with a pesticidally effective amount of a compound of the invention.241142

[0301] 31

[0302] The compounds of the invention are effective through both contact and ingestion. Further-more, the compounds of the invention can be applied to any and all developmental stages, e.g. egg, larva, pupa, and adult.

[0303] The compounds of the invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the invention can be applied together with a mixing partner or in form of compositions comprising said mixtures. The components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture “in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

[0304] The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, e.g. seeds, soil, or the area, material or environment by the pests. Suitable application methods include i.a. soil treatment, seed treatment, in furrow application, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow. Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the invention. Suitable pheromones for specific crops and pests are known and publicly available from databases of pheromones and semiochemicals, e.g. http: / / www.pherobase.com.

[0305] As used herein, the term "contacting" includes both direct contact (applying the com-pounds / compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds / compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material, or environment in which a pest is growing or may grow, of the animal pest or plant).

[0306] The term “animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.

[0307] The term "crop" refers to both, growing and harvested crops.

[0308] The term “plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize I sweet and field corn); beet, e.g. sugar beet, or fodder beet; fruits, e.g. pomes, stone fruits, or soft fruits, e.g. apples, pears, plums, peaches, nectarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, e.g. beans, lentils, peas, alfalfa, or soybeans; oil plants, e.g. rapeseed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts, or soybeans; cucurbits, e.g. squashes, pumpkins, cucumber or melons; fiber plants, e.g. cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grapefruits or mandarins; vegetables, e.g. eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, e.g. avocados, cinnamon, or camphor; energy and raw material plants,241142

[0309] 32

[0310] e.g. corn, soybean, rapeseed, sugarcane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines; hop; sweet leaf (Stevia); natural rubber plants or ornamental and forestry plants, shrubs, broad-leaved trees or evergreens, eucalyptus; turf; lawn; grass. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugar cane; fruits; vines; ornamentals; or vegetables, e.g. cucumbers, tomatoes, beans or squashes.

[0311] The term "cultivated plants" is to be understood as including plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

[0312] Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR / Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, which differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or have been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

[0313] Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to ALS inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®.

[0314] Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and HPPD inhibitors, like isoxaflutole and mesotrione.

[0315] Transgenes which have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

[0316] Transgenic corn events comprising herbicide tolerance genes are e.g., but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, VCO-01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0317] Transgenic soybean events comprising herbicide tolerance genes are e.g., but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12,241142

[0318] 33

[0319] A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

[0320] Transgenic cotton events comprising herbicide tolerance genes are e.g., but not excluding others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

[0321] Transgenic canola events comprising herbicide tolerance genes are e.g., but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHYU, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0322] Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pin 11. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate in-sect genes. An example for such a transgene is dvsnf7.

[0323] Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are e.g., but not excluding others, Bt10, Bt11 , Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

[0324] Transgenic soybean events comprising genes for insecticidal proteins are e.g., but not excluding others, MON87701, MON87751 and DAS-81419.

[0325] Transgenic cotton events comprising genes for insecticidal proteins are e.g., but not excluding others, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0326] Increased yield has been created by increasing ear biomass using the transgene athb17, be-ing present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

[0327] Cultivated plants comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1Aand fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

[0328] Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.

[0329] Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.241142

[0330] 34

[0331] Plants comprising singular or stacked traits as well as the genes and events providing these traits are known (http: / / www.isaaa.org / gmapprovaldatabase) and (http: / / cera-gmc.org / GMCropDatabase).

[0332] Further information on specific events and methods to detect them can be found for canola events MS1, MS8, RF3, GT73, MON88302, KK179 in W001 / 031042, W001 / 041558, W001 / 041558, W002 / 036831, WO11 / 153186, W013 / 003558, for cotton events MON1445, MON15985, MON531(MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701 , 81910 in WO02 / 034946, W002 / 100163, W002 / 100163, W003 / 013224, WO04 / 072235, WO04 / 039986, WO05 / 103266, W005 / 103266, WO06 / 128573, W007 / 017186, W008 / 122406, W008 / 151780, WO12 / 134808, WO13 / 112527, for corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411 , 33121 , MON87403, MON87419 in W098 / 044140, US02 / 102582, US03 / 126634, WO04 / 099447, W004 / 011601, WO05 / 103301 , W005 / 061720, W005 / 059103, WO06 / 098952, WO06 / 039376, US2007 / 292854, WO07 / 142840, W007 / 140256, WO08 / 112019, W009 / 103049, WO09 / 111263, W010 / 077816, WO11 / 084621, WO11 / 062904, WO11 / 022469, WO13 / 169923, WO14 / 116854, WO15 / 053998, WO15 / 142571, for potato events E12, F10, J3, J55, V11, X17, Y9 in WO14 / 178910, WO14 / 178913, WO14 / 178941, WO14 / 179276, WO16 / 183445, WO17 / 062831 , W017 / 062825, for rice events LLRICE06, LLRICE601, LLRICE62 in WO00 / 026345, WO00 / 026356, WO00 / 026345 for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751 in WO04 / 074492, WO06 / 130436, WO06 / 108674, WO06 / 108675, WO08 / 054747, W008 / 002872, WO09 / 064652, WO09 / 102873, W010 / 080829, WO10 / 037016, W011 / 066384, W011 / 034704, W012 / 051199, W012 / 082548, WO13 / 016527, WO13 / 016516, WO14 / 201235.

[0333] The use of compositions according to the invention on cultivated plants may result in effects which are specific to a cultivated plant comprising a certain gene or event. These effects may comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigor, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.

[0334] It has been found that the pesticidal activity of the compounds of the invention may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a complementary insecticidal activity can advantageously be used.

[0335] The term "plant propagation material" refers to all the generative parts of the plant e.g. seeds and vegetative plant material e.g. cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be trans-planted after germination or after emergence from soil, may also be included. These plant propagation241142

[0336] 35

[0337] materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

[0338] The term “seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.

[0339] In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various compounds / composi-tions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired pesticidal effect and duration, weather, target species, locus, mode of application.

[0340] In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

[0341] For use in treating crop plants, e.g. by foliar application, the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.

[0342] The compounds of the invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects. The invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and / or after pregermination with a compound of the invention. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.

[0343] The term “seed treatment” comprises e.g. seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

[0344] The invention also comprises seeds coated with or containing the active compound. The term "coated with and / or containing" generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.

[0345] Suitable seed is e.g. seed of cereals, root crops, oil crops, vegetables, spices, ornamentals, e.g. seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize I sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass,241142

[0346] 36

[0347] tomatoes, leeks, pumpkin / squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants e.g. potatoes, sugar cane, tobacco, grapes, petunias, geranium / pelargoniums, pansies and impatiens.

[0348] In addition, the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides.

[0349] Conventional seed treatment formulations include e.g. flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.

[0350] The active substance concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40% by weight.

[0351] In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g / l of active ingredient, 1-200 g / l Surfactant, 0 to 200 g / l anti-freezing agent, 0 to 400 g / l of binder, 0 to 200 g / l of a pigment and up to 1 liter of a solvent, preferably water.

