Pesticidally active cyclic amine compounds

Abstract

Compounds of formula (I) [Formula 1] TIFF2023513575000113.tif46158 (wherein the substituents are as defined in claim 1) and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds can be used as insecticides.

Description

[Technical Field]

[0001] The present invention relates to pesticidally active, in particular insecticidally or acaricidally active, cyclic amine compounds, preferably azetidinyl, piperidinyl and piperazinyl arylcarbonyl compounds having acaricidal activity, processes for their preparation, compositions containing these compounds and their use for controlling animal pests, including arthropods, in particular insects or representatives of the order Acarina. [Background technology]

[0002] WO 2015032280, CN106316931, WO 2017195703, WO 2019039429, WO 2019082808, JP 2019077618, and JP 2019085371 describe certain piperidinyl and piperazinylpyridinyl carbonyl compounds for use in controlling plant-damaging pests. Summary of the Invention [Problem to be solved by the invention]

[0003] Novel pesticidally active azetidinyl, piperidinyl and piperazinyl arylcarbonyl compounds have now been found. [Means for solving the problem]

[0004] Thus, in a first aspect, the present invention provides a compound of formula (I) [ka] (In the formula, R 1 is CN, C(=S)NH2 or C1-C6 haloalkyl; R 2 is H, OH, halogen, C1-C6 alkoxy or C1-C6 haloalkoxy; R 3is H, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; R 4 is H, halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, or C1-C6 haloalkoxy; R 5 is phenyl, 1 to 3 substituents R 6 phenyl substituted with, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), 1 to 3 substituents R 7 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with Q is a cyclic amine represented by formula IIa or a cyclic amine represented by formula IIb; [ka] where the arrow indicates the bond to the carbonyl group; p 1 is 0, 1 or 2 and indicates the number of methylene groups; p 2 is 0, 1 or 2 and indicates the number of methylene groups; q 1 is 1 or 2 and indicates the number of methylene groups; q 2 is 1 or 2 and indicates the number of methylene groups; X is hydrogen, hydroxyl, C1-C6 alkoxy, cyano, or halogen; Y is cyano, C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylsulfanyl-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C3-C6 alkenylsulfanyl-C1-C6 alkyl, C3-C6 alkenylsulfinyl-C1-C6 alkyl, C3-C6 alkenylsulfonyl-C1-C6 alkyl, C3-C6 alkynylsulfanyl-C1-C6 alkyl, C3-C6 alkynylsulfinyl-C1-C6 alkyl, C3-C6 alkynylsulfonyl-C1-C6 alkyl, C1-C6 alkynylcarbonyl, C1-C6 alkoxycarbonylamino, R a R b NC(O), R c C(O)NR d , R e SO2NR f , R g ON=CR h , a 4-6 membered non-aromatic heterocyclic ring system (wherein one or two carbons are independently replaced by nitrogen, oxygen, sulfur, or sulfonyl), phenyl, 1-3 substituents R 8 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 9 is a 5- or 6-membered monocyclic heteroaryl substituted with X and Y together form the group R m forms a double bond to the nitrogen substituted with O; A is cyano, C1-C6 cyanoalkyl, C2-C6 cyanoalkenyl, C3-C6 cyanocycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C6 halocycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C2-C6 alkenyloxycarbonyl, C2-C6 alkynyloxycarbonyl, C1-C6 alkylsulfanyl-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, R i SO2, R j R k NSO2, phenyl, 1 to 3 substituents R10 phenyl, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), or 1-3 substituents R 11 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with R a and R b are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl and C3-C6 halocycloalkyl and C1-C6 alkylsulfonyl; R c and R d are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 halocycloalkyl; R f is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl; R e and R i is independently selected from C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 halocycloalkyl; R g and R h are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 halocycloalkyl; R j and R kare independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, and C3-C6 halocycloalkyl; R m is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl or C3-C6 halocycloalkyl; R 6 , R 7 , R 8 , R 9 , R 10 , R 11 are independently selected from halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylsulfonyl, and C1-C6 haloalkylsulfanyl; or agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of compounds of formula I. DETAILED DESCRIPTION OF THE INVENTION

[0005] Compounds of formula (I) having at least one basic centre can, for example, form acid addition salts with strong inorganic acids, such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acids; strong organic carboxylic acids, for example C1-C4 alkanecarboxylic acids which are unsubstituted or substituted, for example, by halogens, such as acetic acid; saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid; hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or for example benzoic acid; or organic sulfonic acids, for example C1-C4 alkane- or arylsulfonic acids which are unsubstituted or substituted, for example, by halogens, such as methane- or p-toluenesulfonic acid. The compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example inorganic salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0006] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example in agriculturally usable salt form.

[0007] N-oxides are oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds, as described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0008] The compounds of formula (I) according to the present invention also include hydrates which may be formed during salt formation.

[0009] As used herein, "C1-C n The term "alkyl" refers to a saturated straight or branched hydrocarbon radical having 1 to n carbon atoms attached via any of the carbon atoms, such as any one of the radicals methyl, ethyl, n-propyl, n-butyl, n-pentyl, 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-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0010] As used herein, "C2-C n The term "alkenyl" refers to a straight or branched alkenyl chain having 2 to n carbon atoms and one or two double bonds, for example, ethenyl, prop-1-enyl, but-2-enyl.

[0011] As used herein, "C2-C n The term "alkynyl" refers to a straight or branched alkynyl chain having 2 to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl, but-3-ynyl.

[0012] As used herein, "C3-C n The term "cycloalkyl" refers to a 3 to n-membered cycloalkyl group, such as cyclopropane, cyclobutane, cyclopentane, and cyclohexane.

[0013] As used herein, "C1-C nThe term "alkoxy" refers to a straight or branched saturated alkyl radical having 1 to n carbon atoms (as defined above) attached through an oxygen atom, i.e., for example, any one of methoxy, ethoxy, n-propoxy, 1-methoxyethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy radicals. As used herein, "haloC1-C n The term "alkoxy" refers to a C1-C alkyl radical in which one or more hydrogen atoms on the alkyl radical are replaced by the same or different halo atoms. n refers to an alkoxy radical (examples include trifluoromethoxy, 2-fluoroethoxy, 3-fluoropropoxy, 3,3,3-trifluoropropoxy, 4-chlorobutoxy).

[0014] Halogen is generally fluorine, chlorine, bromine or iodine. This applies correspondingly to halogen in combination with other meanings, such as haloalkyl.

[0015] As used herein, "C1-C nThe term "haloalkyl" refers to a straight or branched saturated alkyl radical having 1 to n carbon atoms bonded via any of the carbon atoms (as defined above), wherein some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, and any one of 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, and nonafluorobutyl. The term "C1-C2 fluoroalkyl" refers to a C1-C2 alkyl radical having 1, 2, 3, 4 or 5 fluorine atoms, such as any one of difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl. Similarly, as used herein, "C2-C n Haloalkenyl" or "C2-C n The term "haloalkynyl" refers to C-C alkyl groups each substituted with one or more halo atoms, which may be the same or different. n Alkenyl or C2-C nSimilarly, as used herein, "C3-C" refers to an alkynyl moiety. n The term "halocycloalkyl" refers to a C-C alkyl group substituted with one or more halo atoms, which may be the same or different. n It refers to a cycloalkyl group.

[0016] As used herein, "C1-C n The term "cyanoalkyl" refers to a C1-C6 alkyl group having 1 to n carbon atoms (as defined above). n "C1-C4 alkyl radicals" refers to alkyl radicals in which one of the hydrogen atoms in these radicals is replaced by a cyano group, such as cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-(cyanomethyl)-2-ethyl, 1-(methyl)-2-cyanoethyl, 4-cyanobutyl, etc. Similarly, "C1-C4 alkyl radicals" refers to alkyl radicals in which one of the hydrogen atoms in these radicals is replaced by a cyano group, such as cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-(cyanomethyl)-2-ethyl, 1-(methyl)-2-cyanoethyl, 4-cyanobutyl, etc. n Cyanoalkenyl" or "C1-C n The term "cyanoalkynyl" refers to C-C alkyl groups each of which is substituted with one of the hydrogen atoms in the corresponding moiety by a cyano group. n Alkenyl or C1-C n Refers to the alkynyl moiety.

[0017] As used herein, "C1-C n Alkylsulfanyl-C1~C n The term "alkyl" refers to an alkyl radical in which one of the carbon atoms has been replaced by a sulfur atom.

[0018] As used herein, "C1-C n Alkylsulfinyl-C1~C n The term "alkyl" refers to an alkyl radical in which one of the carbon atoms is replaced by an S(=O) group.

[0019] As used herein, "C1-C n Alkylsulfonyl-C1~C n The term "alkyl" refers to an alkyl radical in which one of the carbon atoms is replaced by an S(=O)2 group.

[0020] As used herein, the term "4-6 membered non-aromatic heterocyclic ring system in which one or two carbons are replaced by nitrogen, oxygen, sulfur, or sulfonyl" refers to a cyclic group in which one or two carbon atoms in the ring are independently replaced by nitrogen, oxygen, sulfur, or sulfonyl, and the ring is bonded to the remainder of the compound through a carbon or nitrogen atom. Examples are azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, 2-oxopyrrolidinyl, 2-oxotetrahydrofuranyl, 1,1-dioxo-1,2-thiazolidinyl, 1,3-dioxolanyl, 1,3-dithiolanyl, 2-oxooxazolidinyl, piperidinyl, tetrahydropyranyl, 2-oxopiperidinyl, 1,1-dioxothiazinanyl, 2-oxotetrahydropyranyl, 1,3-dioxolanyl, 1,3-dithianyl, 2-oxo-1,3-oxazinanyl.

[0021] As used herein, "phenyl-C1-C n The term "alkyl" refers to an alkyl radical substituted on a phenyl ring. Phenyl-C n If there is substitution on the alkyl group, the substitution is on the phenyl ring.

[0022] As used herein, "C1-C n Alkoxy-C1~C n The term "alkyl" refers to C1-C n It refers to an alkyl radical substituted with an alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

[0023] As used herein, "C1-C n The term "alkoxycarbonyl" refers to a carbonyl (C=O) radical (through which C1-C n C1-C bonded to the alkoxycarbonyl) nIt refers to an alkoxy group. Examples are methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl and tert-butyloxycarbonyl.

[0024] As used herein, the term "C1-C6 alkoxycarbonylamino" refers to an amino (NH) radical (through which C1-C n C1-C bonded to the remainder of the compound n It refers to an alkoxycarbonyl group. Examples are:

[0025] As used herein, "C2-C n The term "alkenyloxycarbonyl" refers to a carbonyl (C=O) radical bonded by an oxygen atom to a C-C n It refers to an alkenyl group where the bond to the rest of the compound is through the carbon atom of the carbonyl. Examples are vinyloxycarbonyl and allyloxycarbonyl.

[0026] As used herein, "C2-C n The term "alkynyloxycarbonyl" refers to a carbonyl (C=O) radical bonded by an oxygen atom to a C-C n

[0033] Refers to an alkynyl group where the bond to the rest of the compound is through the carbon atom of the carbonyl. Examples are propargyloxycarbonyl (2-prop-2-ynoxycarbonyl) and 2-pent-3-ynoxycarbonyl. Substituent R g ON=CR h is expressed by the following general formula: [ka]

[0027] As used herein, the term "5- or 6-membered monocyclic heteroaryl" refers to a 5- or 6-membered aromatic ring having 1 to 3 carbon atoms independently substituted by nitrogen, sulfur, or oxygen. Examples include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl (e.g., 1.2.4 triazolyl), furanyl, thiophenyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, and thiadiazolyl. Examples are heteroaryls J-1 to J-35 shown in Scheme A below. Preferred heteroaryls are J-1, J-16, J-18, or J-20.

[0028] As used herein, the term "9- or 10-membered bicyclic heteroaryl" refers to a 9- or 10-membered aromatic ring composed of two rings having 1 to 3 carbon atoms independently substituted by nitrogen, sulfur, or oxygen (heteroatoms can be in one ring or distributed between the two). Examples are purinyl, quinolinyl, cinnolinyl, quinoxalinyl, indolyl, indazolyl, benzimidazolyl, benzothiophenyl, and benzothiazolyl. Scheme A: Heteroaryls J-1 to J-35 [ka]

[0029] As used herein, the term "control" refers to reducing the number of pests so that damage to plants or plant-derived products is reduced, eradicating pests, and / or preventing further pest damage.

[0030] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, and storage of plant-derived products (such as fruit, grain, and lumber); and pests associated with damage to man-made structures. The term pest encompasses all stages in the life cycle of a pest.

[0031] As used herein, the term "effective amount" refers to the amount of a compound or salt thereof that produces a desired effect in single or multiple applications.

[0032] As used herein, for example in formulae IV-aa and IV-ba, the zigzag line represents the point of connection / attachment to the remainder of the compound.

[0033] An effective amount is readily determined by one skilled in the art by the use of known techniques and by observing results obtained under analogous circumstances. Determining an effective amount takes into account numerous factors, including, but not limited to, the type of plant or plant-derived product to which it is applied; the pest to be controlled and its life cycle; the particular compound applied; the type of application; and other relevant circumstances.

[0034] Embodiments according to the present invention are provided as follows.

[0035] In one embodiment of each aspect of the invention, R 1 teeth, A. CN, C(=S)NH2 or C1-C3 haloalkyl; or B. CN, C(=S)NH2, difluoromethyl or trifluoromethyl; or C.CN.

[0036] In one embodiment of each aspect of the invention, R 2 teeth, A. hydrogen, halogen, C1-C6 alkoxy or C1-C6 haloalkoxy; or B. hydrogen, halogen, C1-C3 alkoxy or C1-C3 haloalkoxy; or C. hydrogen, fluorine, chlorine, methoxy, difluoromethoxy, or trifluoromethoxy; or D. It is hydrogen.

[0037] In one embodiment of each aspect of the invention, R 3 teeth, A. hydrogen, OH, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyloxy; or B. hydrogen, halogen, C1-C6 alkyl, or C1-C6 haloalkyl, C1-C6 alkoxy, or C1-C6 haloalkyloxy; or C. hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy or C1-C3 haloalkyloxy; or D. hydrogen, chlorine, fluorine, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, or pentafluoroethyl; or E. hydrogen, methyl, ethyl, methoxy, ethoxy, difluoromethyl, trifluoromethyl, or pentafluoroethyl; or F. Methyl, methoxy, ethoxy, difluoromethyl or trifluoromethyl.

[0038] In one embodiment of each aspect of the invention, R 4 teeth, A. hydrogen, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C3 cycloalkyl, C3-C3 halocycloalkyl, C1-C3 alkoxy or C1-C3 haloalkyloxy; or B. hydrogen, cyano, or halogen; or C. hydrogen, cyano, fluorine or chlorine; or D. It is hydrogen or cyano.

[0039] In one embodiment of each aspect of the invention, R 5 teeth, A. Phenyl, 1 to 3 substituents R 6 phenyl, 5- or 6-membered monocyclic heteroaryl or 1 to 3 substituents R 7 5- or 6-membered monocyclic heteroaryl substituted with B. Phenyl or 1 to 3 substituents R 6 phenyl substituted with; or C. 1 to 3 substituents R 6is a phenyl substituted with

[0040] In one embodiment of each aspect of the invention, Q is A. Cyclic amines represented by formula IIa, wherein p 1 and p 2 are both 0 or 1; X is hydrogen, hydroxyl, C1-C3 alkoxy, cyano, or halogen; Y is cyano, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylsulfanyl-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C3-C6 alkenylsulfanyl-C1-C6 alkyl, C3-C6 alkenylsulfinyl-C1-C6 alkyl, C3-C6 alkenylsulfonyl-C1-C6 alkyl, C3-C6 alkynylsulfanyl-C1-C6 alkyl, C3-C6 alkynylsulfinyl-C1-C6 alkyl, C3-C6 alkynylsulfonyl-C1-C6 alkyl, C1-C6 alkynylcarbonyl, C1-C6 alkoxycarbonylamino, R a R b NC(O), R e SO2NR f , R g ON=CR h , a 4-6 membered non-aromatic heterocyclic ring system (wherein one or two carbons are independently replaced by nitrogen or sulfonyl), phenyl, 1-3 substituents R 8 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 9 or X and Y together represent the group R m forms a double bond to a nitrogen substituted with O; or [ka] B. Cyclic amines represented by formula IIa, wherein p 1 and p 2are both 0 or 1; X is hydrogen or hydroxyl; Y is C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, C1-C3 alkylsulfonyl-C1-C3 alkyl, C3-C4 alkenylsulfanyl-C1-C3 alkyl, C3-C4 alkenylsulfinyl-C1-C3 alkyl, C3-C4 alkenylsulfonyl-C1-C3 alkyl, C3-C4 alkynylsulfanyl-C1-C3 alkyl, C3-C4 alkynylsulfinyl-C1-C3 alkyl, C3-C4 alkynylsulfonyl-C1-C3 alkyl, R a R b NC(O), R e SO2NR f , R g ON=CR h , a 4-6 membered non-aromatic heterocyclic ring system (wherein one or two carbons are independently replaced by nitrogen or sulfonyl), a 5 or 6 membered monocyclic heteroaryl, or one to three substituents R 9 or X and Y together represent the group R m forms a double bond to a nitrogen substituted with O; or C. Cyclic amines represented by formula IIa, wherein p 1 and p 2 are both 0 or 1; X is hydrogen or hydroxyl; Y is C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, C1-C3 alkylsulfonyl-C1-C3 alkyl, C3-C4 alkenylsulfanyl-C1-C3 alkyl, C3-C4 alkenylsulfinyl-C1-C3 alkyl, C3-C4 alkenylsulfonyl-C1-C3 alkyl, C3-C4 alkynylsulfanyl-C1-C3 alkyl, C3-C4 alkynylsulfinyl-C1-C3 alkyl, C3-C4 alkynylsulfonyl-C1-C3 alkyl, R a R b NC(O), R e SO2NR f , R g ON=CR h, a 4-6 membered non-aromatic heterocyclic ring system (wherein one or two carbons are independently replaced by nitrogen or sulfonyl), a 5 or 6 membered monocyclic heteroaryl, or one to three substituents R 9 or X and Y together represent a group R m forms a double bond to a nitrogen substituted with O; or D. Cyclic amines represented by formula IIa, wherein p 1 and p 2 are both 0 or 1; X is hydrogen or hydroxyl; Y is C1-C3 alkylsulfanyl-methyl, C1-C3 alkylsulfinyl-methyl, C1-C3 alkylsulfonyl-methyl, C3-C4 alkenylsulfanyl-methyl, C3-C4 alkenylsulfinyl-methyl, C3-C4 alkenylsulfonyl-methyl, C3-C4 alkynylsulfanyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl or X and Y together form a double bond to a nitrogen substituted with methoxy or ethoxy; or E. Cyclic amines represented by formula IIa, wherein p 1 and p 2are both 1; X is hydrogen; Y is C1-C3 alkylsulfanyl-methyl, C1-C3 alkylsulfinyl-methyl, C1-C3 alkylsulfonyl-methyl, C3-C4 alkenylsulfanyl-methyl, C3-C4 alkenylsulfinyl-methyl, C3-C4 alkenylsulfonyl-methyl, C3-C4 alkynylsulfanyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfonyl-methyl methyl, methanesulfonylamido, ethanesulfonylamido, 1,1-dioxo-1,2-thioazolidin-2-yl, 1,2,4-oxadiazol-3-yl, 2-pyridyl, substituted 2-pyridyl, or substituted 1,2,4-oxadiazol-3-yl, where each substituent is 1 to 3 substituents independently selected from chlorine and methyl; or X and Y together form a double bond to nitrogen substituted with methoxy or ethoxy; or F. A cyclic amine represented by formula IIb; 1 and q 2 are both 1; A is cyano, C1-C6 cyanoalkyl, C2-C6 cyanoalkenyl, C3-C6 cyanocycloalkyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C3-C6 halocycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C2-C6 alkenyloxycarbonyl, C2-C6 alkynyloxycarbonyl, C1-C6 alkylsulfanyl-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, R i SO2, R j R k NSO2, phenyl, 1 to 3 substituents R 10 phenyl, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), or 1-3 substituents R 11 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with [ka] G. A cyclic amine represented by formula IIb; 1 and q 2 are both 1; A is cyano, C1-C3 cyanoalkyl, C2-C4 cyanoalkenyl, C3-C4 cyanocycloalkyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C3-C4 halocycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl, C2-C4 alkenyloxycarbonyl, C2-C4 alkynyloxycarbonyl, C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, R i SO2, R j R k NSO2, phenyl, 1 to 3 substituents R 10 phenyl, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), or 1-3 substituents R 11 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with H. A cyclic amine represented by formula IIb; 1 and q 2 are both 1; A is cyano, C1-C3 cyanoalkyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl, C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, R i SO2 or 1 to 3 substituents R 11 is a 5- or 6-membered monocyclic heteroaryl substituted with I. Cyclic amines represented by formula IIb; 1 and q 2 are both 1; A is cyano, C1-C3 cyanoalkyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl, C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, R iSO2), or a 6-membered monocyclic heteroaryl substituted with 1 to 3 substituents independently selected from fluorine and chlorine; or J. A cyclic amine represented by formula IIb; 1 and q 2 are both 1; A is cyano, cyanomethyl, cyanoethyl, 2,2,2-trifluoroethyl, vinyloxycarbonyl, butyloxycarbonyl, methylsulfanylmethyl, ethylsulfanylethyl, methylsulfanylethyl (i.e., CHSCHCH), ethylsulfinylethyl, ethylsulfinylmethyl, ethylsulfonylethyl, ethylsulfonylmethyl, methylsulfonylmethyl, 4-chloro-phenyl, or pyridyl substituted with 1 to 3 substituents independently selected from fluorine, chlorine, trifluoromethyl, and difluoromethyl; or K. A cyclic amine represented by formula IIb; 1 and q 2 are both 1; and A is cyano, cyanomethyl, cyanoethyl, CH3SCH2CH2, or pyridyl substituted with 1 to 3 substituents independently selected from fluorine, chlorine, trifluoromethyl, and difluoromethyl.

[0041] In one embodiment of each aspect of the invention, X is A. hydrogen, hydroxyl, C1-C3 alkoxy, cyano, or halogen; or B. hydrogen, hydroxyl, or C1-C3 alkoxy; or C. hydrogen, or hydroxyl; or D. It is hydrogen.

[0042] In one embodiment of each aspect of the invention, R a and R b is, independently, A. hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl and C1-C3 alkylsulfonyl; or B. hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl and C1-C3 alkylsulfonyl; or C. hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, or C1-C3 alkylsulfonyl; or D. hydrogen, C1-C3 alkyl, or C1-C3 alkylsulfonyl; or E. selected from hydrogen, methyl, ethyl, methylsulfonyl, or ethylsulfonyl.

[0043] In one embodiment of each aspect of the invention, R c and R d is, independently, A. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or B. C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or C. C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 halocycloalkyl; or D. C1-C3 alkyl and C1-C3 haloalkyl; or E. Selected from methyl, ethyl, difluoromethyl and trifluoromethyl.

