Alkoxyheteroaryl-carboxamide or thioamide compound

Abstract

Formula (I) [Chemical 1] JPEG2025516598000202.jpg29161(wherein the substituents are as defined in claim 1) The compounds of and the agriculturally acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds can be used as insecticides.

Description

Technical Field

[0001] The present invention relates to alkoxyheteroaryl-carboxamide or thioamide compounds that are pesticidally effective, particularly insecticidally effective, preferably substituted pyridinyl, pyrazinyl or pyridazinyl compounds thereof, a process for their preparation, compositions containing these compounds and their use for controlling animal pests, particularly insects, including arthropods.

Background Art

[0002] WO 2021 / 153720 describes certain alkoxybenzoic acid amide derivatives.

Summary of the Invention

Means for Solving the Problems

[0003] Here, certain novel alkoxy and cycloalkoxyheteroaryl-carboxamide or thioamide compounds that are pesticidally effective have been found.

[0004] Accordingly, in a first aspect, the present invention provides a compound of formula (I)

Chemical Formula

Chemical formula

Mode for Carrying Out the Invention

[0005] A compound of formula (I) having at least one basic centre can form, for example, an acid addition salt with, for example, an inorganic strong acid such as a mineral acid such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acid, a strong organic carboxylic acid such as an unsubstituted or C 1 ~C 4 alkanecarboxylic acid such as acetic acid, for example a saturated or unsaturated dicarboxylic acid such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, for example a hydroxycarboxylic acid such as ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or an acid addition salt with, for example, benzoic acid, or an organic sulfonic acid such as an unsubstituted or C 1 ~C 4 alkane- or arylsulfonic acid such as methane- or p-toluenesulfonic acid. A compound of formula (I) having at least one acidic group can form, for example, a salt with a base, for example an inorganic salt such as an alkali metal salt or an alkaline earth metal salt such as a sodium salt, potassium salt or magnesium salt or a salt with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamine such as ethyl-, diethyl-, triethyl- or dimethylpropylamine or mono-, di- or trihydroxy-lower alkylamine such as mono-, di- or triethanolamine.

[0006] In each case, the compound of formula (I) according to the invention is in free form, in oxidised form as N-oxide or in salt form, for example in an agriculturally usable salt form.

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

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

[0009] As used herein, “C 1 ~C n -alkyl” refers to a saturated straight-chain or branched hydrocarbon radical having 1 to n carbon atoms bonded through any of the carbon atoms, for example, radicals such as 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.

[0010] As used herein, “C 2 ~C n -alkenyl” refers to a straight-chain 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.

[0011] As used herein, “C 2 ~C nThe term "-alkynyl" refers to a straight-chain or branched alkynyl chain moiety having 2 to n carbon atoms and one triple bond, such as ethynyl, prop-2-ynyl, but-3-ynyl.

[0012] As used herein, "C" 3 ~C n -cycloalkyl" refers to a 3- to n-membered cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0013] As used herein, "C" 1 ~C n -alkoxy" refers to a straight-chain or branched saturated alkyl group having 1 to n carbon atoms (as described above) bonded through an oxygen atom, i.e., any one of the groups such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy. As used herein, "C" 2 ~C n -alkenyloxy" refers to a straight-chain or branched alkenyl chain having 1 to n carbon atoms (as described above) bonded through an oxygen atom.

[0014] As used herein, "C" 1 ~C n -alkoxy-C 1 ~C n -alkyl" refers to an alkyl group (as described above) substituted with a C 1 ~C n -alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

[0015] As used herein, "C" 3 ~C n -cycloalkyl-C 1 ~C n -alkyl" refers to a C 3 ~C n- An alkyl group substituted with a cycloalkyl group (as described above). Examples are cyclopropylmethyl and cyclopropylethyl. Similarly, the term "C 3 ~C n -halocycloalkyl-C 1 ~C n -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.

[0016] As used herein, the terms "heterocycloalkyl" or "heterocyclyl" refer to a stable 3-, 4-, 5- or 6-membered non-aromatic monocyclic ring group containing 1, 2 or 3 heteroatoms / groups independently selected from nitrogen, oxygen, sulfur, S=O and SO 2 A heterocyclyl group can be attached to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocyclyl 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. A heterocycloalkyl group can be substituted at the heteroatom and / or carbon atom. The term "cyanoheterocycloalkyl" indicates that a carbon atom in the heterocycloalkyl group is substituted with a cyano group.

[0017] As used herein, the term "heterocycloalkyl-C 3 ~C n -cycloalkyl" refers to a cycloalkyl group substituted with a heterocycloalkyl group (as described above). Heterocycloalkyl-C 3 ~C n-The cycloalkyl group may be substituted in the heterocycloalkyl group and / or the cycloalkyl group. Examples are 1-(tetrahydro-3-furanyl)cyclopropyl, 1-(tetrahydro-2-furanyl)cyclopropyl, 1-(tetrahydro-3-thienyl)cyclopropyl, 1-(3-pyrrolidinyl)cyclopropyl, 1-(tetrahydro-2H-pyran-4-yl)cyclopropyl, 1-(tetrahydro-3-furanyl)cyclobutanyl, 1- and (tetrahydro-3-furanyl)cyclopentanyl.

[0018] As used herein, the term "heterocycloalkyl-C 1 ~C n -alkyl" refers to an alkyl group substituted with a heterocycloalkyl group (as described above). The heterocycloalkyl-C 1 ~C n -alkyl group may be substituted in the heterocycloalkyl group and / or the alkyl group. Examples are (tetrahydrofuran-3-yl)methanyl (or (tetrahydrofuran-3-yl)methyl), 1,3-dioxolan-2-methanyl (or 1,3-dioxolan-2-methyl), 2-pyrrolidinemethanyl (or 2-pyrrolidinemethyl), and α-methyl-2-pyrrolidinemethanyl (or α-methyl-2-pyrrolidinemethyl).

[0019] As used herein, the term "cyano-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkyl group having 1 to n carbon atoms (as described above), where one of the hydrogen atoms in the group is substituted with a cyano group, such as cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-(cyanomethyl)-2-ethyl, 1-(methyl)-2-cyanoethyl, 4-cyanobutyl, etc. Similarly, the term "cyano-C 3 ~C n -cycloalkyl" refers to a C 3 ~C n- refers to a cycloalkyl group, and "cyano-C 3 ~C n -cycloalkyl-C 1 ~C n -alkyl" means a C 3 ~C n -alkyl group having a cyano-C 1 ~C n -cycloalkyl group.

[0020] Halogen generally refers to fluorine, chlorine, bromine or iodine. This equally applies to halogen combined with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy and halocycloalkyl.

[0021] As used herein, "C 1 ~C nThe term "-haloalkyl" refers to a straight-chain or branched saturated alkyl radical having from 1 to n carbon atoms, attached through any of the carbon atoms (as described above), where some or all of the hydrogen atoms in these radicals may be replaced by fluorine, chlorine, bromine and / or iodine, i.e. for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl. "C 1 ~C 2 The term "C 1 ~C 2 -fluoroalkyl" refers to a C 2 ~C n -haloalkenyl" or "C 2 ~C nThe term "-haloalkynyl" refers to a C substituted with one or more halo atoms, which may be the same or different, 2 ~C n -alkenyl or C 2 ~C n -alkynyl group. Similarly, as used herein, "C 3 ~C n -halocycloalkyl" or "C 1 ~C n -haloalkoxy" refers to a C substituted with one or more halo atoms, which may be the same or different, 3 ~C n -cycloalkyl group or C 1 ~C n -alkoxyl group.

[0022] As used herein, the term "hydroxy-C 3 ~C n -cycloalkyl" or "carbamoyl-C 3 ~C n -cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with a hydroxy (OH) group or a carbamoyl (NHC(=O)) group.

[0023] As used herein, the term "C 1 ~C n -alkyl-carbonyl-oxy-C 3 ~C n -cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with an R a C(=O)O- moiety (wherein R a is a C 1 ~C n -alkyl group).

[0024] As used herein, the term "carboxy-C 3 ~C n -cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with a C(=O)(O)- moiety.

[0025] As used herein, "C 1 ~Cn -alkoxycarbonyl-C 3 ~C n The term "-cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with an R c C(=O)-moiety (wherein R c is a C 1 ~C n -alkoxy group as defined above). As used herein, "C 1 ~C n -alkylsulfonyloxy-C 3 ~C n The term "-cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with an R a S(O) 2 O-moiety (wherein R a is a C 1 ~C n -alkyl group as defined above).

[0026] As used herein, the term "C 1 ~C n -alkoxy-C 3 ~C n -cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with a C 1 ~C n -alkoxy group as defined above. Similarly, as used herein, the terms "C 1 ~C n -haloalkoxy-C 3 ~C n -cycloalkyl" or "C 2 ~C n -alkynyl-C 3 ~C n -cycloalkyl" each refer to a 3- to n-membered cycloalkyl group substituted with a C 1 ~C n -haloalkoxy group or a C 2 ~C n -alkynyl group as defined above.

[0027] As used herein, the terms "C 1 ~C n -alkylthio" or "C 1 ~Cn The term "-alkylsulfanyl" refers to a C 1 ~C n -alkyl group bonded through a sulfur atom.

[0028] As used herein, the term "C 1 ~C n -haloalkylthio" or "C 1 ~C n -haloalkylsulfanyl" refers to a C 1 ~C n haloalkyl group bonded through a sulfur atom.

[0029] As used herein, the term "C 1 ~C n -alkylsulfinyl" refers to a C 1 ~C n alkyl group bonded through the sulfur atom of a sulfinyl (or S(=O)-) group.

[0030] As used herein, the term "C 1 ~C n -alkylsulfonyl" refers to a C 2 ~C 1 alkyl group bonded through the sulfur atom of a sulfonyl (or S(=O) n -) group.

[0031] As used herein, the term "C 1 ~C n -alkylsulfonyl-C 1 ~C n -alkyl" refers to a C 1 ~C n alkyl group substituted with a C 1 ~C n alkylsulfonyl group.

[0032] As used herein, the term "C 1 ~C n -alkylthio-C 3 ~C n -cycloalkyl" refers to a C 1 ~Cn -alkylthio (or R a S-) moiety (wherein R a is a C 1 ~C n -alkyl group) refers to a 3- to n-membered cycloalkyl group substituted therewith. Similarly, as used herein, the term "C 1 ~C n -alkylsulfinyl-C 3 ~C n -cycloalkyl" or "C 1 ~C n -alkylsulfonyl-C 3 ~C n -cycloalkyl" refers to a C 1 ~C n -alkylsulfinyl (or R a S(O)-) or C 1 ~C n -alkylsulfonyl (or R a S(O) 2 -) moiety (wherein R a is a C 1 ~C n -alkyl group) refers to a 3- to n-membered cycloalkyl group substituted therewith.

[0033] As used herein, the term "C 1 ~C n -haloalkylthio-C 3 ~C n -cycloalkyl" refers to a C 1 ~C n -haloalkylthio (or R b S-) moiety (wherein R b is a C 1 ~C n -haloalkyl group) refers to a 3- to n-membered cycloalkyl group substituted therewith. Similarly, as used herein, the term "C 1 ~C n -haloalkylsulfinyl-C 3 ~C n -cycloalkyl" or "C 1 ~C n -haloalkylsulfonyl-C 3 ~C nThe term "-cycloalkyl" refers to a 3- to n-membered cycloalkyl group substituted with a C 1 ~C n -haloalkylsulfinyl (or R b S(O)-) or a C 1 ~C n -haloalkylsulfonyl (or R b S(O) 2 -) moiety (wherein R b is a C 1 ~C n -haloalkyl group).

[0034] As used herein, the term "C 1 ~C n -haloalkylsulfonylamino" refers to a C 1 ~C n -haloalkylsulfonyl (or R b S(O) 2 -) group attached through the nitrogen atom of an amino (or N-H) group (wherein R b is the C 1 ~C n -haloalkyl group as defined above).

[0035] As used herein, the term "C 1 ~C n -alkylcarbonyl" refers to a C 1 ~C n -alkyl group attached through the carbon atom of a carbonyl (C=O) group.

[0036] As used herein, the term "C 1 ~C n -alkoxycarbonyl" refers to a C 1 ~C n -alkoxy moiety attached through the carbon atom of a carbonyl (or C=O) group.

[0037] As used herein, the term "C 1 ~C n -alkoxycarbonyl-C 1 ~C 6The term "-alkyl" refers to a C 1 ~C n -alkyl group substituted with an -alkoxycarbonyl group. 1 ~C n

[0038] As used herein, the term "benzoyl" refers to a phenyl group bonded through the carbon atom of a carbonyl (C=O) group.

[0039] As used herein, the term "C 1 ~C n -haloalkoxycarbonyl" refers to a C 1 ~C n -haloalkoxy group bonded through the carbon atom of a carbonyl (C=O) group.

[0040] As used herein, the term "C 2 ~C n -alkenyloxycarbonyl" refers to a C 2 ~C n -alkenyloxycarbonyl group bonded through the carbon atom of a carbonyl (C=O) group.

[0041] As used herein, the term "C 1 ~C n -alkylaminocarbonyl" refers to a C 1 ~C n -alkylamino group (or R a NHC(=O)- (wherein R a is a C 1 ~C n -alkyl group)).

[0042] As used herein, the term "aminocarbonyl-C 1 ~C n -alkyl" refers to a C 2 ~C 1 ~C n -alkyl group substituted with an aminocarbonyl (or NH

[0043] As used herein, "C 1 ~C n -alkylaminocarbonyl-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkylaminocarbonyl (or R a NHC(=O)-) group (wherein R a is a C 1 ~C n -alkyl group) substituted C 1 ~C n -alkyl group. The C 1 ~C n -alkyl group bonded to nitrogen may be substituted.

[0044] As used herein, "C 3 ~C n -cycloalkylaminocarbonyl-C 1 ~C n -alkyl" refers to a C 3 ~C n -cycloalkylaminocarbonyl (or R d NHC(=O)-) group (wherein R d is a C 3 ~C n -cycloalkyl group) substituted C 1 ~C n -alkyl group. The C 3 ~C n -cycloalkyl group bonded to nitrogen may be substituted.

[0045] As used herein, "C 1 ~C n -haloalkylaminocarbonyl-C 1 ~C n -alkyl" refers to a C 1 ~C n -haloalkylaminocarbonyl (or R b NHC(=O)-) group (wherein R b is a C 1 ~C n -haloalkyl group) substituted C1 ~C n - refers to an alkyl group. C bonded to nitrogen 1 ~C n - The haloalkyl group may be substituted.

[0046] As used herein, "C 1 ~C n - haloalkylcarbonyl-C 1 ~C n - alkyl" means a C 1 ~C n - haloalkylcarbonyl (or R b C(=O)-) group (wherein R b is a C 1 ~C n - haloalkyl group) substituted C 1 ~C n - alkyl group.

[0047] As used herein, "C 1 ~C n - alkylcarbonyloxy-C 1 ~C n - alkyl" means a C 1 ~C n - alkylcarbonyloxy (or R a C(=O)O-) group (wherein R a is a C 1 ~C n - haloalkyl group) substituted C 1 ~C n - alkyl group.

[0048] As used herein, "C 1 ~C n - alkoxycarbonyloxy-C 1 ~C n - alkyl" means a C 1 ~C n - alkoxycarbonyloxy (or R c C(=O)O-) group (wherein R c is a C 1 ~C n - alkoxy group) substituted C 1 ~Cn - refers to an alkyl group. C bonded to nitrogen 1 ~C n - alkoxy group may be substituted.

[0049] As used herein, "C 1 ~C n - alkylaminocarbonyl - C 3 ~C n - cycloalkyl" refers to a C 1 ~C n - alkylaminocarbonyl (or R a NHC(=O)- group (wherein R a is a C 1 ~C n - alkyl group)) - substituted C 3 ~C n - cycloalkyl group. C 1 ~C n - alkylaminocarbonyl - C 3 ~C n - cycloalkyl group may be substituted in the alkyl group and / or cycloalkyl group.

[0050] As used herein, "C 4 ~C n - bicycloalkyl" refers to a bicyclic non - aromatic ring system consisting of only carbon and hydrogen atoms and containing two fused rings (i.e., sharing two carbon atoms). Examples are 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, octahydro - 1 - pentalenyl.

[0051] As used herein, "C 1 ~C n - alkoxyimino" refers to a C 1 ~C n - alkoxy group bonded through the nitrogen atom of the imino (N=) moiety.

[0052] As used herein, the term "hydroxyimino" refers to a hydroxy group bonded through the nitrogen atom of the imino (N=) moiety.

[0053] As used herein, "hydroxyamino-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkyl group substituted with a hydroxyamino (or (OH)NH-) moiety.

[0054] As used herein, "C 1 ~C n -alkoxyimino-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkyl group substituted with a C 1 ~C n -alkoxyimino moiety.

[0055] As used herein, "C 1 ~C n -haloalkoxyimino-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkoxyimino moiety (wherein the C 1 ~C n -alkoxy group is substituted with one or more identical or different halogen atoms) substituted C 1 ~C n -alkyl group.

[0056] The term "phenyl-C 1 ~C n -alkyl" refers to a C 1 ~C n -alkyl group substituted with a phenyl ring. Examples include benzyl. The phenyl-C 1 ~C n -alkyl group may be substituted in the alkyl group and / or the phenyl group.

[0057] The term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, 3, or 4 heteroatoms independently 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-C 1 ~C n -alkyl" or "heteroaryl-C 3 ~C n -cycloalkyl" refers to a C 1 ~C n -alkyl or C 3 ~C n -cycloalkyl group substituted with a heteroaryl group, respectively. A heteroaryl-C 1 ~C n -alkyl or heteroaryl-C 3 ~C n -cycloalkyl group may be appropriately substituted in the heteroaryl, alkyl, and / or cycloalkyl groups.

[0058] As used herein, the term "sulfamoyl" refers to an amino (NH 2 ) moiety bonded through the sulfur atom of the sulfonyl (SO 2 ) moiety.

[0059] As used herein, the term "C 1 ~C n -alkylaminosulfonyl" refers to a C 2 ) moiety. 1 ~C n -alkylamino (or R a NHC(=O)-) moiety (wherein R a is a C 1 ~C n -alkyl group)) bonded through the sulfur atom of the sulfonyl (SO

[0060] As used herein, the term "optionally substituted" means that the substituent may be one or more identical or different substituents, for example 1, 2 or 3 R x substituents, and may or may not have them. For example, C substituted with 1, 2 or 3 halogens 1 ~C 6 Alkyl is not particularly limited, but -CH 2 Cl, -CHCl 2 , -CCl 3 , -CH 2 F, -CHF 2 , -CF 3 , -CH 2 CF 3 or -CF 2 CH 3 groups may be obtained. As another example, C substituted with 1, 2 or 3 halogens 1 ~C 6 Alkoxy is not particularly limited, but CH 2 ClO-, CHCl 2 O-, CCl 3 O-, CH 2 FO-, CHF 2 O-, CF 3 O-, CF 3 CH 2 O- or CH 3 CF 2 groups may be included. The term "optionally substituted" can be used synonymously with the term "unsubstituted or substituted".

[0061] As used herein, the term "control" refers to reducing the number of pests, eradicating pests, and / or preventing further damage by pests so as to reduce damage to plants or plant-derived products.

[0062] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, and the storage of plant-derived products (such as fruits, grains, and lumber); and pests related to damage to artificial structures. The term "pest" encompasses all stages in the life cycle of the pest.

[0063] As used herein, the term "effective amount" refers to the amount of a compound or a salt thereof that brings about the desired effect upon single or multiple applications.

[0064] As used herein, the term "room temperature", or "RT", or "rt" refers to a temperature of about 15°C to about 35°C. For example, rt may refer to a temperature of about 20°C to about 30°C, and rt may refer to a temperature of about 25°C.

[0065] The effective amount can be readily determined by one of ordinary skill in the art by using known techniques and observing the results obtained under similar circumstances. In determining the effective amount, a number of factors are considered, including, but not limited to, the type of plant or product derived from the plant to which it is applied; the pest to be controlled and its life cycle; the particular compound to be applied; the type of application; and other relevant circumstances.

[0066] In one embodiment of the present invention, formula (I)

Chemical formula

[0067] In one embodiment, the compound of formula (I) is of formula (I-1), (I-2), (I-3) or (I-4)

Chemical formula

[0068] In one embodiment, the compound of formula (I) is of formula (I-1a), (I-2a), (I-3a) or (I-4a)

Chemical formula

[0069] In one embodiment, the compounds represented by formulas (I-1a), (I-2a), (I-3a) and (I-4a) are the (S) enantiomer.

[0070] Embodiments according to the present invention are provided as described below.

[0071] In embodiments of each aspect of the present invention, A is A. Oxygen; or B. Sulfur is.

[0072] In embodiments of each aspect of the present invention, A. One or two of X, Y and Z is N, and the rest is CR 8 ; or B. X is N, and Z and Y are each CR 8 ; or C. X and Z are N, and Y is CR 8 ; or D. X and Y are N, and Z is CR 8 ; or E. Y is N, and X and Z are each CR 8 ; F. X is N, and Z and Y are each CH; or G. X and Z are N, and Y is CH; or H. X and Y are N, and Z is CH; or I. Y is N, and X and Z are each CH.

[0073] In embodiments of each aspect of the present invention, R 1 is A. hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 2 ~C 6 -alkynyl, C 3 ~C 6 -cycloalkyl, cyano-C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -halocycloalkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, heterocyclyl or C 1 ~C 6 -alkoxy-C 3 ~C 6 -cycloalkyl; or B. hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 2 ~C 4 -alkynyl, C 3 ~C 4 -cycloalkyl, cyano-C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, 4- or 5-membered heterocyclyl or C 1 ~C 3 -alkoxy-C 3 ~C 4 -cycloalkyl; or C. C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 2 ~C 6 -alkynyl, C 3 ~C6 -Cycloalkyl, C 3 ~C 6 -Halocycloalkyl, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 -Alkyl, 4-membered heterocyclyl or cyano-C 3 ~C 6 -Cycloalkyl; or D.C 1 ~C 3 -Alkyl, C 1 ~C 3 -Haloalkyl, C 2 ~C 4 -Alkynyl, C 3 ~C 4 -Cycloalkyl, C 3 ~C 4 -Halocycloalkyl, C 3 ~C 4 -Cycloalkyl-C 1 ~C 3 -Alkyl, SO 2 having 4-membered heterocyclyl or cyano-C 3 ~C 4 -Cycloalkyl; or E. Ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietan-3-yl or cyclopropylmethyl is.

[0074] In embodiments of each aspect of the present invention, R 2 is A. Hydrogen, C 1 ~C 6 -Alkyl, C 1 ~C 6 -Haloalkyl, C 3 ~C 6 -Cycloalkyl, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 -Alkyl, C 1 ~C 6-alkoxy-C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkoxy-C 1 ~C 6 -alkyl or C 1 ~C 6 -alkylcarbonyl; or B. Hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy-C 3 ~C 4 -cycloalkyl, C 1 ~C 3 -alkoxy-C 1 ~C 3 -alkyl or C 1 ~C 3 -alkylcarbonyl; or C. Hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkylcarbonyl or C 1 ~C 6 -alkoxycarbonyl; or D. Hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkylcarbonyl or C 1 ~C 3 -alkoxycarbonyl; or E. Hydrogen, methyl, acetyl or 2-methylpropanoyl is.

[0075] In an embodiment of each aspect of the present invention, R 3 is A. Halogen, C 1 ~C6 - alkyl or cyano; or B. halogen, C 1 ~C 3 - alkyl or cyano; or C. chlorine, methyl or cyano; or D. chlorine or bromine; or E. chlorine is.

[0076] In an embodiment of each aspect of the present invention, R 4 is

Chemical formula

[0077] In an embodiment of each aspect of the present invention, R 5 is A. C 1 ~C 6 - alkylsulfonylamino (the amino group may be substituted by R 6 ), C 1 ~C 6 - haloalkylsulfonylamino (the amino group may be substituted by R 6 ) and C 9 ~C 3 ~C 6 - cycloalkylsulfonylamino (the amino group may be substituted by R 6 ); or B. C 1 ~C 3 - alkylsulfonylamino (the amino group may be substituted by R 6 ), C 1 ~C 3 - haloalkylsulfonylamino (the amino group may be substituted by R 6 ) or C 9 ~C 3 ~C 6 - cycloalkylsulfonylamino (the amino group may be substituted by R 6 ); or C. Isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino, dichloromethylsulfonylamino or cyclopropylsulfonylamino; or D. Isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino or cyclopropylsulfonylamino; or E. Difluoromethylsulfonylamino or trifluoromethylsulfonylamino is.

[0078] In an embodiment of each aspect of the present invention, R 6 is A. Hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkoxy-C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl or C 1 ~C 6 -alkylcarbonyl; or B. Hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 3 -alkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl or C 1 ~C 3 -alkylcarbonyl; or C. Hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl is.

[0079] In an embodiment of each aspect of the present invention, R 7 is A.C 1 ~C3 -alkyl, C 1 ~C 3 -haloalkyl or R 9 which may be mono- or polysubstituted by C 3 ~C 4 -cycloalkyl, or B. methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl or cyclopropyl; or C. methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, dichloromethyl or cyclopropyl; or D. isopropyl, trifluoromethyl, difluoromethyl or cyclopropyl is.

[0080] In an embodiment of each aspect of the present invention, R 8 is A. hydrogen, halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano; or B. hydrogen, chloro, bromo, fluoro, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano; or C. hydrogen is.

[0081] In an embodiment of each aspect of the present invention, R 9 is A. halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano; or B. chloro, bromo, fluoro, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano is.

[0082] In embodiments of each aspect of the present invention, R 10 is A. halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, C 3 ~C 4 -halocycloalkyl-C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkoxy, C 1 ~C 3 -alkylthio, C 1 ~C 3 -haloalkylthio, C 1 ~C 3 -alkylsulfinyl, C 1 ~C 3 -haloalkylsulfinyl, C 1 ~C 3 -alkylsulfonyl, C 1 ~C 3 -haloalkylsulfonyl, C 1 ~C 3 -alkylthio-C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkylthio-C 1 ~C 3 -alkyl, C 1 ~C 3 -alkylsulfonyloxy, C 1 ~C 3 -haloalkylsulfonyloxy, phenyl (which is halogen, C 1 ~C 6 -alkyl and C 1 ~C 6- independently selected from haloalkyl and optionally mono- or polysubstituted), phenyl-C 1 ~C 3 - alkyl, phenyl-C 1 ~C 3 - alkoxy, cyano or nitro; or B. chloro, bromo, fluoro, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano is.

[0083] The present invention thus provides compounds of formula (I) having A, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 and R 10 in any combination / permutation.

[0084] Thus, A is Embodiment A (i.e., A is oxygen); X, Y and Z are Embodiment A (i.e., one or two of X, Y and Z are N, and the rest are CR 8 ); R 1 is Embodiment B (i.e., R 1 is hydrogen, C 1 ~C 3 - alkyl, C 1 ~C 3 - haloalkyl, C 2 ~C 4 - alkynyl, C 3 ~C 4 - cycloalkyl, cyano-C 3 ~C 4 - cycloalkyl, C 3 ~C 4 - halocycloalkyl, C 3 ~C 4 - cycloalkyl-C 1 ~C 3 - alkyl, 4- or 5-membered heterocyclyl or C 1 ~C 3 - alkoxy-C3 ~C 4 -cycloalkyl); R 2 is Embodiment C (i.e., R 2 is hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkylcarbonyl or C 1 ~C 6 -alkoxycarbonyl); R 3 is Embodiment B (i.e., R 3 is halogen, C 1 ~C 3 -alkyl or cyano); R 4 is the first aspect (i.e., R 4 is C 5 monosubstituted or polysubstituted by R 1 ~C 6 -alkyl or R 5 monosubstituted or polysubstituted by R 3 ~C 6 -cycloalkyl); R 5 is Embodiment B (i.e., R 5 is C 1 ~C 3 -alkylsulfonylamino (the amino group may be substituted by R 6 ), C 1 ~C 3 -haloalkylsulfonylamino (the amino group may be substituted by R 6 ), and C 9 monosubstituted or polysubstituted by R 3 ~C 6 -cycloalkylsulfonylamino (the amino group may be substituted by R 6 ); R 6 is Embodiment B (i.e., R 6 is hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 3 -alkyl, C 3 ~C 4 -cycloalkyl-C1 ~C 3 -alkyl or C 1 ~C 3 -alkylcarbonyl); and R 9 is of the first embodiment (i.e., R 9 is halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano), a compound of formula (I) is provided, for example.

