Novel bicyclic carboxamide compounds useful as pesticides.

Abstract

Formula (I) JPEG2026500298000126.jpg36160 (wherein the substituents are as defined in claim 1) The compounds of formula (I) and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers or N-oxides of these compounds can be used as insecticides.

Description

[Technical Field]

[0001] The present invention relates to pesticidally active, especially insecticidally active, bicyclic carboxamide or thioamide compounds, preferably substituted bicyclic carboxamide compounds thereof, processes for their preparation, compositions containing these compounds and their use for controlling animal pests, including arthropods, especially insects. [Background technology]

[0002] WO 2021 / 153720 describes certain alkoxybenzoic acid amide derivatives. Summary of the Invention [Means for solving the problem]

[0003] It has now been discovered that certain novel pesticidally active bicyclic carboxamide or thioamide compounds.

[0004] Thus, in a first aspect, the present invention provides a compound of formula (I) [ka] (In the formula, A is O or S; X is -CH2- or -CH2CH2-, R 1is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C1-C4-alkoxy-C1-C6-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-cycloalkyl, N-C1-C4 alkoxy-imidoyl, N-C1-C4-alkoxy-C1-C4-alkyl-imidoyl, C4-C8-bis(2-methyl- ... and wherein any of said 3, 4, 5 or 6-membered heterocycloalkyl contains one or two heteroatoms or groups individually selected from N, O, S, S=O or SO2, provided that not more than one is O, S, S=O or SO2; and wherein said phenyl, phenyl-C1-C6-alkyl, 5 or 6-membered heteroaryl and any of the 5- or 6-membered heteroaryl-C1-C3-alkyl contains 1 or 2 heteroatoms independently selected from N or O; any of the 3-, 4-, 5-, or 6-membered heterocycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl; any of the phenyl and 5- or 6-membered heteroaryl is unsubstituted or substituted with halogen, cyano, substituted by one, two or three substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy, any of said C3-C6-cycloalkyl being unsubstituted or substituted by one, two or three substituents independently selected from cyano, halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl or C1-C4-alkylaminocarbonyl; or R1 is the formula (W) [ka] (wherein the wavy line represents the position of the bond to the nitrogen of the amide group of the compound of formula (I), Y is selected from O, carbonyl, or C1-C2 alkyl, and R 8 is selected from hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-halocycloalkyl, C1-C6-alkoxy-C1-C3-alkyl or phenyl, wherein the phenyl is unsubstituted or substituted by one or two substituents independently selected from halogen or C1-C3-alkyl. is selected from the heterocycles R 2 is selected from hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl, R 3 is selected from hydrogen, halogen or C1-C3-alkyl, R 4 is selected from hydrogen, halogen or C1-C3-alkyl, R 5 is selected from hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl, R 6 is selected from hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxyC1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl, and R 7 is selected from C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, wherein the cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from halogen, cyano, C1-C3-alkyl or C1-C3-haloalkyl) or a salt or N-oxide thereof.

[0005] Surprisingly, it has been found that the novel compounds of formula (I) exhibit advantageous levels of biological activity or excellent properties for practical use as agrochemical active ingredients for protecting plants from insects, such as higher biological activity, advantageous activity spectrum, improved safety profile against above- and below-ground non-target organisms (fish, birds, bees, etc.), improved physicochemical properties, or improved biodegradability. Particularly surprisingly, it has been found that certain compounds of formula (I) can exhibit advantageous safety profiles against non-target arthropods, particularly honeybees, solitary bees, and bumblebees. Most specifically, this is the European honeybee (Apis mellifera).

[0006] According to a second aspect of the present invention there is provided a composition comprising a compound of formula (I) as defined in the first aspect. Such a composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0007] According to a third aspect of the present invention there is provided a method for the control and extermination of insects, mites, nematodes or molluscs which method comprises applying to the pest, the pest's habitat or plants which are 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.

[0008] According to a fourth aspect of the present invention there is provided a method of protecting plant propagation material from attack by insects, mites, nematodes or mollusks, the method comprising treating the propagation material or the locus where the propagation material is to be 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.

[0009] According to a fifth aspect, the present invention provides plant propagation material, such as seed, comprising, treated with or having attached thereto a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect. DETAILED DESCRIPTION OF THE INVENTION

[0010] The compounds of formula (I) having at least one basic centre may, 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, or strong organic carboxylic acids, for example C1-C4 alkanecarboxylic acids which are unsubstituted or substituted, for example by halogens, such as acetic acid, for example saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, for example 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. Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example mineral salts such as 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.

[0011] 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 useful salt form.

[0012] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds, as described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).

[0013] The compounds of formula (I) according to the invention also include the hydrates which may be formed during the formation of salts.

[0014] When substituents are described as being "optionally substituted," this means that they may be substituted with one or more of the same or different substituents, for example, one, two, or three R x It means that it may or may not have a substituent. For example, C1-C6 alkyl substituted with 1, 2, or 3 halogens includes, but is not limited to, -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3, or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2, or 3 halogens includes, but is not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CHO-, or CH3CF2O- groups. The term "optionally substituted" can be used interchangeably with the terms "optionally substituted" or "unsubstituted or substituted with...".

[0015] As used herein, the term "halogen" or "halo" means fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine. This also applies to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy and halocycloalkyl.

[0016] As used herein, amino refers to the group —NH 2 .

[0017] As used herein, cyano refers to a -CN group.

[0018] As used herein, the term "hydroxyl" or "hydroxy" refers to an --OH group.

[0019] As used herein, the term "carboxylic acid" refers to a -COOH group.

[0020] As used herein, "C1-C n The term "-alkyl" refers to a saturated linear or branched hydrocarbon group having 1 to n carbon atoms and bonded via any carbon atom, such as any one of methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

[0021] As used herein, "C2-C n The term "-alkenyl" refers to a straight or branched alkenyl chain moiety having 2 to n carbon atoms and one or two double bonds, for example ethenyl, prop-1-enyl, but-2-enyl.

[0022] As used herein, "C2-C n The term "-alkynyl" refers to a straight or branched alkynyl chain moiety having 2 to n carbon atoms and one triple bond, for example ethynyl, prop-2-ynyl, but-3-ynyl.

[0023] As used herein, "C1-C n The term "alkylsulfonyl" refers to a group of the formula -S(O)R a (In the formula, R a are the C1 to C2 defined generally above. n It refers to the group (which is an alkyl group).

[0024] As used herein, "C1-C n-Alkylsulfonyl-C1-C n The term "-alkyl" refers to C1-C n -refers to an alkyl group (as defined above) substituted with an alkylsulfonyl group.

[0025] As used herein, "C3-C n The term "cycloalkyl" refers to 3 to n-membered cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0026] As used herein, "C1-C n The term "C2-C alkoxy" refers to any one of the linear or branched saturated alkyl groups (as described above) having 1 to n carbon atoms attached through an oxygen atom, i.e., for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy. As used herein, "C2-C n The term "-alkenyloxy" refers to a straight or branched alkenyl chain (as described above) having 1 to n carbon atoms attached through an oxygen atom.

[0027] As used herein, "C1-C n -Alkoxy-C1~C n The term "-alkyl" refers to C1-C n -refers to an alkyl group (as defined above) substituted with an alkoxy group, examples of which are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.

[0028] As used herein, "C3-C n -Cycloalkyl-C1-C n The term "-alkyl" refers to C3 to C n - refers to an alkyl group (as described above) substituted with a cycloalkyl group. Examples are cyclopropylmethyl and cyclopropylethyl. Similarly, "C3-C n -Halocycloalkyl-C1-C nThe term "-alkyl" refers to an alkyl group substituted with a cycloalkyl group, where the cycloalkyl group is substituted with one or more of the same or different halogen atoms. Examples are 3,3-difluorobutylmethyl and 1-chlorocyclopropylmethyl.

[0029] As used herein, "C4-C n The term "-bicycloalkyl" refers to a cyclic, non-aromatic, bicyclic ring system containing two rings fused together (i.e., sharing two carbon atoms) and consisting solely of carbon and hydrogen atoms. Examples include bicyclo[1.1.1]pentanyl, bicyclo[3.1.0]hexan-6-yl, bicyclo[4.1.0]heptan-7-yl, bicyclo[3.2.0]heptan-6-yl, bicyclo[3.2.0]heptan-3-yl, octahydro-2-pentalenyl, and octahydro-1-pentalenyl.

[0030] As used herein, the term "heterocycloalkyl" or "heterocyclyl" refers to a stable 3-, 4-, 5-, or 6-membered non-aromatic monocyclic ring group containing one, two, or three heteroatoms / groups individually selected from nitrogen, oxygen, sulfur, S=O, and SO. Heterocyclyl groups can be attached to the remainder of the molecule through a carbon atom or a heteroatom. Examples of heterocyclyls include, but are not limited to, epoxide, aziridinyl, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dioxolanyl, morpholinyl, oxazinanyl, oxetanyl, 1,1-dioxothietan-3-yl, or δ-lactamyl. Heterocycloalkyl groups can be substituted on the heteroatoms and / or carbon atoms. The term "cyanoheterocycloalkyl" refers to a carbon atom on a heterocycloalkyl group being substituted with a cyano group.

[0031] As used herein, "cyano-C1-C nThe term "-alkyl" refers to a C1-C2 alkyl group having 1 to n carbon atoms in which one of the hydrogen atoms of the group is replaced by a cyano group. n -alkyl groups (as defined above), such as cyano-methyl, 2-cyano-ethyl, 2-cyano-propyl, 3-cyano-propyl, 1-(cyano-methyl)-2-ethyl, 1-(methyl)-2-cyano-ethyl, 4-cyanobutyl, etc. Similarly, "cyano-C3-C n The term "cycloalkyl" refers to a C3-C6 alkyl group in which one of the hydrogen atoms is replaced by a cyano group. n -cycloalkyl group, "cyano-C3-C n -Cycloalkyl-C1-C n The term "-alkyl" refers to cyano-C3-C n -C1-C with cycloalkyl group n -refers to alkyl groups.

[0032] As used herein, "C1-C nThe term "haloalkyl" refers to a linear or branched saturated alkyl group (as defined above) having 1 to n carbon atoms and bonded via any of the carbon atoms, in which some or all of the hydrogen atoms of these groups may be substituted 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, 2, It refers to any one of 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. Thus, the term "C1-C2 fluoroalkyl" refers to any one of a C1-C2 alkyl group having 1, 2, 3, 4 or 5 fluorine atoms, such as 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 a C-C alkyl group substituted with one or more halo atoms, each of which may be the same or different. n -alkenyl or C2-C nSimilarly, as used herein, "C3-C" refers to an -alkynyl group. n -halocycloalkyl" or "C1-C n The term "haloalkoxy" refers to a C-C alkyl group substituted with one or more halo atoms, each of which may be the same or different. n -cycloalkyl group or C1-C n -refers to an alkoxyl group.

[0033] As used herein, "C1-C n The term "-alkylcarbonyl" refers to a C1-C alkyl group bonded through the carbon atom of a carbonyl (C=O) group. n -refers to alkyl groups.

[0034] As used herein, "C1-C n The term "-alkoxycarbonyl" refers to a C1-C alkoxycarbonyl bonded through the carbon atom of a carbonyl (or C=O) group. n -refers to the alkoxy moiety.

[0035] As used herein, "phenyl-C1-C n The term "-alkyl" refers to a C1-C6 alkyl group substituted with a phenyl ring. n - refers to an alkyl group. Examples include benzyl. Phenyl-C1-C n The alkyl group may be substituted with an alkyl group and / or a phenyl group.

[0036] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl. "Heteroaryl-C1-C n -alkyl" or "heteroaryl-C3-C nThe term "-cycloalkyl" refers to a C1-C6 alkyl group substituted with a heteroaryl group. n -Alkyl or C3-C n - refers to a cycloalkyl group. This heteroaryl-C1-C n -Alkyl or heteroaryl-C3-C n The heteroaryl, alkyl and / or cycloalkyl groups of the cycloalkyl group may be optionally substituted.

[0037] As used herein, the term "control" refers to reducing the number of pests so that damage to plants or plant-derived products is reduced, eliminating pests, and / or preventing further pest damage.

[0038] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, the storage of plant-derived products (such as fruit, grain, and timber), and pests associated with damage to man-made structures. The term pest includes all stages of the pest life cycle.

[0039] As used herein, the term "effective amount" refers to an amount of a compound or a salt thereof that produces a desired effect upon single or multiple applications.

[0040] Effective amounts are readily determined by those skilled in the art using known techniques and by observing results obtained under similar circumstances. Many factors are considered in determining an effective amount, including, but not limited to, the type of plant or plant-derived product to be applied, the pest to be controlled and its life cycle, the particular compound to be applied, the type of application, and other relevant circumstances.

[0041] As used herein, the terms "room temperature," or "RT," or "rt," or "ambient temperature" refer to a temperature of about 15° C. to about 35° C. For example, rt can refer to a temperature of about 20° C. to about 30° C.

[0042] The following list provides the substituents R for the compounds of formula (I) of the present invention: 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , A, W, and X. Any definition given below for any one of these substituents may be combined with any definition of any other substituent given below or elsewhere in this specification.

[0043] In one embodiment of the invention, X is selected from -CH2- or -CH2CH2-. In one embodiment, it is -CH2-. In another embodiment, X is -CH2CH2-.

[0044] In one embodiment of the invention, A is selected from O or S. In one embodiment, A is O. In another embodiment, A is S. Preferably, A is O.

[0045] In one embodiment of the present invention, R 1is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, cyano-C1-C6-alkyl, C1-C4-alkoxy-C1-C6-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-cycloalkyl, N-C1-C4 alkoxy-imidoyl, N-C1-C4-alkoxy-C1-C4-alkyl-imidoyl, C4-C8-bis(2-methyl- ... and wherein any of said 3, 4, 5 or 6-membered heterocycloalkyl contains one or two heteroatoms or groups individually selected from N, O, S, S=O or SO2, provided that not more than one is O, S, S=O or SO2; and wherein said phenyl, phenyl-C1-C6-alkyl, 5 or 6-membered heteroaryl and any of the 5- or 6-membered heteroaryl-C1-C3-alkyl contains 1 or 2 heteroatoms independently selected from N or O; any of the 3-, 4-, 5-, or 6-membered heterocycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl; any of the phenyl and 5- or 6-membered heteroaryl is unsubstituted or substituted with halogen, cyano, substituted by one, two or three substituents independently selected from C1-C4 alkyl, C1-C4 haloalkyl or C1-C4 alkoxy, any of said C3-C6-cycloalkyl being unsubstituted or substituted by one, two or three substituents independently selected from cyano, halogen, C1-C4-alkyl, C1-C3-haloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl or C1-C4-alkylaminocarbonyl; or R 1 is the formula (W) [ka] (wherein the wavy line represents the position of the bond to the nitrogen of the amide group of the compound of formula (I), Y is selected from O, carbonyl, or C1-C2 alkyl, and R 8 is selected from hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-halocycloalkyl, C1-C6-alkoxy-C1-C3-alkyl or phenyl, wherein the phenyl is unsubstituted or substituted by one or two substituents independently selected from halogen or C1-C3-alkyl. is selected from the heterocycles

[0046] Preferably, in one embodiment of the present invention, R 1 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C3-alkoxy, C3-C6-cycloalkyl, cyano-C1-C4-alkyl, C1-C3-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl, N—C1-C4 alkoxy-imidoyl or C4-C6-bicycloalkyl, any of the C3-C6-cycloalkyl being unsubstituted or substituted by one or two substituents independently selected from cyano, halogen, C1-C4-alkyl, C1-C2-haloalkyl, C1-C3 alkoxycarbonyl, C1-C3 alkylcarbonyl or C1-C3 alkylaminocarbonyl, or R 1 is the formula (W) [ka] (wherein the wavy line represents the position of attachment to the N atom of the amide group of the compound of formula (I), and Y is selected from O, carbonyl, or CH2). Preferably, Y is selected from carbonyl or CH2, and R 8is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-halocycloalkyl, C1-C6-alkoxy-C1-C3-alkyl or phenyl, wherein said phenyl may be substituted by one or two substituents independently selected from halogen or C1-C3-alkyl. In one embodiment of the present invention, R 8 is selected from the group consisting of hydrogen, C1-C3-alkyl, C3-C6-cycloalkyl or C1-C3-haloalkyl. 8 is selected from hydrogen, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl. More preferably, R 8 is selected from hydrogen, methyl, trifluoromethyl or 2,2,2-trifluoroethyl.

[0047] Preferably, R 1 is selected from hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C2-alkoxy, C3-C6-cycloalkyl, cyano-C1-C4-alkyl, C1-C3-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C4-alkyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, and C4-C6-bicycloalkyl, any of the C3-C6-cycloalkyl being unsubstituted or substituted by one or two substituents independently selected from cyano, halogen, methyl, ethyl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, acetyl, methoxycarbonyl, and methylaminocarbonyl. More preferably, R 1 is selected from hydrogen, C1-C4-alkyl, C1-C2-alkoxyC1-C4-haloalkyl, C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl or C4-C6-bicycloalkyl. More preferably, R 1 is selected from trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, cyclopropyl, cyanocyclopropyl or bicyclo[1.1.1]pentanyl.

[0048] In other embodiments, R 1 is the formula (W) [ka] (wherein the wavy line represents the position of attachment to the N atom of the amide group of the compound of formula (I), and Y is selected from O, carbonyl, or CH2). Preferably, Y is selected from carbonyl or CH2, and R 8 is selected from the group consisting of hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-halocycloalkyl, C1-C6-alkoxy-C1-C3-alkyl or phenyl, wherein said phenyl may be substituted by one or two substituents independently selected from halogen or C1-C3-alkyl. In one embodiment of the present invention, R 8 is selected from hydrogen, C1-C3-alkyl, C3-C6-cycloalkyl or C1-C3-haloalkyl. 8 is selected from hydrogen, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl. More preferably, R 8 is selected from hydrogen, methyl, trifluoromethyl or 2,2,2-trifluoroethyl.

[0049] In one embodiment of the present invention, R 2 is selected from hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl. 2 is hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl. More preferably, R 2 is hydrogen, methyl, ethyl, methoxycarbonyl or methylcarbonyl. More preferably, R 2 is hydrogen or methyl. Most preferably, R2 is hydrogen.

[0050] In one embodiment of the present invention, R 3 is selected from hydrogen, halogen or C1-C3-alkyl. 3 is hydrogen, halogen, methyl or ethyl. More preferably, R 3 is hydrogen, chloro or methyl. Even more preferably, R 3 is hydrogen or methyl. In one embodiment of the present invention, R 3 is hydrogen. In another embodiment of the present invention, R 3 is methyl.

[0051] In one embodiment of the present invention, R 4 is selected from hydrogen, halogen or C1-C3-alkyl. 4 is hydrogen, methyl, ethyl or halogen. More preferably, R 4 is hydrogen or methyl. More preferably, R 4 is hydrogen.

[0052] In one embodiment of the present invention, R 5 is selected from hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl. Preferably, R 5 is hydrogen, methyl, ethyl or cyclopropyl. More preferably, R 5 is hydrogen, methyl or ethyl. More preferably, R 5 is hydrogen or methyl. In one embodiment of the present invention, R 5 is hydrogen. In another embodiment of the present invention, R 5 is methyl.

[0053] In one embodiment of the present invention, R 6is selected from hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxyC1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl. 6 is selected from hydrogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkoxyC1-C4-alkyl, cyano-C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl. Preferably, R 6 is hydrogen, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylcarbonyl or C1-C4-alkoxycarbonyl. More preferably, R 6 is hydrogen, C1-C4-alkyl, C1-C2-alkoxy or C1-C2-alkoxy-C1-C4-alkyl. Most preferably, R 6 is hydrogen, methyl or ethyl. More preferably, R 6 is hydrogen or methyl. In one embodiment of the present invention, R 6 is hydrogen. In another embodiment of the present invention, R 6 is methyl. Most preferably, R 6 is hydrogen.

[0054] In one embodiment of the present invention, R 7 is selected from C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, wherein the cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from halogen, cyano, C1-C3-alkyl or C1-C3-haloalkyl.

[0055] In another embodiment of the present invention, R 7is selected from C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, wherein the cycloalkyl is unsubstituted or substituted by one or two substituents independently selected from halogen, cyano or methyl. Preferably, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, wherein the cycloalkyl is unsubstituted or substituted by one substituent selected from cyano. More preferably, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl. More preferably, R 7 is trifluoromethylsulfonylamino.

[0056] More preferably, R 7 teeth, [ka] (wherein the wavy line represents the position bonded to the nitrogen) is.

[0057] More preferably, R 7 teeth, [ka] (wherein the wavy line represents the position bonded to the nitrogen) is.

[0058] Most preferably, R 7 teeth, [ka] (wherein the wavy line represents the position bonded to the nitrogen) is.

[0059] Thus, the present invention provides a compound having the formula R as defined above. 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 Compounds of formula (I) having any combination / configuration of A, W and X are provided.

[0060] Embodiments according to the present invention are provided as described below.

[0061] In one embodiment, the compound of formula (I) has formula (IA) or (IB): [ka] (In the formula, X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for compounds of formula (I) The compound may be represented by:

[0062] In one embodiment, the compound of formula (I) has formula (IA), where X is —CH— and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for compounds of formula (I).

[0063] In other embodiments, the compound of formula (I) has formula (IA), where X is —CHCH— and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for compounds of formula (I).

[0064] In a further aspect, the compound of formula (I) has formula (IB) where X is —CH— and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for compounds of formula (I).

[0065] In other further embodiments, the compound of formula (I) has formula (IB) where X is —CHCH— and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is as defined for compounds of formula (I).

[0066] In one embodiment, in the compounds of formula (IA) or (IB) according to the present invention, X is -CH2- or -CH2CH2-, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, R 1 and R 2 is as defined for compounds of formula (I).

[0067] In one embodiment, in the compounds of formula (IA) or (IB) according to the present invention, X is -CH2- or -CH2CH2-, R2 is hydrogen, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, R 1 is as defined for compounds of formula (I).

[0068] In one embodiment, in the compounds of formula (IA) or (IB) according to the present invention, X is -CH2-, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, R 1 and R 2 is as defined for compounds of formula (I).

[0069] In one embodiment, in the compounds of formula (IA) or (IB) according to the present invention, X is -CHCH-, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4 alkyl, C1-C4 alkoxy-C1-C4-alkyl, R 7 is C1-C3-alkylsulfonyl, C1-C3-haloalkylsulfonyl or C3-C6-cycloalkylsulfonyl, R 1 and R 2 is as defined for compounds of formula (I).

[0070] In one embodiment of the present invention, the compound of formula (IA) has the formula (I-A1) [ka] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is as defined for the compounds of formula (I) according to the invention, and R 9 is selected from the group consisting of C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cyanocycloalkyl or C3-C6-cycloalkyl The compound may be:

[0071] In one embodiment of the present invention, R 9 is trifluoromethyl, difluoromethyl, cyclopropyl, cyanocyclopropyl, isopropyl. Preferably, R 9 is trifluoromethyl, difluoromethyl, cyclopropyl.

[0072] R 4 The compounds of formula (I-A1) of the present invention, where R is not hydrogen, have at least two asymmetric carbon atoms. 1 , R 2 , R 3 , R 4 , R 5 and R 6 is as defined for formula (I), and R9 It is well recognized that diastereomers and enantiomers of the compounds of formula (I-A1) are as defined above for the compounds of formula (I-A1) are also included within the scope of the present invention.

[0073] In one embodiment of the present invention, a compound of formula (I-A1), wherein X is —CH— or —CHCH—, and R 4 is hydrogen) are (S)-enantiomers. In another embodiment of the present invention, the compound represented by formula (I-A1) (wherein X is -CH- or -CHCH- and R 4 is hydrogen) are the (R)-enantiomers. In yet another embodiment, the compound represented by formula (I-A1) (wherein X is -CH- or -CHCH- and R 4 is hydrogen) is a mixture of the (S) or (R) enantiomers. Preferably, the compound represented by formula (I-A1) (wherein X is -CH2- or -CH2CH2- and R 4 The compound represented by (wherein is hydrogen) is the (S)-enantiomer.

[0074] In one embodiment, in the compound of formula (I-A1) of the present invention, X is -CH2- or -CH2CH2-, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxyC1-C4-alkyl, R 9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cyanocycloalkyl or C3-C6-cycloalkyl, R 1 and R 2 is as defined for compounds of formula (I).

[0075] In one embodiment, in the compound of formula (I-A1) of the present invention, X is -CH2- or -CH2CH2-, R 2 is hydrogen, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl, R 9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cyanocycloalkyl or C3-C6-cycloalkyl, R 1 is as defined for compounds of formula (I).

[0076] In one embodiment, in the compound of formula (I-A1) of the present invention, X is -CH2- or -CH2CH2-, R 2 is hydrogen, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl, R 9 is trifluoromethyl, difluoromethyl or cyclopropyl, R 1 is as defined for compounds of formula (I).

[0077] In one embodiment of the present invention, the compound of formula (IA) is R 1 is selected from heterocycle W, formula (I-A2): [ka] (In the formula, Y, X, R 8 , R 2 , R 3 , R 4 , R 5 , R 6 is as defined for the compounds of formula (I) according to the invention, and R 9 is selected from C1-C4-alkyl, C1-C4-haloalkyl, C3-C4 cyanocycloalkyl or C3-C6-cycloalkyl R 4 The compounds of the present invention of formula (I-A2) where Y, X, R are not hydrogen have at least two asymmetric carbon atoms. 8 , R 2 , R 3 , R 4 , R 5 , R 6 is as defined for formula (I), and R 9 It is well recognized that diastereomers and enantiomers of (I-A1) are as defined for compounds of formula (I-A2)) are also included within the scope of the present invention.

[0078] In one embodiment of the present invention, a compound of formula (I-A2), wherein X is N or CH, and R 4 is hydrogen) are (S)-enantiomers. In another embodiment of the present invention, the compound represented by formula (I-A2) (wherein X is N or CH and R 4 is hydrogen) are (R)-enantiomers. In yet another embodiment, the compound represented by formula (I-A2) (wherein X is N or CH and R 4 is hydrogen) is a mixture of (S) or (R) enantiomers. Preferably, the compound represented by formula (I-A2) (wherein X is N or CH and R 4 The compound represented by (wherein is hydrogen) is the (S)-enantiomer.

[0079] In one embodiment, in the compound of formula (I-A2) of the present invention, X is -CH2- or -CH2CH2-, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxyC1-C4-alkyl, R 9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cyanocycloalkyl or C3-C6-cycloalkyl, R 2 , R 8 and Y are as defined for compounds of formula (I).

[0080] In one embodiment, in the compound of formula (I-A1) of the present invention, X is -CH2- or -CH2CH2-, R 2 is hydrogen, R 3 is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxyC1-C4-alkyl, R 9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cyanocycloalkyl or C3-C6-cycloalkyl, R 8 and Y are as defined for compounds of formula (I).

