Isoxazol and acyl hydrazone compounds useful in agriculture and / or in animal health

Abstract

The present invention relates to novel compounds which are useful in agriculture and / or in animal health and / or household and in particular to novel isoxazoline compounds, as well as to compositions comprising these compounds. In addition, the present invention relates to the use of a compound or a composition comprising one or more of these compounds in agriculture or animal health or household and specifically for controlling insect pests or parasitic invertebrate pests or household pests. The present invention further relates to intermediate compounds which are useful in preparing the compounds of the present invention.

Description

[0001] Globachem NV GLB32433PCT

[0002] September 30, 2025

[0003] DESCRIPTION

[0004] ISOXAZOLINE COMPOUNDS

[0005] FIELD OF THE INVENTION

[0006] The present invention relates to novel compounds which are useful in agriculture and / or in animal health and / or household and in particular to novel isoxazoline compounds, as well as to compositions comprising these compounds. In addition, the present invention relates to the use of a compound or a composition comprising one or more of these compounds in agriculture or animal health or household and specifically for controlling insect pests or parasitic invertebrate pests or household pests. The present invention further relates to intermediate compounds which are useful in preparing the compounds of the present invention.

[0007] BACKGROUND OF THE INVENTION

[0008] In view of the increasing world population and the associated increased demand for nourishments, the productivity of cultivated growth needs to be improved. Yet, environmental influences on cultivation, such as soil pests, can considerably influence agricultural harvest. For example, there is hardly any cultivated plant that is not attacked by at least one type of insect pest. Thus, there is a constant need for novel pesticidally active compounds which should however also exhibit a favourable environmentally profiles towards non-target organisms, such as humans and aquatic organisms.

[0009] The present invention therefore aims the provision of pesticidally active compounds and to compositions thereof which are useful in agriculture and / or in animal health. In particular, the present invention aims to provide novel compounds which are active against insect pests damaging crops, and which therefore can be used as agricultural agent and in methods of controlling these animal pests. Furthermore, the present invention also aims the provision of compounds which are active against parasitic invertebrate pests and can be used in animal health.

[0010] Due to the increasing urban densification, the present invention also aims at the provision of compounds which are active against arthropod pest.

[0011] Pesticidal active ingredients with an isoxazoline moiety are known from, for example, WO 2005 / 085216 Al and CN 114380762 A, but there is a need for compounds having improved biological performance. Improvements in biological performance may allow the active ingredients to be applied in reduced dose rates, thereby increasing safety and reducing cost. SUMMARY OF THE INVENTION

[0012] The present invention is based on the finding that at least one of the above objects can be solved by novel compounds that inter alia contain an isoxazoline core and an acyl hydrazone moiety.

[0013] Specifically, according to a first aspect of the invention, the present invention provides a compound that corresponds to the following Formula (1)

[0014] Formula (1) wherein

[0015] A is Ci-haloa Ikyl;

[0016] Q is selected from aryl, and heteroaryl;

[0017] R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;

[0018] R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; and

[0019] R2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0020] In a second aspect, the present invention provides a compound that corresponds to the following Formula (I), or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer, a rotamer or a deuterated compound thereof: Formula (I) wherein

[0021] A is selected from CF3 and CHF2;

[0022] Q is selected from aryl and heteroaryl; and

[0023] R is selected from aryl and heteroaryl.

[0024] In a third aspect, the present invention provides a composition comprising a compound according to the first or second aspect. In a fourth aspect, the present invention provides the use of the compound according to the first or second aspect or the composition according to the third aspect in agriculture or in animal health or in household, and in particular in controlling insect pests or in controlling parasitic invertebrate pests or in controlling household pests.

[0025] In a fifth aspect, the present invention provides a method for controlling insect pests which comprises applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of a compound according to the first or second aspect or a composition according to the third aspect.

[0026] In a sixth aspect, the present invention provides the use of a compound of Formula (1):

[0027] Formula (1) in controlling household pest, wherein

[0028] A is Ci-haloa Ikyl;

[0029] Q is selected from aryl and heteroaryl;

[0030] R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;

[0031] R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0032] In a seventh aspect, the present invention provides an intermediate of Formula (10):

[0033] Formula (10) wherein

[0034] A is Ci-haloa Ikyl;

[0035] Q is selected from aryl and heteroaryl;

[0036] R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; and R2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof, which are useful in the preparation of a compound according to the first or second aspect such as compounds of the following formulae:

[0037]

[0038] In an eighth aspect, the present invention provides the use of a compound of the seventh aspect in the preparation of a compound according to the first or second aspect.

[0039] In a ninth aspect, the present invention provides a compound according to the first or second aspect or a composition according to the third aspect which has improved human and / or environmentally profiles compared to other products used to control insect pests and / or parasitic invertebrate pests and / or household pests.

[0040] DEFINITIONS

[0041] In the present disclosure, the following definitions are applicable.

[0042] The term "Ci-Cmalkyl" (alternatively Ci-malkyl) as used herein refers to a saturated straightchain or branched hydrocarbon radical attached via any of the carbon atoms having one to m carbon atoms, for example, any one of the radicals methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1- dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-l-methylpropyl, or l-ethyl-2-methylpropyl, but are not limited thereto. The term "haloalkyl" as used herein denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms, frequently 1 to 6, or 1 to 5, or 1 to 4, or 1 to 3, or 1 or 2 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from Ci-Ce haloalkyl, more preferably from C1-C3 haloalkyl or C1-C2 haloalkyl, in particular from Ci-Cm2-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 6 carbon atoms, preferably 1 to 4, or 1 to 2 carbon atoms, more preferably 1 carbon atom. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyl oxy, isobutyloxy, tert-butyloxy, and the like. The term "haloalkoxy" as used herein denotes in each case an alkoxy, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.

[0044] The term "alkenyl" as used herein denotes in each case an unsaturated hydrocarbon group having usually 2 to 6, preferably 2 to 4 carbon atoms comprising at least one carbon-carbon double bond in any position, e.g. vinyl (ethenyl), allyl (2-propen-l-yl), 1-propen-l-yl,

[0045] 2-propen-2-yl, methallyl (2-methylprop-2-en-l-yl), 2-buten-l-yl, 3-buten-l-yl, 2-penten-l-yl,

[0046] 3-penten-l-yl, 4-penten-l-yl, l-methylbut-2-en-l-yl, 2-ethylprop-2-en-l-yl and the like. If geometric isomers are possible with regard to the double bond, the present invention relates to both, the E- and Z-isomers. The bonding of vinyl is exemplified below:

[0047] The term "alkynyl" as used herein denotes in each case an unsaturated hydrocarbon group having usually 2 to 6, preferably 2 to 4 carbon atoms comprising at least one carbon-carbon triple bond in any position, e.g. ethynyl.

[0048] Aryl and heteroaryl are aromatic ring structures, whereby heteroaryl refers to an aromatic ring structure including one or more heteroatoms independently selected from, for example, N, O and S.

[0049] The term "carbocyclic" or "carbocyclyl" includes, unless otherwise indicated, in general a 3- to 9-membered, preferably a 4- to 8-membered or a 3- to 6-membered or a 5- to 7-membered, more preferably a 5- or 6-membered monocyclic or bicyclic ring comprising 3 to 9, preferably 4 to 8 or 3 to 6 or 5 to 7, more preferably 5 or 6 carbon atoms. The carbocyclyl ring may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. The term "carbocyclyl", unless otherwise indicated, may therefore cover inter alia cycloalkyl, cycloalkenyl, as well as phenyl. Preferably, the term "carbocyclyl" covers cycloalkyl and cycloalkenyl groups, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl ring moieties. The term "cycloalkyl" as used herein denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 10 or from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl or cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "halocycloalkyl" as used herein denotes in each case a cycloalkyl, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms.

[0050] Suitably, the term "aryl" as used herein includes 5- to 9-membered aromatic carbocyclic rings based on carbon atoms as ring members. Preferred examples are phenyl or naphthyl. Unless otherwise indicated, the term "aryl" further covers "aromatic carbobicycles" such as naphthyl.

[0051] As used herein, the terms "carbocyclylalkyl" such as "cyclopropylalkyl" as well as "phenylalkyl" and the like refer to the corresponding groups, which are bonded to the remainder of the molecule via an alkylene, preferably via a Ci-C4-alkylene group. Examples include but are not limited to benzyl (i.e. phenylmethyl), cyclohexylmethyl, pyridinylmethyl, and piperidinomethyl.

[0052] As used herein, the term "alkylene" refers to a linking straight-chain or branched alkylene group having usually from 1 to 4 carbon atoms, e.g. 1, 2, 3, or 4 carbon atoms. The alkylene group bridges a certain group to the remainder of the molecule. Preferred alkylene groups include methylene (CH2), ethylene (CH2CH2), propylene (CH2CH2CH2) and the like. A skilled person understands that, if it is referred, e.g., to CH2 that the carbon atom being tetravalent has two valences left for forming a bridge (-CH2-). Similarly, when it is referred, e.g., to CFUCI-h, each carbon atom has one valence left for forming a bridge (-CH2CH2-). Furthermore, when it is referred, e.g., to CH2CH2CH2, each terminal carbon atom has one valence left for forming a bridge (-CH2CH2CH2-).

[0053] The term "heterocyclic" or "heterocyclyl" includes, unless otherwise indicated, in general a 3- to 9-membered, preferably a 4- to 8-membered or 5- to 7-membered, more preferably 5-or 6-membered, in particular 6-membered monocyclic or bicyclic ring. The heterocycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. The heterocycle typically comprises one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. The remaining ring members are carbon atoms. In some embodiment, the heterocycle is an aromatic heterocycle, preferably a 5- or 6-membered aromatic heterocycle comprising one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. Examples of aromatic heterocycles are provided below in connection with the definition of "hetaryl". "Hetaryls" or "heteroaryls" are covered by the term "heterocycles". The saturated or partially or fully unsaturated heterocycles usually comprise 1, 2, 3, 4 or 5, preferably 1, 2 or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. The skilled person is aware that S, SO or SO2 is to be respectively understood as follows:

[0054] Further, a skilled person is aware that resonance structures of the oxidized forms may be possible. Saturated heterocycles include, unless otherwise indicated, in general 3- to 9-membered, preferably 4- to 8-membered or 5- to 7-membered, more preferably 5- or 6-membered monocyclic rings comprising 3 to 9, preferably 4 to 8 or 5 to 7, more preferably

[0055] 5 or 6 atoms comprising at least one heteroatom, such as pyrrolidine, tetrahydrothiophene, tetrahydrofuran, piperidine, tetrahydropyran, dioxane, morpholine or piperazine.

[0056] The term "heterobicyclic" or "heterobicyclyl" includes, unless otherwise indicated, in general

[0057] 6 to 14-membered, preferably 7- to 12-membered or 8- to 10-membered, more preferably 9- or 10-membered bicyclic rings. The heterobicycle may be saturated, partially or fully unsaturated, or aromatic, wherein saturated means that only single bonds are present, and partially or fully unsaturated means that one or more double bonds may be present in suitable positions, while the Huckel rule for aromaticity is not fulfilled, whereas aromatic means that the Huckel (4n + 2) rule is fulfilled. In principal, for being "aromatic", it is sufficient if one of the two rings of the bicyclic moieties is aromatic, while the other is non-aromatic. However, it is preferred in connection with the term "aromatic" that both rings of the bicyclic moiety are aromatic, so that, e.g., 8 n electrons are present in case of a 9- or 10-membered aromatic heterobicyclic ring. The heterobicycle typically comprises one or more, e.g. 1, 2, 3, or 4, preferably 1, 2, or 3 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO2. The remaining ring members are carbon atoms. Examples of heterobicycles include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, quinolinyl, isoquinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl, pyridoimidazolyl, triethylenediamine or quinuclidine and the like. Preferred heterobicycles according to the invention are aromatic heterobicycles such as benzodiazole, benzoxazole, benzothiazole, ethylenedioxythiophene, benzothiadiazole (e.g., 1,2,3-benzothiadiazole or 2,1,3-benzothiadiazole), quinoline, and iso-quinoline.

[0058] Suitably, the term "heteroaryl" as used herein includes monocyclic 5- or 6-membered aromatic heterocycles comprising as ring members 1, 2, 3 or 4 heteroatoms selected from N, O and S, where S-atoms as ring members may be present as S, SO or SO2. Examples of 5- or 6-membered aromatic heterocycles include pyridyl (also referred to as pyridinyl), i.e. 2-, 3-, or 4-pyridyl, pyrimidinyl, i.e. 2-, 4- or 5-pyrimidinyl, pyrazinyl, pyridazinyl, i.e. 3- or 4- pyridazinyl, thienyl, i.e. 2- or 3-thienyl, furyl, i.e. 2-or 3-furyl, pyrrolyl, i.e. 2- or 3-pyrrolyl, oxazolyl, i.e. 2-, 3- or 5-oxazolyl, isoxazolyl, i.e. 3-, 4- or 5-isoxazolyl, thiazolyl, i.e. 2-, 3- or 5- thiazoly I, 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-[l,3,4]oxadiazolyl, 4- or 5-(l,2,3-oxadiazol)yl, 3- or 5-(l,2,4-oxadiazol)yl, 2- or 5- (l,3,4-thiadiazol)yl, thiadiazolyl, e.g. 2- or 5- (l,3,4-thiadiazol)yl, 4- or 5-(l,2,3-thiadiazol)yl, 3- or 5-(l,2,4-thiadiazol)yl, triazolyl, e.g. 1H-, 2H- or 3H-l,2,3-triazol-4-yl, 2H-triazol-3-yl, 1H-, 2H-, or 4H-l,2,4-triazolyl and tetrazolyl, i.e. 1H- or 2H-tetrazolyl. Unless otherwise indicated, the term "hetaryl" further covers "aromatic heterobicycles" as defined above. The skilled person is aware that S, SO or SO2 is to be respectively understood as follows:

[0059] Halogen is generally fluorine (F also referred to as fluoro), chlorine (Cl also referred to as chloro), bromine (Br also referred to as bromo) or iodine (I also referred to as iodo).

[0060] The term "optionally substituted" as used herein means that the group referenced is either unsubstituted or is substituted by one or more substituents. For example, "C1-C3 alkyl is optionally substituted with one or two F" means a group selected from C1-C3 alkyl, C1-C3 alkyl substituted with one F, and C1-C3 alkyl substituted with two F.

[0061] Unless specified otherwise, the term "substituted" as used herein means substitution by any of the above or other groups (e.g., alkyl, alkylene, alkylcycloalkyl, alkoxy, alkylphosphoryl, alkylphosphorylaminyl, amidinylalkyloxy, guanidinylalkyloxy, alkylcarbonylaminylalkyloxy, heterocyclylalkyloxy, heteroarylalkyloxy, aminylalkyloxy, alkoxyalkyl, alkoxycarbonyl, haloalkylaminyl, hydroxylalkylaminyl, amidinylalkylaminyl, guanidinylalkylaminyl, aminylalkyl, aminylalkylaminyl, aminylalkoxy, alkylaminylalkoxy aryloxy, alkylaminyl, alkylcarbonylaminyl, alkylaminylalkyl, aminylcarbonyl, alkylaminylcarbonyl, alkylcarbonylaminylalkoxy, aminylcarbonylalkyl, aminylcarbonycycloalkylalkyl, thioalkyl, aryl, aralkyl, arylalkyloxy, arylalkylaminyl, carboxyalkyl, cyanoalkyl, cycloalkyl, cycloalkyloxy, cycloalkylaminyl, cyanocycloalkyl, cycloalkylaminylcarbonyl, cycloalkylalkyl, haloalkyl, haloalkoxy, heterocyclyl, heterocyclyloxy, heterocyclylaminyl, / V-heterocyclyl, heterocyclylalkyl, heterocyclylalkyloxy, heterocyclylalkylaminyl, heteroaryl, / V-heteroaryl, heteroarylalkyl, heteroarylalkyloxy, heteroarylalkylaminyl, hydroxylalkylaminyl, phosphoalkoxy and / or hydroxylalkyl) wherein at least one hydrogen atom (e.g., 1, 2, 3 or more or all hydrogen atoms) is replaced by a bond to a non-hydrogen atom such as, but not limited to: a halogen atom such as F, Cl, Br, and I; an oxygen atom in groups such as hydroxyl groups, alkoxy groups, and ester groups; a sulfur atom in groups such as thiol groups, thioalkyl groups, sulfonyl groups, and sulfoxide groups; a nitrogen atom in groups such as amines, amides, alkylamines, dialkylamines, arylamines, alkylarylamines, diarylamines, / V-oxides, imides, and enamines; a silicon atom in groups such as trialkylsilyl groups, dialkylarylsilyl groups, alkyldiarylsilyl groups, and triarylsilyl groups; and other heteroatoms in various other groups. "Substituted" also means any of the above groups in which one or more hydrogen atoms are replaced by a higher-order bond (e.g., a double- or triple-bond) to a heteroatom such as oxygen in oxo, carbonyl, carboxyl, and ester groups; and nitrogen in groups such as imines, oximes, hydrazones, and nitriles. For example, "substituted" includes any of the above groups in which one or more hydrogen atoms are replaced with -NRgRh, -NRgC(=O)Rh, -NRgC(=O)NRgRh, -NRgC(=O)ORh, -NRgSO2Rh, -OC(=O)NRgRh, -ORg, - SRg, -SORg, -SChRg, -OSChRg, -SChORg, =NSO2Rg, and -SChNRgRh. "Substituted" also means any of the above groups in which one or more hydrogen atoms are replaced with -C(=O)Rg, -C(=O)ORg, -C(=O)NRgRh, -CI- SChRg, -CI- SChNRgRh. In the foregoing, Rgand Rh are the same or different and independently hydrogen, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, / V-heterocyclyl, heterocyclylalkyl, heteroaryl, / V-heteroaryl and / or heteroarylalkyl. "Substituted" further means any of the above groups in which one or more hydrogen atoms are replaced by a bond to an aminyl, cyano, hydroxyl, imino, nitro, oxo, thioxo, halo, alkyl, alkoxy, alkylaminyl, thioalkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, haloalkyl, heterocyclyl, / V-heterocyclyl, heterocyclylalkyl, heteroaryl, / V-heteroaryl and / or heteroarylalkyl group. In addition, each of the foregoing substituents may also be optionally substituted with one or more of the above substituents.

[0062] In a chemical structure, indicates a double bond between two atoms which may either finally relate to the (E)- or (Z)-isomer as the absolute stereochemistry thereof.

[0063] In a chemical structure, indicates an attachment point to the remainder of a compound.

[0064] As used herein, the term "agrochemically acceptable salt" refers to a salt which can be applied as an agrochemical.

[0065] The term "stereoisomer" as used herein includes any enantiomer, diastereomer, geometric isomer (E / Z) or tautomer of a given compound.

[0066] The term "tautomer" refers to a structural isomer of a given compound that is readily interconverted by tautomerization. It commonly results from the relocation of a hydrogen atom within the compound.

[0067] The term "rotamer" is used for any of a number of isomers of a molecule that can be interconverted by rotation of part of the molecule around a particular bond.

[0068] The term "N-oxide" includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to a N-oxide moiety.

[0069] As used herein, the term "controlling" refers to reducing the number of pests, eliminating pests and / or preventing further pest damage such that damage to a plant or to a plant derived product or to (non-)foodstuff is reduced.

[0070] As used herein, the term "insecticide" refers to an active ingredient that kills, controls or otherwise inhibits insects affecting the growth of plants. The preferred amount or concentration of the insecticide is an "effective amount" or "effective concentration".