[0352] Especially preferred FS formulations of the compounds of the invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g / l) of the active ingredient, from 0.1 to 20% by weight (1 to 200 g / l) of at least one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5 to 20% of an antifreeze agent, from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and / or a dye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder (sticker / adhesion agent), optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative e.g. a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight and a filler / vehicle up to 100% by weight.

[0353] In the treatment of seed, the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.

[0354] The invention therefore also relates to seed comprising a compound of the invention, or an agriculturally useful salt thereof, as defined herein. The amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops e.g. lettuce the rate can be higher.

[0355] The compounds of the invention may also be used for improving the health of a plant. Therefore, the invention also relates to a method for improving plant health by treating a plant, plant propagation material and / or the locus where the plant is growing or is to grow with an effective and non-phytotoxic amount of a compound of the invention.241142

[0356] 37

[0357] As used herein “an effective and non-phytotoxic amount” means that the compound is used in a quantity which allows to obtain the desired effect but which does not give rise to any phytotoxic symptom on the treated plant or on the plant grown from the treated propagule or treated soil. "Plant health" is defined as a condition of the plant and / or its products which is determined by several aspects alone or in combination with each other e.g. yield (e.g. increased biomass and / or increased content of valuable ingredients), quality (e.g. improved content or composition of certain ingredients or shelf life), plant vigour (e.g. improved plant growth and / or greener leaves (“greening effect”), tolerance to abiotic (e.g. drought) and / or biotic stress (e.g. disease) and production efficiency (e.g., harvesting efficiency, processability).

[0358] The above identified indicators for the health condition of a plant may be interdependent and may result from each other. Each indicator is defined in the art and can be determined by methods known to a skilled person.

[0359] The compounds of the invention are also suitable for use against non-crop insect pests. For use against said non-crop pests, compounds of the invention can be used as bait composition, gel, general insect spray, aerosol, as ultra-low volume application and bed net (impregnated or surface applied). Furthermore, drenching and rodding methods can be used.

[0360] As used herein, the term “non-crop insect pest” refers to pests, which are particularly relevant for non-crop targets, e.g. ants, termites, wasps, flies, ticks, mosquitoes, bed bugs, crickets, or cockroaches.

[0361] The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product, which is sufficiently attractive to incite insects e.g. ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimulants are preferably chosen from animal and / or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and / or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant. Sex pheromones are known to be more insect specific. Specific pheromones are known (http: / / www.pherobase.com).

[0362] For use in bait compositions, the typical content of active ingredient is from 0.001 wt% to 15 wt%, desirably from 0.001 wt% to 5 wt% of active compound.

[0363] Formulations of the compounds of the invention as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for professional or non-professional users for controlling pests e.g. flies, fleas, ticks, bed bugs, mosquitoes or cockroaches. Aerosol recipes are preferably composed of the active compound, solvents, furthermore auxiliaries e.g. emulsifiers, perfume oils, if appropriate stabilizers, and, if required, propellants.

[0364] The oil spray formulations differ from the aerosol recipes in that no propellants are used.

[0365] For use in spray compositions, the content of active ingredient is from 0.001 to 80 wt%, preferably from 0.01 to 50 wt% and most preferably from 0.01 to 15 wt%.

[0366] The compounds of the invention and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.241142

[0367] 38

[0368] Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of the invention and its re-spec-tive compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-flytrap. Insecticidal compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise a mixture including the insecticide, optionally a repellent and at least one binder. The compounds of the invention and its compositions can be used for protecting wooden materials e.g. trees, board fences, sleepers, frames, artistic artifacts, etc. and buildings, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants, termites and / or wood or textile destroying beetles, and for controlling ants and termites from doing harm to crops or human beings (e.g. when the pests invade into houses and public facilities or nest in yards, orchards or parks).

[0369] Customary application rates in the protection of materials are, e.g., from 0.001 g to 2000 g or from 0.01 g to 1000 g of active compound per m2treated material, desirably from 0.1 g to 50 g per m2.

[0370] Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 wt%, preferably from 0.1 to 45 wt%, and more preferably from 1 to 25 wt% of at least one repellent and / or insecticide.

[0371] Digital application

[0372] The compounds of the invention and the compositions containing them may be applied in combination with, or by utilizing smart agricultural technologies, such as precision agriculture, remote and proximate imaging and image recognition, or smart agricultural site management programs. These smart agricultural technologies typically include models, e.g. computer pro-grams, that support the user by considering information from a wide variety of sources to increase the quality and yield of harvested material, reduce damage by pests including the prediction of pest pressure and smart application of crop protection products, secure environ-mental protection, support quick and reliable agronomic decision making, reduce usage of fertilizers and crop protection products, reduce product residues in consumables increase spatial and temporal precision of agronomical measures, automate processes, and enable traceability of measures.

[0373] Commercially available systems which include agronomic models are e.g. FieldScripts™ from The Climate Corporation, Xarvio™ from BASF, AGLogic™ from John Deere, etc.

[0374] Information input for these models include but is not limited to soil data, information on the plants that are currently growing or that may grow at the area of interest including crop plants and / or unwanted vegetation, weather information, information on the location of the area and directly derivable information thereof, information on pest pressure, information on beneficial organisms, and I or historic information of any of the aforementioned.

[0375] The information usable for precision agriculture may be based on input by at least one user, be accessible from external data sources and databases, or be based on sensor data. Data sources typically includes proximate-detection systems like soil-borne sensors and remote sensing as may be achieved by imaging with unmanned airborne vehicles like drones, or satellites. Sensors may be included in an Internet-of-Things system and may be directly or indirectly connected to the processing unit, e.g. via a wireless network and / or cloud applications. The241142

[0376] 39

[0377] information is typically taken into account by at least one processing unit and used to provide recommendations and generate control signals.

[0378] Typical technologies that are used in smart agricultural technologies include self-steering robots (such as tractors, harvesters, drones), artificial intelligence (e.g. machine learning), imaging technologies (e.g. image segmentation technologies), big data analysis, and model generation, cloud computing, and machine-to-machine communication.

[0379] Precision agriculture such as precision farming is characterized by spatially and / or temporally resolved, targeted application of active ingredients like pesticides, plant-growth-regulators, fertilizers, and / or water including the variation of application rates over the agronomic site, zone or spot application, and of the spatially and / or temporally resolved, targeted planting or seeding of desired plant propagation material to a agronomic site. Precision farming typically includes the use of geo-positioning technologies like GPS for gaining information on the location and boundaries of the area of interest, the utilized application equipment, sensing equipment and recorded data, and to control the actions of farm vehicles such as spraying. By combining geo-positioning data with (digital) maps, it is possible to (semi)-automate agricultural measures at the site of interest, e.g. by using (semi)-autonomous spraying or seeding equipment.

[0380] Precision farming may typically include the application of smart spraying equipment, e.g. spot spraying, and precision spraying at a farm, e.g. by irrigation systems, tractors, robots, helicopters, airplanes, unmanned aerial vehicles, such as drones. Such equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and configured to provide a recommendation or decision based on the analysis of the input data to apply the compounds of the invention or compositions comprising them to the agronomic site, e.g. the soil, the crop plants, or to control pests in a specific and precise manner. For example, pests may be detected, identified, and / or classified from imagery acquired by a camera. Such identification and / classification can make use of image processing algorithms, which may utilize artificial intelligence (e.g. machine learning algorithms), or decision trees. In this manner, the compounds or compositions described herein can be applied only at the required location, point in time and dose rate.