[0081] In one embodiment, in the compound of formula (I-A1) of the present invention, X is -CH2- or -CH2CH2-, R 2 is hydrogen, R 3is hydrogen or methyl, R 4 is hydrogen, R 5 is hydrogen, methyl or ethyl, R 6 is hydrogen, C1-C4-alkyl or C1-C4-alkoxyC1-C4-alkyl, R 9 is trifluoromethyl, difluoromethyl or cyclopropyl, R 8 and Y are as defined for compounds of formula (I).

[0082] The possible presence of one or more asymmetric carbon atoms in any of the compounds selected from compounds of formula (I), (IA), (I-A1) or (I-A2) according to the present invention or in compounds selected from compounds set out in Tables A1 to A4 or in Table P (below) means that chiral isomeric forms, i.e. enantiomeric or diastereomeric forms, of the compounds may exist.

[0083] In one embodiment, the compound of formula (I) according to the present invention is selected from the compounds set forth in any one of Tables A1 to A4.

[0084] In other embodiments, compounds of formula (I) according to the present invention are selected from the compounds set forth in Table P (below).

[0085] Preferably, the compound according to formula (I) is selected from compounds P-1 to P-9 set forth in Table P (below).

[0086] 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 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 formula (I) as defined in the first aspect. The present invention further provides a method of preventing and / or treating ectoparasite-borne diseases, the method comprising administering an effective amount of a compound of formula (I) as defined in the first aspect to an animal in need thereof.

[0087] The compounds of formula (I) can be prepared according to methods known to those skilled in the art. More specifically, the compounds of formula I and intermediates thereto can be prepared as described below in the schemes and examples. Specific asymmetric centers have been left unidentified for clarity and are not intended to limit the teachings of the schemes in any way.

[0088] The compound of formula (I) according to the present invention (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I)), can be prepared by reacting a compound of formula (II) (wherein R 3 , R 5 , R 4 , R 6 , R 7 and X are as defined for formula (I)) via an intermediate acid chloride or an activated acylating agent to a compound of formula (III) (wherein R 1 and R 2 can be obtained by conversion with a compound of formula (I) as defined above, as shown in Scheme 1 below. Scheme 1 [ka]

[0089] As shown in Scheme 1, compound II is activated to a compound of formula IV by methods known to those skilled in the art, such as those described in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula IV (wherein G is a halogen) is formed by treating a compound of formula II with, for example, oxalyl chloride or thionyl chloride in an inert solvent such as dichloromethane (DCM) or tetrahydrofuran (THF) in the presence of a catalytic amount of dimethylformamide (DMF) at a temperature between 25 and 170° C., preferably between 25 and 80° C. Treatment of IV with a compound of formula III, optionally in the presence of a base such as triethylamine or pyridine, provides a compound of formula I. Alternatively, compounds of formula I can be prepared by treating compounds of formula II with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at temperatures between room temperature and 180° C. to give activated species IV (where G is G1 or G2). Furthermore, compounds of formula IV (where G is G3 and G4) can also be obtained by activating the acid of formula II by reaction with a coupling agent such as propanephosphonic anhydride (T3P®) or O-(7-aza-1-benzotriazolyl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt Chem. 1998, 340, 581. Subsequent reaction with an amine of formula III provides a compound of formula I.

[0090] Formula (II) (wherein, R 3 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I)) can be prepared by reacting a compound of formula (V) 3 , R 4 , R 5 , R 6, R 7 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl) in the presence of a base or acid, as shown in Scheme 2 below. Scheme 2 [ka]

[0091] As shown in Scheme 2, compound (V) can be hydrolyzed under basic conditions to give compound (II) by methods known to those skilled in the art, such as those described in Org. Biomol. Chem. 2014, 2049, WO 2006088716, WO 2000034243, and WO 2002055480. For example, this reaction can be carried out in water or in an organic solvent, such as methanol, ethanol, THF, or DCM, or in a mixture, in the presence of a base such as lithium hydroxide, sodium hydroxide, or potassium hydroxide. Alternatively, compound (V) can be converted to compound (II) under acidic conditions by methods known to those skilled in the art, such as those described in Monatsh. Chem. 1985, 661; WO 2015164374. For example, this reaction can be carried out in water or in a mixture of water and an organic solvent, such as methanol, THF, or dioxane, in the presence of trifluoroacetic acid, hydrochloric acid, or sulfuric acid.

[0092] Formula (Vb) (where R 3 , R 4 , R 5 , R 7 and X are as defined for formula (I), and R 12 is C1-C6 alkyl) can be obtained by the compound of formula (VI) 3 , R 4 , R 5 and X are as defined for formula (I), and R 12 is C1-C6 alkyl) to a compound of formula (VII) 7can be obtained by conversion in the presence of a reagent of formula (I), where G is a halogen or an activating group of formula G5, as shown in Scheme 3 below. Scheme 3 [ka]

[0093] As shown in Scheme 3, compound (VI) can be converted to compound (Vb) by methods known to those skilled in the art, such as those described in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021153720; and WO 2010150192. For example, this reaction can be carried out in an inert organic solvent such as DCM, dioxane, or THF in the presence of a base such as triethylamine, pyridine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. Alternatively, as known to those skilled in the art, a salt form of compound (VI) (e.g., hydrochloride, hydrobromide, trifluoroacetate, paratoluenesulfonate, and other salts known to those skilled in the art) can also be used in the conversion to compound (Vb).

[0094] Formula (VI) (wherein, R 3 , R 4 , R 5 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl) can be obtained by the compound of formula (VIII) 3 , R 4 , R 5 and X are as defined for formula (I), and R 12 and R 13 are independently C1-C6 alkyl), which is shown in Scheme 4 below. Scheme 4 [ka]

[0095] As shown in Scheme 4, compound (VIII) can be converted to compound (VI) by methods known to those skilled in the art, such as those described in International Publication No. 2002059117, J. Med. Chem. 2003, 5238, and Org. Lett. 2022, 2064. For example, this reaction can be carried out in an organic solvent such as DCM, dioxane, or THF in the presence of an organic or inorganic acid such as hydrochloric acid, trifluoroacetic acid, or paratoluenesulfonic acid. Compound (VI) can also be obtained in its salt form (i.e., hydrochloride, hydrobromide, trifluoroacetate, paratoluenesulfonate, and other salts known to those skilled in the art) and used in subsequent transformations.

[0096] Formula (VIII) (wherein, R 3 , R 4 , R 5 and X are as defined for formula (I), and R 12 and R 13 is independently a C1-C6 alkyl) can be obtained by the compound of formula (IX) 3 and X are as defined for formula (I), and R 12 is C1-C6 alkyl) by treating a compound of formula (Xa) (wherein R 4 and R 5 is as defined for formula (I), and R 13 can be obtained by conversion of the hydroxyl group of the methyl group (C1-C6 alkyl, Q is halogen, sulfonate group) with an alkylating agent, as shown in Scheme 5 below. Scheme 5 [ka]

[0097] As shown in Scheme 5, compound (IX) can be converted to compound (VIII) by an alkylation reaction with Xa (i.e., Q is a halogen or a sulfonate Q1 or Q2) by methods known to those skilled in the art and described, for example, in Angew. Chem. Int. Ed. 2017, 12518; WO 2012101244, WO 2004050619, and WO 2007072041. For example, this reaction can be carried out in the presence of a base such as cesium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as DMF, acetone, or acetonitrile. Alternatively, compound (IX) can be converted to compound (VIII) by a Mitsunobu reaction with Xa (when Q is OH) using methods known to those skilled in the art, such as those described in WO 2012074126; Bioorg. Med. Chem. Lett. 1992, 481; Beilstein J. Org. Chem. 2006, 2, 21. For example, this reaction can be carried out in the presence of an azadicarboxylate reagent such as diethyl azadicarboxylate or diisopropyl azadicarboxylate and a phosphine reagent such as triphenylphosphine in an organic solvent such as toluene, THF, or DCM. Alternatively, compound (IX) can be converted to compound (VIII) by an alkylation reaction with aziridine (Xb) using methods known to those skilled in the art, such as those described in WO 2007070201. For example, this reaction can be carried out in the presence of a base such as potassium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as acetonitrile.

[0098] Formula (IX) (where R 3 and X are as defined for formula (I), and R 12 is C1-C6 alkyl) can be obtained by the compound of formula (XII) 3 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl, and R 14 is a halogen) to a compound of formula (XI) 3 and X are as defined for formula (I), and R 12can be obtained in two steps by converting the intermediate compound (C1-C6 alkyl) into Scheme 6 [ka]

[0099] As shown in Scheme 6, compound (XII) can be converted to compound (XI) by a method known to those skilled in the art as the Miyaura boronation reaction, and described, for example, in J. Org. Chem., 1995, 7508; J. Org. Chem., 2021, 103. For example, this reaction can be carried out in an organic solvent such as THF or dioxane in the presence of a base such as potassium carbonate or potassium acetate and a palladium catalyst in combination with an appropriate ligand, such as 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium. Intermediate (XI) can be converted to compound (IX) by a method known to those skilled in the art, and described, for example, in Tetrahedron Lett. 2014, 2082; Tetrahedron Lett. 2017, 3323; Tetrahedron 2005, 1417. For example, this reaction can be carried out in the presence of hydrogen peroxide in a mixture of water and an organic solvent such as ethanol, acetonitrile, or DCM.

[0100] Formula (XII) (wherein, R 3 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl, and R 14 is a halogen) can be prepared by reacting a compound of formula (XIII) 3 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl), which is shown in Scheme 7 below. Scheme 7 [ka]

[0101] As shown in Scheme 7, compound (XIII) can be converted to compound (XII) by a method known to those skilled in the art as aromatic electrophilic halogenation, and described, for example, in WO 2017119700 and WO 2017119700. This reaction can be carried out in an organic solvent such as DCM, chloroform, carbon tetrachloride, or acetonitrile in the presence of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide, bromine, tribromoisocyanuric acid, or trichloroisocyanuric acid at a temperature ranging from −20° C. to 150° C.

[0102] The compound of formula (Ia) according to the present invention, 1 , R 2 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I), and R 3 is a halogen) can be prepared by the compound of formula (Ib) 1 , R 2 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I)), which can be obtained by converting a compound of formula (I) as shown in Scheme 8 below. Scheme 8 [ka]

[0103] Compound (XII) can be converted to a compound of formula (Ia) by methods known to those skilled in the art for electrophilic aromatic halogenation, for example, methods described in WO 2014097041, WO 2010054278, and WO 2010054278. This reaction can be carried out in an organic solvent such as DCM, chloroform, carbon tetrachloride, or acetonitrile in the presence of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide, bromine, tribromoisocyanuric acid, trichloroisocyanuric acid, or 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate at a temperature ranging from −20° C. to 150° C.

[0104] Formula (V) (wherein, R 3 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I), and R 12 is C1-C6 alkyl) can be obtained by the compound of formula (XIII) 3 , R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I), and R 15 is a halogen) to a compound of formula (XIV) 12 is C1-C6 alkyl), or a compound of formula (XV) (wherein R 12 is a C1-C6 alkyl, and R 16 (wherein is a halogen) can be obtained by conversion with a compound of formula (I), as shown in Scheme 9 below. Scheme 9 [ka]

[0105] As shown in Scheme 9, compound (XIII) can be converted to compound (V) by methods known to those skilled in the art and described, for example, in Mol. Catal. 2020, 111043; Angew. Chem. Int. Ed. 2014, 12517; and J. Organomet. Chem. 2002, 30. For example, this reaction can be carried out in the presence of a base such as triethylamine in an organic solvent such as ethanol or methanol under carbon monoxide pressure. To promote the reaction, a palladium catalyst and an appropriate ligand can be used, as described in Advanced Synth. Cat. 2006, 348, 1255.

[0106] Alternatively, compound (XIII) can be converted to compound (V) by methods known to those skilled in the art, such as those described in Tetrahedron Lett. 1989,5093, WO 2011027106, and WO 2015026792. For example, this reaction can be carried out in an organic solvent such as THF, dioxane, or toluene in the presence of a magnesium source such as Mg, isopropylmagnesium chloride, or isopropylmagnesium chloride-lithium chloride complex, or in the presence of a lithium source such as butyllithium, and the reaction temperature can range from -78°C to 150°C.

[0107] Formula (VIII) (wherein, R 3 , R 4 , R 5 and X are as defined for formula (I), and R 12 and R 13 is independently C1-C6 alkyl) can be obtained by the compound of formula (XIVa) 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 is a C1-C6 alkyl, and R 15 is a halogen) to a compound of formula (XIV) 12 is C1-C6 alkyl), or a compound of formula (XV) (wherein R 12 is a C1-C6 alkyl, and R16 (wherein is a halogen) can be obtained by conversion with a compound of formula (I), as shown in Scheme 10 below. Scheme 10 [ka]

[0108] As shown in Scheme 10, compound (XIIIa) can be converted to compound (VIII) by methods known to those skilled in the art, such as those described in Mol. Catal. 2020, 111043; Angew. Chem. Int. Ed. 2014, 12517; and J. Organomet. Chem. 2002, 30. For example, this reaction can be carried out in an organic solvent such as ethanol or methanol under carbon monoxide pressure in the presence of a base such as triethylamine. To promote the reaction, a palladium catalyst and an appropriate ligand can be used, as described in Adv. Synth. Cat. 2006, 348, 1255.

[0109] Alternatively, compound (XIIIa) can be converted to compound (VIII) by a method known to those skilled in the art, such as the methods described in Tetrahedron Lett. 1989,5093, WO 2011027106, and WO 2015026792. For example, this reaction can be carried out in an organic solvent such as THF, dioxane, or toluene in the presence of a magnesium source such as Mg, isopropylmagnesium chloride, or isopropylmagnesium chloride-lithium chloride complex, or in the presence of a lithium source such as butyllithium, and the reaction temperature can range from -78°C to 150°C.

[0110] Formula (XIIIa) (wherein, R 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 is a C1-C6 alkyl, and R 15 is a halogen) can be prepared by reacting a compound of formula (XVII) 3and X are as defined for formula (I), and R 15 is a halogen) to a compound of formula (Xa) 4 and R 5 is as defined for formula (I), and R 13 can be obtained by conversion of the above (wherein Q is a C1-C6 alkyl, and Q is a halogen, a hydroxyl of a sulfonate group) with an alkylating agent, as shown in Scheme 11 below. Scheme 11 [ka]

[0111] As shown in Scheme 11, compound (XVII) can be converted to compound (XIIIa) by an alkylation reaction with Xa (i.e., when Q is a halogen or sulfonate Q1 or Q2) using methods known to those skilled in the art, such as those described in Angew. Chem. Int. Ed. 2017, 12518; WO 2012101244, WO 2004050619, and WO 2007072041. For example, this reaction can be carried out in the presence of a base such as cesium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as DMF, acetone, or acetonitrile. Alternatively, compound (XVII) can be converted to compound (XIIIa) by a Mitsunobu reaction with Xa (when Q is OH) by methods known to those skilled in the art, such as those described in WO 2012074126; Bioorg. Med. Chem. Lett. 1992, 481; Beilstein J. Org. Chem. 2006, 2, 21. For example, this reaction can be carried out in the presence of an azadicarboxylate reagent such as diethyl azadicarboxylate or diisopropyl azadicarboxylate and a phosphine reagent such as triphenylphosphine in an organic solvent such as toluene, THF, or DCM. Alternatively, compound (XVII) can be converted to compound (XIIIa) by an alkylation reaction with aziridine (Xb) by methods known to those skilled in the art and described, for example, in WO 2007070201. For example, this reaction can be carried out in the presence of a base such as potassium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as acetonitrile.

[0112] Formula (IIIa) (wherein Y and R 8 is as defined for formula (I)) is not commercially available, a compound of formula (XIX) (wherein Y is as defined for formula (I) and R 17 is C1-C6 alkyl or benzyl) with a compound of formula (XX) (wherein R 8 can be obtained by conversion using a compound of formula (I) (as defined for formula (I)) via an intermediate of formula (XVIII). Scheme 12 [ka]

[0113] As shown in Scheme 12, compound (XIX) can be converted to an intermediate of formula (XVIII) by methods known to those skilled in the art. This reaction can be carried out under alkylation conditions in an organic solvent such as THF, DCM, DMF, or acetonitrile in the presence of a base such as potassium carbonate, sodium hydride, potassium tert-butoxide, or triethylamine. Similar methods are described in the literature, for example, in WO 2008033562, WO 2008033562, WO 2019183577, WO 2014042939, WO 2011067272, and WO 2013050302. The intermediate of formula (XVIII) can be converted to a compound of formula (IIIa) by methods for cleaving the nitrogen protecting group known to those skilled in the art. For example, this reaction can be carried out in the presence of an organic or inorganic acid such as hydrochloric acid, trifluoroacetic acid, or paratoluenesulfonic acid in an organic solvent such as DCM, dioxane, or THF. Similar methods are described in the literature, for example, in WO 2011067272; WO 2008033562; WO 2008033562. Under these conditions, compound (IIIa) can also be obtained in its salt form (e.g., hydrochloride, hydrobromide, trifluoroacetic acid, paratoluenesulfonic acid, and other salts known to those skilled in the art) and used in subsequent transformations. Alternatively, this reaction can be carried out in an organic solvent such as THF, dioxane, acetonitrile, or DCM in the presence of a base such as potassium hydroxide, sodium hydroxide, or lithium hydroxide. Similar methods are described in the literature, for example, in Tetrahedron: Asymm. 2002, 13, 945. Alternatively, R 17When is a benzyl moiety, the deprotection reaction can be carried out under hydrogenolysis conditions in the presence of an inorganic catalyst such as palladium on carbon (Pd / C) in an organic solvent such as ethyl acetate (EtOAc) or methanol. Similar methods are described in the literature, e.g., WO2008014361; WO2011146335.

[0114] Alternatively, the compound of formula (XVIII) (wherein Y and R 8 is as defined for formula (I), and R 17 is C1-C6 alkyl or benzyl) can be converted into an intermediate of formula (XXI) (wherein Y and R 8 is as defined for formula (I), and R 17 can be obtained by converting a compound of Scheme 13 [ka]

[0115] As shown in Scheme 13, compound (XXI) can be converted to compound (XVIII) by methods known to those skilled in the art. This intramolecular cyclization can be carried out in an organic solvent such as THF, dimethyl sulfoxide, or DCM in the presence of a base such as triethylamine, lithium bis(trimethylsilyl)amide, potassium carbonate, or cesium carbonate. Similar methods are described in the literature, for example, J. Med. Chem. 2001, 44, 2933; U.S. Patent Application Publication No. 20100160303; and Bioorg. Med. Chem. Lett. 2011, 21, 1588. Alternatively, when Q is hydroxyl (Q3), compound (XVIII) can be obtained by a method known to those skilled in the art as the Mitsunobu reaction. For example, this reaction can be carried out in an organic solvent such as toluene or THF in the presence of an azadicarboxylic acid ester reagent such as diethyl azadicarboxylate or diisopropyl azadicarboxylate and a phosphine reagent such as triphenylphosphine or tributylphosphine. Similar methods are described in the literature, for example in Tetrahedron Lett. 2000, 41, 1141. The synthesis of compounds of formula (XVIII) can be carried out as described in J. Med. Chem. 2001, 44, 2933, Tetrahedron Lett. 2000, 41, 1141.

[0116] Alternatively, a compound of formula (IIIa) (wherein R 8 is as defined for formula (I), can be prepared by reacting a compound of formula (XXII) (wherein R 8 can be obtained by converting a compound of formula (I) Scheme 14 [ka]

[0117] As shown in Scheme 14, compound (XXII) can be converted to compounds of formula (IIIa) by methods known to those skilled in the art. This intramolecular cyclization can be carried out in a solvent such as THF, dioxane, or water in the presence of a base such as triethylamine at temperatures ranging from 0° C. to 150° C. Similar methods are described in the literature, for example, in WO2015166094.

[0118] Alternatively, a compound of formula (XVIII) (wherein R 8 is as defined for formula (I), Y is carbonyl, and R 17 is C1-C6 alkyl or benzyl) can be prepared by reacting a compound of formula (XXV) (wherein R 17 is C1-C6 alkyl or benzyl) via intermediates of formula (XXIV) and (XXIII). Scheme 15 [ka]

[0119] As shown in Scheme 15, compound (XXV) can be converted to an intermediate of formula (XXIV) in the presence of a compound of formula (XXVI) by methods known to those skilled in the art. This reaction can be carried out in an organic solvent such as THF, dioxane, toluene, or benzene, optionally using a base such as triethylamine or diisopropylethylamine, at temperatures ranging from 0°C to 180°C. Similar methods are described in the literature, for example, in J. Org. Chem. 1997, 62, 8821. Conversion of compound (XXIV) to a compound of formula (XVIII) can be achieved via an intermediate of formula (XXIII) by a method known to those skilled in the art as intramolecular imide synthesis. Compound (XXIV) can be converted to an activated species of formula (XXIII) (wherein G is a halogen) 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 temperatures ranging from 25°C to 170°C, preferably from 25°C to 80°C.

[0120] Alternatively, compounds of formula (XXIV) can be converted to activated species of formula (XXIII) (wherein G is G6) by treating the compound of formula (XXIV) with, for example, acetic anhydride in the presence of sodium acetate or triethylamine at a temperature of 25 to 170° C., preferably 25 to 80° C. Alternatively, compounds of formula (XVIII) can be prepared by treating the compound of formula (XXIV) with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at a temperature of room temperature to 180° C., to give activated species (XXIII) (wherein G is G1 or G2). Furthermore, the acid of formula (XXIV) can be activated by reaction with a coupling agent such as O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) to give a compound of formula (XXIII) (wherein G is G4). Subsequent intramolecular reaction of (XXIII) gives a compound of formula (XVIII). Similar methods are described in the literature, for example, in WO 2003051842, J. Am. Chem. Soc. 1950, 72, 128; WO 2004022536, WO 2003093261.

[0121] Formula (Ic) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 6 and X are as defined for formula (I)) can be prepared by reacting a compound of formula (Id) 1 , R 2 , R 3 , R 4 , R 5 , R 7 and X are as defined for formula (I)) by reacting a compound of formula (XXVII) 6is as defined for formula (I) and Q is a halogen or sulfonate), which is shown in Scheme 16 below. Scheme 16 [ka]

[0122] As shown in Scheme 16, compound (Id) can be converted to compound (Ic) by methods known to those skilled in the art and described, for example, in ACS Combinatorial Sci. 2016, 569; WO 202115372. For example, this reaction can be carried out in an organic solvent such as DCM, DMF, or acetonitrile in the presence of a base such as potassium carbonate or triethylamine. Alternatively, this reaction can be carried out using a reagent of formula (XXVIIa). In this case, this reaction can be carried out using a catalyst such as 4-(dimethylamino)pyridine in the presence of potassium carbonate or triethylamine in an organic solvent such as DCM, DMF, or acetonitrile, as described, for example, in WO 2021178885; Org. Process Res. Dev. 2014, 18, 205.

[0123] Alternatively, compounds of formula (Id) according to the invention, 1 , R 2 , R 3 , R 4 , R 5 , R 7 and X are as defined for formula (I)) can be prepared by reacting a compound of formula (XXVIII) 1 , R 2 , R 3 , R 4 , R 5 and X are as defined for formula (I)) by reacting a compound of formula (VII) 7 is as defined for formula (I) and G is a halogen or an activating group of formula G5), which is shown in Scheme 17 below. Scheme 17 [ka]

[0124] In Scheme 17, compound (XXVIII) can be converted to compound (Id) by methods known to those skilled in the art, such as those described in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021153720; and WO 2010150192. For example, this reaction can be carried out in an inert organic solvent such as DCM, dioxane, or THF in the presence of a base such as triethylamine, pyridine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. Alternatively, as known to those skilled in the art, salt forms of compound (XXIX) (i.e., hydrochloride, hydrobromide, trifluoroacetate, paratoluenesulfonate, and other salts known to those skilled in the art) can also be used in the conversion to compound (Id).

[0125] Formula (XXVIII) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined for formula (I)) can be prepared by reacting a compound of formula (XXIX) 1 , R 2 , R 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 (wherein is a C1-C6 alkyl) can be obtained by converting the compound shown in Scheme 18 below. Scheme 18 [ka]

[0126] As shown in Scheme 18, compound (XXIX) can be converted to compound (XXVIII) by methods known to those skilled in the art and described, for example, in WO 2002059117, J. Med. Chem. 2003, 5238, and Org. Lett. 2022, 2064. For example, this reaction can be carried out in an organic solvent such as DCM, dioxane, or THF in the presence of an organic or inorganic acid such as hydrochloric acid, trifluoroacetic acid, or paratoluenesulfonic acid. Compound (XXVIII) can also be obtained in its salt form (i.e., hydrochloride, hydrobromide, trifluoroacetate, paratoluenesulfonic acid, and other salts known to those skilled in the art) and used in subsequent transformations.

[0127] Formula (XXIX) (where R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 is C1-C6 alkyl) can be obtained by the compound of formula (XXX) (wherein R 1 , R 2 , R 3 and X are as defined for formula (I)) by reacting a compound of formula (Xa) (wherein R 4 and R 5 is as defined for formula (I), and R 13 can be obtained by conversion of the above (wherein Q is a halogen, a hydroxyl of a sulfonate group) with an alkylating agent, as shown in Scheme 19 below. Scheme 19 [ka]

[0128] As shown in Scheme 19, compound (XXX) can be converted to compound (XXIX) by an alkylation reaction with Xa (i.e., when Q is a halogen or sulfonate Q1 or Q2) by methods known to those skilled in the art, such as those described in Angew. Chem. Int. Ed. 2017, 12518; WO 2012101244, WO 2004050619, and WO 2007072041. For example, this reaction can be carried out in the presence of a base such as cesium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as DMF, acetone, or acetonitrile. Alternatively, compound (XXX) can be converted to compound (XXIX) by a Mitsunobu reaction with Xa (when Q is OH) using methods known to those skilled in the art, such as those described in WO 2012074126; Bioorg. Med. Chem. Lett. 1992, 481; Beilstein J. Org. Chem. 2006, 2, 21. For example, this reaction can be carried out in the presence of an azadicarboxylate reagent such as diethyl azadicarboxylate or diisopropyl azadicarboxylate and a phosphine reagent such as triphenylphosphine in an organic solvent such as toluene, THF, or DCM. Alternatively, compound (XXX) can be converted to compound (XXIX) by an alkylation reaction with aziridine (Xb) using methods known to those skilled in the art and described in WO 2007070201. For example, this reaction can be carried out in the presence of a base such as potassium carbonate, sodium hydride, or sodium carbonate in an organic solvent such as acetonitrile.