[0071] As used herein, the term "effective amount" or "effective concentration" refers to the amount or the concentration of the compound, or a salt thereof, which, upon single or multiple applications, provides the desired effect. An effective amount is readily determined by the skilled person in the art, by the use of known techniques and by observing results obtained under analogous circumstances. In determining the effective amount, a number of factors are considered including, but not limited to: the type of plant or derived product to be applied; the pest to be controlled and its lifecycle; the particular compound applied; the type of application; and other relevant circumstances.

[0072] In each of the following aspects and embodiments of the invention, "consisting essentially" and inflections thereof are a preferred embodiment of "comprising" and its inflections, and "consisting of" and inflections thereof are a preferred embodiment of "consisting essentially of" and its inflections.

[0073] DETAILED DESCRIPTION OF THE INVENTION

[0074] Embodiments according to the invention are provided as set out below. The disclosure in the present application makes available each and every combination of these embodiments disclosed in the following.

[0075] 1. A compound of Formula (1):

[0076] Formula (1) wherein

[0077] A is Ci-haloa Ikyl;

[0078] Q is selected from aryl and heteroaryl;

[0079] R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;

[0080] R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; and

[0081] R2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0082] 2. A compound according to the following Formula (I): Formula (I) wherein

[0083] A is selected from CF3 and CHF2;

[0084] Q is selected from aryl and heteroaryl; and R is selected from aryl and heteroaryl; or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer, a rotamer or a deuterated compound thereof. The compound of item 1 or 2, wherein Q is substituted or unsubstituted aryl and preferably naphthyl or phenyl, more preferably Q is phenyl. The compound of any of items 1 to 3, wherein R is substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. The compound of any of items 1-4, wherein Q is naphthyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen, more preferably substituted with methyl, ethyl, fluorine or chlorine, and even more preferably Q is selected from the following moieties: whereinfindicates the attachment points to the remainder of the compound of Formula (I). The compound of any of items 1-5, wherein R is unsubstituted or substituted with one or more substituents selected from halogen, preferably fluorine, nitrile and C1-3 alkyl, preferably methyl. The compound of any of items 1-6, wherein R is selected from the following moieties: The compound of any of items 1-7, wherein A is CF3. The compound of any of items 1-8 which conforms to the following Formula (la): Formula (la), wherein A, Q and Rare defined as in any of items 1-8. 10. The compound of any of items 1-9 which is selected from the following compounds:

[0085] A composition comprising a compound according to any of items 1-10, one or more auxiliaries and / or adjuvants, and optionally one or more other active ingredients. The composition of item 11 which is an agrochemical and / or parasitic composition and / or household composition. Use of a compound according to any of items 1-10 or a composition according to item 11 or 12 in agriculture or in animal health or in household. 14. Use of a compound according to item 13 in controlling insect pests or parasitic invertebrate pests or household pests.

[0086] 15. The use according to item 13 or 14, wherein the insect pest is selected from lepidopteran, hemipteran, coleopteran, thysanopteran and dipteran and other invertebrate pest species preferably from the Lepidopteran pests and preferably the insect pest is selected from Spodoptera, Plutella and Helicoverpa damaging crops.

[0087] 16. The use according to item 13 or 14, wherein the parasitic invertebrate pest is selected from the parasitic invertebrate pests such as fleas, ticks and mites.

[0088] 17. A method for controlling insect pests which comprises applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of a compound as defined in any of items 1-10 or a composition as defined in item 11 or 12.

[0089] 18. An intermediate of Formula (10):

[0090] Formula (10) wherein

[0091] A is Ci-haloa Ikyl;

[0092] Q is selected from aryl and heteroaryl;

[0093] R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; and

[0094] R2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof. 19. The intermediate according to item 18, wherein the formula (10) has any one of the following formulae: any of items 1-10.

[0095] 21. A compound of any of item 1-10 or a composition according to item 11 or 12 which has improved human and / or environmentally profiles compared to other products used to control insect pests and / or parasitic invertebrate pests and / or household pests.

[0096] 22. Use of a compound of Formula (1):

[0097] Formula (1) in controlling household pest, wherein

[0098] A is Ci-haloa Ikyl;

[0099] Q is selected from aryl and heteroaryl;

[0100] R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;

[0101] R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0102] COMPOUNDS OF FORMULAE (1) AND (I)

[0103] According to a first aspect of the invention, there is provided a compound of Formula (1):

[0104] Formula (1) wherein A is Ci-haloalkyl; Q is selected from aryl and heteroaryl; R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl; R1, R3are each independently selected from hydrogen, halogen, and Ci-haloalkyl; and R2is selected from halogen and Ci- haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0105] The person skilled in the art will appreciate that the condition "or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3" reflects the possibility of R2being H in the event that R3is Ci-haloalkyl or hydrogen and / or in the event that A is not CF3. The condition, however, does not require that R2must be hydrogen in the event that R3is Ci-haloalkyl or hydrogen and / or in the event that A is not CF3.

[0106] According to a further aspect of the invention, there is provided a compound of Formula (1):

[0107] Formula (1) wherein A is Ci-haloalkyl; Q is selected from aryl and heteroaryl; R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl; R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-haloalkyl; and wherein when R2is hydrogen, R1and R3are chlorine and A is CF3, R is not 4-fluorophenyl,

[0108] 3-fluorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 2, 4, 6-trifluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3,4,5-trifluorophenyl,

[0109] 4-bromophenyl, 2-bromophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl,

[0110] 4-cyanophenyl, 3-cyanophenyl, 2-cyanophenyl or 2-pyridyl; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0111] According to a further aspect of the invention, there is provided a compound of Formula (1):

[0112] Formula (1) wherein A is Ci-haloalkyl; Q is selected from aryl and heteroaryl; R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl; R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-haloalkyl; wherein the compound of Formula (1) is not selected from or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0113] In the following, embodiments for Formula (1) are outlined. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0114] In some embodiments, A is selected from CF3, CHF2, and CCIF2, preferably from CF3 and CHF2.

[0115] In preferred embodiments, A is CF3. In other preferred embodiments, A is CHF2.

[0116] In preferred embodiments, at least one of R1, R2, R3is not hydrogen.

[0117] In some embodiments, R1, R3are each independently selected from hydrogen, halogen, and CF3.

[0118] In some embodiments, R2is hydrogen when R3is Ci-haloa Ikyl or hydrogen, or when A is CHF2, CH2F, CCI3or CCIF2. In some embodiments, R2is selected from halogen and CF3, or R2is hydrogen when R3is CF3 or hydrogen, or when A is CHF2.

[0119] In some embodiments, when R2is hydrogen, R1and R3are chlorine and A is CF3, R is not 4-fluorophenyl, 3-fluorophenyl, 2-fluorophenyl, 2,4-difluorophenyl, 2,3,4-trifluorophenyl, 2,3-difluorophenyl, 2, 4, 6-trifluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 3,4,5-trifluorophenyl, 4-bromophenyl, 2-bromophenyl, 4-chlorophenyl, 3-chlorophenyl, 2-chlorophenyl, 4-cyanophenyl, 3-cyanophenyl, 2-cyanophenyl or 2-pyridyl.

[0120] In some embodiments, R1, R3are Cl and R2is hydrogen.

[0121] In some embodiments, compound of Formula (1) is not selected from ln some embodiments, R1is Cl, R2is F, and R3is CF3.

[0122] In some embodiments, R1, R2are Cl, and R3is CF3.

[0123] In some embodiments, R1is Cl, R2is hydrogen, and R3is CF3. According to a second aspect of the invention, there is provided a compound of Formula (I): Formula (I) wherein A is selected from CF3 and CHF2; Q is selected from aryl and heteroaryl; and R is selected from aryl and heteroaryl.

[0124] In the following, embodiments for Formulae (1) and (I) are outlined. It is to be understood that each embodiment is relevant on its own as well as in combination with other embodiments.

[0125] The aryl or heteroaryl for Q may be optionally substituted with one or more substituents. Suitable substituents include an alkyl group such as methyl or ethyl and halogen such as fluorine or chlorine but are not limited thereto. The person skilled in the art appreciates that moiety Q comprises one bond to C=O(NH)NHR and one bond to the isoxazoline moiety.

[0126] The aryl or heteroaryl for R may be optionally substituted with one or more substituents. Suitable substituents include nitrile (CN, also referred to as cyano), a C1-3 alkyl group such as methyl and halogen such as fluorine or chlorine but are not limited thereto.

[0127] In a preferred embodiment, Q is naphthyl or phenyl, which are each independently and optionally substituted with one or more substituents each independently selected from Ci-Ce alkyl group, Ci-Ce haloalkyl group, Ci-Ce alkoxy group, Ci-Ce haloalkoxy group, nitro, cyano, NH2, carbocyclyl, and halogen, preferably selected from C1-C3 alkyl group, C1-C3 haloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, nitro, cyano, NH2, monocyclic carbocyclyl such as cycloalkyl, and halogen, more preferably selected from chloro, bromo, fluoro, iodo, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, nitro, cyano, and cyclopropyl, such as selected from chloro, bromo, fluoro, iodo, methyl, and cyano, and in particular methyl.

[0128] In a preferred embodiment, Q is wherein

[0129] Y1, Y2and Y3are each independently CH or nitrogen;

[0130] R4is hydrogen, halogen, cyano, nitro, NH2, C1-C2 alkyl, C1-C2 haloalkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy, preferably F, Cl, Br, cyano, methyl, Ci haloalkyl, methoxy, Ci haloalkoxy; and indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I).

[0131] In a preferred embodiment, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula

[0132] (I) or the compound of Formula (I).

[0133] That is, the compound of Formula (1) or the compound of Formula (I) may for example correspond to one of the following compounds of Formula (A), (B), (C), (D), (E), (F), (G), (H),

[0134] (J) and (K):

[0135] Formula (A) Formula (B)

[0136]

[0137] The person skilled in the art appreciates that Formulae (G), (H), (J), and (K) are not encompassed by compound of Formula (I).

[0138] In a preferred embodiment, Q is substituted or unsubstituted aryl and preferably naphthyl or phenyl, more preferably Q is phenyl. In a further preferred embodiment, Q is naphthyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen, more preferably substituted with methyl, ethyl, fluorine or chlorine, and even more preferably Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (I). That is, the compound of Formula (I) may for example correspond to one of the following compounds of Formula (A), (B), (C) or (D):

[0139] Formula (C) Formula (D)

[0140] In preferred embodiments, R is unsubstituted or substituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, thiadiazole, benzothiazole, benzoxazole, ethylenedioxythiophene, benzothiadiazole (e.g. 1,2,3-benzothiadiazole or 2,1,3-benzothiadiazole), tetrahydropyran, tetrahydrothiopyran, 1,1-dioxothiane, or tetrahydrofuran, preferably substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole (e.g. 1,2,3-benzothiadiazole) or thiadiazole, more preferably substituted or unsubstituted phenyl, pyridine, furane, oxazole, thiazole, or pyrimidine.

[0141] The person skilled in the art appreciates that moiety R comprises one bond to the remainder of the molecule. Thus, when referring to exemplarily pyridine as substituent, it is referred to the pyridyl, which can optionally be substituted.

[0142] In another preferred embodiment, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. In one preferred embodiment, R is unsubstituted or substituted with one or more substituents selected from halogen, which is preferably fluorine, nitrile and C1-3 alkyl, which is preferably methyl.

[0143] In some embodiments, R is unsubstituted or substituted with one or more substituents independently selected from halogen, nitrile, nitro, C1-3 alkyl, C1-3 ha loalkyl, C1-3 alkoxy, C1-3 haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, NHSO2-C1-3 alkyl, NH-C1-3 alkyl, N(CI-3 a lkyl)2, NH-C1-3 haloalkyl, NHC(O)-CI-3alkyl, S-C1-3 alkyl, S-C1-3 haloalkyl, SO2NH2, SO2-C1.3 alkyl, S(O)(NH)Me, S(O)Me(N(CN)), C(O)Me(N(CN)), hydroxyl, C(O)NH-CI-3alkyl, C(O)NH2, cycloalkyl, and heterocyclyl, preferably selected from F, Cl, Br, I, nitrile, nitro, methyl, CHF2, CMeF2, OMe, OCHF2, vinyl, ethynyl, NHSO2Me, NHMe, NMe2, NHCF3, NHC(O)Me, SMe, SCF3, SO2NH2, SChMe, S(O)(NH)Me, S(O)Me(N(CN)), hydroxyl, C(O)NHMe, C(O)NH2, cyclopropyl, pyrimidyl, and pyrazolyl. In some embodiments, R is unsubstituted or substituted with one or more substituents independently selected from halogen, nitrile, nitro, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 haloalkoxy, and heterocyclyl, preferably selected from F, Cl, nitrile, nitro, methyl, OMe, and pyrazolyl.

[0144] Suitably, R is selected from phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole (e.g. 1,2,3-benzothiadiazole) or thiadiazole, more preferably substituted or unsubstituted phenyl, pyridine, furane, oxazole, thiazole, or pyrimidine, wherein R is unsubstituted or substituted with one or more substituents independently selected from halogen, nitrile, nitro, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 haloalkoxy, and heterocyclyl, preferably selected from F, Cl, nitrile, nitro, methyl, OMe, and pyrazolyl.

[0145] For example, R may preferably be selected from the following moieties R-1 to R-43:

[0146] For example, R may preferably be selected from the following moieties R-1 to R-118:

[0147]

[0148] R-1 16 R-1 17 R-1 18

[0149] In some embodiments, R may preferably be selected from the following moieties (also referred to as R-A):

[0150] R-115 R-116 R-117 R-118

[0151] In some embodiments, R may preferably be selected from the following moieties (also referred to as R-B):

[0152] In yet another preferred embodiment, A is CF3.

[0153] In yet another preferred embodiment, A is CHF2.

[0154] In an exemplary embodiment, in the compound of Formula (1) or the compound of Formula (I), Q is aryl and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. Preferably, Q is naphthyl or phenyl and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. More preferably, Q is phenyl and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole.

[0155] In another embodiment, Q is aryl and R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl. Preferably, Q is naphthyl or phenyl and R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl. More preferably, Q is phenyl and R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl.

[0156] For example, in one preferred embodiment, Q is aryl and R is fluorine or methyl. More preferably, Q is naphthyl or phenyl and R is fluorine or methyl. Even more preferably, Q is phenyl and R is fluorine or methyl.

[0157] In another preferred embodiment, Qis aryl and R is selected from R-l to R-43 as shown above.

[0158] In another preferred embodiment, Q is unsubstituted or substituted aryl and R is selected from R-l to R-118 as shown above.

[0159] In another preferred embodiment, Q is unsubstituted or substituted aryl and R is selected from any of R-A as shown above. In another preferred embodiment, Q is unsubstituted or substituted aryl and R is selected from any of R-B as shown above.

[0160] More preferably, Q is naphthyl or phenyl and R is selected from any of R-l to R-43. Even more preferably, Q is phenyl and R is selected from any of R-l to R-43.

[0161] More preferably, Q is unsubstituted or substituted naphthyl or phenyl and R is selected from any of R-l to R-118. Even more preferably, Q is unsubstituted or substituted phenyl and R is selected from any of R-A as shown above, preferably of any of R-B as shown above.

[0162] In another preferred embodiment, Q is phenyl which is substituted with a Ci-Ce alkyl group or halogen and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole.

[0163] In other preferred embodiments, Q is naphthyl or phenyl, which are each independently and optionally substituted with one or more substituents each independently selected from Ci-Ce alkyl group, Ci-Ce haloalkyl group, Ci-Ce alkoxy group, Ci-Ce haloalkoxy group, nitro, cyano, NH2, carbocyclyl, and halogen, preferably selected from C1-C3 alkyl group, C1-C3 haloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, nitro, cyano, NH2, monocyclic carbocyclyl such as cycloalkyl, and halogen, more preferably selected from chloro, bromo, fluoro, iodo, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, nitro, cyano, and cyclopropyl, such as selected from chloro, bromo, fluoro, iodo, methyl, and cyano, and R is unsubstituted or substituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, thiadiazole, benzothiazole, benzoxazole, ethylenedioxythiophene, benzothiadiazole (e.g. 1,2,3-benzothiadiazole or 2,1,3-benzothiadiazole), tetra hydropyran, tetrahydrothiopyran, 1,1-dioxothiane, or tetrahydrofuran, preferably substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole (e.g. 1,2,3-benzothiadiazole) or thiadiazole, more preferably substituted or unsubstituted phenyl, pyridine, furane, oxazole, thiazole, or pyrimidine.

[0164] In a preferred embodiment, Q is wherein Y1, Y2and Y3are each independently CH or nitrogen; R4is hydrogen, halogen, cyano, nitro, NH2, C1-C2 a Ikyl, C1-C2 haloalkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy; and indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I) and R is substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, imidazole, thiazole, thiadiazole, benzothiazole, benzoxazole, ethylenedioxythiophene, benzothiadiazole, tetrahydropyran, tetrahydrothiopyran, 1,1-dioxothiane, tetrahydrofuran, or pyrazole, preferably substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole (e.g. 1,2,3-benzothiadiazole) or thiadiazole. In some embodiments, R is substituted with one or more substituents selected from halogen, nitrile, nitro, methyl, OMe, and pyrazolyl, preferably selected from selected from F, Cl, nitrile, nitro, methyl, OMe, and pyrazolyl.

[0165] In a preferred embodiment, Q is selected from the following moieties: unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, imidazole, thiazole, thiadiazole, benzothiazole, benzoxazole, ethylenedioxythiophene, benzothiadiazole, tetrahydropyran, tetrahydrothiopyran, 1,1-dioxothiane, tetra hydrofuran, or pyrazole, preferably substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole (e.g. 1,2,3-benzothiadiazole) or thiadiazole. In some embodiments, R is substituted with one or more substituents selected from halogen, nitrile, nitro, methyl, OMe, and pyrazolyl, preferably selected from selected from F, Cl, nitrile, nitro, methyl, OMe, and pyrazolyl.

[0166] In another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen and R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine and R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl.

[0167] In another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen and R is substituted with fluorine or methyl. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine and R is substituted with fluorine or methyl. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is substituted with fluorine or methyl.

[0168] In yet another embodiment, Q is naphthyl or phenyl which is substituted with a Ci-Ce alkyl group or halogen and R is selected from R-l to R-43 above.

[0169] More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine and R is selected from R-l to R-43. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is selected from R-l to R-43.

[0170] In another preferred embodiment, Q is aryl and A is CF3. Preferably, Q is naphthyl or phenyl and A is CF3. More preferably, Q is phenyl and A is CF3. In yet another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen and A is CF3. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine and A is CF3. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and A is CF3.

[0171] In another exemplary embodiment, in the compound of Formula (1) or the compound of Formula (I), Q is aryl, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole orthiadiazole and A is CF3. Preferably, Q is naphthyl or phenyl, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole and A is CF3. More preferably, Q is phenyl, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole and A is CF3.

[0172] In another embodiment, Q is aryl, R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3. Preferably, Q is naphthyl or phenyl, R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3. More preferably, Q is phenyl, R is unsubstituted or substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3.

[0173] For example, in one preferred embodiment, Q is aryl, R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3. More preferably, Q is naphthyl or phenyl, R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3. Even more preferably, Q is phenyl, R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3.

[0174] In another preferred embodiment, Q is aryl, R is selected from R-l to R-43 above, and A is CF3.