[0085] Preferably, A is of embodiment A (i.e., A is oxygen); X, Y and Z are of embodiment A (i.e., one or two of X, Y and Z are N, and the rest are CR 8 ); R 1 is of embodiment B (i.e., R 1 is hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 2 ~C 4 -alkynyl, C 3 ~C 4 -cycloalkyl, cyano-C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, a 4- or 5-membered heterocyclyl or C 1 ~C 3 -alkoxy-C 3 ~C 4 -cycloalkyl); R 2 is of embodiment C (i.e., R 2 is hydrogen, C 1 ~C 6 -alkyl, C 1 ~C6 -alkylcarbonyl or C 1 ~C 6 -alkoxycarbonyl); R 3 is Embodiment B (i.e., R 3 is halogen, C 1 ~C 3 -alkyl or cyano); R 4 is

Chemical formula

[0086] In embodiments of each aspect of the present invention, R 1 is hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 2 ~C 6 -alkynyl, C 3 ~C 6 -cycloalkyl, cyano-C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -halocycloalkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, heterocyclyl or C 1 ~C 6 -alkoxy-C 3 ~C 6 -cycloalkyl; R 2 is hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, C 1 ~C 6 -alkoxy-C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkoxy-C 1 ~C 6 -alkyl or C 1 ~C 6 -alkylcarbon; R 3 is halogen, C1 ~C 6 -alkyl or cyano; R 4 is

Chemical formula

[0087] In embodiments of each aspect of the present invention, R 1 is C 1 ~C 6 -alkyl, C1 ~C 6 - haloalkyl, C 2 ~C 6 - alkynyl, C 3 ~C 6 - cycloalkyl, C 3 ~C 6 - halocycloalkyl, C 3 ~C 6 - cycloalkyl-C 1 ~C 6 - alkyl, 4-membered heterocyclyl or cyano-C 3 ~C 6 - cycloalkyl; R 2 is hydrogen, C 1 ~C 6 - alkyl, C 1 ~C 6 - alkylcarbonyl or C 1 ~C 6 - alkoxycarbonyl; R 3 is halogen, C 1 ~C 3 - alkyl or cyano; R 4 is

Chemical formula

[0088] In embodiments of each aspect of the present invention, R 1 is ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietan-3-yl or cyclopropylmethyl; R 2 is hydrogen, methyl, acetyl or 2-methylpropanoyl; R 3 is chlorine, methyl or cyano; R 4 is

Chemical formula

[0089] In an embodiment of each aspect of the present invention, R 1 is ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietan-3-yl or cyclopropylmethyl; R 2 is hydrogen, methyl, acetyl or 2-methylpropanoyl; R 3 is chlorine, bromine or methyl; R 4 is

Chemical formula

[0090] In an embodiment of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a), R 1 as, hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 2 ~C 6 -alkynyl, C 3 ~C 6 -cycloalkyl, cyano-C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -halocycloalkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, C 1 ~C 6 -alkyl, heterocyclyl or C 1 ~C 6 -alkoxy-C 3 ~C 6 -cycloalkyl; R 2 as, hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, C1 ~C 6 -alkoxy-C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkoxy-C 1 ~C 6 -alkyl or C 1 ~C 6 -alkylcarbon; R 3 as, halogen, C 1 ~C 6 -alkyl or cyano; R 6 as, hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 3 -alkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl or C 1 ~C 3 -alkylcarbonyl; and R 7 as, C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl or R 9 optionally mono- or polysubstituted by C 3 ~C 4 -cycloalkyl (wherein R 9 is halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano).

[0091] In embodiments of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a) is R 1as ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietan-3-yl or cyclopropylmethyl; R 2 as hydrogen, methyl, acetyl or 2-methylpropanoyl; R 3 as chlorine, bromine or methyl; R 6 as hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and R 7 as C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl or R 9 which may be mono- or polysubstituted by C 3 ~C 4 -cycloalkyl (wherein R 9 is halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano).

[0092] In embodiments of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a) is R 1 as ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietan-3-yl or cyclopropylmethyl; R 2 as hydrogen, methyl, acetyl or 2-methylpropanoyl; R 3 as chlorine, bromine or methyl; R 6 as hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and R 7 as C 1 ~C 3 -alkyl, C 1 ~C 3- Haloalkyl or R 9 which may be mono - or polysubstituted by C 3 ~ C 4 - Cycloalkyl (wherein R 9 is halogen, C 1 ~ C 3 - Alkyl, C 1 ~ C 3 - Alkoxy, C 1 ~ C 3 - Haloalkyl or cyano).

[0093] In a further embodiment of the present invention, the compound of formula (I) is of formula (I - 1)

Chemical formula

Chemical formula

[0094] In a further embodiment of the present invention, the compound of formula (I) is of formula (I-1a)

Chemical formula

[0095] In a further embodiment of the present invention, the compound of formula (I) is of formula (I-1a)

Chemical formula

[0096] In a further embodiment of the present invention, the compound of formula (I) is of formula (I-1a)

Chemical formula

[0097] In one embodiment, the compound of formula (I) is of formula (I-5a)

Chemical formula

[0098] Preferably, in the compound of formula (I-5a), X is N; Y and Z are CH; R 1 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 2 ~C 4 -alkynyl, C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, 4-membered heterocyclyl or cyano-C 3 ~C 4 -cycloalkyl; R 3 is halogen; R 6 is hydrogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy-C 1 ~C 3 -alkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl or C 1 ~C 3 -alkylcarbonyl; R 7 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl or R 9 which may be mono- or polysubstituted by C 3 ~C 4 -cycloalkyl; and R 9 is halogen, C 1 ~C 3 -alkyl, C 1~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano.

[0099] Preferably, in the compound of formula (I-5a), X is N; Y and Z are CH; R 1 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 2 ~C 4 -alkynyl, C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, 4-membered heterocyclyl or cyano-C 3 ~C 4 -cycloalkyl; R 3 is chlorine, bromine or methyl; R 6 is hydrogen; R 7 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl or R 9 which may be mono- or polysubstituted by 3 ~C 4 -cycloalkyl; and R 9 is halogen, C 1 ~C 3 -alkyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -haloalkyl or cyano.

[0100] Preferably, in the compound of formula (I-5a), X is N; Y and Z are CH; R 1 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl, C 2 ~C 4 -alkynyl, C 3 ~C 4 -cycloalkyl, C 3 ~C 4 -halocycloalkyl, C 3 ~C 4 -cycloalkyl-C 1 ~C 3 -alkyl, 4-membered heterocyclyl or cyano-C 3 ~C 4 -cycloalkyl; R 3 is chlorine, bromine or methyl; R 6 is hydrogen; R 7 is C 1 ~C 3 -alkyl, C 1 ~C 3 -haloalkyl or C 3 ~C 4 -cycloalkyl.

[0101] In one embodiment of the present invention, the compound of formula (I) according to the present invention is selected from the compounds listed in any one of Tables 1 to 5.

[0102] In another embodiment of the present invention, the compound of formula (I) according to the present invention is selected from the compounds listed in Table P (below).

[0103] Preferably, the compound of formula (I) according to the present invention is 2-chloro-N-cyclopropyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(2,2,2-trifluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-cyclopropyl-5-[(2S)-2-(dichloromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 2-chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-[methyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, [[(1S)-2-[[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl]oxy]-1-methyl-ethyl]-(trifluoromethylsulfonyl)amino]methyl 2-methylpropanoate, 2-chloro-N-cyclopropyl-5-[(2S)-2-(difluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-tert-butyl-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-acetyl-2-chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide,[[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl]oxy]-1-methyl-ethyl]-(trifluoromethylsulfonyl)amino]methyl 2-methylpropanoate, methyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 2-chloro-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]-N-cyclopropyl-pyridine-3-carboxamide, 2-chloro-N-cyclopropyl-5-[(2S)-2-[methyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-chloro-N-cyclopropyl-5-[2-(trifluoromethylsulfonylamino)ethoxy]pyridine-3-carboxamide, 2-chloro-N-(5-cyano-3-fluoro-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(5-chloro-3-fluoro-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(5-chloro-3-methyl-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]-N-(2,4,6-trifluorophenyl)pyridine-3-carboxamide, 2-chloro-N-(4-cyano-2-fluoro-phenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(2,4-difluorophenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(2-fluoro-4-methylsulfonyl-phenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide,2-Chloro-N-(4-chloro-2-fluoro-phenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[1-[2-(5-cyano-2-pyridyl)-1,2,4-triazol-3-yl]ethyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(5-chloro-2-pyridyl)methyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(2E)-2-methoxyimino-1,1-dimethyl-ethyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-methyl-N-[3-oxo-2-(2,2,2-trifluoroethyl)isoxazolidin-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-cyclopropylethyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(3-chloro-2-pyridyl)methyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(2,4-difluorophenyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-isopropyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[1-(4-fluorophenyl)-2-oxo-pyrrolidin-3-yl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-ethyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamideN-(3,3-Difluorocyclobutyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-methyl-N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(2,2-difluoroethyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-cyclopropyl-N,2-dimethyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(cyclopropylmethoxy)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 5-[(2S)-2-[acetyl(trifluoromethylsulfonyl)amino]propoxy]-2-chloro-N-cyclopropyl-pyridine-3-carboxamide, N-benzyl-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyclopropylethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-[(1-cyanocyclopropyl)methyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyanocyclopropyl)-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyanocyclobutyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide,2-chloro-N-[(4S)-2-ethyl-3-oxo-isoxazolidin-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-ethyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(3-methyltetrahydrofuran-3-yl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-prop-2-ynyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-[2-(cyclopropylmethylamino)-2-oxo-ethyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-[3-oxo-2-(2,2,2-trifluoroethyl)isoxazolidin-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(2,2-difluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-phenyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyano-1-methyl-ethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-cyclopropyl-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(2,2-difluoroethyl)-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(4-fluoro-2-methyl-phenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide,N-Cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-2-methyl-pyridine-3-carboxamide, N-cyclopropyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-N-(2,2,2-trifluoroethyl)pyridine-3-carboxamide, 2-chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-chloro-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy], Pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1-cyanocyclopropyl)-N,5-dimethyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(4-ethylthiazol-5-yl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1,3-dihydroisobenzofuran-5-ylmethyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-methyl-N-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[2-(2-fluorophenoxy)ethyl]-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(5-methoxy-1,1-Dimethyl-penta-2-ynyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1-cyclopropylethyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[1-(2-ethylthiazol-4-yl)ethyl]-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(3-cyano-2-fluoro-phenyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-methyl-N-[1-(3-pyridyl)ethyl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-benzyl-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-5-methyl-pyridine-4-carboxamide, N-(1-cyanocyclopropyl)-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-5-methyl-pyridine-4-carboxamide, 5-methyl-N-(2,2,Selected from 2-(trifluoroethyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-bromo-N-cyclopropyl-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-4-carboxamide, 5-bromo-N-(1-cyanocyclopropyl)-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-4-carboxamide, 5-bromo-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-bromo-N-[(4R)-2-ethyl-3-oxoisoxazolidin-4-yl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-bromo-N-(2,2,2-trifluoroethyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-bromo-N-(1-cyanocyclopropyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-chloro-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 3-chloro-N-cyclopropyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide, 3-chloro-N-(1-cyanocyclopropyl)-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide or N-(1-bicyclo[1.1.1]pentanyl)-3-chloro-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide.,

[0104] More preferably, the compound of formula (I) according to the present invention is selected from 2-chloro-N-cyclopropyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide or 2-chloro-N-(2,2,2-trifluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide.

[0105] In a second aspect, the present invention provides a composition comprising a compound of formula (I) as defined in the first aspect, one or more auxiliaries and diluents and optionally one or more other active ingredients.

[0106] In a third aspect, the present invention provides a method for controlling and preventing insects, mites, nematodes or molluscs, which comprises applying an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound as defined in the first aspect or the composition as defined in the second aspect to a pest, the habitat of the pest or a plant susceptible to attack by the pest.

[0107] In a fourth aspect, the present invention provides a method for protecting plant propagation material from attack by insects, mites, nematodes or molluscs, which comprises treating the propagation material or the location where the propagation material is planted with an effective amount of the compound of formula (I) as defined in the first aspect or the composition as defined in the second aspect.

[0108] In a fifth aspect, the present invention provides plant propagation material such as seeds, which comprises, is treated with or is adhered to the compound of formula (I) as defined in the first aspect or the composition as defined in the second aspect.

[0109] In a further aspect, the present invention provides a method for controlling a parasite in or on an animal in need thereof, which method comprises administering an effective amount of a compound of formula (I) as defined in the first aspect. The present invention further provides a method for controlling an ectoparasite on an animal in need thereof, which method comprises administering an effective amount of a compound of formula I as defined in the first aspect. The present invention further provides a method for preventing and / or treating a disease infected by an ectoparasite, which method comprises administering an effective amount of a compound of formula (I) as defined in the first aspect to an animal in need thereof.

[0110] The compounds of formula (I) can be prepared by those skilled in the art according to known methods. More specifically, the compounds and intermediates of formula I can thus be prepared as described below in the schemes and examples. Certain stereogenic centers are left unspecified for the sake of brevity and are not intended to limit the teachings of the schemes in any way.

[0111] The compound of formula (I) according to the present invention (wherein R 1 , R 2 , R 3 , R 4 , X, Y, Z are as defined for formula (I), and A is oxygen) can be obtained by converting a compound of formula (III) (wherein R 1 and R 2 are as defined for formula (I)) via an intermediate acid chloride or activating acylating agent to a compound of formula (II) (wherein R 3 , R 4 , X, Y, Z are as defined for formula (I)) as described below. This is shown in Scheme 1 below. Scheme 1

Chemical formula

[0112] As shown in Scheme 1, compound II is activated to the compound of formula IV by methods known to those skilled in the art and, for example, by the methods described in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula IV where G is halogen is formed by treatment of the compound of formula II with, for example, oxalyl chloride or thionyl chloride in an inert solvent such as dichloromethane or THF in the presence of a catalytic amount of DMF at a temperature of 25-170 °C, preferably 25-80 °C. Optionally, treatment of the compound of formula II in the presence of a base such as, for example, triethylamine or pyridine with a compound of formula III (wherein R 1 and R 2 are as defined in formula I) affords the compound of formula I. Alternatively, the compound of formula I can be prepared by treatment of the compound of formula II with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as, for example, pyridine or THF, optionally in the presence of a base such as, for example, triethylamine, at a temperature of rt-180 °C to afford the active species IV (wherein G is G 1 or G 2 ). Additionally, as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt. Chemie 1998, 340, 581, the acid of formula II can be activated by reaction with a coupling reagent such as propanephosphonic anhydride (T3P®) or O-(7-aza-1-benzotriazolyl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) to afford a compound of formula IV (wherein G is G 3 and G 4 ). Subsequent reaction with the amine of formula III affords the compound of formula I.

[0113] The compound of formula (II) (wherein R 3 , R 4 , X, Y, Z are as defined for formula (I)) is prepared by reaction of a compound of formula (V) (wherein R 3 , R 4, X, Y, and Z are as defined for formula (I), and R 20 is 1 ~C 6 alkyl) can be obtained by conversion. This is shown in Scheme 2 below. Scheme 2

Chemical Structure

[0114] As shown in Scheme 2, compound (V) can be converted to compound (II) via a hydrolysis reaction under basic conditions by a method known to those skilled in the art, for example, the method described in ACS Chemical Neuroscience 2017, 2374. For example, this reaction can be carried out in water, or in an organic solvent such as methanol, THF, or dichloromethane, or in a mixture thereof, in the presence of a base such as lithium hydroxide, sodium hydroxide, or potassium hydroxide. Alternatively, the conversion of compound (V) to compound (II) can be carried out under acidic conditions by a method known to those skilled in the art, for example, the method described in J.Med.Chem.1986, 2363. 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 an acid such as trifluoroacetic acid, hydrochloric acid, or sulfuric acid.

[0115] A compound of formula (Va) (wherein R 3 , X, Y, and Z are as defined for formula (I), and R 20 is 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) is a sulfonylating agent of formula (VII) (wherein R 7 is 1 ~C 6 alkyl, C 1 ~C 6 haloalkyl, C 1 ~C 6 cycloalkyl or C 1 ~C 6is a halocycloalkyl, and G is a halogen or an activating group of formula G5) in the presence of a compound of formula (VI) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) can be obtained by conversion. This is shown in Scheme 3 below. Scheme 3

Chemical Structure

[0116] As shown in Scheme 3, the compound (VI) can be converted to the compound (Va) by methods known to those skilled in the art, for example, the methods described in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; International Publication No. 2021153720, International Publication No. 2010150192. For example, this reaction can be carried out in an inert organic solvent such as dichloromethane, 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 is known to those skilled in the art, the compound (VI) in salt form (e.g., hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate) can likewise be used for the conversion to the compound (Va).

[0117] A compound of formula (VI) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) is a compound of formula (VIII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 20 and R 21 are C 1 ~C 6 alkyl, and R23 is hydrogen or methyl), which is shown in Scheme 4 below. Scheme 4 [ka]

[0118] As shown in scheme 4, compound (VIII) can be converted to compound (VI) by methods known to those skilled in the art, for example, methods described in WO 2002059117, J.Med.Chem.2003,5238, Org.Lett.2022,2064. 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 dichloromethane, dioxane or THF. Compound (VI) can also be used in its salt form (e.g., hydrochloride, hydrobromide, trifluoroacetate, paratoluenesulfonate) following conversion.

[0119] A compound of formula (VIII) 3 , X, Y, Z are as defined for formula (I), and R 20 and R 21 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) is reacted with an alkylating agent of formula (Xa), 21 is C 1 ~C 6 and Q is halogen, hydroxyl of a sulfonate group) to prepare a compound of formula (IX) 3 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl), which is shown in Scheme 5 below. Scheme 5 [ka]

[0120] As shown in Scheme 5, compound (IX) can be converted to compound (VIII) by an alkalization reaction with Xa (where Q is a halogen or sulfonate Q1 or Q2) by methods known to those skilled in the art, for example, the methods described in Angew. Chem. Int. Ed. 2017, 12518; WO 2012101244, WO 2004050619, WO 2007072041. For example, this reaction can be carried out in an organic solvent such as dimethylformamide, acetone or acetonitrile in the presence of a base such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compound (IX) can be converted by Mitsunobu reaction with Xa (where Q is equal to OH) by methods known to those skilled in the art, for example, the methods 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 an organic solvent such as toluene or THF in the presence of an azodicarboxylic acid reagent such as diethyl azodicarboxylate or diisopropyl azodicarboxylate and a phosphine reagent such as triphenylphosphine. Alternatively, compound (IX) can be converted to compound (VIII) by an alkylation reaction with aziridine Xb by methods known to those skilled in the art, for example, the methods described in WO 2007070201. For example, this reaction can be carried out in an organic solvent such as acetonitrile in the presence of a base such as potassium carbonate, sodium hydride or sodium carbonate.

[0121] The compound of formula (IX) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl) is an intermediate compound of formula (XI) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is C1 ~C 6 a compound of formula (XII) via (wherein R is alkyl) 3 , X, Y, and Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 22 is halogen) can be obtained in two steps by conversion. This is shown in Scheme 6 below. Scheme 6

Chemical formula

[0122] As shown in Scheme 6, compound (XII) can be converted to compound (XII) by methods known to those skilled in the art having the name of the Miyaura borylation reaction and, for example, the methods described 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 in the presence of a palladium catalyst combined with a suitable ligand such as 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium. Intermediate (XI) can be converted to a compound of formula (IX) by methods known to those skilled in the art, for example, the methods described in Tetrahedron Letters 2014, 2082; Tetrahedron Lett. 2017, 3323; Tetrahedron 2005, 1417. For example, this reaction can be carried out in a mixture of water and an organic solvent such as ethanol, acetonitrile, or dichloromethane in the presence of hydrogen peroxide.

[0123] Alternatively, a compound of formula (VIII) (wherein R 3 , X, Y, and Z are as defined for formula (I), R 20 and R 21 are C 1 ~C 6 alkyl, and R 23is hydrogen or methyl), a compound of formula (Xa) (wherein R 21 is C 1 ~C 6 alkyl, and Q is hydroxy) of a compound of formula (XII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 20 is C 1 ~C 6 alkyl, R 22 is halogen, and R 23 is hydrogen or methyl) can be obtained by conversion. This is shown in Scheme 7 below. Scheme 7

Chemical formula

[0124] As shown in Scheme 7, the compound (XII) can be converted to the compound (VIII) by methods known to those skilled in the art, such as the methods described in Tetrahedron 1988, 91; J. Am. Chem. Soc. 2010, 11592, WO 2020 / 211836. For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. Palladium catalysts and appropriate ligands can be used to promote the reaction as shown in WO 2017 / 147700 and J. Med. Chem. 2021, 11570.

[0125] A compound of formula (Ia) (wherein R 1 , R 2 , R 3 , R 6 , R 7 , X, Y and Z are as defined for formula (I), and R 23 is hydrogen or methyl) is a compound of formula (XIIa) (wherein R 6 is as defined for formula (I), and Q is halogen or sulfonate) of a compound of formula (Ib) (wherein R1 , R 2 , R 3 , R 7 , X, Y and Z are as defined for formula (I), and R 23 (which is hydrogen or methyl) can be obtained by conversion. This is shown in Scheme 8 below. Scheme 8

Chemical formula

[0126] As shown in Scheme 8, compound (Ib) can be converted to compound (Ia) by methods known to those skilled in the art, such as the methods described in ACS Combinatorial Science 2016, 569; International Publication No. 2021 / 15372. For example, this reaction can be carried out in an organic solvent such as dichloromethane, dimethylformamide or acetonitrile in the presence of a base such as potassium carbonate or triethylamine.

[0127] A compound of formula (Id) (wherein R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined for formula (I)) can be obtained by conversion of a compound of formula (Ic) (wherein R 1 , R 2 , R 3 , R 4 , X, Y and Z are as defined for formula (I). This is shown in Scheme 9 below. Scheme 9

Chemical formula

[0128] As shown in Scheme 9, compound (Ic) can be converted into compound (Id) by methods known to those skilled in the art, for example, the methods described in Org. Lett. 2019, 5848; Tetrahedron Lett. 2008, 4579; International Publication No. 2021153720. For example, this reaction can be carried out in an organic solvent such as toluene or chlorobenzene in the presence of a sulfurization reagent such as 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione (Lawesson's reagent).

[0129] Alternatively, the compound of formula (Ic) according to the present invention (wherein R 1 、R 2 、R 3 、R 7 、X, Y, Z are as defined for formula (I), and R 23 is hydrogen or methyl) is a sulfonylating agent of formula (VII) (wherein R 7 is C 1 ~C 6 alkyl, C 1 ~C 6 haloalkyl, C 1 ~C 6 cycloalkyl or C 1 ~C 6 halocycloalkyl, and G is halogen or an activating group of formula G5) in the presence of a compound of formula (XIII) (wherein R 1 、R 2 、R 3 、X, Y and Z are as defined for formula (I), and R 23 is hydrogen or methyl). This can be obtained by the conversion of the following. This is shown in Scheme 9 below. This is shown in Scheme 10 below. Scheme 10

Chemical formula

[0130] As shown in Scheme 10, compound (XIII) can be converted to compound (Ic) by methods known to those skilled in the art, for example, the methods described in Angew. Chem. Int. Ed. 2016, 5299; J. Am. Chem. Soc. 2018, 5322; WO 2021153720; WO 2010150192. For example, this reaction can be carried out in an inert organic solvent such as dichloromethane, 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 is known to those skilled in the art, compound (XIII) in salt form (e.g., hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate) can likewise be used for the conversion to compound (Ic).

[0131] The compound of formula (XIII) wherein R 1 、R 2 、R 3 、X, Y and Z are as defined for formula (I), and R 23 is hydrogen or methyl) can be obtained by conversion of the compound of formula (XIV) wherein R 1 、R 2 、R 3 、X, Y, Z are as defined for formula (I), R 21 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl). This is shown in Scheme 11 below. Scheme 11

Chemical formula

[0132] As shown in Scheme 11, compound (XIV) can be converted to compound (XII) by methods known to those skilled in the art, such as those described in WO 2002 / 059117, J. Med. Chem. 2003, 5238, Org. Lett. 2022, 2064. For example, this reaction can be carried out in an organic solvent such as dichloromethane, dioxane or THF in the presence of an organic or inorganic acid such as hydrochloric acid, trifluoroacetic acid or p-toluenesulfonic acid. Compound (XIII) can also be obtained and used in the following conversion in its salt form (e.g., hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate).

[0133] The compound of formula (XIV) (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I), R 23 is hydrogen or methyl, and R 21 is C 1 ~C 6 alkyl) can be obtained by conversion of the compound of formula (Xa) (wherein R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and Q is halogen, hydroxyl of a sulfonate group) to the compound of formula (XV) (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I)). This is shown in Scheme 12 below. Scheme 12

Chemical Formula

[0134] As shown in Scheme 12, compound (XV) can be converted to compound (XIV) by an alkalization reaction with Xa (when Q is a halogen or sulfonate Q1 or Q2) by methods known to those skilled in the art, for example, the methods described in Angew. Chem. Int. Ed. 2017, 12518; WO 2012 / 101244, WO 2004 / 050619, WO 2007 / 072041. For example, this reaction can be carried out in an organic solvent such as dimethylformamide, acetone or acetonitrile in the presence of a base such as cesium carbonate, sodium hydride or sodium carbonate. Alternatively, compound (XV) can be converted by a Mitsunobu reaction with Xa (when Q is equal to OH) by methods known to those skilled in the art, for example, the methods described in WO 2012 / 074126; Bioorg. Med. Chem. Lett. 1992, 481, Beilstein J. Org. Chem. 2006, 2, 21. For example, this reaction can be carried out in an organic solvent such as toluene or THF in the presence of an azodicarboxylic acid reagent such as diethyl azodicarboxylate or diisopropyl azodicarboxylate and a phosphine reagent such as triphenylphosphine. Alternatively, compound (XV) can be converted to compound (XIV) by an alkylation reaction with aziridine Xb by methods known to those skilled in the art, for example, the methods described in WO 2007 / 070201. For example, this reaction can be carried out in an organic solvent such as acetonitrile in the presence of a base such as potassium carbonate, sodium hydride or sodium carbonate.

[0135] The compound of formula (XV) according to the present invention (wherein R 1 , R 2 , R 3 , X, Y and Z are as defined for formula (I)) is, as described below, a compound of formula (III) via an intermediate acid chloride or activated acylating agent (wherein R 1 and R 2 are as defined for formula (I)) to give a compound of formula (XVI) (wherein R 3, X, Y, and Z can be obtained by the transformation as defined for formula (I), which is shown in Scheme 13 below. Scheme 13

Chemical Formula

[0136] As shown in Scheme 13, compound XVI is activated to a compound of formula XVII by methods known to those skilled in the art, for example, the method described in Tetrahedron 2005, 61(46), 10827 - 10852. For example, a compound of formula XVII (wherein G is halogen) is formed by treating a compound of formula XVI with oxalyl chloride or thionyl chloride in the presence of a catalytic amount of DMF in an inert solvent such as dichloromethane or THF at a temperature of 25 - 170 °C, preferably 25 - 80 °C. Optionally, treatment of XVII with a compound of formula III (wherein R 1 and R 2 are as defined in formula I) in the presence of a base such as triethylamine or pyridine gives a compound of formula I. Alternatively, a compound of formula XV can be prepared by treating a compound of formula XVII with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) which gives a reactive species XVII (wherein G is G 1 or G 2 ) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at a temperature of rt - 180 °C. In addition, as described in, for example, Synthesis 2013, 45, 1569 and J. Prakt. Chemie 1998, 340, 581, the acid of formula XVI is activated by reaction with a coupling reagent such as propanephosphonic anhydride (T3P®) or O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) to give a compound of formula XVII (wherein G is G 3 and G 4It is possible to bring about (). The subsequent reaction with the amine of formula III gives the compound of formula XV.

[0137] A compound of formula (XVI) wherein R 3 , X, Y and Z are as defined for formula (I) can be obtained by conversion of a compound of formula (IX) wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 is C 1 ~C 6 alkyl. This is shown in Scheme 14 below. Scheme 14

Chemical formula

[0138] As shown in Scheme 14, compound (IX) can be converted to compound (XVI) via a hydrolysis reaction under basic conditions by a method known to those skilled in the art, for example, the method described in ACS Chemical Neuroscience 2017, 2374. For example, this reaction can be carried out in water, or in an organic solvent such as methanol, THF or dichloromethane, or in a mixture in the presence of a base such as lithium hydroxide, sodium hydroxide or potassium hydroxide. Alternatively, the conversion of compound (IX) to compound (XVI) can be carried out under acidic conditions by a method known to those skilled in the art, for example, the method described in J.Med.Chem.1986, 2363. 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 an acid such as trifluoroacetic acid, hydrochloric acid or sulfuric acid.

[0139] Alternatively, a compound of formula (XIV) wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I) and R 21 is C 1 ~C6 is alkyl, and R 23 (which is hydrogen or methyl) is a compound of formula (Xa) in which R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and Q is hydroxy) of a compound of formula (XVIII) in which R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen) can be obtained by conversion. This is shown in Scheme 15 below. Scheme 15

Chemical formula

[0140] As shown in Scheme 15, the compound (XVIII) can be converted to the compound (XIV) by methods known to those skilled in the art, such as those described in Tetrahedron 1988, 91; J. Am. Chem. Soc. 2010, 11592, International Publication No. 2020211836. For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. Palladium catalysts and suitable ligands can be used to promote the reaction as shown in International Publication No. 2017147700 and J. Med. Chem. 2021, 11570.

[0141] The compound of formula (XVIII) according to the present invention (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen) is, as described below, a compound of formula (III) via an intermediate acid chloride or activated acylating agent (wherein R 1 and R 2is as defined for formula (I)) a compound of formula (XIX) wherein R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen) can be obtained by conversion. This is shown in Scheme 16 below. Scheme 16

Chemical formula

[0142] As shown in Scheme 16, compound XIX is activated to a compound of formula XX by methods known to those skilled in the art, for example, the method described in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula XX wherein G is halogen is formed by treating a compound of formula II with oxalyl chloride or thionyl chloride at a temperature of 25-170 °C, preferably 25-80 °C, in the presence of a catalytic amount of DMF in an inert solvent such as dichloromethane or THF. Optionally, treatment of XX with a compound of formula III (wherein R 1 and R 2 are as defined in formula I) in the presence of a base such as triethylamine or pyridine gives a compound of formula I. Alternatively, a compound of formula XVIII is treated with active species IV (wherein G is G 1 or G 2It can be prepared by treating a compound of formula XIX with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) which results in (). In addition, as described, for example, in Synthesis 2013, 45, 1569 and J. l Prakt. Chemie 1998, 340, 581, the acid of formula XIX is activated by reaction with a coupling reagent such as propane phosphonic anhydride (T3P (registered trademark)) or O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) to give a compound of formula XX (wherein G is G 3 and G 4 which is). Subsequent reaction with the amine of formula III gives the compound of formula XVIII.