[0044] In one embodiment of each aspect of the invention, R f teeth, A. hydrogen, C1-C3 alkyl, or C3-C4 cycloalkyl; or B. hydrogen or C1-C3 alkyl; or C. Hydrogen, methyl and ethyl.

[0045] In one embodiment of each aspect of the invention, R e teeth, A. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl or C3-C4 halocycloalkyl; or B. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl or C3-C4 halocycloalkyl; or C. C1-C3 alkyl or C1-C3 haloalkyl; or D. Methyl, ethyl, difluoromethyl or trifluoromethyl.

[0046] In one embodiment of each aspect of the invention, R i teeth, A. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl or C3-C4 halocycloalkyl; or B. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl or C3-C4 halocycloalkyl; or C. C1-C3 alkyl or C1-C3 haloalkyl; or D. Methyl, ethyl, difluoromethyl or trifluoromethyl.

[0047] In one embodiment of each aspect of the invention, R g and R h is, independently, A. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or B. C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or C. C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 halocycloalkyl; or D. C1-C3 alkyl and C1-C3 haloalkyl; or E. methyl, ethyl, difluoromethyl and trifluoromethyl; or F. Selected from methyl and ethyl.

[0048] In one embodiment of each aspect of the invention, R j and R k is, independently, A. C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or B. C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl and C3-C4 halocycloalkyl; or C. C1-C3 alkyl, C1-C3 haloalkyl and C3-C4 halocycloalkyl; or D. C1-C3 alkyl and C1-C3 haloalkyl; or E. methyl, ethyl, difluoromethyl and trifluoromethyl; or F. Selected from methyl and ethyl.

[0049] In one embodiment of each aspect of the invention, R m teeth, A. C1-C4 alkyl; or B. methyl, ethyl, or propyl; or C. Methyl or ethyl.

[0050] In one embodiment of each aspect of the invention, R 6 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy, C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or D. Selected from fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylsulfanyl and methylsulfonyl.

[0051] In one embodiment of each aspect of the invention, R 7 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or D. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or E. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or F. halogen, C1-C3 alkyl and C1-C3 haloalkyl and C1-C3 haloalkoxy; or G. Selected from fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy and difluoromethoxy.

[0052] In one embodiment of each aspect of the invention, R 8 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or D. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or E. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or F. halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy; or G. Selected from fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy and difluoromethoxy.

[0053] In one embodiment of each aspect of the invention, R 9 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or D. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or E. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or F. halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy; or G. fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy and difluoromethoxy; or H. Selected from fluorine, chlorine, methyl and ethyl.

[0054] In one embodiment of each aspect of the invention, R 10 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or D. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or E. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or F. halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy; or G. Selected from fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy and difluoromethoxy.

[0055] In one embodiment of each aspect of the invention, R 11 teeth, A. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C4 haloalkenyl, C2-C4 alkynyl, C2-C4 haloalkynyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or B. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy; C1-C3 alkylsulfonyl and C1-C3 haloalkylsulfanyl; or C. halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or D. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or E. halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; or F. halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 haloalkoxy; or G. fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy and difluoromethoxy; or H. Selected from fluorine, chlorine, methyl, and ethyl.

[0056] The present invention therefore provides a compound having the substituents Q, R as defined above. 1 , R 2 , R 3 , R 4 and R 5 In all combinations / permutations of Q, compounds of formula (I) are available. Thus, for example, when Q is in embodiment K (i.e., Q is a cyclic amine represented by formula IIb; where q 1 and q 2 are both 1; A is cyano, cyanomethyl, cyanoethyl, CH3SCH2CH2, or pyridyl substituted with 1 to 3 substituents independently selected from fluorine, chlorine, trifluoromethyl, and difluoromethyl; R 1 is the first embodiment (i.e., R 1 is CN, C(=S)NH2 or C1-C6 haloalkyl; R 2In embodiment D (i.e., R 2 is hydrogen); R 3 In embodiment A (i.e., R 3 is hydrogen, OH, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, or C1-C6 haloalkyloxy; R 4 In embodiment B (i.e., R 4 is hydrogen, cyano, or halogen; R 5 In embodiment B (i.e., R 5 is phenyl or 1 to 3 substituents R 6 phenyl substituted with R 6 In embodiment C (i.e., R 6 is halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy; C1-C3 haloalkoxy, C1-C3 alkylsulfonyl, or C1-C3 haloalkylsulfanyl).

[0057] Compounds of formula I are of formula Ia and Ib [ka] and the substituents X, Y, R in formula Ia can be represented by 1 , R 2 , R 3 , R 4 and R 5 are as defined for formula I; the substituents A, R in formula Ib 1 , R 2 , R 3 , R 4 and R 5 is as defined for formula I.

[0058] In one embodiment of each aspect of the invention, the compound of formula (Ia) has as X hydrogen, hydroxyl, C1-C6 alkoxy, cyano, or halogen; and as Y cyano, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylsulfanyl-C1-C6 alkyl, C1-C6 alkylsulfinyl-C1-C6 alkyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C3-C6 alkenylsulfanyl-C1-C6 alkyl, C3-C6 alkenylsulfinyl-C1-C6 alkyl, C3-C6 alkenylsulfonyl-C1-C6 alkyl, C3-C6 alkynylsulfanyl-C1-C6 alkyl, C3-C6 alkynylsulfinyl-C1-C6 alkyl, C3-C6 alkynylsulfonyl-C1-C6 alkyl, C1-C6 alkynylsulfonyl-C1-C6 alkyl, C1-C6 alkynylcarbonyl, C1-C6 alkoxycarbonylamino, R a R b NC(O), R e SO2NR f , R g ON=CR h , a 4-6 membered non-aromatic heterocyclic ring system (wherein one or two carbons are independently replaced by nitrogen or sulfonyl), phenyl, 1-3 substituents R 8 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 9 or X and Y together represent a group R m forms a double bond to the nitrogen substituted with O; R 1 CN, C(=S)NH2 or C1-C3 haloalkyl; R 2 R has hydrogen, halogen, C1-C6 alkoxy, or C1-C6 haloalkoxy; 3 R is hydrogen, OH, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, or C1-C6 haloalkyloxy; 4R is hydrogen, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C3 cycloalkyl, C3-C3 halocycloalkyl, C1-C3 alkoxy, or C1-C3 haloalkyloxy; 5 as phenyl, 1 to 3 substituents R 6 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 7 5- or 6-membered monocyclic heteroaryl substituted with a , R b , R e , R f , R g , R h , R m , R 6 , R 7 , R 8 , R 9 is as defined in the first aspect.

[0059] In one embodiment of each aspect of the present invention, the compound of formula (Ib) may comprise, as A, cyano, C1-C3 cyanoalkyl, C2-C4 cyanoalkenyl, C3-C4 cyanocycloalkyl, C1-C3 haloalkyl, C2-C3 haloalkenyl, C3-C4 halocycloalkyl, C1-C3 alkoxy-C1-C3 alkyl, C1-C3 alkoxycarbonyl, C2-C4 alkenyloxycarbonyl, C2-C4 alkynyloxycarbonyl, C1-C3 alkylsulfanyl-C1-C3 alkyl, C1-C3 alkylsulfinyl-C1-C3 alkyl, R i SO2, R j R k NSO2, phenyl, 1 to 3 substituents R 10 phenyl, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), or 1-3 substituents R 11 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with R 1 CN, C(=S)NH2 or C1-C3 haloalkyl; R 2R has hydrogen, halogen, C1-C6 alkoxy or C1-C6 haloalkoxy; 3 R is hydrogen, OH, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy or C1-C6 haloalkyloxy; 4 R is hydrogen, cyano, halogen, C1-C3 alkyl, C1-C3 haloalkyl, C3-C3 cycloalkyl, C3-C3 halocycloalkyl, C1-C3 alkoxy, or C1-C3 haloalkyloxy; 5 as phenyl, 1 to 3 substituents R 6 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 7 5- or 6-membered monocyclic heteroaryl substituted with i , R j , R k , R 6 , R 7 , R 10 , R 11 is as defined in the first aspect.

[0060] In one embodiment of each aspect of the invention, the compound of formula (Ia) has as X hydrogen; and as Y C1-C3 alkylsulfanyl-methyl, C1-C3 alkylsulfinyl-methyl, C1-C3 alkylsulfonyl-methyl, C3-C4 alkenylsulfanyl-methyl, C3-C4 alkenylsulfinyl-methyl, C3-C4 alkenylsulfonyl-methyl, C3-C4 alkynylsulfanyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkenylsulfon ... alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynylsulfinyl-methyl, C3-C4 alkynyl R is an alkyl group selected from the group consisting of alkynylsulfonyl-methyl, methanesulfonylamido, ethanesulfonylamido, 1,1-dioxo-1,2-thioazolidin-2-yl, 1,2,4-oxadiazol-3-yl, 2-pyridyl, substituted 2-pyridyl, and substituted 1,2,4-oxadiazol-3-yl, wherein each substituent is 1 to 3 substituents independently selected from chlorine and methyl; or X and Y together form a double bond to a nitrogen substituted with methoxy or ethoxy; ... 1As such, we have CN;R 2 R has hydrogen; 3 R is methyl, methoxy, ethoxy, difluoromethyl, or trifluoromethyl; 4 R has hydrogen or cyano; 5 1 to 3 substituents R 6 wherein R 6 is fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylsulfanyl, or methylsulfonyl.

[0061] In one embodiment of each aspect of the invention, the compound of formula (Ib) has as A cyano, cyanomethyl, cyanoethyl, CH3SCH2CH2, or pyridyl substituted with 1 to 3 substituents independently selected from fluorine, chlorine, trifluoromethyl, and difluoromethyl; R 1 As such, we have CN;R 2 R has hydrogen; 3 R has methyl, methoxy, ethoxy, difluoromethyl or trifluoromethyl as 4 R has hydrogen or cyano; 5 1 to 3 substituents R 6 wherein R 6 is fluorine, chlorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylsulfanyl, or methylsulfonyl.

[0062] In a second aspect, the present invention makes available a composition comprising a compound of formula (I) as defined in the first aspect, one or more adjuvants and diluents and optionally one or more other active ingredients.

[0063] In a third aspect, the present invention makes available a method for combating and controlling insects, acaridae, nematodes or molluscs, which comprises applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect.

[0064] In a fourth aspect, the present invention makes available a method for the protection of plant propagation material from attack by insects, mites, nematodes or mollusks, which comprises treating the propagation material or the locus in which the propagation material is planted with an effective amount of a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect.

[0065] In a fifth aspect, the present invention makes available plant propagation material, such as seeds, which comprises, has been treated with or has attached thereto a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect.

[0066] In a further aspect, the present invention provides a method of controlling parasites in or on an animal in need thereof, the method comprising administering an effective amount of a compound of formula (I) as defined in the first aspect. The present invention further provides a method of controlling ectoparasites on an animal in need thereof, the method comprising administering an effective amount of a compound of the first aspect. The present invention further provides a method of preventing and / or treating diseases transmitted by ectoparasites, the method comprising administering to an animal in need thereof an effective amount of a compound of formula (I) as defined in the first aspect.

[0067] The compounds of formula (I) can be prepared by those skilled in the art by following known methods. More specifically, the compounds of formula I and intermediates can be prepared as described below in the schemes and examples. The specific stereogenic centers are left unspecified for the sake of brevity and are not intended to limit the teachings of the schemes in any way.

[0068] The processes for preparing the compounds of formula (I) according to the invention are carried out by methods known to those skilled in the art.

[0069] Compounds of formula (I) are novel and can be prepared according to Scheme 1 by the coupling of known amide coupling reagents, such as 1-[bis(dimethylamino)-methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) and a base, such as Hunig's base, in a suitable solvent, such as dimethylformamide (DMF) or dimethylacetamide (DMA), to give acids III (wherein R 1 , R 2 , R 3 , R 4 and R 5 are as defined above) with an amine IV-a or IV-b (where X, Y, A, p 1 , p 2 , q 1 and q 2 is as defined above). Piperidines IV-a or piperazines IV-b are commercially available, known from the literature, or can be prepared by one skilled in the art. Scheme 1: [ka]

[0070] Alternatively, compounds of formula (I) can be prepared according to Scheme 2 by the reaction of an acid chloride V (where R 1 , R2 , R 3 , R 4 and R 5 are as defined above) with an amine IV-a or IV-b (where X, Y, A, p 1 , p 2 , q 1 and q 2 can be prepared by reacting Scheme 2: [ka]

[0071] Acid chloride V (where R 1 , R 2 , R 3 , R 4 and R 5 is as defined above) can be converted to the corresponding acid III (wherein R is as defined above) by treatment with, for example, oxalyl chloride or thionyl chloride in an inert solvent such as DCM or THF in the presence of a catalytic amount of DMF at a temperature between 20° C. and 100° C., preferably 25° C., according to Scheme 3 1 , R 2 , R 3 , R 4 and R 5 can be prepared from Scheme 3: [ka]

[0072] Acid III (where R 1 , R 2 , R 3 , R 4 and R 5 is as defined above) can be converted to the corresponding ester VI (where R 1 , R 2, R 3 , R 4 and R 5 is as defined above, and R 12 It can be prepared by hydrolysis of a hydroxybenzoate (wherein = C1-C6 alkyl). Scheme 4: [ka]

[0073] Ester VI (where R 1 , R 2 , R 3 , R 4 and R 5 is as defined above) can be prepared by reacting compound VII (wherein R 1 , R 2 , R 3 , R 4 is as defined above, and LG 1 can be prepared by a palladium-catalyzed cross-coupling reaction of a leaving group, such as iodine, bromine, chlorine, or a sulfonate, such as trifluoromethanesulfonate, with a boronic acid VIII or a stannane reagent IX. Palladium-catalyzed cross-coupling reactions are known to those skilled in the art. These reactions can be carried out at temperatures from below 0°C up to the boiling point of the solvent system, with a variety of palladium catalysts, such as tetrakis(triphenylphosphine)palladium(0) or palladium(II) acetate and triphenylphosphine, in a variety of organic or aqueous solvents compatible with these conditions. Scheme 5: [ka]

[0074] The compounds of formula (I) according to the following Tables 1 to 20 can be prepared according to the above methods. The following examples are intended to illustrate the invention and to show preferred compounds of formula (I) in the form of compounds of formula (Ia). [ka]

[0075] Each of Tables 1 to 20 following Table M below contains 864 compounds of formula (Ia), wherein R 1 , R 3 and R 6 has the value shown in each row in Table M, and Y and X have the values ​​shown in the associated Tables 1-20.

[0076] Thus, compound 1.1 corresponds to a compound of formula (Ia), where R 1 , R 3 and R 6 is as defined in row 1 of Table M, Y and X are as defined in Table 1; compound 14.14 corresponds to the compound of formula (Ia), where R 1 , R 3 and R 6 is as defined in row 14 of Table M, Y and X are as defined in Table 14, etc.

[0077] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10] [Table 1-11] [Table 1-12] [Table 1-13] [Table 1-14] [Table 1-15] [Table 1-16] [Table 1-17] [Table 1-18] [Table 1-19] [Table 1-20] [Table 1-21] [Table 1-22] [Table 1-23]

[0078] Table 1: This table discloses 864 compounds 1.1 to 1.864 of formula (Ia), where Y is 5-methyl-1,2,4-oxadiazol-3-yl, X is hydrogen, and R 1 , R3 , and R 6 is as defined in Table M. For example, compound No. 1.1 has the following structure: [ka]

[0079] Table 2: This table discloses 864 compounds 2.1 to 2.864 of formula (Ia), where Y is 1-methyl-1,2,4-triazol-3-yl, X is hydrogen, and R 1 , R 3 , and R 6 is as defined in Table M.

[0080] Table 3: This table discloses 864 compounds 3.1 to 3.864 of formula (Ia), where Y is 3,5-dichloropyridin-2-yl, X is hydrogen, and R 1 , R 3 , and R 6 is as defined in Table M.

[0081] Table 4: This table discloses 864 compounds 4.1 to 4.864 of formula (Ia), where Y is 3-chloro-5-(trifluoromethyl)pyridin-2-yl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0082] Table 5: This table discloses 864 compounds 5.1 to 5.864 of formula (Ia), where Y is phenyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0083] Table 6: This table discloses 864 compounds 6.1 to 6.864 of formula (Ia), where Y is phenyl, X is hydroxy, and R 1, R 3 and R 6 is as defined in Table M.

[0084] Table 7: This table discloses 864 compounds 7.1 to 7.864 of formula (Ia), where Y is 4-chloro-phenyl-1-yl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0085] Table 8: This table discloses 864 compounds 8.1 to 8.864 of formula (Ia), where Y is 4-chloro-phenyl-1-yl, X is hydroxyl, and R 1 , R 3 and R 6 is as defined in Table M.

[0086] Table 9: This table discloses 864 compounds 9.1 to 9.864 of formula (Ia), where Y is methylsulfanylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0087] Table 10: This table discloses 864 compounds 10.1 to 10.864 of formula (Ia), where Y is methylsulfinylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0088] Table 11: This table discloses 84 compounds of formula (Ia) 11.1 to 11.864, where Y is methylsulfonylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0089] Table 12: This table discloses 864 compounds 12.1 to 12.864 of formula (Ia), where Y is ethylsulfanylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0090] Table 13: This table discloses 864 compounds 13.1 to 13.864 of formula (Ia), where Y is ethylsulfinylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0091] Table 14: This table discloses 864 compounds 14.1 to 14.864 of formula (Ia), where Y is ethylsulfonylmethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0092] Table 15: This table discloses 864 compounds 15.1 to 15.864 of formula (Ia), where Y is 1,1-dioxo-1,2-thioazolidin-2-yl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0093] Table 16: This table discloses 864 compounds 16.1 to 16.864 of formula (Ia), where Y is (E)-methoxyiminomethyl, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0094] Table 17: This table discloses 864 compounds 17.1 to 17.864 of formula (Ia), where Y is (E)-ethoxyiminomethyl, X is hydrogen, and R1 , R 3 and R 6 is as defined in Table M.

[0095] Table 18: This table discloses 864 compounds 18.1 to 18.864 of formula (Ia), where Y is N,N-dimethyl-carboxamide, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0096] Table 19: This table discloses 864 compounds 19.1 to 19.864 of formula (Ia), where Y is methanesulfonamide, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0097] Table 20: This table discloses 864 compounds 20.1 to 20.864 of formula (Ia), where Y is cyano, X is hydrogen, and R 1 , R 3 and R 6 is as defined in Table M.

[0098] Specific examples of compounds of the present invention are those of formula (Ib) in Tables 21 to 35 below: [ka] where R 1 , R 3 and R 6 is as defined above in Table M.

[0099] Each of the following Tables 21 to 35 contains 864 compounds of formula (Ib), where R 1 , R 3 and R 6has the value shown in each row in Table M, and A has the value shown in the associated Tables 21 to 35. Thus, compound 21.1 corresponds to the compound of formula (Ib), where R 1 , R 3 and R 6 is as defined in row 1 of Table M, A is as defined in Table 21; compound 30.14 corresponds to the compound of formula (Ib), where R 1 , R 3 and R 6 is as defined in row 14 of Table M, A is as defined in Table 30, etc.

[0100] Table 21: This table discloses 864 compounds 21.1 to 21.864 of formula (Ib), where A is 3,5-dichloropyridin-2-yl and R 1 , R 3 and R 6 is as defined in Table M. For example, compound No. 1.1 has the following structure: [ka]

[0101] Table 22: This table discloses 864 compounds 22.1 to 22.864 of formula (Ib), where A is 3-chloro-5-(trifluoromethyl)pyridin-2-yl and R 1 , R 3 and R 6 is as defined in Table M.

[0102] Table 23: This table discloses 864 compounds 23.1 to 23.864 of formula (Ib), where A is 3-chloro-pyridin-2-yl and R 1 , R 3 and R 6 is as defined in Table M.

[0103] Table 24: This table discloses 864 compounds 24.1 to 24.864 of formula (Ib), where A is cyano and R 1 , R 3 and R 6 is as defined in Table M.

[0104] Table 25: This table discloses 864 compounds 25.1 to 25.864 of formula (Ib), where A is cyanomethyl and R 1 , R 3 and R 6 is as defined in Table M.

[0105] Table 26: This table discloses 864 compounds 26.1 to 6.864 of formula (Ib), where A is cyanoethyl and R 1 , R 3 and R 6 is as defined in Table M.

[0106] Table 27: This table discloses 864 compounds 27.1 to 27.864 of formula (Ib), where A is 2,2,2-trifluoroethyl and R 1 , R 3 and R 6 is as defined in Table M.

[0107] Table 28: This table discloses 864 compounds 28.1 to 28.864 of formula (Ib), where A is vinyloxycarbonyl and R 1 , R 3 and R 6 is as defined in Table M.

[0108] Table 29: This table discloses 864 compounds 29.1 to 29.864 of formula (Ib), where A is tert.butyloxycarbonyl and R 1 , R 3 and R 6 is as defined in Table M.

[0109] Table 30: This table discloses 864 compounds 30.1 to 30.864 of formula (Ib), where A is 4-fluoro-phenyl and R 1 , R 3 and R 6 is as defined in Table M.

[0110] Table 31: This table discloses 84 compounds 31.1 to 31.864 of formula (Ib), where A is 4-chloro-phenyl and R 1 , R 3 and R 6 is as defined in Table M.

[0111] Table 32: This table discloses 864 compounds 32.1 to 32.864 of formula (Ib), where A is 2,4-dichloro-phenyl and R 1 , R 3 and R 6 is as defined in Table M.

[0112] Table 33: This table discloses 864 compounds 33.1 to 33.864 of formula (Ib), where A is ethylsulfanylethyl and R 1 , R 3 and R 6 is as defined in Table M.

[0113] Table 34: This table discloses 864 compounds 34.1 to 34.864 of formula (Ib), where A is ethylsulfinylethyl and R 1 , R 3 and R 6 is as defined in Table M.

[0114] Table 35: This table discloses 864 compounds 35.1 to 35.864 of formula (Ib), where A is ethylsulfonylethyl and R 1 , R 3 and R 6is as defined in Table M.

[0115] Certain intermediate compounds of formula III, V, VI are also available, some of which are novel.

[0116] Thus, the following is made available herein: Compound of Formula III-a [ka] (where R 1 , R 3 and R 6 is defined for each row of table M, and R 4 is hydrogen, or R 1 , R 3 and R 6 is defined for each row of table M, and R 4 is cyano); Va compounds [ka] (where R 1 , R 3 and R 6 is defined for each row of table M, and R 4 is hydrogen, or R 1 , R 3 and R 6 is defined for each row of table M, and R 4 is cyano); Compound VI-a [ka] (where R 1 , R 3 and R 6 is defined for each row of table M, and R 4 is hydrogen and R 12 is selected from methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl and tert-butyl, or R 1 , R 3 and R 6 is defined for each row of table M, and R4 is cyano and R 12 is selected from methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl; Compound of Formula IV-aa [ka] (wherein X and Y are as defined in any one of Tables 1 to 20); and Compound of formula IV-ba [ka] (where A is as defined in any one of Tables 21 to 35).