[0175] More preferably, Q is naphthyl or phenyl and R is selected from any of the above moieties. Even more preferably, Q is phenyl and R is selected from any of R-l to R-43.

[0176] In another preferred embodiment, Q is phenyl which is substituted with a Ci-Ce alkyl group or halogen, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole and A is CF3. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine, R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole and A is CF3. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) orthe compound of Formula (I), R is phenyl, pyridine, pyridazine, pyrimidine, pyrazine, furane, thiophene, oxazole, thiazole or thiadiazole and A is CF3.

[0177] In another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen, R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine, R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), R is substituted with one or more substituents selected from halogen, nitrile and C1-3 alkyl, and A is CF3.

[0178] In another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group or halogen, R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3. More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine, R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), R is substituted with fluorine or methyl, or R is substituted with fluorine, chlorine or nitrile, and A is CF3.

[0179] In yet another embodiment, Q is naphthyl or phenyl which is substituted with a Ci-Ce alkyl group or halogen R is selected from R-l to R-43 above, and A is CF3.

[0180] More preferably, Q is phenyl which is substituted with methyl, ethyl, fluorine or chlorine, R is selected from the above moieties and A is CF3. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), R is selected from R-l to R-43 above and A is CF3.

[0181] In a preferred embodiment, Q is selected from the following moieties: of R-A as shown above, more preferably of any of R-B as shown above.

[0182] In another preferred embodiment, Q is selected from the following moieties: , A is CHF2 or CF3, and R is selected from any of R-l to R-118, preferably selected from any of R-A as shown above, more preferably of any of R-B as shown above.

[0183] In another preferred embodiment, Q is phenyl which is substituted with methyl, ethyl, nitrile, chloro, bromo or iodo and R is substituted with one or more substituents selected from halogen, nitrile, nitro, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 haloalkoxy, and heterocyclyl. Even more preferably, Q is selected from the following moieties: wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is substituted with one or more substituents selected from halogen, nitrile, nitro, methyl, OMe, and pyrazolyl, preferably selected from selected from F, Cl, nitrile, nitro, methyl, OMe, and pyrazolyl, for example selected from F, Cl and nitrile.

[0184] In yet another embodiment, Q is naphthyl or phenyl which is substituted with a Ci-Ce alkyl group, nitrile, or halogen and R is selected from R-l to R-118 above.

[0185] More preferably, Q is phenyl which is substituted with methyl, ethyl, nitrile, chloro, bromo or iodo and R is selected from R-l to R-118 such as selected from R-A or from R-B. Even more preferably, Q is selected from the following moieties:

[0186] , preferably wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and R is selected from R-l to R-118 such as selected from R- A or from R-B.

[0187] In another preferred embodiment, Q is aryl and A is CHF2 or CF3. Preferably, is naphthyl or phenyl and A is CHF2 or CF3. More preferably, Q is phenyl and A is CHF2 or CF3. In yet another preferred embodiment, Q is napththyl, or phenyl which is substituted with a Ci-Ce alkyl group, nitrile, or halogen and A is CHF2 or CF3. More preferably, Q is phenyl which is substituted with F, Cl, Br, I, methyl, ethyl, or CN, and A is CHF2 or CF3. Even more preferably, Q is selected from the following moieties:

[0188] wherein indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I), and A is CHF2 or CF3.

[0189] In some embodiments, the double bond in the compound of Formula (1) or the compound of Formula (I) is in (E) configuration. In other embodiments, the double bond in the compound of Formula (1) or the compound of Formula (I) is in (Z) configuration. In preferred embodiments, the compound of Formula (1) or the compound of Formula (I) is the (E)-isomer.

[0190] The compound of the present invention may correspond to Formula (la) or Formula (lb) below:

[0191] Formula (la) Formula (lb) wherein A, Q and R are defined as in the embodiments above.

[0192] As will be apparent to those skilled in the art, the compound of Formula (la) corresponds to the (E)-isomer and the compound of Formula (lb) corresponds to the (Z)-isomer. Both isomers can possess insecticidal and / or parasitic activity. Preferably, the compound of Formula (I) is a compound of Formula (la).

[0193] In a preferred embodiment, the compound of Formula (I) corresponds to one of the following compounds:

[0194]

[0195]

[0196] In a preferred embodiment, the compound of Formula (1) corresponds to one of the following compounds:

[0197]

[0198]

[0199]

[0200] In a preferred embodiment, the compound of Formula (I) corresponds to one of the following compounds: Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-7, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-21, Ex-23, Ex-24, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33,

[0201] Ex-34, Ex-35, Ex-37, Ex-38, Ex-39, Ex-40, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45, Ex-47, Ex-48, Ex-49,

[0202] Ex-50, Ex-52, Ex-53, Ex-54, Ex-55, Ex-56, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-63, Ex-65, Ex-66,

[0203] Ex-67, Ex-68, Ex-73, Ex-74, Ex-75, Ex-78, Ex-79, Ex-82, Ex-86, Ex-88, Ex-91, Ex-92, Ex-95, Ex-97,

[0204] Ex-103, Ex-122, Ex-126, Ex-135, Ex-136, and Ex-141, preferably corresponds to one of the following compounds: Ex-1, Ex-2, Ex-4, Ex-6, Ex-7, Ex-11, Ex-12, Ex-16, Ex-21, Ex-23, Ex-24, Ex-27, Ex-28, Ex-31, Ex-33, Ex-34, Ex-40, Ex-41, Ex-42, Ex-43, Ex-45, Ex-47, Ex-48, Ex-49, Ex-50, Ex-52, Ex-53, Ex-55, Ex-56, Ex-57, Ex-58, Ex-61, Ex-63, Ex-65, Ex-66, Ex-67, and Ex-73.

[0205] In some embodiments, the compound of Formula (I) corresponds to one of the following compounds: Ex-1, Ex-2, Ex-4, Ex-7, Ex-11, Ex-12, Ex-16, Ex-21, and Ex-24, such as Ex-1, Ex-7, and Ex-21. In some embodiments, the compound of Formula (1) or the compound of Formula (I) may contain asymmetric centres and may be present as a single enantiomer, a pair of enantiomers in any proportion or, where more than one asymmetric center is present, contain diastereomers in all possible ratios. In case the compound of Formula (1) or the compound of Formula (I) contains one or more double bonds additionally to the double bond present in Formula (1) or Formula (I), the one or more double bonds may each independently exist in (E)- or (Z)-configuration. Any stereoisomers, enantiomers, geometric isomers, as well as tautomers of the compound of Formula (1) or the compound of Formula (I) are also encompassed by the present invention.

[0206] In addition, the compound of Formula (1) or the compound of Formula (I) may form agrochemically acceptable salts which are also covered by the present invention. Suitable salts include, but are not limited to, salts of acceptable inorganic acids such as hydrochloric, sulfuric, phosphoric, nitric, carbonic, boric, sulfamic, and hydrobromic acids, or salts of agronomically acceptable organic acids such as acetic, propionic, butyric, tartaric, maleic, hydroxymaleic, fumaric, malic, citric, lactic, mucic, gluconic, benzoic, succinic, oxalic, phenylacetic, methanesulfonic, toluenesulfonic, benzenesulfonic, salicylic, sulfanilic, aspartic, glutamic, edetic, stearic, palmitic, oleic, lauric, pantothenic, tannic, ascorbic and valeric acids. Suitable salts also include salts of inorganic and organic bases, e.g., counterions such as Na, Ca, K, Li, Mg, ammonium, and trimethylsulfonium. In addition, any isotopes including deuterated compounds are covered by the compound of Formula (1) or the compound of Formula (I).

[0207] In some embodiments, the compound of Formula (1) does not comprise compounds according to the following Formula (I): Formula (I) wherein A is selected from CF3 and CHF2; Q is selected from aryl and heteroaryl; and R is selected from aryl and heteroaryl; or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer, a rotamer or a deuterated compound thereof.

[0208] In some embodiments, the compound of Formula (1) does not comprise compounds selected from the following compounds:

[0209] COMPOSITIONS COMPRISING ONE OR MORE COMPOUNDS OF FORMULAE (1) AND (I)

[0210] The compounds of Formula (1) or compounds of Formula (I) according to the invention can be used as insecticides by themselves, but they can also be formulated into compositions. Therefore, in a third aspect, the present invention provides a composition comprising one or more compounds of Formula (1) or compounds of Formula (I) or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer, a rotamer or a deuterated compou nd thereof, and one or more auxiliaries and / or adjuvant, and optionally one or more further active ingredients. In a certain embodiment, the composition comprising one or more compounds of Formula (1) or compounds of Formula (I) is an agrochemical composition. Agrochemical compositions are generally intended to be applied to plants, for example to crop plants (including parts thereof such as seeds prior to harvest), preferably while in the field or in a greenhouse. In a certain embodiment, the composition comprising one or more compounds of Formula (1) or compounds of Formula (I) is a household composition. Household compositions are generally intended to be applied in inhabited areas such as buildings.

[0211] The compositions can be in various physical forms, e.g., in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates. Such compositions can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

[0212] The compositions according to the third aspect of the invention are prepared in a known manner, by mixing the compounds of Formula (1) or compounds of the Formula (I) with the one or more auxiliaries / adjuvants, and optionally one or more other active ingredients. In addition, the composition may comprise further additives that are conventional in this technical field, including but not limited to colorants, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and water.

[0213] For example, the compositions can be prepared e.g. by mixing a compound according the first or second aspect of the present invention as the active ingredient with the adjuvant(s) in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release).

[0214] Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

[0215] (a) Adjuvants and formulations

[0216] The adjuvants that are suitable for the preparation of the compositions according to the third aspect of the present invention are known in this technical field.

[0217] As liquid carriers there may be used: water, toluene, xylene, petroleum ether, liquid petroleum gas, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, an alcohol such as methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like.

[0218] Suitable solid carriers are, for example, talc, titanium dioxide, clay, pyrophyllite clay, silica, silicate, attapulgite clay, kieselguhr, limestone, calcium carbonate, gypsum, bentonite, calcium montmorillonite, ceramic, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, resin, wax and similar substances. A large number of surface-active substances can be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surface-active substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol / alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkylphosphate esters; and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).

[0219] Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

[0220] The compositions according to the third aspect of the present invention can further include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10thEdition, Southern Illinois University, 2010.

[0221] The inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Formulation types forthe composition of the invention include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), a soluble granule (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.

[0222] The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l / ha, especially from 10 to 1000 l / ha.

[0223] Preferred formulations can have the following compositions (% refers to weight % unless otherwise indicated), wherein "active ingredient" refers to the compounds of the present invention:

[0224] (1) Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 20 to 80 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

[0225] (2) Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

[0226] (3) Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 % (4) Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %

[0227] (5) Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %.

[0228] (b) Other active ingredients

[0229] The activity or properties of the compositions according to the third aspect of the present invention can be broadened considerably, and adapted to prevailing circumstances, by adding other insecticida lly, acaricidally and / or fungicida lly active ingredients. The mixtures of the compounds of formula (I) with other insecticida lly, acaricidally and / or fungicidally active ingredients may also have further surprising advantages which can also be described, in a wider sense, as synergistic activity. For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled in their different development stages or better behaviour during their production, for example during grinding or mixing, during their storage or during their use. Therefore, the composition according to the third aspect of the present invention may further contain one or more other active ingredients.

[0230] Suitable other active ingredients here are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0231] For the compositions according to the third aspect of the invention, the mixtures of a compound according to the first or second aspect with one or more other active ingredients listed below are preferred: substances consisting of petroleum oils (628); an insect control active substance selected from Abamectin, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, Acynonapyr, Afidopyropen, Afoxolaner, Alanycarb, Allethrin, Alpha-Cypermethrin, Alphamethrin, Amidoflumet, Aminocarb, Azocyclotin, Bensultap, Benzoximate, Benzpyrimoxan, Betacyfluthrin, Beta-cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin S)-cyclopentylisomer, Bioresmethrin, Bistrifluron, Broflanilide, Brofluthrinate, Bromophos-ethyl, Buprofezine, Butocarboxim, Cadusafos, Carbaryl, Carbosulfan, Cartap, CAS number: 1632218-00-8, CAS number: 1808115-49-2, CAS number: 2032403-97-5, CAS number: 2044701-44-0, CAS number: 2128706-05-6, CAS number: 2246757-58-2 (or 2249718-27-0), CAS number: 907187-07-9, Chlorantraniliprole, Chlordane, Chlorfenapyr, Chloroprallethrin, Chromafenozide, Clenpirin, Cloethocarb, Clothianidin, 2-chlorophenyl N-methylcarbamate (CPMC), Cyanofenphos, Cyantraniliprole, Cyclaniliprole, Cyclobutrifluram, Cycloprothrin, Cycloxaprid, Cycloxaprid, Cyenopyrafen, Cyetpyrafen, Cyflumetofen, Cyfluthrin, Cyhalodiamide, Cyhalothrin, Cypermethrin, Cyphenothrin, Cyproflanilide, Cyromazine, Deltamethrin, Diafenthiuron, Dialifos, Dibrom, Dicloromezotiaz, Diflovidazine, Diflubenzuron, dimpropyridaz, Dinactin, Dinocap, Dinotefuran, Dioxabenzofos, Emamectin (or Emamectin Benzoate), Empenthrin, Epsilon - momfluorothrin, Epsilon-metofluthrin, Esfenvalerate, Ethion, Ethiprole, Etofenprox, Etoxazole, Famphur, Fenazaquin, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyroxymate, Fensulfothion, Fenthion, Fentinacetate, Fenvalerate, Fipronil, Flometoquin, Flonicamid, Fluacrypyrim, Fluazaindolizine, Fluazuron, Flubendiamide, Flubenzimine, Flucitrinate, Flucycloxuron, Flucythrinate, Fluensulfone, Flufenerim, Flufenprox, Flufiprole, Fluhexafon, Flumethrin, Fluopyram, Flupentiofenox, Flupyradifurone, Flupyrimin, Fluralaner, Fluvalinate, Fluxametamide, Fosthiazate, Gamma- Cyhalothrin, Gossyplure™, Guadipyr, Halofenozide, Halofenozide, Halfenprox, Heptafluthrin, Hexythiazox, Hydramethylnon, Imicyafos, Imidacloprid, Imiprothrin, Indoxacarb, lodomethane, Iprodione, Isocycloseram, Isothioate, Ivermectin, Kappa-bifenthrin, Kappa- tefluthrin, Lambda-Cyhalothrin, Lepimectin, Lufenuron, Metaflumizone, Metaldehyde, Metam, Methomyl, Methoxyfenozide, Metofluthrin, Metolcarb, Mexacarbate, Milbemectin, Momfluorothrin, Niclosamide, Nicofluprole; Nitenpyram, Nithiazine, Omethoate, Oxamyl, Oxazosulfyl, Parathion-ethyl, Permethrin, Phenothrin, Phosphocarb, Piperonylbutoxide, Pirimicarb, Pirimiphos-ethyl, Pirimiphos-methyl, Polyhedrosis virus, Prallethrin, Profenofos, Profenofos, Profluthrin, Propargite, Propetamphos, Propoxur, Prothiophos, Protrifenbute, Pyflubumide, Pymetrozine, Pyraclofos, Pyrafluprole, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyrimidifen, Pyriminostrobin, Pyriprole, Pyriproxyfen, Resmethrin, Sarolaner, Selamectin, Silafluofen, Spinetoram, Spinosad, Spirodiclofen, Spiromesifen, Spiropidion, Spirotetramat, Sulfoxaflor, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Tefluthrin, Temephos, Tetrachlorantraniliprole, Tetradiphon, Tetramethrin, Tetramethylfluthrin, Tetranactin, Tetraniliprole, Theta-cypermethrin, Thiacloprid, Thiamethoxam, Thiocyclam, Thiodicarb, Thiofanox, Thiometon, Thiosultap, Tioxazafen, Tolfenpyrad, Toxaphene, Tralomethrin, Transfluthrin, Triazamate, Triazophos, Trichlorfon, Trichloronate, Trichlorphon, Triflumezopyrim, Tyclopyrazoflor, Zeta-Cypermethrin, Extract of seaweed and fermentation product derived from melasse, Extract of seaweed and fermentation product derived from melasse comprising urea, amino acids, potassium and molybdenum and EDTA-chelated manganese, Extract of seaweed and fermented plant products, Extract of seaweed and fermented plant products comprising phytohormones, vitamins, EDTA-chelated copper, zinc, and iron, Azadirachtin, Bacillus aizawai, Bacillus chitinosporus AQ746 (NRRL Accession No B-21 618), Bacillus firmus, Bacillus kurstaki, Bacillus mycoides AQ726 (NRRL Accession No. B-21664), Bacillus pumilus (NRRL Accession No B-30087), Bacillus pumilus AQ717 (NRRL Accession No. B-21662), Bacillus sp. AQ178 (ATCC Accession No. 53522), Bacillus sp. AQ175 (ATCC Accession No. 55608), Bacillus sp. AQ177 (ATCC Accession No. 55609), Bacillus subtilis unspecified, Bacillus subtilis AQ153 (ATCC Accession No. 55614), Bacillus subtilis AQ30002 (NRRL Accession No. B-50421), Bacillus subtilis AQ30004 (NRRL Accession No. B- 50455), Bacillus subtilis AQ713 (NRRL Accession No. B-21661), Bacillus subtilis AQ743 (NRRL Accession No. B-21665), Bacillus thuringiensis AQ52 (NRRL Accession No. B-21619), Bacillus thuringiensis BD#32 (NRRL Accession No B-21530), Bacillus thuringiensis subspec. kurstaki BMP 123, Beauveria bassiana, D-limonene, Granulovirus, Harpin, Helicoverpa armigera Nucleopolyhedrovirus, Helicoverpa zea Nucleopolyhedrovirus, Heliothis virescens Nucleopolyhedrovirus, Heliothis punctigera Nucleopolyhedrovirus, Metarhizium spp., Muscodor albus 620 (NRRL Accession No. 30547), Muscodor roseus A3-5 (NRRL Accession No. 30548), Neem tree based products, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, P-cymene, Plutella xylostella Granulosis virus, PI ute Ila xylostella Nucleopolyhedrovirus, Polyhedrosis virus, pyrethrum, QRD 420 (a terpenoid blend), QRD 452 (a terpenoid blend), QRD 460 (a terpenoid blend), Quillaja saponaria, Rhodococcus globerulus AQ719 (NRRL Accession No B-21663), Spodoptera frugiperda Nucleopolyhedrovirus, Streptomyces galbus (NRRL Accession No. 30232), Streptomyces sp. (NRRL Accession No. B-30145), Terpenoid blend, and Verticillium spp.; an algicide selected from the group of substances consisting of bethoxazin [CCN], copper dioctanoate (170), copper sulfate (172), cybutryne [CCN], dichlone (1052), dichlorophen (232), endothal (295), fentin (347), hydrated lime [CCN], nabam (566), quinoclamine (714), quinonamid (1379), simazine (730), triphenyltin acetate (347) and triphenyltin hydroxide (347); an anthelmintic selected from the group of substances consisting of abamectin (1), crufomate (1011), Cyclobutrifluram, doramectin [CCN], emamectin (291), emamectin benzoate (291), eprinomectin [CCN], ivermectin [CCN], milbemycin oxime [CCN], moxidectin [CCN], piperazine [CCN], selamectin [CCN], spinosad (737) and thiophanate (1435); an avicide selected from the group of substances consisting of chloralose (127), endrin (1122), fenthion (346), pyridin-4-amine (23) and strychnine (745); a bactericide selected from the group of substances consisting of 1 -hydroxy-lH-pyridine- 2-thione (1222), 4-(quinoxalin-2-ylamino)benzenesulfonamide (748), 8-hydroxyquinoline sulfate (446), bronopol (97), copper dioctanoate (170), copper hydroxide (169), cresol [CCN], dichlorophen (232), dipyrithione (1105), dodicin (1112), fenaminosulf (1144), formaldehyde (404), hydrargaphen [CCN], kasugamycin (483), kasugamycin hydrochloride hydrate (483), nickel bis(dimethyldithiocarbamate) (1308), nitrapyrin (580), octhilinone (590), oxolinic acid (606), oxytetracycline (611), potassium hydroxyquinoline sulfate (446), probenazole (658), streptomycin (744), streptomycin sesquisulfate (744), tecloftalam (766), and thiomersal [CCN]; a soil sterilant selected from the group of substances consisting of iodomethane (542) and methyl bromide (537); a chemosterilant selected from the group of substances consisting of apholate [CCN], bisazir [CCN], busulfan [CCN], diflubenzuron (250), dimatif [CCN], hemel [CCN], hempa [CCN], metepa [CCN], methiotepa [CCN], methyl apholate [CCN], morzid [CCN], penfluron [CCN], tepa [CCN], thiohempa [CCN], thiotepa [CCN], tretamine [CCN] and uredepa [CCN]; an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-l-yl acetate with (E)-dec-5-en-l-ol (222), (E)-tridec-4-en-l-yl acetate (829), (E)-6-methylhept- 2-en-4-ol (541), (E,Z)-tetradeca-4,10-dien-l-yl acetate (779), (Z)-dodec-7-en-l-yl acetate (285), (Z)-hexadec-ll-enal (436), (Z)-hexadec-ll-en-l-yl acetate (437), (Z)-hexadec-13-en- 11-yn-l-yl acetate (438), (Z)-icos-13-en-10-one (448), (Z)-tetradec-7-en-l-al (782), (Z)-tetradec-9-en-l-ol (783), (Z)-tetradec-9-en-l-yl acetate (784), (7E,9Z)-dodeca-7,9-dien-l- yl acetate (283), (9Z,11 E)-tetradeca-9,ll-dien-l-yl acetate (780), (9Z,12E)-tetradeca-9,12- dien-l-yl acetate (781), 14-methyloctadec-l-ene (545), 4-methylnonan-5-ol with 4-methylnonan-5-one (544), alpha-multistriatin [CCN], brevicomin [CCN], codlelure [CCN], codlemone (167), cuelure (179), disparlure (277), dodec-8-en-l-yl acetate (286), dodec-9-en-