[0143] The compound of formula (XIX) (wherein R 3 , X, Y and Z are as defined for formula (I), and R 22 is halogen) can be obtained by conversion of the compound of formula (XII) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen) in the presence of a base or an acid. This is shown in Scheme 17 below. Scheme 17 [Chemical formula]

[0144] As shown in Scheme 17, compound (XII) can be converted to compound (XIX) via a hydrolysis reaction under basic conditions by a method known to those skilled in the art, for example, the method described in ACS Chem. Neurosci. 2017, 2374. For example, this reaction can be carried out in water, or in an organic solvent such as methanol, THF or dichloromethane, or in a mixture in the presence of a base such as lithium hydroxide, sodium hydroxide or potassium hydroxide. Alternatively, the conversion of compound (XII) to compound (XIX) can be carried out under acidic conditions by a method known to those skilled in the art, for example, the method described in J. Med. Chem. 1986, 2363. 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 an acid such as trifluoroacetic acid, hydrochloric acid or sulfuric acid.

[0145] The compound of formula (XV) (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I)) is obtained in two steps by conversion of the compound of formula (XXI) (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl) via the compound of formula (XVIII) (wherein R 1 , R 2 , R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen). This is shown in Scheme 18 below. Scheme 18

Chemical formula

[0146] As shown in Scheme 18, compound (XVIII) can be converted to compound (XXI) by methods known to those skilled in the art having the name of Miyaura boronylation reaction and, for example, the methods described in WO 2021076728; J. Med. Chem. 2022, 65, 15433. 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 in the presence of a palladium catalyst combined with a suitable ligand such as 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium. Intermediate (XXI) can be converted to a compound of formula (XV) by methods known to those skilled in the art, for example, the methods described in WO 2021127071, Tetrahedron Lett. 2014, 2082; Tetrahedron Lett. 2017, 3323; Tetrahedron 2005, 1417. For example, this reaction can be carried out in a mixture of water and an organic solvent such as ethanol, acetonitrile or dichloromethane in the presence of hydrogen peroxide.

[0147] A compound of formula (Ie) (wherein R 1 , R 2 , R 4 , X, Y, Z are as defined for formula (I), A is oxygen, and R 3 is cyano, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkoxy, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -haloalkoxy) can be obtained by conversion of a compound of formula (If) (wherein R 1 , R 2 , R 4 , X, Y, Z are as defined for formula (I), A is oxygen, and R 3 is halogen). This is shown in Scheme 19 below. Scheme 19

Chemical formula

[0148] As shown in Scheme 19, compound (If) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6 -haloalkyl) by a method known to those skilled in the art, for example, the methods described in J.Med.Chem.2021, J.Am.Chem.Soc.2010, 11592, to obtain compound (Ie) (wherein R 3 is C 1 ~C 6 -alkoxy and C 1 ~C 6 -haloalkoxy). For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. It is possible to promote the reaction using a palladium catalyst and an appropriate ligand. Alternatively, compound (If) can be prepared by a method known to those skilled in the art, for example, the methods described in WO 2021156787, WO 2020210828, Tetrahedron Lett.2000, 41, 6237, from a compound of formula (XXIIb) (wherein R 3 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6- haloalkyl) to obtain compound (Ie). For example, this reaction can be carried out by methods known to those skilled in the art, such as those described in Adv. Synth. Cat. 2017, 359, 2345, US Patent No. 20090062541, Synthesis 2008, 20, 3351, in an organic solvent such as dioxane, THF, dimethylformamide or toluene in the presence of a base such as potassium carbonate or cesium carbonate and in the presence of a palladium catalyst with a suitable ligand such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium. Alternatively, compound (If) can be reacted with a cyanide salt such as potassium ferricyanide, sodium cyanide, potassium cyanide or zinc cyanide to react with compound (Ie) (wherein R 3 is cyano). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, methyl-THF, dimethylformamide, dimethyl sulfoxide or toluene in the presence of an organometallic catalyst such as copper iodide, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, cupric acetate, xantphos Pd G3, optionally in the presence of a ligand such as butylimidazole, N,N'-dimethylethylenediamine, 1-methylimidazole, 1,10-phenanthroline; optionally in the presence of a base such as potassium carbonate, sodium carbonate or cesium carbonate, and optionally in the presence of additives such as polyethylene glycol dodecyl ether and polymethylhydroxysiloxane.

[0149] A compound of formula (Va) wherein R 4 , X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 3 is cyano, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkoxy, C 3 ~C 6 -cycloalkyl, C 1 ~C 6- Haloalkoxy) can be obtained by the conversion of a compound of formula (Vb) (wherein R 4 , X, Y, and Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, and R 3 is halogen). This is shown in Scheme 20 below. Scheme 20

Chemical Structure

[0150] As shown in Scheme 20, the compound (Vb) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6 -haloalkyl) by a method known to those skilled in the art, for example, the methods described in J.Med.Chem.2021, J.Am.Chem.Soc.2010,11592 to obtain a compound (Va) (wherein R 3 is C 1 ~C 6 -alkoxy and C 1 ~C 6 -haloalkoxy). For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. The reaction can be facilitated using a palladium catalyst and an appropriate ligand. Alternatively, the compound (Vb) can be obtained by a method known to those skilled in the art, for example, the methods described in International Publication No. 2021156787, International Publication No. 2020210828, Tetrahedron Letters 2000,41,6237, from a compound of formula (XXIIb) (wherein R 3 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C1 ~C 6 -haloalkyl) to obtain compound (Va). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, dimethylformamide or toluene in the presence of a base such as potassium carbonate or cesium carbonate and in the presence of a palladium catalyst with an appropriate ligand such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium. Alternatively, compound (Vb) can be obtained by reacting with a cyanide salt such as potassium ferricyanide, sodium cyanide, potassium cyanide or zinc cyanide by a method known to those skilled in the art, for example, the methods described in Adv. Synth. Cat. 2017, 359, 2345, U.S. Patent No. 20090062541, Synthesis (2008), (20), 3351, to obtain compound (Va) (wherein R 3 is cyano). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, methyl-THF, dimethylformamide, dimethyl sulfoxide or toluene in the presence of an organometallic catalyst such as copper iodide, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, cupric acetate, Xantphos Pd G3, optionally in the presence of a ligand such as butylimidazole, N,N'-dimethylethylenediamine, 1-methylimidazole, 1,10-phenanthroline, optionally in the presence of a base such as potassium carbonate, sodium carbonate or cesium carbonate, and optionally in the presence of additives such as polyethylene glycol dodecyl ether and polymethylhydroxysiloxane.

[0151] A compound of formula (VIIIa) (wherein X, Y, Z are as defined for formula (I), and R 20 is C 1 ~C 6 alkyl, R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and R 3 is cyano, C 1 ~C 6 -alkyl, C 1~C 6 -alkoxy, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -haloalkoxy) is a compound of formula (VIIIb) (wherein X, Y, Z are as defined for formula (I), R 20 is C 1 ~C 6 alkyl, R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and R 3 is halogen) can be obtained by conversion. This is shown in Scheme 21 below. Scheme 21

Chemical formula

[0152] As shown in Scheme 21, the compound (VIIIb) can be prepared by a method known to those skilled in the art, for example, by the method described in J.Med.Chem. 2021, J.Am.Chem.Soc. 2010, 11592, from a compound of formula (XXIIa) (wherein R 24 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6 -haloalkyl) by reacting it with a compound of formula (VIIIa) (wherein R 3 is C 1 ~C 6 -alkoxy and C 1 ~C 6- haloalkoxy) can be obtained. For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. The reaction can be promoted using a palladium catalyst and an appropriate ligand. Alternatively, compound (VIIIb) can be prepared by a method known to those skilled in the art, such as the methods described in WO 2021156787, WO 2020210828, Tetrahedron Lett. 2000, 41, 6237, to react with a compound of formula (XXIIb) (wherein R 3 is C 1 ~C 6 - alkyl, C 3 ~C 6 - cycloalkyl and C 1 ~C 6 - haloalkyl) to obtain compound (VIIIa). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, dimethylformamide or toluene in the presence of a base such as potassium carbonate or cesium carbonate and in the presence of a palladium catalyst with an appropriate ligand such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium. Alternatively, compound (VIIIb) can be prepared by a method known to those skilled in the art, such as the methods described in Adv. Synth. Cat. 2017, 359, 2345, US 20090062541, Synthesis 2008, (20), 3351, by reacting with a cyanide salt such as potassium ferricyanide, sodium cyanide, potassium cyanide or zinc cyanide to give compound (VIIIa) (wherein R 3(wherein R is cyano) can be obtained. For example, this reaction can be carried out in an organic solvent such as dioxane, THF, methyl-THF, dimethylformamide, dimethyl sulfoxide or toluene in the presence of a metal-organic catalyst such as copper iodide, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, cupric acetate, Xantphos Pd G3, optionally in the presence of a ligand such as butylimidazole, N,N'-dimethylethylenediamine, 1-methylimidazole, 1,10-phenanthroline, optionally in the presence of a base such as potassium carbonate, sodium carbonate or cesium carbonate, and optionally in the presence of additives such as polyethylene glycol dodecyl ether and polymethylhydroxysiloxane.

[0153] A compound of formula (XIVa) wherein R 1 , R 2 , X, Y, Z are as defined for formula (I), R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and R 3 is cyano, C 1 ~C 6 -alkyl, C 1 ~C 6 -alkoxy, C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -haloalkoxy) can be obtained by conversion of a compound of formula (XIVb) wherein R 1 , R 2 , X, Y, Z are as defined for formula (I), R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and R 3 is halogen). This is shown in Scheme 22 below. Scheme 22

Chemical formula

[0154] As shown in Scheme 21, compound (XIVb) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6 -haloalkyl) by a method known to those skilled in the art, for example, the methods described in J.Med.Chem.2021, J.Am.Chem.Soc.2010, 11592, to obtain compound (XIVa) (wherein R 3 is C 1 ~C 6 -alkoxy and C 1 ~C 6 -haloalkoxy). For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide or toluene in the presence of a base such as sodium hydride, potassium carbonate or cesium carbonate. It is possible to promote the reaction using a palladium catalyst and an appropriate ligand. Alternatively, compound (XIVb) can be prepared by a method known to those skilled in the art, for example, the methods described in WO 2021156787, WO 2020210828, Tetrahedron Lett.2000, 41, 6237, from a compound of formula (XXIIb) (wherein R 3 is C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl and C 1 ~C 6-It can react with a haloalkyl) to obtain compound (XIVa). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, dimethylformamide or toluene in the presence of a base such as potassium carbonate or cesium carbonate and in the presence of a palladium catalyst with an appropriate ligand such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium. Alternatively, compound (XIVb) can be obtained by reacting it with a cyanide salt such as potassium ferricyanide, sodium cyanide, potassium cyanide or zinc cyanide by a method known to those skilled in the art, for example, the methods described in Adv. Synth. Cat. 2017, 359, 2345, U.S. Patent No. 20090062541, Synthesis 2008, (20), 3351, to obtain compound (XIVa) (wherein R 3 is cyano). For example, this reaction can be carried out in an organic solvent such as dioxane, THF, methyl-THF, dimethylformamide, dimethyl sulfoxide or toluene in the presence of an organometallic catalyst such as copper iodide, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, cupric acetate, Xantphos Pd G3, optionally in the presence of a ligand such as butylimidazole, N,N'-dimethylethylenediamine, 1-methylimidazole, 1,10-phenanthroline, optionally in the presence of a base such as potassium carbonate, sodium carbonate or cesium carbonate, and optionally in the presence of additives such as polyethylene glycol dodecyl ether and polymethylhydroxysiloxane.

[0155] The compound of formula (XXIII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 21 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) is the compound of formula (Xa) (wherein R 21 is C 1 ~C 6 alkyl, R 23 is hydrogen or methyl, and Q is hydroxy) with the compound of formula (XIX) (wherein R3 , X, Y, and Z are as defined for formula (I), and R 22 (wherein R is halogen) can be obtained by conversion. This is shown in Scheme 23 below. Scheme 23

Chemical Formula

[0156] As shown in Scheme 23, compound (XIX) can be converted to compound (XXIII) by methods known to those skilled in the art, such as the methods described in Tetrahedron 1988, 91; J. Am. Chem. Soc. 2010, 11592, and International Publication No. 2020 / 211836. For example, this reaction can be carried out in an organic solvent such as dioxane, dimethylformamide, dimethyl sulfoxide, or toluene in the presence of a base such as sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide, sodium hydroxide, benzyltrimethylammonium hydroxide, etc. Palladium catalysts and appropriate ligands can be used to promote the reaction as shown in International Publication No. 2017 / 147700 and J. Med. Chem. 2021, 11570.

[0157] Alternatively, a compound of formula (XIV) (wherein R 1 , R 2 , R 3 , X, Y, and Z are as defined for formula (I), R 21 is C 1 ~C 6 alkyl, and R 23 is hydrogen or methyl) can be prepared as described below via an intermediate acid chloride or activated acylating agent with a compound of formula (III) (wherein R 1 and R 2 are as defined for formula (I)) to give a compound of formula (XXIII) (wherein R 3 , X, Y, and Z are as defined for formula (I), and R 21 is C 1 ~C6 is alkyl, and R 23 (wherein R is hydrogen or methyl) can be obtained by conversion. This is shown in Scheme 24 below. Scheme 24 [Chemical formula]

[0158] As shown in Scheme 24, compound (XXIII) is activated to a compound of formula (XXIV) by methods known to those skilled in the art, for example, the method described in Tetrahedron 2005, 61(46), 10827 - 10852. For example, a compound of formula (XXIV) (wherein G is halogen) is in the presence of a catalytic amount of DMF in an inert solvent such as dichloromethane or THF, at a temperature of 25 - 170 °C, preferably 25 - 80 °C, for example, by treatment of the compound of formula (XXIII) with oxalyl chloride or thionyl chloride. Optionally, treatment of (XXIV) with a compound of formula III (wherein R 1 and R 2 are as defined in formula I) in the presence of a base such as triethylamine or pyridine results in a compound of formula (XIV). Alternatively, the compound of formula XIV can be prepared by treatment of the compound of formula XXIII with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) which gives an active species XXIV (wherein G is G 1 or G 2 ) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at a temperature of rt - 180 °C. In addition, as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt. Chem. 1998, 340, 581, the acid of formula XXIII is activated by reaction with a coupling reagent such as propanephosphonic anhydride (T3P®) or O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU) to give a compound of formula XXIV (wherein G is G3 and G 4 It is possible to bring about (). By subsequent reaction with the amine of formula III, a compound of formula XIV is obtained.

[0159] Depending on the procedure or reaction conditions, it is possible to react the reactants 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, alkylamides, alkylenediamides, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples include 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).

[0160] The reactants can be reacted with each other as such, 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, an excess base such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline can also act as a solvent or diluent.

[0161] The reaction is advantageously carried out in a temperature range of from about -80 °C to about +140 °C, preferably from about -30 °C to about +100 °C, and in many cases in the range from ambient temperature to about +80 °C.

[0162] Depending on the reaction conditions suitable for each case and the choice of starting materials, it is possible, for example, in one reaction step, to simply replace one substituent with another substituent according to the present invention, or in the same reaction step, to replace a plurality of substituents with other substituents according to the present invention.

[0163] The salts of the compounds of formula I can be prepared by methods known per se. Thus, for example, the acid addition salts of the compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchange reagent, and the salts with bases are obtained by treatment with a suitable base or a suitable ion exchange reagent.

[0164] The salts of the compounds of formula I can be converted in a conventional manner, for example, by treatment with a suitable basic compound or a suitable ion exchange reagent, into the acid addition salts of the free compound I, and by treatment with a suitable acid or a suitable ion exchange reagent, into the salts with bases.

[0165] The salts of the compounds of formula I can be converted into other salts, acid addition salts, for example other acid addition salts, of the compounds of formula I in a manner known per se by treatment with a suitable metal salt, such as the sodium salt, barium salt or silver salt of an acid, for example the hydrochloride with silver acetate, in a suitable solvent in which the inorganic salt formed, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.

[0166] Depending on the procedure or reaction conditions, the compounds of formula I having salt-forming properties are obtained in free form or in the form of salts.

[0167] The compounds of formula I and, where appropriate, their tautomers may each exist in free form or in salt form, in the form of pure isomers, such as enantiomers and / or diastereomers, for example, depending on the number of asymmetric carbon atoms present in the molecule, their absolute and relative configuration, and / or depending on the configuration of the non-aromatic double bonds present in the molecule, or as a mixture of isomers, such as a racemate, a mixture of diastereomers or a mixture of racemates, in one form of the possible isomers or as a mixture thereof. The present invention relates to the pure isomers and also to all possible mixtures of isomers and is to be understood in this sense both above and below, even if the details of the stereochemistry are not specifically described in each case.

[0168] A mixture of diastereomers or a racemic mixture of the compounds of formula I can be separated in known manner into the pure diastereomers or racemates on the basis of the physicochemical differences between the components, in the free form or in salt form, obtained depending on which starting materials and procedures are chosen, for example by fractional crystallization, distillation and / or chromatography.

[0169] Mixtures of enantiomers, such as racemates, obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, chromatography on a chiral adsorbent, for example high performance liquid chromatography (HPLC) on acetylcellulose using a suitable microorganism, cleavage by a specific immobilized enzyme via the formation of an inclusion compound using, for example, a chiral crown ether with which only one of the enantiomers complexes, or by conversion into diastereomeric salts, for example by reacting the basic end product racemate with an optically active acid, such as camphoric acid, tartaric acid or malic acid or a sulfonic acid, such as camphorsulfonic acid, and separating the thus obtained mixture of diastereomers by fractional crystallization based, for example, on different solubilities, to give a diastereomer from which the desired enantiomer can be liberated by the action of a suitable substance, such as a basic substance.

[0170] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating suitable mixtures of isomers, but also by methods generally known for diastereoselective or enantioselective synthesis, for example by carrying out the method according to the present invention using starting materials having stereochemical properties.

[0171] The N-oxide can be prepared by reacting the compound of formula I with a suitable oxidizing agent, such as H 2 O 2 / urea adduct in the presence of an acid anhydride, such as trifluoroacetic anhydride. Such oxidations are known from the literature, for example, J. Med. Chem., 32(12), 2561-73, 1989 or WO 2000 / 15615.

[0172] If the individual components have different biological activities, it is advantageous to isolate or synthesize the more biologically effective isomers, such as enantiomers or diastereomers, or mixtures of isomers, such as mixtures of enantiomers or diastereomers, respectively.

[0173] The compounds of formula I and, if appropriate, their tautomers can each be obtained in free form or in salt form, if appropriate in the form of hydrates, and / or can contain other solvents, for example solvents used for the crystallization of the compounds present in solid form.

[0174] The compounds of formula (I) according to Tables A1-5 below can be prepared according to the above methods. The following examples are intended to illustrate the invention and show preferred compounds of formula (I) in the form of the compounds of formula (I-1a), (I-2a), (I-3a), (I-4a) and (I-5a).

Chemical formula

[0175]

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Table 1-13

Table 1-14

Table 1-15

Table 1-16

Table 1-17

Table 1-18

Table 1-19

Table 1-20

Table 1-21

Table 1-22

Table 1-23

Table 1-24

Table 1-25

Table 1-26

Table 1-27

Table 1-28

Table 1-29

Table 1-30

Table 1-31

Table 1-32

Table 1-33

Table 1-34

Table 1-35

Table 1-36

Table 1-37

Table 1-38

Table 1-39

Table 1-40

Table 1-41

Table 1-42

Table 1-43

Table 1-44

Table 1-45

Table 1-46

Table 1-47

Table 1-48

Table 1-49

Table 1-50

Table 1-51

Table 1-52

Table 1-53

Table 1-54

Table 1-55

Table 1-56

[0176]

Table 2-1

Table 2-2

Table 2-3

Table 2-4

Table 2-5

Table 2-6

Table 2-7

Table 2-8

Table 2-9

Table 2-10

Table 2-11

Table 2-12

[0177]

Table 3-1

Table 3-2

Table 3-3

Table 3-4

Table 3-5

[0178]

Table 4-1

Table 4-2

Table 4-3

Table 4-4

Table 4-5

Table 4-6

Table 4-7

Table 4-8

Table 4-9

Table 4-10

[0179]

Table 5-1

Table 5-2

[0180] Certain intermediate compounds are also provided, some of which are novel.

[0181] Accordingly, the following are provided herein: A. Compounds of formula (II-1), (II-2), (II-3) and (II-4) wherein R 3 , R 6 and R 7 are as defined in Tables 1-5, respectively).

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0182] The compounds of formula (I) according to the present invention are active ingredients that are prophylactically and / or therapeutically beneficial in the field of pest control even at low application rates, which have a very favorable biocidal spectrum and are well tolerated by warm-blooded animal species, fish and plants. The active ingredients according to the present invention act not only on normal-sensitivity animal pests such as representatives of insects or the order Acarina, but also on all or individual developmental stages of resistant animal pests. The insecticidal or acaricidal activity of the active ingredients according to the present invention may appear directly, i.e., immediately or only after some time has elapsed, for example as the destruction of pests occurring during molting, or indirectly, for example as a reduced egg-laying and / or hatching rate.

[0183] Examples of the above animal pests are as follows: From the order Acarina, for example, From the genera 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 Anoplura, for example, Genus Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; From Coleoptera, for example, Agriotes spp., Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp, Astylus atromaculatus, Ataenius spp, Atomaria linearis, Chaetocnema tibialis, Cerotoma spp, Conoderus spp, Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp, Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp, Maecolaspis spp, Maladera castanea, Megascelis spp, Meligethes aeneus, Melolontha spp., Myochrous armatus, Orycaephilus spp., Otiorhynchus spp., Phyllophaga spp, Phlyctinus spp., Popillia spp)、Psylliodes spp., Rhyssomatus aubtilis, Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Somaticus spp, Sphenophorus spp, Sternechus subsignatus, Tenebrio spp., Tribolium spp. and Trogoderma spp.;. From Diptera, for example, From the genera Aedes spp., Anopheles spp, Antherigona soccata, Bactrocea oleae, Bibio hortulanus, Bradysia spp, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Delia spp, Drosophila melanogaster, Fannia spp., 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.; From the order Hemiptera, for example, Acanthocoris scabrator, Acrosternum spp, Adelphocoris lineolatus, Aleurodes spp., Amblypelta nitida, Bathycoelia thalassina, Blissus spp, Cimex spp., Clavigralla 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, Diuraphis noxia, Dysaphis spp, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Glycaspis brimblecombei, Hyadaphis pseudobrassicae, Hyalopterus spp, Hyperomyzus pallidus, Idioscopus clypealis, Jacobiasca lybica, Laodelphax spp., Lecanium corni, Lepidosaphes spp., Lopaphis erysimi, Lyogenys maidis, Macrosiphum spp., Mahanarva spp, Metcalfa pruinosa, Metopolophium dirhodum, Myndus crudus, Myzus spp)、Neotoxoptera sp, Nephotettix spp., Nilaparvata spp., Nippolachnus piri Mats, Odonaspis ruthae, Oregma lanigera Zehnter, Parabemisia myricae, Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., Peregrinus maidis, Perkinsiella spp, Phorodon humuli, Phylloxera spp, Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Pseudatomoscelis seriatus, Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Quesada gigas, Recilia dorsalis, Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp) Sogatella furcifera, Spissistilus festinus, Tarophagus Proserpina, Toxoptera spp, Trialeurodes spp, Tridiscus sporoboli, Trionymus spp, Trioza erytreae, Unaspis citri, Zygina flammigera, Zyginidia scutellaris;. From Hymenoptera, for example, Acromyrmex, Arge spp, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monommorium pharaonis, Neodiprion spp., Pogonomyrmex spp, Slenopsis invicta, Solenopsis spp. and Vespa spp.; From Isoptera, for example, Coptotermes spp, Corniternes cumulans, Incisitermes spp, Macrotermes spp, Mastotermes spp, Microtermes spp, Reticulitermes spp.; Solenopsis geminate From the order Lepidoptera, for example, Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyresthia spp, Argyrotaenia spp., Autographa spp., Bucculatrix thurberiella, Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Chrysoteuchia topiaria, Clysia ambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Colias lesbia, Cosmophila flava, Crambus spp, Crocidolomia binotalis, Cryptophlebia leucotreta, Cydalima perspectalis, Cydia spp., Diaphania perspectalis, Diatraea spp., Diparopsis castanea, Earias spp)、Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., Epinotia spp, Estigmene acrea, Etiella zinckinella, Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia jaculiferia, Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Herpetogramma spp, Hyphantria cunea, Keiferia lycopersicella, Lasmopalpus lignosellus, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Loxostege bifidalis, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Mythimna spp, Noctua spp, Operophtera spp., Orniodes indica, Ostrinia nubilalis, Pammene spp., Pandemis spp)、Panolis flammea, Papaipema nebris, Pectinophora gossypiela, Perileucoptera coffeella, Pseudaletia unipuncta, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Pseudoplusia spp, Rachiplusia nu, Richia albicosta, Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Sylepta derogate, Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni, Tuta absoluta and Yponomeuta spp.;. From the Mallophaga, for example, Damalinea spp. and Trichodectes spp.; From the Orthoptera, for example, Cockroaches of the genus Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, locusts of the genus Locusta spp., Neocurtilla hexadactyla, cockroaches of the genus Periplaneta spp., Scapteriscus spp. and grasshoppers of the genus Schistocerca spp.; From the order Psocoptera, for example, Liposcelis spp.; From the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; From the order Thysanoptera, for example, Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp, Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp; From the order Thysanura, for example, Lepisma saccharina.

[0184] In a further aspect, the present invention relates to plant parasitic nematodes (endoparasitic, semi-endoparasitic and ectoparasitic nematodes), in particular root-knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other species of the genus Meloidogyne; cyst-forming nematodes, Globodera rostochiensis and other species of the genus Globodera; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other species of the genus Heterodera; seed gall nematodes, species of the genus Anguina; Aphelenchoides species including the stem nematode and the leaf nematode; sting nematodes, Belonolaimus longicaudatus and other species of the genus Belonolaimus; pine wood nematodes, Bursaphelenchus xylophilus and other species of the genus Bursaphelenchus; sedentary ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other species of the genus Ditylenchus; dagger nematodes, Dolichodorus species;Laccoscelium, Heliocotylenchus multicinctus and other species of the genus Helicotylenchus; sheath and sheathoid nematodes, species of the genus Hemicycliophora and species of the genus Hemicriconemoides; species of the genus Hirshmanniella; needle nematodes, species of the genus Hoploaimus; false root-knot nematodes, species of the genus Nacobbus; lance nematodes, Longidorus elongatus and other species of the genus Longidorus; pin nematodes, species of the genus Pratylenchus; Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other species of the genus Pratylenchus; lesion nematodes, Radopholus similis and other species of the genus Radopholus; false ring nematodes, Rotylenchus robustus, Rotylenchus reniformis and other species of the genus Rotylenchus; species of the genus Scutellonema; stubby-root nematodes, Trichodorus primitivus and other species of the genus Trichodorus, species of the genus Paratrichodorus;Damage to plants and parts thereof caused by plant parasitic nematodes such as Heterodera schachtii, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other species of the genus Tylenchorhynchus; Tylenchulus semipenetrans, species of the genus Tylenchulus; Longidorus elongatus, species of the genus Xiphinema; and other plant parasitic nematode species such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp. and Quinisulcius spp. may also be related to a method for preventing such damage.

[0185] The compounds of the present invention may also have activity against mollusks. Examples thereof include, for example, 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); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicelia (H. itala, H. obvia); Helicidae (Helicigona 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.

[0186] The active ingredient according to the invention can be used to control, i.e. inhibit or destroy, pests of the above type occurring in particular in plants, in particular useful plants and ornamental plants in agriculture, horticulture and forestry or in organs such as fruits, flowers, leaves, stems, tubers or roots of such plants, and optionally the plant organs formed at a later point in time remain protected from these pests.

[0187] Suitable target crops are in particular cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beet such as sugar beet or fodder beet; fruits such as apples, pears, plums, peaches, almonds, cherries or soft fruits such as strawberries, raspberries or blackberries, i.e. pomaceous fruits, stone fruits or soft fruits; leguminous crops such as kidney beans, lentils, peas or soybeans; oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil plant, cocoa or groundnut; cucurbitaceous plants such as pumpkins, cucumbers or melons; fibre plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or peppers; plants of the family Lauraceae such as avocado, cinnamon or camphor; and furthermore tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grapes, hops, plants of the family Solanaceae and latex plants.

[0188] In certain embodiments, the compound of formula (I) is capable of controlling mites, scale insects and aphids in crops, trees and plants selected from vegetables (in particular tomatoes and cucurbitaceous plants), citrus fruits, pomaceous fruits, stone fruits, tree nuts, cotton, tropical crops, avocado, ornamental plants, kidney beans, soybeans, strawberries and grapes.

[0189] The compositions and / or methods of the invention can also be used in any ornamental and / or vegetable crops including flowers, shrubs, broad-leaved trees and evergreen trees.