[0117] In a further aspect, the present invention therefore makes available compounds of formula III, V and VI, wherein in each case R 1 , R 2 , R 3 , R 4 and R 5 is as defined for formula I in the first aspect, and R 12 is C1-C6 alkyl for Formula VI. Furthermore, R 1 , R 2 , R 3 , R 4 and R 5 The corresponding embodiments for also apply to compounds of formulae III, V and VI. 12 is, for formula VI, preferably methyl, ethyl, or propyl; more preferably methyl.

[0118] The compounds of formula (I) according to the present invention are preventively and / or therapeutically useful active ingredients in the field of pest control, even at low application rates, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded animal species, fish, and plants.The active ingredients according to the present invention act not only against normally susceptible animal pests, such as insects or representatives of the order Acarina, but also against all or individual developmental stages of resistant animal pests.The insecticidal or acaricidal activity of the active ingredients according to the present invention can be manifested directly, i.e., immediately or only after some time has passed, as destruction of pests, for example, during molting, or indirectly, for example, as reduced egg production and / or hatching rate.

[0119] Examples of the above animal pests are: From the order Acarina, for example: Acalitus spp., Aculus spp., Acaricalus spp., Aceria spp., Acarus siro, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia spp., Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides spp., Eotetranychus spp. spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Olygonychus spp., Ornithodoros spp., Polyphagotarsone latus, Panonychus spp., Phyllocoptruta oleivora, Phytonemus spp., Polyphagotarsonemus spp., Psoroptes spp., Rhipicephalus spp.), Rhizoglyphus spp., Sarcoptes spp., Steneotarsonemus spp., Tarsonemus spp. and Tetranychus spp.; From the order Anoplura, for example: Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; From the order Coleoptera, for example: Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp.), Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa ​​decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera castanea, Megascelis spp. spp., Melighetes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp., Phlyctinus spp., Popillia spp.), Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabaeidae, Sitophilus spp., Sitotroga spp., Somaticus spp., Sphenophorus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.;. From the order Diptera, for example: Aedes spp., Anopheles spp., Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp., Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp., Drosophila melanogaster, Fannia spp. spp.), Gastrophilus spp., Geomyza tripunctata, Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp. spp.), Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; From the order Hemiptera, for example: Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Aleurodes spp., Amblypelta nitida, Bathycoelia thalassina, Blissus spp., Cimex spp., Clavigrella tomentosicollis, Creontiades spp., Distantiella theobroma, Dichelops furcatus, Dysdercus spp., Edessa spp., Euchistus spp., Eurydema pulchrum, Eurygaster spp., Halyomorpha halys, Horcias nobilellus, Leptocorisa spp., Lygus spp., Margarodes spp., Murgantia histrionic, Neomegalotomus spp., Nesidiocoris tenuis, Nezara spp., Nysius simulans, Oebalus insularis insularis, Piesma spp., Piezodorus spp., Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophara spp.), Thyanta spp., Triatoma spp., Vatiga illudens;. Acyrthosium pisum, Adalges spp., Agalliana ensigera, Agonoscena targionii, Aleurodicus spp., Aleurocanthus spp., Aleurolobus barodensis, Aleurothrixus floccosus, Aleyrodes brassicae, Amarasca biguttula, Amritodus atkinsoni, Aonidiella spp. spp.), Aphididae, Aphis spp., Aspidiotus spp., Aulacorthum solani, Bactericera cockerelli, Bemisia spp., Brachycaudus spp., Brevicoryne brassicae, Cacopsylla spp., Cavariella aegopodii Scop., Ceroplaster spp.), Chrysomphalus aonidium, Chrysomphalus dictyospermi, Cicadella spp., Cofana spectra, Cryptomyzus spp., Cicadulina spp., Coccus hesperidum, Dalbulus maidis, Dialeurodes spp., Diaphorina citri, Diuraphis noxia, Dysaphis spp., Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp., Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp., Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp.), Neotoxoptera spp., Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Bayberry whitefly (Parabemisia myricae), Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Corn planthopper (Peregrinus maidis), Perkinsiella spp., Hop wart aphid (Phorodon humuli, Phylloxera spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp. spp.), Schizaphis spp., Sitobion spp.), Sogatella furcifera, Spisstilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp., Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris; From the order Hymenoptera, for example: Acromyrmex ants, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis ants, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta, Solenopsis spp. and Vespa spp.; From the order Isoptera, for example: Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis geminate From the order Lepidoptera, for example: Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp., Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp.), Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., Epinotia spp., Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp. spp.), Hellula undalis, Herpetogramma spp., Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp., Noctua spp., Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp.), pine sawyer moth (Panolis flammea), Papaipema nebris, pink bollworm (Pectinophora gossypiela), coffee leafminer (Perileucoptera coffeella), Pseudaletia unipuncta, potato tuber moth (Phthorimaea operculella), cabbage white butterfly (Pieris rapae), Pieris spp., diamondback moth (Plutella xylostella), Prays spp., Pseudoplusia spp., Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp.), Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta and Yponomeuta spp.;. From the order Mallophaga, for example: Damalinea spp. and Trichodectes spp.; From the order Orthoptera, for example: Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp. and Schistocerca spp.; From the order Psocoptera, for example: Liposcelis spp.; From the order Siphonaptera, for example: Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; From the order Thysanoptera, for example: Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.; From the order Thysanura, for example, Lepisma saccharina.

[0120] In a further aspect, the present invention also relates to plant parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular the root-knot nematode Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species; cyst-forming nematodes Globodera rostochiensis and other Globodera species; wheat cyst nematode Heterodera avenae, soybean cyst nematode Heterodera glycines, sugar beet cyst nematode Heterodera schachtii, clover cyst nematode Heterodera trifolii and other cyst nematodes (Heterodera species); seed gall nematodes, Anguina species; stem and peel nematodes, Aphelenchoides species; sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; pine wood nematode, Bursaphelenchus xylophilus and other Bursaphelenchus species; ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; fire nematodes, Dolichodorus species;Screw nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Spear nematodes, Hoploaimus species; False root-knot nematodes, Nacobbus species; Tylenchidae, Longidorus elongatus elongatus and other Longidorus species; pin nematodes, Pratylenchus species; root-lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; root-lesion nematodes, Radopholus similis and other Radopholus species; false nematodes, Rotylenchus robustus, Rotylenchus reniformis and other Rotylenchus species; Scutellonema species; Trichodorus primitivus and other Trichodorus species, Paratrichodorus species;plant-parasitic nematodes such as the claytonid nematode, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; the burrowing nematode, Tylenchulus species; plant-parasitic nematodes such as the giant sting nematode, Xiphinema species; and plant-parasitic nematodes such as Subanguina species, Hypsoperine species, Macroposthonia species, Melinius species, Punctodera species and Quinisulcius species. The present invention may also relate to a method for preventing damage to plants and parts thereof by other plant-parasitic nematode species, such as Pseudomonas spp.;

[0121] The compounds of the present invention may also have activity against mollusks, such as, for example, species of the family Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. rufus); Nemoralis); Ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae (Helicigona albustrum) arbustorum); Helicodiscus; Helix (H. aperta); Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Monoa These include the genera Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0122] The active ingredients according to the invention can be used to control, i.e. suppress or destroy, pests of the above-mentioned types occurring in particular on plants, in particular on useful plants and ornamental plants in agriculture, horticulture and forestry, or on organs such as the fruits, flowers, leaves, stems, tubers or roots of such plants, in some cases even plant organs formed at a later time remaining protected from these pests.

[0123] Suitable target crops are, in particular, cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beets such as sugar beet or fodder beet; fruits, such as pome fruits, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries or blackberries; legumes, such as beans, lentils, peas or soybeans; rapeseed, mustard, poppy, olive, sunflower, palm, castor, cocoa or groundnut. citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes or peppers; plants of the Lauraceae family such as avocado, cinnamon or camphor; and also tobacco, tree nuts, coffee, eggplant, sugarcane, tea, pepper, grapes, hops, plantains and latex plants.

[0124] In certain embodiments, the compounds of formula (I) control mites, rust mites, and spider mites on crops, trees, and plants selected from vegetables (especially tomatoes and cucurbits), citrus fruits, pome fruits, stone fruits, nuts, cotton, tropical crops, avocados, ornamentals, beans, soybeans, strawberries, and grapes.

[0125] The compositions and / or methods of the present invention may be used on any ornamental and / or vegetable crop, including flowers, shrubs, broadleaf trees and evergreen trees.

[0126] For example, the present invention relates to the use of the following ornamental species: Ageratum spp., Alonsoa spp., Anemone spp., Anisodontea capsenisis, Anthemis spp., Antirrhinum spp., Aster spp., Begonia spp. (e.g., B. elatior, B. semperflorens, B. tubereux), Bougainvillea spp., Brachycome spp. spp.), Brassica spp. (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Bleeding hearts spectabilis, Dorotheantus spp., Lisianthus (Eustoma grandiflorum), Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Globetrotter (Gomphrena globosa), Heliotropium spp., Helianthus spp., Hibiscus spp.), Hortensia spp., Hydrangea spp., Hypoestes phyllostachya, Impatiens spp. (I. Walleriana), Iresines spp., Kalanchoe spp., Lantana camara, Lavatera trimestris, Leonotis leonurus, Lilium spp., Mesembryanthemum spp., Mimulus spp., Monarda spp. spp.), Nemesia spp., Tagetes spp., Dianthus spp. (carnations), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (ivy geranium (P. peltatum), P. Zonale), Viola spp. (pansies), Petunia spp., Phlox spp., Plecthranthus spp., Poinsettia spp. spp.), Parthenocissus spp. (American Creeper (P. quinquefolia), Ivy (P. tricuspidata)), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (roses), Rudbeckia spp., Saintpaulia spp., Salvia spp.), Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp., and other bedding plants.

[0127] For example, the present invention relates to the use of the following vegetable species: Allium spp. (garlic (A. sativum), onion (A. cepa), shallot (A. oschaninii), leek (A. porrum), scallion (A. ascalonicum), green onion (A. fistulosum)), chervil (Anthriscus cerefolium), celery (Apium graveolus), asparagus (Asparagus officinalis), beet (Beta vulgarus), Brassica spp. (B. oleracea, Chinese cabbage (B. pekinensis), turnip (B. rapa)), chili pepper (Capsicum annuum), chickpea (Cicer arietinum), endive (Cichorium endivia), Cichorum spp. spp.) (chicory (C. intybus), endive (C. endivia)), watermelon (Citrillus lanatus), Cucumis spp. (saffron (C. sativus), melon (C. melo)), Cucurbita spp. (Cucurbita pepo, Cucurbita maxima), Cyanara spp. (artichoke (C. scolymus), cardoon (C. cardunculus)), carrot (Daucus carota), fennel (Foeniculum vulgare), Hypericum spp., lettuce (Lactuca sativa), tomato spp. spp.) (tomato (L. esculentum), tomato (L. lycopersicum)), mint species (Mentha spp.), basil (Ocimum basilicum), parsley (Petroselinum crispum), Phaseolus species (Phaseolus spp.) (P. vulgaris, runner bean (P.The present invention may be used in any of the following plants: pea (Pisum sativum), radish (Raphanus sativus), rhubarb (Rheum rhaponticum), rosemary (Rosemarinus spp.), salvia (Salvia spp.), yellow rosemary (Scorzonera hispanica), eggplant (Solanum melongena), spinach (Spinacea oleracea), Valerianella spp. (V. locusta, V. eriocarpa), and broad bean (Vicia faba).

[0128] Preferred ornamental species include Saintpaulia, Begonia, Dahlia, Gerbera, Hydrangea, Vervain, Rosa, Kalanchoe, Poinsettia, Aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hydrangea, Rosemary, Sage, St. John's Wort, Mint, Bell Pepper, Tomato, and Cucumber.

[0129] The active ingredients according to the invention are particularly suitable for controlling Aphis craccivora, Diabrotica balteata, Heliothis virescens, Myzus persicae, Plutella xylostella and Spodoptera littoralis in cotton, vegetables, corn, rice and soybean crops. The active ingredients according to the invention are particularly suitable for controlling Mamestra (preferably on vegetables), codling moth (Cydia pomonella) (preferably on apple), Empoasca (preferably on vegetables and vineyards), Leptinotarsa ​​(preferably on potato) and Chilo supressalis (preferably on rice).

[0130] The compounds of formula (I) are effective against mites, spider mites and rust mites, for example Acarapis spp; Acarapis woodi; Acarus siro; Acarus spp; Aceria sheldoni; Aculops pelekassi; Aculops spp; Aculus schlechtendali; Aculus spp; Amblyseius fallacis; Brevipalpus spp; Brevipalpus phoenicis; Bryobia praetiosa; Bryobia rubrioculus; Caloglyphus spp); Cheyletiella blakei; Cheyletiella spp; Cheyletiella yasguri; Chorioptes bovis; Chorioptes spp; Cytodites spp; Demodex bovis; Demodex caballi; Demodex canis; Demodex caprae; Demodex equi; Demodex ovis; Demodex spp; Demodex suis; Dermonychus gallinae; Dermonychus spp; Eotetranychus spp); Willamette spider mite (Eotetranychus willamettei); Pear rust mite (Epitrimerus pyri); Eriophyes ribis; Eriophyes spp; Grape leafminer mite (Eriophyes vitis);Eutetranychus spp; Halotydeus destructor; Hemitarsonemus spp; Knemidocoptes spp; Laminosioptes spp; Listrophorus spp; Myobia spp; Neoschongastia xerothermobia; Neotrombicula autumnalis; Neotrombicula desaleri; Notoedres cati; Notoedres spp; Oligonychus coffeae; Oligonychus ilicis; Oligonychus spp; Ornithocheyletia spp; Ornithonyssus bursa; Ornithonyssus spp; Ornithonyssus sylviarum; Otodectes cynotis; Otodectes spp; Panonychus citri; Panonychus spp; Panonychus ulmi; Phyllocoptruta oleivora; Phyllocoptruta spp.; Phytoseiulus spp.; Pneumonyssoides caninum; Polyphagotarsonemus latus); Polyphagotarsonemus spp; Psorergates ovis; Psorergates spp; Psoroptes cuniculi;Psoroptes equi, Psoroptes ovis, Psoroptes spp., Pterolichus spp., Raillietia spp., Rhizoglyphus spp., Sarcoptes bovis, Sarcoptes canis, Sarcoptes caprae, Sarcoptes equi, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes spp., Sarcoptes spp. suis; Steneotarsonemus spinki; Steneotarsonemus spp; Sternostoma spp; Tarsonemus spp; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp; Tetranychus urticae; Trombicula akamushi; Trombicula spp; Typhlodromus occidentalis; Tyrophagus spp; Varroa jacobsoni; Varroa spp spp); Vasates lycopersici; and Zetzellia mali.

[0131] In one embodiment, the compound of formula (I) is effective against Aceria sheldoni; Aculus lycopersici; Aculus pelekassi; Aculus schlechtendali; Brevipalpus phoenicis; Brevipalpus spp.; Bryobia rubrioculus; Eotetranychus carpini; Eotetranychus spp.; Epitrimerus pyri; Eriophyes piri; Eriophyes spp.; Eriophyes vitis; Eutetranychus africanus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus citri; Panonychus ulmi; Phyllocoptes vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp.; and Tetranychus urticae.

[0132] In a further embodiment, the compound of formula (I) is effective against Aceria sheldoni; Aculus pelekassi; Brevipalpus phoenicis; Brevipalpus spp.; Eriophyes piri; Eriophyes vitis; Eutetranychus africanus; Eutetranychus orientalis; Oligonychus pratensis; Panonychus ulmi; Phyllocoptes vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus); Tetranychus kanzawai; Tetranychus spp.; and Tetranychus urticae.

[0133] The term "crop plant" should also be understood to include crop plants that have been transformed by the use of recombinant DNA techniques so as to be capable of synthesizing one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0134] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins from Bacillus thuringiensis or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A; or bacterial-colonizing nematodes, such as Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc. insecticidal proteins of Azotoxins; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and neurotoxins specific to other insects; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin and papain inhibitors; ricin, corn-RIP, abrin, rufin, saporin ribosome-inactivating proteins (RIPs) such as erythrin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as blockers of sodium channels or calcium channels, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0135] In the context of the present invention, delta-endotoxins are understood to mean, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3, or Vip3A, and also specifically hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the native toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0136] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0137] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI type and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0138] The toxins contained in the transgenic plants confer resistance to pests found in a range of insect taxa, but are particularly common in beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0139] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants include YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) for tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0140] Further examples of such transgenic crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through the transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also genetically expresses the enzyme PAT to confer tolerance to the herbicide glufosinate ammonium.

[0141] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the Cry1Ab toxin. Bt176 maize also genetically expresses the enzyme PAT to confer tolerance to the herbicide glufosinate ammonium.

[0142] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS (Chemin de l'Hobit 27, F-31 790 St. Sauveur, France). This maize has been made insect-resistant by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055, modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0143] 4. MON 863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium). MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects.

[0144] 5. IPC 531 cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium).

[0145] 6. 1507 Maize, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Genetically modified maize for expression of the protein Cry1F for resistance to certain Lepidoptera insects and the protein PAT for resistance to the herbicide glufosinate ammonium.

[0146] 7. NK603 x MON 810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium). This maize consists of a conventionally bred hybrid maize variety by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 maize also genetically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin, obtained from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0147] Transgenic crops of insect-resistant plants are also described in the BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http: / / bats.ch).

[0148] The term "crop plant" should also be understood to include crop plants that have been transformed by the use of recombinant DNA technology so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "pathogenicity-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0149] Crops can also be improved to increase resistance to fungal (e.g., Fusarium, anthracnose, or Phytophthora), bacterial (e.g., Pseudomonas), or viral (e.g., potato leaf curl virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

[0150] Crops also include those that have a high resistance to nematodes, such as the soybean cyst nematode.

[0151] Crops that are tolerant to abiotic stress include those that have increased tolerance to drought, high salinity, high temperature, low temperature, frost, or light due to, for example, expression of NF-YB or other proteins known in the art.

[0152] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium or calcium channels, e.g., viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; so-called "pathogenesis-related proteins" (PRPs; see, for example, EP 0 392 225); antipathogenic substances produced by microorganisms, such as peptide or heterocyclic antibiotics (see, for example, WO 95 / 33818) or proteins or polypeptide factors involved in plant pathogen defense (the so-called "plant disease resistance genes" described in WO 03 / 000906).

[0153] Further fields of use of the compositions according to the invention are the protection of stored goods and storage rooms and of raw materials (such as wood and textiles), floor coverings and buildings, and in the hygiene sector, in particular the protection of humans, domestic animals and productive livestock from pests of the above-mentioned types.

[0154] The present invention provides compounds of the first aspect for use in therapy. The present invention provides compounds of the first aspect for use in controlling parasites in or on animals. The present invention further provides compounds of the first aspect for use in controlling ectoparasites on animals. The present invention further provides compounds of the first aspect for use in the prevention and / or treatment of diseases transmitted by ectoparasites.

[0155] The present invention provides the use of a compound of the first aspect for the manufacture of a medicament for controlling parasites in or on an animal. The present invention further provides the use of a compound of the first aspect for the manufacture of a medicament for controlling ectoparasites on an animal. The present invention further provides the use of a compound of the first aspect for the manufacture of a medicament for preventing and / or treating diseases transmitted by ectoparasites.

[0156] The present invention provides the use of a compound of the first aspect in the control of parasites in or on an animal. The present invention further provides the use of a compound of the first aspect in the control of ectoparasites on an animal.

[0157] The term "controlling" when used in relation to parasites in or on animals refers to the reduction of pest or parasite numbers, the eradication of pests or parasites and / or the prevention of further pest or parasite infestation.

[0158] The term "treating" when used in reference to parasites in or on an animal refers to suppressing, slowing, arresting or reversing the progression or severity of an existing condition or disease.

[0159] When used in reference to parasites in or on an animal, the term "prevent" refers to the avoidance of symptoms or disease developing in the animal.

[0160] When used in reference to parasites in or on animals, the term "animal" can refer to mammals and non-mammals such as birds or fish. In the case of mammals, this can be a human or non-human mammal. Non-human mammals include, but are not limited to, livestock animals and companion animals. Livestock animals include, but are not limited to, cattle, camelids, pigs, sheep, goats, and horses. Companion animals include, but are not limited to, dogs, cats, and rabbits.

[0161] A "parasite" is a pest that lives in or on a host animal and benefits from nutrients provided at the expense of the host animal. An "endoparasite" is a parasite that lives inside the body of a host animal. An "ectoparasite" is a parasite that lives on a host animal. Ectoparasites include, but are not limited to, mites, insects, and crustaceans (e.g., sea lice). The subclass Acari (or Acarina) includes ticks and mites. Ticks include, but are not limited to, members of the following genera: Rhipicaphalus, such as Rhipicaphalus (Boophilus) microplus and Rhipicephalus sanguineus; Amblyomma; Dermacentor; Haemaphysalis; Hyalomma; Ixodes; Rhipicentor; Margaropus; Argas; Otobius; and Ornithodoros. Mites include, but are not limited to, members of the following genera: Chorioptes, such as Chorioptes bovis; Psoroptes, such as Psoroptes ovis; Cheyletiella; Dermanyssus, such as Dermanyssus gallinae; Ortnithonyssus; Demodex, such as Demodex canis; Sarcoptes, such as Sarcoptes scabiei; and Psorergates.Insects include, but are not limited to, members of the following orders: Siphonaptera, Diptera, Chelonia, Lepidoptera, Coleoptera, and Homoptera. Members of the Siphonaptera order include, but are not limited to, the cat flea (Ctenocephalides felis) and the dog flea (Ctenocephatides canis). Members of the order Diptera include, but are not limited to, Musca species; bot flies, such as Gasterophilus intestinalis and Oestrus ovis; stable flies; horse flies, such as Haematopota species and Tabunus species; haematobia, such as Haematobia irritans; Stomoxys; Lucilia; midges; and mosquitoes. Members of the order Chestnuti include, but are not limited to, sucking and biting lice, such as Bovicola ovis and Bovicola bovis.

[0162] When used in connection with parasites in or on animals, the term "effective amount" refers to the amount or dosage of a compound of the present invention or a salt thereof that, upon administration to the animal in one or more doses, produces the desired effect in or on the animal. An effective amount can be readily determined by the attending diagnostician, as one skilled in the art, by using known techniques and observing results obtained under analogous circumstances. In determining an effective amount, the attending diagnostician will take into account numerous factors, including, but not limited to, the species of mammal; its size, age, and general health; the parasite and level of infestation to be controlled; the particular disease or disorder involved; the extent or complications or severity of the disease or disorder; the individual's response; the particular compound administered; the mode of administration; the bioavailability characteristics of the administered preparation; the selected dosage regimen; the use of concomitant medications; and other relevant circumstances.