[0129] Formula (XXX) (wherein, R 1 , R 2 , R 3 and X are as defined for formula (I)), can be prepared by reacting a compound of formula (XXXII) (wherein R 3 and X are as defined for formula (I)) via an intermediate acid chloride or an activated acylating agent to a compound of formula (III) (wherein R 1 and R 2can be obtained by conversion with a compound of formula (I) as defined above, as shown in Scheme 20 below. Scheme 20 [ka]

[0130] As shown in Scheme 20, compound (XXXII) can be activated to a compound of formula (XXXI) by methods known to those skilled in the art, such as those described in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula (XXXI) (wherein G is a halogen) can be formed by treating compound (XXXII) with, for example, oxalyl chloride or thionyl chloride in an organic solvent such as DCM or THF in the presence of a catalytic amount of DMF at temperatures between 25 and 170°C, preferably between 25 and 80°C. The cleavage of (XXXI) with a fluorine-containing ... 1 and R 2is as defined for formula I), optionally in the presence of a base such as triethylamine or pyridine, to give compounds of formula (XXX). Alternatively, compounds of formula (XXX) can be prepared by treating compounds of formula (XXXII) with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at a temperature between room temperature and 180° C. to give activated species (XXXI) (where G is G1 or G2). Furthermore, compounds of formula (XXXI) (wherein G is G3 and G4) can be obtained by activating acids of formula (XXXII) by reaction with coupling agents such as propanephosphonic anhydride (T3P®) or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt Chem. 1998, 340, 581. Subsequent reaction with amines of formula III gives compounds of formula (XXX).

[0131] Formula (XXXII) (wherein, R 3 and X are as defined for formula (I)) can be prepared by reacting a compound of formula (IX) 3 and X are as defined for formula (I), and R 12 is a C1-C6 alkyl) in the presence of a base or acid, as shown in Scheme 21 below. Scheme 21 [ka]

[0132] As shown in Scheme 21, compound (IX) can be hydrolyzed under basic conditions to give compound (XXXII) by methods known to those skilled in the art and described, for example, in Organic & Biomolecular Chemistry 2014, 2049, WO 2006088716, WO 2000034243, and WO 2002055480. For example, this reaction can be carried out in the presence of a base such as lithium hydroxide, sodium hydroxide, or potassium hydroxide in water or an organic solvent such as methanol, ethanol, THF, or DCM, or in a mixture thereof. Alternatively, the conversion of compound (IX) to compound (XXXII) can be carried out under acidic conditions by methods known to those skilled in the art and described, for example, in Monatsh. Chem. 1985, 661; WO 2015164374. For example, the reaction can be carried out in water or a mixture of water and an organic solvent such as methanol, THF or dioxane in the presence of trifluoroacetic acid, hydrochloric acid or sulfuric acid.

[0133] Formula (XXXIII) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 is C1-C6 alkyl) can be prepared by reacting a compound of formula (XXXV) (wherein R 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 is C1-C6 alkyl) via an intermediate acid chloride or an activated acylating agent to form a compound of formula (III) 1 and R 2 can be obtained by conversion with a compound of formula (I) as defined above, as shown in Scheme 22 below. Scheme 22 [ka]

[0134] As shown in Scheme 22, compound (XXXV) can be activated to a compound of formula (XXXIV) by methods known to those skilled in the art, such as those described in Tetrahedron 2005, 61(46), 10827-10852. For example, compounds of formula (XXXIV) (wherein G is a halogen) can be formed by treating compound (XXXV) with, for example, oxalyl chloride or thionyl chloride in an organic solvent such as DCM or THF in the presence of a catalytic amount of DMF at temperatures between 25 and 170°C, preferably between 25 and 80°C. The cleavage of (XXXIV) with a compound of formula III (wherein R 1 and R 2 is as defined for formula (I), optionally in the presence of a base such as triethylamine or pyridine, to give compounds of formula XXXIII. Alternatively, compounds of formula (XXXIII) can be prepared by treating compounds of formula (XXXV) with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at temperatures between room temperature and 180° C. to give activated species (XXXIV), where G is G1 or G2. Furthermore, the acid of formula (XXXV) can be activated by reaction with a coupling agent such as propanephosphonic anhydride (T3P®) or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) to give compounds of formula (XXXIV) (where G is G3 and G4), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt Chem. 1998, 340, 581. Subsequent reaction with an amine of formula III gives compounds of formula (XXXIII).

[0135] Formula (XXXV) (where R 3 , R 4 , R 5and X are as defined for formula (I), and R 13 is a C1-C6 alkyl) can be obtained by the compound of formula (VIII) 3 , R 4 , R 5 and X are as defined for formula (I), and R 13 and R 12 are independently C1-C6 alkyl) in the presence of a base or acid, as shown in Scheme 23 below. Scheme 23 [ka]

[0136] As shown in Scheme 23, compound (VIII) can be hydrolyzed under basic conditions to give compound (XXXV) by methods known to those skilled in the art, such as those described in Org. Biomol. Chem. 2014, 2049, WO 2006088716, WO 2000034243, and WO 2002055480. For example, this reaction can be carried out in water or in an organic solvent, such as methanol, ethanol, THF, or DCM, or in a mixture thereof, in the presence of a base such as lithium hydroxide, sodium hydroxide, or potassium hydroxide. Alternatively, compound (VIII) can be converted to compound (XXXV) under acidic conditions by methods known to those skilled in the art, such as those described in Monatsh. Chem. 1985, 661; WO 2015164374. For example, the reaction can be carried out in water or a mixture of water and an organic solvent such as methanol, THF or dioxane in the presence of trifluoroacetic acid, hydrochloric acid or sulfuric acid.

[0137] Formula (V) (wherein, R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I), and R 3 is a halogen and R 12is C1-C6 alkyl) can be obtained by the compound of formula (Va) (wherein R 4 , R 5 , R 6 , R 7 and X are as defined for formula (I), and R 12 (wherein is a C1-C6 alkyl) can be obtained by converting the compound shown in Scheme 24 below. Scheme 24 [ka]

[0138] Compound (Va) can be converted to a compound of formula (V) by methods known to those skilled in the art for electrophilic halogenation of aromatics, for example, methods described in WO 2014097041, WO 2010054278, and WO 2010054278. This reaction can be carried out in an organic solvent such as DCM, chloroform, carbon tetrachloride, or acetonitrile in the presence of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide, bromine, tribromoisocyanuric acid, trichloroisocyanuric acid, or 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate at a temperature ranging from −20° C. to 150° C.

[0139] Formula (VIII) (wherein, R 4 , R 5 , R 6 and X are as defined for formula (I), and R 3 is a halogen and R 12 and R 13 is independently a C1-C6 alkyl) can be obtained by the compound of formula (VIIIa) 4 , R 5 , R 6 and X are as defined for formula (I), and R 12 and R 13 are independently C1-C6 alkyl), which is shown in Scheme 25 below. Scheme 25 [ka]

[0140] Compound (VIIIa) can be converted to a compound of formula (VIII) by methods known to those skilled in the art as aromatic electrophilic halogenation, for example, as described in Chem.Comm. 2014, 1262; WO 2014097041, WO 2010054278, and WO 2010054278. This reaction can be carried out in an organic solvent such as DCM, chloroform, carbon tetrachloride, or acetonitrile in the presence of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide, bromine, tribromoisocyanuric acid, trichloroisocyanuric acid, or 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate at a temperature ranging from −20° C. to 150° C.

[0141] Formula (IX) (wherein X is as defined for formula (I) and R 3 is a halogen and R 12 is C1-C6 alkyl) can be obtained by the compound of formula (IXa) (wherein X is as defined for formula (I) and R 12 is a C1-C6 alkyl), which is shown in Scheme 26 below. Scheme 26 [ka]

[0142] Compound (IXa) can be converted to a compound of formula (IX) by methods known to those skilled in the art as aromatic electrophilic halogenation, for example, as described in Tetrahedron 2020, 131521; J. Med. Chem. 2013, 8332; WO 2016112088, WO 2014097041, WO 2010054278, WO 2010054278. The reaction can be carried out in the presence of a halogenating agent such as N-bromosuccinimide, N-chlorosuccinimide, bromine, tribromoisocyanuric acid, trichloroisocyanuric acid or 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate in an organic solvent such as DCM, chloroform, carbon tetrachloride or acetonitrile at a temperature ranging from −20° C. to 150° C.

[0143] Depending on the method or reaction conditions, the reactants may be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0144] The reactants can be reacted directly with each other, i.e., without adding a solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture thereof. When the reaction is carried out in the presence of a base, the base used in excess, such as triethylamine, pyridine, N-methylmorpholine, or N,N-diethylaniline, can also function as a solvent or diluent.

[0145] The reaction is advantageously carried out at a temperature in the range of about -80°C to about +140°C, preferably in the range of about -30°C to about +100°C, often in the range of ambient temperature to about +80°C.

[0146] Depending on the reaction conditions and the choice of starting materials appropriate in each case, for example, only one substituent may be replaced by another substituent according to the invention in one reaction step, or several substituents may be replaced by other substituents according to the invention in the same reaction step.

[0147] Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0148] Salts of compounds of formula I can be converted into the free compounds I in a customary manner, or into acid addition salts, for example by treatment with a suitable basic compound or a suitable ion exchange reagent, or into salts with a base, for example by treatment with a suitable acid or with a suitable ion exchange reagent.

[0149] Salts of compounds of formula I can be converted into other salts of compounds of formula I in a manner known per se, for example by treating an acid addition salt with a salt of an inorganic acid, such as the hydrochloride, with a suitable metal salt, such as the sodium, barium or silver salt of the acid, for example silver acetate, in a suitable solvent in which the inorganic salt formed, for example silver chloride, is insoluble and is therefore precipitated from the reaction mixture.

[0150] Depending on the procedure or reaction conditions, compounds of formula I that have salt-forming properties may be obtained in free form or in salt form.

[0151] The compounds of formula I and, where appropriate, their tautomers, in each case in free form or in salt form, can, depending on the number, the absolute and relative configuration of asymmetric carbon atoms present in the molecule and / or depending on the configuration of non-aromatic double bonds present in the molecule, exist in the form of one of the possible isomers or as a mixture thereof, for example in the form of pure isomers such as enantiomers and / or diastereomers or as isomeric mixtures such as enantiomeric mixtures, for example racemates or diastereomeric mixtures or racemic mixtures; the invention relates to all possible isomeric mixtures as well as to pure isomers, and in each case as mentioned above and hereinafter in this document is to be understood in this sense in each case, even if specific stereochemical details are not stated.

[0152] Diastereomeric or racemic mixtures of compounds of formula I in free or salt form, which may be obtained depending on the starting materials and procedures selected, can be separated into pure diastereomers or racemates on the basis of the physicochemical differences of the components in known manner, for example, by fractional crystallization, distillation and / or chromatography.

[0153] Enantiomeric mixtures, such as racemates, obtainable in a similar manner can be resolved into their optical antipodes by known methods, such as recrystallization from optically active solvents, chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetylcellulose, by utilizing suitable microorganisms, cleavage with specific immobilized enzymes, by the formation of inclusion compounds, for example using chiral crown ethers which complex with only one enantiomer, or by conversion of diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, such as a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixtures thus obtainable, for example by fractional crystallization based on their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example a basic agent.

[0154] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomeric mixture, but also by generally known diastereoselective or enantioselective synthetic methods, e.g. by carrying out the process according to the invention using starting materials with the appropriate stereochemistry.

[0155] The N-oxides can be prepared by reacting the compounds of formula I with a suitable oxidizing agent, such as the H2O2 / urea adduct, in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidations are known from the literature, for example from J. Med. Chem., 32(12), 2561-73, 1989 or WO 2000 / 15615.

[0156] If the biological activity of the individual components differs, it may be advantageous in each case to isolate or synthesize the more biologically effective isomer, e.g., enantiomer or diastereomer, or isomer mixture, e.g., enantiomeric or diastereomeric mixture.

[0157] The compounds of formula I and, where appropriate, their tautomers are in each case in free form or in salt form, which may, where appropriate, also be obtained in the form of hydrates and / or contain other solvents, for example solvents which may have been used for the crystallization of the compounds present in solid form.

[0158] The following table illustrates specific compounds of the present invention.

[0159] The compounds according to the following Tables A1 to A4 can be prepared according to the above methods. The following examples are intended to illustrate the present invention and to show preferred compounds of formula (I). In any of the following Tables A1 to A4, the possible presence of one or more asymmetric carbon atoms in the compounds of formula (I) according to the present invention means that chiral isomeric forms of the compounds, i.e., enantiomers or diastereomers, can exist.

[0160] Compounds of formula (I) according to the following Tables A1 to A4 can be prepared according to the above methods. The examples given below are intended to illustrate the invention and to show preferred compounds of formula (I) in the form of formulae (I-A1) and (I-A2).

[0161] Table A1 shows compounds of formula (I-A1) where X is -CH and R 4 is hydrogen and R 5 is methyl and R 1 , R 2 , R 3 , R 6 and R 9 are as defined in Table A1). [ka]

[0162] [Table 1-1]

[0163] [Table 1-2]

[0164] Table 1-3

[0165] Table 1-4

[0166] Table 1-5

[0167] Table 1-6

[0168] Table 1-7

[0169] Table 1-8

[0170] Table 1-9

[0171] Table 1-10

[0172] Table 1-11

[0173] Table 1-12

[0174] Table A2 shows compounds of formula (I-A2) where X is CH and R 4 is hydrogen and R 5 is methyl and R 1 is the formula (W) [ka] and R is selected from the heterocycles 3 , R 8 , R 9 and Y are as defined in Table A2). [ka]

[0175] [Table 2-1]

[0176] [Table 2-2]

[0177] [Table 2-3]

[0178] [Table 2-4]

[0179] Table A3 shows the formula (I-A1) [ka] (wherein X is -CHCH and R 4 is hydrogen and R 5 is methyl and R 1 , R 2 , R 3 , R 6 and R9 are as defined in Table A3) This shows 264 compounds.

[0180] [Table 3-1]

[0181] [Table 3-2]

[0182] [Table 3-3]

[0183] [Table 3-4]

[0184] [Table 3-5]

[0185] [Table 3-6]

[0186] [Table 3-7]

[0187] [Table 3-8]

[0188] [Table 3-9]

[0189] [Table 3-10]

[0190] Table A4 shows compounds of formula (I-A2) where X is -CHCH and R 4 is hydrogen and R 5 is methyl and R 1 is the formula (W) [ka] and R is selected from the heterocycles 3 , R 8 , R 9 and Y are as defined in Table A4). [ka]

[0191] [Table 4-1]

[0192] [Table 4-2]

[0193] [Table 4-3]

[0194] [Table 4-4]

[0195] 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, 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 all or individual developmental stages of pests, such as insects or representatives of the order Acarina, which are normally susceptible, but also against resistant pests. The insecticidal or acaricidal activity of the active ingredients according to the present invention can be manifested directly, for example, as the killing of pests, immediately or only after a certain period of time, for example, during molting, or indirectly, for example, as a reduction in egg-laying rate and / or hatching rate.

[0196] Examples of pests mentioned above include: 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., 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 of the Anoplura, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; Coleoptera, e.g. 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 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. spp.), Maladera castanea, Megascelis spp., Meligethes 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. spp.) and Trogoderma spp.;. Diptera, e.g. 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 melanogaster, Fannia 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., Rhagoletis spp., Rivelia quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. and Tipula spp.; Hemiptera, e.g. 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, 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., 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 psyllid, Diuraphis noxia, Dysaphis spp., Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp. 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.), Japanese pear aphid (Nippolachnus piri Mats), Odonaspis ruthae, Oregma lanigera Zehnter, Japanese 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., Mulberry scale (Pseudaulacaspis spp.), mulberry mealybugs (Pseudococcus spp.), cotton flea beetles (Pseudatomoscelis seriatus), Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, lightning leafhoppers (Recilia dorsalis), Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., and white-backed planthoppers (Sogatella furcifera, Spisstilus festinus, Tarophagus Proserpina, Toxoptera spp., Trialeurodes spp., Tridiscus sporoboli, Trionymus spp.), Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris;. the order Hymenoptera, for example Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp., the family Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Pogonomyrmex spp., Slenopsis invicta, Solenopsis spp. and Vespa spp.; Isoptera, for example, Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Solenopsis geminate; Lepidoptera, e.g. 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, peach fruit moth (Carposina nipponensis), borer moths (Chilo spp.), banded moths (Choristoneura spp.), Chrysoteuchia topiaria, grapevine moth (Clysia ambiguella), Cnaphalocrosis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, cotton moth (Cosmophila flava), Crambus spp., woolly moth (Crocidolomia binotalis), Cryptophlebia leucotreta leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp.), Corn moth (Elasmopalpus lignosellus), Eldana saccharina, Ephestia spp., Epinotia spp., Estigmene acrea, Etiella zinckinella, Eucosma spp., Grape bean moth (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, Gypsy moths (Lymantria spp.), Lyonetteia spp., Malacosoma spp., Mamestra brassicae, Tobacco hornworms (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, white borer (Scirpophaga spp.), Sesamia spp.), Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta and Yponomeuta spp.;. Mallophaga, e.g., Damalinea spp. and Trichodectes spp.; Orthoptera, for example Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Neocurtilla hexadactyla, Periplaneta spp., Scapteriscus spp. and Schistocerca spp.; Psocoptera, e.g., Liposcelis spp.; from the order Siphonaptera, for example Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; Thysanoptera, e.g., Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.; For example, the silverfish (Lepisma saccharina) from the order Thysanura.

[0197] In a further aspect, the present invention relates to the prevention of plant parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes) from plants and parts thereof, in particular Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other species of the genus Meloidogyne; cyst nematodes, Globodera rostochiensis and other species of the genus Globodera; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other Heterodera species; seed gall nematode, Anguina species; stem and foliar nematode, Aphelenchoides species; sclerenchyma, Belonolaimus longicaudatus and other Belonolaimus species; pine nematode, Bursaphelenchus xylophilus and other species of the pinewood nematode genus Bursaphelenchus; ring nematodes, species of Criconema, species of Criconemella, species of Criconemoides, and species of Mesocriconema;Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; awl nematodes, Dolichodorus species; screw nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; sheath and sheathoid nematodes nematode, species of the genus Hemicycliophora and species of Hemicriconemoides; species of the genus Hirshmanniella; lance nematode, species of the genus Hoploaimus; false rootknot nematode, species of the genus Nacobbus; yarrow nematode, Longidorus elongatus and other species of Longidorus; pin nematode, species of the genus Pratylenchus; root-lesion nematode, Pratylenchus neglectus, northern root-lesion nematode, Pratylenchus penetrans), Pratylenchus curvitatus, Pratylenchus goodeyi and other species of the genus Pratylenchus; the root-mining nematode, Radopholus similis and other species of the genus Radopholus;Reniform nematode, Rotylenchus robustus, Rotylenchus reniformis and other species of the genus Rotylenchus; Scutellonema; Trichodorus primitivus and other species of the genus Trichodorus, Paratrichodorus; Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other species of the genus Tylenchorhynchus; Citrus nematode The present invention may also relate to a method for suppressing damage caused by plant-parasitic nematodes, such as Tylenchulus species; Dagger nematode, Xiphinema species; and other plant-parasitic nematode species, such as Subanguina species, Hypsoperine species, Macroposthonia species, Melinius species, Punctodera species, and Quinisulcius species.

[0198] The compounds of the invention may also have activity against mollusks.Examples include species belonging to the following families: Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. nemoralis); Ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum) ulatum); 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) ; Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.

[0199] The active ingredients according to the invention can be used in agriculture, horticulture and forestry to control, i.e. suppress or destroy, pests of the types mentioned above which occur in particular on plants, especially useful and ornamental plants, or on organs of such plants, such as fruits, flowers, leaves, stems, tubers or roots, optionally while also leaving plant organs formed at a later time protected against these pests.

[0200] 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, such as apples, pears, plums, peaches, almonds, cherries or berries, such as strawberries, raspberries or blackberries; legumes, such as beans, lentils, peas or soybeans; oilseed crops, such as rapeseed, mustard, poppy, olives, sunflower, coconut, castor, cocoa or peanuts; citrus fruits, such as oranges, lemons, grapefruits or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes or peppers; lauraceae, such as avocados, Cinnamonium or camphor; also tobacco, tree nuts, coffee, eggplant, sugarcane, tea, pepper, grapes, hops, plantain; and latex plants.

[0201] In particular embodiments, the compounds of formula (I) are capable of controlling mites, rust mites and spider mites on crops, trees and plants selected from vegetables (especially tomatoes and cucumbers), citrus fruits, pome fruits, stone fruits, nuts, cotton, tropical crops, avocados, ornamentals, beans, soybeans, strawberries and grapes.

[0202] 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.

[0203] For example, the present invention may be used with any of the ornamental species belonging to the following genera: 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., Brassica spp.) (ornamental), Calceolaria spp., Capsicum annuum, Catharanthus roseus, Canna spp., Cornflowers (Centaurea spp.), Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Bleeding hearts (Dicentra spectabilis), Dorotheanthus spp.), Lisianthus (Eustoma grandiflorum), Forsythia (Forsythia spp.), Fuchsia (Fuchsia spp.), Geranium gnaphalium, Gerbera (Gerbera spp.), Globetrotter (Gomphrena globosa), Heliotropium (Heliotropium spp.), Sunflower (Helianthus spp.), Hibiscus (Hibiscus spp.), Hydrangea (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., Nemesia spp., Tagetes spp. spp.), Dianthus spp. (carnations), Canna spp., Oxalis spp., Bellis spp., Pelargonium spp. (Pelargonium peltatum, P. Zonale), Viola spp. (pansies), Petunia spp., Phlox spp., Plectranthus spp., Poinsettia spp., Parthenocissus spp. spp.) (American Creeper (P. quinquefolia), Common Ivy (P. tricuspidata)), Primula spp., Ranunculus spp., Rhododendron spp., Rosa spp. (roses), Rudbeckia spp., Saintpaulia spp., Salvia spp., Blue Fanflower (Scaevola aemola), Schizanthus wisetonensis, Stonecrop (Sedum spp.), Solanum spp., Petunia (Surfinia spp.)), Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other bedding plants.

[0204] The present invention may be used, for example, for any of the vegetable species belonging to the following: Allium spp. (garlic (A. sativum), onion (A. cepa), shallot (A. oschaninii), leek (A. porrum), scallion (A. ascalonicum), spring 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)), 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.coccineus), peas (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 beans (Vicia faba).

[0205] Preferred ornamental plant species include African violet, begonia, dahlia, gerbera, hydrangea, verbena, rosa, kalanchoe, poinsettia, aster, centaurea, coreopsis, delphinium, monarda, and phlox. , Rudbeckia, Sedum, Petunia, Viola, Impatiens, Geranium, Chrysanthemum, Ranunculus, Fuchsia, Salvia, Hortensia, rosemary, sage, St. John's wort, mint, peppers, tomatoes, and cucumbers.

[0206] The compounds of formula (I) may be particularly suitable for controlling mites, spider mites and rust mites, such as 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 spp. 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; Dermanyssus gallinae; Dermanyssus spp.; Eotetranychus spp.;Eotetranychus willamettei;Epitrimerus pyri;Eriophyes ribis;Eriophyes spp.;Eriophyes vitis;Eutetranychus spp.;Halotydeus destructor;Hemitarsonemus spp.;Knemidocoptes spp.;Laminosioptes spp.;Listrophorus spp.;Myobia spp.;Neoschongastia xerothermobia 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 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. spp.); Sarcoptes bovis; Sarcoptes canis; Sarcoptes caprae; Sarcoptes equi; Sarcoptes ovis; Sarcoptes rupicaprae; Sarcoptes spp.; Sarcoptes 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.; Vasates lycopersici; and Zetzellia mali.

[0207] In one embodiment, the compounds of formula (I) are capable of controlling one or more of the following: 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; Eutetranychus orientalis; Oligonychus pratensis; Panonychus citri; Panonychus ulmi; Phyllocoptes vitis; Phyllocoptruta oleivora; Polyphagotarsonemus latus; Tetranychus cinnabarinus; Tetranychus kanzawai; Tetranychus spp.; and Tetranychus urticae.

[0208] In a further embodiment, the compounds of formula (I) disclosed herein may be particularly suitable for the control of one or more of the following: 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.

[0209] It should be understood that the term "crop plant" also includes crop plants that have been transformed using recombinant DNA techniques to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0210] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, such as insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; or insecticidal proteins derived from Bacillus thuringiensis, such as δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or plant insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A; or bacteria symbiotic to nematodes, such as Photorhabdus genus, such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc. insecticidal proteins of Xenorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; 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, papain inhibitors; ricin, corn-RIP, abrin, rufin, saporin or ribosome-inactivating proteins (RIPs) such as 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.

[0211] In the context of the present invention, it should be understood that δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or plant insecticidal proteins (Vips), such as Vip1, Vip2, Vip3, or Vip3A, may also be 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). A truncated toxin, for example, a truncated Cry1Ab, is known. Modified toxins are toxins in which one or more amino acids of a naturally occurring toxin have been substituted. 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, for example, WO 03 / 018810).

[0212] Such toxins or genetically modified 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.

[0213] The processes for producing 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 production are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0214] The toxins contained in the genetically modified plants confer resistance to harmful insects found in all insect taxa, but particularly in beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0215] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and 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 phosphinothricin N-acetyltransferase (PAT), an enzyme that confers tolerance to glufosinate ammonium herbicides); 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) resistance trait), and Protecta®.

[0216] Further examples of such genetically modified crops include: 1. Bt11 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through recombinant expression of a truncated Cry1Ab toxin. Bt11 maize also conferred resistance to the herbicide glufosinate-ammonium through recombinant expression of the PAT enzyme. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically modified maize (Zea mays) resistant to the European corn borer (Ostrinia nubilalis) and Sesamia nonagrioides by recombinantly expressing the Cry1Ab toxin. Bt176 maize also has resistance to the herbicide glufosinate-ammonium by recombinantly expressing the PAT enzyme. 3. MIR604 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by recombinantly expressing a modified Cry3A toxin. This toxin is Cry3A055 modified by inserting a cathepsin-G-protease recognition sequence. The generation of such transgenic maize plants is described in WO 03 / 018810. 4. MON 863 maize, registration number C / DE / 02 / 9, from Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. IPC 531 Cotton, registration number C / ES / 96 / 02, from Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. 6. 1507 corn, registered under the number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. This corn has been genetically modified to express the Cry1F protein for resistance to certain Lepidoptera insects and the PAT protein for resistance to the glufosinate-ammonium herbicide. 7. NK603 x MON 810 maize, registration number C / GB / 02 / M3 / 03, from Monsanto Europe SA270-272 Avenue de Tervuren, B 1150 Brussels, Belgium. This hybrid maize variety was obtained by crossing the genetically modified varieties NK603 and MON 810 through conventional breeding. NK603 x MON 810 maize recombinantly expresses the CP4 EPSPS protein, derived from Agrobacterium sp. strain CP4, which confers resistance to Roundup® (containing glyphosate) herbicides, and the Cry1Ab toxin, derived from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain lepidopteran insects, such as the European corn borer.

