Alkoxyheteroaryl-carboxamide or thioamide compounds

Abstract

Compounds of the formula (I) wherein the substituents are as defined in claim 1 and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds can be used as insecticides. # imgabs0 #

Description

[0001] The present invention relates to pesticidal, in particular insecticidal, alkoxyheteroaryl-carboxamide or thioamide compounds, preferably substituted pyridyl, pyrazinyl or pyridazinyl compounds thereof, processes for their preparation, compositions containing these compounds, and their use for controlling animal pests, including arthropods and in particular insects.

[0002] WO 2021153720 describes certain alkoxybenzoic acid amide derivatives.

[0003] Certain new pesticidally active alkoxy and cycloalkoxyheteroaryl-carboxamide or thioamide compounds have now been discovered.

[0004] Therefore, the present invention relates in a first aspect to compounds of formula (I)

[0005]

[0006] in:

[0007] A is O or S;

[0008] X is N or CR 8 ;

[0009] Y is N or CR 8 ;

[0010] Z is N or CR 8 ;

[0011] The premise is that at least one of X, Y, and Z is N;

[0012] R 1is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1- C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl-C1-C6-alkyl, cyano-heterocycloalkyl, hydroxy-C3-C6-cycloalkyl, C1-C6-alkyl-carbonyloxy-C3-C6-cycloalkyl, C1-C6-alkylsulfonyloxy-C3-C6-cycloalkyl C1-C6-alkyl, C1-C6-alkyloxy-C3-C6-cycloalkyl, C1-C6-haloalkoxy-C3-C6-cycloalkyl, C1-C6-alkylthio-C3-C6-cycloalkyl, C1-C6-haloalkylthio-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfonyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfonyl-C3-C6-cycloalkyl, C2-C6-alkynyl-C3-C6-cycloalkyl, C1-C6-alkoxycarbonyl-C3-C6-cycloalkyl, carboxyl-C3-C6-cycloalkyl, carbamoyl-C3-C6-cycloalkyl, C1-C6-alkylaminocarbonyl-C3-C6-cycloalkyl (which may be replaced by R 8 monosubstituted or polysubstituted), C4-C8-bicycloalkyl, C1-C6-alkoxyimino, phenyl (which may be R 10 Monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 Monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C3-C6-cycloalkyl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heterocycloalkyl (which may be R 8 substituted), heterocycloalkyl-C1-C6-alkyl (which may be replaced by R 8 substituted) or heterocycloalkyl-C3-C6-cycloalkyl (the heterocycloalkyl may be R 8 replace);

[0013] R 2is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, phenyl (which may be replaced by R 10 Monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 Monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 monosubstituted or polysubstituted), cyano, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, hydroxy, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-cycloalkylcarbonyl, R 10 Mono- or poly-substituted benzoyl, C1-C6-halogenated alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, carbamoyl, C1-C6-alkylaminocarbonyl (the amino group may be replaced by R 8 Substituted), C1-C6-alkoxycarbonyl C1-C6-alkylamino (the amino group may be R 8 Substituted), C1-C6-alkoxycarbonylamino (the amino group may be R 8 substituted), (C1-C6-alkylthio)carbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, thiocarbamoyl, C1-C6-alkylamino-thiocarbonyl (the amino group may be R 8 substituted), C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, sulfamoyl, C1-C6-alkylaminosulfonyl (the amino group may be R 8 substituted), C1-C6-alkoxycarbonyl-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 Substituted), C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 Substituted), C1-C6-haloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8substituted), C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-haloalkylcarbonyl-C1-C6-alkyl, C1-C6-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonylamino-C1-C6-alkyl (the amino group may be replaced by R 8 substituted), hydroxyimino, hydroxyamino-C1-C6-alkyl, C1-C6-alkoxyimino, C1-C6-alkoxyimino-C1-C6-alkyl or C1-C6-haloalkoxyimino-C1-C6-alkyl;

[0014] R 3 is halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkyl or C1-C6-haloalkoxy;

[0015] R 4 yes

[0016] R 5 is C1-C3-alkylsulfonylamino, C1-C3-haloalkylsulfonylamino, or C3-C6-cycloalkylsulfonylamino, wherein any one of the amino groups is unsubstituted or replaced by R 6 substituted; and wherein any one of the cycloalkyl groups may be R 9 monosubstituted or polysubstituted;

[0017] R 6 is C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl;

[0018] R 8 is hydrogen, halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano;

[0019] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano; and

[0020] R 10is halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6- Alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-haloalkylthio-C1-C6-alkyl, C1-C6-alkylsulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenyl (which may be independently selected from halogen, C1-C6-alkyl and C1-C6-haloalkyl mono- or polysubstituted), phenyl-C1-C6-alkyl, phenyl-C1-C6-alkoxy, cyano or nitro; or

[0021] Agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of compounds of formula (I).

[0022] Compounds of formula (I) with at least one basic center can form acid addition salts, for example, with strong inorganic acids (such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid or hydrohalic acids), strong organic carboxylic acids (such as unsubstituted or, for example, halogen-substituted C1-C4-alkanecarboxylic acids, for example acetic acid, such as saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or such as benzoic acid), or organic sulfonic acids (such as unsubstituted or, for example, halogen-substituted C1-C4-alkanesulfonic acids or arylsulfonic acids, for example methanesulfonic acid or p-toluenesulfonic acid). Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example mineral salts, such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts; or with ammonia or organic amines such as morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethylamine, diethylamine, triethylamine or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example monoethanolamine, diethanolamine or triethanolamine.

[0023] In each case, the compounds of formula (I) according to the invention are in free form, in an oxidized form (such as an N-oxide) or in the form of a salt (for example an agronomically usable salt).

[0024] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton, 1991.

[0025] The compounds of formula (I) according to the invention also include hydrates which may be formed during salt formation.

[0026] As used herein, the term "C1-C n "-alkyl" refers to a saturated straight or branched hydrocarbon radical having 1 to n carbon atoms, attached via any carbon atom, such as any of the following: 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.

[0027] As used herein, the term "C2-C n "-Alkenyl" refers to a straight or branched alkenyl chain moiety having from two to n carbon atoms and one or two double bonds, for example vinyl, prop-1-enyl, but-2-enyl.

[0028] As used herein, the term "C2-C n -alkynyl" refers to a straight or branched alkynyl chain moiety having from two to n carbon atoms and one triple bond, for example ethynyl, prop-2-ynyl, but-3-ynyl,

[0029] As used herein, the term "C3-C n "-cycloalkyl" refers to a 3-membered to n-membered cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0030] As used herein, the term "C1-C n"-alkoxy" refers to a straight-chain or branched saturated alkyl group (as mentioned above) having 1 to n carbon atoms, which is attached via an oxygen atom, i.e., for example, any of the following groups: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy. As used herein, the term "C2-C n "-Alkenyloxy" refers to a straight or branched alkenyl chain (as mentioned above) having 1 to n carbon atoms attached via an oxygen atom.

[0031] As used herein, the term "C1-C n -alkoxy-C1-C n -alkyl" refers to a C1-C n - Alkoxy-substituted alkyl (as mentioned above). Examples are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.

[0032] As used herein, the term "C3-C n -cycloalkyl-C1-C n -alkyl" refers to a C3-C n - cycloalkyl substituted alkyl (as mentioned above). Examples are cyclopropylmethyl, cyclopropylethyl. Similarly, the term "C3-C n -halogenated cycloalkyl-C1-C n "-alkyl" refers to an alkyl group substituted by a cycloalkyl group, wherein the cycloalkyl group is substituted by one or more identical or different halogen atoms. Examples are 3,3-difluorobutylmethyl and 1-chlorocyclopropylmethyl.

[0033] As used herein, the term "heterocycloalkyl" or "heterocyclyl" refers to a stable 3-, 4-, 5- or 6-membered non-aromatic monocyclic group comprising 1, 2 or 3 heteroatoms / groups individually selected from nitrogen, oxygen, sulfur, S=O and SO2. The heterocyclyl group can be bonded to the rest of the molecule via a carbon atom or a heteroatom. Examples of heterocyclyl groups include, but are not limited to, epoxy, aziridinyl, pyrrolinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, tetrahydrothiopyranyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxolane, morpholinyl, oxazinyl, oxetanes, 1,1-dioxothietanes-3-yl, or δ-lactamyl. Heterocycloalkyl groups can be substituted on heteroatoms and / or carbon atoms. The term "cyanoheterocycloalkyl" refers to a carbon atom on a heterocycloalkyl group that is substituted by a cyano group.

[0034] As used herein, the term "heterocycloalkyl-C3-C n -cycloalkyl" refers to a cycloalkyl group (as mentioned above) substituted by a heterocycloalkyl group. n-Cycloalkyl can be substituted on the heterocycloalkyl and / or cycloalkyl groups. Examples are 1-(tetrahydro-3-furyl)cyclopropyl, 1-(tetrahydro-2-furyl)cyclopropyl, 1-(tetrahydro-3-thienyl)cyclopropyl, 1-(3-pyrrolidinyl)cyclopropyl, 1-(tetrahydro-2H-pyran-4-yl)cyclopropyl, 1-(tetrahydro-3-furyl)cyclobutyl, 1- and 1-(tetrahydro-3-furyl)cyclopentanyl.

[0035] As used herein, the term "heterocycloalkyl-C1-C n -alkyl" refers to an alkyl group substituted by a heterocycloalkyl group (as mentioned above). Heterocycloalkyl-C1-C n -Alkyl groups may be substituted on the heterocycloalkyl group and / or the alkyl group. Examples are (tetrahydrofuran-3-yl)methanyl (or (tetrahydrofuran-3-yl)methyl), 1,3-dioxolane-2-methanyl (or 1,3-dioxolane-2-methyl), 2-pyrrolidinomethanyl (or 2-pyrrolidinomethyl) and α-methyl-2-pyrrolidinomethanyl (or α-methyl-2-pyrrolidinomethyl).

[0036] As used herein, the term "cyano-C1-C n -alkyl" refers to a C1-C1-C1-alkyl group having 1 to n carbon atoms n -alkyl (as mentioned above), wherein one of the hydrogen atoms in the group is replaced by a cyano group: for example, cyano-methyl, 2-cyano-ethyl, 2-cyano-propyl, 3-cyano-propyl, 1-(cyano-methyl)-2-ethyl, 1-(methyl)-2-cyano-ethyl, 4-cyanobutyl, etc. Similarly, the term "cyano-C3-C n -cycloalkyl" refers to a C3-C n -cycloalkyl; and the term "cyano-C3-C n -cycloalkyl-C1-C n -alkyl" refers to a cyano-C3-C n -cycloalkyl C1-C n -alkyl.

[0037] Halogen is typically fluorine, chlorine, bromine or iodine. This also applies correspondingly to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy and halocycloalkyl.

[0038] As used herein, the term "C1-C n"-haloalkyl" refers to straight-chain or branched saturated alkyl groups (as mentioned above) having 1 to n carbon atoms, attached via any carbon atom, wherein some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, any of the following: 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- 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl. Accordingly, the term "C1-C2 fluoroalkyl" will refer to a C1-C2 alkyl group with 1, 2, 3, 4 or 5 fluorine atoms, such as any of the following groups: difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl. Similarly, as used herein, the term "C2-C2 fluoroalkyl" will refer to a C1-C2 alkyl group with 1, 2, 3, 4 or 5 fluorine atoms, such as any of the following groups: difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl. n -haloalkenyl" or "C2-C n -haloalkynyl" refers to a C2-C n -alkenyl or C2-C n -alkynyl. Similarly, as used herein, the term "C3-C n -halogenated cycloalkyl" or "C1-C n -haloalkoxy" refers to a C3-C4 substituted by one or more halogen atoms which may be the same or different. n -cycloalkyl or C1-C n -alkoxy.

[0039] As used herein, the term "hydroxy-C3-C n -cycloalkyl" or "carbamoyl-C3-C n The term "-cycloalkyl" refers to a 3-n-membered cycloalkyl group substituted by a hydroxyl group (OH) or a carbamoyl group (NHC(=O)).

[0040] As used herein, the term "C1-C n -alkyl-carbonyloxy-C3-C n -cycloalkyl" refers to an aC(=O)O-partially substituted 3-n-membered cycloalkyl, wherein R a It is C1-C n -alkyl.

[0041] As used herein, the term "carboxyl-C3-C n The term "-cycloalkyl" refers to a 3-n-membered cycloalkyl group substituted by a C(=O)(O)- moiety.

[0042] As used herein, the term "C1-C n -alkoxycarbonyl-C3-C n -cycloalkyl" refers to an c C(=O)-partially substituted 3-n-membered cycloalkyl, wherein R c is C1-C as defined above n -alkoxy. As used herein, the term "C1-C n -alkylsulfonyloxy-C3-C n -cycloalkyl" refers to an a S(O)2O-partially substituted 3-n-membered cycloalkyl, wherein R a It is C1-C n -alkyl.

[0043] As used herein, the term "C1-C n -alkoxy-C3-C n -cycloalkyl" refers to a C1-C n -alkoxy substituted 3-n membered cycloalkyl, similarly, as used herein, the term "C1-C n -haloalkoxy-C3-C n -cycloalkyl" or "C2-C n -alkynyl-C3-C n -cycloalkyl" refers to a C1-C n -haloalkoxy or C2-C n -alkynyl-substituted 3-n-membered cycloalkyl.

[0044] As used herein, the term "C1-C n -alkylthio" or "C1-C n -alkylsulfanyl" refers to a C1-C n -alkyl.

[0045] As used herein, the term "C1-C n -haloalkylthio" or "C1-C n -haloalkylsulfanyl" refers to a C1-C n Halogenated alkyl.

[0046] As used herein, the term "C1-C n -alkylsulfinyl" refers to a C1-C2-alkylsulfinyl group attached through a sulfur atom of a sulfinyl group (or S(=O)-) n alkyl.

[0047] As used herein, the term "C1-C n -alkylsulfonyl" refers to a C1-C2- group attached through the sulfur atom of a sulfonyl group (or S(=O)2-) n alkyl.

[0048] As used herein, the term "C1-C n -alkylsulfonyl-C1-C n -alkyl" refers to a C1-C n Alkylsulfonyl-substituted C1-C n alkyl.

[0049] As used herein, the term "C1-C n -alkylthio-C3-C n -cycloalkyl" refers to a C1-C n -alkylthio (or R a S-) partially substituted 3-n-membered cycloalkyl, wherein R a It is C1-C n -alkyl. Similarly, as used herein, the term "C1-C n -alkylsulfinyl-C3-C n -cycloalkyl" or "C1-C n -alkylsulfonyl-C3-C n -cycloalkyl" refers to C1-C n -alkylsulfinyl (or R a S(O)-) or C1-C n -alkylsulfonyl (or R a S(O)2-) partially substituted 3-n-membered cycloalkyl, wherein R a It is C1-C n -alkyl.

[0050] As used herein, the term "C1-C n -haloalkylthio-C3-C n -cycloalkyl" refers to a C1-C n -haloalkylthio (or R b S-) partially substituted 3-n-membered cycloalkyl, wherein R b It is C1-C n -haloalkyl. Similarly, as used herein, the term "C1-C n -haloalkylsulfinyl-C3-C n -cycloalkyl" or "C1-Cn -haloalkylsulfonyl-C3-C n -cycloalkyl" refers to C1-C n -haloalkylsulfinyl (or R b S(O)-) or C1-C n -haloalkylsulfonyl (or R b S(O)2-) partially substituted 3-n-membered cycloalkyl, wherein R b It is C1-C n -haloalkyl.

[0051] As used herein, the term "C1-C n -haloalkylsulfonylamino" refers to a C1-C n -haloalkylsulfonyl (or R b S(O)2-)(where R b is C1-C as defined above n -haloalkyl).

[0052] As used herein, the term "C1-C n -alkylcarbonyl" refers to a C1-C ... n -alkyl.

[0053] As used herein, the term "C1-C n -alkoxycarbonyl" refers to a C1-C ... n -alkoxy moiety.

[0054] As used herein, the term "C1-C n -alkoxycarbonyl-C1-C6-alkyl" refers to a group replaced by "C1-C n -alkoxycarbonyl substituted C1-C n -alkyl.

[0055] As used herein, the term "benzoyl" refers to a phenyl group attached through the carbon atom of a carbonyl group (C=O).

[0056] As used herein, the term "C1-C n -haloalkoxycarbonyl" refers to a C1-C n -haloalkoxy.

[0057] As used herein, the term "C2-C n -alkenyloxycarbonyl" refers to a C2-C n -alkenyloxycarbonyl.

[0058] As used herein, the term "C1-C n -alkylaminocarbonyl" refers to a C1-C ... n -alkylamino (or R a NHC(=O)-, where R a It is C1-C n -alkyl).

[0059] As used herein, the term "aminocarbonyl-C1-C n -alkyl" refers to a C1-C1-C1-substituted aminocarbonyl (or NH2C(=O)-) n -alkyl.

[0060] As used herein, the term "C1-C n -alkylaminocarbonyl-C1-C n -alkyl" refers to a C1-C n -alkylaminocarbonyl (or R a NHC(=O)-) substituted C1-C n -alkyl, where R a It is C1-C n -alkyl. C1-C n -Alkyl groups may be substituted.

[0061] As used herein, the term "C3-C n -cycloalkylaminocarbonyl-C1-C n -alkyl" refers to a C3-C n -cycloalkylaminocarbonyl (or R d NHC(=O)-) substituted C1-C n -alkyl, where R d It is C3-C n -cycloalkyl. C3-C n -Cycloalkyl groups may be substituted.

[0062] As used herein, the term "C1-C n -haloalkylaminocarbonyl-C1-C n -alkyl" refers to a C1-C n -haloalkylaminocarbonyl (or R b NHC(=O)-) substituted C1-C n -alkyl, where R b It is C1-C n -haloalkyl. C1-C n -Haloalkyl groups may be substituted.

[0063] As used herein, the term "C1-C n-haloalkylcarbonyl-C1-C n -alkyl" refers to a C1-C n -haloalkylcarbonyl (or R b C(=O)-) substituted C1-C n -alkyl, where R b It is C1-C n -haloalkyl.

[0064] As used herein, the term "C1-C n -alkylcarbonyloxy-C1-C n -alkyl" refers to a C1-C n -alkylcarbonyloxy (or R a C1-C substituted with C(=O)O-) group n -alkyl, where R a It is C1-C n -haloalkyl.

[0065] As used herein, the term "C1-C n -alkoxycarbonyloxy-C1-C n -alkyl" refers to a C1-C n -alkoxycarbonyloxy (or R c C1-C substituted with C(=O)O-) group n -alkyl, where R c It is C1-C n -alkoxy. C1-C n -Alkoxy groups may be substituted.

[0066] As used herein, the term "C1-C n -alkylaminocarbonyl-C3-C n -cycloalkyl" refers to a C1-C n -alkylaminocarbonyl (or R a NHC(=O)-group, where R a It is C1-C n -alkyl) substituted C3-C n -cycloalkyl. C1-C n -alkylaminocarbonyl-C3-C n -Cycloalkyl groups may be substituted on the alkyl and / or cycloalkyl groups.

[0067] As used herein, the term "C4-C n"-Bicycloalkyl" refers to a cyclic non-aromatic bicyclic ring system comprising two rings fused together (i.e., sharing two carbon atoms) and consisting solely of carbon and hydrogen 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.

[0068] As used herein, the term "C1-C n "-alkoxyimino" refers to a C1-C2-alkylamino group attached through the nitrogen atom of the imino (N=) moiety n -alkoxy.

[0069] As used herein, the term "hydroxyimino" refers to a hydroxy group attached through the nitrogen atom of the imino (N=) moiety.

[0070] As used herein, the term "hydroxyamino-C1-C n -alkyl" refers to a C1-C ... n -alkyl.

[0071] As used herein, the term "C1-C n -alkoxyimino-C1-C n -alkyl" refers to a C1-C n -C1-C2-alkoxyimino partially substituted n -alkyl.

[0072] As used herein, the term "C1-C n -haloalkoxyimino-C1-C n -alkyl" refers to a C1-C n -C1-C2-alkoxyimino partially substituted n -alkyl, wherein C1-C n -The alkoxy group is substituted by one or more identical or different halogen atoms.

[0073] The term "phenyl-C1-C n -alkyl" refers to a C1-C n -alkyl. Examples include benzyl. Phenyl-C1-C n - The alkyl group may be substituted on the alkyl group and / or the phenyl group.

[0074] The term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic group containing 1, 2, 3 or 4 heteroatoms independently selected from N, O and S. Examples of heteroaryl include, but are not limited to, furyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl or pyridyl. The term "heteroaryl-C1-C n -alkyl" or "heteroaryl-C3-C n -cycloalkyl" refers to a C1-C ... n -alkyl or C3-C n -cycloalkyl. Heteroaryl-C1-C n -alkyl or heteroaryl-C3-C n -Cycloalkyl may optionally be substituted on the heteroaryl, alkyl and / or cycloalkyl groups.

[0075] As used herein, the term "sulfamoyl" refers to an amino (NH2) moiety attached through the sulfur atom of a sulfonyl (SO2) moiety.

[0076] As used herein, the term "C1-C n -alkylaminosulfonyl" refers to a C1-C1-C2-alkylaminosulfonyl group attached through the sulfur atom of the sulfonyl (SO2) moiety. n -alkylamino (or R a NHC(=O)-) moiety, wherein R a It is C1-C n -alkyl).

[0077] As used herein, the term "may be substituted" means that the substituent may or may not carry one or more identical or different substituents, for example, one, two or three R x Substituents. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens may include, but is not limited to, -CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2 or 3 halogens may include, but is not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups. The term "may be substituted" may be used interchangeably with the term "unsubstituted or substituted".

[0078] As used herein, the term "control" refers to reducing the number of pests, eliminating pests, and / or preventing further pest damage, such that damage to plants or to plant-derived products is reduced.

[0079] As used herein, the term "pest" refers to insects and molluscs present in agriculture, horticulture, forestry, storage of products of plant origin (such as fruit, grain and wood); and those pests associated with damage to man-made structures. The term pest covers all stages of the pest life cycle.

[0080] As used herein, the term "effective amount" refers to an amount of a compound or a salt thereof that provides the desired effect upon single or multiple administrations.

[0081] 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.

[0082] An effective amount is readily determined by one skilled in the art by using known techniques and by observing results obtained under similar circumstances. In determining an effective amount, many factors are considered, including, but not limited to: the type of plant or derived product to be applied; the pest to be controlled and its life cycle; the specific compound being applied; the type of application; and other relevant circumstances.

[0083] In one embodiment of the present invention, the compound of formula (I)

[0084]

[0085] in:

[0086] A is O or S;

[0087] X is N or CR 8 ;

[0088] Y is N or CR 8 ;

[0089] Z is N or CR 8 ;

[0090] The premise is that at least one of X, Y, and Z is N;

[0091] R 1is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1- C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl-C1-C6-alkyl, cyano-heterocycloalkyl, hydroxy-C3-C6-cycloalkyl, C1-C6-alkyl-carbonyloxy-C3-C6-cycloalkyl, C1-C6-alkylsulfonyloxy-C3-C6-cycloalkyl C1-C6-alkyl, C1-C6-alkyloxy-C3-C6-cycloalkyl, C1-C6-haloalkoxy-C3-C6-cycloalkyl, C1-C6-alkylthio-C3-C6-cycloalkyl, C1-C6-haloalkylthio-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfonyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfonyl-C3-C6-cycloalkyl, C2-C6-alkynyl-C3-C6-cycloalkyl, C1-C6-alkoxycarbonyl-C3-C6-cycloalkyl, carboxyl-C3-C6-cycloalkyl, carbamoyl-C3-C6-cycloalkyl, C1-C6-alkylaminocarbonyl-C3-C6-cycloalkyl (which may be replaced by R 8 monosubstituted or polysubstituted), C4-C8-bicycloalkyl, C1-C6-alkoxyimino, phenyl (which may be R 10 Monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 Monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C3-C6-cycloalkyl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heterocycloalkyl (which may be R 8 substituted), heterocycloalkyl-C1-C6-alkyl (which may be replaced by R 8 substituted) or heterocycloalkyl-C3-C6-cycloalkyl (the heterocycloalkyl may be R 8 replace);

[0092] R 2is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, phenyl (which may be replaced by R 10 Monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 Monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 Monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 monosubstituted or polysubstituted), cyano, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, hydroxy, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-cycloalkylcarbonyl, R 10 Mono- or poly-substituted benzoyl, C1-C6-halogenated alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, carbamoyl, C1-C6-alkylaminocarbonyl (the amino group may be replaced by R 8 Substituted), C1-C6-alkoxycarbonyl C1-C6-alkylamino (the amino group may be R 8 Substituted), C1-C6-alkoxycarbonylamino (the amino group may be R 8 substituted), (C1-C6-alkylthio)carbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, thiocarbamoyl, C1-C6-alkylamino-thiocarbonyl (the amino group may be R 8 substituted), C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, sulfamoyl, C1-C6-alkylaminosulfonyl (the amino group may be R 8 substituted), C1-C6-alkoxycarbonyl-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 Substituted), C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 Substituted), C1-C6-haloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8substituted), C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-haloalkylcarbonyl-C1-C6-alkyl, C1-C6-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonylamino-C1-C6-alkyl (the amino group may be replaced by R 8 substituted), hydroxyimino, hydroxyamino-C1-C6-alkyl, C1-C6-alkoxyimino, C1-C6-alkoxyimino-C1-C6-alkyl or C1-C6-haloalkoxyimino-C1-C6-alkyl;

[0093] R 3 is halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkyl or C1-C6-haloalkoxy;

[0094] R 4 Is R 5 Monosubstituted or polysubstituted C1-C6-alkyl, or R 5 monosubstituted or polysubstituted C3-C6-cycloalkyl;

[0095] R 5 independently selected from halogen, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkyloxy, C1-C6-haloalkyl, C3-C6-halocycloalkyl, C1-C6-haloalkoxy, C3-C6-halocycloalkyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkylthio, C1-C6-alkylsulfonylamino (the amino group may be R 6 Substituted), C1-C6-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 8 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0096] R 6 independently selected from C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkylcarbonyl and C1-C6-alkoxycarbonyl;

[0097] R 8 independently selected from hydrogen, halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl and cyano;

[0098] R9 independently selected from halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl and cyano;

[0099] and

[0100] R 10 independently selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-halo ... -C6-alkylthio-C1-C6-alkyl, C1-C6-haloalkylthio-C1-C6-alkyl, C1-C6-alkylsulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenyl (which can be independently selected from halogen, C1-C6-alkyl and C1-C6-haloalkyl mono- or poly-substituted), phenyl-C1-C6-alkyl, phenyl-C1-C6-alkoxy, cyano and nitro; or agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compound of formula (I).

[0101] In an embodiment, the compound of formula (I) is represented by formula (I-1), (I-2), (I-3) or (I-4), wherein A, R 1 、R 2 、R 3 and R 4 As defined in the first aspect.

[0102]

[0103] In an embodiment, the compound having formula (I) is represented by formula (I-1a), (I-2a), (I-3a) or (I-4a), wherein R 1 、R 2 、R 3 and R 6 As defined in the first aspect; and R 7 independently from (I-1a), (I-2a), (I-3a) and (I-4a) selected from C1-C6-alkyl, C1-C6-haloalkyl and C3-C6-cycloalkyl (which may be replaced by R 9 mono- or poly-substituted), wherein the methyl group attached to the carbon designated by an asterisk (*) may be in the form of the (S) or (R) enantiomer; or a mixture thereof.