[0190] For example, the present invention relates to the following ornamental species: species of 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., Centaurea spp., Chrysanthemum spp., Cineraria spp. (C. maritime), Coreopsis spp., Crassula coccinea, Cuphea ignea, Dahlia spp., Delphinium spp., Dicentra spectabilis, Dorotheantus spp., Eustoma grandiflorum, Forsythia spp., Fuchsia spp., Geranium gnaphalium, Gerbera spp., Gomphrena globosa, Heliotropium spp., Helianthus spp., Hibiscus spp.) Species of the genus Hortensia (Hortensia spp.), species of the genus Hydrangea (Hydrangea spp.), Hypoestes phyllostachya, species of the genus Impatiens (Impatiens spp.) (Impatiens walleriana), species of the genus Iresines (Iresines spp.), species of the genus Kalanchoe (Kalanchoe spp.), Lantana camara, Lavatera trimestris, Leonotis leonurus, species of the genus Lilium (Lilium spp.), species of the genus Mesembryanthemum (Mesembryanthemum spp.), species of the genus Mimulus (Mimulus spp.), species of the genus Monarda (Monarda spp.), species of the genus Nemesia (Nemesia spp.), species of the genus Tagetes (Tagetes spp.), species of the genus Dianthus (Dianthus spp.) (carnation), species of the genus Canna (Canna spp.), species of the genus Oxalis (Oxalis spp.), species of the genus Bellis (Bellis spp.), species of the genus Pelargonium (Pelargonium spp.) (Pelargonium peltatum, Pelargonium zonale), species of the genus Viola (Viola spp.) (pansy), species of the genus Petunia (Petunia spp.), species of the genus Phlox (Phlox spp.), species of the genus Plecthranthus (Plecthranthus spp.), species of the genus Poinsettia (Poinsettia spp.), species of the genus Parthenocissus (Parthenocissus spp.) (Parthenocissus quinquefolia, Parthenocissus tricuspidata), species of the genus Primula (Primula spp.), species of the genus Ranunculus (Ranunculus spp.), species of the genus Rhododendron (Rhododendron spp.), species of the genus Rosa (Rosa spp.) (rose), species of the genus Rudbeckia (Rudbeckia spp.), species of the genus Saintpaulia (Saintpaulia spp.), species of the genus Salvia (Salvia spp.) It can be used with any of Scaevola aemola, Schizanthus wisetonensis, Sedum spp., Solanum spp., Surfinia spp., Tagetes spp., Nicotinia spp., Verbena spp., Zinnia spp. and other flower bed plants.

[0191] For example, the present invention relates to the following vegetable species: species of the genus Allium (Allium spp.) (garlic (A. sativum), onion (A. cepa), shallot (A. oschaninii), leek (A. Porrum), scallion (A. ascalonicum), Japanese bunching onion (A. fistulosum)), chervil (Anthriscus cerefolium), celery (Apium graveolus), asparagus (Asparagus officinalis), beet (Beta vulgarus), species of the genus Brassica (Brassica spp.) (cabbage (B. Oleracea), Chinese cabbage (B. Pekinensis), turnip (B. rapa)), pepper (Capsicum annuum), chickpea (Cicer arietinum), endive (Cichorium endivia), species of the genus Cichorium (Cichorium spp.) (chicory (C. intybus), endive (C. endivia)), watermelon (Citrillus lanatus), species of the genus Cucumis (Cucumis spp.) (cucumber (C. sativus), melon (C. melo)), species of the genus Cucurbita (Cucurbita spp.) (summer squash (C. pepo), pumpkin (C. maxima)), species of the genus Cyanara (Cyanara spp.) (artichoke (C. scolymus), cardoon (C. cardunculus)), carrot (Daucus carota), fennel (Foeniculum vulgare), species of the genus Hypericum, lettuce (Lactuca sativa), species of the genus Lycopersicon (Lycopersicon spp.) (tomato (L. esculentum), tomato (L. lycopersicum)), species of the genus Mentha, basil (Ocimum basilicum), parsley (Petroselinum crispum), species of the genus Phaseolus (Phaseolus spp.) (kidney bean (P. vulgaris), red bean (P.Any of coccineus), pea (Pisum sativum), radish (Raphanus sativus), rhubarb (Rheum rhaponticum), species of Rosmarinus, species of Salvia, Spanish salsify (Scorzonera hispanica), eggplant (Solanum melongena), spinach (Spinacea oleracea), species of Valerianella (V. locusta, V. eriocarpa) and broad bean (Vicia faba) may be used.

[0192] Preferred ornamental species include Saintpaulia, begonia, dahlia, gerbera, hydrangea, kalmia, Rosa, Kalanchoe, poinsettia, aster, Centaurea, Coreopsis, Delphinium, Monarda, Phlox, Rudbeckia, Sedum, petunia, Viola, morning glory, geranium, Chrysanthemum, Ranunculus, fuchsia, Salvia, Hydrangea macrophylla, rosemary, sage, Galium odoratum, mint, Capsicum annuum, tomato and cucumber.

[0193] The compounds of formula (I) are effective against mites, ticks and false mites, such as species of the genus Acarapis (Acarapis spp); Acarapis woodi; Acarus siro; species of the genus Acarus (Acarus spp); Aceria sheldoni; Aculops pelekassi; species of the genus Aculops (Aculops spp); Aculus schlechtendali; species of the genus Aculus (Aculus spp); Amblyseius fallacis; species of the genus Brevipalpus (Brevipalpus spp); Brevipalpus phoenicis; Bryobia praetiosa; Bryobia rubrioculus; species of the genus Caloglyphus (Caloglyphus spp); Cheyletiella blakei; species of the genus Cheyletiella (Cheyletiella spp); Cheyletiella yasguri; Chorioptes bovis; species of the genus Chorioptes (Chorioptes spp); species of the genus Cytodites (Cytodites spp); Demodex bovis; Demodex caballi; Demodex canis; Demodex caprae; Demodex equi; Demodex ovis; species of the genus Demodex (Demodex spp.); Demodex suis; Dermanyssus gallinae; species of the genus Dermanyssus (Dermanyssus spp.); species of the genus Eotetranychus (Eotetranychus spp.); Eotetranychus willamettei; Epitrimerus pyri; Eriophyes ribis; species of the genus Eriophyes (Eriophyes spp.); Eriophyes vitis; species of Eutetranychus spp.; Halotydeus destructor; species of Hemitarsonemus spp.; species of Knemidocoptes spp.; species of Laminosioptes spp.; species of Listrophorus spp.; species of Myobia spp.; Neoschongastia xerothermobia; Neotrombicula autumnalis; Neotrombicula desaleri; Notoedres cati; species of Notoedres spp.; Oligonychus coffeae; Oligonychus ilicis; species of Oligonychus spp.; species of Ornithocheyletia spp.; Ornithonyssus bursa; species of Ornithonyssus spp.; Ornithonyssus sylviarum; Otodectes cynotis; species of Otodectes spp.; Panonychus citri; species of Panonychus spp.; Panonychus ulmi; Phyllocoptruta oleivora; species of Phyllocoptruta spp.; species of Phytoseiulus spp.; Pneumonyssoides caninum; Polyphagotarsonemus latus; species of Polyphagotarsonemus spp.); Psorergates ovis; Psorergates spp.; Psoroptes cuniculi; Psoroptes equi; Psoroptes ovis; Psoroptes spp.; Pterolichus spp.; Raillietia spp.; Rhizoglyphus spp.; Sarcoptes bovis; Sarcoptes canis; Sarcoptes caprae; Sarcoptes equi; Sarcoptes ovis; Sarcoptes rupicaprae; Sarcoptes spp.; Sarcoptes 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 may be particularly suitable for the control of.

[0194] In one embodiment, the compound of formula (I) can control 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.

[0195] In a further embodiment, the compound of formula (I) 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.

[0196] The term "crop" should be understood to include crops transformed by the use of recombinant DNA techniques such that they are capable of synthesizing one or more selectively acting toxins, known, for example, from toxins produced by bacteria, in particular bacteria of the genus Bacillus.

[0197] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; or δ-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, insecticidal proteins or vegetative insecticidal proteins (Vip) derived from Bacillus thuringiensis, such as Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc., which are bacterial colony-forming nematodes; toxins produced by animals, such as scorpion toxins, spider-like toxins, bee toxins and other neurotoxins specific to insects; toxins produced by fungi, such as Streptomycetes toxins, plant lectins such as lectins, barley lectin or snowdrop lectin; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0198] Regarding the present invention, δ-endotoxins are understood, for example, as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C or vegetative insecticidal proteins (Vips), such as Vip1, Vip2, Vip3 or Vip3A, and also explicitly as hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are substituted. In such amino acid substitutions, preferably a protease recognition sequence that does not occur naturally is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0199] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0200] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the above publications. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0201] The toxins contained in transgenic plants confer resistance to pests on the plants. Such insects are found in insect taxa, but are particularly commonly found in beetles (Coleoptera), dipterous insects (Diptera) and moths (Lepidoptera).

[0202] Transgenic plants that encode insecticidal resistance and contain one or more genes that express one or more toxins are known, and some of them are commercially available. Examples of such plants are YieldGard® (maize variety expressing the Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing the Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing the Cry9C toxin); Herculex I® (maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to obtain resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing the Cry1Ac toxin); Bollgard I® (cotton variety expressing the Cry1Ac toxin); Bollgard II® (cotton variety expressing the Cry1Ac and Cry2Ab toxins); VipCot® (cotton variety expressing the Vip3A and Cry1Ab toxins); NewLeaf® (potato variety expressing the Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 European corn borer (CB) trait) and Protecta®.

[0203] Further examples of such transgenic crops are as follows: 1. Bt11 maize, manufactured by Syngenta Seeds SAS (Chemin de l’Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96 / 05 / 10. A genetically modified maize that confers resistance to attack by European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also expresses the enzyme PAT recombinantly to obtain resistance to the herbicide glufosinate ammonium.

[0204] 2. Bt176 maize, manufactured by Syngenta Seeds SAS (Chemin de l’Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96 / 05 / 10. A genetically modified maize that confers resistance to attack by European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a Cry1Ab toxin. Bt176 maize also expresses the enzyme PAT recombinantly to obtain resistance to the herbicide glufosinate ammonium.

[0205] 3. MIR604 maize, manufactured by Syngenta Seeds SAS (Chemin de l’Hobit 27, F-31 790 St. Sauveur, France), registration number C / FR / 96 / 05 / 10. A maize made insect-resistant through transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, which has been modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in International Publication No. 03 / 018810.

[0206] 4. MON 863 maize, produced by Monsanto Europe S.A. (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium), registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and has resistance to specific Coleoptera insects.

[0207] 5. IPC 531 cotton, produced by Monsanto Europe S.A. (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium), registration number C / ES / 96 / 02.

[0208] 6. 1507 maize, produced by Pioneer Overseas Corporation (Avenue Tedesco, 7 B-1160 Brussels, Belgium), registration number C / NL / 00 / 10. Genetically modified maize variety for the expression of the protein Cry1F to obtain resistance to specific Lepidoptera insects and the PAT protein to obtain resistance to the herbicide glufosinate ammonium.

[0209] 7. NK603×MON 810 maize, produced by Monsanto Europe S.A. (270-272 Avenue de Tervuren, B-1150 Brussels, Belgium), registration number C / GB / 02 / M3 / 03. Consists of a hybrid maize variety bred by the conventional method of crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize also expresses recombinantly the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, which provides resistance to specific Lepidoptera including the European corn borer, and the protein CP4 EPSPS obtained from the Agrobacterium sp. strain CP4, which confers resistance to the herbicide Roundup® (containing glyphosate).

[0210] Transgenic crops of insect-tolerant plants are also described in BATS (Zentrum fuer Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http: / / bats.ch).

[0211] The term "crop" should be understood to include crops transformed by the use of recombinant DNA technology such that they are able to synthesize, for example, anti-pathogenic substances having a selective action such as so-called "pathogenesis-related proteins" (PRPs, see for example European Patent Application Publication No. 0392225). Examples of such anti-pathogenic substances and transgenic plants capable of synthesizing such anti-pathogenic substances are known, for example, from European Patent Application Publication No. 0392225, International Publication No. 95 / 33818 and European Patent Application Publication No. 0353191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0212] Crops can also be improved to enhance their resistance to fungal (e.g., Fusarium, anthracnose or Phytophthora), bacterial (e.g., Pseudomonas) or viral (e.g., potato leafroll virus, tomato yellow necrosis virus, cucumber mosaic virus) pathogens.

[0213] Crops include those having high resistance to nematodes such as soybean cyst nematodes.

[0214] Crops that are resistant to abiotic stress include, for example, those having high resistance to drought, high salinity, high temperature, low temperature, frost or light by the expression of NF-YB or other proteins known in the art.

[0215] Examples of anti-pathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers such as sodium channel or calcium channel blockers, such as viral KP1, KP4 or KP6 toxins; stilbene synthase; bibenzyl synthase; chitinase; glucanase; so-called "pathogenesis-related proteins" (PRPs; see, for example, European Patent Application Publication No. 0392225); anti-pathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, International Publication No. 95 / 33818) or proteins or polypeptide factors involved in plant pathogen defense (so-called "plant disease resistance genes" described in International Publication No. 03 / 000906).

[0216] A further field of use of the compositions according to the invention is the protection of stored products and storage rooms and of raw materials (such as wood and textiles), floor coverings and buildings and the protection of humans, livestock and productive livestock from pests of the above type, particularly in the field of hygiene.

[0217] 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 endo- or ectoparasites in or on animals. The present invention further provides a compound of the first aspect for use in controlling ectoparasites on animals. The present invention further provides a compound of the first aspect for use in preventing and / or treating diseases caused by infection with ectoparasites.

[0218] The present invention provides the use of a compound of the first aspect for the manufacture of a medicament for controlling endo- or ectoparasites in or on animals. The present invention further provides the use of a compound of the first aspect for the manufacture of a medicament for controlling ectoparasites on animals. The present invention further provides the use of a compound of the first aspect for the manufacture of a medicament for preventing and / or treating diseases caused by infection with ectoparasites.

[0219] The present invention provides the use of a compound of a first aspect in the control of parasites in or on an animal. The present invention further provides the use of a compound of a first aspect in the control of ectoparasites on an animal.

[0220] When used in relation to a parasite in or on an animal, the term "control" refers to a reduction in the number of pests or parasites, the extermination of pests or parasites and / or the prevention of further pest or parasite infestation.

[0221] When used in relation to a parasite in or on an animal, the term "treat" refers to the suppression, delay, arrest or regression of the progression or severity of an existing condition or disease.

[0222] When used in relation to a parasite in or on an animal, the term "prevent" refers to the avoidance of a condition or disease that is developing within the animal.

[0223] When used in relation to a parasite in or on an animal, the term "animal" can refer to mammals and non-mammals such as birds or fish. In the case of mammals, this can be a human or a non-human mammal. Non-human mammals include, but are not limited to, domestic animals and companion animals. Domestic animals include, but are not limited to, cattle, camellids, pigs, sheep, goats and horses. Companion animals include, but are not limited to, dogs, cats and rabbits.

[0224] A "parasite" is a pest that lives within or on a host animal and benefits from nutrients obtained at the expense of the host animal. An "endoparasite" is a parasite that lives inside the host animal. An "ectoparasite" is a parasite that lives on 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, members of the following genera: Rhipicaphalus, e.g., Rhipicaphalus (Boophilus) microplus and Rhipicephalus sanguineus; Amblyomma; Dermacentor; Haemaphysalis; Hyalomma; Ixodes; Rhipicentor; Margaropus; Argas; Otobius; and Ornithodoros. Mites include, but are not limited to, members of the following genera: Chorioptes, e.g., Chorioptes bovis; Psoroptes, e.g., Psoroptes ovis; Cheyletiella; Dermanyssus, e.g., Dermanyssus gallinae; Ornithonyssus; Demodex, e.g., Demodex canis; Sarcoptes, e.g., Sarcoptes scabiei; and Psorergates.Insects include, but are not limited to, members of the following orders: Siphonaptera, Diptera, Mallophaga, Lepidoptera, Coleoptera, and Homoptera. Members of the order Siphonaptera include, but are not limited to, Ctenocephalides felis and Ctenocephatides canis. Members of the order Diptera include, but are not limited to, species of the genus Musca; bot flies, such as Gasterophilus intestinalis and Oestrus ovis; horse flies; deer flies, such as species of the genus Haematopota and species of the genus Tabunus; species of the genus Haematobia, such as Haematobia irritans; species of the genus Stomoxys; species of the genus Lucilia; midges; and mosquitoes. Members of the order Mallophaga include, but are not limited to, blood-sucking lice and biting lice, such as Bovicola ovis and Bovicola bovis.

[0225] When used in relation to a parasite in or on an animal, the term "effective amount" refers to the amount or dosage of a compound of the invention or a salt thereof which, upon single or multiple administrations to the animal, results in the desired effect in or on the animal. The effective amount can be readily determined by the attending diagnostician, as a person skilled in the art, by use of known techniques and by observing the results obtained in similar circumstances. In determining the effective amount, the attending diagnostician will consider a number of factors including, but not limited to, the mammalian species; its size, age and general health; the parasite to be controlled and the extent of the infestation; the particular disease or disorder involved; the degree or complication or severity of the disease or disorder; the response of the solid; the particular compound administered; the mode of administration; the bioavailability characteristics of the preparation administered; the dosage regimen selected; the use of concomitant medications; and other relevant circumstances.

[0226] The compounds of the invention can be administered to an animal by any route having the desired effect, including, but not limited to, topical, oral, parenteral and subcutaneous, with topical administration being preferred. Suitable formulations for topical administration include, for example, solutions, emulsions and suspensions, and can be in the form of pour-on, spot-on, spray-on, spray-race or dip. Alternatively, the compounds of the invention can be administered by ear tag or collar.

[0227] The 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 well known in the art. See, for example, Gould, P.L., “Salt selection for basic drugs”, International Journal of Pharmaceutics, 33:201-217 (1986); Bastin, R.J., et al. “Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities”, Organic Process Research and Development, 4:427-435 (2000); and Berge, S.M., et al., “Pharmaceutical Salts”, Journal of Pharmaceutical Sciences, 66:1-19, (1977). Those skilled in the art of synthesis will understand that the compounds of the present invention can be readily converted to salts, such as hydrochloride salts, and isolated as such using techniques and conditions well known to those skilled in the art. In addition, those skilled in the art of synthesis will understand that the compounds of the present invention can be readily converted from the corresponding salts to the corresponding free bases and isolated as such.

[0228] The present invention may also provide a method for controlling pests (such as mosquitoes and other disease vector animals; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests includes the step of applying the composition of the present invention to a target pest, its habitat, or a surface or substrate by brush application, roller application, spraying, coating, or dipping. As an example, IRS (indoor residual spraying) application to surfaces such as walls, ceilings, or floors is contemplated by the method of the present invention. In another embodiment, it is contemplated that such a composition is applied to a substrate such as a non-woven or fabric material in the form of a net, clothing, bedding, curtains, and tents (or forms that can be used in the manufacture thereof).

[0229] In one embodiment, a method of controlling such pests comprises applying a pesticidally effective amount of the composition of the present invention to a target pest, its habitat, or a surface or substrate so as to impart effective residual pesticidal activity to the surface or substrate. Such application can be effected by brush application, roller application, spraying, coating, or dipping of the pesticidal composition of the present invention. By way of example, IRS application on surfaces such as walls, ceilings or floors is contemplated by the method of the present invention so as to impart effective residual pesticidal activity to the surface. In another embodiment, application of such a composition for residual control of pests on substrates such as textile materials in the form of nets, clothing, bedding, curtains and tents (or forms which can be used in their manufacture) is contemplated.

[0230] Substrates comprising a nonwoven fabric, textile or net to be treated can be made of natural fibers such as cotton, raffia, jute, linen, sisal, hemp or wool or synthetic fibers such as polyamide, polyester, polypropylene, polyacrylonitrile. Polyester is particularly suitable. Methods of fabric treatment 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.

[0231] A further field of use of the composition according to the invention can be the field of trunk injection / trunk treatment of all ornamental trees and of trees bearing any kind of fruit trees and nuts.

[0232] In the field of trunk injection / trunk treatment, the compounds according to the invention can be particularly suitable against the above-mentioned wood-boring insects of the order Lepidoptera and Coleoptera, in particular the woodborers listed in Tables A and B below.

[0233]

Table 6

[0234]

Table 7-1

Table 7-2

[0235] The present invention can be used to control any insect pest that may be present in turf grass, including, for example, beetles, wireworms, termites, ground pearls, chafers, cutworms, mites, crickets, weevils, grain weevils, ticks, billbugs, southern chinch bugs, and earthworms. The present invention can also be used to control insect pests at various stages of the life cycle, including eggs, larvae, nymphs, and adults.

[0236] In particular, the present invention can be used to control insect pests that feed on the roots of turfgrass, including, for example, ground beetles (Cyclocephala spp. (e.g., masked chafer, C. lurida)), Rhizotrogus spp. (e.g., European chafer, R. majalis), Cotinus spp. (e.g., green June beetle, C. nitida), Popillia spp. (e.g., Japanese beetle, P. japonica), Phyllophaga spp. (e.g., May / June beetle), Ataenius spp. (e.g., Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., Asiatic garden beetle, M. castanea), and Tomarus spp., etc.), white grubs (Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana), and leatherjackets (European crane fly, Tipula spp.).

[0237] The present invention can also be used to control insect pests of turfgrass that live in straw, including fall armyworm (Spodoptera frugiperda and common armyworm (such as Pseudaletia unipuncta)), cutworms, white grubs (such as Sphenophorus spp., S. venatus verstitus, and S. parvulus), and sod webworms (such as Crambus spp. and tropical sod webworm, Herpetogramma phaeopteralis).

[0238] The present invention can also be used to control insect pests that inhabit the ground and feed on the leaves of turfgrass, including chinch bugs (such as Blissus insularis), mites of Bermudagrass (Eriophyes cynodoniensis), scale insects of Rhodesgrass (Antonina graminis), two-lined spittlebugs (Propsapia bicincta), aphids, cutworms (Noctuidae), and wheat midge.

[0239] The present invention can also be used to control other pests of turfgrass, such as red imported fire ants (Solenopsis invicta) that create ant mounds in lawns.

[0240] In the field of hygiene, the composition according to the invention can be effective against external parasites such as hard ticks, soft ticks, sarcoptic mites, chiggers, flies (stab flies and licking flies), parasitic fly larvae, lice, bed bugs, fleas and mosquitoes.

[0241] Examples of such parasites are as follows: Among the order Anoplurida, the genera Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp.

[0242] Among the order Mallophagida, the genera Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., and Felicola spp.

[0243] Among Diptera and its suborders 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., 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.

[0244] Among Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

[0245] Among Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

[0246] Among Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattella germanica and Supella spp.

[0247] Among Acaria (Acarida) and 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., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

[0248] Among the mite order Actinedida (Prostigmata) and the tick order Acaridida (Astigmata), for example, the genera Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.

[0249] The composition according to the present invention may also be suitable for protecting materials such as wood, fabric, plastic, adhesive, paste, paint, paper and cardboard, leather, floor finish, and building from insect parasitism.

[0250] The composition according to the present invention can be used, for example, against the following pests: Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinuspecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthesrugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.and beetles such as the lesser grain borer (Dinoderus minutus), and further hymenopteran insects such as the woodwasp (Sirex juvencus), the great spruce sawfly (Urocerus gigas), Urocerus gigas taignus, and Urocerus augur, and termites such as Kalotermes flavicollis, the drywood termite (Cryptotermes brevis), Heterotermes indicola, the eastern subterranean termite (Reticulitermes flavipes), Reticulitermes santonensis, Reticulitermes lucifugus, the giant northern termite (Mastotermes darwiniensis), the Nevada dampwood termite (Zootermopsis nevadensis), and the Formosan subterranean termite (Coptotermes formosanus), and silverfish such as Lepisma saccharina.

[0251] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or salts thereof are particularly suitable for controlling one or more pests selected from the following genera: species of the genus Spodoptera (Spodoptera spp), species of the genus Helicoverpa (Helicoverpa spp), species of the genus Heliothis (Heliothis spp), species of the genus Leucinodes (Leucinodes spp), species of the genus Tuta (Tuta spp), species of the genus Plutella (Plutella spp), species of the genus Cydia (Cydia spp), species of the genus Lobesia (Lobesia spp), species of the genus Tortrix (Tortrix spp), species of the genus Amyelois (Amyelois spp), species of the genus Maruca (Maruca spp), species of the genus Chrysodeixis (Chrysodeixis spp), species of the genus Agrotis (Agrotis spp), species of the genus Elasmopalpus (Elasmopalpus spp), species of the genus Dalbulus (Dalbulus spp), species of the genus Sternechus (Sternechus spp), species of the genus Phyllotreta (Phyllotreta spp), species of the genus Popillia (Popillia spp), species of the genus Scirpophaga (Scirpophaga spp), species of the genus Chilo (Chilo spp), species of the genus Cnaphalocrosis (Cnaphalocrosis spp), species of the genus Tetranychus (Tetranychus spp), species of the genus Panonychus (Panonychus spp), species of the genus Polyphagotarsonemus (Polyphagotarsonemus spp), species of the genus Phyllocoptruta (Phyllocoptruta spp), species of the genus Aculus (Aculus spp), species of the genus Brevipalpus (Brevipalpus spp), species of the genus Oligonychus (Oligonychus spp), species of the genus Aculops (Aculops spp), species of the genus Nilaparvata (Nilaparvata spp), species of the genus Sogatella (Sogatella spp), species of the genus Laodelphax (Laodelphax spp), species of the genus Nephotettix (Nephotettix spp), species of the genus Diabrotica (Diabrotica spp), species of the genus Agriotes (Agriotes spp), species of the genus Hypnoidus (Hypnoidusspecies of Sphenophorus 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.

[0252] In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1-5 and Table P") controls one or more pests selected from the following genera: species of the genus Spodoptera (Spodoptera spp), species of the genus Helicoverpa (Helicoverpa spp), species of the genus Heliothis (Heliothis spp), species of the genus Leucinodes (Leucinodes spp), species of the genus Tuta (Tuta spp), species of the genus Plutella (Plutella spp), species of the genus Cydia (Cydia spp), species of the genus Lobesia (Lobesia spp), species of the genus Tortrix (Tortrix spp), species of the genus Amyelois (Amyelois spp), species of the genus Maruca (Maruca spp), species of the genus Chrysodeixis (Chrysodeixis spp), species of the genus Agrotis (Agrotis spp), species of the genus Elasmopalpus (Elasmopalpus spp), species of the genus Dalbulus (Dalbulus spp), species of the genus Sternechus (Sternechus spp), species of the genus Phyllotreta (Phyllotreta spp), species of the genus Popillia (Popillia spp), species of the genus Scirpophaga (Scirpophaga spp), species of the genus Chilo (Chilo spp), species of the genus Cnaphalocrosis (Cnaphalocrosis spp), species of the genus Tetranychus (Tetranychus spp), species of the genus Panonychus (Panonychus spp), species of the genus Polyphagotarsonemus (Polyphagotarsonemus spp), species of the genus Phyllocoptruta (Phyllocoptruta spp), species of the genus Aculus (Aculus spp), species of the genus Brevipalpus (Brevipalpus spp), species of the genus Oligonychus (Oligonychus spp), species of the genus Aculops (Aculops spp), species of the genus Nilaparvata (Nilaparvata spp), species of the genus Sogatella (Sogatella spp), species of the genus Laodelphax (Laodelphax spp), species of the genus Nephotettix (Nephotettix spp), species of the genus Diabrotica (Diabrotica spp), species of the genus Agriotesspecies of Spodoptera 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.

[0253] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or salts thereof are particularly suitable for controlling one or more pests selected from the following: species of the genus Spodoptera (Spodoptera spp) (e.g., Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Cydia pomonella, species of the genus Lobesia (Lobesia spp), species of the genus Tortrix (Tortrix spp), Maruca vitrata, Chrysodeixis includens, Agrotis ipsilon, Elasmopalpus lignosellus, Dalbulus maidis, species of the genus Phyllotreta (Phyllotreta spp), Popillia japonica, Scirpophaga incertulas, Chilo suppressalis, Cnaphalocrosis medinalis, Tetranychus urticae, Panonychus ulmi, Polyphagotarsonemus latus, Phyllocoptruta oleivora, species of the genus Brevipalpus (Brevipalpus spp), Aculops lycopersici, Nilaparvata lugens, Sogatella frucifera, Laodelphax striatellus, species of the genus Nephotettix (Nephotettix spp), Diabrotica virgiferavigifera), species of the genus Agriotes (Agriotes spp), Hypnoidus bicolor, Limonius canus, Delia radicum, Popillia japonica, Euschistus heros, Piezodorus lituratus, Nezara viridula, Dichelops furcatus, a species of the genus Lygus (Lygus sp.), Leptocorisa acuta, Halyomorpha halys, Thrips tabaci, Scirtothrips dorsalis, Frankliniella occidentalis, Anthonomus grandis, Meligethes aeneus, species of the genus Phyllotreta (Phyllotreta spp), Leptinotarsa decemlineata, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii and Myzus persicae.

[0254] In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 5 and Table P") controls one or more pests selected from the following genera: species of the genus Spodoptera (Spodoptera spp) (e.g., Spodoptera frugiperda, Spodoptera littoralis) + TX, Helicoverpa armigera + TX, Heliothis virescens + TX, Leucinodes orbonalis + TX, Tuta absoluta + TX, Plutella xylostella + TX, Cydia pomonella + TX, species of the genus Lobesia (Lobesia spp) + TX, species of the genus Tortrix (Tortrix spp) + TX, Maruca vitrata + TX, Chrysodeixis includens + TX, Agrotis ipsilon + TX, Elasmopalpus lignosellus + TX, Dalbulus maidis + TX, species of the genus Phyllotreta (Phyllotreta spp) + TX, Popillia japonica + TX, Scirpophaga incertulas + TX, Chilo suppressalis + TX, Cnaphalocrosis medinalis + TX, Tetranychus urticae + TX, Panonychus ulmi + TX, Polyphagotarsonemus latus + TX, Phyllocoptruta oleivora + TX, species of the genus Brevipalpus (Brevipalpus spp) + TX, Aculops lycopersici + TX, Nilaparvata lugens + TX, Sogatellafrucifera)+TX, small brown planthopper (Laodelphax striatellus)+TX, green rice leafhopper species (Nephotettix spp)+TX, western corn rootworm (Diabrotica vigifera)+TX, wireworm species (Agriotes spp)+TX, Hypnoidus bicolor+TX, Limonius canus+TX, cabbage fly (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 bug species (Lygus spp)+TX, slender stink bug (Leptocorisa acuta)+TX, brown marmorated stink bug (Halyomorpha haly)+TX, onion thrips (Thrips tabaci)+TX, citrus thrips (Scirtothrips dorsalis)+TX, western flower thrips (Frankliniella occidentalis)+TX, boll weevil (Anthonomus grandis)+TX, Meligethes aeneus+TX, flea beetle species (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 peach potato aphid (Myzus persicae)+TX.