[0232] 1-yl acetate (287), dodeca-8, 10-dien-l-yl acetate (284), dominicalure [CCN], ethyl 4-methyloctanoate (317), eugenol [CCN], frontalin [CCN], gossyplure (420), grandlure (421), grandlure I (421), grandlure II (421), grandlure III (421), grandlure IV (421), hexalure [CCN], ipsdienol [CCN], ipsenol [CCN], japonilure (481), lineatin [CCN], litlure [CCN], looplure [CCN], medlure [CCN], megatomoic acid [CCN], methyl eugenol (540), muscalure (563), octadeca- 2,13-dien-l-yl acetate (588), octadeca-3,13-dien-l-yl acetate (589), orfralure [CCN], oryctalure (317), ostramone [CCN], siglure [CCN], sordidin (736), sulcatol [CCN], tetradic-ll-en-l-yl acetate (785), trimedlure (839), trimedlure A (839), trimedlure Bl (839), trimedlure B2 (839), trimedlure C (839) and trunc-call [CCN]; an insect repellent selected from the group of substances consisting of

[0233] 2-(octylthio)ethanol (591), butopyronoxyl (933), butoxy(polypropylene glycol) (936), dibutyl adipate (1046), dibutyl phthalate (1047), dibutyl succinate (1048), diethyltoluamide [CCN], dimethyl carbate [CCN], dimethyl phthalate [CCN], ethyl hexanediol (1137), hexamide [CCN], methoquin-butyl (1276), methylneodecanamide [CCN], oxamate [CCN] and picaridin [CCN]; a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (913), bromoacetamide [CCN], calcium arsenate [CCN], cloethocarb (999), copper acetoarsenite [CCN], copper sulfate (172), fentin (347), ferric phosphate (352), metaldehyde (518), methiocarb (530), niclosamide (576), niclosamide-olamine (576), pentachlorophenol (623), sodium pentachlorophenoxide (623), tazimcarb (1412), thiodicarb (799), tributyltin oxide (913), trifenmorph (1454), trimethacarb (840), triphenyltin acetate (347) and triphenyltin hydroxide (347), pyriprole [394730-71-3]; a nematicide selected from the group of substances consisting of AKD-3088 (compound code), l,2-dibromo-3-chloropropane (lUPAC / Chemical Abstracts name) (1045),

[0234] 1.2-dichloropropane (IUPAC / Chemical Abstracts name) (1062), 1,2-dichloropropane with

[0235] 1.3-dichloropropene (1063), 1,3-dichloropropene (233), 3,4-dichlorotetrahydrothiophene 1,1-dioxide (lUPAC / Chemical Abstracts name) (1065), 3-(4-chlorophenyl)-5- methylrhodanine (980), 5-methyl-6-thioxo-l,3,5-thiadiazinan-3-ylacetic acid (1286), 6- isopentenylaminopurine (210), abamectin (1), acetoprole [CCN], alanycarb (15), aldicarb (16), aldoxycarb (863), AZ 60541 (compound code), benclothiaz [CCN], benomyl (62), butylpyridaben , cadusafos (109), carbofuran (118), carbon disulfide (945), carbosulfan (119), chloropicrin (141), chlorpyrifos (145), cloethocarb (999), Cyclobutrifluram, cytokinins (210), dazomet (216), DBCP (1045), DCIP (218), diamidafos (1044), dichlofenthion (1051), dicliphos, dimethoate (262), doramectin [CCN], emamectin (291), emamectin benzoate (291), eprinomectin [CCN], ethoprophos (312), ethylene dibromide (316), fenamiphos (326), fen pyrad, fensulfothion (1158), fosthiazate (408), fosthietan (1196), furfural [CCN], GY-81 (development code) (423), heterophos [CCN], iodomethane (542), isamidofos (1230), isazofos (1231), ivermectin [CCN], kinetin (210), mecarphon (1258), metam (519), metam- potassium (519), metam-sodium (519), methyl bromide (537), methyl isothiocyanate (543), milbemycin oxime [CCN], moxidectin [CCN], Myrothecium verrucaria composition (565), NC-184, oxamyl (602), phorate (636), phosphamidon (639), phosphocarb [CCN], sebufos , selamectin [CCN], spinosad (737), terbam , terbufos (773), tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422), thiafenox , thionazin (1434), triazophos (820), triazuron , xylenols [CCN], YI-5302 (compound code) and zeatin (210), fluensulfone [318290-98-1], fluopyram; a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580); a plant activator selected from the group of substances consisting of acibenzolar (6), acibenzolar-S-methyl (6), probenazole (658) and Reynoutria sachalinensis extract (720); a rodenticide selected from the group of substances consisting of 2-isovalerylindan-l, 3-dione (1246), 4-(quinoxalin-2-ylamino)benzenesulfonamide (748), alpha-chlorohydrin [CCN], aluminium phosphide (640), antu (880), arsenous oxide (882), barium carbonate (891), bisthiosemi (912), brodifacoum (89), bromadiolone (including alpha-bromadiolone), bromethalin (92), calcium cyanide (444), chloralose (127), chlorophacinone (140), cholecalciferol (850), coumachlor (1004), coumafuryl (1005), coumatetralyl (175), crimidine (1009), difenacoum (246), difethialone (249), diphacinone (273), ergocalciferol (301), flocoumafen (357), fluoroacetamide (379), flupropadine (1183), flupropadine hydrochloride (1183), gamma-HCH (430), HCH (430), hydrogen cyanide (444), iodomethane (542), lindane (430), magnesium phosphide (640), methyl bromide (537), norbormide (1318), phosacetim (1336), phosphine (640), phosphorus [CCN], pindone (1341), potassium arsenite [CCN], pyrinuron (1371), scilliroside (1390), sodium arsenite [CCN], sodium cyanide (444), sodium fluoroacetate (735), strychnine (745), thallium sulfate [CCN], warfarin (851) and zinc phosphide (640); a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (934), 5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2- enone (903), farnesol with nerolidol (324), MB-599 (development code) (498), MGK 264 (development code) (296), piperonyl butoxide (649), piprotal (1343), propyl isomer (1358), S421 (development code) (724), sesamex (1393), sesasmolin (1394) and sulfoxide (1406); an animal repellent selected from the group of substances consisting of anthraquinone (32), chloralose (127), copper naphthenate [CCN], copper oxychloride (171), diazinon (227), dicyclopentadiene (chemical name) (1069), guazatine (422), guazatine acetates (422), methiocarb (530), pyridin-4-amine (23), thiram (804), trimethacarb (840), zinc naphthenate [CCN] and ziram (856); a virucide selected from the group of substances consisting of imanin [CCN] and ribavirin [CCN]; a wound protectant selected from the group of substances consisting of mercuric oxide (512), octhilinone (590) and thiophanate-methyl (802); a biologically active substance selected from l,l-bis(4-chloro-phenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-l-naphthylacetamide, 4-chlorophenyl phenyl sulfone, acetoprole, aldoxycarb, amidithion, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenous oxide, azobenzene, azothoate, benomyl, benoxa-fos, benzyl benzoate, bixafen, brofenvalerate, bromo-cyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphechlor, carbanolate, carbophenothion, cymiazole, chino-methionat, chlorbenside, chlordimeform, chlordimeform hydrochloride, chlorfenethol, chlorfenson, chlorfensulfide, chlorobenzilate, chloromebuform, chloromethiuron, chloropropylate, chlorthiophos, cinerin I, cinerin II, cinerins, closantel, coumaphos, crotamiton, crotoxyphos, cufraneb, cyanthoate, DCPM, DDT, demephion, demephion-O, demephion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulfon, dichlofluanid, dichlorvos, dicliphos, dienochlor, dimefox, dinex, dinex-diclexine, dinocap-4, dinocap-6, dinocton, dinopenton, dinosulfon, dinoterbon, dioxathion, diphenyl sulfone, disulfiram, DNOC, dofenapyn, doramectin, endothion, eprinomectin, ethoate-methyl, etrimfos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fen-pyroximate, fenpyrazamine, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenetil, fluorbenside, FMC 1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, glyodin, halfenprox, hexadecyl cyclopropanecarboxylate, isocarbophos, jasmolin I, jasmolin II, jodfenphos, lindane, malonoben, mecarbam, mephosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifluridide, nikkomycins, nitrilacarb, nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprofos, oxydisulfoton, pp'-DDT, parathion, permethrin, phenkapton, phosalone, phosfolan, phosphamidon, polychloroterpenes, polynactins, proclonol, promacyl, propoxur, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quintiofos, R-1492, phosglycin, rotenone, schradan, sebufos, selamectin, sophamide, SSI-121, sulfiram, sulfluramid, sulfotep, sulfur, diflovidazin, tau-fluvalinate, TEPP, terbam, tetradifon, tetrasul, thiafenox, thiocarboxime, thiofanox, thiometon, thioquinox, thuringiensin, triamiphos, triarathene, triazophos, triazuron, trifenofos, trinactin, vamidothion, vaniliprole, bethoxazin, copper dioctanoate, copper sulfate, cybutryne, dichlone, dichlorophen, endothal, fentin, hydrated lime, nabam, quinoclamine, quinonamid, simazine, triphenyltin acetate, triphenyltin hydroxide, crufomate, piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1 -hydroxy-lH-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodicin, fenaminosulf, formaldehyde, hydrargaphen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline, potassium hydroxyquinoline sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis , Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en-l-yl acetate with (E)-dec-5-en-l-ol, (E)-tridec-4-en-l-yl acetate, (E)-6-methylhept-2-en-4-ol, (E,Z)-tetradeca-4,10-dien-l-yl acetate, (Z)-dodec-7-en-l-yl acetate, (Z)-hexadec-ll-enal, (Z)-hexadec-ll-en-l-yl acetate, (Z)-hexadec-13-en-ll -yn-l-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en-l-al, (Z)-tetradec-9-en-l-ol, (Z)-tetradec-9-en-l-yl acetate, (7E,9Z)-dodeca-7,9-dien-l-yl acetate, (9Z,llE)-tetradeca- 9,11-dien-l-yl acetate, (9Z,12E)-tetradeca-9,12-dien-l-yl acetate, 14-methyloctadec-l-ene, 4-methylnonan-5-ol with 4-methylnonan-5-one, alpha-multistriatin, brevicomin, codlelure, codlemone, cuelure, disparlure, dodec-8-en-l-yl acetate, dodec-9-en-l-yl acetate, dodeca-8, 10-dien-l-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, frontalin, grandlure, grandlure I, grandlure II, grandlure III, grandlure IV, hexalure, ipsdienol, ipsenol, japonilure, lineatin, litlure, looplure, medlure, megatomoic acid, methyl eugenol, muscalure, octadeca- 2,13-dien-l-yl acetate, octadeca-3,13-dien-l-yl acetate, orfralure, oryctalure, ostramone, siglure, sordidin, sulcatol, tetradec-11 -en-l-yl acetate, trimedlure, trimedlure A, trimedlure Bl, trimedlure B2, trimedlure C, trunc-call, 2-(octylthio)-ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethyl carbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methylneodecanamide, oxamate, picaridin, 1-dichloro-l-nitroethane,

[0236] 1.1-dichloro-2,2-bis(4-ethylphenyl)-ethane, 1,2-dichloropropane with 1,3-dichloropropene,

[0237] 1-bromo-2-chloroethane, 2,2,2-trichloro-l-(3,4-dichloro-phenyl)ethyl acetate,

[0238] 2.2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(l,3-dithiolan-2-yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-l,3-dioxolan-

[0239] 2-yl)phenyl methylcarbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerylindan-l, 3-dione, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-l-chloroprop-l-ene, 3-methyl-l- phenylpyrazol-5-yl dimethyl-carbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-l-enyl dimethylcarbamate, acethion, acrylonitrile, aldrin, allosamidin, allyxycarb, alpha-ecdysone, aluminium phosphide, aminocarb, anabasine, athidathion, azamethiphos, Bacillus thuringiensis delta endotoxins, barium hexafluorosilicate, barium polysulfide, barthrin, Bayer 22 / 190, Bayer 22408, beta- cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl) ether, borax, bromfenvinfos, bromo-DDT, bufencarb, butacarb, butathiofos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, cevadine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocythrin, copper acetoarsenite, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidafos, dicapthon, dichlofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilor, dimefluthrin, dimetan, dimethrin, dimethylvinphos, dimetilan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzofos, dithicrofos, DSP, ecdysterone, El 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenethacarb, fenitrothion, fenoxacrim, fenpirithrin, fensulfothion, fenthion- ethyl, flucofuron, fosmethilan, fospirate, fosthietan, furathiocarb, furethrin, guazatine, guazatine acetates, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hyquincarb, IPSP, isazofos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan, kinoprene, lead arsenate, leptophos, lirimfos, lythidathion, m- cumenyl methylcarbamate, magnesium phosphide, mazidox, mecarphon, menazon, mercurous chloride, mesulfenfos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methocrotophos, methoprene, methothrin, methoxychlor, methyl isothiocyanate, methylchloroform, methylene chloride, metoxadiazone, mirex, naftalofos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4- iodophenyl O-ethyl ethylphosphonothioate, 0,0-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, 0,0-diethyl 0-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion- methyl, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, phenkapton, phosnichlor, phosphine, phoxim-methyl, pirimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, kadethrin, ryania, ryanodine, sabadilla), schradan, sebufos, SI-0009, thiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oils, tazimcarb, TDE, tebupirimfos, temephos, terallethrin, tetrachloroethane, thicrofos, thiocyclam, thiocyclam hydrogen oxalate, thionazin, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetaphos-3, trichloronat, trimethacarb, tolprocarb, triclopyricarb, triprene, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, and meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, trifenmorph, l,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothio-phene 1,1 dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-l,3,5-thiadiazinan- 3-ylacetic acid, 6-isopentenylaminopurine, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, benclothiaz, cytokinins, DCIP, furfural, isamidofos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis extract, alpha-chlorohydrin, antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropadine, flupropadine hydrochloride, norbormide, phosacetim, phosphorus, pindone, pyrinuron, scilliroside, - sodium fluoroacetate, thallium sulfate, warfarin, -2-(2-butoxyethoxy)ethyl piperonylate, 5-(l,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, verbutin, MGK 264, piperonyl butoxide, piprotal, propyl isomer, S421, sesamex, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chloroinconazide, mercuric oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil-, imiben-conazole, ipconazole, metconazole, myclobutanil, paclobutrazole, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, -simeconazole, tebucon-azole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, - metalaxyl, Rmetalaxyl, ofurace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, dichlozoline, myclozoline-, procymidone, vinclozoline, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, bordeaux mixture, copper oxide, mancopper, oxine-copper, nitrothal-isopropyl, edifenphos, iprobenphos, phosdiphen, tolclofos-methyl, anilazine, benthiavalicarb, blasticidin-S, chloroneb, chloro-tha-lonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomezine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, fluopicolide, flusulfamide, fluxapyroxad, -fenhexamid, fosetyl-aluminium, hymexazol, iprovalicarb, cyazofamid, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxins, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriofenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, 3-difluoromethyl-l- methyl-lH-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucypram, isotianil, dipymetitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][l,4]dithiino[l,2-c]isothiazole-3- carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-l,l-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-l- methyl-N-[l,l,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)- N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4- (2- bromo- 4- fluorophenyl)- N-(2-chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5- amine, fluindapyr, coumethoxystrobin (jiaxiangjunzhi), Ivbenmixianan, dichlobentiazox, mandestrobin, 3-(4,4- difluoro-3,4-dihydro-3,3-dimethylisoquinolin-l-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2- methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiprolin, tert-butyl N- [6-[[[(l-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumid, inpyrfluxam, trolprocarb, mefentrifluconazole, ipfentrifluconazole, 2- (difluoromethyl)-N-[(3R)-3-ethyl-l,l-dimethyl-indan-4-yl]pyrid ine-3-carboxamide, N'-(2,5- dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2- yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[l-[2-[3,5- bis(difluoromethyl)pyrazol-l-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3- chloro-phenyl] methanesulfonate, but-3-ynyl N-[6-[[(Z)-[(l-methyltetrazol-5-yl)-phenyl- methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4- dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5- phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridachlometyl, 3-(difluoromethyl)-l-methyl-N- [1,1,3- trimethylindan-4-yl]pyrazole-4-carboxamide, 1 -[2-[[l-(4-chlorophenyl)pyrazol-3- yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, l-methyl-4-[3-methyl-2-[[2- methyl-4-(3,4,5-trimethylpyrazol-l-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctradin, amisulbrom, penflufen, (Z,2E)-5-[l-(4-chlorophenyl)pyrazol-3-yl]oxy-2- methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamid, fenpicoxamid, tebufloquin, ipflufenoquin, quinofumelin, isofetamid, N-[2-[2,4-dichloro-phenoxy]phenyl]-3- (difluoromethyl)-l-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-