[0104]

[0105]

[0106] In the Examples, the compounds as represented by Formula (I-1a), (I-2a), (I-3a) and (I-4a) are (S) enantiomers.

[0107] Examples according to the present invention are provided as listed below.

[0108] In an embodiment of each aspect of the invention, A is

[0109] A. Oxygen; or

[0110] B. Sulfur.

[0111] In an embodiment of each aspect of the present invention,

[0112] One or two of AX, Y, and Z are N, and the rest are CR 8 ;or

[0113] BX is N, and Z and Y are each CR 8 ;or

[0114] CX and Z are N, and Y is CR 8 ;or

[0115] DX and Y are N, and Z is CR 8 ;or

[0116] EY is N, and X and Z are each CR 8 ;

[0117] FX is N, and Z and Y are each CH; or

[0118] G, X, and Z are N, and Y is CH; or

[0119] H, X, and Y are N, and Z is CH; or

[0120] IY is N, and X and Z are each CH.

[0121] In an embodiment of each aspect of the invention, R 1 yes

[0122] A. hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, heterocyclyl or C1-C6-alkoxy-C3-C6-cycloalkyl; or

[0123] B. hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, cyano-C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered or 5-membered heterocyclyl or C1-C3-alkoxy-C3-C4-cycloalkyl; or

[0124] C. C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, 4-membered heterocyclyl or cyano-C3-C6-cycloalkyl; or

[0125] D. C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl with SO2 or cyano-C3-C4-cycloalkyl; or

[0126] E. Ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietane-3-yl or cyclopropylmethyl.

[0127] In an embodiment of each aspect of the invention, R 2 yes

[0128] A. hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkylcarbonyl; or

[0129] B. hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, C1-C3-alkoxy-C3-C4-cycloalkyl, C1-C3-alkoxy-C1-C3-alkyl or C1-C3-alkylcarbonyl; or

[0130] C. hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl; or

[0131] D. hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl; or

[0132] E. Hydrogen, methyl, acetyl or 2-methylpropionyl.

[0133] In an embodiment of each aspect of the invention, R3 yes

[0134] A. halogen, C1-C6-alkyl or cyano; or

[0135] B. halogen, C1-C3-alkyl or cyano; or

[0136] C. chlorine, methyl or cyano; or

[0137] D. chlorine or bromine; or

[0138] E. Chlorine.

[0139] In an embodiment of each aspect of the invention, R 4 yes

[0140] A. or

[0141] B. or

[0142] C.

[0143] In an embodiment of each aspect of the invention, R 5 yes

[0144] A. C1-C6-alkylsulfonylamino (the amino group may be R 6 Substituted), C1-C6-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replaced); or

[0145] B. C1-C3-alkylsulfonylamino (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) or can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replaced); or

[0146] C. isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino, dichloromethylsulfonylamino or cyclopropylsulfonylamino; or

[0147] D. isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino or cyclopropylsulfonylamino; or

[0148] E. a difluoromethylsulfonylamino group or a trifluoromethylsulfonylamino group.

[0149] In an embodiment of each aspect of the invention, R 6 yes

[0150] A. hydrogen, C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl or C1-C6-alkylcarbonyl; or

[0151] B. hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; or

[0152] C. Hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl.

[0153] In an embodiment of each aspect of the invention, R 7 yes

[0154] A. C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-haloalkyl 9 mono- or polysubstituted C3-C4-cycloalkyl, or

[0155] B. methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl or cyclopropyl; or

[0156] C. methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, dichloromethyl or cyclopropyl; or

[0157] D. Isopropyl, trifluoromethyl, difluoromethyl or cyclopropyl.

[0158] In an embodiment of each aspect of the invention, R 8 yes

[0159] A. hydrogen, halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano; or

[0160] B. hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano; or

[0161] C. Hydrogen.

[0162] In an embodiment of each aspect of the invention, R 9 yes

[0163] A. halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano; or

[0164] B. Chloro, bromo, fluoro, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano.

[0165] In an embodiment of each aspect of the invention, R 10 yes

[0166] A. Halogen, C1-C3-alkyl, C1-C3-haloalkyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, C3-C4-halocycloalkyl-C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkylthio, C1-C3-haloalkylthio, C1-C3-alkylsulfinyl, C1-C3-haloalkylsulfinyl, C1-C3- Alkylsulfonyl, C1-C3-haloalkylsulfonyl, C1-C3-alkylthio-C1-C3-alkyl, C1-C3-haloalkylthio-C1-C3-alkyl, C1-C3-alkylsulfonyloxy, C1-C3-haloalkylsulfonyloxy, phenyl (which may be independently selected from halogen, C1-C6-alkyl and C1-C6-haloalkyl mono- or polysubstituted), phenyl-C1-C3-alkyl, phenyl-C1-C3-alkoxy, cyano or nitro; or

[0167] B. Chloro, bromo, fluoro, methyl, ethyl, isopropyl, methoxy, trifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl or cyano.

[0168] The present invention thus makes available compounds of formula (I) having A, X, Y, Z, R as defined above. 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 and R 10 (in all combinations / permutations).

[0169] Thus, it is possible to obtain, for example, compounds having formula (I) wherein A is embodiment A (ie, A is oxygen); X, Y, and Z are embodiments A (ie, one or two of X, Y, and Z are N, and the rest are CR 8 );R 1 Example B (ie R 1 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, cyano-C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered or 5-membered heterocyclyl or C1-C3-alkoxy-C3-C4-cycloalkyl); R 2 Example C (ie R 2is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl); R 3 Example B (ie R 3 is halogen, C1-C3-alkyl or cyano); R 4 The first aspect (ie R 4 Is R 5 Monosubstituted or polysubstituted C1-C6-alkyl, or R 5 mono- or poly-substituted C3-C6-cycloalkyl); R 5 Example B (ie R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 Replacement); R 6 Example B (ie R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl); and R 9 The first aspect (ie R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano).

[0170] Preferred are compounds of formula (I) wherein

[0171] A is Example A (i.e., A is oxygen);

[0172] X, Y and Z are embodiment A (ie, one or two of X, Y and Z are N, and the rest are CR 8 );

[0173] R 1 Example B (ie R 1 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, cyano-C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered or 5-membered heterocyclyl or C1-C3-alkoxy-C3-C4-cycloalkyl);

[0174] R 2 Example C (ie R 2 is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl);

[0175] R3 Example B (ie R 3 is halogen, C1-C3-alkyl or cyano);

[0176] R 4

[0177] R 5 Example C (ie R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0178] R 6 Example B (ie R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl); and

[0179] R 9 The first aspect (ie R 9 Yes (ie R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano).

[0180] In an embodiment of each aspect of the present invention, a compound of formula (I-1), (I-2), (I-3) or (I-4), wherein

[0181] R 1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, heterocyclyl or C1-C6-alkoxy-C3-C6-cycloalkyl;

[0182] R 2 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkylcarbonyl;

[0183] R 3 is halogen, C1-C6-alkyl or cyano;

[0184] R4 yes

[0185] R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0186] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; and

[0187] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0188] In an embodiment of each aspect of the present invention, a compound of formula (I-1), (I-2), (I-3) or (I-4), wherein

[0189] R 1 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, 4-membered heterocyclyl or cyano-C3-C6-cycloalkyl;

[0190] R 2 is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl;

[0191] R 3 is halogen, C1-C3-alkyl or cyano;

[0192] R 4 yes

[0193] R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0194] R 6is hydrogen, C1-C3-alkyl, C1-C6-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C4-alkyl or C1-C3-alkylcarbonyl; and

[0195] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0196] In an embodiment of each aspect of the present invention, a compound of formula (I-1), (I-2), (I-3) or (I-4), wherein

[0197] R 1 is ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietane-3-yl or cyclopropylmethyl;

[0198] R 2 is hydrogen, methyl, acetyl or 2-methylpropionyl;

[0199] R 3 is chloro, methyl or cyano;

[0200] R 4 yes

[0201] R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0202] R 6 is hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and

[0203] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0204] In an embodiment of each aspect of the present invention, a compound of formula (I-1), (I-2), (I-3) or (I-4), wherein

[0205] R 1is ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietane-3-yl or cyclopropylmethyl;

[0206] R 2 is hydrogen, methyl, acetyl or 2-methylpropionyl;

[0207] R 3 is chlorine, bromine or methyl;

[0208] R 4 yes

[0209] R 5 is a C1-C3-alkylsulfonylamino group (the amino group may be R 6 Substituted), C1-C3-haloalkylsulfonylamino (the amino group may be R 6 replaced) and can be replaced by R 9 Mono- or poly-substituted C3-C6-cycloalkylsulfonylamino (the amino group may be R 6 replace);

[0210] R 6 is hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and

[0211] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0212] In an embodiment of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a) has as R 1 as R 2 as hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkylcarbonyl; as R 3 halogen, C1-C6-alkyl or cyano; as R 6hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; and as R 7 C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-haloalkyl may be replaced by R 9 Mono- or poly-substituted C3-C4-cycloalkyl (wherein R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano).

[0213] In an embodiment of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a) has as R 1 ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietane-3-yl or cyclopropylmethyl; as R 2 hydrogen, methyl, acetyl or 2-methylpropionyl; as R 3 chlorine, bromine or methyl; as R 6 hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and as R 7 C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-haloalkyl may be replaced by R 9 Mono- or poly-substituted C3-C4-cycloalkyl (wherein R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano).

[0214] In an embodiment of each aspect of the present invention, the compound of formula (I-1a), (I-2a), (I-3a) or (I-4a) has as R 1 ethyl, isopropyl, propargyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, cyclopropyl, 1-cyanocyclopropyl, 1-cyanocyclobutyl, 3,3-difluorocyclobutyl, 1,1-dioxothietane-3-yl or cyclopropylmethyl; as R 2 hydrogen, methyl, acetyl or 2-methylpropionyl; as R 3 chlorine, bromine or methyl; as R 6 hydrogen, methyl, methoxymethyl, cyclopropylmethyl or acetyl; and as R 7 C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-haloalkyl may be replaced by R 9 Mono- or poly-substituted C3-C4-cycloalkyl (wherein R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano).

[0215] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I-1),

[0216]

[0217] in

[0218] A is O;

[0219] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0220] R 2 is hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl;

[0221] R 3 It is a halogen;

[0222] R 4 yes

[0223] R 5 is C1-C3-alkylsulfonylamino, C1-C3-haloalkylsulfonylamino, or C3-C6-cycloalkylsulfonylamino, wherein any one of the amino groups is unsubstituted or replaced by R 6 substituted; and wherein any one of the cycloalkyl groups may be R 9 monosubstituted or polysubstituted;

[0224] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; and

[0225] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0226] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I-1a),

[0227]

[0228] in

[0229] R 1is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0230] R 2 is hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl;

[0231] R 3 It is a halogen;

[0232] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl;

[0233] R 7 is C1-C3-alkyl, C1-C3-haloalkyl or can be replaced by R 9 mono- or poly-substituted C3-C4-cycloalkyl; and

[0234] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0235] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I-1a),

[0236]

[0237] in

[0238] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0239] R 2 is hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl;

[0240] R 3 It is a halogen;

[0241] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; R 7is C1-C3-alkyl, C1-C3-haloalkyl or can be replaced by R 9 mono- or poly-substituted C3-C4-cycloalkyl; and

[0242] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano, and

[0243] wherein the compound is the (S) enantiomer.

[0244] In another embodiment of the present invention, the compound of formula (I) is a compound of formula (I-1a),

[0245]

[0246] in

[0247] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0248] R 2 is hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl;

[0249] R 3 is chlorine or bromine;

[0250] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl; R 7 is C1-C3-alkyl, C1-C3-haloalkyl or can be replaced by R 9 mono- or poly-substituted C3-C4-cycloalkyl; and

[0251] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano, and

[0252] wherein the compound is the (S) enantiomer.

[0253] In an embodiment, the compound having formula (I) is represented by formula (I-5a), wherein X, Y, Z, R 1 、R 2 、R 3 and R 6 As defined for compounds of formula (I); and R7 is selected from C1-C6-alkyl, C1-C6-haloalkyl or can be replaced by R 9 Mono- or polysubstituted C3-C6-cycloalkyl.

[0254]

[0255] Preferably, in the compound having formula (I-5a),

[0256] X is N;

[0257] Y and Z are CH;

[0258] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0259] R 3 It is a halogen;

[0260] R 6 is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl;

[0261] R 7 is C1-C3-alkyl, C1-C3-haloalkyl or can be replaced by R 9 mono- or poly-substituted C3-C4-cycloalkyl; and

[0262] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0263] Preferably, in the compound having formula (I-5a),

[0264] X is N;

[0265] Y and Z are CH;

[0266] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0267] R 3 is chlorine, bromine or cyano;

[0268] R 6 It is hydrogen;

[0269] R 7 is C1-C3-alkyl, C1-C3-haloalkyl or can be replaced by R 9 mono- or poly-substituted C3-C4-cycloalkyl; and

[0270] R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano.

[0271] Preferably, in the compound having formula (I-5a),

[0272] X is N;

[0273] Y and Z are CH;

[0274] R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, 4-membered heterocyclyl or cyano-C3-C4-cycloalkyl;

[0275] R 3 is chlorine, bromine or cyano;

[0276] R 6 It is hydrogen;

[0277] R 7 is C1-C3-alkyl, C1-C3-haloalkyl or C3-C4-cycloalkyl.

[0278] 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.

[0279] 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).

[0280] 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, 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]pentyl)-2-chloro- 5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(1S)-2-[[6-chloro-5-[(1-cyanocyclopropyl)carbamoyl]-3-pyridinyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamic acid tert-butyl ester, 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-pyridinyl]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-pyridinyl]oxy ]-1-methyl-ethyl]-(trifluoromethylsulfonyl)amino]methyl 2-methylpropanoate, N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridinyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamic acid methyl ester, 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-pyridinyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(5-chloro-3-fluoro-2-pyridinyl)-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, 2-Chloro-N-(5-chloro-3-methyl-2-pyridinyl)-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]pentyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy] Pyridine-3-carboxamide, N-[1-[2-(5-cyano-2-pyridinyl)-1,2,4-triazol-3-yl]ethyl]-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-[(5-chloro-2-pyridinyl)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)isoxazolidine- 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-carboxamide, N-(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-difluorocyclobutyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide N-(2-(trifluoromethylsulfonyl)amino)propoxy)pyridine-3-carboxamide, N-(2-(2-ethyl)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, N-(2-(cyclopropylmethoxy)-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridinyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, 5-[(2S)-2-[acetyl(trifluoromethylsulfonyl)amino]propoxy]-2-[(2S)-2-(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, tert-butyl N-[(1S)-2-[[6-chloro-5-(cyclopropylcarbamoyl)-3-pyridinyl]oxy]-1-methyl-ethyl]-N-(trifluoromethylsulfonyl)carbamate, tert-butyl 5-[(2S)-2-[acetyl(trifluoromethylsulfonyl)amino]propoxy]-2-[(2S)-2-(trifluoromethylsulfonyl)amino]propoxy]pyridine-3-carboxamide, tert-butyl -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) 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]-2-methyl-pyridine-3-carboxamide, N-cyclopropyl-2-methyl-5-[(2S)-2-(trifluoromethylsulfonylamino)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]pentyl)-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-pent-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-(2,2,2-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 pyridine-4-carboxamide, 5-bromo-N-cyclopropyl-2-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridine-4-carboxamide, 5-bromo-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-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]pentyl)-3-chloro-6-[(2S)-2-(trifluoromethylsulfonylamino)propoxy]pyridazine-4-carboxamide.

[0281] 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.

[0282] In a second aspect, the present invention makes available a composition comprising a compound of formula (I) as defined in the first aspect, one or more adjuvants and diluents, and optionally one or more other active ingredients.

[0283] In a third aspect, the present invention makes available a method for combating and controlling insects, acarids, nematodes or molluscs, which method comprises applying to the pest, the locus of the pest, or a plant susceptible to attack by the pest an insecticidally, acaridically, nematicidally or molluscicidally effective amount of a compound as defined in the first aspect or a composition as defined in the second aspect.

[0284] In a fourth aspect, the present invention makes available a method for protecting plant propagation material from attack by insects, mites, nematodes or molluscs, which method comprises treating the propagation material or the site in which the propagation material is planted with an effective amount of a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect.

[0285] In a fifth aspect, the present invention makes it possible to obtain a plant propagation material, such as a seed, which comprises a compound of formula (I) as defined in the first aspect or a composition as defined in the second aspect, or is treated with said compound or said composition, or has said compound or said composition attached thereto.

[0286] In another aspect, the present invention provides a method for controlling parasites in or on an animal in need thereof, the method comprising administering an effective amount of a compound of the first aspect. The present invention further provides a method for controlling parasites on the body of an animal in need thereof, the method comprising administering an effective amount of a compound of formula (I) as defined in the first aspect. The present invention further provides a method for preventing and / or treating a disease transmitted by parasites on the body, the method comprising administering an effective amount of a compound of formula (I) as defined in the first aspect to an animal in need thereof.

[0287] Compounds of formula (I) can be prepared by those skilled in the art according to known methods. More specifically, compounds of formula I and intermediates can therefore be prepared as described below in the schemes and examples. For the sake of clarity, certain stereocenters are not indicated and are not intended to limit the teachings of these schemes in any way.

[0288] According to the present invention, the compound of formula (I) (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 reacting a compound of formula (II) (wherein R 3 、R 4 , X, Y, Z are as defined for formula (I)) with a compound of formula (III) (wherein R 1 and R 2 This is obtained by converting as defined for formula (I). This is shown in Scheme 1 below:

[0289] Solution 1

[0290]

[0291] As shown in Scheme 1, compound II is activated to a compound of formula IV by methods known to those skilled in the art and described, for example, in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula IV, wherein G is a halogen, is formed by treating a compound of formula II with, for example, oxalyl chloride or thionyl chloride in the presence of a catalytic amount of DMF in an inert solvent such as dichloromethane or THF at a temperature between 25° C. and 170° C., preferably between 25° C. and 80° C. Optionally, the compound is treated with a compound of formula III, wherein R is halogen. 1 and R 2As defined in formula I) treatment of IV produces a compound of formula I. Alternatively, compounds of formula I can be prepared by treating a compound of formula II with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at temperatures between rt and 180° C. to give activated species IV (wherein G is G1 or G2). In addition, acids of formula II can also be activated by reacting with a coupling reagent such as propanephosphonic anhydride. or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (HATU) to provide compounds of formula IV (wherein G is G3 and G4), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt. Chemie 1998, 340, 581. Subsequent reaction with an amine of formula III provides a compound of formula I.

[0292] The compound of formula (II) (wherein R 3 、R 4 , X, Y, Z are as defined for formula (I)) can be obtained by converting a compound of formula (V) (wherein R 3 、R 4 , X, Y, Z are as defined for formula (I) and R 20 This is shown in Scheme 2 below.

[0293] Option 2

[0294]

[0295] As shown in Scheme 2, compound (V) can be subjected to a hydrolysis reaction under alkaline conditions to become compound (II) by methods known to those skilled in the art and described, for example, in ACS Chemical Neuroscience [ACS Chemical Neuroscience] 2017, 2374. For example, the reaction can be in water or 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, compound (V) is converted to compound (II) and can be carried out under acidic conditions by methods known to those skilled in the art and described, for example, in J. Med. Chem. [Journal of Medicinal Chemistry] 1986, 2363. For example, the reaction can be 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).

[0296] A compound of formula (Va) wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is a C1-C6 alkyl group, and R 23 is hydrogen or methyl) can be obtained by reacting a sulfonylating agent having the formula (VII) (wherein R 7 is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cycloalkyl or C1-C6 halocycloalkyl and G is halogen or an activating group of formula G5) and is converted into a compound of formula (VI) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is a C1-C6 alkyl group, and R 23 This is shown in Scheme 3 below.

[0297] Option 3

[0298]

[0299] As shown in Scheme 3, compound (VI) can be converted to compound (Va) by methods known to those skilled in the art and described, for example, in Angew.Chem.Int.Ed. [Applied Chemistry International Edition] 2016, 5299; J.Am.Chem.Soc. [Journal of the American Chemical Society] 2018, 5322; WO 2021153720, WO 2010150192. For example, the 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 known to those skilled in the art, compound (VI) in the form of a salt (such as hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate) can be similarly used to convert to compound (Va).

[0300] The compound of formula (VI) (wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 is a C1-C6 alkyl group, and R 23 is hydrogen or methyl) can be obtained by converting a compound having formula (VIII) wherein R 3 , X, Y, Z are as defined for formula (I), and R 20 and R 21 is a C1-C6 alkyl group, and R 23 This is shown in Scheme 4 below.

[0301] Option 4

[0302]

[0303] As shown in Scheme 4, compound (VIII) can be converted to compound (VI) by methods known to those skilled in the art and described, for example, in WO 2002059117, J. Med. Chem. 2003, 5238, Org. Lett. 2022, 2064. For example, the 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 (VI) can also be obtained and used in the following transformation in the form of its salt (e.g., hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate).

[0304] A compound of formula (VIII) wherein R 3 , X, Y, Z are as defined for formula (I), R 20 and R 21 is a C1-C6 alkyl group, and R 23 is hydrogen or methyl) can be obtained by reacting a compound having the formula (IX) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 is a C1-C6 alkyl group and R 23 is hydrogen or methyl) with an acylating agent having the formula (Xa) (wherein R 21 is C1-C6 alkyl and Q is halogen, hydroxyl or sulfonate group. This is shown in the following scheme 5.

[0305] Option 5

[0306]

[0307] As shown in Scheme 5, compound (IX) can be converted to compound (VIII) by alkylation reaction with Xa (when Q is halogen or sulfonate Q1 or Q2) by methods known to those skilled in the art and described, for example, in Angew. Chem. Int. Ed. [Applied Chemistry International Edition] 2017, 12518; WO 2012101244, WO2004050619, WO 2007072041. For example, the 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 to compound (VIII) by a Mitsunobu reaction with Xa (when Q equals OH) by methods known to those skilled in the art and described, for example, in WO 2012074126; Bioorg. Med. Chem. Lett. 1992, 481, Beilstein J. Org. Chem. 2006, 2, 21. For example, the reaction can be carried out in an organic solvent (such as toluene or THF) in the presence of an azodicarboxylate 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 an aziridine Xb by methods known to those skilled in the art and described, for example, in WO 2007070201. For example, the 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).

[0308] The compound of formula (IX) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 is C1-C6 alkyl) can be obtained by reacting an intermediate compound having the formula (XI) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 is C1-C6 alkyl) converted to have the formula Compounds (wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 is a C1-C6 alkyl group and R 22 is halogen) is obtained in two steps. This is shown in Scheme 6 below.

[0309] Option 6

[0310]

[0311] As shown in Scheme 6, compound (XII) can be converted to compound (XII) by methods known to those skilled in the art as Miyaura borylation and described, for example, in J. Org. Chem., 1995, 7508; J. Org. Chem., 2021, 103. For example, the reaction can be carried out in an organic solvent such as THF or dioxane in the presence of a base such as potassium carbonate or potassium acetate and a palladium catalyst in combination with an appropriate ligand such as 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium. Intermediate (XI) can be converted to a compound having formula (IX) by methods known to those skilled in the art and described, for example, in Tetrahedron Letters 2014, 2082; Tetrahedron Lett. 2017, 3323; Tetrahedron 2005, 1417. For example, the 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.

[0312] Alternatively, a compound of formula (VIII) wherein R 3 , X, Y, Z are as defined for formula (I), R 20 and R 21 is a C1-C6 alkyl group, and R 23 is hydrogen or methyl) can be obtained by reacting a compound having the formula (XII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 20 is a C1-C6 alkyl group, R 22 is a halogen and R 23 is hydrogen or methyl) with a compound of formula (Xa) (wherein R 21 is C1-C6 alkyl and Q is hydroxyl). This is shown in the following scheme 7.

[0313] Option 7

[0314]

[0315] As shown in Scheme 7, compound (XII) can be converted to compound (VIII) by methods known to those skilled in the art and described, for example, in Tetrahedron 1988, 91; J. Am. Chem. Soc. 2010, 11592, WO 2020211836. For example, the 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 2017147700 and J. Med. Chem. 2021, 11570.

[0316] The 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) can be obtained by reacting a compound having formula (Ib) (R 1 、R 2 、R 3 、R 7 , X, Y and Z are as defined for formula (I) and R 23 is hydrogen or methyl) with a compound of formula (XIIa) (wherein R 6 This is obtained by transformation as defined for formula (I) and Q is halogen or sulfonate. This is shown in Scheme 8 below.

[0317] Option 8

[0318]

[0319] As shown in Scheme 8, compound (Ib) can be converted to compound (Ia) by methods known to those skilled in the art and described, for example, in ACS Combinatorial Science 2016, 569; WO202115372. For example, the 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).

[0320] 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 converting a compound having formula (Ic) (R 1 、R2 、R 3 、R 4 , X, Y and Z are as defined for formula (I)). This is shown in Scheme 9 below.

[0321] Option 9

[0322]

[0323] As shown in Scheme 9, compound (Ic) can be converted to compound (Id) by methods known to those skilled in the art and described, for example, in: Org. Lett. 2019, 5848; Tetrahedron Lett. 2008, 4579; WO 2021153720. For example, the reaction can be carried out in an organic solvent such as toluene or chlorobenzene in the presence of a thiating agent such as 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphatane-2,4-dithione (Lawison's reagent).

[0324] 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) can be obtained by reacting a sulfonylating agent having the formula (VII) (wherein R 7 is C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cycloalkyl or C1-C6 halocycloalkyl and G is halogen or an activating group of formula G5) and is converted into 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 is shown in Scheme 9 below. This is shown in Scheme 10 below:

[0325] Plan 10

[0326]

[0327] As shown in Scheme 10, compound (XIII) can be converted to compound (Ic) by methods known to those skilled in the art and described, for example, in Angew.Chem.Int.Ed. [Applied Chemistry International Edition] 2016, 5299; J.Am.Chem.Soc. [Journal of the American Chemical Society] 2018, 5322; WO 2021153720, WO 2010150192. For example, the 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 known to those skilled in the art, compound (XIII) in the form of a salt (such as hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate) can be similarly used to convert to compound (Ic).

[0328] 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) can be obtained by converting a compound having formula (XIV) wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group and R 23 This is shown in Scheme 11 below.

[0329] Plan 11

[0330]

[0331] As shown in Scheme 11, compound (XIV) can be converted to compound (XII) by methods known to those skilled in the art and described, for example, in WO 2002059117, J. Med. Chem. 2003, 5238, Org. Lett. 2022, 2064. For example, the 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 transformations in the form of its salts (e.g., hydrochloride, hydrobromide, trifluoroacetate, p-toluenesulfonate).

[0332] A 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 C1-C6 alkyl) can be obtained by reacting a compound having the formula (XV) (wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I)) with an acylating agent having formula (Xa) (wherein R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl, and Q is halogen, hydroxyl or sulfonate group). This is shown in Scheme 12 below.

[0333] Plan 12

[0334]

[0335] As shown in Scheme 12, compound (XV) can be converted to compound (XIV) by alkylation reaction with Xa (when Q is halogen or sulfonate Q1 or Q2) by methods known to those skilled in the art and described, for example, in Angew. Chem. Int. Ed. [Applied Chemistry International Edition] 2017, 12518; WO 2012101244, WO 2004050619, WO2007072041. For example, the 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 to compound (XIV) by a Mitsunobu reaction with Xa (when Q equals OH) by methods known to those skilled in the art and described, for example, in WO 2012074126; Bioorg. Med. Chem. Lett. 1992, 481, Beilstein J. Org. Chem. 2006, 2, 21. For example, the reaction can be carried out in an organic solvent (such as toluene or THF) in the presence of an azodicarboxylate 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 an aziridine Xb by methods known to those skilled in the art and described, for example, in WO2007070201. For example, the 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).