[0255] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or salts thereof are particularly suitable for controlling the pests listed in the following table in the crops listed.

[0256]

Table 8-1

Table 8-2

Table 8-3

Table 8-4

Table 8-5

Table 8-6

[0257] In a preferred embodiment of each aspect, the compound TX (where the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1-5 and Table P") is a species of Spodoptera spp (e.g., Spodoptera frugiperda, Spodoptera littoralis), Helicoverpa armigera, Heliothis virescens, Leucinodes orbonalis, Tuta absoluta, Plutella xylostella, Cydia pomonella, Lobesia spp, Tortrix sp., Maruca vitrata, Chrysodeixis includens, Agrotis ipsilon, Elasmopalpus lignosellus, Dalbulus maidis, Phyllotreta spp, Popillia japonica, Scirpophaga incertulas, Chilo suppressalis, Cnaphalocrosis medinalis, Nilaparvata lugens, Sogatella frucifera, Laodelphax striatellus, Nephotettix spp, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii and Myzus persicae;Control one or more of the following: species of the genus Spodoptera (Spodoptera spp), such as Spodoptera frugiperda, Spodoptera littoralis + TX, Helicoverpa armigera + TX, Heliothis virescens + TX, Leucinodes orbonalis + TX, Tuta absoluta + TX, Plutella xylostella + TX, Cydia pomonella + TX, species of the genus Lobesia (Lobesia spp) + TX, species of the genus Tortrix (Tortrix spp) + TX, Maruca vitrata + TX, Chrysodeixis includens + TX, Agrotis ipsilon + TX, Elasmopalpus lignosellus + TX, Dalbulus maidis + TX, species of the genus Phyllotreta (Phyllotreta spp) + TX, Popillia japonica + TX, Scirpophaga incertulas + TX, Chilo suppressalis + TX, Cnaphalocrosis medinalis + TX, Nilaparvata lugens + TX, Sogatella frucifera + TX, Laodelphax striatellus + TX, species of the genus Nephotettix (Nephotettix spp) + TX, Bemisia tabaci + TX, Trialeurodes vaporariorum + TX, Aphis gossypii + TX, and Myzus persicae + TX;

[0258] The compounds according to the invention may have any number of beneficial properties, in particular an advantageous level of biological activity for protecting plants against insects or excellent properties for use as agrochemical active ingredients (for example, high biological activity, advantageous activity spectrum, high safety profile (improved physicochemical properties or high biodegradability with respect to non-target organisms above and below ground (such as fish, birds and bees))). In particular, it has surprisingly been found that the compounds of a particular formula (I) can exhibit an advantageous safety profile with respect to non-target arthropods such as pollinators, in particular honey bees, solitary bees and bumble bees. Most specifically, Apis mellifera.

[0259] The compounds according to the invention can be used as pesticidal agents in their undenatured form, but they are generally formulated into compositions using formulation aids such as carriers, solvents and surface-active substances in various ways. The formulations can be in various physical forms, for example, dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oily flowables, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or a water-miscible organic solvent as carrier), in the form of impregnated polymer films or other forms known, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. The dilution can be carried out, for example, with water, liquid fertilizers, trace elements, biological organisms, oils or solvents.

[0260] The complex can be prepared by mixing the active ingredient with a formulation aid, for example, to obtain the composition in the form of a fine solid, granules, solution, dispersion or emulsion. The active ingredient can also be formulated with other adjuvants such as fine solids, mineral oils, vegetable or animal oils, vegetable or animal modified oils, organic solvents, water, surfactants or combinations thereof.

[0261] The active ingredient can also be contained in extremely fine microcapsules. The microcapsules contain the active ingredient in a porous carrier. Thereby, it is possible to release the active ingredient into the environment in a controlled amount (for example, sustained release). The microcapsules usually have a diameter of 0.1 to 500 microns. These contain the active ingredient in an amount of about 25 to 95% by weight based on the capsule weight. The active ingredient can be in the form of a solid mass, fine particles in a solid or liquid dispersion or a suitable solution. The encapsulating membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurethane, polyurea or chemically modified polymers and xanthan gum starch or other polymers known to those skilled in the art. Alternatively, extremely fine microcapsules can be formed by containing the active ingredient in the form of fine particles in a solid matrix of the base, but the microcapsules themselves are not encapsulated.

[0262] The compounding aids suitable for the preparation of the composition according to the present invention are known per se. As the liquid carrier, water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, 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, alkyl pyrrolidone, 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, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityloxide, 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 amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, high molecular weight alcohols such as N-methyl-2-pyrrolidone, etc. may be used.,

[0263] Suitable solid carriers are, for example, talc, titanium dioxide, phyllosilicate clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cotton hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.,

[0264] Most surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. The surfactants can be anionic, cationic, nonionic or polymeric, and these can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates such as diethanolammonium lauryl sulfate; salts of alkylaryl sulfonates such as calcium dodecylbenzene sulfonate; alkylphenol / alkylene oxide adducts such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts such as tridecyl alcohol ethoxylate; soaps such as sodium stearate; salts of alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters; and further substances described, for example, in McCutcheon’s Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).

[0265] Further adjuvants that can be used in pesticidal formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, neutralizing agents or pH adjusters and buffers, corrosion inhibitors, fragrances, wetting agents, uptake enhancers, trace elements, plasticizers, lubricants, lubricants, dispersants, thickeners, antifreezes, bactericides and liquid and solid fertilizers.

[0266] The composition according to the present invention can contain a vegetable oil or an animal oil, a mineral oil, an alkyl ester of such an oil, or an additive containing a mixture of such an oil and an oil derivative. The amount of the oil additive in the composition according to the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added at a desired concentration into the spray tank after the spray mixture is prepared. Preferred oil additives include mineral oil or vegetable oils such as rapeseed oil, olive oil or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils such as methyl derivatives, or animal oils such as fish oil or beef tallow. Preferred oil additives include C 8 ~C 22 alkyl esters of fatty acids, particularly C 12 ~C 18 methyl derivatives of fatty acids, including, for example, methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0267] The composition of the present invention generally contains 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 a formulation aid (which preferably contains 0 to 25% by weight of a surfactant). Commercial products may preferably be formulated as concentrates, but end users will typically utilize diluted formulations.

[0268] The application rate varies within a wide range and depends on the nature of the soil, the application method, the crop plant, the pest to be controlled, the main weather conditions, and other factors depending on the application method, the application time and the target crop. As per general guidelines, the compound can be applied in an amount of 1 to 2000 l / ha, particularly 10 to 1000 l / ha.

[0269] Preferred formulations can have the following composition (by weight). Emulsifiable concentrate: Active ingredient: 1 - 95%, preferably 60 - 90% Surfactant: 1 - 30%, preferably 5 - 20% Liquid carrier: 1 - 80%, preferably 1 - 35%

[0270] Powder: Active ingredient: 0.1 - 10%, preferably 0.1 - 5% Solid carrier: 99.9 - 90%, preferably 99.9 - 99%

[0271] Suspension concentrate: Active ingredient: 5 - 75%, preferably 10 - 50% Water: 94 - 24%, preferably 88 - 30% Surfactant: 1 - 40%, preferably 2 - 30%

[0272] Wettable powder: Active ingredient: 0.5 - 90%, preferably 1 - 80% Surfactant: 0.5 - 20%, preferably 1 - 15% Solid carrier: 5 - 95%, preferably 15 - 90%

[0273] Granule: Active ingredient: 0.1 - 30%, preferably 0.1 - 15% Solid carrier: 99.5 - 70%, preferably 97 - 85%

[0274] The activity of the compositions according to the invention can be considerably broadened by adding other insecticidally, acaricidally and / or fungicidally active ingredients and can be adapted to general circumstances. Mixtures of the compounds of formula (I) with other insecticidally, acaricidally and / or fungicidally active ingredients may also be described in a broader sense as having a synergistic activity and may have further unexpected advantages. For example, better tolerance by plants, reduced phytotoxicity, the fact that insects can be controlled at their different developmental stages or better behavior during their manufacture, for example during grinding or mixing, during their storage or during their use.

[0275] Suitable additives for the active ingredient in this specification are, for example, the following types of active ingredients as typical examples: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acyl ureas, pyridinylmethyleneamino derivatives, macrolides, neonicotinoids, and Bacillus thuringiensis preparations.