[0163] The compounds of the present invention can be administered to animals by any route that has the desired effect, including, but not limited to, topical, oral, parenteral, and subcutaneous administration. Topical administration is preferred. Formulations suitable for topical administration include, for example, solutions, emulsions, and suspensions, and can be in the form of pour-ons, spots, spray-ons, spray-laces, or dips. Alternatively, the compounds of the present invention can be administered by ear tag or collar.

[0164] Salt forms of the compounds of the present invention include both pharmaceutically and veterinarily acceptable salts, which may differ from agrochemically acceptable salts. Pharmaceutically and veterinarily acceptable salts and the general methodology for preparing them are well known in the art. See, for example, Gould, PL, "Salt selection for basic drugs," International Journal of Pharmaceutics, 33:201-217 (1986); Bastin, RJ, et al., "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities," Organic Process Research and Development, 4:427-435 (2000); and Berge, SM, et al., "Pharmaceutical Salts," Journal of Pharmaceutical Sciences, 66:1-19 (1977). Those skilled in the art of synthesis will understand that the compounds of the present invention can be easily converted to salts such as hydrochlorides and isolated as such salts using techniques and conditions well known to those skilled in the art. Additionally, those skilled in the art of synthesis will recognize that compounds of the present invention can be readily converted from a corresponding salt to the corresponding free base, and isolated as such a salt.

[0165] The present invention also provides methods for controlling pests (such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests comprises applying a composition of the present invention to the target pest, its habitat, or a surface or substrate by brushing, rolling, spraying, painting, or dipping. By way of example, IRS (indoor residual spray) application of surfaces such as walls, ceilings, or floors is contemplated by the method of the present invention. In another embodiment, it is contemplated to apply such compositions to substrates such as nonwoven or woven materials in the form of (or in a form that can be used to manufacture) netting, clothing, bedding, curtains, and tents.

[0166] In one embodiment, a method for controlling such pests comprises applying a pesticidally effective amount of a composition of the present invention to a target pest, its habitat, or a surface or substrate to provide effective, residual pest control activity to the surface or substrate. Such application may be by brushing, rolling, spraying, painting, or dipping the pesticidal composition of the present invention. For example, IRS application to surfaces such as walls, ceilings, or floors is contemplated by the method of the present invention to provide effective, residual pest control activity to the surface. In another embodiment, the application of such compositions for residual pest control on substrates such as fabric materials in the form of (or in the form that can be used to manufacture) netting, clothing, bedding, curtains, and tents is contemplated.

[0167] The substrates to be treated, including nonwovens, fabrics, or nets, can be made of natural fibers such as cotton, raffia, jute, flax, sisal, hemp, or wool, or synthetic fibers such as polyamide, polyester, polypropylene, or polyacrylonitrile. Polyesters are particularly suitable. Methods for treating textiles are known, for example, from WO 2008 / 151984, WO 2003 / 034823, U.S. Pat. No. 5,631,072, WO 2005 / 64072, WO 2006 / 128870, EP 1 724 392, WO 2005 113 886, or WO 2007 / 090739.

[0168] A further field of use for the compositions according to the invention is that of trunk injection / trunk treatment of all ornamental trees and all kinds of fruit and nut-bearing trees.

[0169] In the field of trunk injection / trunk treatment, the compounds according to the invention are particularly suitable against wood-boring insects of the above-mentioned orders Lepidoptera and Coleoptera, in particular the woodborers listed in Tables A and B below.

[0170] [Table 2]

[0171] [Table 3-1] [Table 3-2]

[0172] The present invention may be used to control any insect pest that may be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, pill bugs, mites, mole crickets, scale insects, mealybugs, mites, boxworms, southern chinch bugs, and grubs. The present invention may also be used to control insect pests in various stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0173] In particular, the present invention relates to the treatment of grubs (Cyclocephala spp. (e.g., masked chafer, C. lurida), Rhizotrogus spp. (e.g., European chafer, R. majalis), Cotinus spp. (e.g., blue swallowtail, C. nitida), Popillia spp. (e.g., Japanese beetle, P. japonica), Phyllophaga spp. (e.g., May / June beetle), Ataenius spp., and the like). spp. (e.g., Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., red-veined scarab beetle, M. castanea) and Tomarus spp.), cotton bollworms (Margarodes spp.), mole crickets (tawny, southern and brachypterous; Scapteriscus spp., Gryllotalpa africana) and leatherjackets (European crane fly, Tipula The compounds may be used to control insect pests that feed on the roots of turfgrass, including Pseudomonas spp.

[0174] The present invention may also be used to control straw-dwelling insect pests of turfgrass, including cutworms (such as Spodoptera frugiperda and the common armyworm (Pseudaletia unipuncta)), cutworms, weevils (such as Sphenophorus spp., S. venatus verstitus, and S. parvulus) and sod webworms (such as Crambus spp. and the tropical sod webworm, Herpetogramma phaeopteralis).

[0175] The present invention may also be used to control insect pests that live on the ground and feed on turfgrass leaves, including the lesser stink bug (such as the southern kinkbag, Blissus insularis), bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae), and greengrass aphids.

[0176] The present invention may also be used to control other pests of turfgrass, such as the red fire ant (Solenopsis invicta), which creates ant mounds in turfgrass.

[0177] In the hygiene field, the compositions according to the invention are effective against ectoparasites such as hard ticks, soft ticks, scabies mites, chiggers, flies (stable flies and licking flies), parasitic fly larvae, lice, pubic lice, biting lice and fleas.

[0178] Examples of such parasites are: Among the Anoplurida, the genera Haematopinus, Linognathus, Pediculus, Phtirus, and Solenopotes are included.

[0179] From the order Mallophagida, the genera Trimenopon, Menopon, Trinoton, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes and Felicola.

[0180] Among the order Diptera and its suborders Nematocerina and Brachycerina, for example, the genera Aedes, Anopheles, Culex, Simulium, Eusimulium, Phlebotomus, Lutzomyia, Culicoides, Chrysops, Hybomitra, Atylotus, Tabanus, 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.), sheep flies (Oestrus spp.), cow flies (Hypoderma spp.), bot flies (Gasterophilus spp.), hood flies (Hippobosca spp.), deer flies (Lipoptena spp.) and sheep hood flies (Melophagus spp.).

[0181] Among the Siphonapterida, for example, the human flea genus (Pulex spp.), the dog flea genus (Ctenocephalides spp.), the mouse flea genus (Xenopsylla spp.), and the long flea genus (Ceratophyllus spp.).

[0182] From the order Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., and Panstrongylus spp.

[0183] From the order Blattaria, for example, the Asian cockroach (Blatta orientalis), the American cockroach (Periplaneta americana), the German cockroach (Blattela germanica) and the genus Supella.

[0184] Among the subclass Acaria (Acarida) and the suborder Metastigmata and Mesostigmata, for example, the genera Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp. spp.), Pneumonyssus spp., Sternostoma spp. and Varroa spp.

[0185] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, the genera Acarapis, Cheyletiella, Ornithocheyletia, Myobia, Psorergates, Demodex, Trombicula, Listrophorus, Acarus, Tyrophagus, Caloglyphus, Hypodectes spp.), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0186] The compositions according to the invention are also suitable for protecting against insect infestation in materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cardboard, leather, floor coverings and building materials.

[0187] The compositions according to the invention can be used, for example, against the following pests: European house borer (Hylotrupes bajulus), Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, pine wood beetle (Ernobius mollis), longhorn beetle (Priobium carpini), flat-headed beetle (Lyctus brunneus), African flat-headed beetle (Lyctus africanus), American flat-headed beetle (Lyctus planicollis), oak flat-headed beetle (Lyctus beetles such as Xyleborus species, Tryptodendron species, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon species and Dinoderus minutus, as well as beetles such as Sirex juvencus, Urocerus gigas, Urocerus gigas hymenopteran insects such as Urocerus taignus and Urocerus augur;Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, and Coptotermes formosanus, as well as wood silverfish such as Lepisma saccharina. The compounds of formula I and I'a or salts thereof are particularly suitable for controlling one or more pests selected from the families: Noctuidae, Plutellidae, Chrysomelidae, Thripidae, Pentatomidae, Tortricidae, Delphacidae, Aphididae, Noctuidae, Crambidae, Meloidogynidae and Heteroderidae. In a preferred embodiment of each aspect, the compound TX (wherein the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8") controls one or more pests selected from the families: Noctuidae, Plutellidae, Chrysomelidae, Thripidae, Pentatomidae, Tortricidae, Delphacidae, Aphididae, Noctuidae, Crambidae, Meloidogynidae, and Heteroderidae;

[0188] The compounds of formula I and I'a or salts thereof are effective against pests of the genera Spodoptera spp., Plutella spp., Frankliniella spp., Thrips spp., Euschistus spp., Cydia spp., Nilaparvata spp., Myzus spp., Aphis spp., Diabrotica spp., Rhopalosiphum spp., Pseudoplusia spp. and Chilo spp. spp. In a preferred embodiment of each aspect, the compound TX (wherein the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8") is selected from the genera: Spodoptera spp., Plutella spp., Frankliniella spp., Thrips spp., Euschistus spp., Cydia spp., Nilaparvata spp., Myzus spp., Aphis spp., Diabrotica spp., Rhopalosiphum spp., Pseudoplusia spp. The compound controls one or more pests selected from Chilo spp. and Chilo spp.

[0189] The compounds of formula I and I'a or salts thereof are particularly suitable for controlling one or more of Spodoptera littoralis, diamondback moth (Plutella xylostella), western flower thrips (Frankliniella occidentalis), onion thrips (Thrips tabaci), Euschistus heros, codling moth (Cydia pomonella), brown planthopper (Nilaparvata lugens), green peach aphid (Myzus persicae), Chrysodeixis includens, bean aphid (Aphis craccivora), Diabrotica balteata, Rhopalosiphum padi and rice stem borer (Chilo suppressalis).

[0190] In a preferred embodiment of each aspect, compound TX (wherein the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8") is effective against Spodoptera littoralis, diamondback moth (Plutella xylostella), western flower thrips (Frankliniella occidentalis), onion thrips (Thrips tabaci), Euschistus heros, codling moth (Cydia pomonella), brown planthopper (Nilaparvata lugens), green peach aphid (Myzus persicae), Chrysodeixis includens, bean aphid (Aphis craccivora), Diabrotica balteata, Rhopalosiphum padiata, Padia and the Egyptian armyworm (Spodoptera littoralis) + TX, diamondback moth (Plutella xylostella) + TX, and other rice stem borers (Chilo Suppressalis) such as; western flower thrips (Frankliniella occidentalis) + TX, onion thrips (Thrips tabaci) + TX, Euschistus heros + TX, codling moth (Cydia pomonella) + TX, brown planthopper (Nilaparvata lugens) + TX, green peach aphid (Myzus persicae) + TX, Chrysodeixis includens + TX, bean aphid (Aphis craccivora) + TX, Diabrotica balteata + TX, Rhopalosiphum Padi) + TX and rice stem borer (Chilo suppressalis) + TX.

[0191] In one embodiment of each aspect, one compound from Tables 1-35 and Tables P1-P8 is used to control Spodoptera littoralis, Plutella xylostella, Frankliniella occidentalis, Thrips tabaci, Euschistus heros, Cydia pomonella, Nilaparvata lugens, Myzus persicae, Chrysodeixis includens, Aphis craccivora, Diabrotica balteata, Rhopalosiphum padiata, Rhopalosiphum nigricans, Rhopalosiphum padiata ... Padia) and rice stem borer (Chilo suppressalis).

[0192] In one embodiment one compound from Tables 1 to 35 and Tables P1 to P8 is suitable for controlling Mamestra (preferably in vegetables), codling moth (Cydia pomonella) (preferably in apple), Empoasca (preferably in vegetables, vineyards), Leptinotarsa ​​(preferably in potato) and Chilo supressalis (preferably in rice).

[0193] The compounds of the present invention may have any number of benefits, including, inter alia, advantageous levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile (e.g., improved physicochemical properties or high biodegradability against above- and below-ground non-target organisms such as fish, birds and bees)). In particular, it has surprisingly been found that certain compounds of formula (I) may exhibit advantageous safety profiles, especially against non-target arthropods, such as pollinators such as honeybees, solitary bees and bumblebees, most particularly the European honeybee (Apis mellifera).

[0194] Although the compounds of the present invention can be used as pesticides in their native form, they are generally formulated into compositions using formulation aids such as carriers, solvents, and surfactants in various ways. The formulations can be in various physical forms, such as dustable powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil-based flowables, aqueous dispersions, oil-based dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or a water-miscible organic solvent as a carrier), impregnated polymer films, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, trace elements, biological materials, oils, or solvents.

[0195] The formulations can be prepared by mixing the active ingredient with formulation aids to obtain a composition in the form of, for example, finely divided solids, granules, solutions, dispersions, or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oil, vegetable or animal oil, modified vegetable or animal oil, organic solvent, water, surfactant, or combinations thereof.

[0196] The active ingredient can also be contained in extremely fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules typically have diameters of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule. The active ingredient can be in the form of a bulk solid, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulating membrane can comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers, and starch xanthate, or other polymers known to those skilled in the art. Alternatively, extremely fine microcapsules can be formed containing the active ingredient in the form of fine particles in a base solid matrix, but the microcapsules themselves are not encapsulated.

[0197] The formulation auxiliaries suitable for preparing the compositions according to the invention are known per se. Liquid carriers include water, toluene, xylene, petroleum ether, 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 abietic acid, 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, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate Examples of suitable solvents include ethanol, 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, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone.

[0198] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kiesl lager, limestone, calcium carbonate, bentonite, calcium montmorillonite, cotton hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar materials.

[0199] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially in formulations that can be diluted with a carrier before use. The surface-active substances can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifying agents, 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 adducts such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts such as tridecyl alcohol ethoxylate; soaps such as sodium stearate; salts of alkylnaphthalenesulfonates such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinates 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-alkyl phosphate esters; and further substances described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).

[0200] Additional adjuvants that may be used in the pest control formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting and buffering agents, corrosion inhibitors, fragrances, wetting agents, uptake enhancers, trace elements, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0201] The compositions of the present invention may contain additives including vegetable or animal oils, mineral oils, alkyl esters of such oils, or mixtures of such oils and oil derivatives. The amount of oil additive in the compositions of the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or vegetable oils such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils such as methyl derivatives, or animal oils such as fish oil or beef tallow. Preferred oil additives are C8 to C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids, including, 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 listed in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0202] The compositions of the present invention generally comprise 0.1 to 99% by weight, especially 0.1 to 95% by weight, of the compounds of the present invention and 1 to 99.9% by weight of formulation aids, which preferably include 0 to 25% by weight of surfactants. Although commercial products may preferably be formulated as concentrates, end users will typically utilize diluted formulations.

[0203] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing weather conditions and other factors which depend on the application method, e.g., the time of application and the target crop. As a general guideline, the compounds may be applied in amounts of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0204] A preferred formulation may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surface active agent: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0205] Powder: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0206] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surface active agent: 1 to 40%, preferably 2 to 30%

[0207] Wettable powder: 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%

[0208] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0209] The following examples further illustrate, but do not limit, the present invention.

[0210] [Table 4]

[0211] The complex is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder that can be diluted with water to obtain a suspension of the desired concentration.

[0212] [Table 5]

[0213] The complex is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly as a seed treatment.

[0214] [Table 6]

[0215] Emulsions of any required dilution that can be used for plant protection are available from this concentrate by dilution with water.

[0216] [Table 7]

[0217] Ready-to-use dusts are obtained by mixing the complex with a carrier and grinding the mixture in a suitable mill. Such powders can also be used as dry seed dressings.

[0218] [Table 8]

[0219] The compound is mixed and ground with the adjuvant, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0220] [Table 9]

[0221] In a mixer, the finely ground composite is applied uniformly to kaolin moistened with polyethylene glycol, resulting in coated, dust-free granules.

[0222] [Table 10]

[0223] The finely ground composite is thoroughly mixed with adjuvants to give a suspension concentrate which can be diluted with water to give a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring or dipping.

[0224] [Table 11]

[0225] The finely ground composite is thoroughly mixed with adjuvants to give a suspension concentrate which can be diluted with water to give a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring or dipping.

[0226] Slow-release capsule suspension 28 parts of the composite are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer, and 51.6 parts water until the desired particle size is achieved. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The diameter of the medium-sized capsules is 8 to 15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for this purpose.

[0227] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically preferred formulation in combination with agriculturally acceptable adjuvants. [Example]

[0228] Preparation example: LCMS method: Method 1: Spectra were recorded on a Waters ZQ mass spectrometer (single quadrupole mass spectrometer); instrument parameters: ionization method: electrospray polarity: positive (negative) ion; capillary (kV) 3.00, cone (V) 30.00, extractor (V) 2.00, gas temperature (°C) 350, drying gas flow (mL / min) 9.8, Neb press 45 psig, mass range: 90–1000 Da.

[0229] LC: Agilent HP 1100 HPLC: solvent degasser, quaternary pump (ZCQ) / binary pump (ZDQ), heated column compartment, and diode-array detector. Column: porpshell 120 C18, 2.7 μm particle size, 120 Å, 4.6 × 50 mm; temperature: 30 °C. DAD wavelength range (nm): 190–400. Solvent gradient: A = water + 0.1% HCOOH. B = acetonitrile + 0.08% HCOOH.

[0230] [Table 12]

[0231] Method 2: Spectra were recorded on a Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass range: 140-800 Da) and a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode-array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 2.5 min; Flow (ml / min): 0.75.

[0232] Method 3: Spectra were recorded on a Waters mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions, capillary: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150 °C, desolvation temperature: 350 °C, cone gas flow: 50 l / h, desolvation gas flow: 650 l / h, mass range: 100-900 Da) and a Waters Acquity UPLC: binary pump, heated column compartment, diode-array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–500; Solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; Gradient: 10–100% B in 1.2 min; Flow (ml / min): 0.85.

[0233] The following abbreviations are used in the experimental descriptions below: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, RT = retention time, min = minutes.

[0234] Example P1: 5-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile (compound P1.1): [ka] Step 1: Methyl 4-hydroxy-5-iodo-2-(trifluoromethyl)benzoate [ka] Methyl 4-hydroxy-2-(trifluoromethyl)benzoate (10.5 g, 47.7 mmol), iodine (18.0 g, 70.9 mmol), and potassium carbonate (13.2 g, 95.5 mmol) were added to THF (150 mL). The reaction mixture was heated at reflux for 16 hours. Sodium thiosulfate solution was then added. The mixture was extracted with ethyl acetate, and the organic phase was washed three times with brine. The solvent was evaporated, and the residue was purified by chromatography (petroleum ether:ethyl acetate=5:1) to give a white solid (6.90 g, 41.8%). The eluate in DMSO-d6 was eluted. 1 H-NMR[ppm]: 11.75(s,1H), 8.23(s,1H), 7.23(s,1H), 3.81(s,3H).LC-MS(Method 1): RT=4.34 min;[MH] - =344.9.

[0235] Step 2: Methyl 5-cyano-4-hydroxy-2-(trifluoromethyl)benzoate [ka] Methyl 4-hydroxy-5-iodo-2-methyl-benzoate (2.50 g, 8.56 mmol) and copper(I) cyanide (1.94 g, 21.7 mmol) were stirred in 1-methylpyrrolidin-2-one (20 mL) at 110 °C for 12 hours. The mixture was poured into water, extracted with ethyl acetate (50 mL), dried over NaSO, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (ethyl acetate / petroleum ether = 1 / 5) to give a white solid (1.30 g, 73.4%). 1 H-NMR[ppm]: 12.75(bs,1H), 8.23(s,1H), 7.40c(s,1H), 3.83(s,3H).LC-MS (Method 1): RT=3.88 min;[MH]-=244.

[0236] Step 3: Methyl 5-cyano-2-(trifluoromethyl)-4-(trifluoromethylsulfonyloxy)benzoate [ka] Methyl 5-cyano-4-hydroxy-2-(trifluoromethyl)benzoate (1.00 g, 4.08 mmol), dichloromethane (20 mL), and pyridine (0.968 g, 12.2 mmol) were added to a reaction vessel, the reaction mixture was cooled to 0 °C, and trifluoromethanesulfonic anhydride (2.88 g, 10.2 mmol) was added. The reaction mixture was warmed to room temperature, stirred at room temperature for 30 minutes, and cooled to 0 °C. Dichloromethane (30 mL) and water (50 mL) were added. The organic phase was collected, dried over Na2SO4, concentrated under reduced pressure, and subjected to silica gel chromatography purification (ethyl acetate / petroleum ether = 1:10) to give a colorless oil (1.38 g, 90.0%). DMSO-d6 1 H-NMR[ppm]:8.70(s,1H), 8.46(s,1H), 3.92(s,3H).

[0237] Step 4: Methyl 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoate [ka] A mixture of methyl 5-cyano-2-(trifluoromethyl)-4-(trifluoromethylsulfonyloxy)benzoate (1.75 g, 4.64 mmol), [4-(trifluoromethyl)phenyl]boronic acid (1.76 g, 9.28 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.536 g, 0.464 mmol), and potassium carbonate (1.6 g, 11.6 mmol) in 1,4-dioxane (30.0 mL) was stirred at 110° C. under a nitrogen atmosphere for 16 hours. The reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic layers were dried over NaSO, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give a white solid (1.50 g, 86.6%). A 200 ml solution of 1,4-dioxane in DMSO-d6 was added to give a white solid (1.50 g, 86.6%). 1 H-NMR[ppm]:8.53(s,1H), 8.17(s,1H), 7.90-8.10(m,4H), 3.93(s,3H).

[0238] Step 5: 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoate [ka] Sodium hydroxide (0.643 g, 16.1 mmol) in water (5 mL) was added dropwise to a solution of methyl 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoate (2.00 g, 5.36 mmol) in methanol (10 mL) and water (5 mL). Tetrahydrofuran (10 mL) was added after 5 minutes. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into aqueous hydrochloric acid, extracted with ethyl acetate (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give a white solid (1.40 g, 72.7%). DMSO-d6 1 H-NMR [ppm]: 8.46 (s, 1H), 8.11 (s, 1H), 7.90-8.10 (m, 4H). This material was used in the next step.

[0239] Step 6: 5-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile (compound P1.1) [ka] To a solution of 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoic acid (200 mg, 0.557 mmol) in dichloromethane (10.0 mL) was added 5-methyl-3-(4-piperidyl)-1,2,4-oxadiazole hydrochloride (126 mg, 0.618 mmol, 1.11 equiv.), synthesized as described in Nippon Soda's patent application WO 2017195703. Subsequently, HATU (234 mg, 0.615 mmol, 1.11 equiv.) and diisopropyl-ethyl-amine (216 mg, 1.68 mmol, 3.01 equiv.) were added. The reaction mixture was stirred at room temperature for 21 hours and then poured into aqueous NaHCO3 solution. The mixture was extracted three times with ethyl acetate. The aqueous layer was acidified with 2 N hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (ethyl acetate / petroleum ether=1:2) to give 205 mg (yield: 72%) of 5-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile as a white solid. 1H-NMR[ppm]:7.85(d,2H), 7.82-7.74(m,2H), 7.70(d,2H), 4.64(s,1H), 3. 49(d,1H), 3.31-3.02(m,3H), 2.59(d,3H), 2.19(d,1H), 2.06-1.79(m,3H). 7.74-7.88(m,4H), 7.70(d,2H), 4.60(t,1H), 3.50(t,1H), 3.02-3.40(m,3H ), 2.57(d,3H), 2.10-2.25(m,1H), 1.79-2.06(m,3H).LC-MS (Method 1): RT=4.80 min;[M+H] + =509.