[0217] Genetically modified crops with insect resistance are also described in the BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland), Report 2003 (http: / / bats.ch).

[0218] It should be understood that the term "crop plant" also includes crop plants that have been transformed using recombinant DNA techniques so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "disease-related proteins" (PRPs, see, for example, EP 0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP 0 392 225, WO 95 / 33818 and EP 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 publications mentioned above.

[0219] Crops can also be modified 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.

[0220] Crops also include those with increased resistance to nematodes, such as the soybean cyst nematode.

[0221] Crops that are tolerant to abiotic stress include, for example, those that have increased tolerance to drought, high salt concentrations, high temperature, low temperature, frost, or light radiation due to the expression of NF-YB or other proteins known in the art.

[0222] Pathogen resistance substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium and calcium channels, for example virus-derived 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).

[0223] Further fields of use of the compositions according to the invention are the protection of stored articles and storage rooms and raw materials such as wood, textiles, flooring or buildings from pests of the types mentioned above, and also in the hygiene sector, in particular the protection of humans, livestock and productive livestock animals.

[0224] The present invention provides a compound of the first aspect for use in therapy. The present invention provides a compound of the first aspect for use in controlling parasites in or on animals. Further, the present invention provides a compound of the first aspect for use in controlling ectoparasites on animals. Furthermore, the present invention provides a compound of the first aspect for use in the prevention and / or treatment of diseases transmitted by ectoparasites. According to this particular aspect of the invention, surgical or therapeutic treatment of the human or animal body may be excluded from this use.

[0225] The present invention provides the use of a compound of the first aspect for the manufacture of a medicament for controlling ectoparasites in or on an animal. Further, the present invention provides the use of a compound of the first aspect for the manufacture of a medicament for controlling ectoparasites on an animal. Further, the present invention provides the use of a compound of the first aspect for the manufacture of a medicament for preventing and / or treating ectoparasite-borne diseases.

[0226] The present invention provides the use of a compound of the first aspect for controlling parasites in or on an animal. Additionally, the present invention provides the use of a compound of the first aspect for controlling ectoparasites on an animal.

[0227] When the term "control" is used in relation to parasites in or on animals, it refers to reducing the number of pests or parasites, eradicating pests or parasites, and / or preventing further occurrence of pests or parasites.

[0228] The term "treatment" when used in reference to a parasite in or on an animal refers to inhibiting, slowing, halting or reversing the progression or severity of an existing condition or disease.

[0229] When the term "prevention" is used in reference to a parasite in or on an animal, it refers to avoiding the occurrence of a symptom or disease in the animal.

[0230] When the term "animal" is used in reference to parasites in or on animals, it can refer to mammals and non-mammals, such as birds or fish. In the case of mammals, it 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.

[0231] A "parasite" is a harmful organism that lives in or on a host animal and benefits by extracting nutrients from it while causing harm to the host animal. An "endoparasite" is a parasite that lives inside the host animal. An "ectoparasite" is a parasite that lives on the surface of the host animal. Ectoparasites include, but are not limited to, mites, insects, and crustaceans (e.g., fish lice). The subclass Acari (or Acarina) includes ticks and mites. Ticks include, but are not limited to, ticks belonging to 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, mites belonging to the following genera: Chorioptes, such as Chorioptes bovis; Psoroptes, such as Psoroptes ovis; Cheyletiella; Dermanyssus, such as Dermanyssus gallinae; Ornithonyssus; Demodex, such as Demodex canis; Sarcoptes, such as Sarcoptes scabiei; and Psorergates.Insects include, but are not limited to, those belonging to the following orders: Siphonaptera, Diptera, Phthiraptera, Lepidoptera, Coleoptera, and Homoptera. Those belonging to the Siphonaptera include, but are not limited to, the cat flea (Ctenocephalides felis) and the dog flea (Ctenocephalides canis). The order Diptera includes, but is not limited to, Musca spp.; bot flies such as Gasterophilus intestinalis and Oestrus ovis; stable flies; horse flies such as Haematopota spp. and Tabanus spp.; Haematobia such as Haematobia irritans; Stomoxys spp.; Lucilia spp.; midges; and mosquitoes. Classifications of the order Phthiraptera include, but are not limited to, blood-sucking lice and lice with chewing mouthparts, such as the sheep body louse (Bovicola ovis) and the cattle body louse (Bovicola bovis).

[0232] When the term "effective amount" is used in reference to a parasite in or on an animal, it refers to the amount or dosage of a compound of the present invention or its salt that produces the desired effect in or on the animal when administered to the animal in single or multiple doses. An effective amount can be readily determined by a skilled diagnostician using known techniques and observing results obtained under similar circumstances. In determining an effective amount, the diagnostician will consider many factors, including, but not limited to, the species of mammal, its size, age, and health, the parasite and level of infestation to be controlled, the specific disease or disorder involved, the degree of involvement or severity of the disease or disorder, the individual's response, the specific compound administered, the mode of administration, the bioavailability characteristics of the administered formulation, the selected dosing schedule, the use of concomitant medications, and other relevant circumstances.

[0233] The compounds of the present invention can be administered to animals by any route that achieves 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 take the form of pour-ons, spots, sprays, spray channels, or dips. Alternatively, the compounds of the present invention can be administered using ear tags or collars.

[0234] Salt forms of the compounds of the present invention include both pharmaceutically acceptable salts and veterinarily acceptable salts, which may differ from agrochemically acceptable salts. Pharmaceutically and veterinarily acceptable salts and general methodologies for preparing them are known in the art. See, for example, Gould, PL, "Salt selection for basic drugs," Int. J. Pharma., 33:201-217 (1986); Bastin, RJ, et al., "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities," Org. Process Res. Dev., 4:427-435 (2000); and Berge, SM, et al., "Pharmaceutical Salts," J. Pharm. Sci., 66:1-19 (1977). Those skilled in the art of synthesis will understand that the compounds of the present invention can be easily converted into and isolated as salts, such as hydrochloride salts, using techniques and conditions known to those skilled in the art. Additionally, one skilled in the art of synthesis will recognize that compounds of the invention can be readily converted to and isolated from the corresponding salt form of the corresponding free base.

[0235] The present invention also provides methods for controlling pests (e.g., 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, spreading, or dipping. By way of example, IRS (indoor residual spray) application to surfaces such as wall, ceiling, or floor surfaces is contemplated by the method of the present invention. In other embodiments, it is contemplated to apply such compositions to substrates such as nonwoven or woven materials in the form of (or that can be used in the manufacture of) netting, clothing, curtains, and tents.

[0236] 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, so as to impart effective residual pesticidal activity on the surface or substrate. Such application may be by brushing, rolling, spraying, spreading, or dipping the pesticidal composition of the present invention. By way of example, IRS application to a surface, such as a wall, ceiling, or floor surface, is contemplated by the method of the present invention, so as to impart effective residual pesticidal activity to the surface. In other embodiments, it is contemplated to apply such compositions to substrates, such as nonwoven or woven materials in the form of (or that can be used to manufacture) netting, clothing, curtains, and tents, for residual pest control.

[0237] The substrate to be treated, such as textiles, fabrics or netting, can be made of natural fibres such as cotton, raffia, jute, flax, sisal, hessian or wool, or synthetic fibres 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, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886 or WO 2007 / 090739.

[0238] A further field of use for the compositions according to the invention may be in the field of trunk injection / trunk treatment for all ornamental trees and for all kinds of fruit and nut trees.

[0239] In the field of trunk injection / trunk treatment, the compounds according to the invention may be particularly suitable against the wood-boring insects of the orders Lepidoptera and Coleoptera mentioned above, in particular the wood-boring organisms listed in Tables A and B below.

[0240] [Table 5]

[0241] [Table 6-1]

[0242] [Table 6-2]

[0243] [Table 6-3]

[0244] [Table 6-4]

[0245] The present invention can also be used to control any pest insect that may be present in turfgrass, such as beetles, caterpillars, fire ants, ground pearls, millipedes, woodlice, mites, mole crickets, scale insects, mealybugs, mites, boxworms, southern chinch bugs, and white grubs. The present invention can be used to control pest insects at various stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0246] In particular, the present invention can be used to control harmful insects that feed on the roots of turfgrass, such as white grubs (e.g., Cyclocephala spp. (e.g., masked scarab, C. lurida), Rhizotrogus spp. (e.g., European chafer, R. majalis), Cotinus spp. (e.g., blue spill beetle, C. nitida), Popillia spp. (e.g., Japanese beetle, P. japonica), Phyllophaga spp. (e.g., May / June beetle, P. japonica), and the like. beetle), Ataenius spp. (e.g., Black turfgrass Ataenius, A. spretulus), Maladera spp. (e.g., Red-billed beetle, M. castanea) and Tomarus spp.), ground pearl (Margarodes spp.), field crickets (Brown field cricket, Southern field cricket and Wingless field cricket; Scapteriscus spp., Gryllotalpa africana) and crane fly larvae (European crane fly). fly), and Tipula spp.

[0247] The present invention can also be used to control thatch-dwelling pests of turfgrass, such as cutworms (e.g., the armyworm, i.e., Spodoptera frugiperda, and the common cutworm, Pseudaletia unipuncta), cutworms, weevils (Sphenophorus spp., e.g., S. venatus verstitus and S. parvulus), and sodwebworms (e.g., Crambus spp. and the tropical sodwebworm, i.e., Herpetogramma phaeopteralis).

[0248] The present invention can also be used to control insect pests of turfgrass that live above ground and feed on turfgrass leaves, such as chinch bugs (e.g., southern chinch bug, Blissus insularis), Bermuda grass mite (Eriophyes cynodoniensis), Rhodes grass mealybug (Antonina graminis), two-lined spittlebug (Propsapia bicincta), leafhoppers, cutworms (Noctuidae), and greengrass aphids.

[0249] The present invention may also be used to control other pests of turfgrass, such as the red fire ant (Solenopsis invicta), which builds ant mounds in turf.

[0250] In the hygiene field, the compositions according to the invention may be effective against ectoparasites such as hard mites, ulcerative colitis mites, scabies mites, chiggers, flies (stable flies and dentaries), parasitic fly larvae, lice, head lice, biting lice and fleas.

[0251] Examples of such parasites include: Order Anoplurida: Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. species. Order Mallophagida: species of the genera Trimenopon, Menopon, Trinoton, Bovicola, Werneckiella, Lepikentron, Damalina, Trichodectes and Felicola. from the order Diptera and the suborder Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp. spp.), Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.), Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp. species. The order Siphonapterida, for example species of the genera Pulex, Ctenocephalides, Xenopsylla and Ceratophyllus. Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. The order Blattaria, for example Blatta orientalis, Periplaneta americana, Blattela germanica and Supella spp. species. The subclass Acaria (Acarida) and the orders Metastigmata and Mesostigmata, for example 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. from the suborder Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp. spp.), Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp. species.

[0252] The compositions according to the invention may also be suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and cardboard, leather, flooring and buildings from insect infestations.

[0253] The compositions according to the invention can be used, for example, against the following pests: European house longhorn beetle (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 linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus species, Tryptodendron species, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon speciesand Dinoderus minutus, as well as hymenopteran species such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, and Urocerus augur, as well as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, and other species of the order ...lucifugus, and other species of the order Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes lucifugus, and other species of Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes lucifugus, and other species of Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes lucifugus, and other species of Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes lucifugus, Termites such as Mastotermes darwiniensis, Zootermopsis nevadensis, and Coptotermes formosanus, as well as wood mites such as Lepisma saccharina.

[0254] The compounds of formula (I), (IA), (I-A1) or (I-A2) or one of the compounds selected from the group consisting of the compounds set out in Tables A1 to A4 or the compounds selected from P-1 to P-9 set out in Table P (described below), or salts thereof, are particularly suitable for controlling one or more pests belonging to the following genera: Spodoptera spp., Helicoverpa spp., Heliothis spp., Leucinodes spp., Tuta spp., Plutella spp., Cydia spp., Lobesia spp., Tortrix spp., Amyelois spp., Maruca spp. spp.), Chrysodeixis spp., Agrotis spp., Elasmopalpus spp., Dalbulus spp., Sternechus spp., Phyllotreta spp., Popillia spp., Scirpophaga spp., Chilo spp., Cnaphalocrosis spp., Tetranychus spp., Panonychus spp., Polyphagotarsonemus spp. spp.), Phyllocoptruta spp., Aculus spp., Brevipalpus spp., Oligonychus spp., Aculops spp., Nilaparvata spp., Sogatella spp., Laodelphax spp., Nephotettix spp., Diabrotica spp., Agriotes spp.), Hypnoidus spp., Limonius spp., Melanotus spp., Conoderus spp., Delia spp., Amphimallon spp., Popillia spp., Euschistus spp., Piezodorus spp., Nezara spp., Dichelops spp., Lygus spp., Leptocorisa spp., Eurygaster spp., Halymorpha spp.), Thrips spp., Scirtothrips spp., Frankliniella spp., Anthonomus spp., Melingethes spp., Phyllotreta spp., Leptinotarsa ​​spp., Bemisia spp., Trialeurodes spp., Aphis spp. and Myzus spp.

[0255] In a preferred embodiment of each aspect, compound TX (the abbreviation "TX" refers to one compound selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 shown in Table P (described below)) controls one or more pests selected from the following genera: Spodoptera spp., Helicoverpa spp., Heliothis spp., Leucinodes spp., Tuta spp., Plutella spp., Cydia spp., Lobesia spp., Tortrix spp. spp.), Amyelois spp., Maruca spp., Chrysodeixis spp., Agrotis spp., Elasmopalpus spp., Dalbulus spp., Sternechus spp., Phyllotreta spp., Popillia spp., Scirpophaga spp., Chilo spp., Cnaphalocrocis spp., Tetranychus spp. spp.), Panonychus spp., Polyphagotarsonemus spp., Phyllocoptruta spp., Aculus spp., Brevipalpus spp., Oligonychus spp., Aculops spp., Nilaparvata spp., Sogatella spp.), Laodelphax spp., Nephotettix spp., Diabrotica spp., Agriotes spp., Hypnoidus spp., Limonius spp., Melanotus spp., Conoderus spp., Delia spp., Amphimallon spp., Popillia spp., Euschistus spp., Piezodorus spp. spp.), Nezara spp., Dichelops spp., Lygus spp., Leptocorisa spp., Eurygaster spp., Halymorpha spp., Thrips spp., Scirtothrips spp., Frankliniella spp., Anthonomus spp., Melingethes spp., Phyllotreta spp., Leptinotarsa ​​spp. spp.), Bemisia spp., Trialeurodes spp., Aphis spp., Myzus spp.

[0256] The compounds of formula (I), (IA), (I-A1) or (I-A2) or one of the compounds selected from the group consisting of the compounds shown in Tables A1 to A4 or the compounds selected from P-1 to P-9 shown in Table P (described below), or salts thereof, are particularly suitable for controlling one or more pests selected from the following: Spodoptera spp. (e.g. Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Cydia pomonella, Lobesia spp. spp.), Tortrix spp., Bean borer (Maruca vitrata), Chrysodeixis includens, Cutthroat moth (Agrotis ipsilon), Corn moth (Elasmopalpus lignosellus), Dalbulus maidis, Flea beetle (Phyllotreta spp.), Japanese beetle (Popillia japonica), Japanese corn borer (Scirpophaga incertulas), Rice stem borer (Chilo suppressalis), Rice leafroller (Cnaphalocrosis medinalis), Two-spotted spider mite (Tetranychus urticae), Apple red mite (Panonychus ulmi), Tea dust mite (Polyphagotarsonemus latus), citrus rust mite (Phyllocoptruta oleivora), Brevipalpus spp.), apple rust mite (Aculops lycopersici), brown planthopper (Nilaparvata lugens), Sogatella frucifera, small brown planthopper (Laodelphax striatellus), green rice leafhoppers (Nephotettix spp.), Diabrotica vigifera, Agriotes spp., Hypnoidus bicolor, Limonius canus, Delia radicum, Japanese beetle (Popillia japonica), Euschistus heros, Piezodorus lituratus lituratus, southern green stink bug (Nezara viridula), Dichelops furcatus, Lygus species (Lygus sp.), narrow-leaved stink bug (Leptocorisa acuta), brown marmorated stink bug (Halyomorpha halys), onion thrips (Thrips tabaci), tea flower thrips (Scirtothrips dorsalis), western flower thrips (Frankliniella occidentalis), boll weevil (Anthonomus grandis), Meligethes aeneus, striped flea beetle species (Phyllotreta spp.), Colorado potato beetle (Leptinotarsa ​​decemLineata), tobacco whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii) and green peach aphid (Myzus persicae).

[0257] In a preferred embodiment of each aspect, the compound TX (the abbreviation "TX" refers to one compound selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 shown in Table P (described below)) controls one or more pests selected from the following genera: Spodoptera spp. (e.g., Spodoptera frugiperda, Spodoptera littoralis) + TX, Helicoverpa armigera + TX, Heliothis virescens + TX, Leucinodes orbonalis + TX, Tuta absoluta + TX, Plutella xylostella xylostella + TX, Codling moth (Cydia pomonella) + TX, Lobesia spp. + TX, Tortrix spp. + TX, Bean leaf moth (Maruca vitrata) + TX, Chrysodeixis includens + TX, Cutthroat moth (Agrotis ipsilon) + TX, Corn leaf moth (Elasmopalpus lignosellus) + TX, Dalbulus maidis + TX, Striped flea beetle (Phyllotreta spp.) + TX, Japanese beetle (Popillia japonica) + TX, One-leaf borer (Scirpophaga incertulas) + TX, Rice stem borer (Chilo suppressalis + TX, rice leafroller (Cnaphalocrosis medinalis) + TX, two-spotted spider mite (Tetranychus urticae) + TX, apple red mite (Panonychus ulmi) + TX, tea dust mite (Polyphagotarsonemus latus) + TX, citrus rust mite (Phyllocoptruta oleivora) + TX, Brevipalpus spp.) + TX, apple rust mite (Aculops lycopersici) + TX, brown planthopper (Nilaparvata lugens) + TX, Sogatella frucifera + TX, small brown planthopper (Laodelphax striatellus) + TX, green rice leafhopper (Nephotettix spp.) + TX, Diabrotica vigifera + TX, Agriotes spp. + TX, Hypnoidus bicolor + TX, Limonius canus + TX, Delia radicum + TX, Japanese beetle (Popillia japonica) + TX, Euschistus heros + TX, Piezodorus lituratus + TX, Southern green stink bug (Nezara viridula) + TX, Dichelops furcatus + TX, Lygus spp. + TX, Streptocorisa acuta + TX, Brown marmorated stink bug (Halyomorpha halys) + TX, Onion thrips (Thrips tabaci) + TX, Tea tree thrips (Scirtothrips dorsalis) + TX, Western flower thrips (Frankliniella occidentalis) + TX, Boll weevil (Anthonomus grandis) + TX, Meligethes aeneus + TX, Phyllotreta spp + TX, Colorado potato beetle (Leptinotarsa ​​decemLineata) + TX, tobacco whitefly (Bemisia tabaci) + TX, greenhouse whitefly (Trialeurodes vaporariorum) + TX, cotton aphid (Aphis gossypii) + TX and green peach aphid (Myzus persicae) + TX.

[0258] The compounds of formula (I), (IA), (I-A1) or (I-A2) or one compound selected from the group consisting of the compounds shown in Tables A1 to A4 or compounds selected from P-1 to P-9 in Table P (described below) or salts thereof are particularly suitable for controlling the pests listed in the following tables in the crops listed in the tables.

[0259] [Table 7-1]

[0260] [Table 7-2]

[0261] [Table 7-3]

[0262] [Table 7-4]

[0263] [Table 7-5]

[0264] [Table 7-6]

[0265] [Table 7-7]

[0266] [Table 7-8]

[0267] [Table 7-9]

[0268] In a preferred embodiment of each aspect, compound TX (the abbreviation "TX" refers to one compound selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 shown in Table P (described below)) controls one or more of the following: Spodoptera spp. (e.g., Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Codling moth, Cydia pomonella, Lobesia spp., Tortrix spp., Bean borer (Maruca vitrata), Chrysodeixis includens, Cutthroat moth (Agrotis ipsilon), Corn moth (Elasmopalpus lignosellus), Dalbulus maidis, Flea beetle (Phyllotreta spp.), Japanese beetle (Popillia japonica), Japanese corn borer (Scirpophaga incertulas), Rice stem borer (Chilo suppressalis), Rice leaf borer (Cnaphalocrosis medinalis), Brown planthopper (Nilaparvata lugens), Sogatella furcifera frucifera), small brown planthopper (Laodelphax striatellus), green rice leafhopper species (Nephotettix spp.), tobacco whitefly (Bemisia tabaci), greenhouse whitefly (Trialeurodes vaporariorum), cotton aphid (Aphis gossypii) and green peach aphid (Myzus persicae); for example, Spodoptera spp (e.g., Spodoptera frugiperda, Spodoptera littoralis) + TX, cotton bollworm (Helicoverpa armigera) + TX, Heliothis virescens + TX, eggplant borer (Leucinodes orbonalis) + TX, tomato tooth moth (Tuta absoluta) + TX, diamondback moth (Plutella xylostella) + TX, codling moth (Cydia pomonella) + TX, Lobesia spp. spp.) + TX, Tortrix spp. + TX, Bean leaf moth (Maruca vitrata) + TX, Chrysodeixis includens + TX, Cutthroat moth (Agrotis ipsilon) + TX, Corn moth (Elasmopalpus lignosellus) + TX, Dalbulus maidis + TX, Flea beetle species (Phyllotreta spp.) + TX, Japanese beetle (Popillia japonica) + TX, Japanese corn beetle (Scirpophaga incertulas) + TX, Rice stem borer (Chilo suppressalis) + TX, Rice leaf borer (Cnaphalocrosis medinalis) + TX, Brown planthopper (Nilaparvata lugens) + TX, Sogatella frucifera + TX, Laodelphax striatellus + TX, Nephotettix spp.) + TX, Tobacco whitefly (Bemisia tabaci) + TX, Greenhouse whitefly (Trialeurodes vaporariorum) + TX, Cotton aphid (Aphis gossypii) + TX and Green peach aphid (Myzus persicae) + TX.

[0269] The compounds according to the present invention may have any number of advantages, including, inter alia, advantageous levels of biological activity for protecting plants from insects or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, advantageous activity spectrum, improved safety profile against above- and below-ground non-target organisms (fish, birds, bees, etc.), improved physicochemical properties, or improved biodegradability). Particularly surprisingly, it has been found that certain compounds of formula (I) can exhibit advantageous safety profiles against non-target arthropods, particularly honeybees, solitary bees, and bumblebees. Most specifically, this is the European honeybee (Apis mellifera).

[0270] The compound according to the present invention can be used as a pesticide in its original form, but is generally formulated into a composition in various ways using formulation adjuvants such as carriers, solvents, and surfactants.The formulation can be in various physical forms, such as dust, gel, wettable powder, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, finely emulsifiable concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or water-miscible organic solvents as carriers), 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 as they are or diluted before use.Dilution can be carried out, for example, with water, liquid fertilizer, micronutrients, organisms, oil, or solvents.

[0271] By adding other insecticidal, acaricidal and / or fungicidal active ingredients, the scope of action of the composition according to the invention can be significantly expanded and adapted to actual conditions.Mixtures of compounds of formula (I) with other insecticidal, acaricidal and / or fungicidal active ingredients may also show further surprising advantages, which can be broadly described as synergistic activity, such as improved plant resistance, reduced phytotoxicity, the ability to control insects at different developmental stages, or improved behavior during their preparation, for example, during grinding or mixing, during their storage, or during their use.