[0276] The following mixtures of the compound of formula (I) and the active substance are preferred (the abbreviation "TX" means "one compound selected from the compounds defined in Tables 1 to 5 and Table P"): An adjuvant selected from the group of substances composed of petroleum (alternative name) (628) + TX; Abamectin + TX, Acequinocyl + TX, Acetamiprid + TX, Aceprolol + TX, Acrinathrin + TX, Asinapyril + TX, Aphidipropene + TX, Afoxolaner + TX, Alanicarb + TX, Allethrin + TX, α-Cypermethrin + TX, α-Methrin + TX, Amidoflumet + TX, Aminocarb + TX, Azocyclotin + TX, Bensultap + TX, Benzoximate + TX, Benzpyramoxan + TX, β-Cyfluthrin + TX, β-Cypermethrin + TX, Bifenazate + TX, Bifenthrin + TX, Binapacryl + TX, Bioallethrin + TX, S-Bioallethrin + TX, Bioresthmetrin + TX, Bistrifluron + TX, Broflanilide + TX, Brofluthrinate + TX, Bromophos-ethyl + TX, Buprofezin + TX, Butocarboxim + TX, Kazusaphos + TX, Carbaryl + TX, Carbofuran + TX, Cartap + TX, CAS No.: 1632218-00-8 + TX, CAS No.: 1808115-49-2 + TX, CAS No.: 2032403-97-5 + TX, CAS No.: 2044701-44-0 + TX, CAS No.: 2128706-05-6 + TX, CAS No.: 2095470-94-1 + TX, CAS No.: 2377084-09-6 + TX, CAS No.: 1445683-71-5 + TX, CAS No.: 2408220-94-8 + TX, CAS No.: 2408220-91-5 + TX, CAS No.: 1365070-72-9 + TX, CAS No.: 2171099-09-3 + TX, CAS No.: 2396747-83-2 + TX, CAS No.: 2133042-31-4 + TX, CAS No.: 2133042-44-9 + TX, CAS No.: 1445684-82-1 + TX, CAS No.: 1445684-82-1 + TX, CAS No.: 1922957-45-6 + TX, CAS No.: 1922957-46-7 + TX, CAS No.: 1922957-47-8 + TX, CAS No.: 1922957-48-9 + TX, CAS No.: 2415706-16-8 + TX, CAS No.: 1594624-87-9 + TX, CAS No.: 1594637-65-6 + TX, CAS No.: 1594626-19-3 + TX, CAS No.: 1990457-52-7 + TX, CAS No.: 1990457-55-0 + TX,CAS No.: 1990457-57-2 + TX, CAS No.: 1990457-77-6 + TX, CAS No.: 1990457-66-3 + TX, CAS No.: 1990457-85-6 + TX, CAS No.: 2220132-55-6 + TX, CAS No.: 1255091-74-7 + TX, CAS No.: 2719848-60-7 + TX, CAS No.: 1956329-03-5 + TX, Chlorantraniliprole + TX, Chlordane + TX, Chlorfenapyr + TX, Chlorprothrin + TX, Chromafenozide + TX, Crenpyrin + TX, Cloethocarb + TX, Clothianidin + TX, 2-Chlorophenyl N-methylcarbamate (CPMC) + TX, Cyanofenphos + TX, Cyantraniliprole + TX, Cyclaniliprole + TX, Cyclobutrifluram + TX, Cycloprothrin + TX, Cycloxaprid + TX, Cyenopyrafen + TX, Cyetopyrafen (or Ethopyrafen) + TX, Siflumetofen + TX, Sifluthrin + TX, Cyhalodiamide + TX, Cyhalothrin + TX, Cypermethrin + TX, Cyphenothrin + TX, Cyproflanilide + TX, Thiamethoxam + TX, Deltamethrin + TX, Diafenthiuron + TX, Diazinon + TX, Dibrom + TX, Dichloromethothiaz + TX, Diflufenzopyr + TX, Diflubenzuron + TX, Zimpropyridaz + TX, Dinactin + TX, Dinocap + TX, Dinotefuran + TX, Dioxabenzofos + TX, Emamectin (or Emamectin benzoate) + TX, Empenthrin + TX, ε-Monofluorothrin + TX, ε-Methofluthrin + TX, Esfenvalerate + TX, Ethion + TX, Ethiprole + TX, Etofenprox + TX, Etoxazole + TX, Fanfan + TX, Phenazakine + TX, Fenfluthrin + TX, Fenmezodithiaz + TX, Fenitrothion + TX, Phenobucarb + TX, Phenothiocarb + TX, Phenoxycarb + TX, Fenpropathrin + TX, Fenpyroximate + TX, Fensulphothion + TX, Fenthion + TX, Fentin acetate + TX, Fenvalerate + TX, Fipronil + TX, Flometoquin + TX, Flonicamid + TX, Fluacrypyrim + TX, Fluazaindolizine + TX, Fluazuron + TX, Flubendiamide + TX,Fulbendimine + TX, Flucycloxuron + TX, Flucitrinate + TX, Flucycloxuron + TX, Flucitrinate + TX, Fluensulfone + TX, Flufenoxuron + TX, Flufenprox + TX, Flufiprole + TX, Flufenhexathion + TX, Flumethrin + TX, Fluopyram + TX, Flupentiofenox + TX, Flupirazinofos + TX, Fluopyroxystrobin + TX, Fluopyrimid + TX, Fluralaner + TX, Flubendiamide + TX, Fluxametamide + TX, Phosphazet + TX, γ-Cyhalothrin + TX, Guazatine + TX, Halofenozide + TX, Halfenprox + TX, Heptafluthrin + TX, Hexythiazox + TX, Hydramethylnon + TX, Imicyafos + TX, Imidacloprid + TX, Imiprothrin + TX, Indoxacarb + TX, Iodomethane + TX, Iprodione + TX, Isocycloseram + TX, Isothioate + TX, Ivermectin + TX, κ-Bifenthrin + TX, κ-Tefluthrin + TX, Lambda-Cyhalothrin + TX, Lufenuron + TX, Metaflumizone + TX, Metaflumizone + TX, Methoprene + TX, Methiocarb + TX, Methomyl + TX, Methoxyfenozide + TX, Metofluthrin + TX, Methomyl + TX, Mexacarbate + TX, Milbemectin + TX, Monofluoroacetate + TX, Niclosamide + TX, Niflumuron + TX, Nitenpyram + TX, Nithiazine + TX, Omethoate + TX, Oxamyl + TX, Oxathiazin + TX, Parathion-ethyl + TX, Permethrin + TX, Phenothrin + TX, Phosphocarb + TX, Piperonyl butoxide + TX, Pyrimicarb + TX, Pyrimiphos-ethyl + TX, Pyrimiphos-methyl + TX, Baculovirus + TX, Prallethrin + TX, Profenofos + TX, Profluthrin + TX, Propargite + TX, Propaphos + TX Propoxur + TX, Profenofos + TX, Protrifenbute + TX, Piflubumide + TX, Pymetrozine + TX, Pirimiphos-methyl + TX, Pyrafluprole + TX, Pyridaben + TX, Pyridalyl + TX, Pyrifluquinazon + TX, Pyriproxyfen + TX, Resmethrin + TX, Sallornel + TX, Selamectin + TX, Silfluofen + TX, Spinetoram + TX, Spinosad + TX, Spirodiclofen + TX, Spirotetramat + TX, Spidoxamat + TX, Sulfoxaflor + TX, Tebufenozide + TX, Tebufenpyrad + TX, Tebupirimfos + TX, Tefluthrin + TX, Temephos + TX, Tetrachlorantraniliprole + TX, Tetradifon + TX, Tetramethrin + TX, Tetramethylfluthrin + TX, Tetranactin + TX, Tetraniliprole + TX, theta-Cypermethrin + TX, Thiacloprid + TX, Thiamethoxam + TX, Thiosyclam + TX, Thiodicarb + TX, Thiofanox + TX, Thimet + TX, Thiosultap + TX, Tefluthrin + TX, Thiorantraniliprole + TX, Thiazaflufen + TX, Tolfenpyrad + TX, Toxaphene + TX, Tralomethrin + TX, Transfluthrin + TX, Triazamate + TX, Triazophos + TX, Trichlorfon + TX, Trichloronate + TX, Trichlorfon + TX, Trifluenflonate + TX, Triflumizole + TX, Triclopyrazoflor + TX, Zeta-Cypermethrin + TX, Seaweed extract and fermentation product derived from molasses + TX, Seaweed extract and fermentation product derived from molasses containing urea + TX, Amino acid + TX, Potassium and molybdenum and EDTA-chelated manganese + TX, Seaweed extract and fermented plant product + TX, Seaweed extract and fermented plant product containing plant hormone + TX, Vitamin + TX, EDTA-chelated copper + TX, Zinc + TX and iron + TX, Azadirachtin + TX, Bacillus aizawai + TX, Bacillus chitinosporus AQ746 (NRRL accession number B-21618) + TX, Bacillus firmus + TXFirmus)+TX, Bacillus kurstaki)+TX, Bacillus mycoides AQ726 (NRRL accession number B-21664)+TX, Bacillus pumilus (NRRL accession number B-30087)+TX, Bacillus pumilus AQ717 (NRRL accession number B-21662)+TX, Bacillus sp. AQ178 (ATCC accession number 53522)+TX, Bacillus sp. AQ175 (ATCC accession number 55608)+TX, Bacillus sp. AQ177 (ATCC accession number 55609)+TX, Bacillus subtilis unspecified+TX, Bacillus subtilis AQ153 (ATCC accession number 55614)+TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421)+TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455)+TX, Bacillus subtilis AQ713 (NRRL accession number B-21661)+TX, Bacillus subtilis AQ743 (NRRL accession number B-21665)+TX, Bacillus thuringiensis AQ52 (NRRL accession number B-21619)+TX, Bacillus thuringiensis BD#32 (NRRL accession number B-21530)+TX, Bacillus thuringiensis subspecies kurstaki BMP 123+TX, Beauveria bassiana+TX, D-limonene+TX, granulovirus+TX, harpin+TX, Helicoverpa armigera nuclear polyhedrosis virus+TX, Helicoverpazea) Nuclear polyhedrosis virus + TX, Heliothis virescens nuclear polyhedrosis virus + TX, Heliothis punctigera nuclear polyhedrosis virus + TX, Metarhizium spp. + TX, Muscodor albus 620 (NRRL accession number 30547) + TX, Muscodor roseus A3-5 (NRRL accession number 30548) + TX, Neem tree-based products + TX, Paecilomyces fumosoroseus + TX, Paecilomyces lilacinus + TX, Pasteuria nishizawae + TX, Pasteuria penetrans + TX, Pasteuria ramosa + TX, Pasteuria thornei + TX, Pasteuria usgae + TX, P-cymene + TX, Plutella xylostella granulosis virus + TX, Plutella xylostella nuclear polyhedrosis virus + TX, Polyhedrosis virus + TX, Artemisia princeps + TX, QRD 420 (terpenoid blend) + TX, QRD 452 (terpenoid blend) + TX, QRD 460 (terpenoid blend) + TX, Quillaja saponaria + TX, Rhodococcus globerulus AQ719 (NRRL accession number B-21663) + TX, Spodoptera frugiperda nuclear polyhedrosis virus + TX, Streptomyces galbus (NRRL accession number 30232) + TX, Streptomyces sp. (NRRL accession number B-30145) + TX, Terpenoid blend + TX and Verticillium spp. + TX An algicide selected from the group of substances consisting of [[CCN]]+TX of vetoxazine, copper dioctanoate (IUPAC name)(170)+TX, copper sulfate(172)+TX, [[CCN]]+TX of sibutrine, [[CCN]]+TX of dichloron(1052), [[CCN]]+TX of dichlorophene(232), [[CCN]]+TX of endothal(295), [[CCN]]+TX of fentin(347), [[CCN]]+TX of slaked lime, [[CCN]]+TX of nerbum(566), [[CCN]]+TX of quinoclamine(714), [[CCN]]+TX of quinonamide(1379), [[CCN]]+TX of simazine(730), triphenyltin acetate (IUPAC name)(347) and triphenyltin hydroxide (IUPAC name)(347)+TX; An anthelmintic selected from the group of substances consisting of [[CCN]]+TX of abamectin(1), [[CCN]]+TX of curfomate(1011), [[CCN]]+TX of cyclobutrifluram, [[CCN]]+TX of doramectin (alternative name), [[CCN]]+TX of emamectin(291), [[CCN]]+TX of emamectin benzoate(291), [[CCN]]+TX of eprinomectin (alternative name), [[CCN]]+TX of ivermectin (alternative name), [[CCN]]+TX of milbemycin oxime (alternative name), [[CCN]]+TX of moxidectin (alternative name), [[CCN]]+TX of piperazine, [[CCN]]+TX of selamectin (alternative name), [[CCN]]+TX of spinosad(737) and [[CCN]]+TX of thiophanate(1435); A bird repellent selected from the group of substances consisting of [[CCN]]+TX of chloralose(127), [[CCN]]+TX of endrin(1122), [[CCN]]+TX of fenthion(346), [[CCN]]+TX of pyridin-4-amine (IUPAC name)(23) and [[CCN]]+TX of strychnine(745); A bactericide selected from the group of substances 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], dichlorophen (232) + TX, dipyrithione (1105) + TX, dodine (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, hydralgofen (alternative name) [CCN], 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, tecnazene (766) + TX and thimerosal (alternative name) [CCN]; Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Berliner (scientific name) (51) + TX, Bacillus thuringiensis subsp. aizawai (scientific name) (51) + TX, Bacillus thuringiensis subsp. israelensis (scientific name) (51) + TX, Bacillus thuringiensis subsp. japonensis (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)(alternative name)(53)+TX, Beauveria brongniartii)(alternative name)(54)+TX, Chrysoperla carnea)(alternative name)(151)+TX, Cryptolaemus montrouzieri)(alternative name)(178)+TX, Cydia pomonella GV)(alternative name)(191)+TX, Dacnusa sibirica)(alternative name)(212)+TX, Diglyphus isaea)(alternative name)(254)+TX, Encarsia formosa)(scientific name)(293)+TX, Eretmocerus eremicus)(alternative name)(300)+TX, Helicoverpa zea NPV)(alternative name)(431)+TX, Heterorhabditis bacteriophora and H. megidis)(alternative name)(433)+TX, Hippodamia convergens)(alternative name)(442)+TX, Leptomastix dactylopii)(alternative name)(488)+TX, Macrolophus caliginosus)(alternative name)(491)+TX, Mamestra brassicae NPV)(alternative name)(494)+TX, Metaphycus helvolus)(alternative name)(522)+TX, Metarhizium anisopliae var. acridum)(scientific name)(523)+TX, Metarhizium anisopliae var. anisopliae)(scientific name)(523)+TX, Neodiprion sertifer NPV and N. reconti(N.Biological agents selected from the group of substances consisting of: [[ID=]], NPV (alternate name) (575) + TX, Orius spp. (alternate name) (596) + TX, Paecilomyces fumosoroseus (alternate name) (613) + TX, Phytoseiulus persimilis (alternate name) (644) + TX, Spodoptera exigua multiple capsid nuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alternate name) (742) + TX, Steinernema carpocapsae (alternate name) (742) + TX, Steinernema feltiae (alternate name) (742) + TX, Steinernema glaseri (alternate name) (742) + TX, Steinernema riobrave (alternate name) (742) + TX, Steinernema riobravis (alternate name) (742) + TX, Steinernema scapterisci (alternate name) (742) + TX, Steinernema spp. (alternate name) (742) + TX, Trichogramma spp. (alternate name) (826) + TX, Typhlodromus occidentalis (alternate name) (844) and Verticillium lecanii (alternate name) (848) + TX; Soil sterilizing agents selected from the group of substances consisting of: [[ID=]], iodomethane (IUPAC name) (542) and methyl bromide (537) + TX; A sterilizing agent selected from the group of substances consisting of apholate [CCN]+TX, bisazir (alternative name) [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron (250)+TX, dimatiph (alternative name) [CCN]+TX, hemeral [CCN]+TX, hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl apholate [CCN]+TX, moldid [CCN]+TX, penfluron (alternative name) [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name) [CCN]+TX, thiotepa (alternative name) [CCN]+TX, trethamine (alternative name) [CCN] and uredepa (alternative name) [CCN]+TX; (E)-Dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name) (829)+TX, (E)-6-methylhepta-2-en-4-ol (IUPAC name) (541)+TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX, (Z)-hexadeca-11-enal (IUPAC name) (436)+TX, (Z)-hexadeca-11-en-1-yl acetate (IUPAC name) (437)+TX, (Z)-hexadeca-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX, (Z)-icosa-13-en-10-one (IUPAC name) (448)+TX, (Z)-tetradec-7-en-1-ol (IUPAC name) (782)+TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX, (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate (IUPAC name) (283)+TX, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX, (9Z,12E)-tetradeca-9,12-Dien-1-yl acetate (IUPAC name) (781) + TX, 14-Methyloctadec-1-ene (IUPAC name) (545) + TX, 4-Methylnonan-5-ol and 4-Methylnonan-5-one (IUPAC name) (544) + TX, α-Multistriatin (alternate name) [CCN] + TX, Brevicomin (alternate name) [CCN] + TX, Codrelure (alternate name) [CCN] + TX, Codreemon (alternate name) (167) + TX, Cuelure (alternate name) (179) + TX, Disparlure (277) + TX, Dodeca-8-en-1-yl acetate (IUPAC name) (286) + TX, Dodeca-9-en-1-yl acetate (IUPAC name) (287) + TX, Dodeca-8 + TX, 10-Dien-1-yl acetate (IUPAC name) (284) + TX, Dominicalure (alternate name) [CCN] + TX, Ethyl 4-Methyloctanoate (IUPAC name) (317) + TX, Eugenol (alternate name) [CCN] + TX, Frontalin (alternate name) [CCN] + TX, Gossyplure (registered trademark) (alternate name; 1:1 mixture of (Z,E) and (Z,Z) isomers of hexadeca-7,11-dien-1-yl-acetate) (420) + TX, Grandlure (421) + TX, Grandlure I (alternate name) (421) + TX, Grandlure II (alternate name) (421) + TX, Grandlure III (alternate name) (421) + TX, Grandlure IV (alternate name) (421) + TX, Hexalure [CCN] + TX, Ipsdienol (alternate name) [CCN] + TX, Ipsenol (alternate name) [CCN] + TX, Japonilure (alternate name) (481) + TX, Linalool (alternate name) [CCN] + TX, Litlure (alternate name) [CCN] + TX, Lureple (alternate name) [CCN] + TX, Medlure [CCN] + TX, Megatomonic acid (alternate name) [CCN] + TX, Methyl Eugenol (alternate name) (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, orfralal (alternative name) [CCN] + TX, orictalal (alternative name) (317) + TX, ostramon (alternative name) [CCN] + TX, siglual [CCN] + TX, soldigin (alternative name) (736) + TX, sulcatol (alternative name) [CCN] + TX, tetradeca-11-en-1-yl acetate (IUPAC name) (785) + TX, trimedolal (839) + TX, trimedolal A (alternative name) (839) + TX, trimedolal B, 1 (alternative name) (839) + TX, trimedolal B 2 An insect pheromone selected from the group of substances consisting of trimedolal C (alternative name) (839) + TX, trimedolal C (alternative name) (839) and trunc-call (alternative name) [CCN] + TX, An insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, diethyltoluamide [CCN] + TX, dimethylcarbamate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethylhexanediol (1137) + TX, hexaamide [CCN] + TX, methoquine-butyl (1276) + TX, methyl neodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, A molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide [CCN]+TX, calcium arsenite [CCN]+TX, cloethocarb (999)+TX, copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaaldehyde (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX, niclosamide - allamine (576)+TX, pentachlorophenol (623)+TX, sodium pentachlorophenoxide (623)+TX, thiazinamcarb (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913)+TX, triphenylmor (1454)+TX, trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole [394730 - 71 - 3]+TX, AKD-3088 (Compound Code) + TX, 1,2-dibromo-3-chloropropane (IUPAC / Chemical Abstracts Name) (1045) + TX, 1,2-dichloropropane (IUPAC / Chemical Abstracts Name) (1062) + TX, 1,2-dichloropropane and 1,3-dichloropropene (IUPAC Name) (1063) + TX, 1,3-dichloropropene (233) + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide (IUPAC / Chemical Abstracts Name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC Name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC Name) (1286) + TX, 6-isopentenylaminopurine (Alternative Name) (210) + TX, abamectin (1) + TX, acetoprole [CCN] + TX, alanycarb (15) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, AZ60541 (Compound Code) + TX, Benclothiaz [CCN] + TX, Benomyl (62) + TX, Butylpyridaben (Alternative Name) + TX, Kazusa Phosphorus (109) + TX, Carbofuran (118) + TX, Carbon Disulfide (945) + TX, Carbosulfan (119) + TX, Chloropicrin (141) + TX, Chlorpyrifos (145) + TX, Cloethocarb (999) + TX, Cyclobutrifluram + TX, Cytokinin (Alternative Name) (210) + TX, Dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, Diamidafos (1044) + TX, Diclofenthion (1051) + TX, Dicriphos (Alternative Name) + TX, Dimethoate (262) + TX, Doramectin (Alternative Name) [CCN] + TX, Emamectin (291) + TX, Emamectin Benzoate (291) + TX, Eprinomectin (Alternative Name) [CCN] + TX, Ethoprophos (312) + TX, Ethylene Dibromide (316) + TX, Fenamiphos (326) + TX, Fenpyralid (Alternative Name) + TX, Fensulfothion (1158) + TX, Phosphothiazate (408) + TX, Phosphothioethane (1196) + TX, Furfural (Alternative Name) [CCN] + TX, GY-81 (Development Code) (423) + TX, Heterophos [CCN] + TX, Iodomethane (IUPAC Name) (542) + TX, Isamidafos (1230) + TX, Isazophos (1231) + TX, Ivermectin (Alternative Name) [CCN] + TX, Kinetin (Alternative Name) (210) + TX, Mekarfos (1258) + TX, Metam (519) + TX, Metam-Potassium (Alternative Name) (519) + TX, Metam-Sodium (519) + TX, Methyl Bromide (537) + TX, Methyl Isothiocyanate (543) + TX, Milbemycin Oxime (Alternative Name) [CCN] + TX, Moxidectin (Alternative Name) [CCN] + TX, Myrotheciumnematicides selected from the group consisting of compositions (alternate names) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphocarb [CCN] + TX, cebufos (alternate name) + TX, selamectin (alternate name) [CCN] + TX, spinosad (737) + TX, terbum (alternate name) + TX, terbufos (773) + TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422) + TX, thiafenox (alternate name) + TX, thionazin (1434) + TX, triazophos (820) + TX, triazolone (alternate name) + TX, xylenol [CCN] + TX, YI-5302 (compound code) and zeatin (alternate name) (210) + TX, fluensulfone [318290-98-1] + TX, fluopyram + TX, nitrification inhibitors selected from the group consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX, plant activators selected from the group consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Japanese knotweed (Reynoutria sachalinensis) extract (alternate name) (720) + TX, Rodenticides selected from the group of substances consisting of 2-isovalerylindane-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, anto (antu) (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (including alpha-bromadiolone) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, colecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, coumafuryl (1005) + TX, coumatetralyl (175) + TX, crimidine (1009) + TX, diphacinone (246) + TX, diphthialone (249) + TX, difacinone (273) + TX, ergocalciferol (301) + TX, flocoumafen (357) + TX, fluoroacetamide (379) + TX, flupropadine (1183) + TX, flupropadine 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, phosacetim (1336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, pindone (1341) + TX, potassium arsenite [CCN] + TX, pirinuron (1371) + TX, silymarin (1390) + TX, sodium arsenite [CCN] + TX, sodium cyanide (444) + TX, sodium fluoroacetate (735) + TX, strychnine (745) + TX, thallium sulfate [CCN] + TX, warfarin (851) and zinc phosphide (640) + TX, Synergist selected from the group of substances 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 (alternative name) (324)+TX, MB-599 (development code) (498)+TX, MGK 264 (development code) (296)+TX, piperonyl butoxide (649)+TX, piprotal (1343)+TX, propyl isomer (1358)+TX, S421 (development code) (724)+TX, sesamex (1393)+TX, sesamolin (1394) and sulfoxide (1406)+TX, Animal repellent selected from the group of substances consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine (422)+TX, guazatine acetate (422)+TX, methiocarb (530)+TX, pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX, trimethacarb (840)+TX, zinc naphthenate [CCN] and dithiram (856)+TX, Virus-killing agent selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN]+TX, Wound protector selected from the group of substances consisting of mercuric oxide (512)+TX, octylinone (590) and thiophanate-methyl (802)+TX, 1,1-Bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-Dichlorophenylbenzenesulfonate + TX, 2-Fluoro-N-methyl-N-1-cinnamaldehyde + TX, 4-Chlorophenylphenylsulfone + TX, Aceprol + TX, Aldoxycarb + TX, Amidithion + TX, Amidithioate + TX, Amiton + TX, Amiton hydrogen oxalate + TX, Amitraz + TX, Aramite + TX, Arsenic trioxide + TX, Azobenzene + TX, Azothoate + TX, Benomyl + TX, Benoxaphos + TX, Benzyl benzoate + TX, Bixafen + TX, Bromopropylate + TX, Bromocyclene + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium polysulfide + TX, Camphechlor + TX, Carbaryl + TX, Carbophenothion + TX, Cimiazole + TX, Chinomethionat + TX, Chlorobenzilate + TX, Chlordimeform + TX, Chlordimeform hydrochloride + TX, Chlorophenethol + TX, Chlorfenethol + TX, Chlorphenesulfide + TX, Chlorobenzilate + TX, Chloromethiuron + TX, Chloropropylate + TX, Chlorothiophos + TX, Cineole I + TX, Cineole II + TX, Cineole S + TX, Cloethocarb + TX, Coumaphos + TX, Chlorotoluron + TX, Crotoxyphos + TX, Cufraeb + TX, Cyanthoate + TX, DCPM + TX, DDT + TX, Demephion + TX, Demephion - O + TX, Demephion - 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, Diclovos + TX, Dienochlor + TX, Dimethoate + TX, Dinex + TX, Dinex dicrexine + TX, Dinocap - 4 + TX, Dinocap - 6 + TX, Dinocap + TX, Dinopentate + TX, Dinoseb + TX, Dinoterbon + TX, Dioxathion + TX, Diphenyl sulfone + TX, Disulfiram + TX, DNOC + TX, Dofenapyn + TX, Doramectin + TX, Endothion + TX,Epirinomectin + TX, Ethoate methyl + TX, Ethirimol + TX, Phenazafur + TX, Fenbutatin oxide + TX, Phenothiocarb + TX, Fenpyram + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubendiamide + TX, Flucycloxuron + TX, Fluenechil + TX, Fluorobenzide + TX, FMC 1137 + TX, Formetanate + TX, Formetanate hydrochloride + TX, Formparanate + TX, γ-HCH, Gliotoxin, Halofenprox, Hexadecyl cyclopropanecarboxylate + TX, Isocarbophos, Jasmonin I, Jasmonin II, Iodofenphos, Lindane, Malonoben, Mecarbam, Methidathion, Mesulfen, Methacrifos, Methyl bromide, Methiocarb, Mexacarbate, Milbemycin oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, Nifluridide, Nikkomycin, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex + TX, Omethoate, Oxydeprofos, Oxydisulfoton, pp’-DDT, Parathion, Permethrin, Phorate, Phosalone, Phosphorothioate, Phosphamidon, Polychloroterpene, Polyactin, Proclonol, Promacyl, Propoxur, Prothidathion, Prothoate, Pyrethrin I, Pyrethrin II, Pyrethrin, Pyridafenthion, Pyrimitate, Quinalphos, Quinthiocarb, R-1492, Phosphoglycine, Rotenone, Shradan, Cephos, Selamectin, Sofamide, SSI-121, Sulfiram, Sulfuramid, Sulfotepp, Sulfur, Diflubenzuron, τ-Fluvalinate, TEPP, Terbumethrin,Tetradifon + TX, Tetrasul + TX, Thiophanox + TX, Thio carboxime + TX, Thiofanox + TX, Thimet + TX, Thiocyclox + TX, Tsurugiensin + TX, Triamiphos + TX, Triarathen + TX, Triazophos + TX, Triazuron + TX, Triphenphos + TX, Trinactin + TX, Bamidothion + TX, Vaniliprole + TX, Vetoxazine + TX, Copper neodecanoate + TX, Copper sulfate + TX, Sibuthrin + TX, Dicloran + TX, Dichlorophen + TX, Endothal + TX, Fentin + TX, Slaked lime + TX, Nabam + TX, Quinoclamine + TX, Quinone amide + TX, Simazine + TX, Triphenyltin acetate + TX, Triphenyltin hydroxide + TX, Curpomethate + TX, Piperazine + TX, Thiophenate + 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, Dodine + TX, Phenaminosulf + TX, Formaldehyde + TX, Hydralgafene + TX, Kasugamycin + TX, Kasugamycin hydrochloride hydrate + TX, Nickel bis(dimethyldithiocarbamate)+TX, Nitrapyrin + TX, Octhilinone + TX, Oxolinic acid + TX, Oxytetracycline + TX, Potassium hydroxyquinoline sulfate + TX, Probenazole + TX, Streptomycin + TX, Streptomycin sesquisulfate + TX, Techlofthalam + TX, Thimerosal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX,Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii + TX, aldicarb + TX, bixazil + TX, busulfan + TX, dimethipin + TX, hemer + TX, hempa + TX, metepa + TX, methiotepa + TX, methyl aldicarb + TX, moldex + 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-Methylhepta-2-en-4-ol + TX, (E,Z)-Tetradeca-4,10-dien-1-yl acetate + TX, (Z)-Dodeca-7-en-1-yl acetate + TX, (Z)-Hexadeca-11-enal + TX, (Z)-Hexadeca-11-en-1-yl acetate + TX, (Z)-Hexadeca-13-en-11-in-1-yl acetate + TX, (Z)-Icosa-13-en-10-one + TX, (Z)-Tetradeca-7-en-1-al + TX, (Z)-Tetradeca-9-en-1-ol + TX, (Z)-Tetradeca-9-en-1-yl acetate + TX, (7E,9Z)-Dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-Tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-Tetradeca-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, Codrelure + TX, Codremon + TX, Querelure + TX, Disparlure + TX, Dodeca-8-en-1-yl acetate + TX, Dodeca-9-en-1-yl acetate + TX, Dodeca-8 + TX, 10-Dien-1-yl acetate + TX, Dominicalure + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grandlure + TX, Grandlure I + TX, Grandlure II + TX, Grandlure III + TX, Grandlure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX, Japonilure + TX, Linaetriene + TX, Litlure + TX, Lurepru + TX, Medlure + TX, Megatomonic acid + TX, Methyl eugenol + TX, Muscalure + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Orfralure + TX, Orictalure + TX, Ostramone + TX, Siglure + TX, Soldiure + TX, Sulcatol + TX, Tetradeca-11-en-1-yl acetate + TX, Trimedlure + TX, Trimedlure A + TX, Trimedlure B 1 + TX, Trimedlure B 2+TX, Triamcinolone C +TX, Truncated call +TX, 2-(Octylthio)-ethanol +TX, Butapironexyll +TX, Butoxy(polypropylene glycol) +TX, Dibutyl adipate +TX, Dibutyl phthalate +TX, Dibutyl succinate +TX, Diethyltoluamide +TX, Dimethyl carbonate +TX, Dimethyl phthalate +TX, Ethylhexanediol +TX, Hexamide +TX, Methoxy-butyl +TX, Methyl neodecanamide +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 methyl phosphate +TX, 2-(1,3-Dithiolan-2-yl)phenyl dimethylcarbamate +TX, 2-(2-Butoxyethoxy)ethyl thiocyanate +TX, 2-(4,5-Dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate +TX, 2-(4-Chloro-3,5-xylyloxy)ethanol +TX, 2-Chlorovinyl diethyl phosphate +TX, 2-Imidazolidone +TX, 2-Isovaleryl indane-1,3-dione +TX, 2-Methyl(prop-2-ynyl)aminophenyl methylcarbamate +TX, 2-Thiocyanatoethyl laurate +TX, 3-Bromo-1-chloroprop-1-ene +TX, 3-Methyl-1-phenylpyrazol-5-yl dimethylcarbamate +TX, 4-Methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate +TX, 5,5-Dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, Acetion + TX, Acrylonitrile + TX, Aldrin + TX, Arasamidine + TX, Alicyclab + TX, α-Ecdysone + TX, Aluminum phosphide + TX, Aminocarb + TX, Anabasine + TX, Achidathion + TX, Azamethiphos + TX, Bacillus thuringiensis δ-endotoxin + TX, Barium hexafluorosilicate + TX, Barium polysulfide + TX, Bartrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-Cyfluthrin + TX, β-Cyphenothrin + TX, Bioethomethrin + TX, Biopermethrin + TX, Bis(2-chloroethyl) ether + TX, Sodium borate + TX, Bromfenvinfos + TX, Bromo-DDT + TX, Buphencarb + TX, Butacarb + TX, Butathiofos + TX, Butonate + TX, Calcium arsenate + TX, Calcium cyanide + TX, Carbon disulfide + TX, Carbon tetrachloride + TX, Cartap hydrochloride + TX, Sebacine + TX, Chlorbicyclen + TX, Chlordane + TX, Chlordecone + TX, Chloroform + TX, Chloropicrin + TX, Chloroxime + TX, Chlorpyrifos + TX, cis-resmethrin + TX, Cismethrin + TX, Crotoxyphos + TX, Cupric acetoarsenite + TX, Copper arsenate + TX, Copper oleate + TX, Cumithoate + TX, Cryolite + TX, CS708 + TX, Cyanofenphos + TX, Cyanophos + TX, Cyfluthrin + TX, Cythioate + TX, d-Tetramethrin + TX, DAEP + TX, Dazomet + TX, Decarbofuran + TX, Diamidafos + TX, Dicapthon + TX, Dichlorophenthion + TX, Dicresyl + TX, Dicyclanil + TX, Dieldrin + TX, Diethyl 5-methylpyrazol-3-yl phosphate + TX, Dirole + TX, Dimefluthrin + TX, Dimethan + TX, Dimetrin + TX, Dimethylvinphos + TX, Dimethilan + TX, Dinopro + TX, Dinocap + TX, Dinoseb + TX, Diphenolan + TX, Dioxabenzofos + TX, Dithicrofos + TX, DSP+TX, Exysterone+TX, EI 1642+TX, EMPC+TX, EPBP+TX, Ethaphos+TX, Ethiofencarb+TX, Ethyl formate+TX, Ethylene dibromide+TX, Dichloroethane+TX, Ethylene oxide+TX, EXD+TX, Fenchlorphos+TX, Fenethacarb+TX, Fenitrothion+TX, Fenoxacrim+TX, Fenpyritrin+TX, Fensulfothion+TX, Fenthion-ethyl+TX, Flucofuron+TX, Phosphamidon+TX, Phosphirate+TX, Phosphothioethane+TX, Fluthiacarb+TX, Fluthrin+TX, Guazatine+TX, Guazatine acetate+TX, Sodium tetrathiocarbonate+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterophos+TX, HHDN+TX, Hydrogen cyanide+TX, Hikindarbu+TX, IPSP+TX, Isazophos+TX, Isobenzan+TX, Isodrin+TX, Isofenphos+TX, Isolan+TX, Iprothiolane+TX, Isoxathion+TX, Juvenile hormone I+TX, Juvenile hormone II+TX, Juvenile hormone III+TX, Kelevan+TX, Kinoprene+TX, Lead arsenate+TX, Leptophos+TX, Lirimfos+TX, Lithidathion+TX, m-Cumenyl methylcarbamate+TX, Magnesium phosphide+TX, Madex+TX, Mecarbam+TX, Menazon+TX, Mercurous chloride+TX, Mesulfenphos+TX, Metam+TX, Metam-potassium+TX, Metam-sodium+TX, Methanesulfonyl fluoride+TX, Methocrotophos+TX, Methoprene+TX, Metothrin+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, Nor-nicotine+TX, O-5-Dichloro-4-iodophenyl O-ethyl ethylphosphonothioate+TX, O,O-Diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothionate+TX, O,O-Diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothionate+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, fencaptan + TX, fosnichlor + TX, phosphine + TX, hokxim-methyl + TX, pirimethaphos + TX, polychlorodicyclopentadiene isomers + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene II + TX, precocene III + TX, pyrimidophos + TX, profenofos + TX, promecarb + TX, prothiofos + TX, pyrazophos + TX, pyresmethrin + TX, cassia + TX, quinalphos-methyl + TX, quinothione + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, cadethrin + TX, ryania + TX, ryanodine + TX, sabadilla) + TX, schradan + TX, sebufos + TX, SI-0009 + TX, thiapronyl + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide salt + TX, sodium selenate + TX, sodium thiocyanate + TX, sulprofos + TX, sulprofos-sodium + TX, sulfuryl fluoride + TX, sulprophos + TX, tar oil + TX, thionazin + TX, TDE + TX, tebupirimfos + TX, temephos + TX, terallethrin + TX, tetrachloroethane + TX, trichlorphon + TX, thiosyclam + TX, thiosyclam hydrogen oxalate + TX, thionazin + TX, thiosultap + TX, thiosultap-sodium + TX, tralomethrin + TX, transpermethrin + TX, triazamate + TX, trichlorometaphos-3 + TX, trichloronate + TX, trimethacarb + TX, tolprocarb + TX, triclocarban + TX, triprene + TX, veratridine + TX, veratrine + TX, XMC + TX, zeta-methrin + TX, zinc phosphide + TX, zolaprofos + TX, meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric diphosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX,Pyriproxyfen + TX, Triflumorph + 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, Anisoflutop + TX, Benclothiaz + TX, Cytokinin + TX, DCIP + TX, Lufenuron + TX, Isamidophos + TX, Kinetin + TX, Myrothecium verrucaria composition + TX, Tetrachlorothiophene + TX, Xylenol orange + TX, Zeatin + TX, Potassium ethylxanthate + TX, Acibenzolar + TX, Acibenzolar - S - methyl + TX, Reynoutria sachalinensis extract + TX, α - Chlorohydrin + TX, Ants + TX, Barium carbonate + TX, Bistiosem + TX, Brodifacoum + TX, Bromadiolone + TX, Bromethalin + TX, Chlorophacinone + TX, Cholecalciferol + TX, Coumachlor + TX, Coumafuryl + TX, Coumatetralyl + TX, Crimidine + TX, Difenacoum + TX, Difethialone + TX, Difacinone + TX, Ergocalciferol + TX, Flocoumafen + TX, Fluoroacetamide + TX, Flupropazil + TX, Flupropazil hydrochloride + TX, Norbormide + TX, Phosacetim + TX, Phosphorus + TX, Pindone + TX, Pyrinuron + TX, Silyroside + TX, Sodium fluoroacetate + TX, Potassium sulfate + TX, Warfarin + TX, - 2 - (2 - Butoxyethoxy)ethyl piperonyl ether + TX, 5 - (1,3 - Benzodioxol - 5 - yl) - 3 - hexylcyclohex - 2 - enone + TX, Farnesol and Nerolidol + TX, Berberine + 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, Cupric oxychloride + TX, Dicyclopentadiene + TX, Thiram + TX, Zinc naphthenate + TX, Ziram + TX, Imanine + TX, Ribavirin + TX,Chloroinconiazide + TX, Mercuric oxide (II) + TX, Thiophanate-methyl + TX, Azaconazole + TX, Bitertanol + TX, Bromoconazole + TX, Cyproconazole + TX, Difenoconazole + TX, Diniconazole + TX, Epoxiconazole + TX, Fenbuconazole + TX, Fluquinconazole + TX, Flusilazole + TX, Flutriafol + TX, Flametopyr + TX, Hexaconazole + TX, Imazalil + TX, Imibenconazole + TX, Ipconazole + TX, Metconazole + TX, Microbutanyl + TX, Paclobutrazol + TX, Pefurazoate + TX, Penconazole + TX, Prothioconazole + TX, Pyriofenox + TX, Prochloraz + TX, Propiconazole + TX, Pyrisoxazole + TX, -Simconazole + 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, Fenpropizine + TX, Fenpropimorph + TX, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fluazinam + TX, Benalaxyl + TX, Furalaxyl + TX, Metalaxyl + TX, R-Metalaxyl + TX, Ofurace + TX, Oxadixyl + TX, Carbendazim + TX, Decarb + TX, Fuberidazole + TX, thiabendazole + TX, Chlorozolinate + TX, Diclozoline + TX, Microzoline + TX, Procymidone + TX, Vinclozoline + TX, Boscalid + TX, Carboxin + TX, Fenfluram + TX, Flutolanil + TX, Mepronil + TX, Oxathiapiprolin + TX, Penthiopyrad + TX, Tifluzamide + TX, Dodine + TX, Iminoctadine + TX, Azoxystrobin + TX, Dimoxystrobin + TX, Enestrobin + TX, Fenaminstrobin + TX, Fluoxastrobin + TX, Fluoxastrobin + TX, Kresoxim-methyl + TX, Metominostrobin + TX, Trifloxystrobin + TX, Orysastrobin + TX, Picoxystrobin + TX,Pyraclostrobin + TX, Pyraoxystrobin + TX, Fluoxastrobin + TX, Ferbam + TX, Mancozeb + TX, Maneb + TX, Metiram + TX, Propineb + TX, Zineb + TX, Captan + TX, Captan + TX, Fluoroimide + TX, Horpet + TX, Triflumid + TX, Bordeaux mixture + TX, Copper oxide + TX, Mancozeb + TX, Copper oxine + TX, Nitrotal-isopropyl + TX, Edifenphos + TX, Iprobenfos + TX, Phosphodifen + TX, Tokuthophos-methyl + TX, Anilazine + TX, Benfuracarb + TX, Blasticidin-S + TX, Chloroneb + TX, Chlorothalonil + TX, Cyflufenamid + TX, Cymoxanil + TX, Diclocymet + TX, Diclomezine + TX, Dichloran + TX, Diethofencarb + TX, Dimethomorph + TX, Flumorph + TX, Dithianon + TX, Ethaboxam + TX, Etridiazole + TX, Famoxadone + TX, Fenamidone + TX, Phenoxanil + TX, Ferimzone + TX, Fluazinam + TX, Flumethasulfone + TX, Fluopicolide + TX, Fluoxastrobin + TX, Flusulfamide + TX, Fluoxapropinoxad + TX, -Fenhexamid + TX, Phosphorous acid aluminum + TX, Hymexazol + TX, Iprovalicarb + TX, Cyazofamid + TX, Metasulfocarb + TX, Metrafenone + TX, Pencycuron + TX, Phthalide + TX, Polyoxin + TX, Propamocarb + TX, Pyribencarb + TX, Proquinazid + TX, Pyroquilon + TX, Pyriofenone + TX, Quinoxyfen + TX, Quintozene + TX, Thiadinyl + TX, Triazoxide + TX, Tricyclazole + TX, Triforine + TX, Validamycin + TX, Valifenalate + TX, Zoxamide + TX, Mandipropamid + 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, Isoflurprimid + TX, Isothianil + TX, Diphenamidtron + 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-trimethylinden-4-yl]pyrazole-4-carboxamide + TX, 4-(2-Bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-Bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, Fluindapyril + TX, Kresoxim-methyl (Jiaxiangjunzhi), Rubenmixianan, Diclobentiazox, Mandestrobin, 3-(4,4-Difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-Fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, Oxathiapiprolin, t-Butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylidene]amino]oxymethyl]-2-pyridyl]carbamate, Pyraziflumid, Impidacloprid, Turoprocarb, Mepentrifluconazole, Ipflufentrifluconazole, 2-(Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-inden-4-yl]pyridine-3-carboxamide, N’-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N’-[4-(4,5-Dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-Bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,[[5-Dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridachlormethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylinden-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctradin + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + TX, flurilpicoxamid + TX, fenpicoxamid + TX, metrilpicoxamid + TX, tebufloquin + TX, ipuphenoxine + TX, chinomethrin + TX, isophentamide + TX, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the method described in International Publication No. 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate + TX (which can be prepared by the method described in International Publication No. 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which can be prepared by the method described in International Publication No. 2020 / 097012), methyl N-[[4-[1-(2,(6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (which can be prepared by the method described in International Publication No. WO2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the method described in International Publication No. WO2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the method described in International Publication No. WO2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (which can be prepared by the method described in International Publication No. WO2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, benzothiostrobin + TX, fenamacril + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, fluphenoxadiazam + TX, fluthianil + TX, fluopyrimid + TX, pyrapropion + 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-Trimethylinden-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, Methyl (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoate + TX, Methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate + TX, Methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate + TX, Methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]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 International Publication No. 2020 / 079111), Methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, Methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX (These compounds can be prepared by the method described in International Publication No. 2020 / 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-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Trinexapac + TX, Kresoxim-methyl + TX, Zhongshengmycin + TX, Copper thiodiazole + TX, Zinc thiazole + TX, Abamectin + TX, Iprodione + TX, Sebutylamine + TX; N’-[5-Bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N’-[5-Bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N’-[5-Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N’-[5-Chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N’-[5-Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (These compounds can be prepared by the method described in International Publication No. WO 2015 / 155075); N’-[5-Bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (This compound can be prepared by the method described in IPCOM000249876D); N-Isopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N’-[4-(1-Cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (These compounds can be prepared by the method described in International Publication No. WO 2018 / 228896);N-Ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-Ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared by the method described in International Publication No. WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX; 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared by the methods described in International Publication No. 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-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds can be prepared by the methods described in International Publication No. 2017 / 025510);1-(4,5-Dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared by the method described in International Publication No. 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]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]propanamide + TX, 4,4-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-Dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, Ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-Dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph can be prepared by the methods described in International Publication No. WO 2017 / 055473, International Publication No. WO 2017 / 055469, International Publication No. WO 2017 / 093348 and International Publication No. 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 International Publication No. 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 International Publication No. WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (This compound can be prepared by the method described in International Publication No. WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (This compound can be prepared by the method described in International Publication No. WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (This compound can be prepared by the method described in International Publication No. WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithieno[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 International Publication No. 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-penta-3-enamide + TX (This compound can be prepared by the method described in International Publication No. WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX;N’-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by the method described in International Publication No. 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 International Publication No. 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 method described in International Publication No. WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared by the method described in International Publication No. WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared by the method described in International Publication No. 