[0240] Example P2: 5-[4-(3,5-dichloro-2-pyridyl)piperazine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile (compound P2.1): [ka] To a solution of 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoic acid (158 mg, 0.44 mmol) in DMF (5 mL) was added 4-(3,5-dichloro-2-pyridyl)piperazine (108 mg, 0.463 mmol), HATU (201 mg, 0.528 mmol), and diisopropylethylamine (227 mg, 1.76 mmol). The reaction mixture was stirred at room temperature for 16 hours. The mixture was then poured into water and extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether = 1:1) to give the product (187 mg, 74%) as a white solid. The product was eluted with HCl in CDCl3. 1 H-NMR[ppm]:8.16(s,1H), 7.88(s,1H), 7.76-7.85(m,3H), 7.71(d,2H), 7.70(s,1H), 3.85-4.10(m,2H), 3.25-3.53(m,6H).LC-MS(Method 1): RT=5.51 min;[M+H] + =574.

[0241] Example P3: 5-[4-(3,5-dichloro-2-pyridyl)piperazine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzenecarbothioamide (compound P8.1): [ka] To a solution of 5-[4-(3,5-dichloro-2-pyridyl)piperazine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile (0.134 g, 0.234 mmol) in DMF (2.3 mL) was added magnesium dichloride (0.062 g, 0.304 mmol, 1.3 equiv.). The mixture was stirred at room temperature for 1 hour. Sodium hydrosulfide (0.05 g, 0.888 mmol, 3.8 equiv.) was then added, and stirring was continued at room temperature for 1 hour. The reaction mixture was treated with saturated aqueous NHCl4 and then extracted three times with ethyl acetate. The organic phase was dried over Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by chromatography to give the desired product (130 mg, 91%) as a white foam. A 100% HCl solution in CDCl3 was added. 1 H-NMR[ppm]:8.18(s,1H), 7.62-7.80(m,7H), 7.01(bs,1H), 6.97(bs,1H), 3.85-4.10(m,2H), 3.25-3.60(m,6H).LC-MS(Method 2): RT=1.25 min;[M+H] + =607.

[0242] Example P4: 5-[4-(3,5-dichloro-2-pyridyl)piperazine-1-carbonyl]-4-ethoxy-2-[4-(trifluoromethyl)-phenyl]-benzonitrile (compound P2.5): [ka] Step 1: Ethyl 4-amino-5-cyano-2-hydroxy-benzoate [ka] To a solution of sodium ethoxide (1.1 equiv.) in ethanol (20% w / w), propanedinitrile (1.32 g, 20 mmol, 1 equiv.) was slowly added at 4° C., and the mixture was stirred for 15 minutes. Next, a solution of ethyl (2E)-2-(ethoxymethylene)-3-oxobutonate (3.72 g, 20 mmol) in ethanol (50 mL) was added with ice cooling. The reaction mixture was heated to reflux for 1 hour. After cooling, the reaction mixture was diluted with ethyl acetate and water. The phases were separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. 2.45 g (59% yield) of ethyl 4-amino-5-cyano-2-hydroxybenzoate was obtained as a white solid. The DMSO solution 1 H NMR[ppm]: 10.98(s,1H), 7.89(s,1H), 6.79(s,2H), 6.20(s,1H), 4.28(q,2H), 1.30(t,3H).LC-MS(Method 1): RT=3.98 min;[M+H] + =207.

[0243] Step 2: Ethyl 5-cyano-2-hydroxy-4-iodo-benzoate [ka] To a solution of boron trifluoride diethyl etherate (568 mg, 4 mmol) in THF (5 mL) was added a solution of ethyl 4-amino-5-cyano-2-hydroxybenzoate (412 mg, 4 mmol) in THF (5 mL) at 0 °C. The mixture was then cooled to -10 °C, tert-butyl nitrite (268 mg, 2.6 mmol) was added, and the reaction mixture was stirred at -10 °C for 0.5 h. Sodium iodide (390 mg, 2.6 mmol) in acetone (10 mL) was then added, and the mixture was stirred at room temperature for 1.5 h. The reaction mixture was diluted with ethyl acetate and water. The phases were separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether=1:2) to give the product (599 mg, 94.5%) as a white solid. 1 H NMR[ppm]: 11.36(s,1H), 8.07(s,1H), 7.63(s,1H), 4.32(q,2H), 1.32(t,3H).LC-MS(Method 1): RT=4.76 min;[M+H] + =318.

[0244] Step 3: Ethyl 5-cyano-2-ethoxy-4-iodo-benzoate [ka] To a solution of ethyl 5-cyano-2-hydroxy-4-iodobenzoate (1.17 g, 3.7 mmol) in acetone (50 mL) was added iodoethane (867 mg, 5.56 mmol) and potassium carbonate (767 mg, 5.56 mmol). The mixture was stirred and heated to reflux for 5 hours. After cooling, the reaction mixture was diluted with ethyl acetate and water. The phases were separated, and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether = 1:5) to give the product (372 mg, 29%) as a white solid.1 H NMR[ppm]:7.99(s,1H), 7.45(s,1H), 4.35(q,2H), 4.16(q,2H), 1.49(t,3H), 1.38(t,3H).LC-MS(Method 1): RT=4.683 min;[M+H] + =346.

[0245] Step 4: Ethyl 5-cyano-2-ethoxy-6-[4-(trifluoromethyl)phenyl]pyridine-3-carboxylate [ka] A mixture of ethyl 5-cyano-2-ethoxy-6-iodo-pyridine-3-carboxylate (370 mg, 1.07 mmol), 1-[4-(trifluoromethyl)phenyl]boronic acid (408 mg, 2.14 mmol), Pd(PPh3)4 (247 mg, 0.21 mmol), and potassium carbonate (443 mg, 3.21 mmol) in 1,4-dioxane (20.0 mL) was stirred at 90 °C under nitrogen for 16 h. The mixture was then poured into water and extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether = 1:5) to give the product (380 mg, 97.5%) as a white solid. The product was eluted with 100 ml of CDCl3. 1 H NMR[ppm]:8.22(s,1H), 7.77(d,2H), 7.68(d,2H), 7.01(s,1H), 4.40(q,2H), 4.22(q,2H), 1.52(t,3H), 1.41(t,3H).LC-MS(Method 1): RT=3.615 min;[M+H] + =364.

[0246] Step 5: 5-cyano-2-ethoxy-4-[4-(trifluoromethyl)phenyl]benzoic acid [ka] Ethyl 5-cyano-2-ethoxy-4-[4-(trifluoromethyl)phenyl]benzoate (1.3 g, 3.58 mmol) was dissolved in tetrahydrofuran (10 mL), and potassium hydroxide (429 mg, 10.7 mmol, 3.0 equiv.) dissolved in water (2 mL) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was then diluted with ethyl acetate and 2N hydrochloric acid. The mixture was extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed to give the crude product (1.2 g, 100%) as a white solid, which was used directly in the next step.

[0247] Step 6: 5-[4-(3,5-dichloro-2-pyridyl)piperazine-1-carbonyl]-4-ethoxy-2-[4-(trifluoromethyl)-phenyl]-benzonitrile (compound P2.5): [ka] To a solution of 5-cyano-2-ethoxy-4-[4-(trifluoromethyl)phenyl]benzoic acid (121 mg, 0.36 mmol) in DMF (5 mL) was added 1-(3,5-dichloro-2-pyridyl)piperazine (99 mg, 0.43 mmol), HATU (163 mg, 0.43 mmol), and diisopropylethylamine (139 mg, 1.08 mmol). The reaction mixture was stirred at room temperature for 16 hours. The mixture was then poured into water and extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether = 1 / 1) to give the product (140 mg, 71%) as a white solid. The product was eluted with HCl in CDCl3. 1 H NMR[ppm]:8.16(d,1H), 7.74(d,2H), 7.71(s,1H), 7.64-7.68(m,3H), 6.97(s, 1H), 4.15-4.25(m,2H), 3.80-4.20(m,2H), 1.48(t,3H).LC-MS (Method 1): RT=5.627 min;[M+H] + =550.

[0248] Example P5: 4-Ethoxy-5-[4-(ethylsulfanylmethyl)piperidine-1-carbonyl]-2-[4-(trifluoromethyl)phenyl]-benzonitrile (compound P1.46): [ka] To a solution of 5-cyano-2-ethoxy-4-[4-(trifluoromethyl)phenyl]benzoic acid (140 mg, 0.42 mmol) in DMF (5 mL) was added 4-(ethylsulfanylmethyl)piperidine hydrochloride (117 mg, 0.598 mmol), HATU (190 mg, 0.5 mmol), and diisopropylethylamine (163 mg, 1.62 mmol). The reaction mixture was stirred at room temperature for 16 hours. The mixture was then poured into water and extracted three times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over Na2SO4, and the solvent was removed. The crude product was purified by chromatography on silica gel (ethyl acetate / petroleum ether = 1:1) to give the product (127 mg, 64%) as a white solid. The product was eluted with HCl in CDCl3. 1 H NMR[ppm]:7.76(d,2H), 7.60-7.70(m,3H), 6.94(d,1H), 4.78(t,1H), 4.09-4.25(m,2H), 3.49(d,1H), 2.90-3.10(m,1H), 2.79 (q,1H), 2.42-2.59(m,4H), 1.90-2.05(m,1H), 1.69-1.85(m,2H), 1.40-1.51(m,3H), 1.20-1.30(m,5H).LC-MS (Method 1): RT=5.32 min;[M+H] + =477.

[0249] Example P6: 4-Ethoxy-5-[4-(ethylsulfanylmethyl)piperidine-1-carbonyl]-2-[4-(trifluoromethyl)phenyl]-benzonitrile (compound P3.7): [ka] Step 1: tert-Butyl 3-(acetylsulfanylmethyl)azetidine-1-carboxylate [ka] Acetylsulfanyl sodium (85.0%, 0.462 g, 4.00 mmol) was added to tert-butyl 3-(bromomethyl)-azetidine-1-carboxylate (0.500 g, 2.00 mmol) in acetone (10.0 mL) at room temperature, and the mixture was stirred at room temperature for 16 hours. The mixture was then poured into dilute hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 315 mg (yield: 64%) of tert-butyl 3-(acetylsulfanylmethyl)-azetidine-1-carboxylate. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 315 mg (yield: 64%) of tert-butyl 3-(acetylsulfanylmethyl)-azetidine-1-carboxylate. 1 H NMR[ppm]:3.98(t,2H), 3.56(dd,2H), 3.09(d,2H), 2.62-2.78(m,1H), 2.34(s,3H), 1.42(d,9H).LC-MS(Method 1): RT=4.25 min;[M+Na] + =268.

[0250] Step 2: tert-Butyl 3-(sulfanylmethyl)azetidine-1-carboxylate [ka] Sodium borohydride (0.308 g, 8.15 mmol) was added to tert-butyl 3-(acetylsulfanylmethyl)azetidine-1-carboxylate (1.00 g, 4.08 mmol) in methanol (10.0 mL) and stirred at room temperature for 16 hours. The mixture was then poured into dilute hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 528 mg (yield: 64%) of tert-butyl 3-(sulfanylmethyl)azetidine-1-carboxylate. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 528 mg (yield: 64%) of tert-butyl 3-(sulfanylmethyl)azetidine-1-carboxylate. 1 H NMR[ppm]:4.02(t,2H), 3.60(dd,2H), 2.73(t,2H), 2.61-2.65(m,1H), 1.43(s,9H), 1.30(t,1H).LC-MS(Method 1): RT=4.11 min;[M+Na] + =226.

[0251] Step 3: tert-Butyl 3-(propylsulfanylmethyl)azetidine-1-carboxylate [ka] 1-Iodopropane (0.627 g, 3.69 mmol) was added to tert-butyl 3-(sulfanylmethyl)azetidine-1-carboxylate (500 mg, 2.46 mmol) and K2CO3 (1.02 g, 7.38 mmol) in acetone (10.0 mL), and the reaction mixture was stirred at room temperature for 16 hours. The mixture was then poured into dilute hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 331 mg (yield: 52%) of tert-butyl 3-(propylsulfanylmethyl)azetidine-1-carboxylate. The crude product was purified by column chromatography on silica gel (petroleum ether / ethyl acetate = 20:1) to give 331 mg (yield: 52%) of tert-butyl 3-(propylsulfanylmethyl)azetidine-1-carboxylate. 1H NMR[ppm]: 4.02(t,2H), 3.60(dd,2H), 2.60-2.75(m,3H), 2.47(t,2H), 1.54-1.63(m,2H), 1.43(s,9H), 0.98(t,3H).

[0252] Step 4: Trifluoroacetate of 3-(propylsulfanylmethyl)azetidine [ka] tert-Butyl 3-(propylsulfanylmethyl)azetidine-1-carboxylate (500 mg, 2.04 mmol) and 2,2,2-trifluoroacetic acid (0.929 g, 8.15 mmol) in dichloromethane (15.0 mL) were stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure and used in the next step. 1 H NMR[ppm]: 4.17(s,2H), 3.90(s,2H), 3.13(t,1H), 2.78(d,2H), 2.48(t,2H), 1.64-1.52(m,2H), 0.98(t,3H).

[0253] Step 5: 5-[3-(propylsulfanylmethyl)azetidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)-phenyl]benzonitrile [ka] To a solution of 5-cyano-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]benzoic acid (150 mg, 0.418 mmol) in DMF (5 mL) was added the trifluoroacetate salt of 3-(propylsulfanylmethyl)azetidine (162 mg, 0.626 mmol, 1.5 equiv.). Subsequently, HATU (238 mg, 0.626 mmol, 1.5 equiv.) and diisopropylethylamine (162 mg, 1.25 mmol, 3.00 equiv.) were added. The reaction mixture was stirred at room temperature for 16 hours and then poured into aqueous NaHCO3 solution. The mixture was extracted three times with ethyl acetate. The aqueous layer was acidified with 2 N hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (petroleum ether / ethyl acetate=1:1) to give 121 mg (yield: 60%) of 5-[3-(propylsulfanylmethyl)azetidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-benzonitrile as a colorless gum. 1 H-NMR[ppm]:7.85(s,1H), 7.77-7.83(m,3H), 7.69(d,2H), 4.33(t,1H), 4.05(t,1H), 3.92(dd,1H), 3.6 6(dd,1H), 2.65-2.99(m,3H), 2.40-2.60(m,2H), 1.55-1-70(m,2H), 0.98(t,3H).LC-MS (Method 1): RT=5.38 min;[M+H] + =487.

[0254] Step 6: 5-[3-(propylsulfinylmethyl)azetidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]-benzonitrile (compound P3.7) [ka] 3-Chloroperbenzoic acid (0.034 g, 0.197 mmol, 0.8 equiv.) was added to 5-[3-(propylsulfanylmethyl)-azetidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile (120 mg, 0.247 mmol) in dichloromethane (20 mL) and stirred at room temperature for 2 hours. The mixture was then poured into a saturated solution of NaHCO3 and Na2SO3 in water and extracted three times with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (ethyl acetate / petroleum ether=1:2) to give 41 mg (yield: 33%) of 5-[3-(propylsulfinylmethyl)azetidine-1-carbonyl]-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzonitrile as a colorless gum in DMSO-d6. 1 H-NMR[ppm]:8.32(s,1H), 8.09(s,1H), 7.88-7.96(m,4H), 4.24(t,1H), 4.05-4.15(m,1H), 3.68-3.97(m,1H) ), 3.82(dd,1H), 2.96-3.20(m,3H), 2.60-2.75(m,2H), 1.53-1.71(m,2H), 0.98(t,3H).LC-MS (Method 1): RT=4.36 min;[M+H] + =503.

[0255] Example P7: 4-methyl-5-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]-2-[4-(trifluoromethyl)phenyl]benzene-1,3-dicarbonitrile (compound P6.1): [ka] Step 1: Ethyl 4-amino-3,5-dicyano-2-methyl-benzoate [ka] A solution of ethyl acetoacetate (1.3 mL, 0.01 mmol) in methanol was cooled to 0°C and then treated with aqueous formaldehyde (1 mL). The reaction mixture was stirred for 3 hours, and then a solution of malononitrile (1.2 g, 0.2 mmol) in methanol (30 mL) was added slowly with stirring over a period of 1 hour, followed by the addition of a solution of morpholine (0.8 mL, 0.1 mmol) in methanol (20 mL). The mixture was cooled on ice for 3 hours and then allowed to stand at room temperature for 48 hours. The solid was filtered off and washed with a small amount of methanol to give the desired compound (1.8 g, 78%). 1 H-NMR[ppm]:8.02(s,1H), 7.17(s,2H), 4.26(q,2H), 2.65(s,3H), 1.35(t,3H).MS(ESI)[M+H] + =230.0.

[0256] Step 2: Ethyl 3,5-dicyano-4-iodo-2-methyl-benzoate [ka] Ethyl 4-amino-3,5-dicyano-2-methylbenzoate (1.90 g, 8.3 mmol) was suspended in H2SO4 (40 mL, 50%), cooled to -5 °C, and stirred for 1 h. A solution of sodium nitrite (0.86 g, 12.5 mmol) in water (5 mL) was slowly added, and the mixture was stirred at 0 °C for 30 min. The yellow slurry was then slowly added to an ice-cold solution of potassium iodide (13.8 g, 83 mmol) in water (230 mL). The ice bath was then removed, and the foamy suspension was stirred at room temperature for 2 h. Dichloromethane (100 mL) was added, followed by saturated Na2SO3 solution. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined dichloromethane layers were dried over Na2SO4 and the solvent was evaporated to give ethyl 3,5-dicyano-4-iodo-2-methyl-benzoate (0.8 g, 28%). 1H-NMR[ppm]:8.27(s,1H), 4.20(q,2H), 2.50(s,3H), 1.42(t,3H).MS(ESI)[M+H] += 341.1.

[0257] Step 3: Ethyl 3,5-dicyano-2-methyl-4-[4-(trifluoromethyl)phenyl]benzoate [ka] A mixture of ethyl 3,5-dicyano-4-iodo-2-methylbenzoate (0.74 g, 2.18 mmol), [4-(trifluoromethyl)phenyl]boronic acid (0.62 g, 3.26 mmol), sodium carbonate (0.46 g, 4.33 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.25 g, 0.218 mmol) in toluene (20 mL) / water (6 mL) was stirred at 80 °C overnight. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was separated, washed with brine (20 mL), dried over magnesium sulfate, and concentrated under reduced pressure. Purification by column chromatography (ethyl acetate / petroleum ether = 2:1) afforded the desired compound (0.7 g, 90%). A 200-ml solution of 1,2-dichloro-3,4-dichloro-2,5-dichloro-2,6-dichloro-2,5 ... 1 H-NMR[ppm]:8.45(s,1H), 7.84(d,2H), 7.64(d,2H), 4.46(q,2H), 2.97(s,3H), 1.45(t,3H).MS(ESI)[M+H] + =359.3.

[0258] Step 4: 3,5-dicyano-2-methyl-4-[4-(trifluoromethyl)phenyl]benzoic acid [ka] To a solution of ethyl 3,5-dicyano-2-methyl-4-[4-(trifluoromethyl)phenyl]benzoate (0.56 g, 1.56 mmol) in methanol (10 mL), sodium hydroxide (75 mg, 1.88 mmol) was added. The mixture was stirred at room temperature for 2 hours. Then, the pH was adjusted to 2-3 by adding hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the product (0.5 g, 97%). In DMSO-d6 1 H-NMR[ppm]:8.57(s,1H), 8.02(d,2H), 7.87(d,2H), 2.83(s,3H).MS(ESI)[M+H] + =331.3.

[0259] Step 5: 4-Methyl-5-[4-(5-methyl-1,2,4-oxadiazol-3-yl)piperazine-1-carbonyl]-2-[4-(trifluoromethyl)-phenyl]benzene-1,3-dicarbonitrile (Compound P6.1) [ka] A mixture of 3,5-dicyano-2-methyl-4-[4-(trifluoromethyl)phenyl]benzoic acid (250 mg, 0.757 mmol), 5-methyl-3-(4-piperidyl)-1,2,4-oxadiazole (127 mg, 0.757 mmol), synthesized as described in Nippon Soda's patent application WO 2017195703, diisopropylethylamine (294 mg, 2.27 mmol), and HATU (431 mg, 1.14 mol) in dichloromethane (10 mL) was stirred at room temperature for 4 hours. The mixture was poured into water (50 mL), extracted three times with ethyl acetate (50 mL each), and the combined organic phases were dried over Na2SO4 and concentrated. The material was purified by chromatography (ethyl acetate / petroleum ether = 1:2) to give the title compound as a solid (230 mg, 63%). in CDCl 1H-NMR[ppm]:7.84(d,2H), 7.76, 7.79(2s,1H), 7.63(d,2H), 4.63(t,1H), 3.53(d,1H), 3.10-3.30(m,3H), 2.64, 2.59(2s,3H), 2.58(s,3H), 1.75-2.25(m,4H).MS(ESI)[M+H] + =480.2.

[0260] The compounds in Tables P1, P2, P3, P4, P5, P6, P7 and P8 were prepared as described in the examples above or in similar manner.

[0261] Table P1: Compounds of formula (Ic) [ka] The compounds in Table P1 may be prepared as described in the examples above or by similar methods. The following abbreviations are used in the tables below: RT = retention time, min = minutes, mp = melting point or melting range.

[0262] [Table 13-1] [Table 13-2] [Table 13-3]

[0263] Table P2: Compounds of formula (Id) [ka] The compounds in Table P2 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes, mp = melting point.

[0264] [Table 14]

[0265] Table P3: Compounds of formula (Ie) [ka] The compounds in Table P3 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes; mp = melting point.

[0266] [Table 15]

[0267] Table P4: Compounds of formula (Ie) [ka] The compounds in Table P2 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes, mp = melting point.

[0268] [Table 16]

[0269] Table P5: Compounds of formula (Ig) [ka] The compounds in Table P5 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes; mp = melting point.

[0270] [Table 17]

[0271] Table P6: Compounds of formula (Ih) [ka] The compounds in Table P6 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes; mp = melting point.

[0272] [Table 18]

[0273] Table P7: Compounds of formula (Ii) [ka] The compounds in Table P7 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes; mp = melting point.

[0274] [Table 19]

[0275] Table P8: Compounds of formula (Ij) [ka] The compounds in Table P8 may be prepared as described in the examples above or in similar manner. The following abbreviations are used in the tables below: RT = retention time, min = minutes; mp = melting point.