[0336] According to the present invention, the compound of formula (XV) (wherein R 1 、R 2 、R 3, X, Y and Z are as defined for formula (I)) can be obtained by reacting a compound of formula (XVI) (wherein R 3 , X, Y, Z are as defined for formula (I)) with a compound of formula (III) (wherein R 1 and R 2 This is obtained by converting as defined for formula (I). This is shown in the following Scheme 13:

[0337] Plan 13

[0338]

[0339] As shown in Scheme 13, compound XVI is reacted by a method known to those skilled in the art.

[0340] and activated to a compound of formula XVII, for example, by the method described in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula XVII, wherein G is a halogen, is formed by treating a compound of formula XVI with, for example, 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 between 25° C. and 170° C., preferably between 25° C. and 80° C. Optionally, the compound of formula III, wherein R 1 and R 2 As defined in formula I) treatment of XVII produces a compound of formula I. Alternatively, compounds of formula XV can be prepared by treating a compound of formula XVII with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at temperatures between rt and 180° C. to give the activated species XVII (wherein G is G1 or G2). In addition, acids of formula XVI can also be activated by reacting with a coupling reagent such as propanephosphonic anhydride. or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (HATU) to provide compounds of formula XVII (wherein G is G3 and G4), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt. Chemie 1998, 340, 581. Subsequent reaction with an amine of formula III provides a compound of formula XV.

[0341] The compound of formula (XVI) (wherein R3 , X, Y and Z are as defined for formula (I)) can be obtained by converting a compound of formula (IX) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 20 This is shown in Scheme 14 below.

[0342] Plan 14

[0343]

[0344] As shown in Scheme 14, compound (IX) can be subjected to a hydrolysis reaction under alkaline conditions to become compound (XVI) by methods known to those skilled in the art and described, for example, in ACS Chemical Neuroscience [ACS Chemical Neuroscience] 2017, 2374. For example, the reaction can be in water or 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, compound (IX) is converted to compound (XVI) and can be carried out under acidic conditions by methods known to those skilled in the art and described, for example, in J.Med.Chem. [Journal of Medicinal Chemistry] 1986, 2363. For example, the reaction can be 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).

[0345] Alternatively, a compound of formula (XIV) wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group, and R 23 is hydrogen or methyl) can be obtained by reacting a compound having the formula (XVIII) (wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I), and R 22 is halogen) with a compound having formula (Xa) (wherein R 21 is a C1-C6 alkyl group, R 23 Is hydrogen or methyl, and Q is hydroxyl) to obtain. This is shown in the following scheme 15.

[0346] Plan 15

[0347]

[0348] As shown in Scheme 15, compound (XVIII) can be converted to compound (XIV) by methods known to those skilled in the art and described, for example, in Tetrahedron 1988, 91; J. Am. Chem. Soc. 2010, 11592, WO 2020211836. For example, the 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 2017147700 and J. Med. Chem. 2021, 11570.

[0349] According to the present invention, 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) can be obtained by reacting a compound of formula (XIX) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 22 is halogen) with a compound of formula (III) (wherein R 1 and R 2 This is obtained by converting as defined for formula (I). This is shown in the following scheme 16:

[0350] Plan 16

[0351]

[0352] As shown in Scheme 16, compound XIX is activated to a compound of formula XX by methods known to those skilled in the art and described, for example, in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula XX, wherein G is a halogen, is formed by treating a compound of formula II with, for example, 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 between 25° C. and 170° C., preferably between 25° C. and 80° C. Optionally, the compound is treated with a compound of formula III, wherein R is halogen. 1 and R 2As defined in formula I) treatment of XX produces a compound of formula I. Alternatively, compounds of formula XVIII can be prepared by treating a compound of formula XIX with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent such as pyridine or THF, optionally in the presence of a base such as triethylamine, at temperatures between rt and 180° C. to give activated species IV (wherein G is G1 or G2). In addition, acids of formula XIX can also be activated by reacting with a coupling reagent such as propanephosphonic anhydride. Or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (HATU) to provide compounds of formula XX (wherein G is G3 and G4), as described, for example, in Synthesis [Synthesis] 2013, 45, 1569 and J.l Prakt. Chemie [Practical Chemistry Journal] 1998, 340, 581. Subsequent reaction with an amine of formula III provides a compound of formula XVIII.

[0353] 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 converting a compound of formula (XII) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 22 This is shown in Scheme 17 below.

[0354] Plan 17

[0355]

[0356] As shown in Scheme 17, compound (XII) can be subjected to hydrolysis reaction under alkaline conditions to become compound (XIX) by the method known to those skilled in the art and described, for example, in ACS Chem.Neurosci. [ACS Chemical Neuroscience] 2017,2374. For example, the reaction can be in water or 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, compound (XII) is converted into compound (XIX) and can be carried out under acidic conditions by the method known to those skilled in the art and described, for example, in J.Med.Chem. [Journal of Medicinal Chemistry] 1986,2363. For example, the reaction can be 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).

[0357] A compound of formula (XV) wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I)) can be obtained by reacting the intermediate compound of formula (XXI) (wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I) and R 20 is C1-C6 alkyl) to convert a compound having formula (XVIII) (wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I) and R 22 is halogen) is obtained in two steps. This is shown in Scheme 18 below.

[0358] Plan 18

[0359]

[0360] As shown in Scheme 18, compound (XVIII) can be converted to compound (XXI) by a method known to those skilled in the art as Miyaura borylation and described, for example, in WO 2021076728; J. Med. Chem. 2022, 65, 15433. For example, the reaction can be carried out in an organic solvent (such as THF or dioxane) in the presence of a base (such as potassium carbonate or potassium acetate) and a palladium catalyst in combination with an appropriate ligand (such as 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium). Intermediate (XXI) can be converted into a compound of formula (XV) by methods known to those skilled in the art and described, for example, in WO 2021127071, Tetrahedron Lett. 2014, 2082; Tetrahedron Lett. 2017, 3323; Tetrahedron 2005, 1417. For example, the 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.

[0361] 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 3is cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy) can be converted into 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 This is shown in the following Scheme 19:

[0362] Plan 19

[0363]

[0364] As shown in Scheme 19, compound (If) can be reacted with a compound of formula (XXIIa) (wherein R 24 are C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (Ie) (wherein R 3 is C1-C6-alkoxy and C1-C6-haloalkoxy). For example, the 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. Alternatively, compound (If) can be prepared by methods known to those skilled in the art and described, for example, in WO 2021156787, WO 2020210828, Tetrahedron Lett. [Tetrahedron Express] 2000, 41, 6237 with a compound of formula (XXIIb) (wherein R 3 is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (Ie). For example, the 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 and a suitable ligand (such as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium). Alternatively, compound (If) can be reacted with a cyanide salt (such as potassium ferrocyanide, sodium cyanide, potassium cyanide or zinc cyanide) to form compound (Ie) (wherein R 3is a cyano group). For example, the 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 cuprous iodide, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, copper 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 an additive (such as polyethylene glycol lauryl ether and polymethylhydrogensiloxane).

[0365] A compound of formula (Va) wherein R 4 , X, Y, Z are as defined for formula (I), R 20 is a C1-C6 alkyl group and R 3 is cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy) can be converted into a compound of formula (Vb) (wherein R 4 , X, Y, Z are as defined for formula (I), R 20 is a C1-C6 alkyl group and R 3 This is shown in the following scheme 20:

[0366] Plan 20

[0367]

[0368] As shown in Scheme 20, compound (Vb) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (Va) (wherein R 3 is C1-C6-alkoxy and C1-C6-haloalkoxy). For example, the 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. Alternatively, compound (Vb) can be prepared by methods known to those skilled in the art and described, for example, in WO 2021156787, WO 2020210828, Tetrahedron Letters [Tetrahedron Letters] 2000, 41, 6237 with a compound of formula (XXIIb) (wherein R 3is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (Va). For example, the 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 and a suitable ligand (such as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium). Alternatively, compound (Vb) can be reacted with a cyanide salt (such as potassium ferrocyanide, sodium cyanide, potassium cyanide or zinc cyanide) to form compound (Va) (wherein R is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (Va). For example, the 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 and a suitable ligand (such as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium). Alternatively, compound (Vb) can be reacted with a cyanide salt (such as potassium ferrocyanide, sodium cyanide, potassium cyanide or zinc cyanide) by methods known to those skilled in the art and described, for example, in Adv.Synth.Cat. [Advanced Synthesis and Catalysis] 2017, 359, 2345, US20090062541, Synthesis [Synthesis] (2008), (20), 3351 to form compound (Va) (wherein R 3 is a cyano group). For example, the 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 cuprous iodide, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, copper 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 an additive (such as polyethylene glycol lauryl ether and polymethylhydrogensiloxane).

[0369] Compounds of formula (VIIIa) (wherein X, Y, Z are as defined for formula (I), R 20 is a C1-C6 alkyl group, R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl and R 3 is cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy) can be converted into a compound of formula (VIIIb) (wherein X, Y, Z are as defined for formula (I), R 20 is a C1-C6 alkyl group, R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl and R 3 This is shown in the following Scheme 21:

[0370] Plan 21

[0371]

[0372] As shown in Scheme 21, compound (VIIIb) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (VIIIa) (wherein R 3 is C1-C6-alkoxy and C1-C6-haloalkoxy). For example, the 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. Alternatively, compound (VIIIb) can be prepared by methods known to those skilled in the art and described, for example, in WO 2021156787, WO 2020210828, Tetrahedron Lett. [Tetrahedron Express] 2000, 41, 6237 with a compound of formula (XXIIb) (wherein R 3 is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (VIIIa). For example, the 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 and a suitable ligand (such as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium). Alternatively, compound (VIIIb) can be reacted with a cyanide salt (such as potassium ferrocyanide, sodium cyanide, potassium cyanide or zinc cyanide) to form compound (VIIIa) (wherein R 3 is a cyano group). For example, the 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 cuprous iodide, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, copper 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 an additive (such as polyethylene glycol lauryl ether and polymethylhydrogensiloxane).

[0373] A compound of formula (XIVa) wherein R1 、R 2 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl and R 3 is cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkoxy) can be converted into a compound of formula (XIVb) (wherein R 1 、R 2 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl and R 3 This is shown in the following Scheme 22:

[0374] Plan 22

[0375]

[0376] As shown in Scheme 21, compound (XIVb) can be reacted with a compound of formula (XXIIa) (wherein R 24 is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (XIVa) (wherein R 3 is C1-C6-alkoxy and C1-C6-haloalkoxy). For example, the 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. Alternatively, compound (XIVb) can be prepared by methods known to those skilled in the art and described, for example, in WO 2021156787, WO 2020210828, Tetrahedron Lett. [Tetrahedron Express] 2000, 41, 6237 with a compound of formula (XXIIb) (wherein R 3is C1-C6-alkyl, C3-C6-cycloalkyl and C1-C6-haloalkyl) to form compound (XIVa). For example, the 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 and a suitable ligand (such as [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium). Alternatively, compound (XIVb) can be reacted with a cyanide salt (such as potassium ferrocyanide, sodium cyanide, potassium cyanide or zinc cyanide) to form compound (XIVa) (wherein R 3 is a cyano group). For example, the 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 cuprous iodide, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, copper 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 an additive (such as polyethylene glycol lauryl ether and polymethylhydrogensiloxane).

[0377] The compound of formula (XXIII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group and R 23 is hydrogen or methyl) can be obtained by reacting a compound having the formula (XIX) (wherein R 3 , X, Y, Z are as defined for formula (I) and R 22 is halogen) with a compound having formula (Xa) (wherein R 21 is a C1-C6 alkyl group, R 23 is hydrogen or methyl and Q is hydroxyl). This is shown in Scheme 23 below.

[0378] Plan 23

[0379]

[0380] As shown in Scheme 23, compound (XIX) can be converted to compound (XXIII) by methods known to those skilled in the art and described, for example, in Tetrahedron 1988, 91; J.Am.Chem.Soc. 2010, 11592, WO 2020211836. For example, the reaction can be carried out in the presence of a base (such as sodium hydride, potassium carbonate, cesium carbonate, potassium tert-butoxide, sodium hydroxide, benzyltrimethylammonium hydroxide) in an organic solvent (such as dioxane, dimethylformamide, dimethyl sulfoxide or toluene). Palladium catalysts and appropriate ligands can be used to promote the reaction, as shown in WO2017147700 and J.Med.Chem. 2021, 11570.

[0381] Alternatively, a compound of formula (XIV) wherein R 1 、R 2 、R 3 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group and R 23 is hydrogen or methyl) can be reacted with a compound of formula (XXIII) (wherein R 3 , X, Y, Z are as defined for formula (I), R 21 is a C1-C6 alkyl group and R 23 is hydrogen or methyl) with a compound of formula (III) (wherein R 1 and R 2 This is obtained by converting as defined for formula (I). This is shown in the following scheme 24:

[0382] Plan 24

[0383]

[0384] As shown in Scheme 24, compound (XXIII) is activated to a compound of formula (XXIV) by methods known to those skilled in the art and described, for example, in Tetrahedron 2005, 61(46), 10827-10852. For example, a compound of formula (XXIV) wherein G is a halogen is formed by treating a compound of formula (XXIII) with, for example, 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 between 25° C. and 170° C., preferably between 25° C. and 80° C. Optionally, the compound of formula III wherein R is halogen is treated with oxalyl chloride or thionyl chloride in the presence of a base such as triethylamine or pyridine. 1 and R 2As defined in formula I) treatment of (XXIV) produces a compound of formula (XIV). Alternatively, the compound of formula XIV can be prepared by treating a compound of formula XXIII with dicyclohexylcarbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in an inert solvent (e.g. pyridine or THF), optionally in the presence of a base (e.g. triethylamine) at a temperature between rt and 180° C. to give the activated species XXIV (wherein G is G1 or G2). In addition, the acid of formula XXIII can also be activated by reacting with a coupling reagent such as propanephosphonic anhydride. or O-(7-aza-1-benzotriazolyl)-N,N,N',N'-tetramethyluronium-hexafluorophosphate (HATU) to provide compounds of formula XXIV (wherein G is G3 and G4), as described, for example, in Synthesis 2013, 45, 1569 and J. Prakt. Chem. 1998, 340, 581. Subsequent reaction with an amine of formula III provides a compound of formula XIV.

[0385] Depending on the procedure or reaction conditions, the reactants can be reacted in the presence of a base. Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal amides, alkali metal or alkaline earth metal alkoxides, alkali metal or alkaline earth metal acetates, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal dialkylamides or alkali metal or alkaline earth metal alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxide and carbocyclic amines. Examples that may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

[0386] These reactants can react with each other as is, i.e. without adding solvent or diluent. However, in most cases, it is advantageous to add an inert solvent or diluent or a mixture of these. If the reaction is carried out in the presence of a base, the base (such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline) used in excess can also serve as a solvent or diluent.

[0387] These reactions are advantageously carried out in a temperature range of about -80°C to about +140°C, preferably about -30°C to about +100°C, in many cases in a range between ambient temperature and about +80°C.

[0388] Depending on the reaction conditions and the choice of starting materials, which are appropriate in the respective case, it is possible, for example, to replace only one substituent with another substituent according to the invention in one reaction step, or to replace several substituents with other substituents according to the invention in one and the same reaction step.

[0389] Salts of compounds of formula I can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula I are obtained by treatment with a suitable acid or a suitable ion exchanger reagent, and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.

[0390] Salts of compounds of the formula I can be converted in a customary manner into the free compounds I, acid addition salts (for example by treatment with suitable basic compounds or with suitable ion exchange reagents) and salts with bases (for example by treatment with suitable acids or with suitable ion exchange reagents).

[0391] Salts of compounds of the formula I can be converted into other salts, acid addition salts of compounds of the formula I in a manner known per se, for example into other acid addition salts, for example by treating salts of inorganic acids (such as hydrochlorides) with suitable metal salts of the acid (such as sodium, barium or silver salts, for example with silver acetate) in a suitable solvent in which the inorganic salt formed (such as silver chloride) is insoluble and therefore precipitates from the reaction mixture.

[0392] Depending on the procedure or reaction conditions, those compounds of the formula I which have salt-forming properties can be obtained in free form or in the form of salts.

[0393] Depending on the number of asymmetric carbon atoms present in the molecule, the absolute and relative configuration and / or on the configuration of non-aromatic double bonds present in the molecule, the compounds of the formula I and, where appropriate, their tautomers (in each case in free form or in salt form) can be present in the form of one of the possible isomers or as a mixture of these, for example in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomer mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures; the present invention relates to the pure isomers and also to all possible isomer mixtures, and the above and below are to be understood as such in each case, even if stereochemical details are not explicitly mentioned in each case.

[0394] Diastereomeric mixtures or racemic mixtures of compounds of formula I in free form or in salt form, the acquisition of which may depend on the starting materials and procedures chosen, can be separated in a known manner into the pure diastereomers or racemates on the basis of the physicochemical differences of the components, for example, by fractional crystallization, distillation and / or chromatography.

[0395] Enantiomeric mixtures obtainable in an analogous manner (e.g. racemates) can be resolved into the optical antipodes by known methods, for example by recrystallization from optically active solvents; by chromatography on chiral adsorbents, for example high performance liquid chromatography (HPLC) on acetylcellulose; by cleavage with specific immobilized enzymes with the aid of suitable microorganisms; by formation of inclusion compounds, for example using chiral crown ethers, in which only one enantiomer is complexed; or by conversion into diastereomeric salts, for example by reacting the basic end product racemate with an optically active acid (e.g. a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid) and separating the diastereomeric mixtures obtainable in this way, for example by fractional crystallization on the basis of their different solubilities, thereby obtaining the diastereomers from which the desired enantiomer can be freed by the action of suitable reagents (e.g. a basic reagent).

[0396] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the method according to the invention with starting materials having the appropriate stereochemistry.

[0397] N-oxides can be prepared by reacting a compound of formula I with a suitable oxidizing agent (e.g. H O / urea adduct) in the presence of an anhydride (e.g. trifluoroacetic anhydride). Such oxidations are known from the literature, for example from J. Med. Chem., 32 (12), 2561-73, 1989 or WO 2000 / 15615.

[0398] If the individual components have different biological activities, it is advantageous to isolate or synthesize the biologically more effective isomers, such as enantiomers or diastereomers or isomer mixtures, such as enantiomeric mixtures or diastereomeric mixtures, in each case.

[0399] If appropriate, the compounds of formula I and, where appropriate, their tautomers (in each case in free form or in salt form) can also be obtained in the form of hydrates and / or include other solvents, such as those which can be used for crystallization of compounds present in solid form.

[0400] The compounds of formula (I) according to Tables 1 to 5 below can be prepared according to the methods described above. The following examples are intended to illustrate the present invention and show preferred compounds of formula (I) (in the form of compounds of formula (I-1a), (I-2a), (I-3a), (I-4a) and (I-5a)).

[0401]

[0402]

[0403] Table 1: 1447 compounds of formula (I-1a) are available, wherein the substituent R 1 、R 2 、R 3 、R 6 and R 7 In each of the following lines, specify:

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463]

[0464] Table 2: 396 compounds of formula (I-2a) are available, wherein the substituent R 1 、R 2 、R 3 、R 6 and R 7 In each of the following lines, specify:

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482] Table 3: 133 compounds of formula (I-3a) are available, wherein the substituent R 1 、R 2 、R 3 、R 6 and R 7 In each of the following lines, specify:

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489] Table 4: 282 compounds of formula (I-4a) are available, wherein the substituent R 1 、R 2 、R 3 、R 6 and R 7 In each of the following lines, specify:

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503] Table 5: 54 compounds of formula (I-5a) are available, wherein the substituent R 1 、R 3 , X, Y, and Z are specified on each of the following lines:

[0504]

[0505]

[0506]

[0507] It also makes available certain intermediate compounds, some of which are novel.

[0508] Thus, it is made available herein:

[0509] A. Compounds of formula (II-1), (II-2), (II-3) and (II-4), wherein R 3 、R 6 and R 7 As defined in Tables 1 to 5, respectively.

[0510]

[0511] B. Compounds of formula (IV-1), (IV-2), (IV-3) and (IV-4), wherein R 3 、R 6 and R 7 As defined in Tables 1 to 5, respectively, and wherein G is halogen or G1 to G4.

[0512]

[0513] C. Compounds of formula (V-1), (V-2), (V-3) and (V-4), wherein R 3 、R 6 and R 7 As defined in Tables 1 to 5, and wherein R 20 It is methyl or ethyl.

[0514]

[0515] D. Compounds of formula (VI-1), (VI-2), (VI-3) and (VI-4), wherein R 1 、R 2 and R 3 As defined in Tables 1 to 5, respectively; and wherein R 20 It is methyl or ethyl.

[0516]

[0517]

[0518] E. Compounds of formula (VIII-1), (VIII-2), (VIII-3) and (VIII-4), wherein R 3 As defined in Tables 1 to 5, respectively; and wherein R 20 is methyl and R 21 is methyl or ethyl; or R 20 is ethyl and R 21 It is methyl or ethyl.

[0519]

[0520] F. Compounds of formula (XIII-1), (XIII-2), (XIII-3) and (XIII-4), wherein R 1 、R 2 and R 3 As defined in Tables 1 to 5, respectively.

[0521]

[0522] G. Compounds of formula (XIV-1), (XIV-2), (XIV-3) and (XIV-4), wherein R 1 、R 2 and R 3 As defined in Tables 1 to 5, respectively, and wherein R 21 It is methyl or ethyl.

[0523]

[0524] H. Compounds of formula (XV-1), (XV-2), (XV-3) and (XV-4), wherein R 1 、R 2 and R 3 As defined in Tables 1 to 5.

[0525]

[0526] I. A compound of formula (II-5) wherein X, Y, Z, R 3 、R 6 and R 7 As defined in Table 5.

[0527]

[0528] J. Compounds of formula (IV-5) wherein X, Y, Z, R 3 、R 6 and R 7 like

[0529] as defined in Table 5, and wherein G is halogen or G1 to G4.

[0530]

[0531] K. A compound of formula (V-5) wherein X, Y, Z, R 3 、R 6 and R 7 As defined in Table 5, and where R 20 It is methyl or ethyl.

[0532]

[0533] L. A compound having formula (VI-5) wherein X, Y, Z and R 3 As defined in Table 5, and where R 20 It is methyl or ethyl.

[0534]

[0535] M. A compound having formula (VIII-5) wherein X, Y, Z and R3 As defined in Table 5, and where R 20 is methyl and R 21 is methyl or ethyl; or R 20 is ethyl and R 21 It is methyl or ethyl.

[0536]

[0537] N. A compound of formula (XIII-5) wherein X, Y, Z, R 1 and R 3 As defined in Table 5.

[0538]

[0539] O. A compound of formula (XIV-5) wherein X, Y, Z, R 1 and R 3 As defined in Table 5, and where R 21 It is methyl or ethyl.

[0540]

[0541] The compounds of formula (I) according to the invention are active ingredients of preventive and / or therapeutic value in the field of pest control. Even at low application rates, they have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish, and plants. These active ingredients according to the invention act on all or individual developmental stages of normally sensitive as well as resistant animal pests (such as insects or representatives of the order Acarina). The insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i.e., by destroying the pests immediately or only after a certain period of time (e.g., during molting), or indirectly, for example, by reducing egg laying and / or hatching rates.

[0542] Examples of the animal pests mentioned above are:

[0543] From the order Acarina, e.g.

[0544] 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.;

[0545] From the order Phthirus, e.g.

[0546] Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., and Phylloxera spp.;

[0547] From the order Coleoptera, e.g.

[0548] 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, Hypothenemushampei, 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., Cryptorhynchus spp., Sternechus subsignatus, Tenebrio spp., Tribolium spp., and Trogoderma spp.;

[0549] From the order Diptera, e.g.

[0550] Aedes spp., Anopheles spp., Antherigonas occata, 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., Riveria quadrifasciata, Scatella spp., Sciara spp., Stomoxys spp., Tabanus spp.), tapeworm species (Tannia spp.) and tipula species (Tipula spp.);

[0551] From the order Hemiptera, e.g.

[0552] Acanthocoris scabrator, Acrosternum spp., Adelphocoris lineolatus, Aleurodes spp., Amblypeltanitida, Bathycoelia thalassina, Acanthocoris spp., Clavigralla tomentosicollis, Creontiades spp., Dichelops furcatus, Edessa spp., Euchistus spp., Eurydema pulchrum, Acrosternum spp., Brown-winged stink bug, Horcias nobilellus), rice stink bug species, grass stink bug species, tropical scale bug species, cabbage stink bug (Murgantia histrionic), new long-margined stink bug species, tobacco blind bug (Nesidiocoris tenuis), green stink bug species, Nysius simulans, island stink bug, skin stink bug species, wall stink bug species, red assassin bug species, cocoa stink bug, chestnut stink bug (Scaptocoris castanea), black stink bug species (Scotinophara spp.), Thyanta spp., trypanosoma species, cassava web stink bug (Vatiga illudens);

[0553] Aphids, Adalges, Agalliano ensigera, Agonascenata rgionii, Aleurodicus spp., Aleurocanthus spp., Sugarcane hole whitefly, Aleurothrixus floccosus, Aleyrodes brassicae, Amarascabiguttula, Amritodus atkinsoni, Aphididae, Aphids, Aspidiotus spp., Bactericera cockerelli, Brachycaudus spp., Cabbage aphid, Cavariella aegopodii Scop.), wax scale, brown round scale, net-seed grass leaf scale, Cicadella, Cofana spectra, Cryptomelania, Cicadulina, brown soft scale, corn yellow-winged leafhopper, naked whitefly, citrus psyllid, wheat aphid, western round tail aphid, small green leafhopper, apple aphid, grape leafhopper, wax clam, red eucalyptus psyllid (Glycaspis brimblecombei), cabbage aphid, Hyalopterus, super-tumor aphid species, lemon green leafhopper (Idioscopus clypealis), African leafhopper (Jacobiasca lybica), Laodelphax, ball-hard scale, oyster shield scale, radish aphid (Lopaphis erysimi), Lyogenys maidis, long-tube aphid, foam cicada (Mahanarva spp.), moth wax cicada (Metcalfa pruinosa), wheat aphid, wheat waxhopper (Myndus crudus), aphid spp., Taiwan leek aphid, black-tailed leafhopper spp., brown planthopper (Nilaparvata spp.), pear green aphid, bermudagrass mustard beetle (Odonaspis ruthae), parasitic sugarcane woolly aphid, bayberry whitefly, Caulis psyllid, scutellaria spp., gall aphid spp., corn waxhopper, flat-horned planthopper spp., hopscotch aphid, phylloxera spp., Mosella spp., white-shielded scale spp., mealybug spp., cotton blind bug (Pseudatomoscelis seriatus), psyllid spp., cotton scale (Pulvinaria aethiopica), round-shielded scale spp., Quesada gigas, electric leafhopper (Recilia dorsalis), constrictor aphid spp., black-helmeted scale spp., leafhopper spp., dichotomous aphid spp., wheat aphid (Sitobion spp.)), white-backed planthopper, Spissistilus festinus, Tarophagus Proserpina, aphids, whiteflies, Tridiscus sporoboli, Trionymus spp., African psyllids, orange-headed scale, Zygina flammigera, Zyginidia scutellaris;

[0554] From the order Hymenoptera, e.g.