[0272] Suitable active ingredients to be added herein are, for example, those belonging to the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thiourea, juvenile hormones, formamidine, benzophenone derivatives, urea, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylurea, pyridinylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0273] Preferred combinations of compounds of formula (I) with other active substances are shown below (the abbreviation "TX" means one compound selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 listed in Table P (described below)): Adjuvants selected from the group consisting of the following substances: petroleum (synonym) (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, alphamethrin + TX, amidoflumet + TX, aminocarb + TX, azocyclotine + TX, bensultap + TX, benzoximate + TX, benzpyrimoxane + TX, β-cyfluthrin + TX X, β-cypermethrin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, S-bioallethrin + TX, bioresmethrin + TX, bistrifluron + TX, brofuranilide + TX, brofluthrinate + 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:2095470-94-1+TX, CAS number:2377084-09-6+TX, CAS number :1445683-71-5+TX, CAS number:2408220-94-8+TX, CAS number:2408220-91-5+TX, CAS number:1365070-72-9+TX, CAS number:2171099-09-3+TX, CAS number:2396747-83-2 +TX, CAS number: 2133042-31-4+TX, CAS number: 2133042-44-9+TX, CAS number: 1445684-82-1+TX, CAS number: 1445684-82-1+TX, CAS number: 1922957-45-6+TX, CAS number: 192 2957-46-7+TX, CAS number: 1922957-47-8+TX, CAS number: 1922957-48-9+TX, CAS number: 2415706-16-8+TX, CAS number: 1594624-87-9+TX, CAS number: 1594637-65-6+TX,CAS number:1594626-19-3+TX, CAS number:1990457-52-7+TX, CAS number:1990457-55-0+TX, CAS number:1990457-57-2+TX, CAS number:1990457-77-6+TX, CAS number:1990457- 66-3+TX, CAS number: 1990457-85-6+TX, CAS number: 2220132-55-6+TX, CAS number: 1255091-74-7+TX, CAS number: 2719848-60-7+TX, CAS number: 1956329-03-5+TX, CAS number 19 22957-45-6 + TX, CAS No. 2368920-61-8 + TX, CAS No. 2615135-05-5 + 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, cycloaniliprole + TX, cyclobutrifluram + TX, cycloprothrin + TX, cyclo Loxapride + TX, cyenopyrafen + TX, cetopyrafen (or ethopyrafen) + 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, dimpropylidaz + TX, dinactin + TX, dinocap + TX, dinotefuran + TX, di Oxabenzophos + TX, emamectin (or emamectin benzoate) + TX, empenthrin + TX, ε-monfluthrin + TX, ε-metofluthrin + TX, esfenvalerate + TX, ethion + TX, ethiprole + TX, etofenprox + TX, etoxazole + TX, famflur + TX, fenazaquin + TX, fenfluthrin + TX, phenmezodithiaz + TX, fenitrothion + TX, fenobucarb + TX, fenothiocarb + TX, fenoxycarb + TX, fenpropathrin + TX, fenpyroximate + TX,Fensulfothion +TX, Fenthion +TX, Fentin acetate +TX, Fenvalerate +TX, Fipronil +TX, Flormetoquin +TX, Flonicamid +TX, Fluacrypyrim +TX, Fluazaindolizine +TX, Fluazuron +TX, Flubendiamide +TX, Flubenzimine +TX, Fluchlordiniliprole +TX, Flucythrinate +TX, Flucycloclone +TX, Flucythrinate +TX, Fluensulfone +TX, Flufenerim +TX, Flufenprox +TX, Flufiprole +TX, Fluhexafon + TX, flumethrin + TX, fluopyram + TX, flupentiofenox + TX, flupyradifurone + TX, flupiroxystrobin + TX, flupirimin + TX, fluralaner + TX, fluvalinate + TX, fluxamethamide + TX, fosthiazate + TX, gamma-cyhalothrin + TX, guadipyr + TX, halofenozide + TX, halfenprox + TX, heptafluthrin + TX, hexythiazox + TX, hydramethylnon + TX, imicyafos + TX, imidacloprid + TX, imiprothrin + TX, indazapiroxamet + TX , indoxacarb +TX, iodomethane +TX, iprodione +TX, isocycloceram +TX, isothioate +TX, ivermectin +TX, κ-bifenthrin +TX, κ-tefluthrin +TX, λ-cyhalothrin +TX, redoprona +TX, lepimectin +TX, lotilaner +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, Profluthrin +TX, Propargite +TX, Propetamphos +TX, Propoxur +TX, Prothiofos +TX,Protrifenbute +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, Spirobudifen +TX, Spirodiclofen +TX, Spiromesifen +TX, Spiropydione +TX, Spirotetramat +TX, Spidoxamat +TX, Sulfoxaflor +TX, Tebufenozide +TX, Tebufenpyrad +TX, Tebupirimifos +TX, Tefluthrin +TX, Temephos +TX, Tetraclofen Lantraniliprole +TX, tetradifon +TX, tetramethrin +TX, tetramethylfluthrin +TX, tetranactin +TX, tetraniliprole +TX, θ-cypermethrin +TX, thiacloprid +TX, thiamethoxam +TX, thiodicarb +TX, thiocyclam +TX, thiofanox +TX, thiometon +TX, thiosultap +TX, tigoraner +TX, thiolantraniliprole +TX, thioxazaphen +TX, tolfenpyrad +TX, toxaphene +TX, tralomethrin +TX, transfluthrin +TX, triazamate +TX, triazophos +TX, trichlorfon +TX, trichloronate +TX, trifluenfuronate +TX, triflumezopyrim +TX, cyclopyrazoflurane +TX, ζ, -Cypermethrin +TX, Seaweed extract and molasses-derived fermentation product +TX, Seaweed extract and molasses-derived fermentation product containing urea +TX, Amino acids +TX, Potassium and molybdenum and EDTA-chelated manganese +TX, Seaweed extract and plant fermentation product +TX, Seaweed extract and plant fermentation product containing plant hormones +TX, Vitamins +TX, EDTA-chelated copper +TX, Zinc +TX, Iron +TX, Azadirachtin +TX, Bacillus aizawai +TX, Bacillus chitinosporus AQ746 (NRRL Accession No. B-21618) +TX, Bacillus firmus +TX, Bacillus kurstaki +TX, Bacillus mycoides 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 No. 55609) + TX, Bacillus subtilis (unspecified) + TX, Bacillus subtilis AQ153 (ATCC Accession No. 55614) + TX, Bacillus subtilis AQ30002 (NRRL Accession No. B-50421) + TX, Bacillus subtilis AQ30004 (NRRL Accession No. B-50455) + TX, Bacillus subtilis AQ713 (NRRL Accession No. 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 subspecies kurstaki BMP 123 + TX, Beauveria bassiana + TX, D-limonene + TX, granulosis virus + 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 No. 30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, Neem Tree-Derived Products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usugae usgae + TX, p-cymene + TX, diamondback moth (Plutella xylostella) granulosis virus + TX, diamondback moth (Plutella xylostella) nuclear polyhedrosis virus + TX, polyhedrosis virus + TX, pyrethrum + TX, QRD 420 (terpenoid mixture) + TX, QRD 452 (terpenoid mixture) + TX, QRD 460 (terpenoid mixture) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Spodoptera frugiperda nuclear polyhedrosis virus + TX, Streptomyces galbus galbus (NRRL Accession No. 30232) + TX, Streptomyces sp. (NRRL Accession No. B-30145) + TX, terpenoid mixture + TX, Verticillium spp. + TX.

[0274] An algicide selected from the group consisting of bethoxazin [CCN] + TX, copper octanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, sibutrin [CCN] + TX, dichloren (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) + TX, and triphenyltin hydroxide (IUPAC name) (347) + TX.

[0275] A nematicide selected from the group consisting of: abamectin (1) + TX, crufomate (1011) + TX, cyclobutrifluram + TX, doramectin (also known as CCN) + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (also known as CCN) + TX, ivermectin (also known as CCN) + TX, milbemycin oxime (also known as CCN) + TX, moxidectin (also known as CCN) + TX, piperazine (also known as CCN) + TX, selamectin (also known as CCN) + TX, spinosad (737) + TX, and thiophanate (1435) + TX.

[0276] An avianicide selected from the group consisting of the following substances: chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) + TX, and strychnine (745) + TX.

[0277] A bactericide selected from the group consisting of 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, dodisin (1112) + TX, fenaminosulf (1144) + TX, and formaldehyde (404) + TX. X, hydralgafen (synonym) [CCN] + TX, 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 (synonym) [CCN] + TX.

[0278] A biological agent selected from the group consisting of the following: Adoxophyes orana granulosis virus (12) + TX, Agrobacterium radiobacter (13) + TX, Amblyseius spp. (19) + TX, Anagrapha falcifera nucleopolyhedrovirus (28) + TX, Anagrus atomus (29) + TX, Aphelinus abdominalis (33) + TX, Aphidius colemani (34) + TX, Aphidoletes aphidimiza (35) + TX, Aphidoletes aphidimiza (36) + TX, Aphidoletes aphidimiza (37) + TX, Aphidoletes aphidimiza (38) + TX, Aphidoletes aphidimiza (39) + TX, Aphidoletes aphidimiza (40) + TX, Aphidoletes aphidimiza (41) + TX, Aphidoletes aphidimiza (42) + TX, Aphidoletes aphidimiza (43) + TX, Aphidoletes aphidimiza (44) + TX, Aphidoletes aphidimiza (45) + TX, Aphidoletes aphidimiza (46) + TX, Aphidoletes aphidimiza (47) + TX, Aphidoletes aphidimiza (48) + TX, Aphidoletes aphidimiza (49 ...1) + TX, Aphidoletes aphidimiza (42) + TX, A aphidimyza (synonym) (35) + TX, Autographa californica nuclear polyhedrosis virus (synonym) (38) + TX, Bacillus firmus (synonym) (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. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (scientific name) (51) + TX thuringiensis 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 (synonym) (53) + TX, Beauveria brongniartii (synonym) (54) + TX, Chrysoperla carnea (synonym) (151) + TX, Cryptolaemus montrouzieri (synonym) (178) + TX, Cydia pomonella granulosis virus (synonym) (191) + TX, Dacnusa sibirica (synonym) (212) + TX, Diglyphus isaea (synonym) (254) + TX, Encarsia formosa (scientific name) (293) + TX, Eretmocerus eremicus (synonym) (300) + TX, Helicoverpa zea nuclear polyhedrosis virus (synonym) (431) + TX, Heterorhabditis bacteriophora and H. megidis (synonym) (433) + TX, Hippodamia convergens (synonym) (442) + TX, Leptomastix dactylopii (synonym) (488) + TX, Macrolophus caliginosus (synonym) (491) + TX, Mamestra brassicae nuclear polyhedrosis virus (synonym) (494) + TX, Metaphycus helvolus (synonym) (522) + TX, Metarhizium anisopliae var. acridum (scientific name) (523) + TX, Metarhizium anisopliae var. anisopliae (scientific name) (523) + TX, pine sawfly (Neodiprion sertifer) nuclear polyhedrosis virus and Neodiprion lecontei (N.lecontei nuclear polyhedrosis virus (synonym) (575) + TX, Orius spp. (synonym) (596) + TX, Paecilomyces fumosoroseus (synonym) (613) + TX, Phytoseiulus persimilis (synonym) (644) + TX, Spodoptera exigua multicapsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (synonym) (742) + TX, Steinernema carpocapsae (synonym) (742) + TX, Steinernema feltiae (scientific name) (742) + TX feltiae (synonym) (742) + TX, Steinernema glaseri (synonym) (742) + TX, Steinernema riobrave (synonym) (742) + TX, Steinernema riobravis (synonym) (742) + TX, Steinernema scapterisci (synonym) (742) + TX, Steinernema spp. (synonym) (742) + TX, Trichogramma spp. (synonym) (826) + TX, Typhlodromus occidentalis occidentalis (alias) (844) + TX, Verticillium lecanii (alias) (848) + TX.

[0279] A soil sterilizer selected from the group consisting of the following substances: iodomethane (IUPAC name) (542) + TX and methyl bromide (537) + TX.

[0280] A chemosterilant selected from the group consisting of: afolate [CCN] + TX, bisazir (alias) [CCN] + TX, busulfan (alias) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alias) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl afolate [CCN] + TX, molzide [CCN] + TX, penfluron (alias) [CCN] + TX, tepa [CCN] + TX, thiohempa (alias) [CCN] + TX, thiotepa (alias) [CCN] + TX, tretamim (alias) [CCN] + TX, and uredepa (alias) [CCN] + TX.

[0281] Insect pheromones selected from the group consisting of: (E)-dec-5-enyl-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-4,10-dienyl-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)-hexadec-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 (I (IUPAC name) (783) + TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784) + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283) + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradec-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 (alias) [CCN] + TX, Brevicomin (alias) [CCN] + TX, Codrelure (alias) [CCN] + TX, Codlemone (alias) (167) + TX, Curea (alias) (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-8,10-Dien-1-yl acetate (IUPAC name) (284) + TX, Dominicale (alias) [CCN] + TX, Ethyl 4-methyloctanoate (IUPAC name) (317) + TX, Eugenol (alias) [CCN] + TX, Frontalin (alias) [CCN] + TX, Gossyplure® (alias; 1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl acetate) (420) + TX, Grand Rule (4 21) + TX, Grand Lure I (alias) (421) + TX, Grand Lure II (alias) (421) + TX, Grand Lure III (alias) (421) + TX, Grand Lure IV (alias) (421) + TX, Hexalure [CCN] + TX, Ipsdienol (alias) [CCN] + TX, Ipsenol (alias) [CCN] + TX, Japonirure (alias) (481) + TX, Lineatin [CCN] + TX, Littlea [CCN] + TX, Looplua [CCN] + TX, Me Dolure [CCN] + TX, Megatomoic acid (synonym) [CCN] + TX, Methyl eugenol (synonym) (540) + TX, Muscalure (563) + TX, Octadeca-2,13-dien-1-yl acetate (IUPAC name) (588) + TX, Octadeca-3,13-dien-1-yl acetate (IUPAC name) (589) + TX, Olfuralure (synonym) [CCN] + TX, Orictalure (synonym) (317) + TX, Ostramon (synonym) [CCN] + TX, Cigrul [CCN] + TX, Soldigin (synonym) (736) + TX, Sulcatol (synonym) [CCN] + TX, Tetradec-11-en-1-yl acetate (IUPAC name) (785) + TX, Trimedulla (synonym) (839) + TX, Trimedulla A (synonym) (839) + TX, Trimedulla B1 (synonym) (839) + TX, Trimedulla B2 (synonym) (839) + TX, Trimedulla C (synonym) (839) + TX, and Trancol (synonym) [CCN] + TX.

[0282] An insect repellent selected from the group 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, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, mesoquin-butyl (1276) + TX, methyl neodecanoamide [CCN] + TX, oxamate [CCN] + TX, and picaridin [CCN] + TX.

[0283] A molluscicide selected from the group consisting of: bis(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloetocarb (999) + TX, copper acetoarsenate [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, iron phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-o Ramin (576) + TX, pentachlorophenol (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) + TX, triphenyltin hydroxide (IUPAC name) (347) + TX, and pyriprole [394730-71-3] + TX.

[0284] A nematicide selected from the group consisting of the following substances: AKD-3088 (compound code) + TX, 1,2-dibromo-3-chloropropane (IUPAC name / chemical abstract name) (1045) + TX, 1,2-dichloropropane (IUPAC name / chemical abstract name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene-1,1-dioxy d (IUPAC name / Chemical Abstract 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 (alias) (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 (alias) + 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 (alias) (210) + TX , Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidaphos (1044) + TX, Diclofenthion (1051) + TX, Dicrifos (alias) + TX, Dimethoate (262) + TX, Doramectin (alias) [CCN] + TX, Emamectin (291) + TX, Emamectin Benzoate (291) + TX, Eprinomectin (alias) [CCN] + TX, Ethoprophos (312) + TX, Ethylenediamine Romido (316) + TX, Fenamiphos (326) + TX, Fenpyrad (alias) + TX, Fensulfothion (1158) + TX, Fosthiazate (408) + TX, Fostietan (1196) + TX, Furfural (alias) [CCN] + TX, GY-81 (development code) (423) + TX, Heterofos [CCN] + TX, Iodomethane (IUPAC name) (542) + TX, Isamidophos (1230) + TX, Isazophos (1231) + TX, Ibe Lumectin (alias) [CCN] + TX, Kinetin (alias) (210) + TX, Mecarfone (1258) + TX, Metam (519) + TX, Metam-potassium (alias) (519) + TX, Metam-sodium (519) + TX, Methyl bromide (537) + TX, Methyl isothiocyanate (543) + TX, Milbemycin oxime (alias) [CCN] + TX, Moxidectin (alias) [CCN] + TX, Myrothecium verrucaria (Myrotheciumverrucaria composition (synonym) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, cebufos (synonym) + TX, selamectin (synonym) [CCN] + TX, spinosad (737) + TX, terbufos (synonym) + TX, terbufos (773) + TX, tetrachlorothiazol-3 Ophene (IUPAC name / chemical abstract name) (1422) + TX, Thiafenox (alias) + TX, Thionazine (1434) + TX, Triazophos (820) + TX, Triazuron (alias) + TX, Xylenol [CCN] + TX, YI-5302 (compound code) + TX, Zeatin (alias) (210) + TX, Fluensulfone [318290-98-1] + TX, and Fluopyram + TX.

[0285] A nitrification inhibitor selected from the group consisting of potassium ethylxanthate [CCN] + TX and nitrapyrin (580) + TX.

[0286] A plant activator selected from the group consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) + TX, and giant knotweed (Reynoutria sachalinensis) extract (synonym) (720) + TX.

[0287] Rodenticides selected from the group consisting of: 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, anthraquinone (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemicarbamate (912) + TX, brodifacoum (89) + TX, bromadiolone (α -Bromadiolone) + TX, Bromethalin (92) + TX, Calcium cyanide (444) + TX, Chloralose (127) + TX, Chlorophacinone (140) + TX, Cholecalciferol (alias) (850) + TX, Coumachlor (1004) + TX, Coumafuryl (1005) + TX, Coumatetralyl (175) + TX, Crimidine (1009) + TX, Difenacoum (246) + TX, Difethialone (249) + TX, Diphacinone (273) + TX, Ergocalciferol acetamide (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, fosacetin methicone (1336) + TX, phosphine (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) + TX, and zinc phosphide (640) + TX.

[0288] A synergist selected from the group consisting of: 2-(2-butoxyethoxy)ethyl piperonate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol and nerolidol (aliases) (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) + TX, and sulfoxide (1406) + TX.

[0289] An animal repellent selected from the group 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] + TX, and ziram (856) + TX.

[0290] A virucidal agent selected from the group consisting of: Imanin (alias) [CCN] + TX and Ribavirin (alias) [CCN] + TX.

[0291] A wound dressing selected from the group consisting of: mercuric oxide (512) + TX, octhilinone (590) + TX, and thiophanate-methyl (802) + TX.

[0292] Bioactive substances selected from the following substances: 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + 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 oxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromocyclen + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butylpyridaben + TX, calcium polysulfide + TX, camphechlor + TX, carbanolate + TX, carbophenothion + TX, cymiazole + TX, chinomethionate + TX, chlorbenesid + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorphenetole +TX, Chlorfenson +TX, Chlorfensulfide +TX, Chlorobenzilate +TX, Chlormebform +TX, Chlormethiuron +TX, Chloropropylate +TX, Chlorthiophos +TX, Cinerin I +TX, Cinerin II +TX, Cinerin +TX, Closantel +TX, Coumaphos +TX, Crotamiton +TX, Crotoxyphos +TX, Kufraneb +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-methyl sulfone + 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, Dinotervon + TX, Dioxathion + TX, Diphenylsulfone + TX, Disulfiram + TX, DNOC + TX, Dofenapine + TX,Doramectin + TX, Endothion + TX, Eprinomectin + TX, Ethoate-methyl + TX, Etrimphos + TX, Fenazaflor + TX, Fenbutatin oxide + TX, Fenthiocarb + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubenzimine + TX, Flucycloxuron + TX, Fluenethyl + TX, Fluobenside + TX, FMC 1137+TX, Formetanate+TX, Formetanate Hydrochloride+TX, Formoparanate+TX, Gamma-HCH+TX, Gliodin+TX, Halfenprox+TX, Hexadecyl Cyclopropanecarboxylate+TX, Isocarbophos+TX, Jasmolin I+TX, Jasmolin II+TX, Jodofenphos+TX, Lindane+TX, Malonoben+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, nifururidide +TX, nikkomycin +TX, nitrilacarb +TX, nitrilaca Lube 1:1 zinc chloride complex +TX, omethoate +TX, oxydeprophos +TX, oxydisulfoton +TX, pp'-DDT +TX, parathion +TX, permethrin +TX, fenkapton +TX, phosalone +TX, phospholan +TX, phosphamidon +TX, polychloroterpenes +TX, polynactin +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, Diflavidazine + TX, Taufluvalinate + TX,TEPP+TX, Terbam+TX, Tetradifon+TX, Tetrasul+TX, Thiafenox+TX, Thiocarboxim+TX, Thiofanox+TX, Thiometon+TX, Thioquinox+TX, Thuringensin+TX, Triamiphos+TX, Triatene+TX, Triazophos+TX, Triazuron+TX, Trifenofos+TX, Trinactin+TX, Vamidothion+TX, Vaniliprole+TX, Bethoxadin+TX, Copper Octanoate +TX, copper sulfate +TX, sibutrin +TX, dichloren +TX, dichlorophen +TX, endothall +TX, fentin +TX, hydrated lime +TX, nabam +TX, quinoclamine +TX, quinonamide +TX, simazine +TX, triphenyltin acetate +TX, triphenyltin hydroxide +TX, crufomate +TX, piperazine +TX, thiophanate +TX, chloralose +TX, fenthion +TX, pyridin-4-amine +TX, 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, dodisin + TX, fenaminosulf + TX, formaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin hydrochloride monohydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, hydroxyquinoline potassium sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, anafas orana (Adoxophyes orana granulosis virus + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera nuclear polyhedrosis virus + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica nuclear polyhedrosis virus + TX, Bacillus sphaericus Neide + TX, Beauveria bronniartii brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Codling moth (Cydia pomonella) granulosis virus + 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 nucleopolyhedrovirus + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae var. anisopliae + TX, pine sawfly (Neodiprion sertifer) nuclear polyhedrosis virus and Neodiprion lecontei nuclear polyhedrosis virus + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX,Typhlodromus occidentalis + TX, Verticillium lecanii + TX, Afolate + TX, Bisazilyl + TX, Busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl Afolate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-Deca-5-en-1-yl acetate and (E)-Deca-5-en-1-ol + TX, (E)-Trideca-4-en-1-yl acetate + TX, (E)-6-Methylheptyl acetate + TX To-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)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + T X, (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, codrellet + TX, codlemone + TX, Cure + TX, Disparlua + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8,10-dien-1-yl acetate + TX, Dominicale + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grand Lure + TX, Grand Lure I + TX, Grand Lure II + TX, Grand Lure III + TX, Grand Lure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX,Japonirure + TX, Lineatin + TX, Littlea + TX, Looplua + TX, Medula + TX, Megatomoic Acid + TX, Methyleugenol + TX, Muscalua + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfuralua + TX, Orictalua + TX, Ostramon + TX, Sigulure + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedula + TX, Trimedula A + TX, Trimedula B 1+TX, Trimedlure B2+TX, Trimedlure C+TX, Trancol+TX, 2-(octylthio)ethanol+TX, Butopyronoxyl+TX, Butoxy(polypropylene glycol)+TX, Dibutyl adipate+TX, Dibutyl phthalate+TX, Dibutyl succinate+TX, Diethyltoluamide+TX, Dimethyl carbate+TX, Dimethyl phthalate+TX, Ethyl hexanediol+TX, Hexamide+TX, Methoxybutyl+TX, Methylneodecanamide+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-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl (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-yn-1-yl)aminophenyl methyl carbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX,4-Methyl(prop-2-yn-1-yl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, allylxycarb + 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, barthrin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, β-cyfluthrin +TX, β-cypermethrin +TX, bioethanometrin +TX, biopermethrin +TX, bis(2-chloroethyl) ether +TX, borax +TX, bromfenbi Nphos + 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, Cevadin + TX, Chlorbicyclen + TX, Chlordane + TX, Chlordecone + TX, Chloroform + TX, Chloropicrin + TX, Chlorphoxim + TX, Chlorprazofos + TX , cis-resmethrin + TX, cismethrin + TX, clocisrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, chumithoate + TX, cryolite + TX, CS708 + TX, cyanofenphos + TX, cyanophos + TX, ciclethrin + TX, cithioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamidaphos + TX, dikapton + TX, di Clofenthion + 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, Ethaphos + TX, Ethiofencarb + TX, Ethyl formate + TX, Ethylene dibromide + TX, Ethylene dichloride + TX, Ethylene oxide + TX, EXD + TX, Fenchlorphos + TX, Fenetacarb + TX, Fenitrothion + TX, Fenoxacrim + TX, Fenpyrithrin + TX, Fensulfothion + TX, Fenthion ethyl + TX, Flucofuron + TX, Fosmetilan + TX, Fospirate + TX, Fostietan + TX, Furathiocarb + TX, Freslin + TX, Guazatine + TX, Guazatine acetate + TX, Sodium tetrathiocarbonate Um+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterofos+TX, HHDN+TX, Hydrogen cyanide+TX, Hychincarb+TX, IPSP+TX, Isazophos+TX, Isobenzane+TX, Isodrin+TX, Isofenphos+TX, Isolane+TX, Isoprothiolane+TX, Isoxathion+TX, Juvenile Hormone I+TX, Juvenile Hormone II+TX, Juvenile 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, methanesulfonyl fluoride +TX, methocrotophos +TX, methoprene +TX, mesotrin +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-ethyl ethylphosphonothioate + 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'-tetrapropyl dithiopyrophosphate + 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, Primidophos +TX, Profluthrin +TX, Promecarb +TX, Prothiofos +TX, Pyrazophos +TX, Pyresmethrin +TX, Quassia +TX, Quinalphos-methyl +TX, Quinothione +TX, Lafox Sanid +TX, Resmethrin +TX, Rotenone +TX, Kadesrin +TX, Riania +TX, Ryanodine +TX, Sabadila +TX, Shladan +TX, Cebufos +TX, SI-0009 +TX, Tiapronil +TX, Sodium arsenite +TX, Sodium cyanide +TX, Sodium fluoride +TX, Sodium hexafluorosilicate +TX, Sodium pentachlorophenoxide +TX, Sodium selenate +TX, Sodium thiocyanate +TX, Sulcofuron +TX, Sulcofuron-sodium +TX, Sulfuryl fluoride +TX, Sulprofos +TX, Tar Oil +TX, Thazimcarb +TX, TDE +TX, Tebupirimfos +TX, Temephos +TX, Teralethrin +TX, Tetrachloroethane +TX, Cyclofos +TX, Thiocyclam +TX, Thiocyclam Hydrogen Oxalate +TX, Thionazine +TX, Thiosultap +TX, Thiosultap-Sodium +TX, Tralomethrin +TX, Transpermethrin +TX, Triazamate +TX, Trichlormetaphos-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, Meperfluthrin + TX, Tetramethylfluthrin + TX, Bis(tributyltin) oxide + TX, Bromoacetamide + TX, Iron(III) phosphate + TX, Niclosamide olamine + TX, Tributyltin oxide + TX, Pyrimorph + TX, Trifenmorph + 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, anicifluprine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + 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, antu +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, fluoroacetoacetate Amide + 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, valbutin + TX, MGK 264+TX, piperonyl butoxide+TX, piprotal+TX, propyl isomer+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, chlorinconazide+TX, mercury oxide+TX, thiophanate methyl+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, proc Loraz + 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, pyrimidol Metanil + TX, Fenpiclonil + TX, Fludioxonil + TX, Benalaxyl + TX, Furalaxyl + TX, Metalaxyl + TX, R-Metalaxyl + TX, Ofurace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazole + TX, Chlozolinate + TX, Diclozolin + TX, Mycrozolin + TX, Procymidone + TX, Vinclozolin + TX, Boscalid + TX, Carboxin + TX, Fenfuram + TX, Flutolanil + TX, Mepronil + TX, Oxycarboxin + TX, Pe Enthiopyrad + TX, Thifluzamide + TX, Dodin + TX, Iminoctadine + TX, Azoxystrobin + TX, Dimoxystrobin + TX, Enestrobulin + TX, Phenaminestrobin + TX, Flufenoxystrobin + TX, Fluoxastrobin + TX, Kresoximmethyl + TX, Metominostrobin + TX, Trifloxystrobin + TX, Orysastrobin + TX, Picoxystrobin + TX, Pyraclostrobin + TX, Pyrametstrobin + 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, Nitrothar-isopropyl + TX, Edifenphos + TX, Iprobenfos + TX, Fosdifen + TX, Tolclofos-methyl + TX, Anilazine + TX, Benthiavalicarb + TX, Brassitidin-S + TX, Chloroneb + ​​TX, Chlorothalonil + TX, Cyflufenamid + TX, Cyflufenamid Moxanil +TX, cyclobutrifluram +TX, diclocymet +TX, diclomedine +TX, dicloran +TX, diethofencarb +TX, dimethomorph +TX, flumorph +TX, dithianon +TX, ethaboxam +TX, etridiazole +TX, famoxadone +TX, fenamidone +TX, fenoxanil +TX, ferimzone +TX, fluazinam +TX, flumethylsulfolim +TX, fluopicolide +TX, fluoxythioconazole +TX, flusulfamide +TX, fluxapyroxad +TX, fenhexa amide +TX, fosetylaluminum +TX, hymexazole +TX, iprovalicarb +TX, cyazofamid +TX, methasulfocarb +TX, metrafenone +TX, pencycuron +TX, phthalide +TX, polyoxin +TX, propamocarb +TX, pyribencarb +TX, proquinazide +TX, pyroquinolone +TX, pyriophenone +TX, quinoxyfen +TX, quintozene +TX, tiadinil +TX, triazoxide +TX, tricyclazole +TX, triforine +TX, validamycin +TX, valifenalate +T X, zoxamide + TX, mandipropamide + TX, fluveneteram + 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-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-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, Diclobenziazox + 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, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylidene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, impirfluxam + TX, torolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl N'-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]methanesulfonate + 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)pyridyl Ridazine + 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]tetrazole-5 -one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, methallylpicoxamide + TX, tebufloquine + TX, ipflufenoquine + TX, quinofumelin + TX, isofetamide + TX, 1-[[4-[[2-(trifluoromethyl)pyrazole methyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the method described in WO 2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-propen-1-yloxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the method described in WO 2020 / 056090), N-[[4-[1-(4-cyclopropyl-2,Methyl N-[[4-[1-(2,6-difluoro-4-isopropylphenyl)pyrazol-4-yl]-2-methylphenyl]methyl]carbamate + TX (which can be prepared by the method described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropylphenyl)pyrazol-4-yl]-2-methylphenyl]methyl]carbamate + TX (which can be prepared by the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)pyrazol-4-yl]-2-methylphenyl]methyl]carbamate + TX 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + TX (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + TX (which can be prepared by the methods described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N- [2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + TX (which can be prepared by the method described in WO 2020 / 109391), N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, benzothiostrobin + TX, phenoxyphenyl Namacril + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flufenoxadiazam + 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, Fluoxapiprolin + TX, Enoxastrobin + TX , (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methylphenoxy]-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester Methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate + TX (these compounds can be prepared by the method described in WO 2020 / 079111), methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoate + TX (these compounds can be prepared by the method described in WO 20 No. 20 / 193387), 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,1-Difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zongshenmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, seboxylamine + TX, N'-[5-bromo-2-methyl-6-[(1S)- 1-Methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'- [5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine + TX (these compounds can be prepared by the method described in WO 2015 / 155075), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine + TX methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + 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-phenylethyl)phenyl]-N-methylformamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine + TX (these compounds can be prepared by the method described in WO 2018 / 228896), N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine + TX tetrahydrofuran-2-yl]phenyl]-N-methylformamidine + 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-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3, 3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoroquinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluoro N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoroquinoline-3-carboxamide + TX, N-[[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl N-[[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoroquinoline-3-carboxamide + TX (these compounds can be prepared by the method 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)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds can be prepared by the method described in WO 2017 / 025510);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 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]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, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethyl 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 / 156 290); 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); 2-amino-6-methyl-pyridine-3-carboxylate (4-phenoxyphenyl)methyl + 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 + 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]benzenecarbothioamide + 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-methylformamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methylformamidine amidine + 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)-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 methods 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 methods described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2- ethyl]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]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 method described in WO 2018 / 202428).