[0276] [Table 20]

[0277] The intermediates in Table U1 are novel and useful for the synthesis of several compounds of general structure I. They can be prepared as described in the examples above or similar methods. The following abbreviations are used in the table below: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.

[0278] [Table 21-1] [Table 21-2]

[0279] The activity of the composition according to the present invention can be considerably broadened and adapted to the general situation by adding other insecticidally, acaricidally and / or fungicidal active ingredients.The mixture of the compound of formula (I) with other insecticidally, acaricidally and / or fungicidal active ingredients can also have further unexpected advantages, which may be described in a broader sense as synergistic activity.For example, better tolerance by plants, reduced phytotoxicity, insects can be controlled at different stages of their development, or better behavior during their preparation, for example, during grinding or mixing, during their storage, or during their use.

[0280] Suitable additives to the active ingredients herein are, for example, exemplified by the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0281] The following mixtures of compounds of formula (I) with active substances are preferred (the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8"): an adjuvant selected from the group of substances consisting of petroleum (alternative name) (628) + TX; Abamectin +TX, Acequinocyl +TX, Acetamiprid +TX, Acetoprole +TX, Acrinathrin +TX, Acinonapyr +TX, Afidopiropen +TX, Afoxolaner +TX, Alanycarb +TX, Allethrin +TX, α-Cypermethrin +TX, α-Methrin +TX, Amidoflumet +TX, Aminocarb +TX, Azocyclotine +TX, Bensultap +TX, Benzochimate +TX, Benzpyrimoxane +TX, β-Cyfluthrin +TX, β-Cypermethrin +TX, Bifenazate +TX, Bifenthrin +TX, Binapacryl + TX, Bioallethrin + TX, Bioallethrin S)-Cyclopentyl Isomer + TX, Bioresmethrin + TX, Bistrifluron + TX, Brofuranilide + TX, Broflutrinate + TX, Bromophos-ethyl + TX, Buprofezin + TX, Butocarboxim + TX, Cadusafos + TX, Carbaryl + TX, Carbosulfan + TX, Cartap + TX, CAS Number: 1632218-00-8 + TX, CAS Number: 1808115-49-2 + TX, CAS Number: 2032403-97-5 + TX, CAS Number: 2044701-44-0 + TX, CAS number: 2128706-05-6 + TX, CAS number: 2246757-58-2 (or 2249718-27-0) + TX, CAS number: 907187-07-9 + TX, chlorantraniliprole + TX, chlordane + TX, chlorfenapyr + TX, chlorprallethrin + TX, chromafenozide + TX, clenpirin + TX, cloetocarb + TX, clothianidin + TX, 2-chlorophenyl N-methylcarbamate (CPMC) + TX, cyanofenphos + TX, cyantraniliprole + TX, cyclaniliprole + TX, Cyclobutrifluram + TX, cycloprothrin + TX, cycloxapride + TX, cycloxapride + TX, cyenopyrafen + TX, cyetopyrafen + TX, cyflumetofen + TX, cyfluthrin + TX, cyhalodiamide + TX, cyhalothrin + TX, cypermethrin + TX, cyphenothrin + TX, cyprofuranilide + TX, cyromazine + TX, deltamethrin + TX, diafenthiuron + TX, dialifos + TX, dibrom + TX, dichloromezothiaz + TX, diflobidazin + TX, diflubenzuron + TX, dimepropyridaz + TX,Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzophos + TX, Emamectin (or Emamectin benzoate) + TX, Empenthrin + TX, ε-Monfluorotrin + TX, ε-Metofluthrin + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etofenprox + TX, Etoxazole + TX, Fanfar + TX, Fenazaquin + TX, Fenfluthrin + TX, Fenitrothion + TX, Fenobucarb + TX, Fenothiocarb + TX, Fenoxycarb + TX, Fenpro Patrin +TX, Fenpyroximate +TX, Fensulfothion +TX, Fenthion +TX, Fentin acetate +TX, Fenvalerate +TX, Fipronil +TX, Flometoquin +TX, Flonicamid +TX, Fluacrypyrim +TX, Fluazaindolizine +TX, Fluazuron +TX, Flubendiamide +TX, Flubenzimine +TX, Flucythrinate +TX, Flucycloxuron +TX, Flucythrinate +TX, Fluensulfone +TX, Flufenerim +TX, Flufenprox +TX, Flufiprole +TX, Fluhexafon + TX, Flumethrin + TX, Fluopyram + TX, Flupentiofenox + TX, Flupyradifurone + TX, Flupirimine + TX, Fluralaner + TX, Fluvalinate + TX, Fluxamethamide + TX, Fosthiazate + TX, γ-cyhalothrin + TX, Gossiplua (trademark) + TX, Guadipyr + TX, Halofenozide + TX, Halofenozide + TX, Halfenprox + TX, Heptafluthrin + TX, Hexythiazox + TX, Hydramethylnon + TX, Imicyafos + TX, Imidacloprid + TX, Imipro Torin + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, isocycloceram + TX, isothioate + TX, ivermectin + TX, κ-bifenthrin + TX, κ-tefluthrin + TX, λ-cyhalothrin + TX, lepimectin + TX, lufenuron + TX, metaflumizone + TX, metaldehyde + TX, metam + TX, methomyl + TX, methoxyfenozide + TX, metofluthrin + TX, metolcarb + TX, mexacarbate + TX, milbemectin + TX, monfluorotrin + TX, niclosamide + TX,Nicofluprole +TX; Nitenpyram +TX, Nithiazine +TX, Omethoate +TX, Oxamyl +TX, Oxazosulfil +TX, Parathion-ethyl +TX, Permethrin +TX, Fenothrin +TX, Phosphocarb +TX, Piperonyl butoxide +TX, Pirimicarb +TX, Pirimiphos-ethyl +TX, Pirimiphos-methyl +TX, Polyhedrosis virus +TX, Prallethrin +TX, Profenofos +TX, Profenofos +TX, Profluthrin +TX, Propargite +TX, Propetamphos +TX, Propoxar +TX, Prothir Ojos +TX, Protrifenbuter +TX, Piflubumid +TX, Pymetrozine +TX, Pyraclofos +TX, Pyrafluprole +TX, Pyridaben +TX, Pyridalyl +TX, Pyrifluquinazon +TX, Pyrimidifen +TX, Pyriminostrobin +TX, Pyriprole +TX, Pyriproxyfen +TX, Resmethrin +TX, Sarolaner +TX, Selamectin +TX, Silafluofen +TX, Spinetoram +TX, Spinosad +TX, Spirodiclofen +TX, Spiromesifen +TX, Spiropydione +TX, Spirotetramat +TX X, sulfoxaflor + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tefluthrin + TX, temephos + TX, tetrachlorantraniliprole + TX, tetradifon + TX, tetramethrin + TX, tetramethylfluthrin + TX, tetranactin + TX, tetraniliprole + TX, θ-cypermethrin + TX, thiacloprid + TX, thiamethoxam + TX, thiocyclam + TX, thiodicarb + TX, thiofanox + TX, thiometon + TX, thiosultap + TX, thioxazafen + TX, Rufenpyrad + TX, Toxaphene + TX, Tralomethrin + TX, Transfluthrin + TX, Triazamate + TX, Triazophos + TX, Trichlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Triflumezopyrim + TX, Cyclopyrazoflor + TX, Zeta-cypermethrin + TX, Seaweed extract and fermented product from Melasse + TX, Seaweed extract and fermented product from Melasse containing urea + TX, Amino acids + TX, Potassium and molybdenum and EDTA-chelated manganese + TX, Seaweed extract and fermented plant product + TX,Fermented plant products containing seaweed extract and plant hormones +TX, vitamins +TX, EDTA-chelated copper +TX, zinc +TX and iron +TX, azadirachtin +TX, Bacillus aizawai +TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618) +TX, Bacillus firmus +TX, Bacillus kurstaki +TX, Bacillus mycoides AQ726 (NRRL accession number B-21664) +TX, Bacillus pumilus (NRRL accession number B-30087) +TX, Bacillus pumilus AQ717 (NRRL accession number B-21662) + TX, Bacillus sp. AQ178 (ATCC accession number 53522) + TX, Bacillus sp. AQ175 (ATCC accession number 55608) + TX, Bacillus sp. AQ177 (ATCC accession number 55609) + TX, unspecified Bacillus subtilis + TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL accession number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL accession number B-21530) + TX, Bacillus thuringiensis subspec. kurstaki BMP 123 + TX,Beauveria bassiana + TX, D-limonene + TX, granulovirus + TX, harpin + TX, Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa zea nuclear polyhedrosis virus + TX, Heliothis virescens nuclear polyhedrosis virus + TX, Heliothis punctigera nuclear polyhedrosis virus + TX, Metarhizium spp. + TX, Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3-5 (NRRL accession number 30548) + TX, Neem tree tree product + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae + TX, P-cymene + TX, Plutella xylostella granulosis virus + TX, Plutella xylostella nuclear polyhedrosis virus + TX, polyhedrosis virus + TX, pyrethrum + TX, QRD 420 (terpenoid blend) + TX, QRD 452 (terpenoid blend) + TX, QRD 460 (terpenoid blend) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Spodoptera frugiperda nuclear polyhedrosis virus + TX,Streptomyces galbus (NRRL Accession No. 30232) + TX, Streptomyces sp. (NRRL Accession No. B-30145) + TX, terpenoid blend + TX and Verticillium spp.; an algicide selected from the group of substances consisting of bethoxadin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dichloron (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamide (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX; an anthelmintic selected from the group of substances consisting of abamectin (1) + TX, crufomate (1011) + TX, cyclobutrifluram + TX, doramectin (alternative name) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX; an avian repellent selected from the group of substances consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX; 1-Hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodicine (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydrargafen (alternative name) [CCN] + T a fungicide selected from the group of substances consisting of X, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, tecloftalam (766) + TX, and thiomersal (alternative name) [CCN] + TX; Adoxophyes orana GV (alternate name) (12) + TX, Agrobacterium radiobacter (alternate name) (13) + TX, Amblyseius spp. (alternate name) (19) + TX, Anagrapha falcifera NPV (alternate name) (28) + TX, Anagrus atomus (alternate name) (29) + TX, Aphelinus abdominalis (alternate name) (33) + TX, Aphidius colemani (alternate name) (34) + TX, Aphidoletes aphidimyza (alternate name) (35) + TX, Autographa californica californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis subsp. japonensis) (scientific name) (51) + TX, Bacillus thuringiensis subsp. kurstaki (scientific name) (51) + TX, Bacillus thuringiensis subsp. tenebrionis (Bacillus thuringiensis subsp.tenebrionis (scientific name) (51) + TX, Beauveria bassiana (alternate name) (53) + TX, Beauveria brongniartii (alternate name) (54) + TX, Chrysoperla carnea (Japanese lacewing) (alternate name) (151) + TX, Cryptolaemus montrouzieri (red ladybird) (alternate name) (178) + TX, Cydia pomonella GV (alternate name) (191) + TX, Dacnusa sibirica (leaf-cone wasp) (alternate name) (212) + TX, Diglyphus isaea (alternate name) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (alternate name) (300) + TX, Helicoverpa zea NPV (alternate name) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alternate name) (433) + TX, Hippodamia convergens (alternate name) (442) + TX, Leptomastix dactylopii (alternate name) (488) + TX, Macrolophus caliginosus (alternate name) (491) + TX, Mamestra brassicae NPV (alternate name) (494) + TX, Metaphycus helvolus (alternate name) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, Neodiprion sertifer NPV and N. leconti (N.lecontei NPV (alternate name) (575) + TX, Orius spp. (alternate name) (596) + TX, Paecilomyces fumosoroseus (alternate name) (613) + TX, Phytoseiulus persimilis (alternate name) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternate name) (742) + TX, Steinernema carpocapsae (alternate name) (742) + TX, Steinernema felziae feltiae (alternate name) (742) + TX, Steinernema glaseri (alternate name) (742) + TX, Steinernema riobrave (alternate name) (742) + TX, Steinernema riobravis (alternate name) (742) + TX, Steinernema scapterisci (alternate name) (742) + TX, Steinernema spp. (alternate name) (742) + TX, Trichogramma spp. (alternate name) (826) + TX, Typhlodromus occidentalis a biological agent selected from the group of substances consisting of Verticillium lecanii (alternative name) (848) + TX; a soil sterilant selected from the group of substances consisting of iodomethane (IUPAC name) (542) and methyl bromide (537) + TX; antisterilizing agents selected from the group of substances consisting of Afolate [CCN] + TX, Visadyl (alternative name) [CCN] + TX, Busulfan (alternative name) [CCN] + TX, Diflubenzuron (250) + TX, Zimatif (alternative name) [CCN] + TX, Hemel [CCN] + TX, Hempa [CCN] + TX, Metepa [CCN] + TX, Methiotepa [CCN] + TX, Methyl Afolate [CCN] + TX, Morzide [CCN] + TX, Penfluron (alternative name) [CCN] + TX, Tepa [CCN] + TX, Thiohempa (alternative name) [CCN] + TX, Thiotepa (alternative name) [CCN] + TX, Tretamine (alternative name) [CCN] and Uredepa (alternative name) [CCN] + TX; (E)-Deca-5-en-1-yl acetate and (E)-dec-5-en-1-ol (IUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradec-4,1 0-Dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-Dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-Hexadec-11-enal (IUPAC name) (436) + TX, (Z)-Hexadec-11-en-1-yl acetate (IUPAC name) (437) + TX, (Z)-Hex Sadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-Icos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, ( Z)-Tetradeca-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one (IUPAC name) (544) + TX, α-multistriatin (alternative name) [CCN] + TX, Brevicomin (alternative name) [CCN] + TX, Codlerua (alternative name) [CCN] + TX, Codlemone (alternative name) (167) + TX, Curua ( (alternative name) (179) + TX, disparlure (277) + TX, dodec-8-en-1-yl acetate (IUPAC name) (286) + TX, dodec-9-en-1-yl acetate (IUPAC name) (287) + TX, dodec-8 + TX, 10-dien-1-yl acetate (IUPAC name) (284) + TX, dominicalure (alternative name) [CCN] + TX, ethyl 4-methyloctanoate (IUPAC name) (317) + TX, eugenol (alternative name) ) [CCN] + TX, Frontalin (alternate name) [CCN] + TX, Gossip Lua (alternate name) (420) + TX, Grand Lua (421) + TX, Grand Lua I (alternate name) (421) + TX, Grand Lua II (alternate name) (421) + TX, Grand Lua III (alternate name) (421) + TX, Grand Lua IV (alternate name) (421) + TX, Hexalua [CCN] + TX, Ipsdienol (alternate name) [CCN] + TX, Ipsenol (alternate name [ CCN] + TX, Japonirua (alternative name) (481) + TX, Lineatin (alternative name) [CCN] + TX, Litirua (alternative name) [CCN] + TX, Lupulua (alternative name) [CCN] + TX, Medurua [CCN] + TX, Megatomoic acid (alternative name) [CCN] + TX, Methyleugenol (alternative name) (540) + TX, Muscalua (563) + TX, Octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, Octadeca-3,13-Dien-1-yl acetate (IUPAC name) (589) + TX, Olfrulure (alternative name) [CCN] + TX, Orictalure (alternative name) (317) + TX, Ostramon (alternative name) [CCN] + TX, Siglua [CCN] + TX, Soldigin (alternative name) (736) + TX, Sulcatol (alternative name) [CCN] + TX, Tetradec-11-en-1-yl acetate (IU an insect pheromone selected from the group of substances consisting of Trimedulla (PAC name) (785) + TX, Trimedulla (839) + TX, Trimedulla A (alternate name) (839) + TX, Trimedulla B1 (alternate name) (839) + TX, Trimedulla B2 (alternate name) (839) + TX, Trimedulla C (alternate name) (839) and Trunk-call (alternate name) [CCN] + TX; an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX; Bis(tributyltin)oxide (IUPAC name) (913) + TX, Bromoacetamide [CCN] + TX, Calcium arsenate [CCN] + TX, Cloethocarb (999) + TX, Copper acetarsenite [CCN] + TX, Copper sulfate (172) + TX, Fentin (347) + TX, Ferric phosphate (IUPAC name) (352) + TX, Metaldehyde (518) + TX, Methiocarb (530) + TX, Niclosamide (576) + TX, Niclosamide-olamine (576) + TX, Pentachloroethylene (Phenylalanine) a molluscicide selected from the group of substances consisting of: chlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, thazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913) + TX, triphenmorph (1454) + TX, trimethacarb (840) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX, pyriprole [394730-71-3] + TX; AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / Chemical Abstracts Name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts Name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC Name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts Name) (Plastic name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alternative name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxicarb (863) + TX, AZ60541 (compound code) + TX, benclotiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alternative name) + TX, cadusafos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbosulfan (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, cloetocarb (999) + TX, cyclobutrifluram + TX, cytokinin (alternative name) (210) + T X, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidaphos (1044) + TX, Diclofenthion (1051) + TX, Dicrifos (alternative name) + TX, Dimethoate (262) + TX, Doramectin (alternative name) [CCN] + TX, Emamectin (291) + TX, Emamectin Benzoate (291) + TX, Eprinomectin (alternative name) [CCN] + TX, Ethoprophos (312) + TX, Ethyl Dibromide len (316) + TX, fenamiphos (326) + TX, fenpyrad (alternative name) + TX, fensulfothion (1158) + TX, fosthiazate (408) + TX, fostietan (1196) + TX, furfural (alternative name) [CCN] + TX, GY-81 (development code) (423) + TX, heterophos [CCN] + TX, iodomethane (IUPAC name) (542) + TX, isamidophos (1230) + TX, isazophos (1231) + TX, ebe Lumectin (alternative name) [CCN] + TX, Kinetin (alternative name) (210) + TX, Mecarfone (1258) + TX, Metam (519) + TX, Metam-potassium (alternative name) (519) + TX, Metam-sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alternative name) [CCN] + TX, Moxidectin (alternative name) [CCN] + TX, Myrotheciumverrucaria) Composition (alternative name) (565) + TX, NC-184 (compound code) + TX, Oxamyl (602) + TX, Phorate (636) + TX, Phosphamidon (639) + TX, Phosphocarb [CCN] + TX, Cebufos (alternative name) + TX, Selamectin (alternative name) [CCN] + TX, Spinosad (737) + TX, Terbam (alternative name) + TX, Terbufos (773) + TX, Tetrachlorothiophene (IU a nematicide selected from the group of substances consisting of PAC / Chemical Abstracts Name) (1422) + TX, Thiafenox (alternative name) + TX, Thionazine (1434) + TX, Triazophos (820) + TX, Triazuron (alternative name) + TX, Xylenol [CCN] + TX, YI-5302 (compound code) and Zeatin (alternative name) (210) + TX, Fluensulfone [318290-98-1] + TX, Fluopyram + TX; a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX; a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX; 2-Isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, anthracene (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoium (89) + TX, bromadiolone (including α-bromadiolone) + TX, bromide Lomethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, difenacoum (246) + TX, difethialone (249) + TX, diphacinone (273) + TX, ergocalciferol (301) + TX, flocculate Phenol (357) + TX, Fluoroacetamide (379) + TX, Flupropazine (1183) + TX, Flupropazine Hydrochloride (1183) + TX, γ-HCH (430) + TX, HCH (430) + TX, Hydrogen Cyanide (444) + TX, Iodomethane (IUPAC name) (542) + TX, Lindane (430) + TX, Magnesium Phosphide (IUPAC name) (640) + TX, Methyl Bromide (537) + TX, Norbormide (1318) + TX, Fosacetim (1336) + TX, Phosphido a rodenticide selected from the group of substances consisting of arsenic (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pyrinuron (1371) + TX, sciliroside (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX; a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol and nerolidol (alternative names) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piperotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesamolin (1394) and sulfoxide (1406) + TX; an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetate (422) + TX, methiocarb (530) + TX, pyridin-4-amine (IUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN], and ziram (856) + TX; a virucidal agent selected from the group of substances consisting of Imanin (alternative name) [CCN] and Ribavirin (alternative name) [CCN] + TX; a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octilinone (590) and thiophanate-methyl (802) + TX; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-cinnamaldehyde + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic trioxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + TX, benzyl benzoate Oxalate +TX, Bixafen +TX, Brofenvalerate +TX, Bromocyclen +TX, Bromophos +TX, Bromopropylate +TX, Buprofezin +TX, Butocarboxim +TX, Butoxycarboxim +TX, Butylpyridaben +TX, Calcium polysulfate +TX, Camphechlor +TX, Carbanolate +TX, Carbophenothion +TX, Cimiazole +TX, Thiomethionate +TX, Chlorbeside +TX, Chlordimeform +TX, Chlordimeform hydrochloride +TX, Chlorphenetole +TX, Chlorfenson +TX , Chlorofensulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerins +TX, Closantel +TX, Coumaphos +TX, Crotamiton +TX, Crotoxyphos +TX, Kufraeb +TX, Cyanthoate +TX, DCPM +TX, DDT +TX, Demefion +TX, Demefion-O +TX, Demefion-S +TX, Demeton-methyl +TX, Demeton-O +TX, Demeton-O-methyl +TX , Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX, Dofenapine+TX, Doramectin+TX, Endothion+TX,Epirinomectin +TX, Ethoate-methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxuron +TX, Fluenethyl +TX, Fluorobenside +TX, FMC 1137+TX, formetanate+TX, formetanate hydrochloride+TX, formparanate+TX, γ-HCH+TX, gliodin+TX, halfenprox+TX, hexadecylcyclopropanecarboxylate+TX, isocarbophos+TX, jasmolin I+TX, jasmolin II+TX, jodofenphos+TX, lindane+TX, malonoven+TX, mecarbam+TX, mefosfolan+TX, mesulfen+TX, methacrifos+TX, methyl bromide+TX, metolcarb+TX, mexacarbate+TX, milbemycin oxime+TX, Mipafox + TX, monocrotophos + TX, morphothion + TX, moxidectin + TX, naled + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifururizide + TX, nikkomycin + TX, nitrilacarb + TX, nitrilacarb 1:1 zinc chloride complex + TX, omethoate + TX, oxydeprophos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, fencapton + TX, phosalone + TX, phospholan + TX, phosphamidon + TX, polychloroterpenes + TX, polychloroterpenes Linactin +TX, Proclonol +TX, Promacyl +TX, Propoxur +TX, Protidathion +TX, Protoate +TX, Pyrethrin I +TX, Pyrethrin II +TX, Pyrethrin +TX, Pyridaphenthion +TX, Pirimitate +TX, Quinalphos +TX, Quinthiofos +TX, R-1492 +TX, Phosglycine +TX, Rotenone +TX, Schladan +TX, Cebufos +TX, Selamectin +TX, Sofamid +TX, SSI-121 +TX, Sulfiram +TX, Sulfuramide +TX, Sulfotep +TX, Sulfur +TX, Diflobidazin +TX, τ-Fulvalinate +TX, TEPP +TX, Thelbam +TX,Tetradifon + TX, Tetrasul + TX, Thiafenox + TX, Thiocarboxim + TX, Thiofanox + TX, Thiometon + TX, Thioquinox + TX, Thuringiensin + TX, Triamiphos + TX, Triatene + TX, Triazophos + TX, Triazuron + TX, Trifenofos + TX, Trinactin + TX, Vamidothion + TX, Vaniliprole + TX, Bethoxadin + TX, Copper dioctanoate + TX , Copper sulfate + TX, Sibutrin + TX, Dichlorn + TX, Dichlorophen + TX, Endothal + TX, Fentin + TX, Slaked lime + TX, Nabam + TX, Quinoclamine + TX, Quinoneamide + TX, Simazine + TX, Triphenyltin acetate + TX, Triphenyltin hydroxide + TX, Crufomate + TX, Piperazine + TX, Thiophanate + TX, Chloralose + TX, Fenthion + TX, Pyridin-4-amine + T X, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, doditin + TX, fenaminosulf + TX, formaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV+TX, Agrobacterium radiobacter+TX, Amblyseius spp.