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-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the method described in International Publication No. WO 2018 / 202428); a biologically active substance selected from; Microorganisms comprising the following: Acinetobacter lwoffii + TX, Acremonium alternatum + TX + TX, Acremonium cephalosporium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, Adoxophyes orana granulovirus (AdoxGV) (Capex®) + TX, Agrobacterium radiobacter strain K84 (Galltrol-A®) + TX, Alternaria alternate + TX, Alternaria cassia + TX, Alternaria destruens (Smolder®) + TX, Ampelomyces quisqualis (AQ10®) + TX, Aspergillus flavus AF36 (AF36®) + TX, Aspergillus flavus NRRL 21882 (Aflaguard®) + TX, Aspergillus spp.) + TX, Aureobasidium pullulans + TX, Azospirillum (MicroAZ (registered trademark), TAZO B (registered trademark)) + TX, Azotobacter + TX, Azotobacter chroocuccum (Azotomeal (registered trademark)) + TX, Azotobacter cyst (Bionatural Blooming Blossoms (registered trademark)) + TX, Bacillus amyloliquefaciens + TX, Bacillus cereus + TX, Bacillus chitinosporus strain CM-1 + TX, Bacillus chitinosporus strain AQ746 + TX, Bacillus licheniformis strain HB-2 (e.g., Biostart (trademark), former name Rhizoboost (registered trademark)) + TX, Bacillus licheniformis strain 3086 (EcoGuard (registered trademark), Green Releaf (registered trademark)) + TX, Bacillus circulans + TX, Bacillus firmus (BioSafe (registered trademark), BioNem-WP (registered trademark), VOTiVO (registered trademark)) + TX, Bacillus firmus strain I-1582 + TX, Bacillus macerans + TX, Bacillus marismortui + TX, Bacillus megaterium + TX, Bacillus mycoides strain AQ726 + TX, Bacillus papillae (Milky Spore Powder (registered trademark)) + TX, Bacillus pumilus spp.) +TX, Bacillus pumilus strain GB34 (Yield Shield (registered trademark)) +TX, Bacillus pumilus strain AQ717 +TX, Bacillus pumilus strain QST 2808 (Sonata (registered trademark), Ballad Plus (registered trademark)) +TX, Bacillus spahericus (VectoLex (registered trademark)) +TX, Bacillus spp. +TX, Bacillus spp. strain AQ175 +TX, Bacillus spp. strain AQ177 +TX, Bacillus spp. strain AQ178 +TX, Bacillus subtilis strain QST 713 (CEASE (registered trademark), Serenade (registered trademark), Rhapsody (registered trademark)) +TX, Bacillus subtilis strain QST 714 (JAZZ (registered trademark)) +TX, Bacillus subtilis strain AQ153 +TX, Bacillus subtilis strain AQ743 +TX, Bacillus subtilis strain QST3002 +TX, Bacillus subtilis strain QST3004 +TX, Bacillus subtilis var. amyloliquefaciensBacillus amyloliquefaciens strain FZB24 (Taegro (registered trademark), Rhizopro (registered trademark)) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis aizawai GC 91 (Agree (registered trademark)) + TX, Bacillus thuringiensis israelensis (BMP123 (registered trademark), Aquabac (registered trademark), VectoBac (registered trademark)) + TX, Bacillus thuringiensis kurstaki (Javelin (registered trademark), Deliver (registered trademark), CryMax (registered trademark), Bonide (registered trademark), Scutella WP (registered trademark), Turilav WP (registered trademark), Astuto (registered trademark), Dipel WP (registered trademark), Biobit (registered trademark), Foray (registered trademark)) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone (registered trademark)) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P (registered trademark)) + TX, Bacillus thuringiensis strain BD#32 + TX, Bacillus thuringiensis strain AQ52 + TX, Bacillus thuringiensis var. aizawai (XenTari (registered trademark), DiPel (registered trademark)) + TX, bacteria spp.)(GROWMEND (registered trademark), GROWSWEET (registered trademark), Shootup (registered trademark)) + TX, bacteriophage of Clavipacter michiganensis (AgriPhage (registered trademark)) + TX, Bakflor (registered trademark) + TX, Beauveria bassiana (Beaugenic (registered trademark), Brocaril WP (registered trademark)) + TX, Beauveria bassiana GHA (Mycotrol ES (registered trademark), Mycotrol O (registered trademark), BotaniGuard (registered trademark)) + TX, Beauveria brongniartii (Engerlingspilz (registered trademark), Schweizer Beauveria (registered trademark), Melocont (registered trademark)) + TX, Beauveria spp. + TX, Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax (registered trademark)) + TX, Brevibacillus brevis + TX, Bacillus thuringiensis tenebrionis (Novodor (registered trademark)) + TX, BtBooster + TX, Burkholderia cepacia (Deny (registered trademark), Intercept (registered trademark),. Blue Circle (Registered Trademark))+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX, Burkholderia spp.+TX, Canadian thistle fungus (CBH Canadian Bioherbicide (Registered Trademark))+TX, Candida butyri+TX, Candida famata+TX, Candida fructus+TX, Candida glabrata+TX, Candida guilliermondii+TX, Candida melibiosica+TX, Candida oleophila strain O+TX, Candida parapsilosis+TX, Candida pelliculosa+TX, Candida pulcherrima+TX, Candida reukaufii+TX, Candida saitoana (Bio-Coat (Registered Trademark), Biocure (Registered Trademark))+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, 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 (registered trademark)) + TX, Cryptococcus humicola + TX, Cryptococcus infirmo-miniatus + TX, Cryptococcus laurentii + TX, Cryptophlebia leucotreta granulovirus (Cryptex (registered trademark)) + TX, Cupriavidus campinensis + TX, Cydia pomonella granulovirus (CYD-X (registered trademark)) + TX, Cydia pomonella granulovirus (Madex (registered trademark), Madex (registered trademark) Plus (registered trademark), Madex (registered trademark) Max, Carpovirusine Evo2 (registered trademark)) + TX, Cylindrobasidium laeve (Stumpout (registered trademark)) + TX, Cylindrocladium + TX, Debaryomyces hansenii + TX, Drechslera hawaiinensis + TX, Enterobacter cloacae + TX, Enterobacteriaceae + TX, Entomophtora virulenta (Vektor (registered trademark)) + TX, Epicoccum nigrum + TX, Epicoccum purpurascens + TX, Epicoccum spp.) +TX, Filobasidium floriforme +TX, Fusarium acuminatum +TX, Fusarium chlamydosporum +TX, Fusarium oxysporum (Fusaclean (registered trademark), Biofox C (registered trademark)) +TX, Fusarium proliferatum +TX, Fusarium spp. +TX, Galactomyces geotrichum +TX, Gliocladium catenulatum (Primastop (registered trademark), Prestop (registered trademark)) +TX, Gliocladium roseum +TX, Gliocladium spp. (SoilGard (registered trademark)) +TX, Gliocladium virens (Soilgard (registered trademark)) +TX, Granulovirus (Granupom (registered trademark)) +TX, Halobacillus halophilus +TX, Halobacillus litoralis +TX, Halobacillus trueperi +TX, Halomonas spp.)+TX, Halomonas subglaciescola+TX, Halovibrio variabilis+TX, Hanseniaspora uvarum+TX, Helicoverpa armigera nucleopolyhedrovirus (Helicovex (registered trademark))+TX, Helicoverpa zea nuclear polyhedrosis virus (Gemstar (registered trademark))+TX, Isoflavone - Hormonenetin (Myconate (registered trademark))+TX, Kloeckera apiculata+TX, Kloeckera spp.+TX, Lagenidium giganteum (Laginex (registered trademark))+TX, Lecanicillium longisporum (Vertiblast (registered trademark))+TX, Lecanicillium muscarium (Vertikil (registered trademark))+TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus (registered trademark))+TX, Marinococcus halophilus+TX, Meira geulakonigii+TX,. Metarhizium anisopliae (Met52®) + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX, Micromonospora coerulea + TX, Microsphaeropsis ochracea + TX, Muscodor albus 620 (Muscudor®) + TX, Muscodor roseus strain A3-5 + TX, Mycorrhizae spp. (AMykor®, 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, Pasteuria spp. (Econem (registered trademark))+TX, Pasteuria nishizawae+TX, Penicillium aurantiogriseum+TX, Penicillium billai (Jumpstart (registered trademark), TagTeam (registered trademark))+TX, Penicillium brevicompactum+TX, Penicillium frequentans+TX, Penicillium griseofulvum+TX, Penicillium purpurogenum+TX, Penicillium spp.) +TX, Penicillium viridicatum+TX, Phlebiopsis gigantean (Rotstop (registered trademark))+TX, Phosphomeal (registered trademark) (phosphate-solubilizing bacteria)+TX, Phytophthora cryptogea+TX, Phytophthora palmivora (Devine (registered trademark))+TX, Pichia anomala+TX, Pichia guilermondii+TX, Pichia membranaefaciens+TX, Pichia onychis+TX, Pichia stipites+TX, Pseudomonas aeruginosa+TX, Pseudomonas aureofasciens (Spot-Less Biofungicide (registered trademark))+TX, Pseudomonas cepacia+TX, Pseudomonas chlororaphis (AtEze (registered trademark))+TX, Pseudomonas corrugate+TX, Pseudomonas fluorescens strain A506 (BlightBan A506 (registered trademark))+TX, Pseudomonas putida+TX, Pseudomonas reactans+TX, Pseudomonas spp.) +TX, Pseudomonas syringae (Bio-Save (registered trademark)) +TX, Pseudomonas viridiflava +TX, Pseudomons fluorescens (Zequanox (registered trademark)) +TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L (registered trademark)) +TX, Puccinia canaliculata +TX, Puccinia thlaspeos (Wood Warrior (registered trademark)) +TX, Pythium paroecandrum +TX, Pythium oligandrum (Polygandron (registered trademark), Polyversum (registered trademark)) +TX, Pythium periplocum +TX, Rhanella aquatilis +TX, Rhanella spp. +TX, Rhizobia (Dormal (registered trademark), Vault (registered trademark)) +TX, Rhizoctonia +TX, Rhodococcus globerulus strain AQ719 +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 (registered trademark)) + TX, Scytalidium spp. + TX, Scytalidium uredinicola + TX, Spodoptera exigua nuclear polyhedrosis virus (Spod-X (registered trademark), Spexit (registered trademark)) + TX, Serratia marcescens + TX, Serratia plymuthica + TX, Serratia spp.) + TX, Sordaria fimicola + TX, Spodoptera littoralis nucleopolyhedrovirus (Littovir (registered trademark)) + TX, Sporobolomyces roseus + TX, Stenotrophomonas maltophilia + TX, Streptomyces ahygroscopicus + TX, Streptomyces albaduncus + TX, Streptomyces exfoliates + TX, Streptomyces galbus + TX, Streptomyces griseoplanus + TX, Streptomyces griseoviridis (Mycostop (registered trademark)) + TX, Streptomyces lydicus (Actinovate (registered trademark)) + TX, Streptomyces lydicus WYEC - 108 (ActinoGrow (registered trademark)) + TX, Streptomyces violaceus + TX, Tilletiopsis minor + TX, Tilletiopsis spp.)+TX, Trichoderma asperellum (T34 Biocontrol (registered trademark))+TX, Trichoderma gamsii (Tenet (registered trademark))+TX, Trichoderma atroviride (Plantmate (registered trademark))+TX, Trichoderma hamatum TH 382+TX, Trichoderma harzianum rifai (Mycostar (registered trademark))+TX, Trichoderma harzianum T-22 (Trianum-P (registered trademark), PlantShield HC (registered trademark), RootShield (registered trademark), Trianum-G (registered trademark))+TX,. Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma spp. LC 52 (Sentinel®) + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma taxi + TX, Trichoderma virens + TX, Trichoderma virens (former Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (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 (registered trademark))+TX, Ustilago maydis+TX, various bacteria and accessory micronutrients (Natural II (registered trademark))+TX, various fungi (Millennium Microbes (registered trademark))+TX, Verticillium chlamydosporium+TX, Verticillium lecanii (Mycotal (registered trademark), Vertalec (registered trademark))+TX, Vip3Aa20 (VIPtera (registered trademark))+TX, Virgibaclillus marismortui+TX, Xanthomonas campestris pv. Poae (Camperico (registered trademark))+TX, Xenorhabdus bovienii+TX, Xenorhabdus nematophilus+TX;. Plant extracts containing the following: Retenol (registered trademark) + TX, azadirachtin (Plasma Neem Oil (registered trademark), AzaGuard (registered trademark), MeemAzal (registered trademark), Molt-X (registered trademark), Botanical IGR (Neemazad (registered trademark), Neemix (registered trademark)) + TX, rapeseed oil (Lilly Miller Vegol (registered trademark)) + TX, Chenopodium ambrosioides near ambrosioides (Requiem (registered trademark)) + TX, Chrysanthemum extract (Crisant (registered trademark)) + TX, neem oil extract (Trilogy (registered trademark)) + TX, essential oil of Labiatae (Botania (registered trademark)) + TX, extract of clove, rosemary, peppermint and thyme oil (Garden insect killer (registered trademark)) + TX, glycine betaine (Greenstim (registered trademark)) + TX, garlic + TX, lemongrass oil (GreenMatch (registered trademark)) + TX, neem oil + TX, Nepeta cataria (catnip oil) + TX, Nepeta catarina + TX, nicotine + TX, oregano oil (MossBuster (registered trademark)) + TX, Pedaliaceae oil (Nematon (registered trademark)) + TX, pyrethrum + TX, Quillaja saponaria (NemaQ (registered trademark)) + TX, Reynoutria sachalinensis (Regalia (registered trademark), Sakalia (registered trademark)) + TX, rotenone (Eco Roten (registered trademark)) + TX, Rutaceae extract (Soleo (registered trademark)) + TX, soybean oil (Ortho ecosense (registered trademark)) + TX, Melaleuca alternifolia extract (also called tea tree oil) (Timorex Gold (registered trademark)) + TX, thyme oil + TX, AGNIQUE (registered trademark) MMF + TX, BugOil (registered trademark) + TX, mixture of rosemary, cumin, peppermint, thyme and cinnamon extracts (EF300 (Registered Trademark)) + TX, a mixture of clove, rosemary and peppermint extracts (EF 400 (Registered Trademark)) + TX, a mixture of clove, pepper, mint oil and garlic (Soil Shot (Registered Trademark)) + TX, kaolin (Screen (Registered Trademark)) + TX, storage glucan of brown algae (Laminarin (Registered Trademark)) + TX; Pheromones including the following: blackheaded fireworm pheromone (3M Sprayable Blackheaded Fireworm Pheromone (Registered Trademark)) + TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate C-Plus (Registered Trademark)) + TX, grape berry moth pheromone (3M MEC-GBM Sprayable Pheromone (Registered Trademark)) + TX, leafroller pheromone (3M MEC-LR Sprayable Pheromone (Registered Trademark)) + TX, Muscamone (Snip7 Fly Bait (Registered Trademark), Starbar Premium Fly Bait (Registered Trademark)) + TX, oriental fruit moth pheromone (3M oriental fruit moth sprayable pheromone (Registered Trademark)) + TX, peachtree borer pheromone (Isomate-P (Registered Trademark)) + TX, tomato pinworm pheromone (3M Sprayable pheromone (Registered Trademark)) + TX, Entostat powder (extract from palm tree) (Exosex CM (Registered Trademark)) + TX, (3E,8Z,11Z)-3,11-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 (Registered Trademark) + TX, Biolure (Registered Trademark) + TX, Check-Mate (Registered Trademark) + TX, lavandulyl senecioate + TX; Macrobials comprising the following: Aphelinus abdominalis + TX, Aphidius ervi (Aphelinus-System (registered trademark)) + TX, Acerophagus papaya + TX, Adalia bipunctata (Adalia-System (registered trademark)) + TX, Adalia bipunctata (Adaline (registered trademark)) + TX, Adalia bipunctata (Aphidalia (registered trademark)) + TX, Ageniaspis citricola + TX, Ageniaspis fuscicollis + TX, Amblyseius andersoni (Anderline (registered trademark), Andersoni-System (registered trademark)) + TX, Amblyseius californicus (Amblyline (registered trademark), Spical (registered trademark)) + TX, Amblyseius cucumeris (Thripex (registered trademark), Bugline cucumeris (registered trademark)) + TX, Amblyseius fallacis (Fallacis (registered trademark)) + TX, Amblyseius swirskii (Bugline swirskii (registered trademark), Swirskii-Mite (registered trademark)) + TX, Amblyseius womersleyi (WomerMite (registered trademark)) + TX, Amitus hesperidum + TX, Anagrus atomus + TX, Anagyrus fusciventris + TX, Anagyrus kamali + TX, Anagyrus loecki + TX, Anagyrus pseudococcus (AnagyrusPseudococci)(Citripar (registered trademark)) + TX, Anicetus benefices + TX, Anisopteromalus calandrae + TX, Anthocoris nemoralis (Anthocoris-System (registered trademark)) + TX, Aphelinus abdominalis (Apheline (registered trademark), Aphiline (registered trademark)) + TX, Aphelinus asychis + TX, Aphidius colemani (Aphipar (registered trademark)) + TX, Aphidius ervi (Ervipar (registered trademark)) + TX, Aphidius gifuensis + TX, Aphidius matricariae (Aphipar-M (registered trademark)) + TX, Aphidoletes aphidimyza (Aphidend (registered trademark)) + TX, Aphidoletes aphidimyza (Aphidoline (registered trademark)) + TX, Aphytis lingnanensis + TX, Aphytis melinus + TX, Aprostocetus hagenowii + TX, Atheta coriaria (Staphyline (registered trademark)) + TX, Bombus spp. + TX, Bombus terrestris (Natupol Beehive (registered trademark)) + TX, Bombus terrestris (Beeline (registered trademark), Tripol (registered trademark)) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, ChrysoperlaChrysoperla carnea)(Chrysoline(trademark)) + TX, Chrysopa carnea)(Chrysopa(trademark)) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp. + TX, Coccidoxenoides perminutus)(Planopar(trademark)) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri)(Cryptobug(trademark), Cryptoline(trademark)) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica + TX, Dacnusa sibirica)(Minusa(trademark)) + TX, Diglyphus isaea)(Diminex(trademark)) + TX, Delphastus catalinae)(Delphastus(trademark)) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda(Diaparsisjucunda)+TX, Diaphorencyrtus aligarhensis+TX, Diglyphus isaea+TX, Diglyphus isaea (Miglyphus (registered trademark), Digline (registered trademark))+TX, Dacnusa sibirica (DacDigline (registered trademark), Minex (registered trademark))+TX, Diversinervus spp.+TX, Encarsia citrina+TX, Encarsia formosa (Encarsia max (registered trademark), Encarline (registered trademark), En-Strip (registered trademark))+TX, Eretmocerus eremicus (Enermix (registered trademark))+TX, Encarsia guadeloupae+TX, Encarsia haitiensis+TX, Episyrphus balteatus (Syrphidend (registered trademark))+TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX, Eretmocerus eremicus (Ercal (registered trademark), Eretline e (registered trademark))+TX, Eretmocerus eremicus (Bemimix (registered trademark))+TX, Eretmocerus hayati+TX, Eretmocerus mundus (Bemipar (registered trademark), Eretline m (registered trademark))+TX, Eretmocerus siphonini+TX, Exochomus quadripustulatus+TX, Feltiella acarissuga (FeltiellaAcarisuga)(Spidend(trademark))+TX, Feltiella acarisuga)(Feltiline(trademark))+TX, Fopius arisanus)+TX, Fopius ceratitivorus)+TX, Hormoneractin(Wirless Beehome(trademark))+TX, Franklinothrips vespiformis)(Vespop(trademark))+TX, Galendromus occidentalis)+TX, Goniozus legneri)+TX, Habrobracon hebetor)+TX, Harmonia axyridis)(HarmoBeetle(trademark))+TX, Heterorhabditis spp.)(Lawn Patrol(trademark))+TX, Heterorhabditis bacteriophora)(NemaShield HB(trademark), Nemaseek(trademark), Terranem-Nam(trademark), Terranem(trademark), Larvanem(trademark), B-Green(trademark), NemAttack(trademark), Nematop(trademark))+TX, Heterorhabditis megidis)(Nemasys H(trademark), BioNem H(trademark), Exhibitline hm(trademark), Larvanem-M(trademark))+TX, Hippodamia convergens)+TX, Hypoaspis aculeifer)(Aculeifer-System(trademark), Entomite-A (registered trademark)) + TX, Hypoaspis miles (Hypoline m (registered trademark), Entomite-M (registered trademark)) + TX, Lbalia leucospoides + TX, Lecanoideus floccissimus + TX, Lemophagus errabundus + TX, Leptomastidea abnormis + TX, Leptomastix dactylopii (Leptopar (registered trademark)) + TX, Leptomastix epona + TX, Lindorus lophanthae + TX, Lipolexis oregmae + TX, Lucilia caesar (Natufly (registered trademark)) + TX, Lysiphlebus testaceipes + TX, Macrolophus caliginosus (Mirical-N (registered trademark), Macroline c (registered trademark), Mirical (registered trademark)) + TX, Mesoseiulus longipes + TX, Metaphycus flavus + TX, Metaphycus lounsburyi + TX, Micromus angulatus (Milacewing (registered trademark)) + TX, Microterys flavus + TX, Muscidifurax raptorellus and Spalangia cameroni (Biopar (registered trademark)) + TX, Neodryinus typhlocybae + TX, Neoseiulus californicus + TX, Neoseiulus cucumerisAmblyseius cucumeris)(THRYPEX (registered trademark)) + TX, Neoseiulus fallacis + TX, Nesidiocoris tenuis (NesidioBug (registered trademark), Nesibug (registered trademark)) + TX, Ophyra aenescens (Biofly (registered trademark)) + TX, Orius insidiosus (Thripor-I (registered trademark), Oriline i (registered trademark)) + TX, Orius laevigatus (Thripor-L (registered trademark), Oriline l (registered trademark)) + TX, Orius majusculus (Oriline m (registered trademark)) + TX, Orius strigicollis (Thripor-S (registered trademark)) + TX, Pauesia juniperorum + TX, Pediobius foveolatus + TX, Phasmarhabditis hermaphrodita (Nemaslug (registered trademark)) + TX, Phymastichus coffea + TX, Phytoseiulus macropilus + TX, Phytoseiulus persimilis (Spidex (registered trademark), Phytoline p (registered trademark)) + TX, Podisus maculiventris (Podisus (registered trademark)) + TX, Pseudacteon curvatus + TX, Pseudacteon obtusus + TX, Pseudacteon tricuspis + TX, Pseudaphycus maculipennis + TX, Pseudleptomastix mexicanamexicana)+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp.+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae (Ervibank (registered trademark))+TX, Steinernema carpocapsae (Nematac C (registered trademark), Millenium (registered trademark), BioNem C (registered trademark), NemAttack (registered trademark), Nemastar (registered trademark), Capsanem (registered trademark))+TX, Steinernema feltiae (NemaShield (registered trademark), Nemasys F (registered trademark), BioNem F (registered trademark), Steinernema-System (registered trademark), NemAttack (registered trademark), Nemaplus (registered trademark), Exhibitline sf (registered trademark), Scia-rid (registered trademark), Entonem (registered trademark))+TX, Steinernema kraussei (Nemasys L (registered trademark), BioNem L (registered trademark), Exhibitline srb (registered trademark))+TX, Steinernema riobrave (BioVector (registered trademark), BioVektor (registered trademark))+TX, Steinernema scapterisci (Nematac S (registered trademark))+TX, Steinernema spp.+TX, Steinernematid spp. (Guardian Nematodes (registered trademark))+TX, Stethorus punctilum (Stethoruspunctillum)(Stethorus (registered trademark)) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b (registered trademark)) + TX, 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; Other biological agents comprising the following: abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporioides (Collego®) + TX, copper octanoate (Cueva®) + TX, 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, Trapline y® + TX, Gallex® + TX, Grower’s Secret® + TX, homo-brassinolide + 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 salt 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 GrasshopperControl (registered trademark)) + TX, Adhesive Trap (Trapline YF (registered trademark), Rebell Amarillo (registered trademark)) + TX, and Trap (Takitrapline y + b (registered trademark)) + TX; (1) An antibacterial agent selected from the following group: (1.1) Examples are bacteria such as: Bacillus mojavensis strain R3B (Accession No. NCAIM(P)B001389) from Certis USA LLC (International Publication No. WO 2013 / 034938) + TX; Bacillus pumilus, in particular strain BU F-33 having NRRL Accession No. 50185 (CARTISSA® from BASF, EPA Registration No. 71840-19) + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661, US Patent No. 6,060,051) + TX; Bacillus subtilis strain BU1814 (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX; Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM10271 (available as TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5) from Novozymes) + TX; Bacillus subtilis CX-9060 from Certis USA LLC + TX; Bacillus sp., in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd., having Accession No. FERM BP-8234, US Patent No. 7,094,592) + TX; Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129, International Publication No. WO 2016 / 154297 + TX; Paenibacillus polymyxa, in particular strain AC-1 (e.g., Green Biotech Company Ltd.Manufactured TOPSEED (registered trademark)) + TX; Pantoea agglomerans, particularly strain E325 (accession number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL (trademark) FD BIOPESTICIDE from Northwest Agri Products) + TX; Pseudomonas proradix from Sourcon Padena (e.g., PRORADIX (registered trademark)) + TX; and... (1.2) Examples thereof are the following fungi: Aureobasidium pullulans, particularly blastospores of strain DSM14940, blastospores of strain DSM 14941 or a mixture of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR (registered trademark) and BLOSSOM PROTECT (registered trademark) from bio-ferm, CH) + TX; Pseudozyma aphidis (disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX; Saccharomyces cerevisiae, particularly strain CNCM number 1-3936, CNCM number 1-3937, CNCM number 1-3938 or CNCM number 1-3939 (disclosed in International Publication No. 2010 / 086790 from Lesaffre et Compagnie, FR) + TX; (2) Biological fungicides and bactericides selected from the following groups: (2.1) Examples are the following bacteria: 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 having accession number DSM10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)) + TX; Bacillus amyloliquefaciens, in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. as Double Nickel™, having accession number FERM BP-8234, U.S. Patent No. 7,094,592) + TX; Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, International Publication No. 2014 / 028521) (STARGUS® from Marrone Bio Innovations) + TX; Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (available from ABiTEP, DE as RHIZOVITAL®) + TX; Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN™ from University of Pretoria) + TX; Bacillus licheniformis, in particular strain SB3086 having accession number ATCC55406, International Publication No. 2003 / 000051 (available from Novozymes as ECOGUARD® Biofungicide and GREEN RELEAF™) + TX;Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) manufactured by FMC Corp.) + TX; Bacillus methylotrophicus strain BAC-9912 (manufactured by the Chinese Academy of Sciences’ Institute of Applied Ecology) + TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) from Certis USA LLC (International Publication No. WO 2013 / 034938) + TX; Bacillus mycoides, isolate, having accession number B-30890 (available from Certis USA LLC as BMJ TGAI® or WG and LifeGard™) + TX; Bacillus pumilus, particularly strain QST2808 (available from Bayer CropScience LP, US as SONATA®, having accession number NRRL B-30087, described in US Patent No. 6,245,551) + TX; Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE as Yield Shield®) + TX; Bacillus pumilus, particularly strain BU F-33 having NRRL accession number 50185 (available as part of the CARTISSA product from BASF, EPA registration number 71840-19) + TX; Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, having NRRL accession number B21661, described in US Patent No. 6,060,051) + TX;Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered numbers 4764, 5454, 5096 and 5277, registered in Taiwan as a biological fungicide and bactericide) + TX; Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX, having accession number NRRL B-50595, U.S. Patent No. 5,061,495) + TX; Bacillus subtilis strain GB03 (available from Bayer AG, DE as Kodiak®) + TX; Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA) + TX; Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co., Ltd.) + TX; Bacillus subtilis KTSB strain (FOLIACTIVE® manufactured by Donaghys) + TX; Bacillus subtilis IAB / BS03 (AVIV™ manufactured by STK Bio-Ag Technologies, PORTENTO® manufactured by Idai Nature) + TX; Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered numbers 4764, 5454, 5096 and 5277, registered in Taiwan as a biological fungicide and bactericide) + TX; Paenibacillus epiphyticus from BASF SE (International Publication No. 2016 / 020371) + TX; Paenibacillus polymyxa ssp. plantarum from BASF SE (International Publication No. 2016 / 020371) + TX;A strain of Paenibacillus sp. having accession number NRRL B-50972 or accession number NRRL B-67129, International Publication No. 2016 / 154297 + TX; Pseudomonas chlororaphis strain AFS009, having accession number NRRL B-50897, International Publication No. 2017 / 019448 (e.g., HOWLER (trademark) and ZIO (registered trademark) manufactured by AgBiome Innovations, US) + TX; Pseudomonas chlororaphis, particularly strain MA342 (e.g., CEDOMON (registered trademark), CERALL (registered trademark) and CEDRESS (registered trademark) by Bioagri and Koppert) + TX; Pseudomonas fluorescens strain A506 (e.g., BLIGHTBAN (registered trademark) A506 by NuFarm) + TX; Pseudomonas proradix (e.g., PRORADIX (registered trademark) manufactured by Sourcon Padena) + TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM7206) (see MYCOSTOP (registered trademark) from Verdera, PREFENCE (registered trademark) manufactured by BioWorks, Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO-IRON (registered trademark) and ACTINOVATE (registered trademark) manufactured by Novozymes) + TX; and; (2.2) Examples thereof are the following fungi: Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 10® by IntrachemBio Italia) + TX; Ampelomyces quisqualis strain AQ10 having accession number CNCM1-807 (e.g. AQ 10® by IntrachemBio Italia) + TX; Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® manufactured by Syngenta / ChemChina) + TX; Aureobasidium pullulans, in particular blastospores of strain DSM14940 + TX; Aureobasidium pullulans, in particular blastospores of strain DSM 14941 + TX; Aureobasidium pullulans, in particular a mixture of blastospores of strains DSM14940 and DSM 14941 (e.g. Botector® by bio-ferm, CH) + TX; Chaetomium cupreum (accession number CABI 353812) (e.g. BIOKUPRUM™ by AgriLife) + TX; Chaetomium globosum (available as RIVADIOM® by Rivale) + TX; Cladosporium cladosporioides, strain H39, having accession number CBS122244, US Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Landbouwkundig Onderzoek) + TX; Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM9660, e.g. Contans® manufactured by 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 (also known as Clonostachys rosea f rosea), in particular strain 321U from Adjuvants Plus, strain ACM941 disclosed by Xue A.G. (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 strain IK726 (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;The conidia of the strain Lecanicillium lecanii (formerly known as Verticillium lecanii), such as Vertalec® by Koppert / Arysta + TX; Metschnikowia fructicola, particularly the strain NRRL Y-30752, (B2.2.3) + TX; Microsphaeropsis ochracea + TX; Muscodor roseus, particularly the strain A3-5 (accession number NRRL 30548) + TX; Penicillium steckii from BASF SE (DSM27859, WO 2015 / 067800) + TX; Penicillium vermiculatum + TX; the Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C manufactured by Danstar Ferment) + TX; Pichia anomala, the strain WRL-076 (NRRL Y-30842), US Patent No. 7,579,183 + TX; Pseudozyma flocculosa, the strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., CA) + TX; Saccharomyces cerevisiae, particularly the strain LASO2 (Agro-Levures et Derives), the cell wall of the strain LAS117 (CEREVISANE® manufactured by Lesaffre, ROMEO® manufactured by BASF SE), the strains with CNCM numbers 1-3936, 1-3937, 1-3938, 1-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790) + TX; Simplicillium lanosoniveum + TX; Talaromyces flavus, the strain V117b + TX;Trichoderma asperelloides JM41R (receiving number NRRL B-50759) (TRICHO PLUS® manufactured by BASF SE) + TX; Trichoderma asperellum, particularly strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX; Trichoderma asperellum, particularly strain SKT-1, having receiving number FERM P-16510 (e.g., ECO-HOPE® manufactured by Kumiai Chemical Industry Co., Ltd.), strain T34 (e.g., T34 Biocontrol by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro + TX; Trichoderma atroviride, particularly strain SC1 (receiving number CBS 122089, International Publication No. 2009 / 116106 and U.S. Patent No. 8,431,120 (Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Ltd.) + TX; Trichoderma atroviride, strain CNCM 1-1237 (e.g., Esquive® WP from Agrauxine, FR) + TX; Trichoderma atroviride, strain number V08 / 002387 + TX; Trichoderma atroviride, strain NMI number V08 / 002388 + TX; Trichoderma atroviride, strain NMI number V08 / 002389 + TX; Trichoderma atroviride, strain NMI number V08 / 002390 + TX; Trichoderma atroviride, strain LC52 (e.g., Tenet by Agrimm Technologies Ltd.) + TX;Trichoderma atroviride, strain ATCC 20476 (IMI 206040) + TX; Trichoderma atroviride, strain T11 (IMI352941 / CECT20498) + TX; Trichoderma atroviride, strain SKT-1 (FERM P-16510), Japanese Patent Laid-Open No. 11-253151 + TX; Trichoderma atroviride, strain SKT-2 (FERM P-16511), Japanese Patent Laid-Open No. 11-253151 + TX; Trichoderma atroviride, ; Strain SKT-3 (FERM P-17021), JP-A-11-253151 + TX; Trichoderma fertile (e.g., the product TrichoPlus manufactured by BASF) + TX; Trichoderma gamsii (former name T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., BioDerma by AGROBIOSOL DE MEXICO, S.A.DE C.V.) + TX; Trichoderma gamsii (former name T. viride), strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA (registered trademark) by AGROBIOSOL DE MEXICO, S.A.DE C.V.) + TX; Trichoderma harmatum + TX; Trichoderma harmatum having accession number ATCC 28012 + TX; Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa SimbT5 (Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum rifai T39 (e.g., Trichodex (registered trademark) manufactured by Makhteshim, US) + 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 (available as T-GRO (registered trademark) 7456 by Dagutat Biolab) + TX;Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden) + TX; Trichoderma stromaticum having accession number Ts3550, (e.g., Tricovab by CEPLAC, Brazil) + TX; Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (e.g., SoilGard by Certis, US) + TX; Trichoderma virens strain G-41, formerly known as Gliocladium virens (accession number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP manufactured by BioWorks, US) + TX; Trichoderma viride, strain TV1 (e.g., Trianum-P by Koppert) + TX; Trichoderma viride, particularly strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161:125-137) + TX; Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), having accession number CABI CC IMI 392716, a mixture of Trichoderma gamsii (former name T. viride) strain ICC 080, accession number IMI 392151 (e.g., BIO-TAM™ by Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, S.A.de C.V.) + TX;Ulocladium oudemansii strain U3 having accession number NM 99 / 06216 (e.g., BOTRY-ZEN® manufactured by Botry-Zen Ltd, New Zealand and BOTRYSTOP® manufactured by BioWorks, Inc.) + TX; Verticillium albo-atrum (syn. V. dahliae), strain WCS850 having accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® manufactured by Tree Care Innovations) + TX; Verticillium chlamydosporium + TX; (3) A biological control agent having the effect of improving the growth and / or health of plants selected from the following group: (3.1) Examples are the following bacteria: Azospirillum brasilense (e.g., VIGOR® manufactured by KALO, Inc.) + TX; Azospirillum lipoferum (e.g., VERTEX-IF™ manufactured by TerraMax, Inc.) + TX; Azorhizobium caulinodans, particularly strain ZB-SK-5 + TX; Azotobacter chroococcum, particularly strain H23 + TX; Azotobacter vinelandii, particularly strain ATCC 12837 + TX; a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available from Agrinos as INVIGORATE®) + TX; Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® manufactured by Biofilm Crop Protection) + TX; Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542, International Publication No. WO 2017 / 205258) + TX; Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS®) + TX; Bacillus amyloliquefaciens, particularly strain IN937a + TX; Bacillus amyloliquefaciens, particularly strain FZB42 (e.g., RHIZOVITAL® manufactured by ABiTEP, DE) + TX; Bacillus amyloliquefaciens BS27 (Accession No. NRRL B-5015) + TX;Members of the Bacillus cereus family EE128 (NRRL number B-50917) + TX; Members of the Bacillus cereus family EE349 (NRRL number B-50928) + TX; Bacillus cereus, especially strain BP01 (ATCC 55675, for example MEPICHLOR® manufactured by Arysta Lifescience, US) + TX; Bacillus firmus, especially strain CNMC 1-1582 (for example VOTIVO® manufactured by BASF SE) + TX; Bacillus mycoides BT155 (NRRL number B-50921) + TX; Bacillus mycoides EE118 (NRRL number B-50918) + TX; Bacillus mycoides EE141 (NRRL number B-50916) + TX; Bacillus mycoides BT46-3 (NRRL number B-50922) + TX; Bacillus pumilus, especially strain QST2808 (accession number NRRL number B-30087) + TX; Bacillus pumilus, especially strain GB34 (for example YIELD SHIELD® manufactured by Bayer Crop Science, DE) + TX; Bacillus siamensis, especially strain KCTC 13613T + TX; Bacillus subtilis, especially strain QST713 / AQ713 (having NRRL accession number B-21661 and described in US Patent No. 6,060,051, available from Bayer CropScience LP, US as SERENADE® OPTI or SERENADE® ASO) + TX; Bacillus subtilis, especially strain AQ30002 (described in accession number NRRL B-50421 and US Patent Application Publication No. 13 / 330,576) + TX;Bacillus subtilis, particularly strain AQ30004 (described in NRRL No. B-50455 and U.S. Patent Application Publication No. 13 / 330,576) + TX; Bacillus subtilis strain BU1814 (available from BASF SE under the trade name TEQUALIS®), Bacillus subtilis rm303 (RHIZOMAX® from Biofilm Crop Protection) + TX; Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7) + TX; a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation under the trade names 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; a species of 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, particularly strain PN1 + TX; Rhizobium leguminosarum, particularly bv. viceae strain Z25 (accession number CECT 4585) + TX; Paenibacillus polymyxa, particularly strain AC-1 (e.g., TOPSEED® from Green Biotech Company Ltd.) + TX; Serratia marcescens, particularly strain SRM (accession number MTCC 8708) + TX; Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX; a species of Bacillus sp. (e.g., CROPAID® from Cropaid Ltd UK) + TX; and; (3.2) Examples thereof are the following fungi: Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, BioAct from Bayer CropScience Biologics GmbH for example) + TX; Penicillium bilaii, strain ATCC 22348 (JumpStart® from Acceleron BioAg for example), Talaromyces flavus, strain V117b + TX; Trichoderma atroviride strain CNCM I-1237 (Esquive® WP from Agrauxine, FR for example), Trichoderma viride, for example strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161:125-137) + TX; Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, from Agrimm Technologies Ltd. for example)Sentinel® + TX from; 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, ZA) + 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 ATCC20851 + TX; Pythium oligandrum strain M1 (ATCC38472, e.g., Polyversum from Bioprepraty, CZ) + TX; Trichoderma virens strain GL-21 (e.g., SoilGard® from Certis, USA) + TX; Verticillium albo-atrum (syn. V. dahliae) strain WCS850 (CBS276.92. For example, Trichoderma atroviride from Tree Care Innovations), +TX; Trichoderma atroviride, particularly strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number 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 (e.g., Myco-Sol from Agri-Enterprise, LLC, former Helena Chem. Company) +TX; Rhizopogon fulvigleba (e.g., Myco-Sol from Agri-Enterprise, LLC, former Helena Chem. Company) +TX; Trichoderma virens strain GI-3 +TX;. (4) An insecticidally effective biological control agent selected from the following (4.1) Examples are the following bacteria: Agrobacterium radiobacter strain K84 (Galltrol from AgBiochem Inc.) + TX; Bacillus amyloliquefaciens, particularly strain PTS-4838 (e.g., AVEO from Valent Biosciences, US) + TX; Bacillus firmus, particularly strain CNMC1-1582 (e.g., VOTIVO® from BASF SE) + TX; Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC) + TX; Bacillus sphaericus, particularly Serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences, US) + TX; Bacillus thuringiensis subsp. aizawai, particularly strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences) + TX; Bacillus thuringiensis subsp. aizawai, particularly serotype H-7 (e.g., FLORBAC® WG from Valent BioSciences, US) + TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., AQUABAC® by Becker Microbial Products, IL) + TX; Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC® by Valent BioSciences, US) + TX; Bacillus thuringiensis subsp. aizawaiBacillus aizawai strain GC-91 + TX; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory) + TX; Bacillus thuringiensis var. japonensis strain Buibui + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 (manufactured by Becker Microbial Products, IL) + TX; Bacillus thuringiensis subsp. kurstaki strain BMP 123 by Becker Microbial Products, IL, e.g., BARITONE from Bayer CropScience + TX; Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., DIPEL® ES manufactured by Valent BioSciences, US) + TX; Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC® by AEF Global) + TX; Bacillus thuringiensis subsp. kurstaki strain ABTS351 + TX; Bacillus thuringiensis subsp. kurstaki strain PB 54 + TX; Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN® from Certis, US) + TX; Bacillus thuringiensis subsp. kurstakiBacillus thuringiensis subsp. kurstaki strain SA 12 (Certis, THURICIDE from the US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG2348 (Certis, LEPINOX® from the US) + TX; Bacillus thuringiensis subsp. kurstaki strain EG 7841 (Certis, CryMAX® from the US) + TX; Bacillus thuringiensis subsp. tenebrionis strain NB176 (SD-5428, NOVODOR® FC manufactured by BioFa DE for example) + TX; Brevibacillus laterosporus (LATERAL® from Ecolibrium Biologicals Ltd.) + TX; Burkholderia spp., particularly Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319; International Publication Nos. WO 2011 / 106491 and WO 2013 / 032693; MBI206 TGAI and ZELTO® manufactured by Marrone Bio Innovations for example) + TX; Chromobacterium subtsugae, particularly strain PRAA4-1T (for example, MBI-203; GRANDEVO® manufactured by Marrone Bio Innovations for example) + TX; Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) + TX; Paenibacillus popilliae (former name Bacillus popilliae); for example St.MILKY SPORE POWDER (trademark) or MILKY SPORE GRANULAR (trademark) + TX manufactured by Gabriel Laboratories; Pasteuria nishizawae strain Pn1 (CLARIVA from Syngenta / ChemChina) + TX; Serratia entomophila (e.g., INVADE (registered trademark) by Wrightson Seeds) + TX; Serratia marcescens, particularly strain SRM (accession number MTCC 8708) + TX; Trichoderma asperellum (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP MALES (registered trademark) manufactured by MosquitoMate) + TX; and... (4.2) Examples are the following fungi: Beauveria bassiana strain ATCC 74040 (e.g., NATURALIS® from Intrachem Bio Italia) + TX; Beauveria bassiana strain GHA (accession number ATCC 74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam Int. Corp.) + TX; Beauveria bassiana strain ATP02 (accession number DSM 24665) + TX; Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus, strain Apopka 97, e.g., PREFERAL® from SePRO) + TX; Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074, disclosed in International Publication No. WO 2017 / 066094; Pioneer Hi-Bred International) + TX; Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) + TX; Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) + TX; Paecilomyces lilacinus strain 251 (MELOCON® from Certis, US) + TX; Zoophtora radicans + TX; (5) Viruses selected from the group consisting of: Adoxophyes orana granulosis virus (GV) + TX; Cydia pomonella granulosis virus (GV) + TX; Helicoverpa armigera (cotton bollworm) nucleopolyhedrovirus (NPV) + TX; Spodoptera exigua mNPV + TX; Spodoptera frugiperda (fall armyworm) mNPV + TX; Spodoptera littoralis NPV + TX; (6) Bacteria and fungi that can be added as "inoculant strains" to plants, plant parts or plant tissues selected from the following, and promote plant growth and plant health due to their specific characteristics: Agrobacterium spp. + TX; Azorhizobium caulinodans + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., especially Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX; Gigaspora spp. or Gigaspora monosporum + TX; Glomus spp. + TX; Laccaria spp. + TX; Lactobacillus buchneri + TX; Paraglomus spp. + TX; Pisolithus tinctorus + TX; Pseudomonas spp. + TX; Rhi...