[0381] Pests

[0382] The compounds of the invention are especially suitable for efficiently combating animal pests e.g. arthropods, gastropods and nematodes including:

[0383] Insects from the order of Lepidoptera, e.g. Achroia spp., Achyra spp., Acleris spp., Acrolepia spp., Acrolepiopsis spp., Acronicta spp., Adoxophyes spp., Aedia spp., Agrotis spp., Alabama spp., Aleurodicus spp., Alsophila spp., Ampelophaga spp., Amyelois spp., Anacampsis spp., Anagasta spp., Anarsia spp., Anisota spp., Anomis spp., Antheraea spp., Anticarsia spp., Apamea spp., Aproaerema spp., Archips spp., Argyresthia spp., Argyroploce spp., Argyrotaenia spp., Ascotis spp., Athetis spp., Austroasca spp., Autographa spp., Barathra spp., Batrachedra spp., Bedellia spp., Bonagota spp., Borbo spp., Bucculatrix spp., Bupalus spp., Busseola spp., Cacoecia spp., Cactoblastis spp., Cadra spp., Calingo spp., Caloptilis spp., Capua spp., Car-posina spp., Cephus spp., Chaetocnema spp., Cheimatobia spp., Chilo spp., Chloridea spp., Choreutis spp., Choristoneura spp., Chrysodeixis spp., Cirphis spp., Clepsis spp., Clysia spp., Cnaphalocerus spp., Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Corcyra spp., Crambus241142

[0384] 40

[0385] spp., Crocidosema spp., Cryptoblabes spp., Cydalima spp., Cydia spp., Cynthia spp., Dalaca spp., Dasychira spp., Datana spp., Dendrolimus spp., Desmia spp., Diaphania spp., Diatraea spp., Diparopsis spp., Diphthera spp., Dizygomyza spp., Earias spp., Ecdytolopha spp., Egira spp., Elasmopalpus spp., Eldana spp., Endopiza spp., Ennomos spp., Eoreuma spp., Ephestia spp., Epinotia spp., Epiphyas spp., Erannis spp., Erionota spp., Etiella spp., Eulia spp., Eupoe-cilia spp., Euproctis spp., Euxoa spp., Euzophera spp., Evertria spp., Faronta spp., Feltia spp., Galleria spp., Gracillaria spp., Grapholita spp., Halysidota spp., Harrisina spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hellula spp., Hemileuca spp., Herpetogramma spp., Hibernia spp., Hofmannophila spp., Homoeosoma spp., Homona spp., Hypena spp., Hyphantria spp., Hyponeuma spp., Hyponomeuta spp., Kakivoria spp., Keiferia spp., Lambdina spp., Lamprosema spp., Laspeyresia spp., Leguminivora spp., Lerodea spp., Leucinodes spp., Leucoma spp., Leucoptera spp., Leuminivora spp., Lithocolletis spp., Lithophane spp., Llattia spp., Lobesia spp., Lophocampa spp., Loxagrotis spp., Loxostege spp., Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra spp., Manduca spp., Marasmia spp., Marmara spp., Maruca spp., Megalopyge spp., Melanchra spp., Melanitis spp., Melittia spp., Mocis spp., Monochroa spp., Mythimna spp., Naranga spp., Nemapogon spp., Neoleucinodes spp., Nepytia spp., Nymphula spp., Oiketicus spp., Omiodes spp., Omphisa spp., Operophtera spp., Orgyia spp., Oria spp., Orthaga spp., Orthosia spp., Ostrinia spp., Paleacrita spp., Pandemis spp., Panolis spp., Papaipema spp., Papilio spp., Paramyelois spp., Paranthrene spp., Paraponyx spp., Par-nara spp., Paysandisia spp., Pectinophora spp., Pelopidas spp., Peribatodes spp., Peridroma spp., Perileucoptera spp., Phalera spp., Phryganidia spp., Phthorimaea spp., Phyllocnistis spp., Phyllonorycter spp., Pieris spp., Pilocrocis spp., Plathypena spp., Platynota spp., Platyptilia spp., Plebejus spp., Plodia spp., Plusia spp., Plutella spp., Pontia spp., Prays spp., Prodenia spp., Proeulia spp., Proxenus spp., Pseudaletia spp., Pyrausta spp., Rachiplusia spp., Rhizo-bius spp., Rhyacionia spp., Richia spp., Sabulodes spp., Schizura spp., Schoenobius spp., Schreckensteinia spp., Scirpophaga spp., Scotia spp., Scrobipalpa spp., Sesamia spp., Seudyra spp., Sitotroga spp., Sparganothis spp., Spilonota spp., Spodoptera spp., Stigmella spp., Stomopteryx spp., Strymon spp., Sylepta spp., Synanthedon spp., Tecia spp., Telehin spp., Thaumatopoea spp., Thaumatotibia spp., Thaumetopoea spp., Thecla spp., Theresimima spp., Thyrinteina spp., Thysanoplusia spp., Tildenia spp., Tinea spp., Tineola spp., Tortrix spp., Toxoptera spp., Trichophaga spp., Trichoplusia spp., Tuta spp., Udea spp., Virachola spp., Yponomeuta spp., Zeiraphera spp., Zeiraphera canadensis spp.;