[0240] (trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-l-methyl-pyrazole-4-carboxamide, benzothiostrobin, phenamacril, 5-amino-l,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flutianil, fluopimomide, pyrapropoyne, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-l,l- dimethyl-indan-4-yl)pyridine-3-carboxamide, 2- (difluoromethyl) -N- ((3R) - 1 , 1 , 3- trimethylindan- 4- yl) pyridine- 3- carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-l,l-difluoro-2- hydroxy-3-(l,2,4-triazol-l-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetraprole, 2- (difluoromethyl) - N- ((3R) - 1 , 1 , 3- trimethylindan- 4- yl) pyridine-3-carboxamide, a-(l,l- dimethylethyl)-a-[4'- (trifluoromethoxy) [1 , 1'- biphenyl] - 4- yl] -5- pyrimidinemethanol, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-l,l-difluoro-2-hydroxy-3-(l,2,4- triazol-l-yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-l,l-difluoro-2- hydroxy-3-(5-sulfanyl-l,2,4-triazol-l-yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2-(2,4- difluorophenyl)-l,l-difluoro-2-hydroxy-3-(5-thioxo-4H-l,2,4-triazol-l-yl)propyl]-3- pyridyl]oxy]benzonitrile, trinexapac, coumoxystrobin, zhongshengmycin, thiodiazole copper, zinc thiazole, amectotractin, iprodione, N-octyl-N'-[2-(octylamino)ethyl]ethane-l,2-diamine; N'-[5-bromo-2-methyl-6-[(lS)-l-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl- formamidine, N'-[5-bromo-2-methyl-6-[(l R)-l-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl- N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(l-methyl-2-propoxy-ethoxy)-3-pyridyl]-N- ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(l-methyl-2-propoxy-ethoxy)-3- pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(l-methyl-2-propoxy- ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds may be prepared from the methods described in WO2015 / 155075); N'-[5-bromo-2-methyl-6-(2- propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound may be prepared from the methods described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2- methyl-4-( 2,2,2-trifluoro-l-hydroxy-l-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(l -cyclopropyl-2,2,2-trifluoro-l-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N- methyl-formamidine (these compounds may be prepared from the methods described in WO2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2- yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2- trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds may be prepared from the methods described in W02019 / 110427); N-[(l R)-l-benzyl-3-chloro-l- methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(l S)-l-benzyl-3-chloro-l-methyl- but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(l R)-l-benzyl-3,3,3-trifluoro-l-methyl- propyl]-8-fluoro-quinoline-3-carboxamide, N-[(l S)-l-benzyl-3,3,3-trifluoro-l-methyl- propyl]-8-fluoro-quinoline-3-carboxamide, N-[(lR)-l-benzyl-l,3-dimethyl-butyl]-7,8- difluoro-quinoline-3-carboxamide, N-[(l S)-l-benzyl-l,3-dimethyl-butyl]-7,8-difluoro- quinoline-3-carboxamide, 8-fluoro-N-[(l R)-l-[(3-fluorophenyl)methyl]-l,3-dimethyl- butyl]quinoline-3-carboxamide, 8-fluoro-N-[(l S)-l-[(3-fluorophenyl)methyl]-l,3-dimethyl- butyl]quinoline-3-carboxamide, N-[(l R)-l-benzyl-l,3-dimethyl-butyl]-8-fluoro-quinoline-3- carboxamide, N-[(lS)-l-benzyl-l,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((l R)-l-benzyl-3-chloro-l-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((l S)-l- benzyl-3-chloro-l-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds may be prepared from the methods described in WO2017 / 153380); l-(6,7- dimethylpyrazolo[l,5-a]pyridin-3-yl)-4, 4, 5-trifluoro-3, 3-dimethyl-isoquinoline, l-(6,7- dimethylpyrazolo[l,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro- 3,3-dimethyl-l-(6-methylpyrazolo[l,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl- l-(7-methylpyrazolo[l,5-a]pyridin-3-yl)isoquinoline, l-(6-chloro-7-methyl-pyrazolo[l,5- a]pyridin-3-yl)-4,4-difluoro-3, 3-dimethyl-isoquinoline (these compounds may be prepared from the methods described in W02017 / 025510); 1 -(4, 5-dimethylbenzimidazol-l-yl)-4, 4, 5- trifluoro-3, 3-dimethyl-isoquinoline, l-(4,5-dimethylbenzimidazol-l-yl)-4,4-difluoro-3, 3- dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-l-(4-methylbenzimidazol-l- yl)isoquinoline, 4, 4-difluoro-l-(5-fluoro-4-methyl-benzimidazol-l-yl)-3, 3-dimethyl- isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-l-isoquinolyl)-7,8-dihydro-6H- cyclopenta[e]benzimidazole (these compounds may be prepared from the methods described in WO2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-

[0241] 1.2.4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-

[0242] (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, l-methoxy-3-methyl-l- [[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, l,3-dimethoxy-l-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-l-methoxy-l-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-

[0243] 1.2.4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl l-[[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-l-[[4-[5-

[0244] (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]-l,2,4-triazol-3-amine. The compounds in this paragraph may be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2- (trifluoromethyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2- (trifluoromethyl)-3-pyridyl]-l-(l,2,4-triazol-l-yl)propan-2-ol (this compound may be prepared from the methods described in WO 2017 / 029179); 3-[2-(l-chlorocyclopropyl)-3-(2- fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016 / 156290); 3-[2-(l-chlorocyclopropyl)-3-(3-chloro-2- fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound may be prepared from the methods described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6- methyl-pyridine-3-carboxylate (this compound may be prepared from the methods described in WO 2014 / 006945); 2,6-Dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole-l,3,5,7(2H,6H)- tetrone (this compound may be prepared from the methods described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[l-(2,4-dichlorophenyl)pyrazol- 3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound may be prepared from the methods described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)- N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl- N-methyl-formamidine (this compound may be prepared from the methods described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-l,l-dimethyl-indan-4-yl]pyridine-3- carboxamide (this compound may be prepared from the methods described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methanone (these compounds may be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]acetamide (this compound may be prepared from the methods described in WO 2018 / 065414); ethyl l-[[5-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]-2- thienyl]methyl]pyrazole-4-carboxylate (this compound may be prepared from the methods described in WO 2018 / 158365) ; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide (these compounds may be prepared from the methods described in WO 2018 / 202428); microbials including: Acinetobacter Iwoffii, Acremonium alternatum, Acremonium cephalosporium, Acremonium diospyri, Acremonium obclavatum, Adoxophyes orana granulovirus (AdoxGV) (Capex®), Agrobacterium radiobacter strain K84 (Galltrol-A®), Alternaria alternate, Alternaria cassia, Alternaria destruens (Smolder®), Ampelomyces quisqualis (AQ10®), Aspergillus flavus AF36 (AF36®), Aspergillus flavus NRRL 21882 (Aflaguard®), Aspergillus spp., Aureobasidium pullulans, Azospirillum, (MicroAZ®, TAZO B®), Azotobacter, Azotobacter chroocuccum (Azotomeal®), Azotobacter cysts (Bionatural Blooming Blossoms®), Bacillus amyloliquefaciens, Bacillus cereus, Bacillus chitinosporus strain CM-1, Bacillus chitinosporus strain AQ746, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®), Bacillus licheniformis strain 3086 (EcoGuard®, Green Releaf®), Bacillus circulans, Bacillus firmus (BioSafe®, BioNem-WP®, VOTiVO®), Bacillus firmus strain 1-1582, Bacillus macerans, Bacillus marismortui, Bacillus megaterium, Bacillus mycoides strain AQ726, Bacillus papillae (Milky Spore Powder®), Bacillus pumilus spp., Bacillus pumilus strain GB34 (Yield Shield®), Bacillus pumilus strain AQ717, Bacillus pumilus strain QST 2808 (Sonata®, Ballad Plus®), Bacillus spahericus (VectoLex®), Bacillus spp., Bacillus spp. strain AQ175, Bacillus spp. strain AQ177, Bacillus spp. strain AQ178, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®), Bacillus subtilis strain QST 714 (JAZZ®), Bacillus subtilis strain AQ153, Bacillus subtilis strain AQ743, Bacillus subtilis strain QST3002, Bacillus subtilis strain QST3004, Bacillus subtilis var. amyloliquefaciens strain FZB24 (Taegro®, Rhizopro®), Bacillus thuringiensis Cry 2Ae, Bacillus thuringiensis CrylAb, Bacillus thuringiensis aizawai GC 91 (Agree®), Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®), Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP ®, Astuto®, Dipel WP®, Biobit®, Foray®), Bacillus thuringiensis kurstaki BMP 123 (Baritone®), Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®), Bacillus thuringiensis strain BD#32, Bacillus thuringiensis strain AQ52, Bacillus thuringiensis var. aizawai (XenTari®, DiPei®), bacteria spp. (GROWMEND®, GROWSWEET®, Shootup®), bacteriophage of Clavipacter michiganensis (AgriPhage®), Bakflor®, Beauveria bassiana (Beaugenic®, Brocaril WP®), Beauveria bassiana GHA (Mycotrol ES®, Mycotrol O®, BotaniGuard®), Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, Melocont®), Beauveria spp., Botrytis cineria, Bradyrhizobium japonicum (TerraMax®), Brevibacillus brevis, Bacillus thuringiensis tenebrionis (Novodor®), BtBooster, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®), Burkholderia gladii, Burkholderia gladioli, Burkholderia spp., Canadian thistle fungus (CBH Canadian Bioherbicide®), Candida butyri, Candida famata, Candida fructus, Candida glabrata, Candida guilliermondii, Candida melibiosica, Candida oleophila strain O, Candida pa rapsilosis, Candida pelliculosa, Candida pulcherrima, Candida reukaufii, Candida saitoana (Bio-Coat®, Biocure®), Candida sake, Candida spp., Candida tenius, Cedecea dravisae, Cellulomonas flavigena, Chaetomium cochliodes (Nova-Cide®), Chaetomium globosum (Nova-Cide®), Chromobacterium subtsugae strain PRAA4-1T (Grandevo®), Cladosporium cladosporioides, Cladosporium oxysporum, Cladosporium chlorocephalum, Cladosporium spp., Cladosporium tenuissimum, Clonostachys rosea (EndoFine®), Colletotrichum acutatum, Coniothyrium minitans (Cotans WG®), Coniothyrium spp., Cryptococcus albidus (YIELDPLUS®), Cryptococcus humicola, Cryptococcus infirmo-miniatus, Cryptococcus laurentii, Cryptophlebia leucotreta granulovirus (Cryptex®), Cupriavidus campinensis, Cydia pomonella granulovirus (CYD-X®), Cydia pomonella granulovirus (Madex®, Madex Plus®, Madex Max / Carpovirusine®), Cylindrobasidium laeve (Stumpout®), Cylindrocladium, Debaryomyces hansenii, Drechslera hawaiinensis, Enterobacter cloacae, Enterobacteriaceae, Entomophtora virulenta (Vektor®), Epicoccum nigrum, Epicoccum purpurascens, Epicoccum spp., Filobasidium floriforme, Fusarium acuminatum, Fusarium chlamydosporum, Fusarium oxysporum (Fusaclean® / Biofox C®), Fusarium proliferatum, Fusarium spp., Galactomyces geotrichum, Gliocladium catenulatum (Primastop®, Prestop®), Gliocladium roseum, Gliocladium spp. (SoilGard®), Gliocladium virens (Soilgard®), Granulovirus (Granupom®), Halobacillus halophilus, Halobacillus litoralis, Halobacillus trueperi, Halomonas spp., Halomonas subglaciescola, Halovibrio variabilis, Hanseniaspora uvarum, Helicoverpa armigera nucleopolyhedrovirus (Helicovex®), Helicoverpa zea nuclear polyhedrosis virus (Gemstar®), Isoflavone - formononetin (Myconate®), Kloeckera apiculata, Kloeckera spp., Lagenidium giganteum (Laginex®), Lecanicillium longisporum (Vertiblast®), Lecanicillium muscarium (Vertikil®), Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®), Marinococcus halophil us, Meira geulakonigii, Metarhizium anisopliae (Met52®), Metarhizium anisopliae (Destruxin WP®), Metschnikowia fruticola (Shemer®), Metschnikowia pulcherrima, Microdochium dimerum (Antibot®), Micromonospora coerulea, Microsphaeropsis ochracea, Muscodor albus 620 (Muscudor®), Muscodor roseus strain A3-5, Mycorrhizae spp. (AMykor®, Root Maximizer®), Myrothecium verrucaria strain AARC-0255 (DiTera®), BROS PLUS®, Ophiostoma piliferum strain D97 (Sylvanex®), Paecilomyces farinosus, Paecilomyces fumosoroseus (PFR-97®, PreFeRal®), Paecilomyces linacinus (Biostat WP®), Paecilomyces lilacinus strain 251 (MeloCon WG®), Paenibacillus polymyxa, Pantoea agglomerans (BlightBan C9-1®), Pantoea spp., Pasteuria spp. (Econem®), Pasteuria nishizawae, Penicillium aurantiogriseum, Penicillium billai (Jumpstart®, TagTeam®), Penicillium brevicompactum, Penicillium frequentans, Penicillium griseofulvum, Penicillium purpurogenum, Penicillium spp., Penicillium viridicatum, Phlebiopsis gigantean (Rotstop®), phosphate solubilizing bacte ria (Phosphomeal®), Phytophthora cryptogea, Phytophthora palmivora (Devine®), Pichia anomala, Pichia guilermondii, Pichia membranaefaciens, Pichia onychis, Pichia stipites, Pseudomonas aeruginosa, Pseudomonas aureofasciens (Spot-Less Biofungicide®), Pseudomonas cepacia, Pseudomonas chlororaphis (AtEze®), Pseudomonas corrugate, Pseudomonas fluorescens strain A506 (BlightBan A506®), Pseudomonas putida, Pseudomonas reactans, Pseudomonas spp., Pseudomonas syringae (Bio-Save®), Pseudomonas viridiflava, Pseudomons fluorescens (Zequanox®), Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®), Puccinia canaliculata, Puccinia thlaspeos (Wood Warrior®), Pythium paroecandrum, Pythium oligandrum (Polygandron®, Polyversum®), Pythium periplocum, Rhanella aquatilis, Rhanella spp., Rhizobia (Dormal®, Vault®), Rhizoctonia, Rhodococcus globerulus strain AQ719, Rhodosporidium diobovatum, Rhodosporidium toruloides, Rhodotorula spp., Rhodotorula glutinis, Rhodotorula graminis, Rhodotorula mucilagnosa, Rhodotorula rubra, Saccharomyces cerevisiae, Salinococcus roseus, Sclerotinia minor, Sclerotinia minor (SARRITOR®), Scytalidium spp., Scytalidium uredinicola, Spodoptera exigua nuclear polyhedrosis virus (Spod-X®, Spexit®), Serratia marcescens, Serratia plymuthica, Serratia spp., Sordaria fimicola, Spodoptera littoralis nucleopolyhedrovirus (Littovir®), Sporobolomyces roseus, Stenotrophomonas maltophilia, Streptomyces ahygroscopicus, Streptomyces albaduncus, Streptomyces exfoliates, Streptomyces galbus, Streptomyces griseoplanus, Streptomyces griseoviridis (Mycostop®), Streptomyces lydicus (Actinovate®), Streptomyces lydicus WYEC-108 (ActinoGrow®), Streptomyces violaceus, Tilletiopsis minor, Tilletiopsis spp., Trichoderma asperellum (T34 Biocontrol®), Trichoderma gamsii (Tenet®), Trichoderma atroviride (Plantmate®), Trichoderma hamatum TH 382, Trichoderma harzianum rifai (Mycostar®), Trichoderma harzianum T-22 (Trianum-P®, Plantshield HC®, Rootshield®, Trianum-G®), Trichoderma harzianum T-39 (Trichodex®), Trichoderma inhamatum, Trichoderma koningii, Trichoderma spp. LC 52 (Sentinel®), Trichoderma lignorum, Trichoderma longibrachiatum, Trichoderma polysporum (Binab T®), Trichoderma taxi, Trichoderma virens, Trichoderma virens (formerly Gliocladium virens GL- 21) (SoilGuard®), Trichoderma viride, Trichoderma viride strain ICC 080 (Remedier®), Trichosporon pullulans, Trichosporon spp., Trichothecium spp., Trichothecium roseum, Typhula phacorrhiza strain 94670, Typhula phacorrhiza strain 94671, Ulocladium atrum, Ulocladium oudemansii (Botry-Zen®), Ustilago maydis, various bacteria and supplementary micronutrients (Natural II®), various fungi (Millennium Microbes®), Verticillium chlamydosporium, Verticillium lecanii (Mycotal®, Vertalec®), Vip3Aa20 (VIPtera®), Virgibaclillus marismortui, Xanthomonas campestris pv. Poae (Camperico®), Xenorhabdus bovienii, Xenorhabdus nematophilus;

[0245] Plant extracts including: pine oil (Retenol®), azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, Botanical IGR (Neemazad®, Neemix®), canola oil (Lilly Miller Vegol®), Chenopodium ambrosioides near ambrosioides (Requiem®), Chrysanthemum extract (Crisant®), extract of neem oil (Trilogy®), essentials oils of Labiatae (Botania®), extracts of clove rosemary peppermint and thyme oil (Garden insect killer®), Glycinebetaine (Greenstim®), garlic, lemongrass oil (GreenMatch®), neem oil, Nepeta cataria (Catnip oil), Nepeta catarina, nicotine, oregano oil (MossBuster®), Pedaliaceae oil (Nematon®), pyrethrum, Quillaja saponaria (NemaQ®), Reynoutria sachalinensis (Regalia®, Sakalia®), rotenone (Eco Roten®), Rutaceae plant extract (Soleo®), soybean oil (Ortho ecosense®), tea tree oil (Timorex Gold®), thymus oil, AGNIQUE® MMF, BugOil®, mixture of rosemary sesame pepermint thyme and cinnamon extracts (EF 300®), mixture of clove rosemary and peppermint extract (EF 400®), mixture of clove pepermint garlic oil and mint (Soil Shot®), kaolin (Screen®), storage glucam of brown algae (Laminarin®); pheromones including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®), Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®), Grape Berry Moth Pheromone (3M MEC-GBM Sprayable Pheromone®), Leafroller pheromone (3M MEC - LR Sprayable Pheromone®), Muscamone (Snip? Fly Bait®, Starbar Premium Fly Bait®), Oriental Fruit Moth Pheromone (3M oriental fruit moth sprayable pheromone®), Peachtree Borer Pheromone (Isomate-P®), Tomato Pinworm Pheromone (3M Sprayable pheromone®), Entostat powder (extract from palm tree) (Exosex CM®), (E,Z,Z)-3,8,11 Tetradecatrienyl acetate, (Z,Z,E)-7,11,13-Hexadecatrienal, (E,Z)-7,9-Dodecadien-l-yl acetate, 2-Methyl-l-butanol, Calcium acetate, Scenturion®, Biolure®, Check-Mate®, Lavandulyl senecioate; Macrobials including: Aphelinus abdominalis, Aphidius ervi (Aphelinus-System®), Acerophagus papaya, Adalia bipunctata (Adalia-System®), Adalia bipunctata (Adaline®), Adalia bipunctata (Aphida lia® ), Ageniaspis citricola, Ageniaspis fuscicollis, Amblyseius andersoni (Anderline®, Andersoni-System®), Amblyseius californicus (Amblyline®, Spical®), Amblyseius cucumeris (Thripex®, Bugline cucumeris®), Amblyseius fallacis (Fallacis®), Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®), Amblyseius womersleyi (WomerMite®), Amitus hesperidum, Anagrus atomus,