[0555] Acromyrmex, Arge spp., Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprions spp., Pogonomyrmex spp., imported fire ants, Solenopsis spp., and Vespa spp.

[0556] From the order Isoptera, e.g.

[0557] Coptotermes spp., Corniternes cumulans, Incisitermes spp., Macrotermes spp., Mastotermes spp., Microtermes spp., Reticulitermes spp.; Tropical fire ants (Solenopsis geminate)

[0558] From the order Lepidoptera, for example,

[0559] Species of the genus Long-winged Roller Moth, species of the genus Brown-banded Roller Moth, species of the genus Clearwing Moth, species of the genus Noctua, cotton leafworm, species of the genus Amylois, species of the genus Mucuna, species of the genus Yellow Roller Moth, species of the genus Argyresthia, species of the genus Banded Roller Moth, species of the genus Spodoptera, species of cotton miner, corn armyworm, powdery moth, peach fruit moth, species of the genus Graminus, species of the genus Color Roller Moth, Chrysoteuchia topiaria, grape fruit moth, species of the genus Leaf Roller, species of the genus Cloud Roller, species of the genus Striped Roller Moth, species of the genus Sheath Moth, Colias lesbia, Cosmophila flava), grass borer species, cabbage borer, apple cyclops, boxwood moth, cyclops species, boxwood moth, stem borer species, Sudan cotton bollworm, Spodoptera species, South American corn seedling borer (Elasmopalpus lignosellus), sweet potato stem borer, mealybug species, leaf cyclops species (Epinotia spp.), salt marsh moth (Estigmene acrea), Etiellazinckinella, flower cyclops species, ring needle cyclops, yellow tussock moth species, root cutter species, Feltia jaculiferia, Grapholita spp., clouded broad-winged cyclops, Heliothis species, cabbage borer, leaf cutter species (Herpetogramma spp.), American white moth, tomato borer, Lasmopalpus lignosellus, spiral leafminer, leafminer species, grape flower moth, Loxostege bifidalis, tussock moth species, miner species, Malacosoma spp., cabbage armyworm, tobacco hornworm, Mythimna spp., Noctuidae species, fall moth species, Orniodes indica, European corn borer, super-small tortoise species, brown tortoise species, small-eyed moth, stem borer, red bell moth, coffee leafminer, one-star armyworm, potato moth, cabbage butterfly, Pieris species, diamondback moth, white nest moth species, leaf moth species, mint ash moth (Rachiplusianu), western bean incense (Richia albicosta), white grain borer species (Scirpophaga spp.), Spodoptera species, Cyprinodon species, Spodoptera species, Cotton leaf roller, Cnaphalocrocis species, Heteroptera species, Trichoplusia species, Tomato leafminer, and Lymantria species;

[0560] From the order Mallophaga, for example,

[0561] Damalina spp. and Trichodectes spp.;

[0562] From the order Orthoptera, for example,

[0563] Blatta, Blattella, Mole Cricket, Madeira Cockroach, Locust, American Mole Cricket (Neocurtillahexadactyla), Periplaneta, Mole Cricket (Scapteriscus spp), and Desert Locust;

[0564] From the order Psocoptera, for example,

[0565] Liposcelis spp.;

[0566] From the order Siphonaptera, for example,

[0567] Ceratophyllus spp., Ctenocephalides spp., and Xenopsylla cheopis;

[0568] From the order Thysanoptera, for example,

[0569] Calliothrips phaseoli, Frankliniella spp., Heliothrips spp., Hercinothrips spp., Parthenothrips spp., Scirtothrips aurantii, Sericothrips variabilis, Taeniothrips spp., Thrips spp.

[0570] From the order of the Thysanura, for example, Lepisma saccharina.

[0571] In a further aspect, the present invention may also relate to a method for controlling damage to plants and parts thereof by plant-parasitic nematodes (endoparasitic nematodes, semi-endoparasitic nematodes and ectoparasitic nematodes), in particular the following plant-parasitic nematodes, such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other species of Meloidogyne; cyst-forming nematodes, Globodera rostochiensis and other species of Globodera; Heterodera avenae, Heteroderaglycines, Heterodera exigua and other species of Globodera; schachtii), Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus, and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ring nematodes, nematodes), Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stemand bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci, and other Ditylenchus species; Awl nematodes, Dolichodorus species;Spiral nematodes, Heliocotylenchus multicinctus, and other species of the genus Helicotylenchus; Sheath and sheathoid nematodes, species of the genera Hemicycliophora, and species of the genera Hemicriconemoides; Hirshmanniella species; Lancenematodes, species of the genus Hoploaimus; False rootknot nematodes, species of the genus Nacobbus; Needle nematodes, Longidoruse longatus, and other species of the genus Longidorus; Pin nematodes, species of the genus Pratylenchus; Lesion nematodes. nematodes), Pratylenchus negletus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi, and other Pratylenchus species; Burrowing nematodes, Radopholus similis, and other Radopholus species; Reniform nematodes, Rotylenchus robustus, Rotylenchus reniformis, and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus) and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other Tylenchorhynchus species;Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant-parasitic nematode species, such as Subanguina spp., Hypsoperine spp., Macroposthonia spp., Melinius spp., Punctodera spp., and Quinisulcius spp.

[0572] The compounds of the present invention may also have activity against molluscs. Examples include, for example, the Pomacea family; the Arion family (A. ater, A. circumscriptus, A. hortensis, A. rufus); the Bradybaenidae family (Bradybaenidae, A. rufus); fruticum); Cepaea (Cepaea hortensis, C. nemoralis); Ochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (Galba trunculata); Helicelia (H. itala, H. obvia); Helicidae (Helicigon) aarbustorum; 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.

[0573] The active ingredients according to the invention can be used for controlling, i.e. suppressing or destroying harmful organisms of the above-mentioned type, which occur in particular on plants, especially on useful and ornamental plants in agriculture, horticulture and forestry, or on organs of such plants, such as fruits, flowers, leaves, stems, tubers or roots, and in some cases even plant organs formed at a later point in time still remain protected against these harmful organisms.

[0574] In particular, suitable target crops are cereals, such as wheat, barley, rye, oats, rice, maize or sorghum; beets, such as sugar beets or fodder beets; fruits, such as pome fruits, stone fruits or soft fruits, such as apples, pears, plums, peaches, apricots, cherries or berries (e.g. strawberries, raspberries or blackberries); leguminous crops, such as beans, lentils, peas or soybeans; oilseed crops, such as rapeseed, mustard, poppy, olives, sunflower, coconut, castor, cocoa, beans or peanuts; cucurbits such as pumpkin, cucumber, or melon; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; lauraceae such as avocado, cinnamon, or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, plantago, and latex plants.

[0575] In particular embodiments, compounds of formula (I) can control mites, rust mites and spider mites in crops, trees and plants selected from vegetables (especially tomatoes and cucurbits), citrus, pome fruits, stone fruits, nuts, cotton, tropical crops, avocados, ornamentals, beans, soybeans, strawberries and grapes.

[0576] The compositions and / or methods of the present invention may also be used on any ornamental and / or vegetable crop, including flowers, shrubs, broadleaf trees, and evergreen plants.

[0577] For example, the present invention can be used with any of the following ornamental plant species: Ageratum species, Alonsoa species, Anemone species, Anisodontea capsenisis, Anthemis species, Antirrhinum species, Aster species, Begonia species (e.g., Rieger Begonia, Begonia sempervirens, Begonia tubéreux), Bougainvillea species, Brachycome species, Brassica species (ornamentals), Calceolaria species, Capsicum, Catharanthus roseus, Canna species, Centaurea species, Chrysanthemum species, Cineraria species (C. maritime), Coreopsis species, Crassula coccinea, Cupheaignea, Dahlia species, Delphinium species, Dicentra species, Dorotheantus species. spp.), Lisianthus, Forsythia species, Fuchsia species, Geranium gnaphalium, Gerbera species, Globe amaranth, Heliotrope species, Sunflower species, Hibiscus species, Hydrangea species, Hydrangea species, Rhododendron, Impatiens species (African balsam), Amaranth species (Iresines spp.), Kalanchoe species, Lantana, March flower, Lion's ear, Lilium species, Mesembryanthemum species, Physalis species, Monarda species, Dracaena species, Marigold species, Dianthus species (carnation), Canna species, Oxalis species, Daisy species, Pelargonium species (Shieldleaf Pelargonium, Horseshoe Pelargonium), Viola species (Viola tricolor), Petunia species, Phlox species, Plecthranthus species spp.), poinsettia species, creeper species (five-leaf creeper, Parthenocissus quinquefolia), primula species, ranunculus species, azalea species, Rosa species (roses), rudbeckia species, African violet species, salvia species, Scaevola aemola, Schizanthus wisetonensis, sedum species, Solanum species, Surfinia petunia species (Surfinia spp.), marigold species, Nicotiana species, verbena species, zinnia species, and other bedding plants.

[0578] For example, the present invention can be used with any of the following vegetable species: Allium (garlic, onion, shallot (A.oschaninii), leek, shallot, scallion), beaked parsley, celery, asparagus, beets, Brassica (cabbage, Chinese cabbage, turnip), peppers, chickpeas, endive, chicory (chicory, endive), watermelon, Cucurbita (cucumber, cantaloupe), Cucurbita (zucchini, Indian pumpkin), Cynara (artichoke, cardoon), carrot, fennel, Hypericum, lettuce, Lycopersicon (tomato, cherry tomato), mint, basil, parsley, Phaseolus (bean, pea), pea, radish, rhubarb, rosemary, sage, black salsify, eggplant, spinach, Valerian (V. eriocarpa), and broad beans.

[0579] Preferred ornamental plant species include African violet, begonia, dahlia, gerbera, hydrangea, verbena, rose, kalanchoe, poinsettia, aster, cornflower, coreopsis, delphinium, monarda, phlox, rudbeckia, sedum, petunia, violet, impatiens, geranium, chrysanthemum, ranunculus, fuchsia, salvia, hydrangea, rosemary, sage, St. John's wort, mint, sweet pepper, tomato, and cucumber.

[0580] The compounds of formula (I) may be particularly suitable for controlling: mites, spider mites and rust mites, for example, species of the genus Acarus; species of the genus Wu; rough-legged flour mite; Acarus species; citrus gall mite; citrus thorny tick; Acarus species; strychnidactylus striata; strychnidactylus species; pseudo-amymphosae; short-palpated mite; purple short-palpated mite; lucerne moss mite; fruit moss mite; wood-loving mite species; chela mites; chela mites; chela mites; yasiger mites; cattle itch mite; Demodex species; cynomys species; bovine Demodex; Demodex species. caballi; Demodex canis; Demodex goat; Demodex equi; Demodex ovis; Demodex spp.; Demodex suis; Dermanysus gallinae; Dermanysus spp.; Eotetranychus spp.; Eotetranychus wei; Pear gall mite; Ribes chinensis gall mite; Eotetranychus spp.; Grape gall mite; Tetranychus spp.; Halotydeus destructor; Hemithorax spp.; Sarcoptes spp.; Chicken chick mite; Yak mite; Sarcoptes spp.; Neoschongastia xerothermobia; Neotrombicula autumnalis; Neotrombicula desaleri; Cat ear mite; Otomitus spp.; Coffee mite; Holly mite ilicis); Micrognathus species; Chelicerata species; Cystoma spp.; Cystoma spp.; Cystoma spp.; Woodfowl spp.; Dog ear scabies; Otodactylus species; Panonychus citrus; Panonychus species; Apple spp.; Citrus rust; Psoralea species; Phytoseiidae species; Pneumonyssoides caninum; Polyphagous tarsonemus; Polyphagous tarsonemus species; Psorergates ovis; Psorergates species; Rabbit itch mites; Horse itch mites; Sheep itch mites; Psorergates species; Psorergates species; Psorergates ovis; Psorergates species; Psorergates equine; Psorergates ovis; Psorergates species; Psorergates spp. ... rupicaprae); Sarcoptes species; Sarcoptes suis; Scabies scabiei; Scabies scabiei species; Scabies scabiei species; Tarsonemus species; Tetranychus cinnabarinus; Tetranychus kanzawa; Tetranychus species; Tetranychus urticae; Tetranychus urticae; Chigger mites; Tylops scabiei species; Varroa jacobsoni; Varroa species; Vasates lycopersici; and Zetzellia mali.

[0581] In embodiments, compounds of formula (I) may control one or more of: citrus gall mite; tomato needle-spinning gall mite (Aculus lycopersici); Peet's needle-spinning gall mite; Steinni's needle-spinning gall mite; purple-red short-palped mite; short-palped mite species; fruit moss mite; hornbeam spider mite; Eriophyes species; pear gall mite; Eriophyes piri; Eriophyes species; grape gall mite; African true spider mite; oriental true spider mite; small clawed mites in grasslands; citrus rust mite; apple rust mite; grape rust mite; citrus rue rust mite; polyphagous tarsoneme; cinnabarinus spider mite; Kanzawa's spider mite; Tetranychus species; and two-spotted spider mite.

[0582] In another embodiment, the compounds of formula (I) may be particularly useful for controlling one or more of: Citrus Gall Mite; Pitt's Needle Gall Mite; Purple-Palcipedulous Mite; Brevipalpus spp.; Eriophyes piri; Grape Gall Mite; African True Spider Mite; Oriental True Spider Mite; Small Clawed Mite; Apple Panonychus; Grape Rust Mite; Citrus Rust Mite; Lateral Polyphagous Tarsoneme; Cinnabarinus Tetranychus; Kanzawa's Tetranychus; Tetranychus spp.; and Two-spotted Tetranychus.

[0583] The term "crops" is to be understood as also including crop plants which have been transformed by the use of recombinant DNA techniques so as to enable them to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular those of the genus Bacillus.

[0584] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, such as those from Bacillus cereus or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), such as Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of bacterial colonizing nematodes, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophila, or Xenorhabdus spp. nematophilus); toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinin; protease inhibitors, such as trypsin inhibitor, silk proteinase inhibitor, potato glycoprotein, cystatin, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, maize-RIP, abrin, luffain, saporin or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysteroid inhibitors, HMG-COA-reductase, ion channel blockers, such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0585] In the context of the present invention, δ-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3, or Vip3A) are understood to include, but are not limited to, mixed toxins, truncated toxins, and modified toxins. Mixed toxins are recombinantly produced by combining different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of a naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that a non-naturally occurring protease recognition sequence be inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0586] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0587] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0588] The toxins contained in the transgenic plants confer tolerance to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0589] Transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: (Zea mays variety expressing Cry1Ab toxin); YieldGard (maize variety expressing Cry3Bb1 toxin); YieldGard (Zea mays varieties expressing Cry1Ab and Cry3Bb1 toxins); (Zea mays variety expressing Cry9C toxin); Herculex (a maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate-ammonium); NuCOTN (cotton variety expressing Cry1Ac toxin); Bollgard (cotton variety expressing Cry1Ac toxin); Bollgard (cotton varieties expressing Cry1Ac and Cry2Ab toxins); (cotton variety expressing Vip3A and Cry1Ab toxins); (potato variety expressing Cry3A toxin); GT Advantage (GA21 glyphosate tolerance trait), CB Advantage (Bt11 corn borer (CB) trait) and

[0590] Further examples of such genetically modified crops are:

[0591] 1. Bt11 maize, from Syngenta Seeds SAS, Cheminde l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenicly expresses the PAT enzyme to confer tolerance to the herbicide glufosinate-ammonium.

[0592] 2. Bt176 maize, from Syngenta Seeds, 27 Rue de Hobbitt, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. This genetically modified maize is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of the toxin Cry1Ab. Bt176 maize also transgenicly expresses the enzyme PAT to confer tolerance to the herbicide glufosinate-ammonium.

[0593] 3. MIR604 maize, from Syngenta Seeds, 27 Rue de Hobbit, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. This maize plant is rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055, modified by insertion of a cathepsin-G protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0594] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain coleopteran insects.

[0595] 5. IPC 531 cotton, from Monsanto Europe SA, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0596] 6.1507 maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate.

[0597] 7. NK603×MON 810 maize, from Monsanto Europe, 270-272 Boulevard Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. This is a conventionally bred hybrid maize variety, constructed by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, conferring herbicide tolerance. (contains glyphosate), and also the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstakia, which confers resistance to certain lepidopteran insects, including the European corn borer.

[0598] Transgenic crops of insect-resistant plants are also described in the BATS (Zentrum für Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) report 2003 ( http: / / bats.ch )middle.

[0599] The term "crop" should be understood to also include crop plants that have been transformed using recombinant DNA technology so that they can synthesize antipathogenic substances with selective action, such as, for example, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants that can synthesize such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above.

[0600] Crops can also be modified to enhance resistance to fungal (eg, Fusarium, Anthracnose, or Phytophthora), bacterial (eg, Pseudomonas), or viral (eg, Potato Leaf Roll Virus, Tomato Spotted Wilt Virus, Cucumber Mosaic Virus) pathogens.

[0601] Crops also include those with enhanced resistance to nematodes, such as Heterodera glycines.

[0602] Crops with tolerance to abiotic stress include those with increased tolerance to drought, high salinity, high temperature, cold, frost or light radiation, for example, through expression of NF-YB or other proteins known in the art.

[0603] Antipathogenic substances that can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers of sodium channels and calcium channels, for example viral KP1, KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; so-called "pathogenesis-related proteins" (PRPs; see, for example, EP-A-0 392 225); antipathogenic substances produced by microorganisms, such as peptide antibiotics or heterocyclic antibiotics (see, for example, WO 95 / 33818) or proteins or polypeptide factors which are involved in plant defense against pathogens (so-called "plant disease resistance genes", as described in WO 03 / 000906).

[0604] Further areas of use of the compositions according to the invention are the protection of stored goods and storage rooms and the protection of raw materials such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, in particular the protection of humans, domestic animals and productive livestock from pests of the types mentioned.

[0605] The present invention provides a compound of the first aspect for use in therapy. The present invention provides a compound of the first aspect for use in controlling parasites in or on an animal. The present invention further provides a compound of the first aspect for use in controlling parasites on the body of an animal. The present invention further provides a compound of the first aspect for use in preventing and / or treating a disease transmitted by parasites on the body.

[0606] The present invention provides the use of the compound of the first aspect for the manufacture of a medicament for controlling parasites in or on the body of an animal. The present invention further provides the use of the compound of the first aspect for the manufacture of a medicament for controlling parasites on the body of an animal. The present invention further provides the use of the compound of the first aspect for the manufacture of a medicament for preventing and / or treating diseases transmitted by parasites on the body.

[0607] The present invention provides a use of the compound of the first aspect in controlling parasites in or on the body of an animal. The present invention further provides a use of the compound of the first aspect in controlling parasites on the body of an animal.

[0608] When used in the context of parasites in or on animals, the term "control" means reducing the number of pests or parasites, eliminating pests or parasites and / or preventing further infestation by pests or parasites.

[0609] When used in the context of parasites in or on animals, the term "treat" means to inhibit, slow, halt or reverse the progression or severity of existing symptoms or disease.

[0610] The term "prevent" when used in the context of parasites in or on animals means avoiding the development of symptoms or disease in the animal.

[0611] When used in the context of parasites in or on animals, the term "animal" may refer to both mammals and non-mammals, such as birds or fish. In the case of a mammal, it can be a human or a non-human mammal. Non-human mammals include, but are not limited to, livestock animals and pets. Livestock animals include, but are not limited to, cattle, camels, pigs, sheep, goats, and horses. Pets include, but are not limited to, dogs, cats, and rabbits.

[0612] A "parasite" is a harmful organism that lives in or on a host animal and benefits by obtaining nutrients at the host animal's expense. An "endoparasite" is a parasite that lives inside the host animal. An "ectoparasite" is a parasite that lives on the host animal's body. ectoparasites include, but are not limited to, ticks, insects, and crustaceans (e.g., sea lice). The subclass Ixodida (or Acarina) includes ticks and mites. Ticks include, but are not limited to, members of the genera Rhipicaphalus, such as Rhipicaphalus microplus (Boophilus microplus) and Rhipicephalus sanguineus; Amblyomrna; Dermacentor; Haemaphysalis; Hyalomma; Ixodes; Rhipicentor; Margaropus; Argas; Otobius; and Ornithodoros. Mites include, but are not limited to, members of the genera: Dermestes, such as Dermestes gallinae; Psoralea, such as Psoralea goatii; Cheyletus; Dermatophytes; such as Dermatophytes gallinae; Ortnithonyssus; Demodex, such as Demodex canis; Sarcophagida, such as Sarcophagidae; and Psoralea. Insects include, but are not limited to, members of the orders: Siphonaptera, Diptera, Trichoderma, Lepidoptera, Coleoptera, and Homoptera. Members of Siphonaptera include, but are not limited to, Ctenocephatides cati and Ctenocephatides canis. Members of Diptera include, but are not limited to, species of the genus Musca; skin flies, such as horse flies and sheep flies; biting flies; horseflies, such as species of the genus Tabunus and species of Tabunus; black horn flies, such as blood flies; biting flies; green flies; midges; and mosquitoes. Members of the order Trichoderma include, but are not limited to, blood-sucking lice and chewing lice, such as the wool louse (Bovicola Ovis) and the bovine feather louse.

[0613] The term "effective amount," when used in the context of parasites in or on an animal, refers to an amount or dosage of a compound of the invention, or a salt thereof, which, when administered to an animal in a single dose or multiple doses, provides the desired effect in or on the animal. An effective amount can be readily determined by the attending diagnostician (as one skilled in the art) by using known techniques and by observing results obtained in similar situations. In determining an effective amount, the attending diagnostician considers a number of factors, including, but not limited to: the species of mammal; its size, age, and general health; the parasite to be controlled and the degree of infestation; the specific disease or condition involved; the extent or severity of the disease or condition; the individual's response; the specific compound to be administered; the mode of administration; the bioavailability characteristics of the administered formulation; the dosage regimen selected; the use of concomitant medications; and other relevant circumstances.

[0614] The compounds of the present invention can be given to animals by any route with the desired effect, including but not limited to topical, oral, parenteral and subcutaneous. Topical application is preferred. Preparations suitable for topical application include, for example, solutions, emulsions and suspensions, and can be poured, dotted, sprayed, sprayed, or immersed in the form of a spray race. In an alternative, the compounds of the present invention can be administered by ear tags or collars.

[0615] Salt forms of the compounds of the present invention include both pharmaceutically acceptable salts and veterinarily acceptable salts, which may be different from agrochemically acceptable salts. Pharmaceutically and veterinarily acceptable salts and common methods for preparing them are well known in the art. See, for example, Gould, PL, "Salt selection for basic drugs", International Journal of Pharmaceutics, 33:201-217 (1986); Bastin, RJ et al. "Salt Selection and Optimization Procedures for Pharmaceutical New Chemical Entities", Organic Process Research and Development, 4:427-435 (2000); and Berge, SM et al., "Pharmaceutical Salts", Journal of Pharmaceutical Sciences, 66:1-19, (1977). It will be appreciated by those skilled in the art that the compound of the present invention easily changes into salt using technology and conditions known to those of ordinary skill in the art, and can be used as salt (such as hydrochloride) to separate.In addition, it will be appreciated by those skilled in the art that the compound of the present invention easily changes into corresponding free alkali, and can be used as corresponding free alkali to separate from corresponding salt.

[0616] The present invention may also provide methods for controlling pests (such as mosquitoes and other disease vectors; see also http: / / www.who.int / malaria / vector_control / irs / en / ). In one embodiment, the method for controlling pests comprises applying the composition of the present invention to the target pests, their locus, or a surface or substrate by painting, rolling, spraying, coating, or dipping. By way of example, IRS (indoor residual spraying) application to surfaces (such as walls, ceilings, or floor surfaces) is contemplated by the methods of the present invention. In another embodiment, application of such compositions to substrates such as nonwoven or fabric materials in the form of netting, coverings, bedding, curtains, and tents (or which may be used in the manufacture of such articles) is contemplated.

[0617] In one embodiment, the method for controlling this type of harmful organism comprises applying the composition of the present invention of pesticidal effective dose to target harmful organism, their place or surface or substrate, so that on this surface or substrate, effective retained pesticidal activity is provided.This application can be carried out by brushing, rolling, spraying, coating or dipping pesticidal composition of the present invention.By way of example, the IRS application of surface (such as wall, ceiling or floor surface) is considered by the method of the present invention, so that effective retained pesticidal activity is provided on this surface.In another embodiment, it is considered to use this type of composition for the residual control of the harmful organism on substrate, and this substrate is as the fabric material in the form of netting, covering, bedding, curtain and tent (or can be used in the manufacture of these articles).

[0618] The substrate to be treated (including nonwovens, fabrics or nettings) can be made of natural fibers (such as cotton, raffia, jute, flax, sisal, burlap or wool) or synthetic fibers (such as polyamide, polyester, polypropylene, polyacrylonitrile, etc.). Polyester is particularly suitable. Methods for treating textiles are known, for example WO 2008 / 151984, WO 2003 / 034823, US 5631072, WO 2005 / 64072, WO 2006 / 128870, EP 1724392, WO 2005113886 or WO 2007 / 090739.

[0619] A further area of ​​use of the compositions according to the invention may be the field of tree injection / trunk treatment for all ornamental trees as well as all kinds of fruit and nut trees.

[0620] In the field of tree injection / trunk treatment, the compounds according to the invention may be particularly suitable for combating wood-boring insects from the orders Lepidoptera and from the orders Coleoptera mentioned above, in particular against the wood-boring insects listed in the following Tables A and B:

[0621] Table A. Examples of economically important exotic wood-boring insects.

[0622]

[0623] Table B. Examples of economically important native wood-boring insects.

[0624]

[0625]

[0626]

[0627]

[0628]

[0629] The present invention can also be used to control any insect pest that may be present in turfgrass, including, for example, beetles, caterpillars, fire ants, ground pearls, millipedes, woodlice, mites, mole crickets, scale insects, mealybugs, ticks, cicadas, southern wheat stink bugs, and white grubs. The present invention can be used to control insect pests at all stages of their life cycle, including eggs, larvae, nymphs, and adults.

[0630] In particular, the present invention can be used to control insect pests that feed on the roots of turfgrasses, including grubs (such as Cyclocephala spp. (e.g., the marked beetle, C. lurida), Rhizotrogus spp. (e.g., the European beetle, R. majalis), Cotinus spp. (e.g., the Green June beetle, C. nitida), Popillia spp. (e.g., the Japanese beetle, P. japonica), Phyllophaga spp. (e.g., the May / June beetle), Ataenius spp. (e.g., the Black turfgrass ataenius, A. spretulus), Maladera spp. (e.g., the Asiatic garden beetle, A. beetle, M. castanea, and Tomarus genera), ground pearls (Margarodes spp.), mole crickets (tawny, southern, and short-winged; Scapteriscus spp., Gryllotalpa africana), and leatherjackets (European crane fly, Tipula spp.).

[0631] The present invention can also be used to control insect pests of turfgrass in thatched homes, including armyworms (such as the fall armyworm Spodoptera frugiperda, and the common armyworm Spodoptera frugiperda), cutworms, weevils (Species of the genus Cryptorhynchus, such as S. venatus verstitus and S. parvulus), and grass borers (such as species of the genus Herpetogramma and the tropical grass borer, Herpetogramma phaeopteralis).

[0632] The present invention can also be used to control insect pests in turfgrasses that live above ground and feed on turfgrass leaves, including wheat stink bugs (such as the southern wheat stink bug, Blissus insularis), Bermudagrass mite (Eriophyes cynodoniensis), Grass mealybug (Antonina graminis), Propsapia bicincta, leafhoppers, cutworms (Noctuidae), and Schizaphis graminis.