[0386] Insects from the order of Coleoptera, e.g. Acalymma spp., Acanthoscehdes spp., Acan-thoscelides spp., Adoretus spp., Aeolus spp., Agelastica spp., Agrilus spp., Agriotes spp., Alphitobius spp., Amphicerus spp., Amphimallus spp., Ancognatha spp., Anisandrus spp., An-isoplia spp., Anobium spp., Anomala spp., Anoplophora spp., Anthonomus spp., Anthrenus spp., Aphthona spp., Apion spp., Apogonia spp., Artipus spp., Athous spp., Atomaria spp., Attagenus spp., Aulacophora spp., Baris spp., Blastophagus spp., Blitophaga spp., Bothynoderes spp., Brassicogethes spp., Bruchidius spp., Bruchus spp., Byctiscus spp., Cala-mobius spp., Callidiellum spp., Callopistria spp., Callosobruchus spp., Cameraria spp., Cassida spp., Cerotoma spp., Cetonia spp., Ceuthorhynchus spp., Ceutorhynchus spp., Chaetocnema spp., Cleonus spp., Conoderus spp., Conotrachelus spp., Cosmopolites spp., Costelytra spp., Crioceris spp., Cryptolestes spp., Cryptorhynchus spp., Ctenicera spp., Curculio spp., Cy-clocephala spp., Cylas spp., Cylindrocopturus spp., Dactylispa spp., Dectes spp., Dermestesspp., Diabrotica spp., Diaprepes spp., Dichocrocis spp., Dicladispa spp., Diloboderus spp., Dio-calandra spp., Donacia spp., Echinocnemus spp., Enaphalodes spp., Epicaerus spp., Epicauta spp., Epilachna spp., Epitrix spp., Eutheola spp., Eutinobothrus spp., Faustinas spp., Fidia spp., Gibbium spp., Gnathocerus spp., Heteronychus spp., Holotrichia spp., Hylamorpha spp., Hy-lobius spp., Hylotrupes spp., Hypera spp., Hypomeces spp., Hypothenemus spp., Ips spp., Lachnosterna spp., Lasioderma spp., Latheticus spp., Lathridius spp., Lema spp., Leptinotarsa spp., Leptispa spp., Limonius spp., Liogenys spp., Lissorhoptrus spp., Lixus spp., Luperodes spp., Lyctus spp., Macrodactylus spp., Maladera spp., Megaplatypus spp., Megascelis spp., Melanotus spp., Meligethes spp., Melolontha spp., Metamasius spp., Microtheca spp., Migdolus spp., Monochamus spp., Monocrepidius spp., Monolepta spp., Mordellistena spp., Mythimna spp., Naupactus spp., Niptus spp., Obereopsis spp., Oberia spp., Oemona spp., Oides spp., Opatrum spp., Oryctes spp., Oryzaephilus spp., Oryzaphagus spp., Otiorhynchus spp., Otior-rhynchus spp., Oulema spp., Oxycetonia spp., Phaedon spp., Phlyctinus spp., Phoracantha spp., Phyllobius spp., Phyllopertha spp., Phyllophaga spp., Phyllotreta spp., Popillia spp., Prem-notrypes spp., Prostephanus spp., Psacothea spp., Psylliodes spp., Ptinus spp., Pulga spp., Rhizopertha spp., Rhynchophorus spp., Saperda spp., Scelodonta spp., Sciobius spp., Scolytus spp., Scyphophorus spp., Selatosomus spp., Sitona spp., Sitophilus spp., Sphenophorus spp., Stegobium spp., Sternechus spp., Strophomorphus spp., Symphyletes spp., Tanymecus spp., Tenebrio spp., Tenebrioides spp., Tribolium spp., Trogoderma spp., Tropinota spp., Tychius spp., Xylotrechus spp., Zabrus spp.;

[0387] Insects from the order of Diptera e.g. Aedes spp., Anastrepha spp., Anopheles spp., Atherigona spp., Bactrocera spp., Bibio spp., Calliphora spp., Ceratitis spp., Chironomus spp., Chlorops spp., Chrysomyia spp., Chrysops spp., Cochliomyia spp., Contarinia spp., Cordylobia spp., Culex spp., Culicoides spp., Culiseta spp., Cuterebra spp., Dacus spp., Dasineura spp., Delia spp., Dermatobia spp., Diopsis spp., Drosophila spp., Euxesta spp., Fannia spp., Gastraphilus spp., Geomyza spp., Glossina spp., Haematobia spp., Haplodiplosis spp., Hippelates spp., Hydrellia spp., Hylemyia spp., Hypoderma spp., Hyppobosca spp., Leptoconops spp., Liri-omyza spp., Lucilia spp., Lycoria spp., Mansonia spp., Mayetiola spp., Melanagromyza spp., Musca spp., Muscina spp., Oestrus spp., Opomyza spp., Orseolia spp., Oscinella spp., Pe-gomya spp., Phlebotomus spp., Phorbia spp., Phytomyza spp., Prosimulium spp., Psila spp., Psorophora spp., Rhagoletis spp., Rivellia spp., Sarcophaga spp., Simulium spp., Sitodiplosis spp., Stomoxys spp., Tabanus spp., Tannia spp., Thecodiplosis spp., Tipula spp., Wohlfahrtia spp., Zaprionus spp.;

[0388] Insects from the order of Thysanoptera e.g., Baliothrips spp., Dichromothrips spp., Drepanothrips spp., Echinothrips spp., Enneothrips spp., Frankliniella spp., Fulmekiola spp., Haplothrips spp., Heliothrips spp., Hercinothrips spp., Kakothrips spp., Microcephalothrips spp., Neohydatothrips spp., Pezothrips spp., Rhipiphorothrips spp., Scirtothrips spp., Stenchae-tothrips spp., Taeniothrips spp., Thrips spp.;

[0389] Insects from the order of Hemiptera e.g., Acizzia spp., Acrosternum spp., Acyrthosiphon spp., Adelges spp., Adelphocoris spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Al-eurodes spp., Aleurodicus spp., Aleurolobus spp., Aleurothrixus spp., Aleurotrachelus spp., Aleyrodes spp., Amrasca spp., Anasa spp., Antestiopsis spp., Anuraphis spp., Aonidiella spp., Aphanostigma spp., Aphidula spp., Aphis spp., Arboridia spp., Arilus spp., Aspidiella spp., As-pidiotus spp., Atanus spp., Aulacaspis spp., Aulacorthum spp., Bactericera spp., Bagrada spp.,Bathycoelia spp., Bemisia spp., Blissus spp., Bothrogonia spp., Brachycaudus spp., Brachy-colus spp., Brachycorynella spp., Brevennia spp., Brevicoryne spp., Brevipalpus spp., Cacopsylla spp., Calligypna spp., Calocoris spp., Campylomma spp., Capitophorus spp., Car-neocephala spp., Cavariella spp., Cavelerius spp., Ceraplastes spp., Ceratovacuna spp., Cero-plastes spp., Cerosipha spp., Chaetosiphon spp., Chinavia spp., Chionaspis spp., Chlorita spp., Chromaphis spp., Chrysomphalus spp., Cicadulina spp., Cimex spp., Circulifer spp., Coccomyti-lus spp., Coccus spp., Corythucha spp., Creontiades spp., Cryptomyzus spp., Ctenarytaina spp., Cyrtopeltis spp., Daktulosphaira spp., Dalbulus spp., Dasynus spp., Dialeurodes spp., Di-aphorina spp., Diaspidiotus spp., Diaspis spp., Dichelops spp., Diconocoris spp., Distantiella spp., Diuraphis spp., Doralis spp., Dreyfusia spp., Drosicha spp., Dysaphis spp., Dysau-lacorthum spp., Dysdercus spp., Dysmicoccus spp., Edessa spp., Empoasca spp., Epidiaspis spp., Eriosoma spp., Erythroneura spp., Eurygaster spp., Euscelis spp., Euschistus spp., Fer-risia spp., Fiorinia spp., Geococcus spp., Geocoris spp., Glycaspis spp., Halyomorpha spp., He-liopeltis spp., Homalodisca spp., Horcias spp., Hyalesthes spp., Hyalopterus spp., Hy-peromyzus spp., Icerya spp., Idiocerus spp., Idioscopus spp., Jacobiella spp., Laodelphax spp., Lecanium spp., Lecanoideus spp., Lepidosaphes spp., Leptocorisa spp., Leptoglossus spp., Lipaphis spp., Lygocoris spp., Lygus spp., Maconellicoccus spp., Macropes spp., Macrosiphum spp., Macrosteles spp., Mahanarva spp., Marchalina spp., Megacopta spp., Megoura spp., Melanaphis spp., Melanocallis spp., Metcafiella spp., Metcalfa spp., Metopolophium spp., Mo-nellia spp., Monelliopsis spp., Murgantia spp., Myzocallis spp., Myzus spp., Nasonovia spp., Ne-omegalotomus spp., Neotoxoptera spp., Nephotettix spp., Nezara spp., Nilaparvata spp., Ny-sius spp., Oebalus spp., Oncometopia spp., Orthezia spp., Oxycaraenus spp., Palaeolecanium spp., Pangaeus spp., Parabemisia spp., Parlatoria spp., Parthenolecanium spp., Pemphigus spp., Pentastiridius spp., Peregrinus spp., Perkinsiella spp., Phenacoccus spp., Philaenus spp., Phloeomyzus spp., Phorodon spp., Phylloxera spp., Piesma spp., Piezodorus spp., Pinnaspis spp., Pianococcus spp., Prosapia spp., Protopulvinaria spp., Psallus spp., Psammotettix spp., Pseudacysta spp., Pseudatomoscelis spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudotheraptus spp., Psylla spp., Pteromalus spp., Pulvinaria spp., Pyrilla spp., Quadraspidi-otus spp., Quesada spp., Rastrococcus spp., Recilia spp., Reduvius spp., Rhizoecus spp., Rhodnius spp., Rhopalomyzus spp., Rhopalosiphum spp., Sagatodes spp., Sahlbergella spp., Saissetia spp., Sappaphis spp., Scaphoideus spp., Scaptocoris spp., Schizaphis spp., Schizo-neura spp., Scotinophara spp., Scotinophora spp., Selenaspidus spp., Sipha spp., Sitobion spp., Sogata spp., Sogatella spp., Solubea spp., Spissistilus spp., Stephanitis spp., Ten-alaphara spp., Tetraleurodes spp., Tetraneura spp., Therioaphis spp., Thyanta spp., Tibraca spp., Tomaspis spp., Toxoptera spp., Trialeurodes spp., Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp., Viteus spp., Zyginidia spp.;