+TX, Anagrapha falcifera NPV+TX, Anagrafa atomus+TX, Aphelinus abdominalis+TX, Aphidius colemani+TX,Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Codling moth (Cydia pomonella GV) + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX,Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii) + TX, apholate + TX, Visadil + TX, busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, methyl apholate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z )-Hexadec-11-enal + TX, (Z)-Hexadec-11-en-1-yl acetate + TX, (Z)-Hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-Icos-13-en-10-one + TX, (Z)-Tetradeca-7-en-1-al + TX, (Z)-Tetradeca-9-en-1-ol + TX, ( Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX,4-Methylnonan-5-ol and 4-methylnonan-5-one + TX, α-multistriatin + TX, Brevicomin + TX, Codrelle + TX, Codlemone + TX, Querle + TX, Disparlure + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8 + TX, 10-dien-1-yl acetate + TX, Dominicalure + TX, Ethyl 4-Methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grandolure + TX, Grandolure I + TX, Grandolure II + TX, Grandolure III + TX, Grandolure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX, Japonilure + TX, Lineatin + TX, Litulure + TX, Lupulure + TX, Medulure + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalure + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1- Il acetate + TX, Olfural + TX, Orictal + TX, Ostramon + TX, Siglua + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedlure + TX, Trimedlure A + TX, Trimedlure B1 + TX, Trimedlure B2 + TX, Trimedlure C + TX, Trunc-call + TX, 2-(octylthio)ethanol + TX, Butapyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate +TX, dibutyl succinate +TX, diethyl toluamide +TX, dimethylcarbate +TX, dimethyl phthalate +TX, ethyl hexanediol +TX, hexamide +TX, methoquin-butyl +TX, methyl neodecanoamide +TX, oxamate +TX, picaridin +TX, 1-dichloro-1-nitroethane +TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane +TX, 1,2-dichloropropane and 1,3-dichloropropene +TX, 1-bromo-2-chloroethane +TX, 2,2,2-trichloro-1-(3,4-dichloro 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX,2-Methyl(prop-2-ynyl)aminophenylmethylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixycarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis (Bacillus thuringiensis) δ-endotoxin +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, bartholin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, β-cyfluthrin +TX, β-cypermethrin +TX, bioethanomethrin +TX, biopermethrin +TX, bis(2-chloroethyl) ether +TX, sodium borate +TX, bromfenvinphos +TX, bromo-DDT +TX, bufencarb +TX, butacarb +TX, butathiophos +TX, butonate +TX, calcium arsenate +TX, calcium cyanide +TX, carbon disulfide +TX, carbon tetrachloride +TX, cartap hydrochloride +TX, sevadin +TX, chlorbicyclen +TX, chlordane +TX, Chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocitrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, chumithoate + TX, cryolite + TX, CS708 + TX, cyanofenphos + TX, cyanophos + TX, cicrethrin + TX, cithioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamidaphos + TX, dikapton + TX, dichlorophenthion + TX, dicresyl + TX, dicyclanil + TX, dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, dilol + TX, dimefluthrin + TX,Dimethane +TX, Dimethryn +TX, Dimethylvinphos +TX, Dimethylan +TX, Dinoprop +TX, Dinosam +TX, Dinoseb +TX, Diofenolan +TX, Dioxabenzophos +TX, Dicyclophos +TX, DSP +TX, Ecdysterone +TX, EI 1642 +TX, EMPC +TX, EPBP +TX, Ethyl Formate +TX, Ethylene Dibromide +TX, Dichloroethane +TX, Ethylene Oxide +TX, EXD +TX, Fenchlorphos +TX, Fenetacarb +TX, Fenitrothion +TX, Fenoxacrim +TX, Fenpyrithrin +TX, Fensulfothion +TX, Fenthion-Ethyl +TX, Flucofuron +TX, Fosmetyllan +TX, Fospirate +TX, Fos Thietane + TX, Furathiocarb + TX, Frethrin + TX, Guazatine + TX, Guazatine acetate + TX, Sodium tetrathiocarbonate + TX, Halfenprox + TX, HCH + TX, HEOD + TX, Heptachlor + TX, Heterofos + TX, HHDN + TX, Hydrogen cyanide + TX, Hikincarb + TX, IPSP + TX, Isazophos + TX, Isobenzane + TX, Isodrin + TX, Isofenphos + TX, Isolane + TX, Isoprothiolane + TX, Isoxa Thione + TX, larval hormone I + TX, larval hormone II + TX, larval hormone III + TX, Kelevan + TX, Kinoprene + TX, lead arsenate + TX, leptophos + TX, lilimphos + TX, ritidathion + TX, m-cumenylmethylcarbamate + TX, magnesium phosphide + TX, magidox + TX, mecarfone + TX, menasone + TX, mercurous chloride + TX, mesulfenphos + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, methane sulfonate Phonyl + TX, Metocrotophos + TX, Methoprene + TX, Methotrin + TX, Methoxychlor + TX, Methyl isothiocyanate + TX, Methyl chloroform + TX, Methylene chloride + TX, Methoxadiazone + TX, Mirex + TX, Naphthalophos + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nicotine sulfate + TX, Nithiazine + TX, Nornicotine + TX, O-5-Dichloro-4-iodophenyl O-ethylethylphosphonothioate + TX,O,O-Diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-Diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-Tetrapropyldithiopyrophosphate + TX, Oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38 + TX, Fenkapton + TX, Fosnichlor + TX, Phosphine + TX, Phoxim-methyl + TX, Pyrimetaphos + TX, Polychlorodicyclopentadiene Isomers + TX, Potassium Arsenite + TX, Potassium Thiocyanate + TX, Precocene I + TX, Precocene II + TX, Precocene III + TX, Pyrimidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pyrazophos + TX, Pyrethmetry methicone + TX, cassia + TX, quinalphos-methyl + TX, quinothione + TX, lafoxanide + TX, resmethrin + TX, rotenone + TX, cadetrin + TX, ryania + TX, ryanodine + TX, sabadila + TX, shradan + TX, cevufos + TX, SI-0009 + TX, tiapronil + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, pentachloroisothiazolinone + TX, ... Lofenoxide sodium salt +TX, sodium selenate +TX, sodium thiocyanate +TX, sulcofuron +TX, sulcofuron-sodium +TX, sulfuryl fluoride +TX, sulprofos +TX, tar oil +TX, thionazine +TX, TDE +TX, tebupirimfos +TX, temephos +TX, telallethrin +TX, tetrachloroethane +TX, cyclofos +TX, thiocyclam +TX, thiocyclam hydrogen oxalate +TX, thicyclam Onadine + TX, Thiosultap + TX, Thiosultap-sodium + TX, Tralomethrin + TX, Transpermethrin + TX, Triazamate + TX, Trichlormethaphos-3 + TX, Trichloronat + TX, Trimethacarb + TX, Tolprocarb + TX, Triclopyricarb + TX, Triplen + TX, Veratridine + TX, Veratrine + TX, XMC + TX, Zetamethrin + TX, Zinc Phosphide + TX, Zolaprofos + TX,and meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4- chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, rufural + TX, isamidophos + TX, kinetin + TX, Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenol + TX, zeatin + TX, potassium ethylxanthate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, Reynoutria sachalinensis) extract +TX, α-chlorohydrin +TX, Anz +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocoumafen +TX, fluoroacetamide + TX, flupropazine + TX, flupropazine hydrochloride + TX, norbormide + TX, fosacetim + TX, phosphorus + TX, pindone + TX, pyrinuron + TX, sciliroside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, -2-(2-butoxyethoxy)ethyl piperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol and nerolidol + TX, berubutin + TX, MGK 264 + TX, piperonyl butoxide + TX, piprotal + TX, propyl isomers + TX,S421+TX, Sesamex+TX, Sesamolin+TX, Sulfoxide+TX, Anthraquinone+TX, Copper naphthenate+TX, Copper oxychloride+TX, Dicyclopentadiene+TX, Thiram+TX, Zinc naphthenate+TX, Ziram+TX, Imanin+TX, Ribavirin+TX, Chlorinconazid+TX, Mercury(II) oxide+TX, Thiophanate-Me, Chil + TX, Azaconazole + TX, Bitertanol + TX, Bromuconazole + TX, Cyproconazole + TX, Difenoconazole + TX, Diniconazole + TX, Epoxiconazole + TX, Fenbuconazole + TX, Fluquinconazole + TX, Flusilazole + TX, Flutriafol + TX, Furametpyr + TX, Hexaconazole + TX, Imazalil + TX, Imibenconazole + TX, Ipconazole + TX, Metconazole + TX, Myclobutanil + TX, Paclobutrazol + TX, Pefurazoate + TX, Penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrisoxazole + TX, -simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimate + TX, dimethirimol + TX, ethirimol + TX, dodemorph + TX, fenpropidin + TX, fenpropimorph + TX, spiroxamine + TX , tridemorph +TX, cyprodinil +TX, mepanipyrim +TX, pyrimethanil +TX, fenpiclonil +TX, fludioxonil +TX, benalaxyl +TX, furalaxyl +TX, -metalaxyl +TX, R-metalaxyl +TX, ofrace +TX, oxadixyl +TX, carbendazim +TX, debacarb +TX, fuberidazole +TX, thiabendazole +TX, chlozolinate +TX, dichlozolin +TX, mycozolin +TX, procymidone +TX, vinclozolin +TX, boscalid +TX, carboxin +TX, fenfuram + TX, flutolanil + TX, mepronil + TX, oxycarboxin + TX, penthiopyrad + TX, thifluzamide + TX, dodine + TX, iminoctadine + TX, azoxystrobin + TX, dimoxystrobin + TX, enestrobulin + TX, phenaminestrobin + TX, flufenoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, trifloxystrobin + TX, oryzastrobin + TX, picoxystrobin + TX, pyraclostrobin + TX, pyrametostrobin + TX,Pyraoxystrobin +TX, Ferbam +TX, Mancozeb +TX, Maneb +TX, Metiram +TX, Propineb +TX, Zineb +TX, Captafol +TX, Captan +TX, Fluorimide +TX, Folpet +TX, Tolylfluanid +TX, Bordeaux mixture +TX, Copper oxide +TX, Mancopper +TX, Oxine copper +TX, Nitrothal-isopropyl +TX, Edifenphos +TX, Iprobenfos +TX, Fosdifen +TX, Turcofos-methyl +TX, Anilazine +TX, Benthiavalicarb +TX, Blast Cydin-S+TX, Chloroneb-+TX, Chlorothalonil+TX, Cyflufenamid+TX, Cymoxanil+TX, Diclocymet+TX, Diclomedine-+TX, Dicloran+TX, Diethofencarb+TX, Dimethomorph-+TX, Flumorph+TX, Dithianon+TX, Ethaboxam+TX, Etridiazole+TX, Famoxadone+TX, Fenamidon+TX, Fenoxanil+TX, Ferimzone+TX, Fluazinam+TX, Fluopicolide+TX, Flusulfamide+TX, Fluxapyroxad+TX, -F Enhexamide + TX, Fosetyl-aluminum + TX, Hymexazole + TX, Iprovalicarb + TX, Cyazofamid + TX, Methasulfocarb + TX, Metrafenone + TX, Pencycuron + TX, Phthalide + TX, Polyoxin + TX, Propamocarb + TX, Pyribencarb + TX, Proquinazide + TX, Pyroquilon + TX, Pyriophenone + TX, Quinoxyfen + TX, Quintozene + TX, Tiadinil + TX, Triazoxide + TX, Tricyclazole + TX, Triforine + TX, Validamycin + TX, Valifenol Fenalate + TX, zoxamide + TX, mandipropamide + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupyr + TX, pydiflumetofen + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isotianil + TX, dipimethitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX,2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(Difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-Bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4- (2-Bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, fluindapyr + TX, methoxystrobin (jiaxiangjunzhi) + TX, rubenmixianan + TX, diclobenthiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro) -2-Methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, t-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, inpirfluxam + TX, turolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine- 3-Carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid + TX,But-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl] Pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole- 3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, tebufloquine + TX, ipulfenoquin + TX, quinofumelin + TX, isofetamide + TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide Voxamide + TX, benzothiostrobin + TX, fenamacril + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropoin + TX, picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiproline + T X, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Oxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy] ]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX,N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared by the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds were prepared by the method described in WO 2018 / 228896). N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by the methods described in WO 2019 / 110427);N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[( 1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[( 3-Fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]- ]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared by the methods described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds were prepared by the method described in WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared by the methods described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX phenyl]phenyl]methyl]propanamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph can be prepared by 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]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared by the method described in WO 2017 / 029179); 3 -[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); (4-phenoxyphen N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene (N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene) with TX (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone with TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzene Carbothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX;N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared by the method described in WO 2018 / 065 414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared by the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX biologically active substances selected from N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the methods described in WO 2018 / 202428); Microorganisms including: Acinetobacter lwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternata + TX, Alternaria cassia + TX, cassia) + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp.) + TX, Aureobasidium pullulans + TX, Azospirillum + TX, (MicroAZ® + TX, TAZO B®) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (Biostart™ Rhizoboost®) + TX, Bacillus licheniformis strain 3086 (EcoGuard® + TX, Green Releaf®) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe® + TX, BioNem-WP® + TX, VOTiVO®) + TX, Bacillus firmus strain I-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium megaterium) + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder®) + TX, Bacillus pumilus spp.) + TX, Bacillus pumilus strain GB34 (Yield Shield®) + TX, Bacillus pumilus strain AQ717 + TX, Bacillus pumilus strain QST 2808 (Sonata® + TX, Ballad Plus®) + TX, Bacillus spahericus (VectoLex®) + TX, Bacillus spp. + TX, Bacillus spp. strain AQ175 + TX, Bacillus spp. strain AQ177 + TX, Bacillus spp. strain AQ178 + TX, Bacillus subtilis Bacillus subtilis strain QST 713 (CEASE®+TX, Serenade®+TX, Rhapsody®)+TX, Bacillus subtilis strain QST 714 (JAZZ®)+TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis var. amyloliquefaciens (Bacillus subtilis var.amyloliquefaciens strain FZB24 (Taegro® +TX, Rhizopro®) +TX, Bacillus thuringiensis Cry 2Ae +TX, Bacillus thuringiensis Cry1Ab +TX, Bacillus thuringiensis aizawai GC 91 (Agree®) +TX, Bacillus thuringiensis israelensis (BMP123® +TX, Aquabac® +TX, VectoBac®) +TX, Bacillus thuringiensis kurstakii kurstaki (Javelin® + TX, Deliver® + TX, CryMax® + TX, Bondide® + TX, Scutella WP® + TX, Turilav WP® + TX, Astuto® + TX, Dipel WP® + TX, Biobit® + TX, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis var. aizawai (XenTari®+TX, DiPel®)+TX, Bacteria spp.) (GROWMEND® +TX, GROWSWEET® +TX, Shootup®) +TX, Clavipacter michiganensis bacteriophage (AgriPhage®) +TX, Bakflor® +TX, Beauveria bassiana (Beaugenic® +TX, Brocaril WP®) +TX, Beauveria bassiana GHA (Mycotrol ES® +TX, Mycotrol O® +TX, BotaniGuard®) +TX, Beauveria brongniartii (Engerlingspilz® +TX, Schweizer Beauveria® +TX, Melocont®) +TX, Beauveria species (Beauveria spp.) + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor®) + TX, BtBooster + TX, Burkholderia cepacia (Deny® + TX, Intercept® + TX, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp.) + TX, Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida leucoffii reukaufii + TX, Candida saitoana (Bio-Coat® + TX, Biocure®) + TX, Candida sake + TX, Candida spp. + TX, Candida tenius + TX, Cedecea dravisae + TX, Cellulomonas flavigena + TX, Chaetomium cochliodes (Nova-Cide®) + TX, Chaetomium globosum (Nova-Cide®) + TX, Chromobacterium subtsugae subtsugae strain PRAA4-1T (Grandevo®) + TX, Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium chlorocephalum. chlorocephalum + TX, Cladosporium spp. + TX, Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp.) + TX, Cryptococcus albidus (YIELDPLUS®) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex®) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X®) + TX, Cydia pomonella granulovirus granulovirus) (Madex® + TX, Madex Plus® + TX, Madex Max / Carpovirusine®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacter iacae + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum + TX, Epicoccum purpuraense purpurascens) + TX, Epicoccum spp.) + TX, Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean® / Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop® + TX, Prestop®) + TX, Gliocladium roseum roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulovirus (Granupom®) + TX, Halobacillus halophilus + TX, Halobacillus litoralis + TX, Halobacillus trueperi + TX, Halomonas spp.) + TX, Halomonas subglaciescola + TX, Halovibrio variabilis + TX, Hanseniaspora uvarum + TX, Helicoverpa armigera nuclear polyhedrosis virus (Helicovex®) + TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar®) + TX, isoflavone-formononetin (Myconate®) + TX, Kloeckera apiculata + TX, Kloeckera spp.) + TX, Lagenidium giganteum (Laginex®) + TX, Greenhouse whitefly (Lecanicillium longisporum) (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Gypsy moth (Lymantria dispar) nuclear polyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin®) + TX, WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp.) (AMykor® +TX, Root Maximizer®) +TX, Myrothecium verrucaria strain AARC-0255 (DiTera®) +TX, BROS PLUS® +TX, Ophiostoma piliferum strain D97 (Sylvanex®) +TX, Paecilomyces farinosus +TX, Paecilomyces fumosoroseus (PFR-97® +TX, PreFeRal®) +TX, Paecilomyces linacinus (Biostat WP®) +TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp. + TX, Pasteuria spp. (Econem®) + TX, Pasteuria nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart® + TX, TagTeam®) + TX, Penicillium brevicompactum brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.) + TX, Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, Phosphhomeal® + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa aeruginosa + TX, Pseudomonas aureofaciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas spp.) + TX, Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudomonas fluorescens (Zequanox®) + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron® + TX, Polyv. ersum (registered trademark) + TX, Pythium periplocum (Pythium periplocum) + TX, Rhanella aquatilis (Rhanella aquatilis) + TX, Rhanella spp. (Rhanella spp.) + TX, Rhizoctonia (Dormal (registered trademark) + TX, Vault (registered trademark)) + TX, Rhizoctonia (Rhizoctonia) + TX, Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum (Rhodosporidium diobovatum) + TX, Rhodosporidium toruloides (Rhodotorula) + TX, Rhodotorula spp. (Rhodotorula glutinis) + TX, Rhodotorula graminis (Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Saccharomyces cerevisiae + TX, Salinococcus roseus + TX, Sclerotinia minor + TX, Sclerotinia minor (SARRITOR®) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X® + TX, Spexit®) + TX, Serratia marcescens marcescens) + TX, Serratia plymuthica + TX, Serratia spp.) + TX, Sordaria fimicola + TX, Spodoptera littoralis nuclear polyhedrosis virus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albadoncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis griseoviridis (Mycostop®) + TX, Streptomyces lydicus (Actinovate®) + TX, Streptomyces lydicus WYEC-108 (ActinoGrow®) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp.) + TX, Trichoderma asperellum (T34 Biocontrol®) + TX, Trichoderma gamsii (Tenet®) + TX, Trichoderma atroviride (Plantmate®) + TX, Trichoderma hamatum TH 382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P® + TX, PlantShield HC® + TX, RootShield® + TX, Trianum-G®) + TX, Trichoderma harzianum) T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp.LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans pullulans) + TX, Trichosporon spp. + TX, Trichothecium spp.) + TX, Trichothecium roseum + TX, Typhula phacorrhiza strain 94670 + TX, Typhula phacorrhiza strain 94671 + TX, Ulocladium atrum + TX, Ulocladium oudemansii (Botry-Zen®) + TX, Ustilago maydis + TX, various bacteria and supplemental micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii lecanii (Mycotal® + TX, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus; Plant extracts including: pine oil (Retenol®) +TX, azadirachtin (Plasma), Neem Oil® +TX, AzaGuard® +TX, MeemAzal® +TX, Molt-X® +TX, botanical insect growth regulators (Neemazad® +TX, Neemix®) +TX, rapeseed oil (Lilly Miller Vegol®) +TX, American ant's weed (Chenopodium ambrosioides near ambrosioides) (Requiem®) +TX, Chrysanthemum extract (Crisant®) +TX, neem oil extract (Trilogy®) +TX, Labiatae essential oil (Botania®) +TX, clove, rosemary, peppermint, and thyme oil extracts (Garden insect killer®) + TX, glycine betaine (Greenstim®) + TX, garlic + TX, lemongrass oil (GreenMatch®) + TX, neem oil + TX, catnip (Nepeta cataria) (catnip oil) + TX, catnip (Nepeta catarina) + TX, nicotine + TX, oregano oil (MossBuster®) + TX, sesame (Pedaliaceae) oil (Nematon®) + TX, pyrethrum + TX, soapberry (Quillaja saponaria) (NemaQ®) + TX, giant knotweed (Reynoutria sachalinensis) (Regalia® + TX, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae extract (Soleo®) + TX, soybean oil (Ortho ecosense®) +TX, tea tree oil (Timorex Gold®) +TX, thyme oil +TX, AGNIQUE® MMF +TX, BugOil® +TX, a mixture of rosemary, sesame, peppermint, thyme and cinnamon extracts (EF300®) + TX, a mixture of clove rosemary and peppermint extracts (EF 400®) + TX, a mixture of clove peppermint garlic oil and mint (Soil Shot®) + TX, kaolin (Screen®) + TX, storage glucan from brown algae (Laminarin®); Pheromones, including: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, grape berry moth pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, leafroller pheromone (3M MEC-LR Sprayable Pheromone®) + TX, muscamone (Snip7 Fly Bait® + TX, Starbar Premium Fly Bait®) + TX, oriental fruit moth pheromone (3M oriental fruit moth sprayable pheromone®) + TX, peachtree Borer pheromone (Isomate-P®) + TX, Tomato Pinworm pheromone (3M Sprayable pheromone®) + TX, Entostat powder (palm tree extract) (Exosex CM®) + TX, (E+TX,Z+TX,Z)-3+TX, 8+TX, 11-tetradecatrienyl acetate + TX, (Z+TX,Z+TX,E)-7+TX, 11+TX, 13-hexadecatrienal + TX, (E+TX,Z)-7+TX, 9-dodecadien-1-yl acetate + TX, 2-methyl-1-butanol + TX, calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, Lavandulyl senecioate; Macrobials including: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System®) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System®) + TX, Adalia bipunctata (Adaline®) + TX, Adalia bipunctata (Aphidalia®) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersonii andersoni (Anderline® + TX, andersoni-System®) + TX, Amblyseius californicus (Amblyline® + TX, Spical®) + TX, Amblyseius cucumeris (Thripex® + TX, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii® + TX, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidin hesperidum + TX, Anagyrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococcuspseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline® + TX, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifuensis + TX, Aphidius matricariae matricariae (Aphipar-M®) + TX, Aphidoletes aphidimyza (Aphidend®) + TX, Aphidoletes aphidimyza (Aphidoline®) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline®) + TX, Bombus spp. + TX, Bombus terrestris (Natupol Beehive® + TX, Bombus terrestris (Beeline® + TX, Tripol®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperlacarnea (Chrysoline®) + TX, Chrysoperla carnea (Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug® + TX, Cryptoline®) + TX, Cybocephalus nipponicus (Dacnusa sibirica) + TX, Dacnusa sibirica (Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catarinae (Delphastus catalinae) (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsisjucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus® + TX, Digline®) + TX, Dacnusa sibirica (DacDigline® + TX, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max® + TX, Encarline® + TX, En-Strip®) + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmoceris siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal® + TX, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus mundus) (Bemipar® + TX, Eretline m®) + TX, Eretmocerus siphonini + TX, Exochomus quadripustulatus + TX, Feltiellaacarisuga (Spidend®) + TX, Feltiella acarisuga (Feltiline®) + TX, Fopius arisanus + TX, Fopius ceratitivorus + TX, formononetin (Wirless Beehome®) + TX, Franklinothrips vespiformis (Vespop®) + TX, Galendromus occidentalis + TX, Goniozus legneri + TX, Habrobracon hebetor + TX, Harmonia axyridis axyridis (HarmoBeetle®) + TX, Heterorhabditis spp. (Lawn Patrol®) + TX, Heterorhabditis bacteriophora (NemaShield HB® + TX, Nemaseek® + TX, Terranem-Nam® + TX, Terranem® + TX, Larvanem® + TX, B-Green® + TX, NemAttack® + TX, Nematop®) + TX, Heterorhabditis megidis (Nemasys H® + TX, BioNem H® + TX, Exhibitline hm® + TX, Larvanem-M®) + TX, Hippodamia convergens) + TX, Hypoaspis aculeifer (Aculeifer-System® + TX, Entomite-A®) + TX, Hypoaspis miles (Hypoline m® + TX, Entomite-M®) + TX, Lbalia leucospoidesleucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopi + TX tylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N® + TX, Macroline c® + TX, Mirical®) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus longusburii lounsburyi + TX, Micromus angulatus (Milacewing®) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar®) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumeris (THRYPEX®) + TX, Neoseiulus fallacis + TX, Nesideocoris tenuis tenuis) (NesidioBug® + TX, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Orius insidiosus (Thripor-I® + TX, Oriline i®) + TX, Oriuslaevigatus (Thripor-L® + TX, Oriline l®) + TX, Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimmon (Phytoseiulus persimilis (Spidex® + TX, Phytoline p®) + TX, Podisus maculiventris (Podisus®) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicana + TX, Psyllaephagus pilosus + TX, Psyttalia concolor (complex) + TX, Quadrastichus spp.) + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Rumina decollate + TX, Semielacher petiolatuspetiolatus +TX, Sitobion avenae (Ervibank®) +TX, Steinernema carpocapsae (Nematac C® +TX, Millenium® +TX, BioNem C® +TX, NemAttack® +TX, Nemastar® +TX, Capsanem®) +TX, Steinernema feltiae (NemaShield® +TX, Nemasys F® +TX, BioNem F® +TX, Steinernema-System® +TX, NemAttack® +TX, Nemaplus® +TX, Exhibitline sf® + TX, Scia-rid® + TX, Entonem® + TX, Steinernema kraussei (Nemasys L® + TX, BioNem L® + TX, Exhibitline srb®) + TX, Steinernema riobrave (BioVector® + TX, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernema spp. (Guardian Nematodes®) + TX, Stethorus punctilum punctillum) (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogrammabrassicae) (Tricholine b®) + TX, Trichogramma brassicae) (Tricho-Strip®) + TX, Trichogramma evanescens) + TX, Trichogramma minutum) + TX, Trichogramma ostriniae) + TX, Trichogramma platneri) + TX, Trichogramma pretiosum) + TX, Xanthopimpla stemmator); Other biological products include: abscisic acid +TX, bioSea® +TX, Chondrostereum purpureum (Chontrol Paste®) +TX, Colletotrichum gloeosporioides (Collego®) +TX, copper octanoate (Cueva®) +TX, Delta Trap (Trapline d®) +TX, Erwinia amylovora (Harpin) (ProAct® +TX, Ni-HIBIT Gold CST®) +TX, Ferri-phosphate (Ferramol®) +TX, Funnel Trap (Trapline y®) +TX, Gallex® +TX, Grower's Secret® + TX, Homo-brassonolide + TX, Iron phosphate (Lilly Miller Worry Free Ferramol Slug & Snail Bait®) + TX, MCP hail trap (Trapline f®) + TX, Microctonus hyperodae + TX, Mycoleptodiscus terrestris (Des-X®) + TX, BioGain® + TX, Aminomite® + TX, Zenox® + TX, pheromone trap (Thripline ams®) + TX, potassium bicarbonate (MilStop®) + TX, potassium salts of fatty acids (Sanova®) + TX, potassium silicate solution (Sil-Matrix®) + TX, potassium iodide + potassium thiocyanate (Enzicur®) + TX, SuffOil-X® + TX, spider venom + TX, Nosema locustae (Semaspore Organic Grasshopper Control®) + TX, sticky traps (Trapline YF® + TX, RebellAmarillo®) + TX and trap (Takitrapline y+b®) + TX; and Safeners such as benoxacor + TX, cloquintocet (including cloquintocet-mexyl) + TX, cyprosulfamide + TX, dichlormid + TX, fenchlorazole (including fenchlorazole-ethyl) + TX, fenclorim + TX, fluxofenim + TX, furilazole + TX, isoxadifen (including isoxadifen-ethyl) + TX, mefenpyr (including mefenpyr-diethyl) + TX, metcamifen + TX and oxabetrinil + TX.