[0246] Anagyrus fusciventris, Anagyrus kamali, Anagyrus loecki, Anagyrus pseudococci (Citripar®), Anicetus benefices, Anisopteromalus calandrae, Anthocoris nemoralis (Anthocoris-System®), Aphelinus abdominalis (Apheline®, Aphiline®), Aphelinus asychis, Aphidius colemani (Aphipar®), Aphidius ervi (Ervipar®), Aphidius gifuensis, Aphidius matricariae (Aphipar-M®), Aphidoletes aphidimyza (Aphidend®), Aphidoletes aphidimyza (Aphidoline®), Aphytis lingnanensis, Aphytis melinus, Aprostocetus hagenowii, Atheta coriaria (Staphyline®), Bombus spp., Bombus terrestris (Natupol Beehive®), Bombus terrestris (Beeline®, Tripol®), Cephalonomia stephanoderis, Chilocorus nigritus, Chrysoperla carnea (Chrysoline®), Chrysoperla carnea (Chrysopa®), Chrysoperla rufilabris, Cirrospilus ingenuus, Ci rrospilus quadristriatus, Citrostichus phyllocnistoides, Closterocerus Chamaeleon, Closterocerus spp., Coccidoxenoides perminutus (Pianopar®), Coccophagus cowperi, Coccophagus lycimnia, Cotesia flavipes, Cotesia plutellae, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®), Cybocephalus nipponicus, Dacnusa sibirica, Dacnusa sibirica (Minusa®), Diglyphus isaea (Diminex®), Delphastus catalinae (Delphastus®), Delphastus pusillus, Diachasmimorpha krausii, Diachasmimorpha longicaudata, Diaparsis jucunda, Diaphorencyrtus aligarhensis, Diglyphus isaea, Diglyphus isaea (Miglyphus®, Digline®), Dacnusa sibirica (DacDigline®, Minex®), Diversinervus spp., Encarsia citrina, Encarsia formosa (Encarsia max®, Encarline®, En-Strip®), Eretmocerus eremicus (Enermix®), Encarsia guadeloupae, Encarsia haitiensis, Episyrphus balteatus (Syrphidend®), Eretmoceris siphonini, Eretmocerus californicus, Eretmocerus eremicus (Ercal®, Eretline e®), Eretmocerus eremicus (Bemimix®), Eretmocerus hayati, Eretmocerus mundus (Bemipar®, Eretline m®), Eretmocerus siphonini, Exochomus quadripustulatus, Feltiella acarisuga (Spidend®), Feltiella acarisuga (Feltiline® ), Fopius arisanus, Fopius ceratitivorus, Formononetin (Wirless Beehome®), Franklinothrips vespiformis (Vespop®), Galendromus occidentalis, Goniozus legneri, Habrobracon hebetor, Harmonia axyridis (HarmoBeetle®), Heterorhabditis spp. (Lawn Patrol®), Heterorhabditis bacteriophora (NemaShield HB®, Nemaseek®, Terranem-Nam®, Terranem®, Larvanem®, B-Green®, NemAttack ®, Nematop®), Heterorhabditis megidis (Nemasys H®, BioNem H®, Exhibitline hm®, Larvanem-M®), Hippodamia convergens, Hypoaspis aculeifer (Aculeifer-System®, Entomite-A®), Hypoaspis miles (Hypoline m®, Entomite-M®), Lbalia leucospoides, Lecanoideus floccissimus, Lemophagus errabundus, Leptomastidea abnormis, Leptomastix dactylopii (Leptopar®), Leptomastix epona, Lindorus lophanthae, Lipolexis oregmae, Lucilia caesar (Natufly®), Lysiphlebus testaceipes, Macrolophus caliginosus (Mirical N®, Macroline c®, Mirical®), Mesoseiulus longipes, Metaphycus flavus, Metaphycus lounsburyi, Micromus angulatus (Milacewing®), Microterys flavus, Muscidifurax raptorellus and Spalangia cameroni (Biopar®), Neodryinus typhlocybae, Neoseiulus californicus, Neoseiulus cucumeris (THRYPEX®), Neoseiulus fallacis, Nesideocoris tenuis

[0247] (NesidioBug®, Nesibug®), Ophyra aenescens (Biofly®), Orius insidiosus (Thripor-I®, Oriline i®), Orius laevigatus (Thripor-L®, Oriline I®), Orius majusculus (Oriline m®), Orius strigicollis (Thripor-S®), Pauesia juniperorum, Pediobius foveolatus, Phasmarhabditis hermaphrodita (Nemaslug®), Phymastichus coffea, Phytoseiulus macropilus, Phytoseiulus persimilis (Spidex®, Phytoline p®), Podisus maculiventris (Podisus®), Pseudacteon curvatus, Pseudacteon obtusus, Pseudacteon tricuspis, Pseudaphycus maculipennis, Pseudleptomastix mexicana, Psyllaephagus pilosus, Psyttalia concolor (complex), Quadrastichus spp., Rhyzobius lophanthae, Rodolia cardinalis, Rumina decollate, Semielacher petiolatus, Sitobion avenae (Ervibank®), Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®), Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline sf®, Scia-rid®, Entonem®), Steinernema kraussei (Nemasys L®, BioNem L®, Exhibitline srb®), Steinernema riobrave (BioVector®, BioVektor®), Steinernema scapterisci (Nematac S®), Steinernema spp., Steinernematid spp. (Guardian Nematodes®), Stethorus punctillum (Stethorus®), Tamarixia radiate, Tetrastichus setifer, Thripobius semiluteus, Torymus sinensis, Trichogramma brassicae (Tricholine b®), Trichogramma brassicae (Tricho-Strip®), Trichogramma evanescens, Trichogramma minutum, Trichogramma ostriniae, Trichogramma platneri, Trichogramma pretiosum, Xanthopimpla stemmator; other biologicals including: abscisic acid, bioSea®, Chondrostereum purpureum (Chontrol Paste®), Colletotrichum gloeosporioides (Collego®), Copper Octanoate (Cueva®), Delta traps (Trapline d®), Erwinia amylovora (Harpin) (ProAct®, Ni-HIBIT Gold CST®), Ferri-phosphate (Ferramol®), Funnel traps (Trapline y®), Gallex®, Grower's Secret®, Homo-brassonolide, Iron Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®), MCP hail trap (Trapline f®), Microctonus hyperodae, Mycoleptodiscus terrestris (Des-X®), BioGain®, Aminomite®, Zenox®, Pheromone trap (Thripline ams®), potassium bicarbonate (MilStop®), potassium salts of fatty acids (Sanova®), potassium silicate solution (Sil-Matrix®), potassium iodide + potassiumthiocyanate (Enzicur®), SuffOil-X®, Spider venom, Nosema locustae (Semaspore Organic Grasshopper Control®), Sticky traps (Trapline YF®, Rebell Amarillo®) and Traps (Takitrapline y + b®); and a safener, such as benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including tench lorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil.

[0248] Where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13thEd.; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound "abamectin" is described under entry number (1). Where "[CCN]" is added hereinabove to the particular compound, the compound in question is included in the "Compendium of Pesticide Common Names", which is accessible on the internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; for example, the compound "acetoprole" is described underthe internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0249] Most of the active ingredients described above are referred to hereinabove by their "common name" which is known to the skilled person in the art. In other cases, the active ingredients may be referred to by their IUPAC name The term "CAS number" means the Chemical Abstracts Registry Number. Preferably, the one or more other active ingredients that may optionally present in the compositions of the invention are selected from Alpha-Cypermethrin, Bifenthrin, Broflanilide, Chlorantraniliprole, Clothianidin, Cyantraniliprole, Cypermethrin, Deltamethrin, Dicloromezotiaz, dimpropyridaz, Emamectin (or Emamectin Benzoate), Fluazaindolizine, Flubendiamide, Fluopyram, Imidacloprid, Indoxacarb, Isocycloseram, Lambda-Cyhalothrin, Permethrin, Spinetoram, Spinosad, Spiropidion, Spirotetramat, Sulfoxaflor, Tetraniliprole, Thiamethoxam, Tioxazafen, Bacillus thuringiensis, Helicoverpa armigera Nucleopolyhedrovirus and beta-cyfluthrin.

[0250] The active ingredient mixture of the compounds of Formula (1) or compounds of formula (I) with active ingredients described above comprises preferably in a mixing ratio by weight of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, special preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above all in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.

[0251] (c) Bait formulations

[0252] In some embodiments, a compound of Formula (1) or compound of formula (I) is formulated as a bait formulation. A bait formulation may be used in the control of household pests as per the sixth aspect of the present invention.

[0253] Thus, in some embodiments, said bait composition comprises, in addition to an insecticida lly effective amount of a compound of Formula (1) or compound of formula (I), at least one insect (household pest) food attractant and / or insect (household pest) food flavorant.

[0254] A food attractant provides for the insects' feed uptake (such as a food preferred by the target insect pest) and / or attracts the target insect pest to the insect bait composition when the insect is in the locus or vicinity, or attracts the insect over a distance (specific attractant), even if such food attractant material is not an insect food source, per se.

[0255] A food flavorant (phagostimulants) stimulates insect feeding of the bait material once the insecticide bait is encountered by the target insect pest. It is possible to employ mixtures of such constituents in the bait material. In some cases, a food attractant can also function as a food flavorant.

[0256] Each insect food attractant may be selected from the group consisting of: a harvested grain or legume, a protein, a carbohydrate, a lipid, and a cellulose material.

[0257] A harvested grain or legume may include, for example, wheat, barley, rye, oats, rice, sorghum, soybeans, corn, garbanzo, amaranth or potato. When a harvested grain is used, it may be used in the form of a flour, grit, or grain. Flours or grits are prepared for use in the bait by milling of the harvested grains or cereals to an appropriate size. Other examples include distiller's grain, starch, various bran materials such as wheat bran or rice bran, oatmeal, corn grits, corn chips, corn seeds, corn starch, various mixes such as corn-wheat mix, wheat seeds, whole wheat bread dough, defatted corn grits, brewer's malt, poultry mash, cereal powder such as, for example, wheat powder, maize powder, rice powder and rice bran, and starches such as, for example, potato starch and corn starch.

[0258] A protein may be contained in or obtained from, for example, meat, meat extract and milk powder, fish meal, fish extracts, or seafood, seafood extracts, insects, insect extracts or yeast, yeast extract, peanut butter, yeast lysates or soy protein hydrolysate. Other examples of protein from a natural source are milk protein (such as casein, sodium casein, calcium casein, lactalbumin, dried milk), plant protein (such as gluten, e.g. from wheat; soy extract, peanut extract, zein), animal protein (such as fish meal, meat meal, egg white, liver powder (e.g. from chicken liver or poultry liver), collagen, dried insects (such as crickets) or yeast. Preferred protein is milk protein and animal protein, more preferably animal protein, and especially dried insects.

[0259] A carbohydrate may be any known sugar, monosaccharide or disaccharide or a mixture thereof, preferably a carbohydrate available from a natural source. Examples are saccharose (sucrose), glucose, lactose, fructose, dextrose, maltose. Technical mixtures comprising sugar may also be used, such as granulated sugar, black sugar, brown sugar, honey, molasses. In some embodiments, the sugar is a disaccharide such as saccharose. Other examples include various sugar mixtures with natural polysaccharides and / or proteins such as agar and grape jelly, sucrose and honey syrup, sugar and milk and the like. Additionally, there may be mentioned various sugars such as, for example, sucrose, maltose, arabinose, galactose, sorbitose, dextrose, fructose, sorbitol, corn syrup, maple syrup, molasses, coca-cola syrup, various types of invert sugar (Invertix), molasses honey and the like, and glycerol and the like.

[0260] A lipid may be a plant oil such as canola oil, cottonseed oil, peanut oil or soybean oil, for example.

[0261] A cellulose material may be wood (pine), paper, (corrugated) cardboard, filter paper, purified cellulose and microcrystalline cellulose.

[0262] Examples of a specific food attractant or flavorant include: ethanol, acetic acid, ethyl acetate, citrus pulp, soybean oil, methylamine, dimethylamine, trimethylamine, ethylmethylamine, propylmethylamine, isopropylamine, tert-butylamine, 1-methylpyrrolidine, diethylamine, dimethylacetamide, furfuryl alcohol, 5-methyl-3-heptanone, geranyl butyrate, linalool, 1,3-diethylbenzene, 2-nonanone, (E)-2-hexanoic acid, ammonium acetate, ammonium phosphate, ammonia solution from 10 percent to 30 percent in water, putrescine, cadaverine, trimedlure, a trimedlure isomer, ceralure, a ceralure isomer, 4-[(4-acetyloxy)phenyl]- 2-butanone, methyleugenol, a fluorinated methyleugenol analogue, 1,7-dioxaspiro- 5,5-undecane.

[0263] The bait may include at least one nutritional feeding stimulant as a flavorant (phagostimulant) component which serves to give taste and flavor to the bait composition and / or to enhance feeding by the target insects. Said nutritional feeding stimulant may be selected from the group consisting of: a fatty acid, amino acid, sugar, carbohydrate, pectin, starche, salt, chitin, and essential plant oil. For example, peanut butter oil and apple cider vinegar can be mentioned as phagostimulants. Other examples of phagostimulants that can be employed in a bait formulation are, for example, an extract from meat, fish or insects. Others which are suitable for attraction include natural or synthetic aromas such as, for example, meat aromas, fish aromas, seafood aromas, onion aromas, milk aromas, butter aromas, cheese aromas, fruit aromas such as, for example, aromas of apple, apricot, banana, blackberry, cherry, currant, gooseberry, grapefruit, raspberry or strawberry (pure, syrup or extract).

[0264] A bait composition of the present invention may also contain one or more formulation ingredients selected from the list consisting of: a stabilizer, preservative, carrier, excipient, pheromone, kairomone, binder, gelling agent, surfactant and additive.

[0265] In some embodiments, a carrier is natural or synthetic, and associates with the compound according the first or second aspect of the present invention, facilitating its application to the locus to be treated. This carrier should be inert to the compound according the first or second aspect of the present invention and should be acceptable for use according to the third aspect of the present invention at the treatment locus. Herein the treatment locus refers to the location at which the compound according the first or second aspect of the present invention is made available to the insect pest. In some embodiments, the treatment locus means the area in which the target insect pest or insect pest population is found, is growing, or is established, or the area in which the target insect pest feeds.

[0266] In another embodiment, a food attractant also may serve as a carrier in the bait composition or matrix. For example, dried cobs of maize corn can be ground after removal of the seeds to form a coarse granular "corn grit" that functions as both a food attractant and a carrier in an Agrotis spp. bait composition or matrix.

[0267] A surfactant may be of an emulsifying surfactant or wetting surfactant, an ionic surfactant or a non-ionic surfactant. Said surfactant may be a dispersant, antifoaming agent, penetrating agent, wetting agent, stabilizing agent, sequestering agent and / or antiflocculating agent. Possible surfactants are salts of polyacrylic or lignosulfonic acids; salts of phenolsulfonic or naphthalenesulfonic acids; polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols (particularly alkylphenols or arylphenols); ester- salts of sulfosuccinic acids; taurine derivatives, such as alkyl taurates; phosphoric esters; or esters of alcohols or polyoxyethylated phenols. When the bait composition contains water, the use of at least one surfactant may be desirable.

[0268] Other additives may be selected from the list consisting of: an antifreezing agent, dyestuff, pigment, thickener, adhesive, protective colloids corrosion inhibitor, and a polymer. More generally, the bait formulation of the invention can contain all kinds of solid or liquid additive which are known in the art of insecticides and insecticidal treatments.

[0269] In some embodiments, the bait formulation according to the invention can be in the form of a liquid a paste or a gel or a solid such as a granule, pellet, or powder. A solid bait formulation can be a powder for dusting or for dispersion, a paste, a gel or granular, including extruded, agglomerated or compacted granules, or granules which have been made by impregnation of a powder or pulp material. A solid bait composition can also be a spreadable granular composition based on an appropriate insect food attractant as carrier such as a grain (or a ground corn cob).

[0270] A liquid bait formulation can be a composition which has to be liquid or dispersed in a liquid when applied to a treatment locus including a solution, water-soluble concentrate, emulsifiable concentrate, suspension, suspension concentrate, suspoemulsion, emulsion, wettable powder, paste, gel or dispersible granular composition.

[0271] In some embodiments, an insect bait in accordance with the invention can be associated with various insect bait stations that are known in the art. In a typical insect bait station, a target insect is encouraged to retrieve an appropriate bait composition that contains a compound according the first or second aspect of the present invention from a treatment locus.

[0272] In some embodiments, when the bait formulation according to the invention is prepared in the form of a gel, comprises a matrix-forming crosslinkable polymer from among a material selected from the group consisting of: carrageenan, alginate, gellan gum, xanthan gum and mixtures thereof.

[0273] Optionally, at least one polymeric binder can be used for the function of an extrusion aid, wherein said polymeric binder is a polyvinylpyrrolidone or polysaccharide. A preferred polysaccharide is a cellulose derivative, such as that prepared by chemical, polymeranalogous reactions of cellulose. Exemplary cellulose derivatives are cellulose esters, such as cellulose acetate and cellulose butyrate, and cellulose ethers, such as carboxymethyl cellulose, methyl cellulose, methylhydroxyalkyl cellulose, hydroxyethyl cellulose, carboxymethyl hydroxyethy cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, andhydroxypropyl cellulose. A preferred polymeric binder is a cellulose ether, especially methyl cellulose.

[0274] In a further embodiment, an insect food attractant also may function as a binder in the bait formulation. For example, a plant oil such as soybean oil can be used as a binder for bait granules prepared from various grains or pulps such as citrus pulp.

[0275] An example of a stabilizer includes a calcium salt, such as calcium lactate, calcium chloride and the like.

[0276] An example of an embittering agent includes a hot or bitter substance such as for example cayenne pepper powder, denatorium benzoate and the like.

[0277] An example of a preservative includes sorbic acid, a sorbate, benzoic acid, benzoate, paraoxybenzoic ester, methylisothiazolinone, benzoisothiazolinone, chloromethylisothiazolinone and the like. In some embodiments, an insect bait formulation of the present invention comprises: a) 0.001 to 99.999 percent by weight of a compound according the first or second aspect of the present invention; b) 99.999 to 0.001 percent by weight of an insect food attractant or an insect food flavorant or a mixture thereof.

[0278] In some embodiments, the compound according the first or second aspect of the present invention is present in the bait formulation an amount from 0.005 to 5 % by weight of the bait composition: preferably in an amount from 0.1 to 2 % by weight of the bait composition.

[0279] Non-limiting examples of the insect pests which may be controlled by a bait according to the present invention include the household pests described in the sixth aspect of the present invention.

[0280] USE OF THE COMPOUND(S) OF FORMULAE (1) AND / OR (I) OR COMPOSITIONS COMPRISING ONE OR MORE COMPOUNDS OF FORMULAE (1) AND / OR (I)

[0281] It was surprisingly found that compounds of Formula (1) or compounds of Formula (I) exhibit a desirable effect acting as an insecticide. Therefore, in a fourth aspect, the present invention provides the use of the compound according to the first or second aspect or the composition according to the third aspect in agriculture, preferably as an insecticide, or in animal health, preferably for treating parasitic invertebrate pests, or in or household, preferably for controlling household pests.