[0293] Microorganisms such as Acinetobacter lwoffii + TX, Acremonium alternatum + TX, Acremonium cephalosporium + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulosis virus (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 NRRL21882 (Aflaguard®) + TX, Aspergillus spp.) + TX, Aureobasidium pullulans + TX, Azospirillum spp. (MicroAZ®, TAZO B®) + TX, Azotobacter spp. (Azotobacter) + TX, Azotobacter chroocuccum (Azotomeal®) + TX, Azotobacter cysts (Bionatural Blooming Blossoms®) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (Biostart™, formerly known as Rhizoboost™) + TX, Bacillus licheniformis strain 3086 (EcoGuard™, Green Releaf™) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe™, BioNem-WP™, VOTiVO™) + TX, Bacillus firmus strain I-1582 + TX, Bacillus macerans) + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides AQ726 strain + 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 QST2808 (Sonata®, Ballad Plus®) +TX, Bacillus spahericus (VectoLex®) +TX, Bacillus spp. +TX, Bacillus spp. AQ175 +TX, Bacillus spp. AQ177 +TX, Bacillus spp. AQ178 +TX, Bacillus subtilis Bacillus subtilis strain QST713 (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus subtilis strain QST714 (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 strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis (Bacillus thuringiensis) Cry 2Ae+TX, Bacillus thuringiensis) Cry1Ab+TX, Bacillus thuringiensis subsp. aizawai) GC 91 (Agree®)+TX, Bacillus thuringiensis subsp. israeliensis (Bacillus thuringiensis subsp.israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis subsp. kurstaki (Javelin®, Deliver®, CryMax®, Bondide®, Scutella WP®, Turilav WP®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX, Bacillus thuringiensis BD#32 strain + TX, Bacillus thuringiensis AQ52 strain + TX, Bacillus thuringiensis var. aizawai (XenTari®, DiPel®) + TX, bacterial spp.) (GROWMEND®, GROWSWEET®, Shootup®) + TX, Clavipacter michiganensis bacteriophage (AgriPhage®) + TX, Bakflor® + TX, Beauveria bassiana (Beaugenic®, Brocaril WP®) + TX, Beauveria bassiana GHA (Mycotrol ES®, Mycotrol O®, BotaniGuard®) + TX, Beauveria brongniartii (Engerlingspilz®, Schweizer Beauveria®, 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®, Intercept®, 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 pulcherrima + TX, Candida reukaufii + TX, Candida saitoana (Bio-Coat®, 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) strain PRAA4-1T (Grandevo®)+TX, Cladospoli. Cladosporium cladosporioides + TX, Cladosporium oxysporum + TX, Cladosporium 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 granulosis virus (Cryptex®) + TX, Cupriavidus campinensis + TX, Codling moth (Cydia pomonella) granulosis virus (CYD-X®) + TX, Codling moth (Cydia pomonella granulosis virus (Madex®, Madex® Plus®, Madex® Max, Carpovirusine Evo2®) + TX, Cylindrobasidium laeve (Stumpout®) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae species + TX, Entomophtora virulenta (Vektor®) + TX, Epicoccum nigrum nigrum) + TX, Epicoccum 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®, Prestop®) + TX, Gliocladium roseum roseum + TX, Gliocladium spp. (SoilGard®) + TX, Gliocladium virens (Soilgard®) + TX, Granulosis virus (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, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, 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, Mycorrhizal fungi (Mycorrhizae spp.) (AMykor®, 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®, 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, Pasteurella spp. (Econem®) + TX, Pasteurella nishizawae + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart®, 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, Phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofaciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugata + TX, Pseudomonas fluorescens strain A506 (BlightBan A506®) + TX, Pseudomonas putida + TX, Pseudomonas reactans + TX, Pseudomonas species 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®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp. + TX, Rhizobia (Dormal®, Vault®) + TX, Rhizoctonia + TX, Rhodococcus globerrus globerulus AQ719 strain + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula spp. + TX, Rhodotorula glutinis + TX, 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®, Spexit®) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp. + TX, Sordaria fimicola + TX, Spodoptera littoralis nuclear polyhedrosis virus (Littovir®) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces 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 TH382 + TX, Trichoderma harzianum rifai (Mycostar®) + TX, Trichoderma harzianum T-22 (Trianum-P®, PlantShield HC®, RootShield®, Trianum-G®) + TX, Trichoderma harzianum harzianum) T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp.) LC52 (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 viride strain ICC080 (Remedier®) + TX, Trichosporon 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 supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Verticillium lecanii lecanii (Mycotal®, Vertalec®) + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv. Poae (Camperico®) + TX, Xenorhabdus bovienii + TX, Xenorhabdus nematophilus + TX.

[0294] Plant extracts such as: pine oil (Retenol®) + TX, azadirachtin (Plasma Neem Oil®, AzaGuard®, MeemAzal®, Molt-X®, Botanical IGR (Neemazad®, Neemix®)) + TX, canola oil (Lilly Miller Vegol®) + TX, American ant's weed (Chenopodium ambrosioides near ambrosioides) (Requiem®) + TX, chrysanthemum (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, Pedaliaceae oil (Nematon®) + TX, pyrethrins + TX, quillaja bark extract (Quillaja saponaria) (NemaQ®) + TX, giant knotweed (Reynoutria sachalinensis) (Regalia®, Sakalia®) + TX, rotenone (Eco Roten®) + TX, Rutaceae plant extract (Soleo®) + TX, soybean oil (Ortho ecosense®) +TX, Tea Tree (Melaleuca alternifolia) Extract (also known as Tea Tree Oil) (TimorexGold®) +TX, thyme oil +TX, AGNIQUE® MMF +TX, BugOil® +TX, rosemary, sesame, peppermint, thyme and cinnamon extract mixture (EF 300®) +TX, clove, rosemary and peppermint extract mixture (EF 400®) +TX, clove, peppermint, garlic oil and mint mixture (Soil Shot®) +TX, kaolin (Screen®) +TX, brown algae-derived storage glucan (Laminarin®) +TX.

[0295] Pheromones such as the following: Blackheaded Fireworm Pheromone (3M Sprayable Blackheaded Fireworm Pheromone®) + TX, Codling Moth Pheromone (Paramount dispenser-(CM) / Isomate C-Plus®) + TX, Grapeberry Moth Pheromone (3M MEC-GBM Sprayable Pheromone®) + TX, Tortricid Moth Pheromone (3M MEC-LR Sprayable Pheromone®) + TX, Muskamone (Snip7 Fly Bait®, Starbar Premium Fly Bait®) + TX, Oriental Fruit Moth Pheromone (3M Oriental Fruit Moth Sprayable Pheromone®) + TX, Clearwing Moth Pheromone (Isomate-P®) + TX, Tomato Tuft Moth Pheromone (3M Sprayable Pheromone®) + TX, Entostat powder (oil palm extract) (Exosex CM®) + TX, (3E,8Z,11Z)-3,8,11-tetradecatrienyl acetate + TX, (7Z,11Z,13E)-7,11,13-hexadecatrienal + TX, (E,Z)-7,9-dodecadien-1-yl acetate + TX, 2-methyl-1-butanol + TX, calcium acetate + TX, Scenturion® + TX, Biolure® + TX, Check-Mate® + TX, lavandulyl senecionate + TX.

[0296] Macrobials such as: 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®, Andersoni-System®) + TX, Amblyseius californicus (Amblyline®, Spical®) + TX, Amblyseius cucumeris (Thripex®, Bugline cucumeris®) + TX, Amblyseius fallacis (Fallacis®) + TX, Amblyseius swirskii (Bugline swirskii®, Swirskii-Mite®) + TX, Amblyseius womersleyi (WomerMite®) + TX, Amitus hesperidum hesperidum + TX, Anagrus atomus + TX, Anagrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus roeckii + TXloecki + TX, Anagyrus pseudococci (Citripar®) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System®) + TX, Aphelinus abdominalis (Apheline®, Aphiline®) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar®) + TX, Aphidius ervi (Ervipar®) + TX, Aphidius gifensis gifuensis + TX, Aphidius 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®, Tripol®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritusnigritus + TX, Chrysoperla carnea (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 perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®) + TX, Cybocephalus nipponicus (Cybocephalus nipponicus) + TX, Dacnusa sibirica (Leaf-grating cone wasp) + TX, Dacnusa sibirica (Leaf-grating cone wasp) (Minusa®) + TX, Diglyphus isaea (Diminex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudatalongicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea + TX, Diglyphus isaea (Miglyphus®, Digline®) + TX, Dacnusa sibirica (DacDigline®, Minex®) + TX, Diversinervus spp. + TX, Encarsia citrina + TX, Encarsia formosa (Encarsia max®, Encarline®, En-Strip®) + TX, Eretmocerus eremicus (Enermix®) + TX, Encarsia guadeloupae + TX, Encarsia haitiensis + TX, Episyrphus balteatus (Syrphidend®) + TX, Eretmocerus siphonini + TX, Eretmocerus californicus + TX, Eretmocerus eremicus (Ercal®, Eretline e®) + TX, Eretmocerus eremicus (Bemimix®) + TX, Eretmocerus hayati + TX, Eretmocerus mundus (Bemipar®, 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®, Nemaseek®, Terranem-Nam®, Terranem®) + TX, Heterorhabditis bacteriophora (Larvanem®, B-Green®, NemAttack®, Nematop®) + TX, Heterorhabditis megidis (Nemasys H®, BioNem H®, Exhibitline hm®, Larvanem-M®) + TX, Hippodamia convergens + TX, Hypoaspis aculeifer (Aculeifer-System®, Entomite-A®) + TX, Hypoaspis miles (Hypolinem (registered trademark), Entomite-M (registered trademark)) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abdominalis ( Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar®) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly®) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N®, Macroline c®, Mirical®) + TX, Mesoseiulus longipes longipes + TX, Metaphycus flavus + TX, Metaphycus 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 fallasis fallacis + TX, Nesideocoris tenuis (NesidioBug®, Nesibug®) + TX, Ophyra aenescens (Biofly®) + TX, Oriusinsidiosus (Thripor-I®, Oriline i®) + TX, Orius laevigatus (Thripor-L®, Oriline l®) + TX, Orius majusculus (Oriline m®) + TX, Orius strigicollis (Thripor-S®) + TX, Pauesia juniperorum (Pauesia juniperorum) + TX, Pediobius foveolatus (Phasmarhabditis hermaphrodita) (Nemaslug®) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex®, 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 species) + TX, Quadrastichus spp. + TX, Rhyzobius lophanthae + TX, Rodolia cardinalis + TX, Ruminadecollate) + TX, Semielacher petiolatus + TX, Sitobion avenae (Ervibank®) + TX, Steinernema carpocapsae (Nematac C®, Millenium®, BioNem C®, NemAttack®, Nemastar®, Capsanem®) + TX, Steinernema feltiae (NemaShield®, Nemasys F®, BioNem F®, Steinernema-System®, NemAttack®, Nemaplus®, Exhibitline sf®, Scia-rid®, Entonem®) + TX, Steinernema kraussei (Nemasys L®, BioNem L®, Exhibitline srb®) + TX, Steinernema riobrave (BioVector®, BioVektor®) + TX, Steinernema scapterisci (Nematac S®) + TX, Steinernema spp. + TX, Steinernema spp. (Guardian Nematodes®) + TX, Stethorus punctilum punctillum) (Stethorus®) + TX, Tamarixia radiata + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholineb(registered trademark)), Trichogramma brassicae (Tricho-Strip(registered trademark)) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator + TX.

[0297] Other biological materials such as: 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®, Ni-HIBIT Gold CST®) +TX, fatty acids derived from natural by-products of extra virgin olive oil (FLIPPER®) +TX, ferric 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®, Rebell Amarillo®) + TX, traps (Takitrapline y+b®) + TX.

[0298] (1) an antibacterial agent selected from the group consisting of: (1.1) Bacteria, such as Bacillus mojavensis strain R3B (deposit number: NCAIM(P)B001389) from Certis USA LLC (WO 2013 / 034938) + TX, Bacillus pumilus, in particular the BU F-33 strain with deposit number NRRL 50185 (CARTISSA® from BASF, EPA registration number: 71840-19) + TX, Bacillus subtilis, in particular the QST713 / AQ713 strain (SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, NRRL deposit number B21661, U.S. Pat. No. 6,060,051) + TX, Bacillus subtilis strain BU1814 (BASF VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from SE (Deposit No. DSM 10271), Bacillus subtilis var. amyloliquefaciens strain FZB24, deposit number DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5)) (Deposit No. DSM 10271), Bacillus subtilis CX-9060 (Deposit No. DSM 10271), Bacillus sp., particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), deposit number FERM BP-8234, U.S. Pat. No. 7,094,592 (Deposit No. 7,094,592), Bacillus subtilis CX-9060 (Deposit No. DSM 10271), Bacillus sp., particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), deposit number FERM BP-8234, U.S. Pat. No. 7,094,592 (Deposit No. DSM 10271), Bacillus subtilis CX-9060 (Deposit No. DSM 10271), Bacillus subtilis CX-9060 (Deposit No. DSM 10271), Bacillus sp., particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), deposit number FERM BP-8234, U.S. Pat. No. 7,094,592 (Deposit No. DSM 10271), Bacillus subtilis CX-9 Paenibacillus sp. strains, accession numbers NRRL B-50972 or NRRL B-67129, WO 2016 / 154297 +TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) +TX; Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE from Northwest Agri Products) +TX; Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) +TX.

[0299] (1.2) fungi, such as Aureobasidium pullulans, in particular spores of the strain DSM 14940, spores of the strain DSM 14941 or a mixture of spores of the strains DSM 14940 and DSM 14941 (for example BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in WO 2011 / 151819 by Yissum Research Development Company, Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae, in particular the strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939; No. 1-3939 strain (disclosed in International Publication No. 2010 / 086790 by Lesaffre et Compagnie, France) + TX.

[0300] (2) A biological fungicide selected from the group consisting of: (2.1) Bacteria, such as Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, CA) + TX; Agrobacterium radiobacter strain K1026 (e.g., NOGALL® from BASF SE) + TX; Bacillus subtilis var. amyloliquefaciens strain FZB24, deposit number DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO, EPA registration number 70127-5) + TX; Bacillus amyloliquefaciens, in particular strain D747 (Double Nickel™, accession number FERM BP-8234, U.S. Pat. No. 7,094,592) +TX; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (accession number NRRL B-50768, WO 2014 / 028521) (available from Marrone Bio Innovations as STARGUS®) +TX; Bacillus amyloliquefaciens strain FZB42, accession number DSM23117 (available from ABiTEP, Germany as RHIZOVITAL®) +TX; Bacillus amyloliquefaciens isolate B246 (available from, e.g., University of AVOGREEN™ from Pretoria) +TX; Bacillus licheniformis, in particular strain SB3086, deposit number ATCC 55406, WO 2003 / 000051 (available as ECOGUARD™ Biofungicide and GREEN RELEAF™ from Novozymes) +TX;Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corp.) +TX; Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences' Institute of Applied Ecology) +TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (WO 2013 / 034938) +TX; Bacillus mycoides isolate, accession number B-30890 (from Certis USA LLC, BMJ Bacillus pumilus, in particular the strain QST2808 (SONATA® from Bayer CropScience LP, USA, accession number NRRL B-30087, described in U.S. Pat. No. 6,245,551) +TX; Bacillus pumilus, in particular the strain GB34 (available as Yield Shield® from Bayer AG, Germany) +TX; Bacillus pumilus, in particular the strain BU F-33, accession number NRRL 50185 (available as part of the CARTISSA product from BASF, EPA registration number 71840-19) +TX; Bacillus subtilis, in particular the strain QST713 / AQ713 (available as part of the CARTISSA product from BASF, EPA registration number 71840-19) +TX; Available from LP as SERENADE OPTI or SERENADE ASO, NRRL Accession No. B21661, described in U.S. Patent No. 6,060,051) + TX;Bacillus subtilis Y1336 (available from BioNTech, Taiwan as BIOBAC® WP, registered in Taiwan as a biofungicide under registration numbers 4764, 5454, 5096, and 5277) + TX; Bacillus subtilis MBI 600 strain (available from BASF SE as SUBTILEX), accession number NRRL B-50595, U.S. Patent No. 5,061,495 + TX; Bacillus subtilis GB03 strain (available from Bayer AG, Germany as Kodiak®) + TX; Bacillus subtilis BU1814 strain (BASF Bacillus subtilis CX-9060 +TX from Certis USA LLC, a subsidiary of Mitsui & Co.; Bacillus subtilis KTSB strain (FOLIACTIVE® from Donaghys) +TX; Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies, PORTENTO® from Idai Nature) +TX; Bacillus subtilis Y1336 strain (BIOBAC® WP from Taiwan BioNTech, registered in Taiwan as a biological fungicide under registration numbers 4764, 5454, 5096, and 5277) +TX; BASF Paenibacillus epiphyticus from SE (WO 2016 / 020371) + TX; Paenibacillus polymyxa ssp. plantarum from BASF SE (WO 2016 / 020371) + TX;strains belonging to the genus Paenibacillus and having accession numbers NRRL B-50972 or NRRL B-67129, International Publication No. WO 2016 / 154297) +TX; Pseudomonas chlororaphis, in particular the strain AFS009, accession number NRRL B-50897, International Publication No. WO 2017 / 019448 (available, for example, as HOWLER™ and ZIO™ from AgBiome Innovations, USA) +TX; Pseudomonas chlororaphis, in particular the strain MA342 (for example, as CEDOMON™, CERALL™ and CEDRESS™ from Bioagri and Koppert) +TX; Pseudomonas fluorescens Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena) +TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (deposit number DSM 7206), (MYCOSTOP® from Verdera, PREFENCE® from BioWorks, see Crop Protection 2006, 25, 468-475) +TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus) also known as strain WYCD108US (ACTINO-IRON® and ACTINOVATE® from Novozymes) +TX;

[0301] (2.2) Fungi, such as Ampelomyces quisqualis, in particular the strain AQ10 (e.g., AQ 10® from IntrachemBio Italia) + TX; Ampelomyces quisqualis strain AQ10, deposit number CNCM 1-807 (e.g., AQ 10® from IntrachemBio Italia) + TX; Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular spores of the strain DSM14940 + TX; Aureobasidium pullulans Aureobasidium pullulans, in particular spores of strain DSM 14941 + TX; Aureobasidium pullulans, in particular a mixture of spores of strains DSM 14940 and DSM 14941 (e.g., Botector® by China bio-ferm) + TX; Chaetomium cupreum (deposit number CABI 353812) (e.g., BIOKUPRUM® by AgriLife) + TX; Chaetomium globosum (available as RIVADIOM® by Rivale) + TX; Cladosporium cladosporioides, strain H39, deposit number CBS 122244, U.S. Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Coniothyrium minitans, in particular strain CON / M / 91-8 (deposit number DSM 9660, e.g. Contans® from Bayer CropScience Biologics GmbH) + TX; Cryptococcus flavescens, strain 3C (NRRL Y-50378) (B2.2.99) + TX; Dactylaria candida + TX; Dilophosphora alopecuri (available as TWIST FUNGUS®) + TX; Fusarium oxysporum, strain Fo47 (available as FUSACLEAN® by Natural Plant Protection) + TX; Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop® by Lallemand) + TX; Gliocladium roseum (synonym: Clonostachys rosea f. rosea f. rosea), in particular the 321U strain from Adjuvants Plus, the ACM941 strain disclosed by Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can. J. Plant Sci. 2003, 83(3):519-524), or (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726', Australasian Plant Pathol.2007, 36(2), 95-101) +TX; conidia of Lecanicillium lecanii (formerly Verticillium lecanii) strain KV01 (e.g., Vertalec® by Koppert / Arysta) +TX; Metschnikowia fructicola, in particular strain NRRL Y-30752 (B2.2.3) +TX; Microsphaeropsis ochracea +TX; Muscodor roseus, in particular strain A3-5 (deposit number NRRL 30548) +TX; Penicillium steckii from BASF SE (DSM 27859, WO 2015 / 067800) +TX; Penicillium vermiculatum +TX; Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from Danstar Ferment) +TX; Pichia anomala strain WRL-076 (NRRL Y-30842), U.S. Pat. No. 7,579,183 +TX; Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., Canada) +TX; Saccharomyces cerevisiae, particularly strain LASO2 (Agro-Levures et Derives), cell walls of strain LAS117 (CEREVISANE® from Lesaffre, ROMEO® from BASF SE), strain CNCM No. 1-3936, strain CNCM No. 1-3937, strain CNCM No. 1-3938, strain CNCM No.1-3939 strain (WO 2010 / 086790, from Lesaffre et Compagnie, France) +TX; Simplicillium lanosoniveum +TX; Talaromyces flavus strain V117b +TX; Trichoderma asperelloides strain JM41R (deposit number NRRL B-50759) (e.g., TRICHO PLUS® from BASF SE) +TX; Trichoderma asperellum, in particular the kd strain (e.g., T-Gro from Andermatt Biocontrol) +TX; Trichoderma asperellum, in particular the SKT-1 strain, deposit number FERM P-16510 (e.g. ECO-HOPE® from Kumiai Chemical Industry Co., Ltd.), strain T34 (e.g. T34 Biocontrol from Biocontrol Technologies SL, Spain) or strain ICC 012+TX from Isagro; Trichoderma atroviride, in particular strain SC1 (deposit number CBS 122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g. Agrimm Technologies Ltd.Sentinel from Agrimm Technologies) +TX; Trichoderma atroviride, strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, France) +TX; Trichoderma atroviride, strain V08 / 002387 +TX; Trichoderma atroviride, strain NMI V08 / 002388 +TX; Trichoderma atroviride, strain NMI V08 / 002389 +TX; Trichoderma atroviride, strain NMI V08 / 002390 +TX; Trichoderma atroviride, strain LC52 (e.g., Agrimm Technologies) +TX Tenet by Rakuten, Ltd.) +TX; Trichoderma atroviride, ATCC 20476 strain (IMI 206040) +TX; Trichoderma atroviride, T11 strain (IMI352941 / CECT20498) +TX; Trichoderma atroviride, SKT-1 strain (FERM P-16510), JP 11-253151 A +TX; Trichoderma atroviride, SKT-2 strain (FERM P-16511), JP 11-253151 A +TX; Trichoderma atroviride, SKT-3 strain (FERM P-17021), JP 11-253151 A + TX; Trichoderma fertile (e.g., TrichoPlus, a product from BASF) + TX; Trichoderma gamsii (formerly known as Trichoderma viride), strain ICC080 (IMI CC 392151 CABI, e.g., AGROBIOSOL DE MEXICO, SADE CVTrichoderma gamsii (formerly known as T. viride), strain ICC080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, SADE CV) +TX; Trichoderma harmatum +TX; Trichoderma harmatum, deposit number ATCC 28012 +TX; Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (from Simbiose Agro) +TX; Trichoderma harzianum harzianum) +TX; Trichoderma harzianum rifai strain T39 (e.g., Trichodex® from Makhteshim, USA) +TX; Trichoderma harzianum strain ITEM 908 (e.g., Trianum-P from Koppert) +TX; Trichoderma harzianum strain TH35 (e.g., Root-Pro by Mycontrol) +TX; Trichoderma harzianum strain DB 103 (e.g., TG by Dagutat Biolab. Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX; Trichoderma stromaticum, deposit number Ts3550 (e.g., Tricovab by CEPLAC, Brazil) + TX; Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard by Certis, USA) + TX; Trichoderma virens strain G-41, formerly known as Gliocladium virens (deposit number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, USA) +TX; Trichoderma viride, strain TV1 (e.g., Trianum-P by Koppert) +TX; Trichoderma viride, in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) +TX; Trichoderma asperellum strain ICC 012 (synonym: Trichoderma harzianum ICC012), accession number CABI CC IMI 392716, and Trichoderma gamsii gamsii (formerly known as Trichoderma viride (T. viride)) strain ICC 080, deposit number IMI 392151 (e.g., BIO-TAM™ from Isagro USA, Inc. or Agrobiosol de Mexico, SA de CV)Ulocladium oudemansii strain U3, deposit number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand, and BOTRYSTOP® by BioWorks, Inc.) +TX; Verticillium albo-atrum (formerly known as V. dahliae), strain WCS850, deposit number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) +TX; Verticillium chlamydosporium +TX.