[0633] The present invention can also be used to control other pests in turfgrass, such as introduced fire ants (Solenopsis invicta) that create nests in lawns.

[0634] In the hygiene field, the composition according to the invention can effectively combat surface parasites such as hard ticks, soft ticks, scabies mites, autumn mites, flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas.

[0635] Examples of such parasites are:

[0636] From the order of the Pediculus: Haemaphysalis spp., Linognathus spp., Pediculus hominis spp., and Phtirus spp., Phitirus spp.

[0637] From the order Trichophagus: Felicola species, Brachypelago species, Ducklingia species, Cattlelicia species, Werneckiella species, Lepikentron species, Cattlelicia species, Trichopelago species and Felicola species (Felicola spp.).

[0638] From the order Diptera and the suborders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp. spp.), Musca spp., Hydrotaea spp., Biting flies 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. spp.) and Melophagus spp.

[0639] From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllum spp.

[0640] From the order of the Heteropterida, for example, Cimex spp., Triatominae spp., Panstrongylus spp.

[0641] From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattelagermanica and Supella spp.

[0642] Subclass Acaria (family Acarida) and orders Meta-stigmata and Meso-stigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyommas spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp. spp.), Sternostoma spp., and Varroa spp.

[0643] From the orders Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp. spp.), Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcooptes spp., Notoedress spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp.

[0644] The compositions according to the invention can also be suitable for protecting materials such as wood, textiles, plastics, adhesives, glues, paints, paper and card, leather, floor coverings and construction materials from infestation by insects.

[0645] The compositions according to the invention can be used, for example, to combat the following pests: beetles, such as 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), Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., and Dinoderus minutus, as well as Hymenoptera, such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, and Urocerus augur, and termites, such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes spp. indicola), Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis and Coptotermes formosanus, as well as borers such as Silverfish (Lepisma saccharina).

[0646] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or their salts are particularly suitable for controlling one or more pests selected from the group consisting of: Spodoptera species, Spodoptera species, Heliothis species, Trichodesmium species, Tuta species, Plutella xylostella species, Trichodesmium species, Trichodesmium species, Amyelois species, Amyelois species, Spodoptera species, Spodoptera species, Elasmopalpus species, Dalbulus species, Sternechus species, Striped flea beetle species, Scarabaeidae species, White grain borer species, Grass borer species, Cnaphalocrosis species, Tetradactylus species, Panonychus species, Tea yellow mite species, and Acanthodes species. species, Echinops species, Echinops species, Echinops species, Echinops species, Nilaparvata species, Sogatella species, Laodelphax species, Papilio striatus species, Melingethes species, Striped Leaf Beetle species, Click Beetle species, Hypnoidus species, Limonius species, Comb-clawed Click Beetle species, Broad-breasted Click Beetle species, Ground Fly species, Amphimallon species, Arc Beetle species, American Stink Bug species, Wall Bug species, Green Stink Bug species, Dichelops species, Lygus species, Rice Margin Stink Bug species, Flat Shield Bug species, Halymorpha species, Thrips species, Hard Thrips species, Flower Thrips species, Flower Weevil species, Melingethes species, Striped Flea Beetle species, Leaf Beetle species, Whitefly species, Whitefly species, Aphid species and Tuberculosis species.

[0647] In preferred embodiments of each aspect, compound TX (wherein the abbreviation "TX" means "a compound selected from the group consisting of the compounds defined in Tables 1 to 5 and Table P") controls one or more pests selected from the group consisting of Spodoptera species, Spodoptera species, Heliothis species, Cynocephala species, Tuta species, Plutella xylostella species, Cynocephala species, Cynocephala species, Cynocephala species, Cynocephala species, Elasmopalpus species, Dalbulus species, Sternechus species, Striped flea beetle species, Scarabaeidae species, White grain borer species, Graminus borer species, Leaf roller species, Tetradactylus species, Panonychus species, Tea yellow mite species, Leaf tick species, Spinifex species, Spinifex spp., Spinifex spp., species, Brevella species, Micropapilionidae species, Echinops species, Brown planthopper species, Whiteback planthopper species, Laodelphax species, Blacktail leafhopper species, Striped leaf beetle species, Click beetle species, Hypnoidus species, Limonius species, Comb-clawed click beetle species, Broad-breasted click beetle species, Ground fly species, Amphimallon species, Arc beetle species, American stink bug species, Wall stink bug species, Green stink bug species, Dichelops species, Lygus species, Rice-margined stink bug species, Flat shield stink bug species, Brown-winged stink bug species, Thrips species, Hard Thrips species, Flower Thrips species, Flower elephant species, Melingethes species, Striped flea beetle species, Leaf beetle species, Whitefly species, Whitefly species, Aphid species and Tuberculosis species.

[0648] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or their salts are particularly suitable for controlling one or more pests selected from the group consisting of: Spodoptera species (e.g., Spodoptera frugiperda, Spodoptera littoralis), cotton bollworm, tobacco budworm, eggplant borer, tomato leafminer, diamondback moth, codling moth, flower winged tortoise species, tortoise species, bean borer, soybean silver moth, black cutworm, South American corn borer (Elasmopalpus lignosellus), corn yellow-winged leafhopper, striped flea beetle species, Japanese beetle, yellow stem borer, striped stem borer, rice leaf roller (Cnaphalocrosism medinalis), two-spotted spider mite, apple mites, polyphagous tarsoneme mite, citrus rust mite, short-palped mite species, tomato spiny gall mite, brown planthopper, white-backed planthopper (Sogatella frucifera), gray planthopper, black-tailed leafhopper species, corn rootworm (Diabrotica vigifera), click beetle species, Hypnoidus bicolor, gray-headed click beetle (Limonius canus), cabbage ground fly, Japanese beetle, hero American stink bug (Euschistus heros), broomstick shield bug (Piezodorus lituratus), green rice stink bug, green-bellied stink bug (Dichelops furcatus), Lygus species, grass spider stink bug (Leptocorisa acuta), brown-winged stink bugs, tabaci thrips, tea yellow thrips, western flower thrips, cotton boll weevils, rapeseed beetles, striped flea beetle species, potato beetles, Bemisia tabaci, greenhouse whitefly, cotton aphid, and green peach aphid.

[0649] In preferred embodiments of each aspect, compound TX (wherein the abbreviation "TX" means "a compound selected from the group consisting of the compounds defined in Tables 1 to 5 and Table P") controls one or more pests selected from the following genera: Spodoptera species (e.g., Spodoptera frugiperda, Spodoptera littoralis) + TX, Helicoverpa armigera + TX, Tobacco budworm + TX, Eggplant yellow moth + TX, Tomato leafminer + TX, Diamondback moth + TX, Codling moth + TX, Flower-winged tortoise moth + TX, Tortoise moth + TX, Bean borer + TX, Sophora japonica + TX, Cutworm + TX, South American corn borer + TX, Corn leafhopper + TX, Striped flea beetle + TX, Japanese beetle + TX, Striped stem borer + TX, Chilo suppressalis + TX, Rice leaf roller + TX, Two-spotted spider mite + TX, Panonychus apple + TX, Polyphagous lateralis + TX Line mite + TX, citrus rust mite + TX, Brevipalpus species + TX, tomato spiny gall mite + TX, brown planthopper + TX, white-backed planthopper + TX, gray planthopper + TX, black-tailed leafhopper species + TX, corn rootworm + TX, click beetle species + TX, Hypnoidus bicolor + TX, gray-headed click beetle + TX, cabbage seed fly + TX, Japanese beetle + TX, hero American stink bug + TX, broom shield bug + TX, rice green stink bug + TX, green-bellied stink bug + TX, Lygus species + TX, grass spider stink bug + TX, brown-winged stink bug + TX, tobacco thrips + TX, tea yellow thrips + TX, western flower thrips + TX, cotton boll weevil + TX, rapeseed beetle + TX, striped flea beetle species + TX, potato beetle + TX, Bemisia tabaci + TX, greenhouse whitefly + TX, cotton aphid + TX and green peach aphid + TX.

[0650] The compounds of formula I, I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a and I-4a or their salts are particularly suitable for controlling the listed pests in the crops listed in the table below.

[0651]

[0652]

[0653]

[0654]

[0655] In preferred embodiments of each aspect, compound TX (wherein the abbreviation "TX" means "a compound selected from the group consisting of the compounds defined in Tables 1 to 5 and Table P") controls one or more of: Spodoptera species (e.g., Spodoptera frugiperda, Spodoptera littoralis), cotton bollworm, tobacco budworm, eggplant borer, tomato leafminer, diamondback moth, codling moth, flower-winged tortoise moth, tortoise moth, bean borer, soybean silver moth, black cutworm, South American corn borer, corn leafhopper, striped flea beetle species, Japanese beetle, yellow stem borer, striped stem borer, rice leaf roller, brown planthopper, whiteback planthopper, gray planthopper, blacktail leafhopper species, Bemisia tabaci, greenhouse whitefly, cotton aphid and peach aphid; such as Spodoptera species. TX, ...

[0656] The compounds according to the present invention may have any number of benefits, including, among others, favorable levels of biological activity for protecting plants against insects or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, favorable activity spectrum, increased safety (against non-target organisms above and below ground, such as fish, birds, and bees), improved physico-chemical properties, or increased biodegradability). In particular, it has been unexpectedly discovered that certain compounds of formula (I) can exhibit favorable safety profiles against non-target arthropods, particularly pollinators such as honey bees, solitary bees, and bumble bees. Most particularly, against the Italian honey bee (Apis mellifera).

[0657] The compounds according to the invention can be used as pesticides in unmodified form, but they are usually formulated into compositions in various ways using formulation adjuvants such as carriers, solvents and surfactants. These formulations can be in different physical forms, for example, in the form of dusts, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, mobile oils, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or water-miscible organic solvents as carriers), impregnated polymer films or in other known forms, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st edition, second revision (2010). Such formulations can be used directly or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological organisms, oil or solvents.

[0658] These formulations can be prepared, for example, by mixing the active ingredient with a formulation adjuvant to obtain a composition in the form of a finely divided solid, granules, solution, dispersion or emulsion. The active ingredients can also be formulated with other adjuvants such as finely divided solids, mineral oils, oils of plant or animal origin, modified oils of plant or animal origin, organic solvents, water, surfactants or combinations thereof.

[0659] These active ingredients can also be contained in very fine microcapsules. Microcapsules contain active ingredients in porous carriers. This allows the active ingredient to be released (for example, slowly released) into the environment in a controlled amount. Microcapsules typically have a diameter of from 0.1 to 500 microns. The amount of active ingredient they contain is about 25% to 95% of the capsule weight by weight. These active ingredients can be in the form of a holistic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulated membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed, in which the active ingredient is contained in a solid matrix of a base material in the form of finely dispersed particles, but these microcapsules themselves are not wrapped.

[0660] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. As liquid carriers, water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, 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, glyceryl acetate, glyceryl diacetate, glyceryl triacetate, decaglycerol Hexadecane, Hexanediol, Isoamyl Acetate, Isobornyl Acetate, Isooctane, Isophorone, Cumene, Isopropyl Myristate, Lactic Acid, Lauramine, Mesityl Oxide, Methoxypropanol, Methyl Isoamyl Ketone, Methyl Isobutyl Ketone, Methyl Laurate, Methyl Caprylate, Methyl Oleate, Methylene Chloride, m-Xylene, n-Hexane, n-Octylamine, Octadecanoic Acid, Octylamine Acetate, Oleic Acid, Oleylamine, o-Xylene, Phenol, Polyethylene Glycol, Propionic Acid, Propyl Lactate , propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0661] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soy flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

[0662] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially those which can be diluted with a carrier before use. Surface-active substances can be anionic, cationic, nonionic or polymeric and they can act as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium laurylsulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / alkylene oxide addition products, such as ethoxylated nonylphenol; alcohol / alkylene oxide addition products, such as ethoxylated tridecanol; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; salts of dialkylsulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammoniums, such as dodecyltrimethylammonium 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 dialkyl phosphates; and further substances, such as are described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Company. Corp., Ridgewood New Jersey (1981).

[0663] Additional 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, substances and buffers that neutralize or change the pH, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, microbicides, and liquid and solid fertilizers.

[0664] The composition according to the invention may comprise an additive comprising an oil of plant or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil and an oil derivative. The amount of the oil additive in the composition according to the invention is generally from 0.01% to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or oil of plant origin, such as rapeseed oil, olive oil or sunflower oil; emulsified vegetable oils; alkyl esters of oils of plant origin, such as methyl derivatives; or oils of animal origin, such as fish oil or tallow. Preferred oil additives include C8-C 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0665] These compositions according to the invention generally comprise from 0.1% to 99% by weight, in particular from 0.1% to 95% by weight, of a compound according to the invention and from 1% to 99.9% by weight of formulation adjuvants, which preferably include from 0 to 25% by weight of surface-active substances. Whereas commercial products may preferably be formulated as concentrates, the end user will generally use dilute formulations.

[0666] The application rate varies within wide limits and depends on the nature of the soil, the application method, the crop plants, the harmful organisms to be controlled, the prevailing climatic conditions, and other factors dictated by the application method, the time of application, and the target crop. In general, the compound can be applied at a rate of from 1 to 2000 l / ha, in particular from 10 to 1000 l / ha.

[0667] A preferred formulation may have the following composition (wt %):

[0668] Emulsifiable concentrates :

[0669] Active ingredient: 1% to 95%, preferably 60% to 90%

[0670] Surfactant: 1% to 30%, preferably 5% to 20%

[0671] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0672] Dust powder :

[0673] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0674] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%

[0675] Suspension concentrate:

[0676] Active ingredient: 5% to 75%, preferably 10% to 50%

[0677] Water: 94% to 24%, preferably 88% to 30%

[0678] Surfactant: 1% to 40%, preferably 2% to 30%

[0679] wettable powder :

[0680] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0681] Surfactants: 0.5% to 20%, preferably 1% to 15%

[0682] Solid carrier: 5% to 95%, preferably 15% to 90%

[0683] Granules:

[0684] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0685] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0686] By adding other insecticidal, acaricidal and / or fungicidal active ingredients, the activity of the compositions according to the invention can be significantly broadened and adapted to prevailing conditions. Mixtures of compounds of formula (I) with other insecticidal, acaricidal and / or fungicidal active ingredients can also have further surprising advantages, which can also be described in a broader sense as synergistic activities. For example, better tolerance of plants, reduced phytotoxicity, insects can be controlled at different stages of their development, or better behavior during their production (e.g., during grinding or mixing, during their storage or during their use).

[0687] Suitable active ingredients for addition are, for example, representatives of the following classes of active ingredients: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, neonicotinoids and Bacillus thuringiensis preparations.

[0688] Preference is given to the following mixtures of compounds of formula (I) with active substances (the abbreviation "TX" means "a compound selected from the group consisting of the compounds defined in Tables 1 to 5 and Table P"):

[0689] An auxiliary agent selected from the group consisting of: petroleum (alias) (628) + TX;

[0690] Abamectin + TX, acetamiprid + TX, acetamiprid + TX, flumethrin + TX, acynonapyr + TX, bifenapyr + TX, afoxolaner + TX, cotton bell carbendazim + TX, allethrin + TX, α-cypermethrin + TX, alpha-cypermethrin + TX, sulfamethoxazole + TX, cypermethrin + TX, triazotin + TX, sulfamethoxazole + TX, benzyltrimethoxam + TX, benzpyrimoxan + TX, β-cyfluthrin + TX, β-cypermethrin + TX, bifenazate + TX, bifenthrin + TX, binapacryl + TX, bioallethrin + TX, S-bioallethrin + TX, bio-resmethrin + TX, bistrifluan + TX, broflanilide + TX, brofluthrin + TX, bromophos-ethyl + TX, buprofezin + TX, butacarb + TX, cadusafos + TX, carbaryl + TX, butacarb + TX, batan + 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.:1 922957-46-7+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, chlorpromazide+TX, chloranil+TX, chlorfenapyr+TX, chlorfenapyr+TX, cyclanil+TX, clenpyrine+TX, cloethocarb+TX, clothianidin+TX, 2-chlorophenyl N-methylcarbamate (CPMC)+TX, benzonitrile+TX, cyanantraniliprole+TX, cyclobromofenapyr+TX, trifluralin m)+TX, pyrethroids+TX, cycloxanil+TX, cytoxanil+TX, cyetpyrafen+TX, cyetpyrafen (or etpyrafen)+TX, cyfluthrin+TX, cyhalodiamide+TX, cyhalothrin+TX, cypermethrin+TX, cypermethrin+TX, cyproflanilide+TX, cyromazine+TX, deltamethrin+TX, cyfenapyr+TX, chlorpyrifos+TX, chlorfenapyr+TX, dibrom+TX, dicloromezotiaz+TX, fluazifop+TX, diflubenzuron+TX, Dimpropyridaz + TX, dimethoate + TX, dinotefuran + TX, venotefuran + TX, emamectin (or emamectin benzoate) + TX, d-methrin + TX, epsilon-momfluorothrin + TX, epsilon-metofluthrin + TX, cypermethrin + TX, ethion + TX, ethomethrin + TX, etoxazole + TX, famox + TX, fenazaquin + TX, pentothrin + TX, fenmezoditiaz + TX, fenitrothion + TX, fenobutanil + TX, fenthiocarb + TX, fenoxycarb + TX, cypermethrin + TX , fenpyroximate + TX, fensulfuron + TX, fenthion + TX, yesalin + TX, cypermethrin + TX, fipronil + TX, flometoquin + TX, flonicamid + TX, cypermethrin + TX, fluazaindolizine + TX, flupyrimid + TX, flubendiamide + TX, fluchlordiniliprole + TX, flucitrinate + TX, flufenoxuron + TX, flucythrin + TX, fluthiazolin + TX, flumethrin + TX, flumethrin + TX, flumethrin + TX, butenefipronil + TX,Fluhexafon + TX, fluchlorfenapyr + TX, fluopyram + TX, flupentiofenox + TX, flupyroxystrobin + TX, flupyrimin + TX, fluralaner + TX, fluvalinate + TX, fluxametamide + TX, thiazolin + TX, gamma-cyhalothrin + TX, pyrimidine + TX, chlorfenapyr + TX, benzyl ammonium chloride + TX, heptafluthrin + TX, hexathiazolin + TX, fluorinated Hydracarb + TX, imicyafos + TX, imidacloprid + TX, imiprodinil + TX, indazapyroxamet + TX, indoxacarb + TX, iodomethane + TX, iprodione + TX, isocycloseram + TX, isothiocarb + TX, ivermectin + TX, kappa-bifenthrin + TX, kappa-tefluthrin + TX, lambda-cyhalothrin + TX, ledprona + TX, lepidomycin + TX, lotilaner + TX, chlorfenuron + TX, metaflumizone + TX, metaldehyde + TX, methomyl + TX, methomyl + TX, methoxyfenozide + TX, methoxyfenozide Flumethrin + TX, cypermethrin + TX, chlorpyrifos + TX, acarb + TX, momfluorothrin + TX, cypermethrin + TX, nicofluprole + TX; nitenpyram + TX, nithiazine + TX, omethoate + TX, oxamyl + TX, oxazosulfyl + TX, parathion-ethyl + TX, permethrin + TX, phenothrin + TX, phosphamidon + TX, piperonyl butoxide + TX, pirimicarb + TX, pirimiphos-ethyl + TX, pirimiphos-methyl + TX, polyhedrosis virus + TX, prallethrin + TX, profenofos + TX, Profluthrin + TX, propargite + TX, chlorpyrifos + TX, propoxur + TX, prothiophos + TX, protrifenbute + TX, pyflubumide + TX, pymetrozine + TX, pyrafluprole + TX, pyridaben + TX, pyridalyl + TX, pyrifluquinazon + TX, pyriminostrobin + TX, pyraflufen + TX, pyrimethrin + TX, pyriproxyfen + TX, resmethrin + TX, sarolaner + TX, selamectin + TX, silafluthrin + TX,Spinosad + TX, spinosad + TX, spirobudifen + TX; spirodiclofen + TX, spiromesifen + TX, spiropidion + TX, spirotetramat + TX, spidoxamat + TX, sulfonecarb + TX, tebufenozide + TX, tebufenpyrad + TX, tebupirimiphos + TX, tefluthrin + TX, temephos + TX, tetracycline + TX, tetracycline sulfone + TX, tetramethrin + TX, tetramethrin + TX, tetramethrin + TX , acaricide + TX, flucyranilamide + TX, θ-cypermethrin + TX, thiacloprid + TX, thiamethoxam + TX, thiodicarb + TX, long-lasting carb + TX, methyl benzyl sulfate + TX, sulfamethoxam + TX, tigolaner + TX, tiorantraniliprole + TX; tioxazafen + TX, tolfenpyrad + TX, toxaphene + TX, tralomethrin + TX, transfluthrin + TX, triazophos + TX, trichlorfon + TX, chlorpyrifos + TX, trichlorfon + TX, Trifluoxetine ( trifluenfuronate)+TX, triflumezopyrim+TX, tyclopyrazoflor+TX, ζ-cypermethrin+TX, seaweed extract and fermentation products derived from sugar acyl+TX, seaweed extract and fermentation products derived from sugar acyl (containing urea+TX, amino acids+TX, potassium and molybdenum, and EDTA-chelated manganese)+TX, seaweed extract and fermented plant products+TX, seaweed extract and fermented plant products (containing plant hormones+TX, vitamins+TX, EDTA-chelated copper+TX, zinc+TX, and iron+TX), azadirachtin+TX, Bacillus aizawai+TX, Bacillus chitinosporus AQ746 (NRRL Accession No. B-21 618)+TX, Bacillus firmus+TX, Bacillus kurstaki+TX, Bacillus mycoides AQ726 (NRRL Accession No. B-21664)+TX, Bacillus pumilus (NRRL Accession No. B-30087)+TX, Bacillus pumilus AQ717 (NRRL Accession No. B-21662)+TX, Bacillus species AQ178 (ATCC Accession No. 53522)+TX, Bacillus species AQ175 (ATCC Accession No. 55608)+TX, Bacillus species AQ177 (ATCC Accession No. 55609)+TX, unspecified Bacillus subtilis+TX, Bacillus subtilis AQ153 (ATCC accession number 55614) + TX, Bacillus subtilis AQ30002 (NRRL accession number B-50421) + TX, Bacillus subtilis AQ30004 (NRRL accession number B-50455) + TX, Bacillus subtilis AQ713 (NRRL accession number B-21661) + TX, Bacillus subtilis AQ743 (NRRL accession number B-21665) + TX, Bacillus thuringiensis AQ52 (NRRL accession number B-21619) + TX, Bacillus thuringiensis BD#32 (NRRL accession number B-21530) + TX, Bacillus thuringiensis subsp. Kurstaki (subspec.Kurstaki) BMP 123 + TX, Beauveria bassiana + TX, D-limonene + TX, Granulovirus + TX, Harpin + TX, Helicoverpa armigera nuclear polyhedrosis virus + TX, Helicoverpa viridis nuclear polyhedrosis virus + TX, Helicoverpa viridis nuclear polyhedrosis virus + TX, Helicoverpa viridis Australasian nuclear polyhedrosis virus + TX, Metarhizium species + TX, Muscodor albus 620 (NRRL Accession No. 30547) + TX, Muscodor roseus A3-5 (NRRL Accession No. 30548) + TX, neem-based products + TX, Paecilomyces fumosorum + TX, Paecilomyces lilacinus + TX, Pasteuria szabalensis + TX, Pasteuria penetrantis + TX, Pasteuria mycoides + TX, Pasteuria soreiroides thornei)+TX, Pasteurella+TX, p-cymene+TX, Plutella xylostella granulovirus+TX, Plutella xylostella nuclear polyhedrosis virus+TX, polyhedrosis virus+TX, pyrethrum+TX, QRD420 (terpenoid blend)+TX, QRD 452 (terpenoid blend)+TX, QRD 460 (terpenoid blend)+TX, Quillaja saponaria+TX, Rhodococcus sphaeroides AQ719 (NRRL Accession No. B-21663)+TX, Spodoptera frugiperda nuclear polyhedrosis virus+TX, Streptomyces flavos (NRRL Accession No. 30232)+TX, Streptomyces sp. (NRRL Accession No. B-30145)+TX, terpenoid blend+TX, and Verticillium sp.+TX;

[0691] an algaecide selected from the group consisting of bethoxazin [CCN] + TX, copper dioctanoate (IUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endoxan (295) + TX, fentin (347) + TX, slaked lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347) + TX;

[0692] Anthelmintics selected from the group consisting of: avermectin (1) + TX, clefonate (1011) + TX, trifluoperazine + TX, doramectin (alias) [CCN] + TX, emamectin (291) + TX, emamectin benzoate (291) + TX, eprinomectin (alias) [CCN] + TX, ivermectin (alias) [CCN] + TX, milbemycin oxime (alias) [CCN] + TX, moxidectin (alias) [CCN] + TX, piperazine [CCN] + TX, selamectin (alias) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX;

[0693] Avicides selected from the group consisting of chloralose (127) + TX, endrin (1122) + TX, fenthion (346) + TX, pyridin-4-amine (IUPAC name) (23) and strychnine (745) + TX;

[0694] Bactericide selected from the group consisting of: 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (IUPAC name) (170) + TX, copper hydroxide (IUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1105) + TX, dodesine (1112) + TX, fenaminosulf (1144) + TX, formaldehyde (404) + TX, mercaptophenone ( Synonyms) [CCN] + TX, kasugamycin (483) + TX, kasugamycin hydrochloride hydrate (483) + TX, nickel bis(dimethyldithiocarbamate) (IUPAC name) (1308) + TX, nitrapyrin (580) + TX, octhilinone (590) + TX, oxolinic acid (606) + TX, oxytetracycline (611) + TX, potassium hydroxyquinoline sulfate (446) + TX, probenazole (658) + TX, streptomycin (744) + TX, streptomycin sesquisulfate (744) + TX, chlorpheniramine (766) + TX, and thimerosal (synonyms) [CCN] + TX;

[0695] A biological agent selected from the group consisting of: GV of cotton brown banded moth (alias) (12) + TX, Agrobacterium radiobacterium (alias) (13) + TX, Amblyseius spp. (alias) (19) + TX, NPV of celery budworm (alias) (28) + TX, Anagrus atomus (alias) (29) + TX, Aphelinus abdominalis (alias) (33) + TX, Aphidius colemani (alias) (34) + TX, Aphidoletes aphidimyza (alias) (35) + TX, NPV of lucerne budworm (alias) (38) + TX, Bacillus firmus (alias) (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 (scientific name) (51) + TX, Beauveria bassiana (alias) (53) + TX, Beauveria brongniartii (alias) (54) + TX, Chrysoperla carnea (alias) (151) + TX, Cryptolaemus montrouzieri (alias) (178) + TX, Codling moth GV (alias) (191) + TX, Dacnusa sibirica (alias) (212) + TX, Diglyphus isaea (alias) (254) + TX, Eretmocerus sibirica (scientific name) (293) + TX, Eretmocerus sibirica (alias) eremicus) (alias) (300) + TX, Spodoptera exigua NPV (alias) (431) + TX, Heterorhabditis bacteriophora and H. megidis (alias) (433) + TX, Hippodamia convergens (alias) (442) + TX, Leptomastix dactylopii (alias) (488) + TX, Macrolophus caliginosus (alias) (491) + TX, Spodoptera exigua NPV (alias) (494) + TX, Metaphycus helvolus (alias) (522) + TX, Metarhizium anisopliae var.acridum)(scientific name)(523)+TX, Metarhizium anisopliae var. anisopliae)(scientific name)(523)+TX, Neodiprion sertifer NPV and Neodiprion sertifer (Neodiprion sertifer) NPV.lecontei)NPV (alias) (575) + TX, Paecilomyces spp. (alias) (596) + TX, Paecilomyces fumosoroseus (alias) (613) + TX, Phytoseiulus persimlis (alias) (644) + TX, Spodoptera exigua multicapsidnuclear polyhedrosis virus (scientific name) (741) + TX, Steinernema bibionis (alias) (742) + TX, Steinernema carpocapsae (alias) (742) + TX, Steinernema glaseri (alias) (742) + TX, Steinernema riobrave) (alias) (742) + TX, Steinernema riobravis (alias) (742) + TX, Steinernema scapterisci (alias) (742) + TX, Steinernema spp. (alias) (742) + TX, Trichogramma spp. (alias) (826) + TX, Typhlodromus occidentalis (alias) (844) and Verticillium lecanii (alias) (848) + TX;