Claims

1. Equation (I) 【Chemistry 1】 (In the formula, A is either O or S; X is N or CR 8 And; Y is N or CR 8 And; Z is N or CR 8 And; However, at least one of X, Y, and Z is N; R 1 is hydrogen, C 1 ~C 6 -alkyl, C 1 ~C 6 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -halocycloalkyl, C 2 ~C 6 -alkenyl, C 2 ~C 6 -haloalkenyl, C 2 ~C 6 -alkynyl, C 2 ~C 6 -haloalkynyl, C 1 ~C 6 -alkoxy, C 1 ~C 6 -haloalkoxy, C 1 ~C 6 -alkoxy-C 1 ~C 6 -alkyl, C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, C 3 ~C 6 -halocycloalkyl-C 1 ~C 6 -alkyl, cyano-C 1 ~C 6 -alkyl, cyano-C 3 ~C 6 -cycloalkyl, cyano-C 3 ~C 6 -cycloalkyl-C 1 ~C 6 -alkyl, cyano-heterocycloalkyl, hydroxy-C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkyl-carbonyl-oxy-C 3 ~C 6 -cycloalkyl, C 1 ~C 6 -alkylsulfonyl-oxy-C 3 ~C 6 -cycloalkyl, C 1 to C 6 -alkoxy-C 3 to C 6 -cycloalkyl, C 1 to C 6 -haloalkoxy-C 3 to C 6 -cycloalkyl, C 1 to C 6 -alkylthio-C 3 to C 6 -cycloalkyl, C 1 to C 6 -haloalkylthio-C 3 to C 6 -cycloalkyl, C 1 to C 6 -alkylsulfinyl-C 3 to C 6 -cycloalkyl, C 1 to C 6 -haloalkylsulfinyl-C 3 to C 6 -cycloalkyl, C 1 to C 6 -alkylsulfonyl-C 3 to C 6 -cycloalkyl, C 1 to C 6 -haloalkylsulfonyl-C 3 to C 6 -cycloalkyl, C 2 to C 6 -alkynyl-C 3 to C 6 -cycloalkyl, C 1 to C 6 -alkoxycarbonyl-C 3 to C 6 -cycloalkyl, carboxy-C 3 to C 6 -cycloalkyl, carbamoyl-C 3 to C 6 -cycloalkyl, C 1 to C 6 -alkylaminocarbonyl-C 3 to C 6 -cycloalkyl (which may be mono- or polysubstituted by R 8 ), C 4 to C 8 - Bicycloalkyl, C 1 ~C 6 - Alkoxyimino, phenyl (this is R 10 Phenylen-C (can be monosubstituted or polysubstituted by) 1 ~C 6 - Alkyl (the phenyl is R 10 (The heteroaryl may be monosubstituted or polysubstituted by R) 10 (may be monosubstituted or polysubstituted by) heteroaryl-C 1 ~C 3 - Alkyl (the heteroaryl is R 10 (may be monosubstituted or polysubstituted by) heteroaryl-C 3 ~C 6 -Cycloalkyl (the heteroaryl is R 10 (can be monosubstituted or polysubstituted by R) heterocycloalkyl (this is R 8 (may be substituted by) heterocycloalkyl-C 1 ~C 6 - Alkyl (This is R 8 (may be substituted by) or heterocycloalkyl-C 3 ~C 6 -Cycloalkyl (the heterocycloalkyl is R 8 (which can be replaced by; R 2 is hydrogen, C 1 ~C 6 - Alkyl, C 1 ~C 6 - Haloalkyl, C 3 ~C 6 - Cycloalkyl, C 3 ~C 6 - Halocycloalkyl, C 2 ~C 6 - Alkenil, C 2 ~C 6 - Alkenil, C 2 ~C 6 - Haloalkenyl, C 2 ~C 6 - Alkinyl, C 2 ~C 6 - Haloalkynyl, C 1 ~C 6 - Alkoxy, C 1 ~C 6 -Alkoxy-C 1 ~C 6 - Alkyl, C 1 ~C 6 - Haloalkoxy, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 - Alkyl, C 3 ~C 6 -Halocycloalkyl-C 1 ~C 6 - Alkyl, phenyl (this is R 10 Phenylen-C (can be monosubstituted or polysubstituted by) 1 ~C 6 - Alkyl (the phenyl is R 10 (The heteroaryl may be monosubstituted or polysubstituted by R) 10 (may be monosubstituted or polysubstituted by) heteroaryl-C 1 ~C 3 - Alkyl (the heteroaryl is R 10 (Can be monosubstituted or polysubstituted by) cyano, cyano-C 1 ~C 6 -Alkyl, cyano-C 3 ~C 6 -Cycloalkyl, hydroxy, formyl, C 1 ~C 6 - Alkylcarbonyl, C 1 ~C 6 - Alkoxycarbonyl, C 3 ~C 6 -Cycloalkylcarbonyl, R 10 Benzoyl, C, which is monosubstituted or polysubstituted by 1 ~C 6 - Haloalkoxycarbonyl, C 2 ~C 6 - Alkenyloxycarbonyl, carbamoyl, C 1 ~C 6 - Alkylaminocarbonyl (the amino group is R 8 (can be replaced by C) 1 ~C 6 - Alkoxycarbonyl C 1 ~C 6 - Alkylamino (the amino group is R 8 (can be replaced by C) 1 ~C 6 - Alkoxycarbonylamino (the amino group is R 8 (C) (C) 1 ~C 6 -Alkylthio)carbonyl, (C 1 ~C 6 -Alkyl)thiocarbonyl, (C 1 ~C 6 -alkoxy) thiocarbonyl, thiocarbamoyl, C 1 ~C 6 -Alkylamino-thiocarbonyl (the amino group is R 8 (can be replaced by C) 1 ~C 6 - Alkyl sulfonyl, C 1 ~C 6 - Haloalkylsulfonyl, sulfamoyl, C 1 ~C 6 - Alkylaminosulfonyl (the amino group is R 8 (can be replaced by C) 1 ~C 6 -Alkoxycarbonyl-C 1 ~C 6 -Alkyl, aminocarbonyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Alkylaminocarbonyl-C 1 ~C 6 - Alkyl (the amino group is R 8 (can be replaced by C) 3 ~C 6 -Cycloalkylaminocarbonyl-C 1 ~C 6 - Alkyl (the amino group is R 8 (can be replaced by C) 1 ~C 6 -Haloalkylaminocarbonyl-C 1 ~C 6 - Alkyl (the amino group is R 8 (can be replaced by C) 1 ~C 6 -Alkylcarbonyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Haloalkylcarbonyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Alkylcarbonyloxy-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Alkoxycarbonyloxy-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Alkoxycarbonylamino-C 1 ~C 6 - Alkyl (the amino group is R 8 (may be substituted by), hydroxyimino, hydroxyamino-C 1 ~C 6 - Alkyl, C 1 ~C 6 - Alkoxyimino, C 1 ~C 6 -Alkoxyimino-C 1 ~C 6 - Alkyl or C 1 ~C 6 - Haloalkoxyimino - C 1 ~C 6 - Alkyl; R 3 These are halogen, cyano, and C 1 ~C 6 - Alkyl, C 1 ~C 6 - Alkoxy, C 3 ~C 6 - Cycloalkyl, C 1 ~C 6 - Haloalkyl or C 1 ~C 6 - It is a haloalkoxy; R 4 teeth, 【Chemistry 2】 is; or R 5 C 1 ~C 3 - Alkyl sulfonyl amino, C 1 ~C 3 - Haloalkylsulfonylamino or C 3 ~C 6 - It is a cycloalkylsulfonylamino, and any of the amino groups is unsubstituted or R 6 It is substituted by; any of the cycloalkyl groups is R 9 It can be substituted by one or multiple substitutions; R 6 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 3 ~C 6 -Cycloalkyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 - Alkylcarbonyl or C 1 ~C 6 -It is an alkoxycarbonyl; R 8 is hydrogen, halogen, C 1 ~C 3 - Alkyl, C 1 ~C 3 - Alkoxy, C 1 ~C 3 - Haloalkyl or cyano; R 9 is halogen, C 1 ~C 3 - Alkyl, C 1 ~C 3 - Alkoxy, C 1 ~C 3 - is a haloalkyl or cyano; and R 10 is halogen, C 1 ~C 6 - Alkyl, C 1 ~C 6 - Haloalkyl, C 3 ~C 6 - Cycloalkyl, C 3 ~C 6 - Halocycloalkyl, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 - Alkyl, C 3 ~C 6 -Halocycloalkyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 - Alkoxy, C 1 ~C 6 - Haloalkoxy, C 1 ~C 6 - Alkylthio, C 1 ~C 6 - Haloalkylthio, C 1 ~C 6 -Alkyl sulfinyl, C 1 ~C 6 - Haloalkylsulfinyl, C 1 ~C 6 - Alkyl sulfonyl, C 1 ~C 6 - Haloalkylsulfonyl, C 1 ~C 6 -Alkylthio-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Haloalkylthio-C 1 ~C 6 - Alkyl, C 1 ~C 6 - Alkyl sulfonyl oxy, C 1 ~C 6 - Haloalkylsulfonyloxy, phenyl (this is a halogen, C) 1 ~C 6 - Alkyl and C 1 ~C 6 - Can be independently selected from haloalkyls and may be monosubstituted or polysubstituted), phenyl-C 1 ~C 6 -Alkyl,phenyl-C 1 ~C 6 - These are alkoxy, cyano, and nitro compounds. Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, and N-oxides of the compound of formula (I) or of the compound of formula (I).

2. Formulas (I-1), (I-2), (I-3), or (I-4) 【Transformation 3】 (In the formula, A, R 1 , R 2 , R 3 and R 4 (This is as defined in claim 1.) The compound according to claim 1, represented by [the given expression].

3. Formulas (I-1a), (I-2a), (I-3a), or (I-4a) 【Chemistry 4】 (In the formula, R 1 , R 2 , R 3 and R 6 R is as defined in claim 1; 7 (I-1a), (I-2a), (I-3a), and (I-4a) independently of C 1 ~C 3 - Alkyl, C 1 ~C 3 - Haloalkyl or C 3 ~C 6 - Selected from cycloalkyls, the cycloalkyl group is R 9 It can be single-substituted or multi-substituted by R 9 (This is as defined in claim 1.) The compound according to claim 1, represented by [the given expression].

4. The compound according to claim 3, wherein the compound of formula (I) represented by formula (I-1a), (I-2a), (I-3a), or (I-4a) is an enantiomer of (S).

5. R 1 is hydrogen, C 1 ~C 6 - Alkyl, C 1 ~C 6 - Haloalkyl, C 2 ~C 6 - Alkinyl, C 3 ~C 6 -Cycloalkyl, cyano-C 3 ~C 6 - Cycloalkyl, C 3 ~C 6 - Halocycloalkyl, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 - Alkyl, heterocyclyl or C 1 ~C 6 -Alkoxy-C 3 ~C 6 - Cycloalkyl; and R 2 is hydrogen, C 1 ~C 6 - Alkyl, C 1 ~C 6 - Haloalkyl, C 3 ~C 6 - Cycloalkyl, C 3 ~C 6 -Cycloalkyl-C 1 ~C 6 - Alkyl, C 1 ~C 6 -Alkoxy-C 3 ~C 6 - Cycloalkyl, C 1 ~C 6 -Alkoxy-C 1 ~C 6 - Alkyl or C 1 ~C 6 - The compound according to claim 1, wherein it is an alkylcarbonyl.

6. R 1 C 1 ~C 3 - Alkyl, C 1 ~C 3 - Haloalkyl, C 2 ~C 4 - Alkinyl, C 3 ~C 4 - Cycloalkyl, C 3 ~C 4 - Halocycloalkyl, C 3 ~C 4 -Cycloalkyl-C 1 ~C 3 - Alkyl, SO 2 A four-membered heterocyclyl or cyano-C having 3 ~C 4 - Cycloalkyl; and R 2 is hydrogen, C 1 ~C 3 - Alkyl, C 1 ~C 3 - Alkylcarbonyl or C 1 ~C 3 - The compound according to claim 1, which is an alkoxycarbonyl.

7. R 3 is halogen, C 1 ~C 6 - The compound according to claim 1, wherein it is alkyl or cyano.

8. R 3 The compound according to claim 1, wherein is chlorine, bromine, or methyl.

9. R 5 The compound according to claim 1, wherein is isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino, or cyclopropylsulfonylamino.

10. R 6 is hydrogen, C 1 ~C 3 - Alkyl, C 1 ~C 3 -Alkoxy-C 1 ~C 3 - Alkyl, C 3 ~C 4 -Cycloalkyl-C 1 ~C 3 - Alkyl or C 1 ~C 3 - The compound according to claim 1, wherein it is an alkylcarbonyl.

11. The compound according to claim 1, selected from the group consisting of the following. 2-Chloro-N-cyclopropyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,2,2-trifluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-(dichloromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl ]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 2-Chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-[methyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-(difluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-tert-butyl-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-acetyl-2-chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, Methyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl ]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 2-Chloro-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]-N-cyclopropyl-pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-[methyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[2-(trifluoromethylsulfonylamino)ethoxy]pyridine-3-carboxamide, 2-Chloro-N-(5-cyano-3-fluoro-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(5-Chloro-3-fluoro-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(5-chloro-3-methyl-2-pyridyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]-N-(2,4,6-trifluorophenyl)pyridine-3-carboxamide, 2-Chloro-N-(4-cyano-2-fluorophenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,4-difluorophenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2-fluoro-4-methylsulfonylphenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(4-chloro-2-fluorophenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(5-chloro-2-pyridyl)methyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-cyclopropylethyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(3-chloro-2-pyridyl)methyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(2,4-difluorophenyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-isopropyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-ethyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(3,3-difluorocyclobutyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-methyl-N-[1-(5-methyl-1,2,4-oxadiazole-3-yl)ethyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(2,2-difluoroethyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-cyclopropyl-N,2-dimethyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl ]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 5-[(2S)-2-[acetyl(trifluoromethylsulfonyl)amino]propoxy]-2-chloro-N-cyclopropyl-pyridine-3-carboxamide, N-benzyl-2-chloro-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyclopropylethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-[(1-cyanocyclopropyl)methyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclobutyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-ethyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(3-methyltetrahydrofuran-3-yl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-prop-2-inyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-[2-(cyclopropylmethylamino)-2-oxoethyl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,2-difluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-phenyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyano-1-methylethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,2-difluoroethyl)-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(4-fluoro-2-methylphenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-Cyclopropyl-5-[(2S)-2-[Methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-2-methylpyridine-3-carboxamide, N-Cyclopropyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-N-(2,2,2-trifluoroethyl)pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1-cyanocyclopropyl)-N,5-dimethyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(4-ethylthiazole-5-yl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1-cyclopropylethyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[1-(2-ethylthiazole-4-yl)ethyl]-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(3-cyano-2-fluorophenyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Methyl-N-[1-(3-pyridyl)ethyl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-benzyl-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(1-cyanocyclopropyl)-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-5-methylpyridine-4-carboxamide, 5-Methyl-N-(2,2,2-trifluoroethyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Bromo-N-cyclopropyl-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-4-carboxamide, 5-Bromo-N-(1-cyanocyclopropyl)-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-4-carboxamide, 5-Bromo-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Bromo-N-(2,2,2-trifluoroethyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Bromo-N-(1-cyanocyclopropyl)-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Chloro-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 3-Chloro-N-cyclopropyl-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide, 3-Chloro-N-(1-cyanocyclopropyl)-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide, and N-(1-bicyclo[1.1.1]pentanyl)-3-chloro-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide.

12. A compound selected from the group consisting of the following: [(1S)-2-[[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridyl ]oxy]-1-methyl-ethyl]-(trifluoromethylsulfonyl)amino]methyl 2-methylpropanoate, [ [(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl ]oxy]-1-methyl-ethyl]-(trifluoromethylsulfonyl)amino]methyl 2-methylpropanoate, N-[1-[2-(5-cyano-2-pyridyl)-1,2,4-triazole-3-yl]ethyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(2E)-2-methoxyimino-1,1-dimethylethyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-methyl-N-[3-oxo-2-(2,2,2-trifluoroethyl)isoxazolidine-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[1-(4-fluorophenyl)-2-oxo-pyrrolidine-3-yl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(cyclopropylmethoxy)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-[(4S)-2-ethyl-3-oxo-isoxazolidine-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-[3-oxo-2-(2,2,2-trifluoroethyl)isoxazolidine-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1,3-dihydroisobenzofuran-5-ylmethyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-Methyl-N-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidine-3-yl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[2-(2-fluorophenoxy)ethyl]-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-(5-methoxy-1,1-dimethyl-penta-2-inyl)-5-methyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, N-[(4R)-2-ethyl-3-oxo-isoxazolidine-4-yl]-2-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-5-methylpyridine-4-carboxamide, and 5-Bromo-N-[(4R)-2-ethyl-3-oxoisoxazolidine-4-yl]-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide.

13. The compound according to claim 1, selected from the group consisting of the following. 2-Chloro-N-cyclopropyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,2,2-trifluoroethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-(dichloromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, N-acetyl-2-chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, Methyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl ]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 2-Chloro-5-[(2S)-2-[cyanomethyl(trifluoromethylsulfonyl)amino]propoxy]-N-cyclopropyl-pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-[methyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, 2-Chloro-N-(2,4-difluorophenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(1-bicyclo[1.1.1]pentanyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridyl ]oxy]-1-methylethyl]-N-(trifluoromethylsulfonyl)carbamate, 5-[(2S)-2-[acetyl(trifluoromethylsulfonyl)amino]propoxy]-2-chloro-N-cyclopropyl-pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclopropyl)-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyanocyclobutyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(1-cyano-1-methylethyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-N-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(4-fluoro-2-methylphenyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]-N-(2,2,2-trifluoroethyl)pyridine-3-carboxamide, 2-Chloro-N-cyclopropyl-5-[(2S)-2-[methoxymethyl(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, and 5-Bromo-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide.

14. A process for preparing a compound of formula (I) (wherein A is O), wherein the compound of formula (III) (wherein R) is prepared via an intermediate acid chloride of formula (IV) or an activated acylating agent. 1 and R 2 (wherein R is defined in any one of claims 1, 5, or 6) and a compound of formula (II) (wherein R 3 , R 4 A process comprising converting X, Y, and Z (where X, Y, and Z are defined in any one of claims 1 to 10). 【Transformation 5】

15. A composition comprising the compound described in any one of claims 1 to 13, one or more auxiliary agents and diluents, and optionally one or more other active ingredients.

16. A method for controlling and eliminating insects, mites, or mollusks, comprising applying an insecticidal, acaricidal, or molluscicidal amount of a compound of formula I described in any one of claims 1 to 13, or a composition containing the compound, one or more auxiliary agents and diluents, and optionally one or more other active ingredients, to a harmful organism, a habitat of a harmful organism, or a plant susceptible to attack by a harmful organism.

17. A method for protecting plant propagation material from attacks by insects, mites, or mollusks, comprising treating the propagation material or the area in which the propagation material is planted with an effective amount of a compound of formula I as described in any one of claims 1 to 13, or a composition comprising the compound, one or more auxiliary agents and diluents, and optionally one or more other active ingredients.

18. Plant propagation material, such as seeds, comprising, treated with, or attached to, a compound of formula I as described in any one of claims 1 to 13.

19. Use of the compound according to any one of claims 1 to 13 for the manufacture of a pharmaceutical product for controlling parasites in or on animals.

20. Use of the compound according to any one of claims 1 to 13 for manufacturing a pharmaceutical product for controlling ectoparasites on animals, or for preventing and / or treating diseases caused by ectoparasites.

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