[0302] (3) A biological control agent having the effect of improving plant growth and / or plant health, selected from the following group: (3.1) Bacteria, such as Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX; Azospirillum lipoferum (e.g., VERTEX-IF® from TerraMax, Inc.) + TX; Azorhizobium caulinodans, particularly the ZB-SK-5 strain + TX; Azotobacter chroococcum, particularly the H23 strain + TX; Azotobacter vinelandii, particularly the ATCC 12837 strain + TX; Azotobacter vinelandii and Clostridium pasteurianum a mixture with Bacillus pasteurianum (available as INVIGORATE® from Agrinos) + TX; Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX; Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542, WO 2017 / 205258) + TX; Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes) + TX; Bacillus amyloliquefaciens, especially strain IN937a + TX; Bacillus amyloliquefaciens amyloliquefaciens), in particular the strain FZB42 (e.g., RHIZOVITAL® from ABiTEP, Germany) +TX; Bacillus amyloliquefaciens BS27 (deposit number NRRL B-5015) +TX; Bacillus cereus family member EE128 (NRRL No.B-50917) + TX; Bacillus cereus family member EE349 (NRRL No. B-50928) + TX; Bacillus cereus, in particular strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, USA) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides BT155 (NRRL No. B-50921) + TX; Bacillus mycoides EE118 (NRRL No. B-50918) + TX; Bacillus mycoides strain EE141 (NRRL No. B-50916) + TX; Bacillus mycoides strain BT46-3 (NRRL No. B-50922) + TX; Bacillus pumilus, in particular strain QST2808 (accession number NRRL No. B-30087) + TX; Bacillus pumilus, in particular strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, Germany) + TX; Bacillus siamensis, in particular strain KCTC 13613T + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (accession number NRRL B-21661, described in U.S. Patent No. 6,060,051, available from Bayer CropScience LP, USA as SERENADE® OPTI or SERENADE® ASO) + TX; Bacillus subtilis, particularly strain AQ30002 (deposit number NRRL B-50421, described in U.S. Patent Application Publication No. 13 / 330,576) + TX; Bacillus subtilis, particularly strain AQ30004 (NRRL No.B-50455, as described in U.S. Patent Application Publication No. 13 / 330,576) + TX; Bacillus subtilis strain BU1814 (e.g., TEQUALIS® from BASF SE), Bacillus subtilis strain rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX; Bacillus thuringiensis strain BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7) + TX; a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (FMC available from Biotech Corporation as QUARTZO® (WG), PRESENCE® (WP) +TX; Bacillus subtilis, particularly strain MBI 600 (e.g., SUBTILEX® from BASF SE) +TX; Bacillus tequilensis, particularly strain NII-0943 +TX; Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes) +TX; Delftia acidovorans, particularly strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds) +TX; Mesorhizobium cicer (e.g., NODULATOR® from BASF SE) +TX; Lactobacillus sp.) (e.g. LACTOPLANT® from LactoPAFI) + TX; Rhizobium leguminosarium biovar viciae (e.g. NODULATOR® from BASF SE) + TX; Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX; Pseudomonas aeruginosa, in particular the strain PN1 + TX; Rhizobium leguminosarum, in particular the strain bv.viceae Z25 (deposit number CECT 4585) + TX; Paenibacillus polymyxa, in particular the strain AC-1 (e.g. Ltd.) +TX; Serratia marcescens, particularly strain SRM (deposit number MTCC 8708) +TX; Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) +TX; Thiobacillus sp. (e.g., CROPAID® from Cropaid Ltd, UK) +TX.

[0303] (3.2) Fungi, such as Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH) + TX; Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg), Talaromyces flavus strain V117b + TX; Trichoderma atroviride strain CNCM1-1237 (e.g., Esquive® WP from Agrauxine, France), Trichoderma viride viride), for example, strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161:125-137) + TX; Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Agrimm Technologies Ltd.Sentinel® from Andermatt Biocontrol) + TX; Trichoderma atroviride strain SC1 (described in WO 2009 / 116106) + TX; Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX; Trichoderma asperellum strain (Eco-T from Plant Health Products, South Africa) + TX; Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) + TX; Myrothecium verrucaria strain AARC-0255 (e.g., DiTera® from Valent Biosciences) + TX; Penicillium bilaii strain ATCC 20851 + TX; Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, Czech Republic) + TX; Trichoderma virens strain GL-21 (e.g., SoilGard® from Certis, USA) + TX; Verticillium albo-atrum (formerly known as V. dahliae) strain WCS850 (CBS 276).92, e.g. Dutch Trig from Tree Care Innovations) +TX; Trichoderma atroviride, in particular strains V08 / 002387, NMI V08 / 002388, NMI V08 / 002389, and NMI V08 / 002390 +TX; Trichoderma harzianum strain ITEM 908, Trichoderma harzianum strain TSTh20 +TX; Trichoderma harzianum strain 1295-22 +TX; Pythium oligandrum strain DV74 +TX; Rhizopogon amylopogon amylopogon (e.g., Myco-Sol from Agri-Enterprise, LLC (formerly Helena Chem. Company)) + TX; Rhizopogon fulvigleba (e.g., Myco-Sol from Agri-Enterprise, LLC (formerly Helena Chem. Company)) + TX; Trichoderma virens strain GI-3 + TX.

[0304] (4) A biological control agent having insecticidal activity selected from the following: Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.) +TX; Bacillus amyloliquefaciens, in particular strain PTS-4838 (e.g., AVEO from Valent Biosciences, USA) +TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., VOTIVO® from BASF SE) +TX; Bacillus mycoides, isolate J (e.g., BmJ from Certis USA LLC) +TX; Bacillus sphaericus, in particular strain 2362 (strain ABTS-1743) of serotype H5a5b (e.g., Valent Biosciences, USA) +TX. aizawai, in particular the strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX; Bacillus thuringiensis subsp. aizawai, in particular the serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, USA) + TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® from Becker Microbial Products IL) + TX; Bacillus thuringiensis subsp. israelensis subsp. israelensis (serotype H-14) strain AM65-52 (deposit number ATCC 1276) (e.g., VECTOBAC® by Valent BioSciences, USA) +TX; Bacillus thuringiensis subsp. aizawai (Bacillus thuringiensis subsp.aizawai strain GC-91 + TX; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory) + TX; Bacillus thuringiensis var. japonensis strain Buibui + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, Illinois (IL)) + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, Illinois (IL)) + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, Illinois (IL)) + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Bayer CropScience, e.g., BARITONE from Bayer CropScience) + TX; Bacillus Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., Valent BioSciences, USA) + TX; Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® from AEF Global) + TX; Bacillus thuringiensis subsp. kurstaki strain ABTS 351 + TX; Bacillus thuringiensis subsp. kurstaki strain PB 54 + TX; Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN® from Certis, USA) + TX; Bacillus thuringiensis subsp.kurstaki SA 12 strain (THURICIDE from Certis, USA) + TX; Bacillus thuringiensis subsp. kurstaki EG 2348 strain (LEPINOX® from Certis, USA) + TX; Bacillus thuringiensis subsp. kurstaki EG 7841 strain (CryMAX® from Certis, USA) + TX; Bacillus thuringiensis subsp. tenebrionis NB 176 strain (SD-5428, e.g., NOVODOR® FC from BioFa DE) + TX; Brevibacillus laterosporus (Ecolibrium Biologicals LATERAL® from Marrone Bio Innovations) +TX; Burkholderia spp., in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (deposit number NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; e.g., MBI206 TGAI and ZELTO® from Marrone Bio Innovations) +TX; Chromobacterium subtsugae, in particular strain PRAA4-1T (e.g., MBI-203; e.g., GRANDEVO® from Marrone Bio Innovations) +TX; Lecanicillium muscarium muscarium) Ve6 (MYCOTAL from Koppert) + TX; Paenibacillus popilliae (formerly Bacillus popilliae); e.g., St.MILKY SPORE POWDER™ or MILKY SPORE GRANULAR™ from Gabriel Laboratories + TX; Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX; Serratia entomophila (e.g., INVADE™ from Wrightson Seeds) + TX; Serratia marcescens, in particular strain SRM (deposit number MTCC 8708) + TX; Trichoderma asperellum (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis strain ZAP (e.g., ZAP MALES™ from MosquitoMate) + TX.

[0305] (4.2) Fungi, such as Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain GHA (deposit number ATCC 74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam Int. Corp.) + TX; Beauveria bassiana strain ATP02 (deposit number DSM 24665) + TX; Isaria fumosorosea (formerly Paecilomyces fumosoroseus, Apopka 97 strain, e.g., PREFERAL® from SePRO) + TX; Metarhizium anisopliae anisopliae 3213-1 (deposited under accession number NRRL 67074, disclosed in WO 2017 / 066094; Pioneer Hi-Bred International) +TX; Metarhizium robertsii 15013-1 (deposited under accession number NRRL 67073) +TX; Metarhizium robertsii 23013-3 (deposited under accession number NRRL 67075) +TX; Paecilomyces lilacinus strain 251 (MELOCON® from Certis, USA) +TX; and Zooftora radicans +TX.

[0306] (5) A virus selected from the group consisting of Adoxophyes orana (smaller apple tortrix) granulosis virus (GV) + TX; Cydia pomonella (codling moth) granulosis virus (GV) + TX; Helicoverpa armigera (helicobacterium armigera) nucleopolyhedrovirus (NPV) + TX; Spodoptera exigua (beet armyworm) mNPV + TX; Spodoptera frugiperda (stalk armyworm) mNPV + TX; or Spodoptera littoralis (Egyptian armyworm) NPV + TX.

[0307] (6) Bacteria and fungi that can be added as an "inoculant" to plants or plant parts or plant organs and that promote plant growth and plant health due to their specific properties, selected from the following: Agrobacterium spp. + TX; Azorhizobium caulinodans + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., in particular Burkholderia cepacia (formerly Pseudomonas cepacia + TX); Gigaspora spp. spp.) or Gigaspora monosporum + TX; Glomus spp. + TX; Laccaria spp. + TX; Lactobacillus buchneri + TX; Paraglomus spp. + TX; Pisolithus tinctorus + TX; Pseudomonas spp. + TX; Rhizobium spp., especially Rhizobium trifolii + TX; Rhizopogon spp. + TX; Scleroderma spp. spp.) + TX; Suillus spp. + TX; Streptomyces spp. + TX.

[0308] (7) Products containing plant extracts and proteins and secondary metabolites formed by microorganisms that can be used as biological control agents, selected from the following: garlic (Allium sativum) (NEMGUARD from Eco-Spray; BRALIC from ADAMA) + TX; Armour-Zen + TX; wormwood (Artemisia absinthium) + TX; azadirachtin (for example, AZATIN XL from Certis, USA) + TX; Biokeeper WP + TX; Brassicaceae extract, in particular rapeseed powder or mustard powder + TX; Cassia nigricans + TX; Celastrus angulatus + TX; Chenopodium anthelminticum + TX; chitin + TX; Dryopteris filix-mas) + TX; Horsetail (Equisetum arvense) + TX; Fortune Aza + TX; Fungastop + TX; Quinoa (Chenopodium quinoa) saponin extract from quinoa seeds (e.g., Heads Up® (quinoa saponins) from California (CA) Heads Up plant Protectants) + TX; Natural Blad polypeptide extracted from lupine seeds (PROBLAD® from Certis EU) + TX; Natural Blad polypeptide extracted from lupine seeds (FRACTURE® from FMC) + TX; Pyrethrum / pyrethrin + TX; Surinam oak (Quassia amara) + TX; Oak (Quercus) + TX; Quillaja extract (QL AGRI 35 from BASF) + TX; Giant knotweed (Reynoutria sachalinensis) extract (Marrone REGALLIA® from Bio, REGALIA® MAXX) + TX; "Requiem™ Insecticide" + TX; rotenone + TX; ryania / ryanodine + TX; Symphytum officinale + TX;Tansy (Tanacetum vulgare) + TX; Thymol + TX; Thymol and Geraniol Mixture (CEDROZ from Eden Research) + TX; Thymol, Geraniol and Eugenol Mixture (MEVALONE® from Eden Research) + TX; Triact 70 + TX; TriCon + TX; Nasturtium (Tropaeulum majus) + TX; Tea Tree (Melaleuca alternifolia) Extract (TIMOREX GOLD® from STK) + TX; Stinging Nettle (Urtica dioica) + TX; Veratrin + TX; Mistletoe (Viscum album) + TX;

[0309] 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.

[0310] The reference numbers in square brackets following the active ingredient, e.g., [3878-19-1], represent Chemical Abstracts Registry Numbers. The above-mentioned mixing partners are publicly known. When active ingredients are listed in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are listed therein by the parenthetical identifiers shown above for specific compounds herein; for example, the compound "abamectin" is listed as identifier (1). When a specific compound shown above in this specification is annotated with "[CCN]," the compound in question is listed in the "Compendium of Pesticide Common Names," available on the Internet at [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.

[0311] Most of the active ingredients described herein above are referred to by so-called "common names," and where appropriate, the appropriate "ISO common name" or other "common name" is used. Where the designation is not a "common name," the type of designation used instead for that particular compound is stated in parentheses, which may be an IUPAC name, IUPAC / Chemical Abstracts name, "chemical name," "common name," "compound name," or "development code," or, if neither these nor a "common name" is used, an "synonym" is used. "CAS Registry Number" refers to the Chemical Abstracts Registry Number.

[0312] The trade name in square brackets after the active ingredient represents one or more commercially available products containing this active ingredient.

[0313] The mixture of a compound of formula (I) selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 listed in Table P (described later), with the above-mentioned active ingredient is preferably a mixture ratio of a compound selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or one compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 listed in Table P (described later), with the above-mentioned active ingredient, preferably 100:1 to 1:6000, particularly 50:1 to 1:50, more particularly 20:1 to 1:20, still more particularly 10:1 to 1:10, very particularly 5:1 to 1:5, with a ratio of 2:1 to 1:2 being particularly preferred, as well as a ratio of 4:1 to 2:1, which ratio may in particular be 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.

[0314] The mixture may be used in a method for controlling pests, which method comprises applying a composition comprising the mixture to the pest or its environment, but excludes methods of treating the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0315] Mixtures containing a compound of formula (I) selected from the compounds of formula (I), (IA), (I-A1) or (I-A2), or a compound selected from the group consisting of the compounds shown in Tables A1 to A4, or a compound selected from P-1 to P-9 listed in Table P (described below), and one or more of the active ingredients described above can be applied, for example, in the form of a single "ready-to-use" mixture, in a spray mixture consisting of a mixture of separate formulations of a single active ingredient, such as a "tank mix," or in a combination in which the single active ingredients are applied sequentially, i.e., one after the other, over a reasonably 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 essential to the practice of the invention.

[0316] The compositions according to the invention may also comprise further solid or liquid adjuvants, 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 modifiers, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0317] The compositions according to the invention can be prepared in a manner known per se, for example by grinding, sieving and / or compressing the solid active ingredient in the absence of an auxiliary agent, and by intimately mixing and / or grinding the active ingredient together with the auxiliary agent in the presence of at least one auxiliary agent.These processes for preparing the compositions and the use of compound I for preparing these compositions are also the subject of the present invention.

[0318] The application method of the present composition for controlling the above-mentioned types of pests, such as spraying, misting, dusting, brushing, dusting, granulation, or pouring, is selected to suit the intended purpose in the actual situation, and the use of the composition for controlling the above-mentioned types of pests is another subject of the present invention. Typical active ingredient concentrations are 0.1 to 1000 ppm, preferably 0.1 to 500 ppm. The application rate per hectare is generally 1 to 2000 g of active ingredient per hectare, particularly 10 to 1000 g / ha, preferably 10 to 600 g / ha.

[0319] In the field of crop protection, the preferred application method is application to the leaves of plants (foliar application), and the application frequency and application rate can be selected according to the risk of occurrence of the target pest. Alternatively, the active ingredient can reach the plant via the roots (systemic action), by irrigating the plant habitat with a liquid composition, or by incorporating 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 rice cultivation, such granules can be metered into flooded rice fields.

[0320] The compounds of formula (I) and compositions thereof of the present invention 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 (coated) to the seed kernels by immersing the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to apply the composition when planting the propagation material at the application site, for example, when sowing seeds in a seed furrow. These methods for treating plant propagation material and the plant propagation material thus treated are also further subjects of the present invention. Typical treatment rates will vary depending on the plant and the pests / fungi to be controlled, but are generally 1 to 200 grams per 100 kg of seeds, preferably 5 to 150 grams per 100 kg of seeds, for example 10 to 100 grams per 100 kg of seeds.

[0321] The term "seed" includes seeds and all types of plant propagation material, including but not limited to true seeds, seed fragments, suckers, corn, bulbs, fruits, tubers, grains, rhizomes, cuttings, and the like, but in a preferred embodiment refers to true seeds.

[0322] The present invention also includes seeds coated or treated with or containing a compound of formula (I). The terms "coated or treated and / or containing" generally mean that the majority of the active ingredient is on the surface of the seed at the time of application, although depending on the application method, more or less of the active ingredient may penetrate into the seed material. When the seed product is (re)planted, the active ingredient may be absorbed by the seed product. In one embodiment, the present invention provides a plant propagation material having a compound of formula (I) attached thereto. Further, it provides a composition comprising plant propagation material treated with a compound of formula (I).

[0323] Seed treatment includes any suitable seed treatment technique known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. Application of the compound of formula (I) by seed treatment can be carried out by any known method, such as spraying, or by dusting the seeds before sowing or at the time of sowing / planting the seeds.

[0324] The compounds of the present invention may be distinguished from other similar compounds by showing higher efficacy at lower application rates and / or controlling different pests, which can be determined by the skilled artisan using experimental techniques to show that the compounds of the present invention are more effective at lower concentrations, e.g. 10 ppm, 5 ppm, 2 ppm, 1 ppm or 0.2 ppm or at lower application rates as needed, e.g. 1 ml of AI (active ingredient). 2 Higher efficacy may be evidenced by using 300, 200 or 100 mg per unit area. Higher efficacy may be evidenced by an improved safety profile (improved physicochemical properties against above- and below-ground non-target organisms (fish, birds, bees, etc.) or improved biodegradability).

[0325] In each aspect and embodiment of the present invention, "consisting essentially of" and variations thereof are preferred embodiments of "comprising" and variations thereof, and "consisting of" and variations thereof are preferred embodiments of "consisting essentially of" and variations thereof.

[0326] The present disclosure in this application provides all combinations of each embodiment disclosed herein.

[0327] It should be noted that the disclosure herein regarding compounds of formula (I) applies equally to compounds of formula (I), (Ia), (Ib), (I-A1), (I-A2), or a compound selected from the group consisting of compounds shown in Tables A1-A2, or compounds set forth in Table P (described below).

[0328] The compound according to the present invention can be used as a pesticide in its original form, but is generally formulated into a composition in various ways using formulation adjuvants such as carriers, solvents, and surfactants.The formulation can be in various physical forms, such as dust, gel, wettable powder, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, finely emulsifiable concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or water-miscible organic solvents as carriers), 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 as they are or diluted before use.Dilution can be carried out, for example, with water, liquid fertilizer, micronutrients, organisms, oil, or solvents.

[0329] The formulations can be prepared by mixing the active ingredient with formulation auxiliaries to obtain a composition in the form of, for example, a finely divided solid, granules, a solution, a dispersion, or an emulsion. The active ingredient can also be formulated with other auxiliaries such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surfactants, or combinations thereof.

[0330] Active ingredients can also be contained within very fine microcapsules. Microcapsules contain active ingredients in a porous carrier. This allows for controlled (e.g., sustained) release of the active ingredient into the environment. Microcapsules typically have a diameter of 0.1 to 500 microns. They contain approximately 25 to 95% of the active ingredient by weight of the capsule. The active ingredient can be in the form of a monolithic solid, a particulate 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, very fine microcapsules can be formed in which the active ingredient is contained in the form of fine particles in a solid matrix of a substrate material, but the microcapsules themselves are not encapsulated.

[0331] Suitable formulation adjuvants for preparing the compositions according to the invention are known per se. Usable 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, 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 higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0332] Suitable solid carriers are, for example, talc, titanium dioxide, pyroferritic clays, silica, attapulgite clays, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin and similar substances.

[0333] 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 can also be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surface-active materials include, for example, salts of lauryl sulfate, 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 materials, such as those described in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey (1981).

[0334] Other adjuvants that may be used in pesticide formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, penetration aids, micronutrients, plasticizers, flow regulators, lubricants, dispersants, thickeners, antifreeze agents, fungicides, and liquid and solid fertilizers.

[0335] The composition according to the present invention may contain an additive comprising an oil of vegetable or animal origin, a mineral oil, an alkyl ester of such an oil, or a mixture of such oils and oil derivatives. The amount of additive oil in the composition according to the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the additive oil can be added to a spray tank at the desired concentration after preparing the spray mixture. Preferred additive oils include mineral oil or vegetable oils, such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oil, alkyl esters of vegetable oils, such as methyl derivatives, or animal oils, such as fish oil or beef tallow. Preferred additive oils are C8 to C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids, such as 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.

[0336] The compositions of the present invention generally contain 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound of the present invention and 1 to 99.9% by weight of formulation aids, preferably including 0 to 25% by weight of a surfactant. Commercially available products will preferably be formulated as concentrates, but end users will usually use diluted formulations.

[0337] 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 climatic conditions and other factors determined by the method, time of application and the target crop. As a general guideline, the compounds can be applied at rates of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0338] A preferred formulation may have the following composition (% by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35% Powder: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99% Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30% Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90% Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85% [Example]

[0339] The following examples further illustrate the present invention but do not limit it.

[0340] The compounds of the present invention can be distinguished from known compounds by exhibiting higher efficacy at lower application rates, which can be confirmed by one skilled in the art using the experimental procedures outlined in the Examples, using lower application rates as needed, for example 60 ppm, 20 ppm or 2 ppm.

[0341] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer. Chemical shifts are expressed as TMS ( 1 H) or CFCl3( 19F) are expressed in ppm relative to a standard. Spectra were measured in deuterated solvents as specified. Compounds were characterized using one of the LCMS methods listed below. The characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - is.

[0342] Throughout this specification, temperatures are given in degrees Celsius (°C) and "mp" means melting point. LC / MS means liquid chromatography mass spectrometry. A description of the instrument and method follows.

[0343] LC-MS Method A: Spectra were recorded using an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporations equipped with an electrospray source (polarity: positive or negative ion, capillary voltage: 3.0 kV, cone voltage: 30 V, extractor voltage: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass scan range: 140-800 Da) and an ACQUITY UPLC from Waters Corporations 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 (2.5 min); flow rate (ml / min) 0.75.

[0344] LC-MS Method B: Spectra were recorded using a mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) from Waters equipped with an electrospray source (polarity: reversible polarity, capillary voltage: 0.8-3.00 kV, cone range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass scan range: 110-850 Da) and an Acquity UPLC from Waters equipped with a quaternary solvent manager, heated column compartment, diode array detector, column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm, temperature: 40 °C, DAD wavelength range (nm): 200-400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 10%B (0min); 10-50%B (0-0.2min); 50-100%B (0.2-0.6min); 100%B (0.6-1.3min); 100-10%B (1.3-1.4min); 10%B (1.4-1.6min); Flow rate (mL / min) 0.6.

[0345] LC-MS C method: Spectra were recorded using a mass spectrometer (6410 Triple Quadrupole Mass Spectrometer) from Agilent Technologies equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary voltage: 4.00 kV, fragmentor voltage: 100 V, desolvation temperature: 350 °C, gas flow rate: 11 L / min, nebulizer gas: 45 psi, mass scan range: 110-1000 Da) and a 1200 Series HPLC from Agilent: quaternary pump, heated column compartment and VWD detector, column: KINETEX EVO C18, 2.6 μm, 50 × 4.6 mm, temperature: 40 °C, VWD detector wavelength: 254 nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile 0.1% HCOOH: Gradient: 10%B, 90%A (0min); 100%B (0.9-1.8min); 100-10%B (1.8-2.2min); 10%B (2.2-2.5min); Flow rate (mL / min) 1.8.

[0346] LC-MS D method: Spectra were recorded using a mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) from Waters equipped with an electrospray source (polarity: reversible polarity, capillary voltage: 0.8-3.00 kV, cone voltage range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 1000 L / h, mass scan range: 110-850 Da) and an Acquity UPLC from Waters equipped with a quaternary solvent manager, heated column compartment, diode array detector, column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm, temperature: 40 °C, DAD wavelength range (nm): 200-400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 10%B (0min); 10%B (0.0-0.5min); 100%B (0.5-2min); 100%B (2-3min); 10%B (3-3.5min); 10%B (3.5-4min); Flow rate (mL / min) 0.6.

[0347] LC-MS E method: Spectra were recorded using: a mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive and negative ions): capillary voltage: 0.8-3.00 kV, cone voltage: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass scan range: 110-950 Da and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD, column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210-400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min) 0.85, gradient: 10% B isocratic (0.2 min), then 10–100% B (1.0 min), 100% B isocratic (0.2 min), 100–10% B (0.05 min), 10% B isocratic (0.05 min).

[0348] Formulation Examples

[0349] [Table 8]

[0350] This combination is thoroughly mixed with an adjuvant and the mixture is thoroughly ground in a suitable grinder to give a wettable powder (powder) which can be diluted with water to form a suspension of the desired concentration.

[0351] [Table 9]

[0352] This combination is thoroughly mixed with an adjuvant, and the mixture is thoroughly ground in a suitable grinder to give a dust that can be used directly for seed treatment.

[0353] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (ethylene oxide 4-5 moles) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 moles) 4% Cyclohexanone 30% Xylene mixture 50%

[0354] This concentrate can be diluted with water to obtain an emulsion of the required dilution that can be used for plant protection.

[0355] [Table 10]

[0356] This combination is mixed with a carrier and the mixture is ground in a suitable grinder to give a ready-to-use dust, which can also be used as a dry seed dressing.

[0357] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0358] This combination is mixed with the adjuvants and ground, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0359] Coated granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0360] This combination is finely ground and applied uniformly in a mixer to kaolin moistened with polyethylene glycol, thereby obtaining non-dusting coated granules.

[0361] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (ethylene oxide 15 moles) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (75% emulsion in water) 1% water 32%

[0362] This combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect against microbial infestation.