[0390] Insects from the order Hymenoptera e.g. Acanthomyops spp., Athalia spp., Atta spp., Bombus spp., Brachymyrmex spp., Camponotus spp., Cardiocondyla spp., Cephus spp., Chalibion spp., Crematogaster spp., Dasymutilla spp., Diprion spp., Dolichovespula spp., Dorymyrmex spp., Dryocosmus spp., Formica spp., Hoplocampa spp., Iridomyrmex spp., Lasius spp., Leptocybe spp., Linepithema spp., Liometopum spp., Monomorium spp., Nylandria spp., Pachycondyla spp., Paratrechina spp., Paravespula spp., Pheidole spp., Pogonomyrmex spp., Polistes spp., Prenolepis spp., Pseudomyrmex spp., Schelipron spp., Sirex spp., Solenopsis spp., Spheciusspp., Sphex spp., Tapinoma spp., Tetramorium spp., Vespa spp., Vespula spp., Wasmannia spp., Xylocopa spp.;

[0391] Insects from the order Orthoptera e.g. Acheta spp., Calliptamus spp., Ceuthophilus spp., Chor-toicetes spp., Diastrammena spp., Dociostaurus spp., Gryllotalpa spp., Gryllus spp., Hiero-glyphus spp., Kraussaria spp., Locusta spp., Melanoplus spp., Nomadacris spp., Oedaleus spp., Oxya spp., Scapteriscus spp., Schistocerca spp., Stemopelmatus spp., Tachycines spp., Zonozerus spp.;

[0392] Pests from the class Arachnida e.g. Acallitus spp., Acarus spp., Aceria spp., Achaearanea spp., Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calepitrimerus spp., Carpoglyphus spp., Cheiracanthium spp., Colomerus spp., Demodex spp., Dermacentor spp., Dermanyssus spp., Eotetranychus spp., Epitrimerus spp., Eratigena spp., Eriophyes spp., Eriophytes spp., Eutetranychus spp., Halotydeus spp., Hemitar-sonemus spp., Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Lycosa spp., Metatetranychus spp., Oligonychus spp., Ornithodorus spp., Ornithonyssus spp., Ornothonys-sus spp., Otobius spp., Panonychus spp., Penthaleus spp., Petrobia spp., Phyllocoptruta spp., Phytonemus spp., Polyphagotarsonemus spp., Psoroptes spp., Pyemotes spp., Raoiella spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp., Tarsonemus spp., Tetranychus spp., Trombicula spp., Tyrophagus spp., Vasates spp.;

[0393] Pests from the phylum Nematoda, e.g. Anguina spp., Aphelenchoides spp., Belonolaimus spp., Bursaphelenchus spp., Criconema spp., Criconemella spp., Criconemoides spp., Ditylenchus spp., Dolichodorus spp., Globodera spp., Heliocotylenchus spp., Hemicriconemoides spp., Hemicycliophora spp., Heterodera spp., Hirshmanniella spp., Hoploaimus spp., Longidorus spp., Meloidogyne spp., Mesocriconema spp., Nacobbus spp., Paratrichodorus spp., Pratylen-chus spp., Radopholus spp., Rhadopholus spp., Rhodopholus spp., Rotylenchus spp., Scutello-nema spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Xiphinema spp.;

[0394] Insects from the order Blattodea e.g. Blatta spp., Blattella spp., Coptotermes spp., Cornitermes spp., Cryptotermes spp., Eurycotis spp., Globitermes spp., Heterotermes spp., Incisitermes spp., Kalotermes spp., Macrotermes spp., Marginitermes spp., Mastotermes spp., Nasutitermes spp., Neocapritermes spp., Neotermes spp., Odontotermes spp., Panchlora spp., Parcoblatta spp., Periplaneta spp., Procornitermes spp., Pycnoscelus spp., Reticulitermes spp., Rhyparobia spp., Supella spp., Zootermopsis spp.;

[0395] Insects from the order Siphonoptera e.g. Cediopsylla spp., Ceratophyllus spp., Cten-ocephalides spp., Nosopsyllus spp., Pulexspp., Trichodectes spp., Tunga spp., Xenopsylla spp.;

[0396] Insects from the order Thysanura e.g. Ctenolepisma spp., Lepisma spp., Thermobia spp.; Pests from the class Chilopoda e.g. Geophilus spp., Scutigera spp.;

[0397] Pests from the class Diplopoda e.g. Blaniulus spp., Julus spp., Narceus spp.;

[0398] Pests from the class Symphyla e.g. Scutigerella spp.;

[0399] Insects from the order Dermaptera, e.g. Forficula spp.;

[0400] Insects from the order Collembola, e.g. Onychiurus spp.;

[0401] Pests from the order Isopoda, e.g. Armadillidium spp., Oniscus spp., Porcellio spp.;

[0402] Insects from the order Phthiraptera, e.g. Bovicola spp., Damalinia spp., Haematopinus spp., Linognathus spp., Menacanthus spp., Menopon spp., Pediculus spp., Pthirus spp., Solenopotes spp., Trichodectes spp..44

[0403] Further pest species which may be controlled by compounds I include: from the phylum Molluscs, Arion spp., Biomphalaria spp., Bulinus spp., Cornu spp., Deroceras spp., Dreissena spp., Galba spp., Limax spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.. The compounds of the invention are particularly suitable for efficiently combating