[0696] Soil disinfectant selected from the group consisting of methyl iodide (IUPAC name) (542) and methyl bromide (537) + TX;

[0697] A chemical sterilant selected from the group consisting of: apholanate [CCN] + TX, bisazir (alias) [CCN] + TX, busulfan (alias) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alias) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholanate [CCN] + TX, methyl bisazir ... apholate) [CCN] + TX, morzid [CCN] + TX, penfluron (other name) [CCN] + TX, tepa [CCN] + TX, thiohempa (other name) [CCN] + TX, thiohexamethylenetepa (other name) [CCN] + TX, trotamide (other name) [CCN] and urethaneimide (other name) [CCN] + TX;

[0698] An insect pheromone selected from the group consisting of (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-methylhept-2-en-4-ol (IUPAC name) (541) + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate (IUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285) + TX, (Z)-hexadecan-11-enal (IUPAC name) (436) + TX, (Z)-hexadecan-11-en-1-yl acetate (IUPAC name) (437) + TX X, (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438) + TX, (Z)-eicos-13-en-10-one (IUPAC name) (448) + TX, (Z)-tetradec-7-en-1-al (IUPAC name) (782) + TX, (Z)-tetradec-9-en-1-ol (IUPAC name) (783) + TX, (Z)-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)-tetradec-9,11-dien-1-yl acetate (IUPAC name) (780) + TX, (9Z,12E)-tetradec-9,12-Dien-1-yl acetate (IUPAC name) (781) + TX, 14-methyloctadec-1-ene (IUPAC name) (545) + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one (IUPAC name) (544) + TX, alpha-multistriatin (alias) [CCN] + TX, western pine beetle gathering pheromone (brevicomin) (alias) [CCN] + TX, codlelure (alias) [CCN] + TX, codlemone (alias) (167) + TX, cuelure (alias) ( 179)+TX, disparlure (277)+TX, dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl acetate (IUPAC name) (287)+TX, dodec-8+TX, 10-dien-1-yl acetate (IUPAC name) (284)+TX, dominicalure (alias) [CCN]+TX, ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol (alias) [CCN]+TX, southern pine beetle aggregation pheromone (frontalin) (alias) [CCN]+TX, 1:1 mixture of (Z,E) and (Z,Z) isomers of (hexadec-7,11-dien-1-yl acetate) (420) + TX, grandlure (421) + TX, grandlure I (alternative name) (421) + TX, grandlure II (alternative name) (421) + TX, grandlure III (alternative name) (421) + TX, grandlure IV (alternative name) (421) + TX, hexalure [CCN] + TX, ipsdieno l)(alias) [CCN] + TX, ipsenol (alias) [CCN] + TX, japonilure (alias) (481) + TX, lineatin (alias) [CCN] + TX, litlure (alias) [CCN] + TX, looplure (alias) [CCN] + TX, medlure [CCN] + TX, megatomoic acid acid)(alias)[CCN]+TX、Muscalure(alias)(540)+TX、Muscalure(563)+TX、Octadec-2,13-dien-1-yl acetate(IUPAC name)(588)+TX、Octadec-3,13-dien-1-yl acetate(IUPAC name)(589)+TX、Orfralure(alias)[CCN]+TX、Oryctalure(alias)(317)+TX、Ostromone(alias)[CCN]+TX、Siglu re)[CCN]+TX, banana bulb weevil attractant (sordidin) (alternative name) (736)+TX, sulcatol (alternative name) [CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC name) (785)+TX, Mediterranean fruit fly attractant (839)+TX, Mediterranean fruit fly attractant A (alternative name) (839)+TX, Mediterranean fruit fly attractant B1 (alternative name) (839)+TX, Mediterranean fruit fly attractant B2 (alternative name) (839)+TX, Mediterranean fruit fly attractant C (alternative name) (839) and trunc-call (alternative name) [CCN]+TX;

[0699] Insect repellents selected from the group consisting of 2-(octylthio)ethanol (IUPAC name) (591) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (IUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (IUPAC name) (1048) + TX, DEET [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexylurea [CCN] + TX, methoquin-butyl (1276) + TX, methyl neodecylamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX;

[0700] Molluscicides selected from the group consisting of di(tributyltin) oxide (IUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, chloranil (999) + TX, copper acetyl arsenite [CCN] + TX, copper sulfate (172) + TX, triphenyltin (347) + TX, iron phosphate (IUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-ethanolamine (576) + TX, pentachlorophenol ( 623)+TX, sodium pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX, trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole [394730-71-3]+TX;

[0701] A nematicide selected from the group consisting of: 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) Abstract name) (1065) + TX, 3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980) + TX, 5-methyl-6-thioxo-1,3,5-thiadiazin-3-yl acetic acid (IUPAC name) (1286) + TX, 6-isopentenylaminopurine (alias) (210) + TX, avermectin (1) + TX, acetofenamide [CCN] + TX, cotton bell carb (15) + TX, aldicarb (16) + TX, aldicarb (863) + TX, AZ 60541 (compound code) + TX, benclothiaz [CCN] + TX, benomyl (62) + TX, butylpyridaben (alias) + TX, chlorpyrifos (109) + TX, carbofuran (118) + TX, carbon disulfide (945) + TX, carbofuran (119) + TX, chloropicrin (141) + TX, chlorpyrifos (145) + TX, chlorpyrifos ( 999) + TX, triflupyridine + TX, cytokinin (alias) (210) + TX, dazomet (216) + TX, DBCP (1045) + TX, DCIP (218) + TX, diamidafos (1044) + TX, diflunisal (1051) + TX, dicliphos (alias) + TX, dimethoate (262) + TX, doramectin (alias) [CCN ]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX, eprinomectin (alias) [CCN]+TX, ethoprophos (312)+TX, dibromoethane (316)+TX, fenamiphos (326)+TX, fenpyrad (alias)+TX, fensulfonylphos (1158)+TX, thiazophos (408)+TX, thiophanate-methyl (1196)+TX, furfural (alias) [CCN] +TX, GY-81 (research code) (423) +TX, cypermethrin [CCN] +TX, iodomethane (IUPAC name) (542) +TX, isamidophos (1230) +TX, chlorfenapyr (1231) +TX, ivermectin (alias) [CCN] +TX, kinetin (alias) (210) +TX, methylthiophos (1258) +TX, metamectin (519) +TX,Metamex potassium salt (alias) (519) + TX, Metamex sodium salt (519) + TX, methyl bromide (537) + TX, methyl isothiocyanate (543) + TX, milbemycin oxime (alias) [CCN] + TX, moxidectin (alias) [CCN] + TX, Myrothecium verrucaria composition (alias) (565) + TX, NC-184 (compound code) + TX, oxamyl (602) + TX, phorate (636) + TX, phosphamidon (639) + TX, phosphamidon [CCN] + TX, chlorpyrifos (alias) + TX, selamectin (alias) [CCN] N]+TX, spinosad (737)+TX, terbufos (alias)+TX, terbufos (773)+TX, tetrachlorothiophene (IUPAC / Chemical Abstracts name) (1422)+TX, thiafenox (alias)+TX, cypermethrin (1434)+TX, triazophos (820)+TX, triazuron (alias)+TX, xylenol [CCN]+TX, YI-5302 (compound code) and zeatin (alias) (210)+TX, fluensulfone [318290-98-1]+TX, fluopyram+TX;

[0702] A nitrification inhibitor selected from the group consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX;

[0703] Plant activators selected from the group consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alias) (720) + TX;

[0704] Rodenticides consisting of the following substance groups: 2-isovalerylindan-1,3-dione (IUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name) (748) + TX, α-chlorohydrin [CCN] + TX, aluminum phosphide (640) + TX, antoconazole (880) + TX, arsenic trioxide (882) + TX, barium carbonate (891) + TX, bisulfamethoxazole (912) + TX, brodifacoum (89) + TX, bromadiolone (including Including α-Bromadiolone) + TX, Bromadiolamine (92) + TX, Calcium Cyanide (444) + TX, Chloralose (127) + TX, Chloralone (140) + TX, Cholecalciferol (alias) (850) + TX, Chlorodiclofenac (1004) + TX, Cytoxan (1005) + TX, Cytoxan (175) + TX, Cytoxan (1009) + TX, Cytoxan (246) + TX, Cytoxan (249) + TX, Cytoxan (273) + TX, Calcifedol (301) + TX, Fludioxaline (357) + TX, fluoroacetamide (379) + TX, fludioxaline (1183) + TX, fludioxaline 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, fosfomycin (1318) + TX, fosfomycin (1 336) + TX, phosphine (IUPAC name) (640) + TX, phosphorus [CCN] + TX, warfarin (1341) + TX, potassium arsenite [CCN] + TX, warfarin (1371) + TX, scilla glycoside (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;

[0705] Synergists selected from the group consisting of 2-(2-butoxyethoxy)ethyl piperate (IUPAC name) (934) + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name) (903) + TX, farnesol with nerolidol (alias) (324) + TX, MB-599 (research code) (498) + TX, MGK 264 (research code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (research code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX;

[0706] Animal repellents, which are selected from the group consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper cyclohexane [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, salamine (804) + TX, trimethacarb (840) + TX, zinc cyclohexane [CCN] and ziram (856) + TX;

[0707] Virucidal agents selected from the group consisting of: imipenem (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX;

[0708] A wound protective agent selected from the group consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX;

[0709] Selected from the following biologically active substances: 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol+TX, 2,4-dichlorophenylbenzenesulfonate+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide+TX, 4-chlorophenylphenylsulfone+TX, acetofenapyr+TX, aldisulfonyl+TX, sagofos+TX, fomanphos+TX, amitriptyline+TX, amitriptyline hydrogen oxalate+TX, amitraz+TX, cypermethrin+TX, arsenic trioxide+TX, azobenzene+TX, azophos+TX, benomyl+TX, benomyl+TX, benzothiocarb+TX, benzyl benzoate+TX, bixafenthion+TX, bromethrin+TX, bromothiophene+TX, bromothiophene+TX X, bromopyralid + TX, buprofezin + TX, butanone carbendazim + TX, butanone sulfonyl carbendazim + TX, butylpyridaben + TX, calcium polysulfide + TX, octachlorocamphene + TX, chlormethoxam + TX, trithion + TX, cypermethrin + TX, cypermethrin + TX, cypermethrin + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, ethyl chlorfenapyr + TX, chlorfenapyr + TX, propyl chlorfenapyr + TX, chlorfenapyr + TX, cypermethrin I + TX, cypermethrin II + TX, cypermethrin + TX, closantel + TX, coumaphos + TX, crotamiton + TX, baclofos + TX , thiophanate+TX, fruit insect phosphorus+TX, DCPM+TX, DDT+TX, tianlephos+TX, tianlephos-O+TX, tianlephos-S+TX, demeton-methyl+TX, demeton-O+TX, demeton-O-methyl+TX, demeton-S+TX, demeton-S-methyl+TX, demeton-S-methyl+TX, demeton-S-methyl+TX, sulfonamide+TX, bacteriostatic+TX, dichlorvos+TX, dicliphos+TX, chlorpyrifos+TX, methylphosphine+TX, methylphosphine+TX, methylphosphine+TX, chlorpyrifos+TX, dinex+TX, dinex-diclexine )+TX, dinocap-4+TX, dinocap-6+TX, orthodimethoate+TX, nitropentyl+TX, nitrosyl ester acaricide+TX, nitrobutyl+TX, dimethoate+TX, sulfodiphenyl+TX, disulfiram+TX, DNOC+TX, phenoxyacetic acid+TX, doramectin+TX, fenoxaphos+TX, eprinomectin+TX, phosphine+TX, ethimox+TX, anti-mite+TX, fenbutatin+TX, fenthiocarb+TX, tebufenpyrad+TX, fenpyrad+TX, fenpyrad+TX, fenpyrad+TX, fenamipyrad+TX, fenamipyrad+TX, fenpyrad+TX, fenfluramide+TX, fluazifop+TX, flufenoxuron+TX, fluazifop+TX, flufenoxuron+TX, fluazifop+TX, FMC 1137+TX, fenvalerate+TX, fenvalerate hydrochloride+TX, carbendazim+TX, γ-HCH+TX, chlorpyrifos+TX, benzyl methoxyfen+TX, hexadecyl cyclopropane carboxylate+TX, isocarbophos+TX, jasmonate I+TX, jasmonate II+TX, iodonium chloride+TX, lindan+TX,Propionyl + TX, cypermethrin + TX, dithiophos + TX, methylthiophene + TX, acarbamate + TX, methyl bromide + TX, cypermethrin + TX, milbemycin + TX, propylamine + TX, monocrotophos + TX, maoguo + TX, moxidectin + TX, dibromophos + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, fluazifop + TX, nikkomycin + TX, pentocyanamide + TX, pentocyanamide 1:1 zinc chloride complex + TX, omethoate + TX, isothiosulfate + TX, sulfamethoxam + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, fenthion + TX, phosalone + TX, sulfur Cyclophos + TX, phosphamidon + TX, chlorinated turpentine + TX, acarb + TX, proclonol + TX, cypermethrin + TX, propoxur + TX, ethidium + TX, phosphamidon + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrin + TX, pyrimethoxam + TX, pyrithiophos + TX, quinalphos + TX, quinalphos + TX, R-1492 + TX, glyphosate + TX, rotenone + TX, octamidine + TX, clostridium + TX, selamectin + TX, thiothion + TX, SSI-121 + TX, disulfiram + TX, sulfluramid + TX, sulfotep + TX, sulfur + TX, fluazifop + TX, τ-fluvalinate + TX, TEPP + TX, terbutaline + TX, tetrachlorocarb Sulfone + TX, acaricide + TX, thiafenox + TX, cypermethrin + TX, long-lasting carbendazim + TX, methyl benzylphos + TX, acaricide + TX, thuringin + TX, cypermethrin + TX, benzylphos + TX, triazophos + TX, triazophos + TX, triclosan + TX, triamcinol + TX, aphidazole + TX, flupyrazone + TX, benzathiazolin + TX, copper dioctanoate + TX, copper sulfate + TX, cyprodinil + TX, dichloronaphthoquinone + TX, dichlorophen + TX, endoxan + TX, triphenyltin + TX, slaked lime + TX, sodium mancozeb + TX, quinone + TX, quinone + TX, simazine + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, fusulin + TX, piperazine Azine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodixan + TX, sodium disulfone + TX, formaldehyde + TX, mercurophen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, trichloromethylpyridine + TX, octhiothione + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, thiabendazole + TX, streptomycin + TX,Streptomycin sesquisulfate + TX, chlorophthalide + TX, thimerosal + TX, GV of cotton brown-banded tormentor + TX, Agrobacterium radiobacterium + TX, Amblyseius species + TX, Spodoptera exigua NPV + TX, Procera cerana + TX, Aphididae short-spurred wasp + TX, Cotton aphid parasitoid + TX, Aphid midge + TX, Spodoptera lucerne NPV + TX, Bacillus sphaericus + TX, Beauveria bassiana + TX, Common lacewing + TX, Cryptochilus monterilla + TX, GV of codling moth + TX, Siberian sibirica + TX , Pea leafminer + TX, Aphid wasp + TX, Aphid wasp + TX, Heterorhabditis bacteriophora and Heterorhabditis megidis + TX, Long-legged ladybird + TX, citrus mealybug parasitic wasp + TX, blind bug + TX, Cabbage looper NPV + TX, Yellow broad-stalked jumping wasp + TX, Yellow green Metarhizium + TX, Metarhizium anisopliae microspore variant + TX, European new pine sawfly (Neodiprion sertifer)NPV and red-headed new pine sawfly (N.lecontei)NPV+TX, small flower stink bug species+TX, fumosomolus+TX, Chilean phytoseiid mite+TX, mosquito nematode+TX, small tortoise moth nematode+TX, noctuid nematode+TX, Geerman nematode+TX, sharp nematode+TX, Steinernemariobravis+TX, mole cricket nematode+TX, +TX, Steinernema species+TX, Trichogramma species+TX, Western Typhlostomus+TX, Verticillium lecanii+TX, zophosphine+TX, sterile methylamine+TX, busulfan+TX, sterile amine+TX, hexamethylmelamine+TX, hexamethylphosphine+TX, methyl thio ... Alkyl imine + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-decyl Hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-eicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX,(9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnon-5-ol and 4-methylnon-5-one + TX, α-polystyrene + TX, western pine beetle aggregation pheromone + TX, dodecadienol + TX, caldoxime + TX, pyrrolidone + TX, epoxynonadecane + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8 + TX, 10-dien-1-yl acetate +TX, Domi attractant +TX, 4-methyloctanoic acid ethyl ester +TX, eugenol +TX, southern pine beetle gathering pheromone +TX, trapping ene mixture +TX, trapping ene mixture I +TX, trapping ene mixture II +TX, trapping ene mixture III +TX, trapping ene mixture IV +TX, hexane attractant +TX, tooth beetle dienol +TX, tooth beetle enol +TX, scarab sex attractant +TX, trimethyldioxytricyclononane (lineatin) +TX, moth sex attractant +TX, cabbage looper sex attractant +TX, trapping ester +TX, (3E,5Z)-tetradec-3,5-dienoic acid (megatomoic acid)+TX, entophore+TX, entophore+TX, octadec-2,13-dien-1-yl acetate+TX, octadec-3,13-dien-1-yl acetate+TX, cis-8-dodecenyl acetate+TX, coconut rhinoceros beetle aggregation pheromone+TX, feilocon+TX, insect ring+TX, banana corm weevil attractant (sordidin)+TX, fungivorous methyl entol+TX, tetradec-11-en-1-yl acetate+TX, Mediterranean fruit fly attractant+TX, Mediterranean fruit fly attractant A+TX, Mediterranean fruit fly attractant B1+TX, Mediterranean fruit fly attractant B2+TX, Mediterranean fruit fly attractant C+TX, trunc-call+TX, 2-(octylthio)-ethanol+TX, dimethoate+TX, butoxy(polypropylene glycol)+TX, dibutyl adipate+TX X, dibutyl phthalate + TX, dibutyl succinate + TX, DEET + TX, mosquito repellent + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexyl urea + TX, mequindoxaline + TX, methyl neodecylamide + 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-dichloropropylene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichloro-phenyl)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)phenylmethylcarbamate+TX, 2-(4-chloro-3,5-xylyloxy)ethanol+TX, 2-chlorovinyldiethyl phosphate+TX, 2-imidazolidinone+TX, 2-isovalerylindan-1,3-dione+TX, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate+TX, 2-thiocyanatoethyl laurate+TX, 3-bromo-1-chloroprop-1-ene+TX, 3-methyl-1-phenylpyrazole- 5-aminodimethyl-carbamate + TX, 4-methyl (prop-2-ynyl) amino-3,5-dimethylphenylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + TX, acethion + TX, acrylonitrile + TX, aldrin + TX, aloamicin + TX, chlorpyrifos + TX, α-deceprin + TX, aluminum phosphide + TX, chlorpyrifos + TX, neonicotinoids + TX, ethyl methidathion + TX, methyl pyrifos + TX, Bacillus thuringiensis δ -Endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, cypermethrin + TX, Bayer 22 / 190 + TX, Bayer 22408 + TX, β-cyfluthrin + TX, β-cypermethrin + TX, pentothrin + TX, biopermethrin + TX, bis (2-chloroethyl) ether + TX, borax + TX, bromophenazone + TX, bromo-DDT + TX, hexacarb + TX, cyfluthrin + TX, tebuconazole + TX, butylphos + TX, calcium arsenate + TX, calcium cyanide + TX, dimethoate Carbon sulfide + TX, carbon tetrachloride + TX, badan hydrochloride + TX, veratrine + TX, bornyl + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chloraniloxime + TX, chlorpyrifos + TX, cis-resmethrin + TX, cis-resmethrin + TX, cypermethrin + TX, copper acetylarensite + TX, copper arsenate + TX, copper oleate + TX, chlorfenapyr + TX, cryolite + TX, CS 708+TX, benzonitrile+TX, cypermethrin+TX, cypermethrin+TX, cypermethrin+TX, d-cypermethrin+TX, DAEP+TX, dazomethon+TX, demethylfuran+TX, chloranil+TX, isochlorvinphos+TX, chloranil+TX, dicresyl+TX, cypermethrin+TX, dieldrin+TX, diethyl 5-methylpyrazol-3-yl phosphate+TX, thiophene+TX, tetrafluthrin+TX, demacarb+TX, pyrethrin+TX, methylchlorfenapyr+TX, difenocarb+TX, propanol+TX, pentotropol+TX, dinoseb+TX, fenpropathrin+TX, vegetable phosphorus+TX, thiopyraphos+TX, DSP+TX, ecdysterone+TX, EI 1642+TX, EMPC+TX, EPBP+TX, etaphos+TX, ethiofencarb+TX,Ethyl formate + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, EXD + TX, cypermethrin + TX, fenthion + TX, ethylfenthion + TX, fluazifop + TX, butylfenthion + TX, phosphamidon + TX, butylthiophos + TX, furathiocarb + TX, pyrethroid + TX, octylguanidine salt + TX, octylguanidine acetate + TX, sodium tetrathiocarbonate + TX, benzylfenthion + TX, HCH + TX, HEOD +TX, heptachlor+TX, cypermethrin+TX, HHDN+TX, hydrogen cyanide+TX, quinolinecarb+TX, IPSP+TX, chlorfenapyr+TX, carbochlorin+TX, isodrin+TX, isofenphos+TX, transplanting spirit+TX, rice blast+TX, oxathiophos+TX, juvenile hormone I+TX, juvenile hormone II+TX, juvenile hormone III+TX, chlorpentyl+TX, methoprene+TX, lead arsenate+TX, bromophenylphos+TX, pyralid+TX, thiazophos+TX, m-isopropyl methylcarbamate+TX, Magnesium phosphide + TX, phosphorus azide + TX, methyl azoxyphos + TX, chlorpyrifos + TX, mercurous chloride + TX, methyl sulfoxide + TX, metamizole + TX, metamizole potassium salt + TX, metamizole sodium salt + TX, methylsulfonyl fluoride + TX, butenamidophos + TX, methoprin + TX, methoxychlor + TX, methyl isothiocyanate + TX, methyl chloroform + TX, dichloromethane + TX, oxadiazine + TX, mirex + TX, naphthiophosphate + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, pronicotine + TX, O-5-dichloro-4-iodophenyl O-ethylethylphosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-ylphosphonothioate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-ylphosphonothioate + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, p-dichlorobenzene + TX, methyl parathion + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38+TX, fenthion+TX, parachlorothion+TX, phosphine+TX, methyl phoxim+TX, methamidophos+TX, polychlorinated dicyclopentadiene isomers+TX, potassium arsenite+TX, potassium thiocyanate+TX, precocious plant I+TX, precocious plant II+TX, precocious plant III+TX, amidopyrimidin+TX, fluthrin+TX, fenvalerate+TX, prothiophos+TX, pyraclostrobin+TX, anti-pyrethroid+TX, quassia extract+TX, quinalphos-methyl+TX, oxazolidinone+TX, iodosamide+TX, resmethrin+TX, rotenone+TX, thiamethoxam+TX, ryanodine+TX, sabah+TX, octamidine+TX, clostridium+TX,SI-0009+TX, thiamethoxam+TX, sodium arsenite+TX, sodium cyanide+TX, sodium fluoride+TX, sodium hexafluorosilicate+TX, sodium pentachlorobenzene oxide+TX, sodium selenate+TX, sodium thiocyanate+TX, sulfanilamide+TX, sulfanilamide sodium+TX, sulfuryl fluoride+TX, sulfamethoxam+TX, tar+TX, thiamethoxam+TX, TDE+TX, butylpyrimidophos+TX, temephos+TX, cypermethrin+TX, tetrachloroethane+TX, thiochlorvos+TX, cypermethrin+TX, cypermethrin oxalate+TX, cypermethrin+TX, cypermethrin sodium+TX, tralomethrin+TX, permethrin+TX, triazolam+TX, chlorpyrifos-3+TX, chlorpyrifos+TX X, cyclohexanil + TX, triflumethocarb + TX, chlorpyrifos-butyl + TX, methoprene + TX, veratridine + TX, veratridine + TX, XMC + TX, ζ-cypermethrin + TX, zinc phosphide + TX, oxathiapiprolin + TX, chlorfluanidine + TX, tetrafluanidine + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferric phosphate + TX, niclosamide-ethanolamine + TX, tributyltin oxide + TX, pyrimorph + TX, spiromorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropylene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methyl- Tannin + TX, 5-methyl-6-thio-1,3,5-thiadiazin-3-yl acetic acid + TX, 6-isopentenylaminopurine + TX, fluphenyladenine + TX, thiazolinone + TX, cytokinin + TX, DCIP + TX, furfural + TX, clofafonate + TX, kinetin + TX, verrucous mycorrhizal composition + TX, tetrachlorothiophene + TX, xylenol + TX, zeatin + TX, potassium ethylxanthate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, giant knotweed extract + TX, α-chlorohydrin + TX, antoclopramide + TX, barium carbonate + TX, bismuth urea + TX, brodifacoum + TX, brodifacoum + TX, brodifacoum + TX, chlorfenapyrone + TX, cholecalciferol Alcohol + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, chlorfenapyr + TX, calciferol + TX, flufenapyr + TX, fluoroacetamide + TX, flufenapyr + TX, flufenapyr hydrochloride + TX, chlorfenapyr + TX, chlorfenapyr + TX, phosphorus + TX, chlorfenapyr + TX, chlorfenapyr + TX, scilla glycoside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, chlorfenapyr + TX, -2-(2-butoxyethoxy)ethyl piperonate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol with nerolidol + TX, synergistic acetyl ether + TX, MGK 264 + TX, piperonyl butoxide + TX, synergistic aldehyde + TX, propyl isomer + TX,S421+TX, Zengxiaosan+TX, Sesamine+TX, Sulfoxide+TX, Anthraquinone+TX, Copper naphthenate+TX, Copper oxychloride+TX, Dicyclopentadiene+TX, Silen+TX, Zinc naphthenate+TX, Ziram+TX, Imanin+TX, Ribavirin+TX, Chloroindolehydrazide+TX, Mercuric oxide+TX, Thiophanate-methyl+TX, Azaconazole+TX, Triconazole+TX, Fuconazole+TX, Cyproconazole+TX, Difenoconazole+TX, Diniconazole+TX, Fluepiconazole+TX, Fenbuconazole+TX, Fluquinconazole+TX, Flusilazole+TX, Flutriafol+TX, Furapyram+TX, Hexaconazole+TX, Imazalil+TX, Imidazole+TX, Ipconazole+TX, Meconazole+TX, Myclobutanil+TX X, paclobutrazol + TX, blastifungin + TX, penconazole + TX, prothioconazole + TX, pyraclostrobin + TX, prochloraz + TX, propiconazole + TX, pyraclostrobin + TX, silyfloxacin + TX, tebuconazole + TX, fluconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, trichlorfon + TX, pyrimidine + TX, chlorfenapyr + TX, flufenapyr + TX, pyrimidine ... +TX, R-metalaxyl+TX, furamide+TX, oxadixyl+TX, carbendazim+TX, imidacloprid+TX, maisinin+TX, thiabendazole+TX, ethoxyconazole+TX, sclerotinol+TX, foramicloprid+TX, procymidone+TX, vinclozolin+TX, boscalid+TX, carboxin+TX, furamide+TX, flutolanil+TX, mefenamic acid+TX, oxycarboxin+TX, penthiopyrad+TX, thiofuran+TX, dodine+TX, biguanide+TX, azoxystrobin+TX, kystrobin+TX, enestrobin+TX, enestrobin+TX, flutolanil+TX, fluoxastrobin+TX, kystrobin+TX, oxathiocarb+TX, trifloxystrobin+TX, trifloxystrobin+TX, picoxystrobin +TX, pyraclostrobin+TX, pyraclostrobin+TX, pyraclostrobin+TX, ferbam+TX, mancozeb+TX, maneb+TX, maneb+TX, maneb+TX, methyl propineb+TX, maneb+TX, captol+TX, captan+TX, pyraclostrobin+TX, folpet+TX, tolylfluanid+TX, Bordeaux mixture+TX, copper oxide+TX, mancozeb+TX, quinoline copper+TX, phthalostrobin+TX, kefansan+TX, pyraclostrobin+TX, chlorpyrifos+TX, chlorpyrifos-methyl+TX, chlorpyrifos+TX, benzathiapiprolin+TX, blasticidin-S+TX, chlorpyrifos+TX, chlorothalonil+TX, cyfluanid+TX, cymoxanil+TX, triflupyridam+TX, diclofenac+TX,pyraclostrobin + TX, chloranil + TX, diethofencarb + TX, dimethomorph + TX, flumorph + TX, dithianon + TX, ethaboxam + TX, thiabendazole + TX, famoxadone + TX, fenamidone + TX, blastamide + TX, pyraclostrobin + TX, fluazinam + TX, fluopyram + TX, fluopyram + TX, fluopyram + TX, sulfaquinoxaline + TX, fluopyram + TX, fenacet + TX, fosetyl-aluminum + TX, oxamoxadone + TX, propineb + ​​TX, cyazolin + TX, sulfaquinoxaline + TX, mefenacet + TX, pencycuron + TX, phthalide + TX, polyoxin + TX, propamocarb + TX, pyrimidine + TX, iodoquinoxaline + TX, pyroquilon + TX, fenpyraclostrobin + TX, quinoxaline Oxychloride + TX, pentachloronitrobenzene + TX, thiazolin + TX, imidazolin + TX, tricyclazole + TX, triazolin + TX, validamycin + TX, valeron + TX, zoxamide + TX, dimethomorph + TX, fluphenazine + TX, pyraclostrobin + TX, fluopicolide + TX, benzovinfluazide + TX, fluopicolide + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isopropyram + TX, isothiopyram + TX, thiazolinone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiano[1,2-c]isothiazole -3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, flufenoxam + TX, carbofuran (j iaxiangjunzhi) + TX, chlorophenyl ether amide + TX, dichlorothiazide + TX, toluenestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl) quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]propan-2-ol + TX, thiabendazim + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid tert-butyl ester + TX, bifenthrin + TX, indopoxycillin + TX, carbamate fungicide (trolprocarb) + TX, chlorfluanidazole + TX, isotrifluanid + TX,2-(Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazole- 4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate + TX, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridinyl]carbamic acid but-3-ynyl ester + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, flubendiamide + T X, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyraclostrobin + TX, pyraclostrobin + TX, indazolesulfamide + TX, Flupyraclostrobin + TX, (Z, 2E) -5- [1- (4-chlorophenyl) pyrazol-3-yl] oxy-2-methoxyimino-N, 3-dimethyl-pent-3-enamine + TX, diflupyrazol + TX, pyrazolamide + TX, pyrimidine + TX, isobutylethoxyquinoline + TX, isopropylquinoline + TX, flupyrazolamide + TX, isopropylthiopyrad + TX, 1- [[4- [[2- (trifluoromethyl) -1,3-dioxolane-2-yl] methoxy] phenyl] methyl] pyrazole-3-carboxylic acid ethyl ester + TX (can be made from WO 2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enyloxy]phenyl]methyl]pyrazole-3-carboxylic acid ethyl ester + TX (can be prepared by the method described in WO 2020 / 056090), N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamic acid methyl ester + TX (can be prepared by the method described in WO 2020 / 097012),Methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate + TX (can be prepared by the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (can be prepared by the method described in WO 2020 / 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 (can be prepared by the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide + TX (can be prepared by the method described in 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, benzathiostrobin + TX, cyproconazole + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flutoxazolin + TX, fluthiazolinone + TX, fluopyram + TX, pyridinamide + TX, tetrazolium pyridine + 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, tetrazolylpyrazol + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'- phenyl]-4-yl]-5-pyrimidinemethanol+TX, fluoxathiocarb+TX, enestrobin+TX, (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester+TX, (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoic acid methyl ester+TX, (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoic acid methyl ester+TX,(Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoic acid methyl ester + TX, (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoic acid methyl ester + TX (these compounds can be prepared by WO 2020 / 079111), (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester + TX, (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester + TX (these compounds can be prepared by the method described in WO2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1- 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-ethyl + TX, cloves oxathiocarb + TX, zhongshengmycin + TX, thiophanate-methyl + TX, thiophanate zinc + TX, amitolin (amectotractin) + TX, iprodione + TX, cinclostrobin + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridinyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine+TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-ethyl-N-methyl-formamidine+TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridinyl]-N-isopropyl-N-methyl-formamidine+TX (these compounds can be prepared by WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridinyl]-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 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 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- Formamide + 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 + T X, 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 made from WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline+TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline+TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX,4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline+TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline+TX (these compounds can be prepared by WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline+TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline+TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline+TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline+TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole+TX (these compounds can be prepared by WO 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide+TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+TX, )-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide+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]propionamide+TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 5,5-dimethyl-2-[[4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one+TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester+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 WO 2017 / 055473,Prepared by the methods described in WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol+TX (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester + TX (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone + TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide+TX (this compound can be prepared by 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 WO2016 / 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 WO2014 / 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 WO2017 / 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 WO2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester + TX (this compound can be prepared by the method described in WO2018 / 158 365); 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-carbonimido]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide+TX (these compounds can be prepared by the method described in WO 2018 / 202428);