[0282] The reference numbers in square brackets after the active ingredient, such as [3878-19-1], refer to the Chemical Abstracts Registration Number. The above-mentioned compounds are known. When the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS Tomlin; The British Crop Protection Council], they are listed therein under the section number shown in parentheses above for the specific compound; for example, the compound "abamectin" is listed under section number (1). When "[CCN]" is added to a specific compound above, the corresponding compound 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 listed at the Internet address: http: / / www.alanwood.net / pesticides / acetoprole.html.

[0283] Most of the active ingredients mentioned above are referred to above by so-called "common names", and the relevant "ISO common names" or another "common name" is used in individual cases. If the designation is not a "common name", the nature of the designation used instead is indicated in parentheses for the particular compound; in that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "trivial name", "compound name" or "development code" is used, or if neither one of these designations nor a "common name" is used, an "alternative name" is used. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0284] The active ingredient mixture of a compound of formula (I) selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8 with the above-mentioned active ingredient is preferably a mixture of a compound selected from one of the compounds defined in Tables 1 to 35 and Tables P1 to P8 and the above-mentioned active ingredient in a mixing ratio of 100:1 to 1:6000, in particular 50:1 to 1:50, more in particular 20:1 to 1:20, even more in particular 10:1 to 1:10, very in particular 5:1 and 1:5 (a ratio of 2:1 to 1:2 is particularly preferred, a ratio of 4:1 to 2:1 is also preferred), in particular 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. These mixing ratios are by weight.

[0285] The mixture may be used in a method for controlling pests, the method comprising the step of applying a composition comprising the mixture to the pest or its environment, excluding methods of treatment of the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0286] Mixtures comprising a compound of formula (I) selected from the compounds defined in Tables 1 to 35 and Tables P1 to P8 and one or more of the active ingredients described above can be applied, for example, in a single ready-mix form, as a combined spray mixture composed of separate formulations of a single active ingredient, such as a "tank mix," and in combination with a single active ingredient when applied sequentially, i.e., one after the other over a fairly short period of time, such as a few hours or days. The order in which the compound of formula (I) and the active ingredients described above are applied is not critical to carrying out the present invention.

[0287] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0288] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding it. These methods for preparing the compositions and the use of compound I for preparing these compositions are also the subject of the present invention.

[0289] The application methods for the compositions, i.e., spraying, atomizing, dusting, brushing, dusting, spreading, or pouring (which should be selected according to the intended purpose in the prevailing situation), are other subjects of the present invention. Typical concentration rates are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm, of active ingredient. The application rate per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g / ha, preferably 10 to 600 g / ha.

[0290] The preferred method of application in the field of crop protection is application to the foliage of plants (foliar application), and the frequency and rate of application can be selected according to the risk of infestation by the relevant pest. Alternatively, the active ingredient can reach the plant via the root system (systemic action) by irrigating the plant habitat with a liquid composition or by introducing the active ingredient in solid form into the plant habitat, for example, the soil, for example in the form of granules (soil application). In the case of paddy rice plants, such granules can be metered into the paddy field.

[0291] The compounds of formula (I) of the present invention and compositions thereof are also suitable for protecting plant propagation material, such as seeds or seedlings of fruits, tubers, or grains, from the above-mentioned types of pests. The propagation material can be treated with the compounds before planting, for example, seeds can be treated before sowing. Alternatively, the compounds can be applied to the seed kernels by immersing them in a liquid composition or by applying a layer of a solid composition (coating). When the propagation material is planted at the application site, the compositions can also be applied between the furrows, for example, during drilling. These treatment methods for plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typical treatment rates depend on the plant and the pests / fungi to be controlled and are generally 1 to 200 grams per 100 kg of seeds, preferably 5 to 150 grams per 100 kg of seeds (e.g., 10 to 100 grams per 100 kg of seeds).

[0292] The term seed encompasses all types of seeds and plant propagules, including but not limited to true seeds, seed pieces, suckers, kernels, bulbs, fruits, tubers, grains, rhizomes, cuttings, cuttings, etc., and in preferred embodiments refers to true seeds.

[0293] The present invention also includes seeds coated or treated with or containing a compound of formula I. The term "coated or treated with and / or containing" generally indicates that the active ingredient is most often on the surface of the seed upon application, but that depending on the application method, some of the ingredient may penetrate to varying degrees into the seed material. When the seed product is (re)planted, it may absorb the active ingredient. In one embodiment, the present invention makes available plant propagation material having a compound of formula I attached thereto. Furthermore, this makes available compositions comprising plant propagation material treated with a compound of formula I.

[0294] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. The seed treatment application of the compound of formula (I) can be carried out by any known method, such as by spraying or dusting the seeds before sowing or at the time of sowing / planting the seeds.

[0295] The compounds of the present invention can be distinguished from other similar compounds by their greater efficacy at low application rates and / or by different pest control, which can be achieved, if desired, at lower concentrations, e.g., 10 ppm, 5 ppm, 2 ppm, 1 ppm or 0.2 ppm; or 300, 200 or 100 mg AI / m 2 Higher efficacy can be observed by a person skilled in the art using experimental techniques using lower application rates, such as: Higher efficacy can be observed by a higher safety profile (improved physicochemical properties or higher biodegradability to above- and below-ground non-target organisms, such as fish, birds, and bees).

[0296] In each aspect and embodiment of the present invention, "consisting essentially of" and variations thereof is a preferred embodiment of "comprising" and variations thereof, and "consisting of" and variations thereof is a preferred embodiment of "consisting essentially of" and variations thereof.

[0297] The present disclosure makes available any and all combinations of the embodiments disclosed herein.

[0298] It should be noted that the disclosure herein with respect to compounds of Formula I applies equally to compounds of Formula Ia, Ib, and each of Tables 1-35.

[0299] Biological Examples: The following examples illustrate the invention. Certain compounds of the invention can be distinguished from known compounds by their high efficacy at low application rates, which can be verified by those skilled in the art using the experimental procedures outlined in the examples, using lower application rates, such as 50 ppm, 24 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm, if necessary.

[0300] Example B1: Diabrotica balteata (corn rootworm) Corn sprouts placed on agar layers in 24-well microtiter plates were treated by spraying with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the plates were infested with L2 larvae (6-10 per well). Four days after infestation, samples were evaluated for mortality and growth inhibition compared with untreated samples.

[0301] The following compounds provided at least 80% control in at least one of two categories (mortality or growth inhibition) at a rate of 200 ppm: P1.2, P2.1, P2.2, P2.5, P2-17, P3.4, P7.1, P8.1

[0302] Example B2: Euschistus heros (Neotropical Brown Stink Bug) Soybean leaves on agar in 24-well microtiter plates were sprayed with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the leaves were infested with N2 nymphs. Samples were evaluated for mortality and growth inhibition compared to untreated samples 5 days after infestation.

[0303] The following compounds provided at least 80% control in at least one of two categories (mortality or growth inhibition) at a rate of 200 ppm: P2.1, P8.1

[0304] Example B3: Plutella xylostella (Diamond back moth) Twenty-four well microtiter plates containing artificial diet were treated by pipette with test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, diamondback moth eggs were pipetted onto gel blotting paper through a plastic stencil, which sealed the plate. Samples were assessed for mortality and growth inhibition compared to untreated samples 8 days after infestation.

[0305] The following compounds provided at least 80% control in at least one of two categories (mortality or growth inhibition) at a rate of 200 ppm: P1.2, P1.15, P1.51, P2.1, P2.2, P2.5, P2.10, P2.15, P2.16, P5.1, P5.2, P5.3, P7.1, P8.1

[0306] Example B4: Myzus persicae (green peach aphid). Intrinsic activity Test compounds prepared from 10,000 ppm DMSO stock solutions were applied by pipette into 24-well microtiter plates and mixed with the sucrose solution. The plates were closed with stretched Parafilm. A plastic stencil with 24 holes was placed on the plate, and infested pea seedlings were placed directly on the Parafilm. The infested plates were closed with gel blotting paper and another plastic stencil, then inverted. Samples were evaluated for mortality 5 days after infestation.

[0307] The following compounds caused at least 80% mortality at a test dose of 12 ppm: P1.3, P1.4, P1.22, P1.26

[0308] Example B5: Tetranychus urticae (Tetranychus urticae): Feeding / contact activity Phaseolus vulgaris leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from a 10,000 ppm DMSO stock solution. After drying, the discs were infested with mite populations of various ages. Samples were assessed for mortality in the mixed population (mobile) 8 days after infestation.

[0309] The following compounds caused at least 80% mortality at an application rate of 200 ppm: P1.1、P1.2、P1.3、P1.4、P1.5、P1.6、P1.7、P1.8、P1.10、P1.11、P1.12、P1.13、P1.14、P1.15、P1.16、P1.17、P1.18、P1.19、P1.2 0、P1.21、P1.22、P1.23、P1.24、P1.25、P1.26、P1.27、P1.28、P1.29、P1.30、P1.31、P1.33、P1.34、P1.35、P1.36、P1.37、P1.39、 P1.40、P1.41、P1.42、P1.43、P1.44、P1.45、P1.46、P1.49、P1.50、P1.52、P2.1、P2.2、P2.3、P2.4、P2.5、P2.6、P2.7、P2.8、P2.9 、P2.10、P2.11、P2.12、P2.13、P2.17、P3.1、P3.2、P3.3、P3.4、P3.5、P3.6、P3.7、P3.8、P3.9、P4.1、P4.2、P5.2、P6.1、P7.1、P8.1

Claims

1. Compounds of formula (I) 【Chemical 1】 (In the formula, R 1 is CN, C(=S)NH 2 or C 1 ~C 6 haloalkyl; R 2 is H, OH, halogen, C 1 ~C 6 Alkoxy or C 1 ~C 6 haloalkoxy; R 3 is H, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Halocycloalkyl, C 1 ~C 6 Alkoxy, or C 1 ~C 6 haloalkoxy; R 4 is H, halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Halocycloalkyl, C 1 ~C 6 Alkoxy, or C 1 ~C 6 haloalkoxy; R 5 is phenyl, 1 to 3 substituents R 6 is phenyl substituted with; Q is a cyclic amine represented by formula IIa or a cyclic amine represented by formula IIb; 【Chemistry 2】 where the arrow indicates the bond to the carbonyl group; p 1 and p 2 are each 0, or p 1 and p 2 are each 1; q 1 is 1 or 2 and indicates the number of methylene groups; q 2 is 1 or 2 and indicates the number of methylene groups; X is hydrogen, hydroxyl, C 1 ~C 6 alkoxy, cyano or halogen; Y is cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxy-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfanyl-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfinyl-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfonyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkenylsulfanyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkenylsulfinyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkenylsulfonyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkynylsulfanyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkynylsulfinyl-C 1 ~C 6 Alkyl, C 3 ~C 6 Alkynylsulfonyl-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkoxycarbonylamino, R a R b NC(O), R c C(O)NR d , R e SO 2 NR f , R g O-N=CR h , a 4-6 membered non-aromatic heterocyclic ring system in which one or two carbons are independently replaced by nitrogen, oxygen, sulfur, or sulfonyl, phenyl, one to three substituents R 8 phenyl, 5- or 6-membered monocyclic heteroaryl, or 1 to 3 substituents R 9 is a 5- or 6-membered monocyclic heteroaryl substituted with X and Y together form the group R m forming a double bond to the nitrogen substituted with O; A is cyano, C is 1 ~C 6 Cyanoalkyl, C 2 ~C 6 Cyanoalkenyl, C 3 ~C 6 Cyanocycloalkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Haloalkenyl, C 3 ~C 6 Halocycloalkyl, C 1 ~C 6 Alkoxy-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkoxycarbonyl, C 2 ~C 6 Alkenyloxycarbonyl, C 2 ~C 6 Alkynyloxycarbonyl, C 1 ~C 6 Alkylsulfanyl-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfinyl-C 1 ~C 6 Alkyl, C 1 ~C 6 Alkylsulfonyl-C 1 ~C 6 Alkyl, R i SO 2 , R j R k NSO 2 , phenyl, 1 to 3 substituents R 10 phenyl, heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic), or 1-3 substituents R 11 heteroaryl (either 5- or 6-membered monocyclic or 9- or 10-membered bicyclic) substituted with R a and R b are independently hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl and C 3 ~C 6 Halocycloalkyl and C 1 ~C 6 alkylsulfonyl; R c and R d are independently hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl and C 3 ~C 6 halocycloalkyl; R f is hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl or C 3 ~C 6 halocycloalkyl; R e and R i are independently 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl and C 3 ~C 6 halocycloalkyl; R g and R h are independently hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl and C 3 ~C 6 halocycloalkyl; R j and R k are independently hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl and C 3 ~C 6 halocycloalkyl; R m is hydrogen, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl or C 3 ~C 6 halocycloalkyl; R 6 , R 8 , R 9 , R 10 , R 11 are independently halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 2 ~C 6 Alkenyl, C 2 ~C 6 Haloalkenyl, C 2 ~C 6 Alkynyl, C 2 ~C 6 Haloalkynyl, C 3 ~C 6 Cycloalkyl, C 3 ~C 6 Halocycloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkylsulfonyl and C 1 ~C 6 haloalkylsulfanyl); or the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of said compounds of formula I.

2. R 3 is methyl, methoxy, ethoxy, difluoromethyl, or trifluoromethyl.

3. R 1 is CN or C(=S)NH 2 3. The compound of claim 1 or claim 2, wherein:

4. R 2 is hydrogen, and R 4 The compound according to any one of claims 1 to 3, wherein is hydrogen or cyano.

5. R 6 are independently halogen, cyano, C 1 ~C 3 Alkyl, C 1 ~C 3 Haloalkyl, C 1 ~C 3 Alkoxy; C 1 ~C 3 Haloalkoxy, C 1 ~C 3 Alkylsulfonyl and C 1 ~C 3 The compound according to any one of claims 1 to 4, selected from haloalkylsulfanyl.

6. Q is of formula IIa, where X is hydrogen or hydroxyl; Y is C 1 ~C 3 Alkylsulfanyl-methyl, C 1 ~C 3 Alkylsulfinyl-methyl, C 1 ~C 3 Alkylsulfonyl-methyl, C 3 ~C 4 Alkenylsulfanyl-methyl, C 3 ~C 4 Alkenylsulfinyl-methyl, C 3 ~C 4 Alkenylsulfonyl-methyl, C 3 ~C 4 Alkynylsulfanyl-methyl, C 3 ~C 4 Alkynylsulfinyl-methyl, C 3 ~C 4 6. The compound of any one of claims 1 to 5, which is alkynylsulfonyl-methyl, methanesulfonylamido, ethanesulfonylamido, 1,1-dioxo-1,2-thioazolidin-2-yl, 1,2,4-oxadiazol-3-yl, 2-pyridyl, substituted 2-pyridyl, or substituted 1,2,4-oxadiazol-3-yl, where each substituent is 1 to 3 substituents independently selected from chlorine and methyl; or X and Y together form a double bond to nitrogen substituted with methoxy or ethoxy.

7. q 1 and q 2 6. The compound according to any one of claims 1, 3, 4 and 5, wherein each of

8. Q is of formula IIb, where A is cyano, C 1 ~C 3 Cyanoalkyl, C 1 ~C 3 Haloalkyl, C 2 ~C 3 Haloalkenyl, C 1 ~C 3 Alkoxy-C 1 ~C 3 Alkyl, C 1 ~C 3 Alkoxycarbonyl, C 1 ~C 3 Alkylsulfanyl-C 1 ~C 3 Alkyl, C 1 ~C 3 Alkylsulfinyl-C 1 ~C 3 Alkyl, R i SO 2 or a 6-membered monocyclic heteroaryl substituted with 1 to 3 substituents independently selected from fluorine and chlorine.

9. A composition comprising a compound according to any one of claims 1 to 8, one or more auxiliaries and diluents, and optionally one or more other active ingredients.

10. 10. A method for combating and controlling insects, acaridae, nematodes or molluscs, which method comprises applying to the pest, the pest's habitat or plants susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of a compound according to any one of claims 1 to 8 or a composition according to claim 9.

11. 10. A method for the protection of plant propagation material from attack by insects, mites, nematodes or mollusks, which method comprises treating the propagation material or the locus in which the propagation material is planted with an effective amount of a compound according to any one of claims 1 to 8 or a composition according to claim 9.

12. 10. Plant propagation material comprising or having attached thereto a compound according to any one of claims 1 to 8 or a composition according to claim 9.

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