[0404] insects from the order of Lepidoptera e.g. Agrotis ypsilon, Amyelois transitella, Anticarsia gem-matalis, Chilo suppressalis, Chloridea virescens, Chrysodeixis includens, Cnaphalocrocis medi-nalis, Cydia molesta, Cydia pomonella, Diatraea saccharalis, Euxoa auxiliaris, Grapholita molests, Helicoverpa armigera, Helicoverpa zea, Lobesia botrana, Mythimna separata, Naranga aenescens, Pectinophora gossypiella, Phthorimaea operculella, Phyllocnistis citrella, Pieris ra-pae, Plutella xylostella, Pseudoplusia includens, Scirpophaga incertulas, Sesamia inferens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodop-tera litura, Trichoplusia ni, Tryporyza incertulas, Tuts absoluta;

[0405] Insects from the order of Coleopters e.g. Aeolus spp. e.g., Aeolus mellillus, Agriotes fusicollis , Agriotes lineatus, Agriotes obscurus, Alphitobius diaperinus, Anthonomus grandis, Atomaria linearis, Ceutorhynchus assimilis, Ceutorhynchus napi, Ceutorhynchus pallidactylus, Ceutorhyn-chus picitarsis, Diabrotica barberi, Diabrotica speciosa, Diabrotica undecimpunctata, Diabrotica virgifera, Dicladispa armigera, Epilachna cucurbitae, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Melanotus spp. e.g., Melanotus cribulosus, Meligethes aeneus, Phyllophaga cuya-bana, Phyllotreta striolata, Phyllotreta vittula, Popillia japonica, Sphenophorus levis, Tribolium confusum;

[0406] Insects from the order of Diptera e.g. Aedes aegypti, Bactrocera cucurbitae, Ceratitis capitata, Delia antiqua, Delia brassicae, Delia platura, Delia radicum, Liriomyza huidobrensis, Liriomyza munda, Liriomyza sativae, Liriomyza trifolii, Musca domestics;

[0407] Insects from the order of Thysanoptera e.g. Dichromothrips corbettii, Frankliniella occidentalis, Haplothrips tritici, Scirtothrips citri, Scirtothrips dorsalis, Thrips oryzae, Thrips palmi, Thrips tabaci;

[0408] Insects from the order of Hemiptera e.g. Acyrtosiphon pisum, Amrasca biguttula, Aonidiella au-rantii, Aonidiella citrina, Aphis craccivora, Aphis glycines, Aphis gossypii, Aphis pomi, Bemisia argentifolii, Bemisia tabaci, Brevicoryne brassicae, Cimex lectularius, Dalbulus maidis, Di-aphorina citri, Dichelops furcatus, Dichelops melacanthus, Empoasca bigutulla, Empoasca fa-bae, Empoasca vitis, Euschistus heros, Euschistus servus, Ferrisia virgata, Halyomorpha halys, Laodelphax striatellus, Lycorma delicatula, Lygus hesperus, Lygus lineolaris, Lygus lucorum, Macrosiphum euphorbiae, Mahanarva fimbriolata, Megoura viciae, Myzus persicae, Nephotettix cinctipes, Nephotettix malayanus, Nephotettix virescens, Nezara viridula, Nilaparvata lugens, Pentastiridus leporinus, Piezodorus guildinii, Pseudococcus comstocki, Pseudococcus mariti-mus, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi, Scaphoideus titanus, Schizaphis graminum, Sitobion avenae, Sogatella furcifera, Trialeurodes vaporariorum; Insects from the order of Hymenoptera e.g. Atta laevigata, Camponotus pennsylvanicus, Linepi-thema humile, Solenopsis invicta, Solenopsis xyloni, Tetramorium caespitum;

[0409] Insects from the class of Arachnida e.g.; Brevipalpus chilensis, Brevipalpus lewisi, Brevipalpus phoenicus, Panonychus citri, Panonychus ulmi, Penthaleus major, Phyllocoptruta oleivora, Po-lyphagotarsonemus latus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus urticae, Tetranychus viennensis;241142

[0410] 45

[0411] Pests from the phylum Nematoda e.g. Caenorhabditis elegans, Heterodera glycines, Meloido-gyne chitwoodi, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Pratylen-chus aberrans, Pratylenchus brachyurus, Pratylenchus vulnus.

[0412] Animal health

[0413] The compounds of the invention are suitable for use in treating or protecting animals against infestation or infection by parasites. Therefore, the invention also relates to the use of a compound of the invention for the manufacture of a medicament for the treatment or protection of animals against infestation or infection by parasites. Furthermore, the invention relates to a method of treating or protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of a compound of the invention.

[0414] The invention also relates to the non-therapeutic use of compounds of the invention for treating or protecting animals against infestation and infection by parasites. Moreover, the invention relates to a non-therapeutic method of treating or protecting animals against infestation and infection by parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

[0415] The compounds of the invention are further suitable for use in combating or controlling parasites in and on animals. Furthermore, the invention relates to a method of combating or con-trolling parasites in and on animals, which comprises contacting the parasites with a parasitically effective amount of a compound of the invention.

[0416] The invention also relates to the non-therapeutic use of compounds of the invention for controlling or combating parasites. Moreover, the invention relates to a non-therapeutic method of combating or controlling parasites, which comprises applying to a locus a parasiticidally effective amount of a compound of the invention.

[0417] The compounds of the invention can be effective through both contact (via soil, glass, wall, bed net, carpet, blankets or animal parts) and ingestion (e.g. baits). Furthermore, the compounds of the invention can be applied to any and all developmental stages.

[0418] The compounds of the invention can be applied as such or in form of compositions comprising the compounds of the invention.

[0419] The compounds of the invention can also be applied together with a mixing partner, which acts against pathogenic parasites, e.g. with synthetic coccidiosis compounds, polyetherantibiotics e.g. Amprolium, Robenidin, Toltrazuril, Monensin, Salinomycin, Maduramicin, Lasalocid, Nara-sin or Semduramicin, or with other mixing partners as defined above, or in form of compositions comprising said mixtures.

[0420] The compounds of the invention and compositions comprising them can be applied orally, parenterally or topically, e.g. dermally. The compounds of the invention can be systemically or non-systemically effective.

[0421] The application can be carried out prophylactically, therapeutically or non-therapeutically. Furthermore, the application can be carried out preventively to places at which occurrence of the parasites is expected.

[0422] As used herein, the term "contacting" includes both direct contact (applying the com-pounds / compositions directly on the parasite, including the application directly on the animal or excluding the application directly on the animal, e.g. at its locus for the latter) and indirect241142

[0423] 46

[0424] contact (applying the compounds / compositions to the locus of the parasite). The contact of the parasite through application to its locus is an example of a non-therapeutic use of the compounds of the invention.

[0425] The term "locus" means the habitat, food supply, breeding ground, area, material or environment in which a parasite is growing or may grow outside of the animal.