[0282] Furthermore, according to a sixth aspect, the present invention provides the use of a compound of Formula (1):

[0283] Formula (1) in controlling household pest, wherein

[0284] A is Ci-haloa Ikyl;

[0285] Q is selected from aryl and heteroaryl;

[0286] R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;

[0287] R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof. In some embodiments, the compound of Formula (1) is not . In some embodiments, . In this connection, it is noted that the above outlined embodiments of A, Q, R, R1, R2, and R3apply as well. Furthermore, the compounds

[0288] can be used in the sixth aspect of the invention.

[0289] Examples of insect pest species which may be controlled by the compounds of Formula (1) or the compounds of Formula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid), Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids), Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper), Nezara spp. (stinkbugs, for example Nezara viridula (southern green shield bug)), Euschistus spp. (stinkbugs), Leptocorisa spp. (stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips), Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis (boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (white flies), Bemisia tabaci (white fly), Ostrinia nubilalis (European corn borer), Spodoptera littoralis (cotton leafworm), Spodoptera frugiperda (fall armyworm), Spodoptera exigua (beet armyworm or small mottled willow moth), Heliothis virescens (tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpa zea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pieris brassicae (white butterfly), Plutella xylostella (diamond back moth), Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locusta migratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp. (rootworms), Panonychus ulmi (European red mite), Panonychus citri (citrus red mite), Tetranychus urticae (two-spotted spider mite), Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpus spp. (flat mites), Boophilus microplus (cattle tick), Dermacentor variabilis (American dog tick), Ctenocephalides felis (cat flea), Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti (mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes), Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplaneta americana (cockroach), Blatta orientalis (cockroach), termites of the Mastotermitidae (for example Mastotermes spp.), the Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulfur eus), Solenopsis geminata (fire ant), Monomorium pharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (biting and sucking lice), Meloidogyne spp. (root knot nematodes), Globodera spp. and Heterodera spp. (cyst nematodes), Pratylenchus spp. (lesion nematodes), Rhodopholus spp. (banana burrowing nematodes), Tylenchulus spp. (citrus nematodes), Haemonchus contortus (barber pole worm), Caenorhabditis elegans_ (vinegar eelworm), Trichostrongylus spp. (gastro intestinal nematodes), Deroceras reticulatum (slug), Dalbulus maidis (leafhopper) and click beetle / wireworm [e.g. Agriotes mancus (wheat wireworm), Agriotes obscurus (dusky wireworm), Agriotes lineatus (lined click beetle), Agriotes sputator (common click beetle)].

[0290] The compounds of the invention are also useful in the field of animal health; e.g. they may be used against parasitic invertebrate pests in or on an animal. Examples of pests include nematodes, trematodes, cestodes, flies, mites, tricks, lice, fleas, true bugs and maggots. The animal may be a non-human animal, e.g. an animal associated with agriculture, e.g. a cow, a pig, a sheep, a goat, a horse, or a donkey, or a companion animal, e.g. a dog or a cat.

[0291] Examples of species of animal health pests include those from the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.; particular examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus; from the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; particular examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; from the order of the Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; particular examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipa Ipis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasa lis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; particular examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp; from the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (e.g. Suppella longipalpa); from the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of multi host ticks) Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; particular examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabar ina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; from the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.; particular examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia xer other mobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi; Gasterophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lecturius, Ctenocephalides felis, Lucilia cuprina; examples of acari include Ornithodoros spp., Ixodes spp., Boophilus spp..

[0292] Preferred examples of parasitic invertebrate pests include fleas, ticks and mites.

[0293] Preferably, the compounds of Formula (1) or the compounds of Formula (I) may be, for example, effective in controlling in insect pests as well animal health pests such as lepidopteran, hemipteran, coleopteran, thysanopteran and dipteran and also other invertebrate pest species preferably Lepidopteran pests preferably selected from Spodoptera, Plutella and Helicoverpa damaging crops or from invertebrate pests preferably selected from the Spodoptera, Plutella, Helicoverpa, Nezara or Leptinotarsa genus.

[0294] In preferred embodiments, the invertebrate pest is selected from the group consisting of: Plutella xylostella, Spodoptera exigua, Helicoverpa armigera, Nezara viridula and Leptinotarsa decemlineata.

[0295] In a preferred embodiment, a compound according to the first or second aspect of the invention or a composition according to the third aspect has improved human and / or environmentally profiles compared to other products used to control insect pests and / or parasitic invertebrate pests and / or household pests.

[0296] The term "household pest" as used herein denotes an arthropod pest that may infest / inhabit a residential building [e.g. house, apartment block (including apartment), orphanage, dormitory, retirement home], educational building (e.g. school, college, university), medical building (e.g. hospital, nursing home), civic building (e.g. arena, cinema, theatre, museum, library), religious building (e.g. church, mosque, temple, shrine, synagogue), government or military building (e.g. court, prison, barrack), commercial or industrial building [e.g. office, agricultural building such as a barn or silo, hotel, casino, shopping centre (including supermarket)]; or transport (e.g. aeroplane, train, ship, including cruise-ship).

[0297] A household pest may be a consumer of non-foodstuff (e.g. wood, paper, carpet), a consumer of foodstuff (e.g. flour, harvested cereal foodstuff, harvested foodstuff grains like rice, nuts) or an animal (including human) parasite.

[0298] A consumer of non-foodstuff may be selected from the group consisting of: ant [e.g. Lasius niger (common black ant), Monomorium pharaonic (pharaoh ant), Solenopsis spp. for example, Solenopsis invicta (RIFA), Solenopsis geminata (tropical fire ant), Solenopsis saevissima (red ant); Camponotus spp. (carpenter ant), Tapinoma sessile (odourous house ant), Monomorium minimum (little black ant), Tetramorium caespitum (pavement ant), Linepithema humile (Argentine ant), Paratrechina longicornis (longhorn crazy ant), Tapinoma melanocephalum (ghost ant)]; carpet beetle (e.g. Anthrenus verbasci, Anthrenus flavipes, Anthrenus schrophulariae, Trogoderma variabile, Attagenus pellio, Attagenus sminovi, Attagenus unicolor); carpet moth (Trichophaga tapetzella); cockroach [e.g. Blattella germanica (German cockroach), Periplaneta americana (American cockroach), Periplaneta australasiae (Australian cockroach), Blatta orientalis (oriental cockroach)]; cricket (e.g. Acheta domesticus); earwig (e.g. Forficula auricularia); fly [e.g. housefly (for example Musca domestica, Fannia canicularis), blowfly (for example, Lucilia spp. such as Lucilia sericata, Calliphora vicina, Calliphora erythrocephala), flesh fly (for example Sarcophaga carnaria)]; pillbug / slater / woodlouse; silverfish (e.g. Lepisma saccharinum); firebrat (Thermobia domestica); and termite [e.g. termite of the Mastotermitidae (for example Mastotermes spp.), the Kalotermitidae (for example Neotermes spp.), the Rhinotermitidae (for example Coptotermes formosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R. hesperus, and R. santonensis) and the Termitidae (for example Globitermes sulfureus)]. A consumer of foodstuff may be selected from the group consisting of: lesser grain borer (Rhyzopertha dominica); cigarette beetle (Lasioderma serricorne); darkling beetle [e.g. confused flour beetle (Tribolium confusum), dark flour beetle (Tribolium destructor), litter beetle (e.g. Alphitobius diaperinus), broadhorned flour beetle (Gnatocerus cornutus), red flour beetle (Tribolium castaneum), yellow mealworm beetle (Tenebrio molitor)]; meal moth [e.g. almond moth (Cadra cautella), raisin moth (Cadra figulilella), Indianmeal moth (Plodia interpunctella), Mediterranean flour moth (Ephestia kuehniella), rice moth (Corcyra cephalonica)]; rice weevil (Sitophilus oryzae); and saw-toothed grain beetle (Oryzaephilus surinamensis).

[0299] An animal parasite may be selected from the group consisting of: bedbug (adult) (e.g. Cimex lectularius, Cimex hemipterus); flea [e.g. Ctenocephalides felis (cat flea)]; louse; mosquito (e.g. Aedes aegypti, Anopheles gambiae, Anopheles maculipennis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis); tick [e.g. Dermacentor variabilis (American dog tick)]; and parasitic mite.

[0300] In preferred embodiments, the household pest is selected from the group consisting of ant [e.g. Lasius niger (common black ant), Monomorium pharaonic (pharaoh ant), Solenopsis spp. for example, Solenopsis invicta (RIFA), Solenopsis saevissima (red ant); Camponotus spp. (carpenter ant), Tapinoma sessile (odourous house ant), Monomorium minimum (little black ant), Tetramorium caespitum (pavement ant), Linepithema humile (Argentine ant), Paratrechina longicornis (longhorn crazy ant), Tapinoma melanocephalum (ghost ant)]; carpet beetle (e.g. Anthrenus verbasci, Anthrenus flavipes, Anthrenus schrophulariae, Trogoderma variabile, Attagenus pellio, Attagenus sminovi, Attagenus unicolor); carpet moth (Trichophaga tapetzella); cockroach [e.g. Periplaneta australasiae (Australian cockroach)]; cricket (e.g. Acheta domesticus); earwig (e.g. Forficula auricularia); fly (e.g. Calliphora vicina); pillbug / slater / woodlouse; silverfish (e.g. Lepisma saccharinum); firebrat (Thermobia domestica); lesser grain borer (Rhyzopertha dominica); cigarette beetle (Lasioderma serricorne); darkling beetle [e.g. confused flour beetle (Tribolium confusum), dark flour beetle (Tribolium destructor), litter beetle (e.g. Alphitobius diaperinus), broadhorned flour beetle (Gnatocerus cornutus), red flour beetle (Tribolium castaneum), yellow mealworm beetle (Tenebrio molitor)]; meal moth [e.g. almond moth (Cadra cautella), raisin moth (Cadra figulilella), Indianmeal moth (Plodia interpunctella), Mediterranean flour moth (Ephestia kuehniella), rice moth (Corcyra cephalonica)]; rice weevil (Sitophilus oryzae); and sawtoothed grain beetle (Oryzaephilus surinamensis).

[0301] In preferred embodiments, the household pest is selected from the group consisting of Musca domestica, Blattella germanica and Lasius niger. In preferred embodiments, the household pest is selected from the group consisting of Musca domestica and Blattella. germanica. In preferred embodiments, the household pest is selected from Lasius niger.

[0302] A further (fifth) aspect of the invention is related to a method for controlling insect pests which comprises applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of a compound according to the first or second aspect of the invention or a composition according to the third aspect of the invention. PREPARATION OF COMPOUNDS OF FORMULAE (1) AND (I)

[0303] In a further (seventh) aspect, the invention further provides an intermediate of Formula (10):

[0304] Formula (10) wherein

[0305] A is Ci-haloa Ikyl;

[0306] Q is selected from aryl and heteroaryl;

[0307] R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; and

[0308] R2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

[0309] Said intermediates are useful in the preparation of a compound according to the first or second aspect of the invention, i.e., a compound of Formula (1) or a compound of Formula (I) as will be described in more detail below.

[0310] In this connection, it is noted that the above outlined embodiments of A, Q, R1, R2, and R3apply as well.

[0311] In a further aspect, the invention further provides compounds of the following formulae:

[0312] which are useful in the preparation of a compound according to the first or second aspect of the invention, i.e., a compound of Formula (1) or a compound of Formula (I) as will be described in more detail below.

[0313] SYNTHESIS OF COMPOUNDS OF FORMULAE (1) AND (I)

[0314] Preparation of compounds of Formula (1) or compounds of Formula (I).

[0315] The compounds of Formula (1) or compounds of Formula (I) according to the first or second aspect of the invention can be produced by methods known to those skilled in the art. The skilled person will appreciate that adaptation of methods known in the art could be applied in the manufacture of the compounds of the present invention. For example, the skilled person will be immediately familiar with standard textbooks such as "Comprehensive Organic Transformations - A Guide to Functional Group Transformations", RC Larock, Wiley-VCH (1999 or later editions); "March's Advanced Organic Chemistry - Reactions, Mechanisms and Structure", MB Smith, J. March, Wiley, (5th edition or later editions); "Advanced Organic Chemistry, Part B, Reactions and Synthesis", FA Carey, RJ Sundberg, Kluwer Academic / Plenum Publications, (2001 or later editions); "Organic Synthesis -The Disconnection Approach", S Warren (Wiley), (1982 or later editions); "Designing Organic Syntheses" S Warren (Wiley) (1983 or later editions); "Heterocyclic Chemistry", J. Joule (Wiley 2010 edition or later editions); ("Guidebook To Organic Synthesis" RK Mackie and DM Smith (Longman) (1982 or later editions), etc., and the references therein as a guide.

[0316] The skilled person is familiar with a range of strategies for synthesising organic and particularly heterocyclic molecules and these represent common general knowledge as set out in text books such as Warren "Organic Synthesis: The Disconnection Approach"; Mackie and Smith "Guidebook to Organic Chemistry"; and Clayden, Greeves, Warren and Wothers "Organic Chemistry".

[0317] The skilled person will exercise his / her judgement and skill as to the most efficient sequence of reactions for the synthesis of a given target compound and will employ protecting groups as necessary. This will depend inter alia on factors such as the nature of other functional groups present in a particular substrate. Clearly, the type of chemistry involved will influence the choice of reagent that is used in the said synthetic steps, the need, and type, of protecting groups that are employed, and the sequence for accomplishing the protection / deprotection steps. These and other reaction parameters will be evident to the skilled person by reference to standard textbooks and to the examples provided herein.

[0318] Sensitive functional groups may need to be protected and deprotected during synthesis of a compound of the invention. This may be achieved by conventional methods, for example as described in "Protective Groups in Organic Synthesis" by TW Greene and PGM Wuts, John Wiley & Sons Inc. (1999), and references therein.

[0319] Compounds of Formula (1) and compounds of Formula (I) can be made according to methods described in WO2013026931. Further possible synthetic routes to exemplary key intermediates and compounds of Formula (1) / compounds of Formula (I) are given below in Schemes (I) to (VII). Suitable intermediates can have the Formula (10) as above-defined or the more specific formulae as above-disclosed. Scheme (I): Scheme (III): Scheme (VI):

[0320] EXAMPLES

[0321] The present invention will be demonstrated in more detail by way of examples which are not intended to be limiting the present invention as defined in the appended claims.

[0322] General Methods

[0323] Flash chromatography was carried out using a Biotage Isolera 4, with Biotage® SNAP KP-Sil cartridges, packed with 50 pm silica particles with a surface area of 500 m2 / g, or alternative cartridges (e.g. Puriflash, produced by Interchim) where stated, or using silica gel (40-63 pm particles). Visualisation was carried out with UV light (254 nm) and by staining with either potassium permanganate, phosphomolybdic acid (PMA) or ninhydrin solutions.

[0324] All1H NMR spectra were obtained on a Bruker AVIII 400 with 5mm QNP or Bruker AVI 500 with 5mm QNP. Chemical shifts are expressed in parts per million (6) and are referenced to the solvent. Coupling constants J are expressed in Hertz (Hz).

[0325] MS was carried on a Waters HCIass UPLC-QDA UV-MS system using Methods A / C (high pH) or Method B / D (low pH); and on Shimadzu Nexera module UPLC System using Method E (low pH):

[0326] Method A (5 min basic pH)

[0327] Mobile phases: Water (A) / Acetonitrile (B) / Water: Acetonitrile 50: 50 1%NH4OH (C)

[0328] 3 pl injection, Column XBridge BEH C18 Column 3.0 x 50mm @ 35°C.

[0329] Method B (5 min acidic pH)

[0330] Mobile phases: Water (A) / Acetonitrile (B) both with 0.1% (v / v) formic acid

[0331] 3 pl injection, Column: HSelect HSS Column 3.0 x 50mm @ 35°C.

[0332] Method C (15 min basic pH)

[0333] Mobile phases: Water (A) / Acetonitrile (B) both with 0.1% (v / v) ammonia

[0334] Injection volume: 10 pL, Column: YMC-Triart C18 50 x 2 mm, 5 urn. Flow rate: 0.8 mL / min.

[0335] Method D (15 min acidic pH)

[0336] Mobile phases: Water (A) / Acetonitrile (B) both with 0.1% (v / v) formic acid

[0337] 10 pl injection, Column: YMC-Triart C18 50 x 2 mm, 5 pm. Flow rate: 0.8 mL / min

[0338] Method E (7 min acidic pH)

[0339] LCMS was carried on a Waters Alliance e2695 PDA-MS system.

[0340] Mobile phases: 0.1 % v / v formic acid in Water (A) / MethanokAcetonitrile (1:1) (B)

[0341] 5 pl injection, Column Agilent, Zorbax Eclipse XDB C18 (50 x 4.6) mm, 5pm @ 35°C.

[0342] Method F (5 min, basic pH)

[0343] LCMS was carried on a Waters H Class UPLC-SQD 2 PDA-MS system Mobile phases: 5 mM Ammonium Acetate in Water (A) / 5 mM Ammonium Acetate in Water:Acetonitrile (10:90) (B)

[0344] 2 pl injection, Column XBridge C18 Column 3 x 50mm, 3.5 u @ 40°C.

[0345] Method G (12 min, basic pH)

[0346] LCMS was carried on a Waters H Class UPLC-SQD 2 PDA-MS system.

[0347] Mobile phases: 5 mM Ammonium Acetate in Water (A) / 5 mM Ammonium Acetate in Water:Acetonitrile (10:90) (B)

[0348] 2 pl injection, Column XBridge C18 Column 3 x 50mm, 3.5 u @ 40°C. LogD was measured using the shake flask methodology. The aqueous phase used is a lOmM solution of sodium phosphate buffer adjusted to pH 7.4 and Octanol is used as the organic solvent. Quantitation of test compound in both phases is via LC-MS / MS.

[0349] Chromatographic Hydrophobicity Index (CHI) LogD was determined using the following protocol: lOpL of each lOmM DMSO calibration standard compound was added to 950pL of methanol, and separately lOpL of lOmM DMSO Test compound is added to 990pL of methanol. All test solutions were thoroughly mixed and then analysed by LC-UV. Retention times (RT) of all compounds and calibration mixture standards are recorded. The mean RT values were used to form a linear regression between RT and CHI . The gradient and intercept were used to convert the RT data of the compounds of interest into CHI values. CHI values of the compounds were then converted into a logarithmic scale (CHI LogD7.4) using the CHI values and hydrogen bond donor counts (HBC).

[0350] The formula used for the conversion to CHI LogD7.4 is as follows:

[0351] CHI LogD7.4 = 0.064CHI + 0.37HBC - 1.

[0352] All reagents were obtained from commercial suppliers and used as supplied unless otherwise stated.

[0353] All compounds are named using ChemBioDraw Ultra Version 23.5.0.

[0354] The abbreviations used in the following are the abbreviations commonly used in this technical field. For example, the following abbreviations are used:

[0355] CDI 1,1-Carbonyldiimidazole

[0356] EtOAc Ethyl Acetate

[0357] EtOH Ethanol

[0358] MeOH Methanol

[0359] PE Petroleum ether r.t. Room temperature

[0360] THF Tetra hydrofuran

[0361] MgSC Magnesium Sulfate nd Not determined

[0362] DCM Dichloromethane

[0363] DBU l,8-Diazabicyclo[5.4.0]undec-7-ene sat. Saturated Intermediates

[0364] Intermediate A: 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3- yl)-2-methylbenzohydrazide

[0365] A solution of 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)- 2-methylbenzoic acid (826 mg, 1.89 mmol) in THF (10 mL) was treated with GDI (461 mg, 2.84 mmol). The reaction was stirred at r.t. for lh and then added to a solution of hydrazine hydrate (1.04 g, 1.03 mL, 35% Wt, 11.4 mmol) in THF (2.5 mL). The reaction mixture was stirred at r.t. for 18 h. The reaction was quenched with water and diluted with EtOAc, the layers were separated and the organic extract was washed with brine, dried (MgSC ) and evaporated in vacuo to give the title compound (as a white solid in good yield). LCMS (Method A): 2.57 min (448.0, [M-H] )

[0366] Intermediate B-K

[0367] The following Intermediates were prepared using the general method described in Intermediate A from the appropriate intermediates or commercial materials.