[0363] Flowable seed treatment Active ingredient 40% Propylene glycol 5% Butanol PO / EO copolymer 2% Tristyrenephenol with 10-20 moles of EO 2% 1,2-Benzisothiazolin-3-one (20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (75% emulsion in water) 0.2% Water 45.3%

[0364] This combination is pulverized and intimately mixed with adjuvants to obtain a flowable formulation, which can be diluted with water to obtain a solution of the desired dilution, ready for use as a seed treatment. By carrying out such dilutions, growing plants as well as plant propagation materials can be treated by spraying, pouring, or dipping to protect against microbial infestation.

[0365] Sustained-release capsule suspension 28 parts of this combination are mixed with 2 parts aromatic solvent and 7 parts of an 8:1 toluene diisocyanate / polymethylene-polyphenylisocyanate mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is reached. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to the emulsion. The mixture is stirred until polymerization is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. This capsule suspension formulation contains 28% active ingredient. The median capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for that purpose.

[0366] Formulation types include emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil-flowable formulations (OF), oil-liquid formulations (OL), soluble concentrates (SL), ULV-suspensions (SU), ULV-liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), water-soluble granules (SG), or any that are technically feasible.

[0367] Shorthand: CDCl3 deuterated chloroform DCM dichloromethane (or methylene dichloride) DMF Dimethylformamide DMSO dimethyl sulfoxide DMSO-d6 Deuterated dimethyl sulfoxide EtOAc ethyl acetate HCl Hydrochloric acid h time LCMS Liquid Chromatography Mass Spectrometry rh relative humidity rt room temperature Rt retention time TBME Methyl tert-butyl ether or tert-butyl methyl ether THF tetrahydrofuran TLC thin layer chromatography

[0368] Preparation Examples: "Mp" means melting point in °C. The free radical represents a methyl group.

[0369] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer. Chemical shifts are expressed in terms of TMS ( 1 H) or CFCl3( 19 F) expressed in ppm relative to standard. Spectra were measured in deuterated solvents as specified.

[0370] Compounds were characterized using one of the following LCMS methods: The characteristic LCMS values ​​obtained for each compound were the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + Or (MH).

[0371] Example P1: Preparation of N-(1-cyanocyclopropyl)-7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxamide (compound P-7, Table P) [ka] Step A: Preparation of ethyl 6-bromo-7-methyl-indan-4-carboxylate [ka] Bromine (1.51 ml, 29.37 mmol, 1.2 equiv.) and silver nitrate (4.16 g, 24.47 mmol, 1 equiv.) in water (5 ml) were added dropwise to a mixture of ethyl 7-methylindan-4-carboxylate (5 g, 24.47 mmol) in acetic acid (25 ml) and nitric acid (1.1 ml) at room temperature. The resulting mixture was stirred overnight at room temperature. The reaction mixture was quenched with saturated sodium thiosulfate solution and extracted with EtOAc. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography to give the title compound, ethyl 6-bromo-7-methylindan-4-carboxylate. 1 H NMR(400MHz,CDCl3)δ ppm 1.41(t,J=7.15Hz,3H)2.11(quin,J=7.64Hz,2H)2.39(s,3H)2.92(t,J=7.58Hz,2H)3.27(t,J=7.64Hz,2H)4.36(q,J=7.09Hz,2H)8.03(s,1H)

[0372] Step B: Preparation of ethyl 7-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-4-carboxylate [ka] To a solution of ethyl 6-bromo-7-methyl-indan-4-carboxylate (7.58 g, 26.8 mmol) in 1,4-dioxane (265 mL) at room temperature, bis(pinacolato)diborane (13.7 g, 53.5 mmol, 2 equiv.) and potassium acetate (9.19 g, 93.7 mmol, 3.5 equiv.) were added. The reaction mixture was purged with argon for 15 minutes, and then 1,1'-bis(diphenylphosphine)ferrocene-palladium(II) dichloride dichloromethane complex (2.21 g, 2.68 mmol, 0.1 equiv.) was added. The reaction mixture was purged with argon for 10 minutes and heated at 100 °C for 20 hours. The reaction was monitored by TLC and LCMS. Complete conversion was observed. The reaction mixture was diluted with EtOAc, filtered through Celite, and concentrated under reduced pressure. The crude product was used in the next step without further purification.

[0373] Step C: Preparation of ethyl 6-hydroxy-7-methyl-indan-4-carboxylate [ka] Ethyl 7-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indan-4-carboxylate (8.84 g, 26.8 mmol) was dissolved in ethanol (134 mL). Hydrogen peroxide (9.11 mL, 80.3 mmol, 3 equiv.) was then added at 0°C. The reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC and LCMS. LCMS of the crude product indicated complete consumption of the starting material. The reaction mixture was quenched with saturated sodium metabisulfite solution and concentrated in vacuo. The residue was dissolved in EtOAc and diluted with water. The layers were separated, and the aqueous layer was extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was subjected to silica gel column chromatography. Pure fractions were collected and concentrated under reduced pressure to give ethyl 6-hydroxy-7-methyl-indan-4-carboxylate as a white solid. 1H NMR(400MHz,DMSO-d6)δ ppm(s,3H)1.29(t,J=7.07Hz,3H)1.97(t,J=7.50Hz,2H)2.07(s,3H)2.76(t,J=7 .50Hz,2H)3.08(t,J=7.57Hz,2H)4.23(q,J=7.13Hz,2H)7.23(s,1H)9.36(s,1H)

[0374] Step D: Preparation of ethyl 6-[(2S)-2-(tert-butoxycarbonylamino)propoxy]-7-methyl-indan-4-carboxylate [ka] To a solution of ethyl 6-hydroxy-7-methyl-indan-4-carboxylate (2.9 g, 13 mmol) and [(2S)-2-(tert-butoxycarbonylamino)propyl]methanesulfonic acid (5.0 g, 20 mmol, 1.5 equiv.) in DMF (150 mL) was added cesium carbonate (13 g, 39 mmol, 3 equiv.) at room temperature. The resulting suspension was heated at 100 °C for 12 h. The reaction was monitored by TLC and LCMS, both of which indicated complete consumption of the starting material. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc. The organic layer was concentrated under reduced pressure and dried in vacuo. The crude residue was purified by chromatography on silica gel using cyclohexane:EtOAc (0:60) as the eluent to give ethyl 6-[(2S)-2-(tert-butoxycarbonylamino)propoxy]-7-methyl-indan-4-carboxylate as a white solid. LC-MS (Method B): Retention time 1.26min, m / z277.2[M+H-tBu]

[0375] Step E: Preparation of [(1S)-2-(7-ethoxycarbonyl-4-methyl-indan-5-yl)oxy-1-methyl-ethyl]ammonium chloride [ka] To a solution of ethyl 6-[(2S)-2-(tert-butoxycarbonylamino)propoxy]-7-methyl-indan-4-carboxylate (4 g, 10.60 mmol) in 16.4 mL of EtOAc was added dropwise HCl (4 mol / L in EtOAc, 44 ml) at 0° C. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, washed with n-pentane, and dried under vacuum to give [(1S)-2-(7-ethoxycarbonyl-4-methyl-indan-5-yl)oxy-1-methyl-ethyl]ammonium chloride as a white solid. 1 H NMR(400MHz,DMSO-d6)δ ppm 1.28-1.33(m,3H)1.33-1.36(m,3H)1.94-2.06(m,2H)2.15-2.22(m,3H)2.81(br t,J=7.52Hz,2H)3.13(t,J=7.52Hz,2H)3.78-3.95(m,1H)3.97-4.15(m,2H)4.27(q,J=7.09Hz,2H)7.22(s,1H)8.44(br s,4H)

[0376] Step F: Preparation of ethyl 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylate [ka] A solution of [(1S)-2-(7-ethoxycarbonyl-4-methyl-indan-5-yl)oxy-1-methyl-ethyl]ammonium chloride (3.2 g, 10 mmol) in DCM (32 mL) was cooled to 0 °C, and triethylamine (8.6 mL, 61 mmol, 6 equiv.) was added, followed by trifluoromethanesulfonic anhydride (2.2 mL, 11 mmol, 1.05 equiv.) at 0 °C. This was then stirred overnight at room temperature. The reaction was monitored by TLC and LCMS. Once the starting material was consumed, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product. This crude product was purified by combi flash, eluting with 5–65% EtOAc in cyclohexane. 1 H NMR (400 MHz, CDCl 3 )δ ppm 1.32(t,J=7.15Hz,3H)1.41(d,J=6.72Hz,3H)2.01(t,J=7.58Hz,2H)2.08-2 .14(m,3H)2.77(t,J=7.52Hz,2H)3.16(t,J=7.64Hz,2H)3.89(s,1H)4.02(br d,J=6.72Hz,2H)4.28(q,J=7.13Hz,2H)5.4(s,1H)7.19(s,1H)

[0377] Step G: Preparation of 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylic acid [ka] A 100 mL two-neck flask was charged with ethyl 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylate (1.26 g, 3.08 mmol), THF (12.6 mL), and methanol (3.78 mL). Lithium hydroxide (0.226 g, 9.23 mmol, 3 equiv.) in water (6 mL) was added, and the resulting reaction mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC and LCMS. The reaction mixture was allowed to warm to room temperature, diluted with approximately 2 mL of 2N HCl until the pH reached approximately 3, and then extracted with EtOAc (2 × 25 mL). The combined organic layers were washed with saturated brine (20 mL), dried over sodium sulfate, and concentrated under reduced pressure to give crude 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylic acid. This compound was purified using preparative HPLC. 1H NMR(400MHz,DMSO-d6)δ ppm 1.20-1.35(m,2H)2.00(t,J=7.52Hz,2H)2.16(s,3H)2.81(t,J=7.46Hz,2H)3 .14(t,J=7.52Hz,2H)3.83-3.93(m,2H)3.94-4.04(m,1H)7.22(s,1H)9.60(br s,1H)12.70(br s,1H). 19 F NMR(377MHz,DMSO-d6)δ ppm -78.08(s,1F).

[0378] Step H: Preparation of N-(1-cyanocyclopropyl)-7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxamide (Compound P-7, Table P) 1-Aminocyclopropanecarbonitrile (0.0166 g, 0.2019 mmol, 1.1 equiv.), N,N-diethylethanamine (0.128 mL, 0.9177 mmol, 5 equiv.), and 1-propanephosphonic anhydride (50% by weight in EtOAc, 0.328 mL, 0.5506 mmol, 3 equiv.) were added to a solution of 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylic acid (70 mg, 0.1835 mmol) in EtOAc (0.918 mL). The reaction mixture was stirred at 25 °C for 2 hours. The reaction mixture was analyzed by LCMS and TLC. The reaction mixture was then diluted with water, extracted with EtOAc, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude residue obtained was purified by chromatography on silica gel using cyclohexane:EtOAc (0:100) as the eluent to give N-(1-cyanocyclopropyl)-7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indane-4-carboxamide as a sticky mass. 1H NMR (400 MHz, acetonitrile-d3) δ ppm 1.29-1.33 (m, 2H), 1.37-1.40 (m, 3H), 1.51-1.55 (m, 2H), 2.04 (quin, J = 7.50 Hz, 1H), 2.18 (s, 3H), 2.79-2.87 (m, 2H), 3.01-3.10 (m, 2H), 3.90-3.97 (m, 1H), 4.02 (br s, 1H), 6.85-6.87 (m, 1H), 6.86 (s, 1H), 7.26-7.28 (m, 1H), 7.32-7.40 (m, 1H). 19 F NMR (377 MHz, acetonitrile-d3) δ ppm -79.20 (s, 1F)

[0379] Example P2: Preparation of 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxamide (Compound P-1, Table P) [ka] Ammonium acetate (2.62 mmol, 5 equiv.), (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (commercially available as COMU®, 1.5 equiv., 0.7866 mmol), and N,N-diisopropylethylamine (4 equiv., 2.1 mmol) were added sequentially to a suspension of 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylic acid (200 mg, 0.5244 mmol, 1.0 equiv.) with stirring at 0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was then diluted with water, acidified with citric acid solution, and extracted with EtOAc. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by chromatography on silica gel using a mixture of cyclohexane and EtOAc as the eluent system to give 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indane-4-carboxamide as a white solid. 1H NMR(400MHz,CDCl3)δ ppm 1.41-1.46(m,3H)2.06-2.12(m,2H)2.17(s,3H)2.79-2.89(m,2H)2.95-3.13( m,2H)3.95-4.02(m,2H)4.04-4.13(m,1H)6.00(s,1H)6.20(s,1H)7.08(s,1H) 19 F NMR(377MHz,CDCl3)δ ppm -78.02(s)

[0380] Example P3: Preparation of N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxamide (compound P-2, Table P) [ka] [(4R)-2-Ethyl-3-oxo-isoxazolin-4-yl]ammonium chloride (1.1 equiv., 0.20 mmol), triethylamine (5 equiv., 0.92 mmol), and a solution of 1-propanephosphonic anhydride in EtOAc (3 equiv., 0.5506 mmol, 1.7 M) were added to a stirred solution of 7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indan-4-carboxylic acid (70 mg, 0.18 mmol) in EtOAc (5 mL / mmol). The reaction mixture was stirred at 25 °C for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc. The combined organic layers were washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by chromatography on silica gel using a mixture of cyclohexane and EtOAc as the eluent system to give N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-7-methyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]indane-4-carboxamide as a sticky solid. 1H NMR(400MHz,CDCl3)δ ppm 1.21-1.36(m,6H)1.96-2.11(m,2H)2.12(s,3H)2.74-2.87(m,2H)3.06-3.19(m,1H)3.19-3.30(m,1H)3.51-3.77(m ,2H)3.68-3.79(m,1H)3.97-4.01(m,3H)4.81(t,J=8.50Hz,1H)5.38(dt,J=11.63,8.32Hz,1H)7.27(s,1H)7.97(br s,1H) 19 F NMR(377MHz,CDCl3)δ ppm -78.13(s,1F)

[0381] Example P4: Preparation of N-(1-cyanocyclopropyl)-7-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]tetralin-5-carboxamide (Compound P-8, Table P) [ka] Step A: Preparation of methyl tetralin-5-carboxylate [ka] Thionyl chloride (2.0 equiv., 113.5 mmol) was added dropwise to a solution of tetralin-5-carboxylic acid (10 g, 56.750 mmol, 1.0 equiv.) in methanol (20 mL / g) at 0° C. The reaction mixture was then stirred at 70° C. for 6 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure, and the residue was dissolved in EtOAc and washed with saturated aqueous sodium bicarbonate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give methyl tetralin-5-carboxylate as an oil, which was used in the next step without further purification.

[0382] Step B: Preparation of methyl 7-bromotetralin-5-carboxylate [ka] Nitric acid (39.42 mmol, 1.5 equiv.) and bromine (39.42 mmol, 1.5 equiv.) were added dropwise, successively, to a solution of methyl tetralin-5-carboxylate (5 g, 26.28 mmol, 1.0 equiv.) in acetic acid (50 mL) and a solution of silver nitrate (39.42 mmol, 1.5 equiv.) in water (25 mL). The resulting reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was then cooled to 0°C, and saturated sodium thiosulfate solution was added dropwise. The solution was extracted with EtOAc, and the combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a mixture of cyclohexane and EtOAc as the eluent system to give 7-bromotetralin-5-carboxylate. 1 H NMR (400MHz, CDCl3) δ ppm 1.69-1.85(m,5H)2.74-2.84(m,2H)2.99(br t,J=5.75Hz,2H),3.87(s,3H)7.32-7.39(m,1H)7.78(d,J=2.13Hz,1H).

[0383] Step C: Preparation of methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetralin-5-carboxylate [ka] 4,4,5,5-Tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (2.0 equiv., 14.86 mmol) and potassium acetate (3.5 equiv., 26.01 mmol) were added to a solution of methyl 7-bromotetralin-5-carboxylate (2 g, 7.43 mmol, 1.0 equiv.) in 2-methyltetrahydrofuran (50 mL) at room temperature. The mixture was then purged with argon for 15 minutes, after which 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.1 equiv., 0.74 mmol) was added. The resulting reaction mixture was purged with argon for an additional 10 minutes and then heated at 60°C for 20 hours. The reaction mixture was then cooled to room temperature, diluted with EtOAc, filtered through Celite, and concentrated under reduced pressure. The resulting product was used in the next step without further purification.

[0384] Step D: Preparation of methyl 7-hydroxytetralin-5-carboxylate [ka] Methyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetralin-5-carboxylate (2.3 g, 7.3 mmol, 1.0 equiv.) was dissolved in ethanol (5 mL / mmol). Hydrogen peroxide (15 mmol, 2 equiv., 30% by weight) was then added at 0°C, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then quenched with saturated aqueous sodium metabisulfite, and the reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in EtOAc and water. The organic phase was separated, and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using a mixture of cyclohexane and EtOAc as the eluent to give methyl 7-hydroxytetralin-5-carboxylate as a white solid. 1H NMR(400MHz,CDCl3)δ ppm 1.86(dt,J=6.63,3.19Hz,5H)2.82-2.91(m,2H)3.01-3.11(m,2H)3.97(s,3H)5.04(br s,1H)6.83(d,J=2.75Hz,1H)7.37(s,1H)

[0385] Step E: Preparation of methyl 7-[(2S)-2-(tert-butoxycarbonylamino)propoxy]tetralin-5-carboxylate [ka] Potassium carbonate (11.64 mmol, 3.0 equiv.) was added to a stirred solution of methyl 7-hydroxytetralin-5-carboxylate (0.8 g, 3.88 mmol, 1.0 equiv.) and [(2S)-2-(tert-butoxycarbonylamino)propyl]methanesulfonate (7.76 mmol, 2.0 equiv.) in DMF (50 mL), and the resulting suspension was stirred at 120°C for 16 hours. Cesium carbonate (1.5 equiv.) was then added, and the reaction mixture was heated at 120°C for 16 hours. The reaction mixture was then diluted with water and extracted with EtOAc. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was then purified by column chromatography on silica gel using a mixture of cyclohexane and EtOAc to give methyl 7-[(2S)-2-(tert-butoxycarbonylamino)propoxy]tetralin-5-carboxylate. 1 H NMR(400MHz,CDCl3)δ ppm 1.24-1.34(m,5H)1.44-1.49(m,9H)1.78(dt,J=6.48,3.12Hz,4H)2.80(br s,2H)2.95-3.02(m,2H)3.87-3.95(m,5H)6.80(d,J=2.69Hz,1H)7.23(d,J=2.81Hz,1H)

[0386] Step F: Preparation of [(1S)-2-(8-methoxycarbonyltetralin-6-yl)oxy-1-methyl-ethyl]ammonium chloride [ka] To a solution of methyl 7-[(2S)-2-(tert-butoxycarbonylamino)propoxy]tetralin-5-carboxylate (700 mg, 1.93 mmol, 1.0 equiv.) in EtOAc (7 mL) was added dropwise a 4 M solution of HCl in EtOAc (14 mmol, 7.27 equiv.) at room temperature with stirring, and the reaction mixture was stirred overnight. The reaction mixture was then concentrated under reduced pressure to give [(1S)-2-(8-methoxycarbonyltetralin-6-yl)oxy-1-methyl-ethyl]ammonium chloride as a white solid. 1 H NMR(400MHz,DMSO-d6)δ ppm 1.21-1.35(m,3H)1.70(br t,J=2.94Hz,4H)2.77(br s,2H)2.85(br s,2H)3.35(s,1H)3.51-3.63(m...

Claims

1. Formula (I) 【Chemistry 1】 (In the formula, A is O or S; X is -CH 2 - or -CH 2 CH 2 - and R 1 is hydrogen, C 1 ~C 6 -Alkyl, C 2 ~C 6 -alkenyl, C 2 ~C 6 -alkynyl, C 1 ~C 6 -alkoxy, C 1 ~C 6 -haloalkyl, cyano-C 1 ~C 6 -Alkyl, C 1 ~C 4 -alkoxy-C 1 ~C 6 -Alkyl, C 1 ~C 4 -Alkylsulfonyl-C 1 ~C 4 -Alkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -Alkyl, C 3 ~C 6 -cycloalkyl, N—C 1 ~C 4 Alkoxy-imidoyl, N—C 1 ~C 4 -alkoxy-C 1 ~C 4 -Alkyl-imidoyl, C 4 ~C 8 -bicycloalkyl, 3-, 4-, 5-, or 6-membered heterocycloalkyl, phenyl, 5-, or 6-membered heteroaryl, phenyl-C 1 ~C 6 -alkyl or 5- or 6-membered heteroaryl-C 1 ~C 3 -alkyl, any of said 3-, 4-, 5- or 6-membered heterocycloalkyl being selected from N, O, S, S=O or SO 2 and wherein no more than one is O, S, S=O, or SO. 2 and the phenyl, phenyl-C 1 ~C 6 -alkyl, 5- or 6-membered heteroaryl and 5- or 6-membered heteroaryl-C 1 ~C 3 - any of the alkyls contain 1 or 2 heteroatoms individually selected from N or O, and any of the 3-, 4-, 5- or 6-membered heterocycloalkyls are unsubstituted or selected from halogen, cyano, C 1 ~C 3 Alkyl, C 1 ~C 3 Haloalkyl or C 3 ~C 6 cycloalkyl, wherein any of the phenyl and 5- or 6-membered heteroaryl is unsubstituted or substituted by one, two, or three substituents independently selected from halogen, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl or C 1 ~C 4 substituted by 1, 2 or 3 substituents independently selected from alkoxy; 3 ~C 6 -Cycloalkyl is unsubstituted or substituted with cyano, halogen, C 1 ~C 4 -Alkyl, C 1 ~C 3 -haloalkyl, C 1 ~C 4 -alkoxycarbonyl, C 1 ~C 4 -Alkylcarbonyl or C 1 ~C 4 -substituted by 1, 2 or 3 substituents independently selected from -alkylaminocarbonyl; R 1 is the formula (W) 【Chemistry 2】 (wherein the wavy line represents the position where the compound of formula (I) is bonded to the nitrogen of the amide group, and Y represents O, carbonyl, or C 1 ~C 2 alkyl, and R 8 is hydrogen, C 1 ~C 3 -Alkyl, C 1 ~C 3 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 3 -alkoxy, C 3 ~C 6 -halocycloalkyl, C 1 ~C 6 -alkoxy-C 1 ~C 3 - alkyl or phenyl, said phenyl being unsubstituted or selected from halogen or C 1 ~C 3 -substituted by 1 or 2 substituents independently selected from -alkyl is selected from the heterocycles R 2 is hydrogen, C 1 ~C 6 -Alkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkoxy, C 1 ~C 6 -alkoxy-C 1 ~C 6 -Alkyl, C 1 ~C 6 -Alkylcarbonyl or C 1 ~C 6 -alkoxycarbonyl, R 3 is hydrogen, halogen or C 1 ~C 3 - alkyl, R 4 is hydrogen, halogen or C 1 ~C 3 - alkyl, R 5 is hydrogen, C 1 ~C 4 -Alkyl or C 3 ~C 6 -cycloalkyl, R 6 is hydrogen, C 1 ~C 6 -Alkyl, C 1 ~C 6 -alkoxy, C 1 ~C 6 -Alkoxy C 1 ~C 6 -Alkyl, cyano-C 1 ~C 6 -Alkyl, C 1 ~C 6 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -Alkylcarbonyl or C 1 ~C 6 -alkoxycarbonyl, and R 7 is C 1 ~C 4 - alkylsulfonyl, C 1 ~C 4 -haloalkylsulfonyl or C 3 ~C 6 -cycloalkylsulfonyl, wherein the cycloalkyl is unsubstituted or selected from halogen, cyano, C 1 ~C 3 -Alkyl or C 1 ~C 3 -substituted by 1, 2, or 3 substituents independently selected from -haloalkyl or a salt or N-oxide thereof.

2. The compound of claim 1 , wherein A is O.

3. R 3 is hydrogen or methyl, and R 4 The compound according to claim 1 or 2, wherein is hydrogen.

4. R 5 The compound according to any one of claims 1 to 3, wherein is hydrogen or methyl.

5. R 6 is hydrogen, C 1 ~C 4 -Alkyl, C 1 ~C 2 -alkoxy or C 1 ~C 2 -alkoxy-C 1 ~C 4 The compound according to any one of claims 1 to 4, wherein - is alkyl.

6. R 6 The compound of claim 5 , wherein is hydrogen.

7. R 7 teeth, 【Transformation 3】 (wherein the wavy line represents the position bonded to the nitrogen) The compound according to any one of claims 1 to 6,

8. R 7 teeth, 【Chemistry 4】 (wherein the wavy line represents the position bonded to the nitrogen) 8. The compound of claim 7, wherein:

9. R 1 is hydrogen, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, C 1 ~C 3 -alkoxy, C 3 ~C 6 -cycloalkyl, cyano-C 1 ~C 4 -Alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 4 -Alkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 4 -Alkyl, N—C 1 ~C 4 Alkoxy-imidoyl or C 4 ~C 6 -bicycloalkyl, wherein said C 3 ~C 6 -Cycloalkyl is unsubstituted or substituted with cyano, halogen, C 1 ~C 4 -Alkyl, C 1 ~C 2 -haloalkyl, C 1 ~C 3 Alkoxycarbonyl, C 1 ~C 3 Alkylcarbonyl or C 1 ~C 3 substituted with one or two substituents independently selected from alkylaminocarbonyl; R 1 is the formula (W) 【Transformation 5】 (wherein the wavy line represents the position of the bond to the N atom of the amide group of the compound of formula (I), Y is carbonyl or CH 2 and R 8 is selected from hydrogen, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, or 2,2,2-trifluoroethyl.

9. The compound according to claim 1, wherein the heterocycle is selected from the group consisting of:

10. R 1 is hydrogen, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, C 1 ~C 2 -alkoxy, C 3 ~C 6 -cycloalkyl, cyano-C 1 ~C 4 -Alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 4 -Alkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 4 -alkyl, -C(CH 3 ) = NOCH 3 , -C(CH 3 ) = NOCH 2 CH 3 or C 4 ~C 6 -bicycloalkyl, wherein said C 3 ~C 6 -cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from cyano, halogen, methyl, ethyl, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, acetyl, methoxycarbonyl, or methylaminocarbonyl.

11. A composition comprising a compound according to any one of claims 1 to 10.

12. 12. The composition of claim 11, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

13. 13. A method for combating and controlling insects, mites or molluscs which comprises applying to the pest, the pest's habitat or plants which are susceptible to attack by the pest an insecticidally, acaricidally or molluscicidally effective amount of a compound of formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 11 or 12.

14. 13. A method for protecting plant propagation material from attack by insects, mites or mollusks, which method comprises treating the propagation material or the locus where the propagation material is to be planted with an effective amount of a compound of formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 11 or 12.

15. Plant propagation material, such as seeds, comprising or treated with or having attached thereto a compound of formula (I) according to any one of claims 1 to 10.

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