[0710] Microorganisms, including: Acinetobacter lwoffii + TX, Acremonium alternifolium + TX + TX, Cephalosporium acremonium + TX + TX, Acremonium diospyri + TX, Acremonium obclavatum + TX, AdoxGV +TX, Agrobacterium radioactive strain K84 +TX, Alternaria +TX, Alternaria cassia +TX, Alternaria destruens +TX, Parasitoid spores +TX, Aspergillus flavus AF36 +TX, Aspergillus flavus NRRL 21882 +TX, Aspergillus species +TX, Aureobasidium pullulans +TX, Azospirillum ( TAZO )+TX, nitrogen-fixing bacteria+TX, Azotobacter chroocuccum +TX, nitrogen-fixing bacteria cysts (Bionatural Blooming )+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 TM , formerly known as )+TX, Bacillus licheniformis strain 3086 ( Green )+TX, Bacillus circulans+TX, Bacillus firmus +TX, Bacillus firmus strain I-1582 +TX, Bacillus macerans +TX, Bacillus marismortui +TX, Bacillus megaterium +TX, Bacillus mycoides strain AQ726 +TX, Milky Spore )+TX, Bacillus pumilus species+TX, Bacillus pumilus strain GB34 (Yield )+TX, Bacillus pumilus strain AQ717+TX, Bacillus pumilus strain QST 2808( Ballad )+TX, Bacillus sphaericus +TX, Bacillus species +TX, Bacillus strain AQ175 +TX, Bacillus strain AQ177 +TX, Bacillus strain AQ178 +TX, Bacillus subtilis strain QST 713 +TX, Bacillus subtilis strain QST 714 +TX, Bacillus subtilis strain AQ153+TX, Bacillus subtilis strain AQ743+TX, Bacillus subtilis strain QST3002+TX, Bacillus subtilis strain QST3004+TX, Bacillus subtilis variant strain FZB24 +TX, Bacillus thuringiensis Cry 2Ae+TX, Bacillus thuringiensis Cry1Ab+TX, Bacillus thuringiensis aizawai GC 91 +TX, Bacillus thuringiensis israelensis +TX, Bacillus thuringiensis kurstaki ( Scutella Turilav Dipel )+TX, Bacillus thuringiensis Kurstak BMP123 +TX, Bacillus thuringiensis Kurstak HD-1 (Bioprotec-CAF / )+TX, Bacillus thuringiensis strain BD#32+TX, Bacillus thuringiensis strain AQ52+TX, Bacillus thuringiensis var.aizawai +TX, bacteria spp. +TX, Clavipacter michiganensis phage +TX, +TX, Beauveria bassiana ( Brocaril )+TX, Beauveria bassiana GHA (Mycotrol Mycotrol )+TX, Beauveria brongniartii ( Schweizer )+TX, Beauveria spp.+TX, Botrytis cineria+TX, Bradyrhizobium japonicum +TX, Brevibacillus brevis +TX, Bacillus thuringiensis tenebrionis +TX, BtBooster+TX, Burkholderia cepacia ( Blue )+TX, Burkholderia gladii+TX, Burkholderia gladioli+TX, Burkholderia spp.+TX, Canadian thistle fungus (CBH Canadian )+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 +TX, Candida sake +TX, Candida spp. +TX, Candida tenius +TX, Cedecea dravisae +TX, Cellulomonas flavigena +TX, Chaetomium cochliodes +TX, Chaetomium globosum +TX, Chromobacterium subtsugae strain PRAA4-1T +TX, Cladosporium cladosporioides +TX, Cladosporium oxysporum +TX, Cladosporium chlorocephalum +TX, Cladosporium spp. +TX, Cladosporium tenuissimum +TX, Clonostachys rosea +TX, Colletotrichum acutatum +TX, Coniothyrium minitans (Cotans )+TX, Coniothyrium spp.+TX, Cryptococcus albidus +TX, Cryptococcus humicola +TX, Cryptococcus infirmo-miniatus +TX, Cryptococcus laurentii +TX, Cryptophlebia leucotreta granulovirus +TX, Cupriavidus campinensis +TX, Cydia pomonella granulovirus +TX, codling moth granulosis virus ( Max, Carpovirusine )+TX, Cylindrobasidium laeve +TX, Cylindrocladium +TX, Debaryomyces hansenii +TX, Drechslera hawaiinensis +TX, Enterobacter cloacae +TX, Enterobacteriaceae +TX, Entomophtora virulenta +TX, Epicoccum nigrum +TX, Epicoccum purpurascens +TX, Epicoccum species +TX, Filobasidium floriforme +TX, Fusarium acuminate +TX, Fusarium chlamysporum +TX, Fusarium oxysporum ( / Biofox )+TX, Fusarium spp.+TX, Fusarium species+TX, Galactomyces geotrichum+TX, Gliocladium catenulatum +TX, Gliocladium roseum +TX, Gliocladium species +TX, Gliocladium virens +TX, granulovirus +TX, Halobacillus halophilus +TX, Halobacillus litoralis +TX, Halobacillus trueperi +TX, Halomonas species +TX, Halomonas subglaciescola +TX, Halovibrio variabilis +TX, Hansenula vitis +TX, Helicoverpa armigera nuclear polyhedrosis virus +TX, Spodoptera nucleus polyhedrosis virus +TX, isoflavone-formononetin +TX, Kloeckner's yeast +TX, Kloeckner's yeast species +TX, Lagenidium giganteum +TX, Lecanicillium longisporum +TX, Lecanicillium muscarium +TX, Lymantria dispar nuclear polyhedrosis virus +TX, Halococcus halophilus +TX, Meira geulakonigii +TX, Metarhizium anisopliae +TX, Metarhizium anisopliae (Destruxin )+TX, Metschnikowia fruticola +TX, Metschnikowiapulcherrima +TX, Microdochium dimerum +TX, Micromonospora coerulea +TX, Microsphaeropsis ochracea +TX, foul-smelling white fungus 620 +TX, malodorous rose fungus strain A3-5+TX, Mycorrhizae spp. ( Root )+TX, Myrotheca verrucosa strain AARC-0255 +TX、BROS +TX, Ophiostoma piliferum strain D97 +TX, Paecilomyces farinosus +TX, Paecilomyces fumosorum +TX, Paecilomyces linacinus (Biostat )+TX, Paecilomyces lilacinus strain 251 (MeloCon )+TX, Paenibacillus polymyxa+TX, Pantoea agglomerans (BlightBan )+TX, Pantoea species+TX, Pasteurella species +TX, Pasteuria nishizawae +TX, Penicillium chrysogenum +TX, Penicillium billai +TX, Penicillium breviscompactum +TX, Penicillium spp. +TX, Penicillium chrysogenum +TX, Penicillium purpurogenum +TX, Penicillium species +TX, Penicillium viridiflorum +TX, Phlebiopsis gigantean +TX, phosphate-solubilizing bacteria +TX, Cryptophyton+TX, Phytophthora palmatum +TX, Pichia anomala +TX, Pichia guilermondii +TX, Pichia membranaceus +TX, Pichia nail +TX, Pichia stipitis +TX, Pseudomonas aeruginosa +TX, Pseudomonas aureofasciens (Spot-Less )+TX, Pseudomonas cepacia+TX, Pseudomonas chlororaphis +TX, Pseudomonas corrugate +TX, Pseudomonas fluorescens strain A506 (BlightBan )+TX, Pseudomonas putida+TX, Pseudomonas reactans+TX, Pseudomonas species+TX, Pseudomonas syringae +TX, Pseudomonas aureus +TX, Pseudomonas fluorescens +TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex )+TX、Puccinia canaliculata+TX、Puccinia thlaspeos (Wood )+TX, Pythium paroecandrum+TX, Pythium oligandrum +TX, Pythium entangled +TX, Rhanella aquatilis +TX, Rhanella spp. +TX, Rhizobia +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 +TX, Scytalidium spp.+TX, Scytalidium uredinicola+TX, Spodoptera exigua nuclear polyhedrosis virus +TX, Serratia marcescens +TX, Serratia plymuthica +TX, Serratia spp. +TX, Sordaria fimicola +TX, Spodoptera littoralis nucleopolyhedrovirus +TX, Sporobolomyces roseus +TX, Stenotrophomonas maltophilia +TX, Streptomyces ahygroscopicus +TX, Streptomyces albaduncus +TX, Streptomyces exfoliates +TX, Streptomyces galbus +TX, Streptomyces griseoplanus +TX, Streptomyces griseoviridis +TX, Streptomyces lydicus +TX, Streptomyces lydicus WYEC-108 +TX, Streptomyces violaceus +TX, Tilletiopsis minor +TX, Tilletiopsis spp. +TX, Trichoderma asperellum (T34 )+TX, Trichoderma gamsii +TX, Trichoderma atroviride +TX, Trichoderma hamatum TH 382 +TX, Trichoderma harzianum rifai +TX, Trichoderma harzianum T-22 ( PlantShield )+TX, Trichoderma harzianum T-39 +TX, Trichoderma inhamatum +TX, Trichoderma koningii +TX, Trichoderma spp. LC 52 +TX, Trichoderma lignorum +TX, Trichoderma longibrachiatum +TX, Trichoderma polysporum (Binab )+TX, Trichoderma taxi+TX, Trichoderma virens+TX, Trichoderma virens (formerly known as Gliocladium virens GL-21) +TX, Trichoderma viride +TX, Trichoderma viride strain ICC 080 +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 +TX, Ustilago maydis +TX, various bacteria and supplemented micronutrients (Natural )+TX, various fungi (Millennium )+TX, Verticillium chlamydosporium+TX, Verticillium lecanii +TX、Vip3Aa20 +TX, Virgibaclillus marismortui +TX, Xanthomonas campestris pv. Poae +TX, Xenorhabdus burnetii+TX, Xenorhabdus nematophila+TX;

[0711] Plant extracts including: pine oil +TX, Azadirachtin (PlasmaNeem ), Plant IGR +TX, canola oil (Lilly Miller )+TX, Chenopodium ambrosioides near ambrosioides +TX, chrysanthemum extract +TX, neem oil extract +TX, Labiatae essential oil +TX, clove-rosemary-peppermint and thyme oil extracts (Garden insect )+TX, betaine +TX, garlic +TX, lemongrass oil +TX, neem oil +TX, catnip (Nepeta cataria) (catnip oil) +TX, Nepeta catarina +TX, nicotine +TX, oregano oil +TX, Pedaliaceae oil +TX, Pyrethrum+TX, Soapbark Tree (Quillaja saponaria) +TX, Giant knotweed +TX, rotenone (Eco )+TX, Rutaceae plant extract +TX, soybean oil (Ortho )+TX, Melaleuca alternifolia extract (also known as tea tree oil) (Timorex )+TX, thyme oil+TX, MMF+TX, +TX, Rosemary-Sesame-Peppermint-Thyme and Cinnamon Extract Blend (EF )+TX, clove-rosemary and peppermint extract mixture (EF )+TX, Clove-Peppermint-Garlic Oil and Mint Blend (Soil )+TX, kaolin +TX, storage glucan of brown algae +TX;

[0712] Pheromones including: 3M Sprayable Blackheaded Fireworm )+TX, codling moth pheromone (Paramount dispenser-(CM) / Isomate )+TX, Grape Leaf Roller Pheromone (3M MEC-GBM Sprayable )+TX, leaf roller pheromone (3M MEC-LR Sprayable )+TX, housefly pheromone (Muscamone)(Snip7Fly Starbar Premium Fly )+TX, 3M oriental fruitmoth sprayable )+TX, Peachtree Borer pheromone +TX, Tomato Pinworm Pheromone (3M Sprayable )+TX, Entostat powder (from palm tree extract) (Exosex )+TX、(3E,8Z,11Z)-3,8,11-tetradecatriene 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、 +TX, +TX、Check- +TX, Lavandulylsenecioate+TX;

[0713] Macrobial agents include: Aphidius ervi + TX, Aphidius ervi (Aphelinus- )+TX、Acerophagus papaya+TX、Adalia- )+TX, Coccinella bispotata +TX, Coccinella bispotata +TX, Ageniaspiscitricola+TX, Amblyseius andersoni ( Andersoni- )+TX, Amblyseius californicus +TX, Amblyseius cucumber mite ( Bugline )+TX, Pseudo-Amblyseius +TX, Bugline Swirskii- )+TX, Amblyseius osbornei +TX, Amitus hesperidum +TX, Anagrus atomus +TX, Anagyrus fusciventris +TX, Anagyrus kamali +TX, Anagyrus loecki +TX, Anagyrus pseudococci +TX, Red wax scale flat-horned jumping wasp (Anicetus benefices) +TX, Golden wasp (Anisopteromalus calandrae) +TX, Woodland flower stink bug (Anthocoris nemoralis) (Anthocoris- )+TX, short-spurred aphid wasp +TX, Aphelinusasychis +TX, Aphidius colemani +TX, Alphididae +TX, tobacco aphid wasp+TX, peach red aphid wasp +TX, aphid-eating gall midge +TX, aphid-eating gall midge +TX, Lingnan yellow aphid wasp +TX, Indian yellow aphid wasp +TX, Aprostocetus hagenowii +TX, Atheta coriaria +TX, Bombus species +TX, European bumblebee (Natupol )+TX, European bumblebee +TX, Cephalonomia stephanoderis+TX, Black-backed Ladybird (Chilocorus nigritus)+TX, Common Lacewing (Chrysoperla carnea) +TX, Common Lacewing +TX, Chrysoperla rufilabris +TX, Cirrospilusingenuus +TX, Cirrospilus quadristriatus +TX, Citrostichus phyllocnistoides +TX, Closterocerus chamaeleon +TX, Closterocerus species +TX, Coccidoxenoides perminutus +TX, Coccophagus cowperi+TX, Coccophagus lycimnia+TX, Cottontail wasp (Coccophagus lycimnia)+TX, Cottontail wasp (Coccophagus lutescens)+TX, Cottontail wasp (Coccophagus lutescens)+TX, +TX, Japanese square-headed beetle+TX, Siberian gnathostome +TX, Siberian gnathostome +TX, Pea leafminer +TX, small black ladybug (Delphastus catalinae) +TX, Delphastus pusillus+TX, Diachasmimorpha krausii+TX, Diaparsis jucunda+TX, Diaphorencyrtus aligarhensis+TX, Diaphorencyrtus aligarhensis+TX, Diaphorencyrtus spp.+TX, Diaphorencyrtus spp. +TX, Siberian Braconidia +TX, Encarsia species+TX, Encarsia longita +TX, Encarsia spp. En- )+TX, Eretmocerus eremicus +TX, Encarsia guadeloupae +TX, Encarsia haitiensis +TX, Slender hoverfly +TX, Eretmoceris siphonini+TX, Eretmocerus californicus+TX, Eretmocerus eremicus( Eretline )+TX, Eretmocerus eremicus +TX, Heinrichthys hymenoptera+TX, Monterey's hymenoptera +TX, Eretmocerussiphonini+TX, Four-spotted Ladybird (Exochomus quadripustulatus)+TX, Mite-eating Gall Midge (Feltiella acarisuga) +TX, Acarina +TX, Alishan ceratitivorus +TX, Fopiusceratitivorus +TX, Wirless )+TX, thrips slender waist +TX, Galendromus occidentalis +TX, Goniozus legneri +TX, Echinops serratus +TX, Harmonia axyridis +TX, Heterorhabditis species (Lawn )+TX, Heterorhabditis elegans (NemaShield )+TX, Heterorhabditis megidis (Nemasys BioNem Exhibitline Larvanem- )+TX, Hippodamiaconvergens+TX, Hypoaspis aculeifer (Aculeifer- Entomite- )+TX、Hypoaspis miles(Hypoline Entomite- )+TX, Lbalia leucospoides+TX, Lecanoideus floccissimus+TX, Lemophagus errabundus+TX, Leptomastidea abnormis+TX, Leptomastix dactylopii +TX, Leptomastix epona+TX, Lindorus lophanthae+TX, Lipolexis oregmae+TX, Lucilia caesar +TX, Lysiphlebus testaceipes +TX, Macrolophus caliginosus (Mirical- Macroline )+TX, Mesoseiulus longipes+TX, Metaphycus flavus+TX, Metaphycus lounsburyi+TX, Micromusangulatus +TX, Microterys flavus +TX, Muscidifurax raptorellus and Spalangia cameroni +TX, Neodryinustyphlocybae+TX, Neoseiulus californicus+TX, Neoseiuluscucumeris +TX, Neoseiulus fallacis +TX, Nesideocoris tenuis +TX, bronze black fly (Ophyraaenescens) +TX, Orius insidiosus (Thripor- Oriline )+TX、Orius laevigatus (Thripor- Oriline )+TX、Oriline )+TX、Orius strigicollis (Thripor- )+TX, Pauesia juniperorum+TX, Pediobius foveolatus+TX, Phasmarhabditis hermaphrodita +TX, Phymastichus coffea+TX, Phytoseiulus macropilus+TX, Phytoseiulus persimilis ( Phytoline )+TX, Podisus maculiventris +TX, Pseudacteon curvatus+TX, Pseudacteon obtusus+TX, Pseudacteon tricuspis+TX, Pseudaphycus maculipennis+TX, Pseudleptomastix mexicana+TX, Psyllaephagus pilosus+TX, Psyttalia concolor (complex)+TX, Quadrastichus spp.+TX, Rhyzobius lophanthae+TX, Rodolia cardinalis+TX, Rumina decollate+TX, Semielacher petiolatus+TX, Sitobion avenae +TX, Steinernema carpocapsae (Nematac BioNem )+TX, Steinernema carinata ( Nemasys BioNem Steinernema- Exhibitline )+TX, Steinernema kraussei (Nemasys BioNem Exhibitline )+TX, Steinernema riobrave +TX, Steinernema scapterisci (Nematac )+TX, Steinernema spp.+TX, Steinernematid species (Guardian )+TX, Stethorus punctillum +TX, Tamarixia radiate +TX, Tetrastichus setifer +TX, Thropobius semiluteus +TX, Torymus sinensis +TX, Tricholine )+TX, Trichogrammabrassicae (Tricho- )+TX, Trichogramma evanescens+TX, Trichogramma minutum+TX, Trichogramma ostriniae+TX, Trichogramma platneri+TX, Trichogramma pretiosum+TX, Xanthopimpla stemmator+TX;

[0714] Other biological agents, including: abscisic acid + TX, +TX, Chondrostereum purpureum (Chontrol )+TX, Colletotrichum spondyloticum +TX, copper octanoate +TX, Delta trap (Trapline )+TX, Erwinia amylovora (Harpin) ( Ni-HIBIT Gold )+TX, fatty acids derived from natural by-products of extra virgin olive oil +TX, ferric phosphate +TX, Funnel trap (Trapline )+TX、 +TX, Grower's +TX, Homo-brassonolide +TX, Ferric Phosphate (Lilly Miller Worry Free Ferramol Slug & Snail )+TX、MCP hail trap (Trapline )+TX、parasitic insects Microctonus hyperodae+TX、Mycoleptodiscus terrestris(Des- )+TX、 +TX, +TX, +TX, Pheromone Net (Thripline )+TX, potassium bicarbonate +TX, potassium salt of fatty acids +TX, potassium silicate solution (Sil- )+TX, potassium iodide+potassium thiocyanate +TX、SuffOil- +TX, spider venom +TX, locust microsporidia (Semaspore Organic Grasshopper )+TX, Trapline Rebell )+TX and capture (Takitrapline y+ )+TX;

[0715] (1) An antibacterial agent selected from the group consisting of:

[0716] (1.1) Bacteria, examples of which are Bacillus mojavensis strain R3B (accession number NCAIM (P) B001389) (WO 2013 / 034938), from Certis USA LLC +TX; Bacillus pumilus, in particular strain BU F-33, with NRRL accession number 50185 (from BASF); EPA registration number 71840-19) + TX; Bacillus subtilis, in particular strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, with NRRL registration number B21661, U.S. Patent No. 6,060,051) + TX; Bacillus subtilis strain BU1814 (from BASF SE PLUS, FLEX and EXTRA) + TX; Bacillus subtilis variant amyloliquefaciens strain FZB24, with registration number DSM 10271 (available as or ECO (EPA registration number 70127-5) obtained from Novozymes) + TX; Bacillus subtilis CX-9060 + TX from Certis USA LLC; Bacillus species, specifically strain D747 (available as DOUBLE obtained from Kumiai Chemical Industry Co., Ltd.) with accession number FERM BP-8234, U.S. Patent No. 7,094,592+TX; Paenibacillus sp. strains with accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297+TX; Paenibacillus polymyxa, particularly strain AC-1 (e.g., from Green Biotech Company Ltd.) ) + TX; Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available as BLOOMTIME BIOLOGICAL TM FD BIOPESTICIDE (from Northwest Agri Products) + TX; Pseudomonas proradix (e.g., from Sourcon Padena) )+TX; and