[0368]

[0369] Intermediate L: Methyl 4-acetyl-2-iodobenzoate

[0370] A solution of 4-acetyl-2-iodobenzoic acid (900 mg, 3.10 mmol) in MeOH (6 mL) was treated with a catalytic amount of H2SO4 (82.7 pL, 1.55 mmol) and heated at 60°C for 17h and to reflux for 6h. The solvent was evaporated in vacuo and the residue was neutralized using sat. NaHCCh (aq) (lOmL) and extracted using DCM (3xl0mL). The organic extracts were combined and washed with brine (15mL). The organic extracts were passed through a phase separator and evaporated in vacuo to give the title compound as a yellow solid. LCMS (Method A) 2.26 min.

[0371] Intermediate M: Methyl (Z)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-2-enoyl)-2- iodobenzoate

[0372] To a solution of Intermediate K (751 mg, 2.47 mmol) and l-(3,5-dichloro-4-fluorophenyl)- 2,2,2-trifluoroethan-l-one (967 mg, 3.70 mmol) in Toluene (5 mL) was added DIPEA (400 pL, 2.30 mmol) and it was heated to 80°C for 18h. Acetic anhydride (302 pL, 3.21 mmol) and DIPEA (559 pL, 3.21 mmol) was added to the reaction and it was stirred at 80°C for 52h. The reaction was allowed to cool to r.t. and quenched with sat. NaHCOs (aq). Organic matter was extracted into EtOAc (2 x 40 mL). The organic extracts were washed with water, dried (MgSO4) and evaporated in vacuo. The crude material was purified by column chromatography eluting with 0 - 100% EtOAc / PE to yield the title compound as an orange solid in good yield. LCMS (Method A) 3.42 min (542.9, 544.9, 547.0, [M-H] ).

[0373] Intermediate N: methyl 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)-2-iodobenzoate

[0374] A solution of Intermediate L (695 mg, 1.27 mmol) in DCM (5 mL) and Water (1.2 mL) was treated with tetrabutylammonium bromide (41 mg, 127.1 nmol), hydroxylamine hydrochloride (114 mg, 1.65 mmol) and DBU (380 pL, 2.54 mmol). The reaction mixture was stirred for 18h at r.t. and then quenched with IM HCI (aq) (30 mL). Organic matter was extracted into DCM (2 x 15 mL). The organic extracts were washed with water, dried and evaporated in vacuo to give the title compound as a red solid in a good yield. LCMS (Method A) 3.52 min (559.9, 561.9 [M-H]j.

[0375] Intermediate O: 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3- yl)-2-iodobenzoic acid

[0376] A solution of Intermediate M (650 mg, 1.16 mmol) in THF (3.5 mL) was treated with lithium hydroxide monohydrate (485 mg, 11.6 mmol) and the reaction mixture was stirred at 40°C overnight. The reaction mixture was concentrated under vacuum. The residue was diluted with IM HCI (25 mL) and extracted into EtOAc (2 x 25mL). The organic extracts were combined and washed with water (25mL) and concentrated under vacuum. The crude material was purified by column chromatography eluting with 0 - 100% EtOAc / PE to yield the title compound as an orange oil in good yield. LCMS (Method A) 2.03 min (545.9, 547.9 [M-H] j. Examples

[0377] Example 1 - (E)-N'-(4-cyanobenzylidene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-

[0378] (trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzohydrazide

[0379] A solution of Intermediate A. (35.0 mg, 77.7 pmol) in EtOH (1 mL) was treated with 4- cyanobenzaldehyde (10.2 mg, 77.7 pmol). The reaction mixture was stirred at reflux for 18h. The solvent was evaporated in vacuo. The crude material was purified by column chromatography eluting with 0 - 100% EtOAc / PE to yield the title compound ((E)-N'-(4- cyanobenzylidene)-4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5- dihydroisoxazol-3-yl)-2-methylbenzohydrazide) as a white solid in good yield. LCMS (Method A): 2.93 min (561.1, [M-H] j. LogD > 5.5.

[0380] Examples 2-43

[0381] The following Examples were prepared usingthe general method described in Example 1 from the appropriate intermediates or commercial materials.

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388] Examples 44-141

[0389] The following Examples were prepared usingthe general method described in Example 1 from the appropriate intermediates or commercial materials.

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402] Comparative Examples

[0403] The following Comparative Examples 1 and 2 were prepared using the general method described in Example 1 from the appropriate commercial starting materials.

[0404] Comparative Example 1 BIOLOGICAL EXAMPLES

[0405] In the following, biological examples are shown which serve to illustrate the invention, but which are not understood as being limiting the scope of the invention.

[0406] Certain compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lowerapplication rates, if necessary, for example 25 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.

[0407] In particular, some compounds in accordance with the present invention were tested fortheir activity against Plutella xylostella, Spodoptera exigua, Helicoverpa armigera, Nezara viridula, Leptinotarsa decemlineata, German cockroaches, Houseflies and Black ants.

[0408] Plutella xylostella: contact / feeding activity

[0409] Test compounds were diluted in an IF-50 water / tween solution. Cabbage leaf discs were immersed in the test solutions and dried. The dried leaves were placed in petri dishes containing a moistened piece of filter paper and infested with 5 second-instar diamondback moth larvae. The dishes were placed in a growth chamber for 4 days and percent mortality of the larvae recorded.

[0410] A direct comparison of the biological performance of Example 1 and Comparative Example 1 as well as of Example 7 and Comparative Example 2 is shown in Table 1 below.

[0411] Table 1

[0412] Table 1 confirms that the compounds according to the invention show greater efficacy at lower application rates against Plutella xylostella compared to known compounds such as Comparative Example 1 and Comparative Example 2.

[0413] Furthermore, the following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-37, Ex-38, Ex-39, Ex-40, Ex-41, Ex-42, Ex-43.

[0414] The following compounds also gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-44, Ex-45, Ex-46, Ex-47, Ex-48, Ex-494, Ex-50, Ex-51, Ex-52, Ex-53, Ex-54, Ex-55, Ex-56, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-62, Ex-63, Ex-64, Ex-65, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-72, Ex-73, Ex-74, Ex-75, Ex-77, Ex-78, Ex-79, Ex-80, Ex-81, Ex-82, Ex-83, Ex-84, Ex-85, Ex-86, Ex-87, Ex-88, Ex-89, Ex-90, Ex-91, Ex-92, Ex-94, Ex-95, Ex-96, Ex-97, Ex-98, Ex-99, Ex-100, Ex-101, Ex-102, Ex-103,

[0415] Ex-104, Ex-105, Ex-106, Ex-107, Ex-108, Ex-109, Ex-110, Ex-112, Ex-113, Ex-114, Ex-115,

[0416] Ex-116, Ex-117, Ex-118, Ex-119, Ex-120, Ex-121, Ex-122, Ex-123, Ex-124, Ex-125, Ex-126,

[0417] Ex-127, Ex-128, Ex-130, Ex-131, Ex-132, Ex-133, Ex-134, Ex-135, Ex-136, Ex-137, Ex-138,

[0418] Ex-139, Ex-140, Ex-141.

[0419] Spodoptera exigua: contact / feeding activity

[0420] Test compounds were diluted in an IF-50 water / tween solution. Broad bean leaf discs were immersed in the test solutions and dried. The dried leaves were placed in petri dishes filled with a small layer of 2% agar solution and infested with 5 third-instar fall armyworm moth larvae. The dishes were placed in a growth chamber for 72 h and percent mortality of the larvae recorded.

[0421] Table 2

[0422] Table 2 shows that the compounds according to the invention show great efficacy at application rates of lower than 100 ppm against Spodoptera exigua.

[0423] Table 3

[0424] Table 3 confirms that the compounds according to the invention also show greater efficacy at lower application rates against Spodoptera exigua compared to known compounds such as Comparative Example 1 and Comparative Example 2.

[0425] Furthermore, the following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-2, Ex-4, Ex-6, Ex-11, Ex-12, Ex-16, Ex-21, Ex-23, Ex-24, Ex-27, Ex-28, Ex-33.

[0426] The following compounds also gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-3, Ex-9, Ex-10,

[0427] Ex-13, Ex-15, Ex-17, Ex-18, Ex-19, Ex-26, Ex-29, Ex-30, Ex-31, Ex-32, Ex-34, Ex-35, Ex-37, Ex-38,

[0428] Ex-39, Ex-40, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45, Ex-47, Ex-48, Ex-49, Ex-50, Ex-52, Ex-53, Ex-54,

[0429] Ex-55, Ex-56, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-63, Ex-65, Ex-66, Ex-67, Ex-68, Ex-72, Ex-73,

[0430] Ex-74, Ex-75, Ex-78, Ex-79, Ex-82, Ex-86, Ex-88, Ex-91, Ex-92, Ex-95, Ex-97, Ex-103, Ex-122, Ex-126, Ex-133, Ex-134, Ex-135, Ex-136, Ex-138, Ex-141.

[0431] Helicoverpa armigera: feeding activity

[0432] Test compounds were diluted in an IF-50 water / tween solution. Second-instar larvae were exposed to treated diet for 72 h and percent mortality of the larvae recorded.

[0433] The following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-1 , Ex-2, Ex-4, Ex-7, Ex-11 , Ex-12, Ex-16, Ex-21 , Ex-24. Nezara viridula: contact feeding activity

[0434] Test compounds were diluted in an IF-50 water / tween solution. Suitable green beans were cut into 3 pieces of 10 cm each and dipped in the test solutions. The dried green beans were placed on the experimental arena with 5 second-instar nymphs of Nezara viridula. The dishes were placed in a growth chamber for 7 days and percent mortality of the nymphs recorded.

[0435] The following compounds gave an effect of at least 50% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-1 , Ex-21 .

[0436] Leptinotarsa decemlineata: contact feeding activity

[0437] Test compounds were diluted in an IF-50 water / tween solution. Leaf discs and 2 Leptinotarsa decemlineata beetles were sprayed with 5 mL freshly made solution. The dishes were placed in a growth chamber for 3 days and percent mortality of the beetles recorded.

[0438] The following compounds gave an effect of at least 80% control in at least one of the two categories (mortality or growth inhibition) at an application rate of 100 ppm: Ex-1 , Ex-7, Ex- 21.

[0439] German cockroaches (B. germanica)

[0440] The compounds were incorporated into peanut butter to provide a bait formulation. 0.1 g of the treated bait (i.e. bait formulation) was applied onto 2cm x 2cm square acetate tiles, before entry into the test. Ten insects were counted, from a stock culture, into the test arenas. Following a 24-hour acclimatisation / starvation period, during which time the harbourage and water source is provided however no food source is present, insects were checked to ensure that they are all alive and active. Any dead insects were removed and replaced. The bait formulation was then introduced into each test arena. Mortality (and moribund) assessments were carried out daily, post treatment application, for a total of 10 days.

[0441] The following compounds gave an effect of at least 80% control at an application rate of 1% w / w: Ex-1, Ex-7 and Ex-21.

[0442] Houseflies (M. domestica)

[0443] The compounds were incorporated into sugar syrup to provide a bait formulation. O.l g of the treated bait (i.e. bait formulation) was applied onto 2cm x 2cm square acetate tiles, before entry into the test. Ten insects were counted, from a stock culture, into the test arenas. Following a 24-hour acclimatisation / starvation period, during which time the harbourage and water source is provided however no food source is present, insects were checked to ensure that they are all alive and active. Any dead insects were removed and replaced. The bait formulation was then introduced into each test arena. Mortality (and moribund) assessments were carried out daily, post treatment application, for a total of 3 days. The following compounds gave an effect of at least 80% control at an application rate of 1% w / w: Ex-1, Ex-7 and Ex-21.

[0444] Black Ants (L. niger)

[0445] The compounds were incorporated into sugar syrup to provide a bait formulation. O.l g of the treated bait (i.e. bait formulation) was applied onto 2cm x 2cm square acetate tiles, before entry into the test. 20 insects were counted, from a stock culture, into the test arenas. Following a 24-hour acclimatisation / starvation period, during which time the harbourage and water source is provided however no food source is present, insects were checked to ensure that they are all alive and active. Any dead insects were removed and replaced. The bait formulation was then introduced into each test arena. Mortality (and moribund) assessments were carried out daily, post treatment application, for a total of 14 days.

[0446] The following compounds gave an effect of at least 80% control at an application rate of 1% w / w: Ex-7 and Ex-21.

Claims

1. CLAIMS1. A compound of Formula (1):Formula (1) whereinA is Ci-haloa Ikyl;Q is selected from aryl and heteroaryl;R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;R1, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; andR2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

2. The compound of claim 1, wherein A is selected from CF3 and CHF2.

3. The compound of claim 1, wherein R2is selected from halogen and Ci-ha loa I ky I, or R2is hydrogen when R3is Ci-ha loa Ikyl or hydrogen, or when A is CHF2, CH2F, CCI3 or CCIF2.

4. The compound of any of claims 1-3, wherein R1, R3are each independently selected from hydrogen, halogen, and CF3.

5. The compound of any of claims 1-4, wherein R2is selected from halogen and CF3, or R2is hydrogen when R3is CF3 or hydrogen, or when A is CHF2.

6. A compound according to the following Formula (I):Formula (I) whereinA is selected from CF3 and CHF2;Q is selected from aryl and heteroaryl; and R is selected from aryl and heteroaryl;or an agrochemically acceptable salt, a stereoisomer, an enantiomer, a tautomer, a rotamer or a deuterated compound thereof.

7. The compound of any of claims 1-6, wherein is substituted or unsubstituted aryl and preferably naphthyl or phenyl, more preferably Q is phenyl.

8. The compound of any of claims 1-7, wherein Q is naphthyl, or phenyl, which are each independently and optionally substituted with one or more substituents each independently selected from Ci-Ce alkyl group, Ci-Ce haloalkyl group, Ci-Ce alkoxy group, Ci-Ce haloalkoxy group, nitro, cyano, NH2, carbocyclyl, and halogen, preferably selected from chloro, bromo, fluoro, iodo, methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, nitro, cyano, and cyclopropyl.

9. The compound of any of claims 1-8, wherein Q iswhereinY1, Y2and Y3are each independently CH or nitrogen;R4is hydrogen, halogen, cyano, nitro, NH2, C1-C2 alkyl, C1-C2 haloalkyl, C3-C5 cycloalkyl, C3-C5 halocycloalkyl, C1-C2 alkoxy, C1-C2 haloalkoxy; and indicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I).

10. The compound of any of claims 1-9, wherein Qis selected from the following moieties:whereinindicates the attachment points to the remainder of the compound of Formula (1) or the compound of Formula (I).

11. The compound of any of claims 1-10, wherein R is substituted or unsubstituted phenyl, pyridine, pyridazine, pyrimidine, pyrazine, pyrazole, furane, thiophene, oxazole, imidazole, thiazole, benzothiadiazole or thiadiazole.

12. The compound of any of claims 1-11, wherein R is unsubstituted or substituted with one or more substituents selected independently from halogen, nitrile, nitro, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, NHSO2-C1-3 alkyl, NH-C1-3 alkyl, N(CI-3alkyl)2, NH-C1-3 haloalkyl, NHC(O)-CI-3alkyl, S-C1-3 alkyl, S-C1-3 haloalkyl, SO2NH2, SO2-C1.3 alkyl, S(O)(NH)Me, S(O)Me(N(CN)), C(O)Me(N(CN)), hydroxyl, C(O)N H-CI-3 alkyl, C(O)NH2, cycloalkyl, and heterocyclyl, preferably selected from F, Cl, Br, I, nitrile, nitro, methyl, CHF2, CMeF2, OMe, OCHF2, vinyl, ethynyl, NHSO2Me, NHMe, NMe2, NHCF3, NHC(O)Me, SMe, SCF3, SO2NH2, SO2Me, S(O)(NH)Me, S(O)Me(N(CN)), hydroxyl, C(O)NHMe, C(O)NH2, cyclopropyl, pyrimidyl, and pyrazolyl.

13. The compound of any of claims 1-12, wherein R is selected from the following moieties:R-29 R-30 R-31 R-32 R-3314. The compound of any of claims 1-13, wherein A is CF3.

15. The compound of any of claims 1-14 which conforms to the following Formula (la):Formula (la), wherein A, Q and Rare defined as in any of claims 1-14.

16. The compound of any of claims 1-15 which is selected from the following compounds:- 091 -17. The compound of claim 1, which is selected from the following compounds:- WL -- 691 -8. The compound of any of claims 1 to 17, wherein the compound of Formula (1) or the compound of Formula (I) corresponds to one of the following compounds of Formula (A), (B), (C), (D), (E), (F), (G), (H), (J) and (K):Formula (A) Formula (B)19. A composition comprising a compound according to any of claims 1-18, one or more auxiliaries and / or adjuvants, and optionally one or more other active ingredients.

20. The composition of claim 19 which is an agrochemical and / or parasitic composition and / or household composition.

21. Use of a compound accordingto any of claims 1-18 ora composition accordingto claim 19 or 20 in agriculture or in animal health or in household.

22. The use according to claim 21 in controlling insect pests or parasitic invertebrate pests or household pests.

23. The use according to claim 21 or 22, wherein the insect pest is selected from lepidopteran, hemipteran, coleopteran, thysanopteran and dipteran and otherinvertebrate pest species preferably from the Lepidopteran pests and preferably the insect pest is selected from Spodoptera, Plutella and Helicoverpa.

24. The use according to claim 21 or 22, wherein the parasitic invertebrate pest is selected from the parasitic invertebrate pests such as fleas, ticks and mites.

25. A method for controlling insect pests which comprises applying to a pest, to a locus of a pest, to a plant susceptible to attack by a pest or to a plant propagation material an effective amount of a compound as defined in any of claims 1-18 or a composition as defined in claim 19 or 20.

26. Use of a compound of Formula (1):Formula (1) in controlling household pest, whereinA is Ci-haloa Ikyl;Q is selected from aryl and heteroaryl;R is selected from aryl, carbocyclylalkyl, heterocyclyl, Ci-Ce alkyl, and C(O)O-Ci-Ce alkyl;R1, R2, R3are each independently selected from hydrogen, halogen, and Ci-ha loa Ikyl; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

27. An intermediate of Formula (10):Formula (10) whereinA is Ci-haloa Ikyl;Q is selected from aryl and heteroaryl;R1, R3are each independently selected from hydrogen, halogen, and Ci-haloalkyl; andR2is selected from halogen and Ci-haloalkyl, or R2is hydrogen when R3is Ci-haloalkyl or hydrogen, or when A is not CF3; or a salt, a stereoisomer, an enantiomer, a tautomer, a rotamer, a N-oxide, or a deuterated compound thereof.

28. The intermediate according to claim 27, wherein the formula (10) has one of the following formulae:

29. Use of a compound of claim 27 or 28 in the preparation of a compound according to any of claims 1-18.

30. A compound of any of claims 1-18 or a composition according to claim 19 or 20 which has improved human and / or environmentally profiles compared to other products used to control insect pests and / or parasitic invertebrate pests and / or household pests.

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