[0426] As used herein, the term “parasites” includes endo- and ectoparasites. In some embodiments of the invention, endoparasites can be preferred. In other embodiments, ectoparasites can be preferred. Infestations in warm-blooded animals and fish include lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas. The compounds of the invention are especially useful for combating parasites of the following orders and species, respectively:

[0427] fleas (Siphonaptera), e.g. Ctenocephalides felis, C. canis, Xenopsylla cheopis, Pulex irri-tans, Tunga penetrans, and Nosopsyllus fasciatus; cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, B. asahinae, Periplaneta americana, P. japonica, P. brunnea, P. fuligginosa, P. aus-tralasiae, and Blatta orientalis; flies, mosquitoes (Diptera), e.g. Aedes aegypti, A. albopictus, A. vexans, Anastrepha ludens, Anopheles maculipennis, A. crucians, A. albimanus, A. gambiae, A. freeborni, A. leucosphyrus, A. minimus, A. quadrimaculatus, Calliphora vicina, Chrysomya bez-ziana, C. hominivorax, C. macellaria, Chrysops discalis, C. silacea, C. atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, C. nigripalpus, C. quinquefasciatus, C. tarsalis, Culiseta inornata, C. melanura, Dermatobia hominis, Fannia ca-nicularis, Gasterophilus intestinalis, Glossina morsitans, G. palpalis, G. fuscipes, G. tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma line-ata, Lepto-conops torrens, Lucilia caprina, L. cuprina, L. sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, M. stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, P. discolor, Prosimulium mixtum, Sarcophaga spp., S. haemorrhoidalis, Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, T. atratus, T. lineola, and T. similis; lice (Phthiraptera), e.g. Pediculus humanus capitis, P. humanus humanus, Pthirus pubis, Haematopinus euryster-nus, H. suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus, and Solenopotes capillatus; ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, I. holocyclus, I. pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, D. variabilis, Amblyomma americanum, A. maculatum, Ornithodorus hermsi, O. turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti, Dermanyssus gallinae; Actinedida (Prostigmata) and Acaridida (Astigmata), e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demo-dex spp., Trombicula spp., Listrophorus spp., Aca-rus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp; Bugs (Het-eropterida): Cimex lectularius, C. hemip-terus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp., and Arilus critatus; Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.; Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp.; Roundworms Nematoda: Wipeworms and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp.), (Trichuridae) Trichuris spp., Capillaria spp.; Rhabditida, e.g. Rhabditis spp., Strongyloides spp., Helicephalobus spp.; Strongylida, e.g. Strongylus spp.,241142

[0428] 47

[0429] Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Hyostrongulus spp., Haemonchus contortus, Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollu-lanus spp., Chabertia spp., Syngamus trachea, Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp., Aleurostrongylus abstrusus, and Dioctophyma renale; Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia galli, Heterakis spp., Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skrjabinema spp., and Oxyuris equi; Camallanida, e.g. Dracunculus medinensis (guinea worm); Spirurida, e.g. Thelazia spp., Wuchereria spp., Brugia spp., Onchocerca spp., Loa loa, Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.; Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp.; Planarians (Plathelminthes): Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Opisthorchis spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, and Nanocyetes spp.; Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllo-bothrium spp., Taenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp. and Diphyllobothrium latum.

[0430] The term “animal” includes warm-blooded animals (including humans) and fish. Preferred are mammals, e.g. cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals e.g. mink, chinchilla and raccoon, birds e.g. hens, geese, turkeys and ducks and fish e.g. fresh- and salt-water fish e.g. trout, carp and eels. Particularly preferred are domestic animals, e.g. dogs or cats.

[0431] Generally, "parasiticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds / com-positions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions e.g. desired parasiticidal effect and duration, target species, mode of application.

[0432] Generally, it is favorable to apply the compounds of the invention in total amounts of 0.5 mg / kg to 100 mg / kg per day, preferably 1 mg / kg to 50 mg / kg per day.

[0433] For oral administration to warm-blooded animals, the compounds I may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the compounds I may be ad-minis-tered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I, preferably with 0.5 mg / kg to 100 mg / kg of animal body weight per day.

[0434] Alternatively, the compounds I may be administered to animals parenterally, e.g., by intrarumi-nal, intramuscular, intravenous or subcutaneous injection. The compounds I may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the compounds I may be formulated into an implant for subcutaneous administration. In addition the241142

[0435] 48

[0436] compounds I may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg / kg to 100 mg / kg of animal body weight per day of the compounds I.

[0437] The compounds I may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the compounds I. In addition, the compounds I may be formulated as ear tags for animals, particularly quadrupeds e.g. cattle and sheep.

[0438] Suitable preparations are:

[0439] - Solutions e.g. oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pouring-on formulations, gels;

[0440] - Emulsions and suspensions for oral or dermal administration; semi-solid preparations;

[0441] - Formulations in which the active compound is processed in an ointment base or in an oil-in-water or water-in-oil emulsion base;

[0442] - Solid preparations e.g. powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; aerosols and inhalants, and active compound-containing shaped articles.

[0443] Compositions suitable for injection are prepared by dissolving the active ingredient in a suit-able solvent and optionally adding further auxiliaries e.g. acids, bases, buffer salts, preservatives, and solubilizers. Suitable auxiliaries for injection solutions are known in the art. The solutions are filtered and filled sterile.

[0444] Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary. Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on. Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

[0445] Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results. Suitable thickeners are known in the art.

[0446] Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically. Pour-on formulations are prepared by dis-solving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries e.g. colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added. Suitable such auxiliaries are known in the art.

[0447] Emulsions can be administered orally, dermally or as injections. Emulsions are either of the wa-ter-in-oil type or of the oil-in-water type. They are prepared by dissolving the active com-pound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries e.g. colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosityenhancing substances. Suitable hydrophobic phases (oils), suitable hydrophilic phases, suitable emulsifiers, and suitable further auxiliaries for emulsions are known in the art.241142

[0448] 49

[0449] Suspensions can be administered orally ortopically / dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries e.g. wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers. Suitable suspending agents, and suitable other auxiliaries for suspensions including wetting agents are known in the art.

[0450] Semi-solid preparations can be administered orally ortopically / dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

[0451] For the production of solid preparations, the active compound is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form. Suitable auxiliaries for this purpose are known in the art.

[0452] The compositions which can be used in the invention can comprise generally from about 0.001 to 95% of the compound of the invention.

[0453] Ready-to-use preparations contain the compounds acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80% by weight, preferably from 0.1 to 65% by weight, more preferably from 1 to 50% by weight, most preferably from 5 to 40% by weight.

[0454] Preparations which are diluted before use contain the compounds acting against ectoparasites in concentrations of 0.5 to 90% by weight, preferably of 1 to 50% by weight.

[0455] Furthermore, the preparations comprise the compounds of formula I against endoparasites in concentrations of 10 ppm to 2% by weight, preferably of 0.05 to 0.9% by weight, very particularly preferably of 0.005 to 0.25% by weight.

[0456] Topical application may be conducted with compound-containing shaped articles e.g. collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

[0457] Generally it is favorable to apply solid formulations which release compounds of the invention in total amounts of 10 mg / kg to 300 mg / kg, preferably 20 mg / kg to 200 mg / kg, most preferably 25 mg / kg to 160 mg / kg body weight of the treated animal in the course of three weeks.

[0458] A. Preparation Examples

[0459] The compounds were characterized by melting point determination, by NMR spectroscopy or by the mass-to-charge ratio ([m / z]) and retention time (RT; [min.]), as determined by mass spectrometry (MS) coupled with HPLC analysis (HPLC-MS = high performance liquid chromatography-coupled mass spectrometry), LC analysis (LC-MS = liquid chromatography-coupled mass spectrometry) or chiral SFC (SFC = supercritical fluid chromatography).

[0460] HPLC-MS: Shimadzu Nexera UHPLC + Shimadzu LCMS 20-20, ESI, Column: Phenomenex Kinetex 1,7pm XB-C18 100A, 50 x 2,1mm, Mobile Phase: A: water + 0,1% TFA; B:Acetonitrile; Temperature: 60°C, Gradient:5% B to 100% B in 1,50min; 100% B 0,25min, Flow: 0,8ml / min to 1,0ml / min in 1,51 min. MS method: ESI positive. Mass range (m / z): 100-700.

[0461] Synthesis of compound 1-1

[0462] Step 1 : Synthesis of ethyl 3-fluoro-4-nitro-benzenecarboximidate hydrochloride

[0463]

[0464] 241142

[0465] 50

[0466] A round bottom flask was charged with ethanol (8 mL) and cooled to 0°C. Acetyl chloride (3.4 ml_, 3.8 g, 48 mmol, 8 equiv.) was added and the mixture was stirred for 5 min. 3-Fluoro-4-nitroben-zonitrile (1.00 g, 6.02 mmol) was added in small portions and the cooling bath was removed to allow the mixture to warm to room temperature over night. After completed reaction, all volatiles were removed in vacuum and the residue was triturated with diethyl ether. The resulting solid was collected via filtration and dried in vacuum to obtain the title compound (860 mg, 3.46 mmol, 57%) which was used directly in the following step.

[0467] 1H NMR (400 MHz, DMSO-cfe) 5 8.38 - 8.23 (m, 2H), 8.06 (dd, 1H), 7.97 (d, 1H), 7.32 (t, ammonium signal, 2H), 4.38 (q, 2H), 1.35 (t, 3H).

[0468] Step 2: Synthesis of 3-fluoro-4-nitro-N-[4-(trifluoromethoxy)anilino]benzamidine (compound 1-1)

[0469]

[0470] A solution of ethyl 3-fluoro-4-nitro-benzenecarboximidate hydrochloride (0.85 g, 3.42 mmol, 1.00 equiv.) in pyridine (3 mL) was cooled to 0°C and (trifluoromethoxy)phenylhydrazine hydrochloride (0.781 g, 3.419 mmol, 1.000 equiv.) was added. After removal of the cooling bath, the mixture was stirred over night. Water (10 mL) and dichloromethane (10 mL) were added, and the aqueous phase was separated. After extraction of the aqueous phase with dichloromethane (3x10 mL), combined organic layers were washed with saturated aqueous ammonia chloride solution (30 mL), dried over sodium sulphate and evaporated. The residue was subjected to column chromatography on silica gel with ethyl acetate and cyclohexane as eluents to yield the title compound (925 mg, 2.58 mmol, 76%).

[0471] HPLC-MS: Rt (min) = 0.917, m / z: [M+H] = 358.8;1H NMR (400 MHz, CDCI3) 58.13 (dd, 1H), 7.73 (dd, 1H), 7.68 - 7.65 (m, 1H), 7.17 - 7.11 (m, 4H), 6.40 (br. s, 1H), 4.56 (br. s, 2H).

[0472] B. Biological Examples

[0473] If not otherwise specified, the test solutions were prepared as follows:

[0474] The active compound was dissolved at the desired concentration in a mixture of 1 :1 (vol:vol) distilled water:acetone. The test solution was prepared on the day of use.

[0475] The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the following biological tests. Examples for such biological tests include test on their pesticidal activities e.g. on Green peach aphid (Myzus persicae, MYZUPE), Silverleaf whitefly (Bemisia argentifolii), Southern armyworm (Spodoptera eridania), and Tobacco Budworm (Heliothis virescens).

[0476] B.1. Green peach aphid Myzus persicae, MYZUPE) (mixed life stages)

[0477] For evaluating control of Green Peach Aphid through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane. The compounds were formulated using a solution containing 75% v / v water and 25% v / v DMSO.241142

[0478] 51

[0479] Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom-built pipette, at two replications. After application, 5 - 8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23 ± 1°C and about 50 ± 5 % relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.

[0480] In this test, compound 1-1 at 800 ppm showed at least 75% mortality in comparison with untreated controls.

[0481] Comparison of activity with prior art

[0482] Table 1 shows % mortality in comparison to untreated controls.

[0483] Table 1

[0484]

Claims

1. 24114252Claims1. Compounds of formula IwhereinR1ais Ci-C4-alkoxy, Ci-C4-haloalkoxy or halogen;R1bis H or halogen;R2is halogen;and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

2. The compounds of formula I according to claim 1 , wherein R2is F, Cl or Br, preferably wherein R2is F.

3. The compounds of formula I according to any of claims 1 or 2, wherein R1bis H, F, Cl or Br, preferably wherein R1bis H.

4. The compounds of formula I according to any of claims 1 to 3, wherein R1ais OCF3or OCHF2.

5. The compound of formula I according to any of claims 1 to 4, wherein R1ais OCF3, R1bis H and R2is F.

6. A process for the preparation of a compound of formula I according to claims 1 to 5, wherein the process optionally comprises step i)i) reaction of a compound of formula III with a compound of formula II in the presence of a basewherein the process optionally further comprises step ii)ii) an alcohol addition reaction of compound IV in presence of an acid241142537. A process for the preparation of a pesticidal compound, mixture or formulation thereof, comprising a compound of formula I according to claim 1 to 5 preferably as an intermediate compound.

8. A compound of formula I according to claim 1 to 5 for use in a process of preparing a pesticidal compound, mixture or formulation thereof.

9. An agricultural or veterinary composition comprising at least one compound according to any one of claims 1 to 5 and / or at least one agriculturally or veterinarily acceptable salt thereof, and at least one inert liquid and / or solid agriculturally or veterinarily acceptable carrier.

10. An agricultural or veterinary composition comprising at least one compound of formula I and at least one fungicidal, herbicidal and / or insecticidal compound, preferably wherein the weight ratios of the compound of formula I to the fungicidal, herbicidal or insecticidal compound is from 5000: 1 to 1 :5000, further preferably 1 : 100 to 1:1000.

11. An agricultural composition for combating animal pests comprising at least one compound as defined in any of claims 1 to 5 and at least one inert liquid and / or solid acceptable carrier and, if desired, at least one surfactant.

12. A method for combating or controlling invertebrate pests, which method comprises contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound as defined in any one of claims 1 to 5.

13. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water in which the plant is growing, with a pesticidally effective amount of at least one compound as defined in any of claims 1 to 5.

14. Seed comprising a compound as defined in any of claims 1 to 5, or the enantiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

15. A method for treating or protecting an animal from infestation or infection by invertebrate pests which comprises bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I as defined in any of claims 1 to 5, a stereoisomer thereof and / or at least one veterinarily acceptable salt thereof.

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