[0717] (1.2) Fungi, examples of which are Aureobasidium pullulans, in particular blastospores of strain DSM 14940, blastospores of strain DSM 14941 or a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g., blastospores from bio-ferm, Switzerland). and BLOSSOM )+TX; Pseudozyma aphidis (as disclosed in WO 2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem)+TX; Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 (as disclosed in WO 2010 / 086790, from Lesaffre et Compagnie, France)+TX;

[0718] (2) Biofungicides selected from the group consisting of:

[0719] (2.1) Bacteria, an example of which is Agrobacterium radiobacterium strain K84 (e.g. GALLTROL- )+TX; radiobacterium strain K1026 (e.g. NOGALL from BASF TM )+TX; Bacillus subtilis variant amyloliquefaciens strain FZB24, with registration number DSM 10271 (available as or ECO (EPA registration number 70127-5) obtained from Novozymes) + TX; Bacillus amyloliquefaciens, specifically strain D747 (available as Double Nickel TM obtained from Kumihiko Chemical Industries, Ltd., with 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, WO 2014 / 028521) (from Marrone Bio Innovations )+TX; Bacillus amyloliquefaciens strain FZB42, registration number DSM 23117, (can be used as from ABiTEP, Germany) + TX; Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria); TM )+TX; Bacillus licheniformis, in particular strain SB3086, having accession number ATCC 55406, WO 2003 / 000051 (available as Biofungicides and Green Release TM Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation) (WG) and (WP)) + TX; Bacillus methylotrophicus strain BAC-9912 (from the Institute of Applied Ecology, Chinese Academy of Sciences) + TX; Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938), from Certis USA, Inc. + TX; Bacillus mycoides isolate with accession number B-30890 (available as BMJ or WG and LifeGard TM obtained from Surtice USA) + TX; Bacillus pumilus, specifically strain QST2808 (available as obtained from Bayer CropScience, USA, with registration number NRRL B-30087 and described in US Pat. No. 6,245,551) + TX; Bacillus pumilus, in particular strain GB34 (available as Yield 1661 and described in U.S. Pat. No. 6,060,051) + TX; Bacillus subtilis, particularly strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP in the United States, having NRRL Accession No. B21661 and described in U.S. Pat. No. 6,060,051) + TX; Bacillus subtilis Y1336 (available as WP was obtained from Bion-Tech, Taiwan, China, and registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX; Bacillus subtilis strain MBI 600 (available as SUBTILEX from BASF, with registration number NRRL B-50595, U.S. Patent No. 5,061,495) + TX; Bacillus subtilis strain GB03 (available as obtained from Bayer AG, Germany) + TX; Bacillus subtilis strain BU1814, (available as PLUS, FLEX and EXTRA obtained from BASF) + TX; Bacillus subtilis CX-9060, obtained from Sertis America, a subsidiary of Mitsui & Co., Ltd. + TX; Bacillus subtilis KTSB strain (obtained from Donaghys )+TX; Bacillus subtilis IAB / BS03 (AVIV from STK Bio-Ag Technologies) TM , from IdaiNature )+TX; Bacillus subtilis strain Y1336 (can be used as WP was obtained from Biotech, Taiwan, China, and registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277) + TX; Paenibacillus epiphyticus (WO 2016 / 020371) from BASF + TX; Paenibacillus polymyxa plantarum species (WO 2016 / 020371) from BASF + TX; Paenibacillus species strains with registration number NRRL B-50972 or registration number NRRL B-67129, WO 2016 / 154297 + TX; Pseudomonas chlororaphis strain AFS009 with registration number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER from AgBiome Innovations, USA). TM and ) + TX; Pseudomonas chlororaphis strains, in particular strain MA342 (e.g., from Bioagri and Koppert); and )+TX; Pseudomonas fluorescens strain A506 (e.g., from NuFarm A506) + TX; Pseudomonas proradix (e.g., from Soconpadna) ) + TX; Streptomyces griseoviridis strain K61 (also known as Streptomyces luteus strain K61) (accession number DSM7206) (from Verdera BioWorks See Crop Protection 2006, 25, 468-475) + TX; Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (ACTINO- and )+TX; and

[0720] (2.2) Fungi, an example of which is Pseudomonas aeruginosa, in particular strain AQ 10 (e.g. AQ from IntrachemBio Italia) ) + TX; Psoralea corylifolia strain AQ10, with accession number CNCM 1-807 (e.g., AQ from Intrachem Biologia Italia S.A. )+TX; Aspergillus flavus strain NRRL21882 (as AFLA- from Syngenta / ChemChina and known products) + TX; budding mold, especially the spores of strain DSM14940 + TX; budding mold, especially the spores of strain DSM 14941 + TX; budding mold, especially the mixture of spores of strains DSM14940 and DSM 14941 (for example, from Bio-Philippe Co., Ltd., Switzerland )+TX; Chaetomium cupreum (accession number CABI 353812) (e.g., BIOKUPRUM from AgriLife TM )+TX; Chaetomium globosum (can be used as from Rivale) + TX; Cladosporium cladosporioides, strain H39, with accession number CBS122244, US2010 / 0291039 (from Wageningen Research Foundation (Stichting DienstLandbouwkundig Onderzoek)) + TX; Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM9660, e.g., from Bayer CropScience Biologics GmbH) + TX; )+TX; Cryptococcus flavescens, strain 3C (NRRL Y-50378), (B2.2.99)+TX; Dactylaria candida+TX; Dilophosphora alopecuri (can be used as TWIST Obtain) + TX; Fusarium oxysporum, strain Fo47 (can be used as obtained from Natural Plant Protection) + TX; Clonospora spp. (synonym: Clonosaceous rosea f. catenulate) strain J1446 (e.g., from Lallemand) )+TX; Glioma rosea (also known as Glioma pink), in particular strain 321U from Adjuvants Plus, strain ACM941 as disclosed in Xue AG (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can. J. Plant Sci. 2003, 83(3):519-524), or strain IK726 (Jensen DF et al. Development of a biocontrol agent for plant disease control with special emphasis on thenear commercial fungal antagonist Clonostachys rosea strain 'IK726' [with particular emphasis on the development of a biocontrol agent for plant disease control using the near-commercial fungal antagonist Gliocladium roseum strain 'IK726'], Australasian Plant Pathol. 2007, 36(2), 95-101) + TX; conidia of Lecanicillium lecanii (formerly Verticillium lecanii) strain KV01 (e.g., from Corbett / Arysta )+TX; Metschnikowia fructicola, in particular strain NRRL Y-30752, (B2.2.3)+TX; Aspergillus ochraceus+TX; Rosy fungus, in particular strain A3-5 (accession number NRRL 30548)+TX; Penicillium steckii (DSM 27859, WO 2015 / 067800) from BASF+TX; Penicillium vermiculatum+TX; VRA 1992 (from Danstar Ferment) C) + TX; Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183 + TX; Pseudomonas flocculentus, strain PF-A22 UL (can be used as L obtained from Plant Products Co., California) + TX; Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell wall (from Lesaffre From BASF ), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 (WO 2010 / 086790) + TX from Lesaffre, France; Simplicillium lanosoniveum + TX; Talaromyces flavus, strain V117b + TX; Trichoderma asperelloides JM41R (registration number NRRL B-50759) (from TRICHO ) + TX; Trichoderma aculeatus, in particular strain kd (e.g., T-Gro from Andermatt Biocontrol) + TX; Trichoderma aculeatus, in particular strain SKT-1, having accession number FERM P-16510 (e.g., ECO- ), strain T34 (e.g., T34 from Biocontrol Technologies SL, Spain) or strain ICC 012+TX from Isagro; Trichoderma aureoviride, in particular strain SC1 (accession number CBS122089, WO 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA), strain 77B (T77 from Andermat Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Ltd.)+TX; Trichoderma aureoviride, strain CNCM 1-1237 (e.g., Sentinel from Agrauxine, France); WP) + TX; Trichoderma viride, strain No. V08 / 002387 + TX; Trichoderma viride, strain NMI No. V08 / 002388 + TX; Trichoderma viride, strain NMI No. V08 / 002389 + TX; Trichoderma viride, strain NMI No. V08 / 002390 + TX; Trichoderma viride, strain LC52 (e.g., Tenet from Agri-Mount Technology Co., Ltd.) + TX; Trichoderma viride, strain ATCC 20476 (IMI 206040) + TX; Trichoderma viride, strain T11 (IMI352941 / CECT20498) + TX; Trichoderma viride, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) 11-253151A + TX; Trichoderma viride, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) 11-253151A+TX; Dark green Trichoderma, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) 11-253151A+TX; Trichoderma fertile (e.g., TrichoPlus from BASF) + TX; Trichoderma germsii (formerly known as green Trichoderma), strain ICC080 (IMI CC 392151CABI, e.g., BioDerma from AGROBIOSOL DE MEXICO, SADE CV) + TX; Trichoderma germsii (formerly known as green Trichoderma), strain ICC 080 (IMI CC 392151CABI) (can be used as obtained from Agribelso Mexico) + TX; Trichoderma harmatum + TX; Trichoderma harmatum, with accession number ATCC 28012 + TX; Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Kobert) or strain Cepa SimbT5 (from Simbiose Agro) + TX; Trichoderma harzianum + TX; Trichoderma harzianum slant (rifai) T39 (e.g., from Makhteshim, USA) )+TX; Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P from Kobert)+TX; Trichoderma harzianum, strain TH35 (e.g., Root-Pro from Mycontrol)+TX; Trichoderma harzianum, strain DB 103 (can be used as T- 7456 from Dagutat Biolab) + TX; Trichoderma polyspora, strain IMI206039 (e.g., Binab TF WP + TX from BINAB Bio-Innovation AB, Sweden); Trichoderma stromaticum, with accession number Ts3550 (e.g., Tricovab from CEPLAC, Brazil) + TX; Trichoderma viride (also known as Gliocladium viride), in particular strain GL-21 (e.g., SoilGard from Certis, USA) + TX; Trichoderma viride strain G-41, formerly known as Gliocladium viride (accession number ATCC 20906) (e.g., from Biovox, USA) PLUS WP and PLUS WP) + TX; Trichoderma viride, strain TV1 (e.g., Trianum-P from Kobert) + TX; Trichoderma viride, in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie [Science of the Agricultural University of Szczecin] 161: 125-137) + TX; a mixture of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012) (with the accession number CABI CC IMI 392716) and Trichoderma gamsii (formerly known as Trichoderma viride) strain ICC 080 (with the accession number IMI 392151) (e.g., BIO-TAM from Esig USA, Inc.TM and from Agriberso Mexico )+TX; Oldman's fine base spore strain U3, having accession number NM 99 / 06216 (e.g., BOTRY- from Botry-Zen Ltd of New Zealand) and from Byworth )+TX; Verticillium albo-atrum (formerly known as V. dahliae), strain WCS850, having accession number WCS850, deposited with the Central Bureau for Fungi Cultures (e.g., by Tree Care Innovations, DUTCH )+TX; Verticillium chlamydosporium+TX;

[0721] (3) Biological control agents having the effect of improving plant growth and / or plant health selected from the following group:

[0722] (3.1) Bacteria, an example of which is Azospirillum brasilense (e.g., from KALO, Inc.) )+TX; Azospirillum lipoferum (e.g., VERTEX-IF from TerraMax, Inc.) TM )+TX; Azorhizobiumcaulinodans, in particular strain ZB-SK-5+TX; Azotobacter chroococcum, in particular strain H23+TX; Azotobacter vinelandii, in particular strain ATCC 12837+TX; a mixture of Azotobacter vinelandii and Clostridium pasteurianum (which can be used as from Agrinos) +TX; Bacillus amyloliquefaciens pm414 (LOLI- from Biofilm Crop Protection) )+TX; Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542, WO 2017 / 205258)+TX; Bacillus amyloliquefaciens TJ1000 (can be used as Bacillus amyloliquefaciens, in particular strain IN937a+TX; Bacillus amyloliquefaciens, in particular strain FZB42 (e.g., from Abbott, Germany). ) + TX; Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015) + TX; EE128 (NRRL No. B-50917) + TX; EE349 (NRRL No. B-50928) + TX; Bacillus cereus, in particular strain BP01 (ATCC 55675, for example, from Arysta Lifescience, USA ) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., from BASF )+TX; Bacillus mycoides BT155 (NRRL No. B-50921)+TX; Bacillus mycoides EE118 (NRRL No. B-50918)+TX; Bacillus mycoides EE141 (NRRL No. B-50916)+TX; Bacillus mycoides BT46-3 (NRRL No. B-50922)+TX; Bacillus pumilus, in particular strain QST2808 (accession number NRRL No. B-30087)+TX; Bacillus pumilus, in particular strain GB34 (e.g., YIELD® from Bayer CropScience, Germany) )+TX; Bacillus siamensis, particularly strain KCTC 13613T+TX; Bacillus subtilis, particularly strain QST713 / AQ713 (having NRRL accession number B-21661 and described in U.S. Patent No. 6,060,051, can be used as OPTI or ASO was obtained from Bayer CropScience in the United States) + TX; Bacillus subtilis, in particular strain AQ30002 (accession number NRRL B-50421 and described in U.S. patent application number 13 / 330,576) + TX; Bacillus subtilis, in particular strain AQ30004 (and NRRL number B-50455 and described in U.S. patent application number 13 / 330,576) + TX; Bacillus subtilis strain BU1814 (available as from BASF), Bacillus subtilis rm303 (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 (can be used as (WG), (WP) obtained from FMC Corporation) + TX; Bacillus subtilis, in particular strain MBI 600 (e.g., from BASF )+TX; Bacillus tequilensis, in particular strain NII-0943+TX; Bradyrhizobium japonicum (e.g., from Novozymes )+TX; Delftia acidovorans, in particular strain RAY209 (e.g., from Brett Young Seeds )+TX; Mesorhizobium cicer (e.g., NODULATOR from BASF)+TX; Lactobacillus species (e.g., Lactobacillus from Latpafi) ) + TX; Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF) + TX; Pseudomonas proradix (e.g., from Soconpadna ) + TX; Pseudomonas aeruginosa, in particular strain PN1 + TX; Rhizobium leguminosarum, in particular Rhizobium vitis vinifera (bv. viceae) strain Z25 (accession number CECT 4585) + TX; Bacillus polymyxa, in particular strain AC-1 (e.g., from Green Biotechnology Co., Ltd. ) + TX; Serratia marcescens, in particular strain SRM (accession number MTCC 8708) + TX; Sinorhizobium meliloti strain NRG-185-1 (from Bayer CropScience GOLD) + TX; Thiobacillus sp. (e.g., from Cropaid Ltd, UK) )+TX; and

[0723] (3.2) Fungi, examples of which are Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Bio) +TX; Penicillium bilaii, strain ATCC 22348 (e.g., from Acceleron BioAg); ), yellow basket fungus (Talaromyces flavus), strain V117b + TX; dark green Trichoderma strain CNCM 1-1237 (for example, from Aglaocosin, France) WP), Trichoderma viride, for example, strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie [Science of the Agricultural University of Szczecin] 161: 125-137) + TX; Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, for example, from Agri-Mountain Technology Ltd. )+TX; dark green Trichoderma strain SC1 (described in WO2009 / 116106)+TX; Trichoderma strain kd (e.g., T-Gro from Andermatt Biocontrol)+TX; Trichoderma asperellum strain (Eco-T from Plant Health Products of New Zealand)+TX, Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Cobert)+TX; Myrotheca verrucosa strain AARC-0255 (e.g., DiTera from Valent Biosciences) TM ) + TX; Penicillium bilaiae strain ATCC ATCCATCC20851 + TX; Pythium lateralis strain M1 (ATCC 38472, for example, Polyversum from Bioprepraty, Czech Republic) + TX; Trichoderma virens strain GL-21 (for example, from the United States of America, the United States )+TX; Verticillium dahliae (formerly Verticillium dahliae) strain WCS850 (CBS276.92, e.g., Dutch Trig from Tree Care Innovations)+TX; Trichoderma aureum, particularly strain No. V08 / 002387, strain No. NMI No. V08 / 002388, strain No. NMI No. V08 / 002389, strain No. NMI No. V08 / 002390+TX; Trichoderma harzianum strain ITEM908, Trichoderma harzianum strain TSTh20+TX; Trichoderma harzianum strain 1295-22+TX; Pythium lateralis strain DV74+TX; Rhizopogon amylopogon (e.g., Myco-Sol from Agri-Enterprise, LLC, formerly known as Helena Chem. Company)+TX; Rhizopogon fulvigleba (e.g., Myco-Sol from Agri-Enterprise, LLC, formerly known as Helena Chemical Company) + TX; Trichoderma virens strain GI-3 + TX;

[0724] (4) Insecticidal biological control agents selected from the following

[0725] (4.1) Bacteria, examples of which are Agrobacterium radiobacterium strain K84 (Galltrol from Egger Biochemicals) + TX; Bacillus amyloliquefaciens, in particular strain PTS-4838 (e.g., AVEO from Hualun Biosciences, USA) + TX; Bacillus firmus, in particular strain CNMC 1-1582 (e.g., from BASF ) + TX; Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA ALLC) + TX; Bacillus sphaericus, particularly serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., from Hualun Biosciences, Inc., USA ) + TX; Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g., from Hualun Biosciences ) + TX; Bacillus thuringiensis subsp. aizawai, particularly serotype H-7 (e.g., from Hualun Biosciences, USA WG) + TX; Bacillus thuringiensis israelensis strain BMP 144 (e.g., from Becker Microbial Products, Inc., Illinois); ) + TX; Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., from Hualun Biosciences, USA )+TX; Bacillus thuringiensis subsp. aizawai strain GC-91+TX; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC from Changzhou Jianghai Chemical Factory)+TX; Bacillus thuringiensis Japonica strain Buibui+TX; Bacillus thuringiensis subsp. Kurstaki strain BMP 123 (from Becker Microbial Products, Illinois)+TX; Bacillus thuringiensis subsp. Kurstaki strain BMP 123 from Becker Microbial Products, Illinois, e.g., BARITONE+TX from Bayer CropScience; Bacillus thuringiensis subsp. Kurstaki strain HD-1 (e.g., from Hualun Biosciences, USA) ES) + TX; Bacillus thuringiensis variant Kurstaki strain EVB-113-19 (e.g., from AEF Global )+TX; Bacillus thuringiensis subsp. Kurstaki strain ABTS 351+TX; Bacillus thuringiensis subsp. Kurstaki strain PB 54+TX; Bacillus thuringiensis subsp. Kurstaki strain SA 11 (from Sertis, USA) )+TX; Bacillus thuringiensis subsp. Kurstaki strain SA 12 (THURICIDE from the United States, Sertis)+TX; Bacillus thuringiensis subsp. Kurstaki strain EG 2348 (from the United States, Sertis )+TX; Bacillus thuringiensis subsp. Kurstaki strain EG7841 (from Sertis, USA )+TX; Bacillus thuringiensis subsp. pseudotelocampi strain NB176 (SD-5428, e.g., from BioFa, Germany) FC) + TX; Brevibacillus laterosporus (from Ecolibrium Biologicals Ltd.) )+TX; Burkholderia species, in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; e.g., MBI206 TGAI and from Maroni Bioinnovations )+TX; Chromobacterium subtsugae, particularly strain PRAA4-1T (e.g., MBI-203; e.g., from Maroni BioInnovations )+TX; Mycoplasma scabies Ve6 (MYCOTAL from Kobert)+TX; Paenibacillus popilliae (formerly known as Bacillus popilliae); such as MILKY SPORE POWDER from St. Gabriel Laboratories TM or Milky Spore Granular TM ) + TX; Pasteurella pseudoszavara strain Pn1 (CLARIVA from Syngenta / China Chemical Corporation) + TX; Serratia entomophila (e.g., Wrightson Seeds) ) + TX; Serratia marcescens, in particular strain SRM (accession number MTCC 8708) + TX; Trichoderma acanthoides (TRICHODERMAX from Novozymes) + TX; Wolbachia pipientis ZAP strain (e.g., ZAP from MosquitoMate) )+TX; and

[0726] (4.2) Fungi, an example of which is Beauveria bassiana strain ATCC 74040 (e.g. from Intrachem Bio, Italy). ) + TX; Beauveria bassiana strain GHA (accession number ATCC74250, e.g., from Laverlam Int. Corp. ES and MYCONTROL- )+TX; Beauveria bassiana strain ATP02 (accession number DSM 24665)+TX; Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus), strain Apopka97, e.g., from SePRO )+TX; Metarhizium anisopliae 3213-1 (deposited under NRRL Accession No. 67074, disclosed in WO 2017 / 066094; Pioneer Hi-Bred International)+TX; Metarhizium robertsii 15013-1 (deposited under NRRL Accession No. 67073)+TX; Metarhizium robertsii 23013-3 (deposited under NRRL Accession No. 67075)+TX; Paecilomyces lilacinus strain 251 (from Sertis, USA )+TX; Zoophtoraradicans+TX;

[0727] (5) A virus selected from the group consisting of: summer fruit tortrix granulovirus (GV) + TX; Cydia pomonella (codling moth) granulovirus (GV) + TX; Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV) + TX; Spodoptera exigua (beet armyworm) mNPV + TX; Spodoptera frugiperda (fall armyworm) mNPV + TX; Spodoptera littoralis (African cotton moth) NPV + TX;

[0728] (6) Bacteria and fungi selected from the group consisting of Agrobacterium spp. + TX; Rhizobium spp. + TX; Azospirillum spp. + TX; Azotobacter spp. + TX; Bradyrhizobium spp. + TX; Burkholderia spp., in particular 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 spp. tinctorus)+TX; Pseudomonas species+TX; Rhizobium species, especially Rhizobium trifolii+TX; Rhizopogon species+TX; Scleroderma species+TX; Suillus species+TX; Streptomyces species+TX;

[0729] (7) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biocontrol agents, selected from garlic (Allium sativum) (NEMGUARD from Eco-Spray; BRALIC from ADAMA) + TX; Armour-Zen + TX; Artemisia absinthium + TX; azadirachtin (e.g., AZATIN XL from Sertis, USA) + TX; Biokeeper WP + TX; extracts from the Brassicaceae family, in particular rapeseed meal or mustard meal + TX; Cassia nigricans + TX; Celastrus angulatus + TX; Chenopodium anthelminticum + TX; chitin + TX; Dryopteris filix-mas + TX; Equisetum arvense + TX; arvense)+TX; Fortune Aza+TX; Fungastop+TX; Quinoa saponin extract from quinoa seeds (such as HeadsUp plant Protectants from Canada) (quinoa saponins) + TX; naturally occurring Blad peptide extracted from lupin seeds (from Certis EU ) + TX; naturally occurring Blad polypeptide extracted from lupin seeds (from FMC )+TX; Pyrethrum / Pyrethrins+TX; Quassia amara+TX; Quercus+TX; Quillaja extract (QL AGRI 35 from BASF)+TX; Giant knotweed extract (from MarroneBio) MAXX)+TX; "Requiem TM "Insecticide" + TX; Rotenone + TX; Ryania / ryanodine + TX; Symphytum officinale + TX; Artemisia selengensis + TX; Thymol + TX; Thymol mixed with Geraniol (CEDROZ from Eden Research) + TX; Thymol mixed with Geraniol and Eugenol (CEDROZ from Eden Research) + TX )+TX; Triact 70+TX; TriCon+TX; Tropaeulum majus+TX; Melaleuca alternifolia extract (TIMOREX from Stockton Corporation (STK) )+TX; Urtica dioica+TX; Veratrin+TX; and Viscum album+TX; and

[0730] Safeners such as fenoxacorb+TX, cloquintocet-mexyl (including cloquintocet-mexyl)+TX, cyclopropylsulfonamide+TX, dichloropropane+TX, fenoxac (including fenoxac-ethyl)+TX, fenoxac+TX, fluazifop+TX, fenoxac+TX, isoxadiazole+TX, isoxadiazole (including isoxadiazole-ethyl)+TX, mefenpyr (including mefenpyr-diethyl)+TX, metcamifen+TX and fenoxaconitrile+TX.

[0731] References in brackets after the active ingredient, e.g. [3878-19-1], refer to Chemical Abstracts Registration Numbers. The mixed partners described above are known. In the case where the active ingredients are included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13th edition; Editor: CDSTomLin; The British Crop Protection Council], they are described therein by the entry number given above in parentheses for the specific compound; e.g. the compound "avermectin" is described by entry number (1). In the case where "[CCN]" is added above to a specific compound, the compound in question is included in the "Compendium of Pesticide Common Names", which can be found on the Internet [A.Wood; Compendiumof PesticideCommonNames ,Copyright 1995-2004]; for example, the compound "acetoprolin" is described on the Internet at http: / / www.alanwood.net / pesticides / acetoprole.html middle.

[0732] Most of the active ingredients described above are referred to by what are referred to as "common names" above, with the corresponding "ISO common name" or another "common name" being used in different cases. If a name is not a "common name," the kind of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, "Chemical Name," "Traditional Name," "Compound Name," or "Research Code" is used, or if neither one of those names nor the "common name" is used, the "synonym" is used. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0733] A trade name in parentheses following an active ingredient refers to one or more commercially available products containing that active ingredient.

[0734] Active ingredient mixtures of a compound of formula (I) selected from the compounds defined in Tables 1 to 5 and Table P and the above-mentioned active ingredients comprise a compound selected from the compounds defined in Tables 1 to 5 and Table P and the active ingredient as described above, preferably in a mixing ratio of from 100:1 to 1:6000, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, very especially from 5:1 and 1:5, particularly preferably in a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 is likewise preferred, especially in a ratio of 1:1, or or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.

[0735] The mixtures as described above may be used in a method for controlling pests which comprises applying a composition comprising a mixture as described above to the pests or their environment, excluding methods for treating the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0736] Mixtures comprising a compound of formula (I) selected from the compounds defined in Tables 1 to 5 and Table P and one or more active ingredients as described above can be applied, for example, in a single "ready-to-use" form, in a combined spray mixture (which consists of separate formulations of the individual active ingredient components, such as a "tank mix"), and in combination when applied in a sequential manner (i.e., one after another within a reasonably short period of time, such as a few hours or days). The order in which the compound of formula (I) and the active ingredients as described above are applied is not critical for the practice of the present invention.

[0737] The compositions according to the invention may also contain other solid or liquid adjuvants, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (for example silicone oils), preservatives, viscosity regulators, adhesives and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0738] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, screening and / or compressing the solid active ingredient; and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliary agents and / or grinding the active ingredient with one or more auxiliary agents. These methods for preparing the compositions and the use of compound I for preparing these compositions are also subject matter of the present invention.

[0739] Methods of applying these compositions, i.e., methods for controlling the aforementioned types of pests, such as spraying, atomizing, dusting, brushing, coating, broadcasting, or pouring - selected to suit the intended purpose in the prevailing situation - and the use of these compositions for controlling the aforementioned types of pests are further subjects of the present invention. Typical concentration rates are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient. The application rate per hectare is generally 1 to 2000 g of active ingredient per hectare, in particular 10 to 1000 g / ha, preferably 10 to 600 g / ha.

[0740] In the field of crop protection, the preferred method of application is application to the leaves of the plants (foliar application), it being possible to select the frequency and rate of application to suit the risk of infestation by the pest in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by saturating the locus of the plants with a liquid composition or by introducing the active ingredient in solid form into the locus of the plants (e.g. into the soil, for example in the form of granules (soil application)). In the case of rice crops, such granules can be metered into flooded rice fields.

[0741] The compound with formula (I) of the present invention and composition thereof are also suitable for the protection of plant propagation materials (such as seeds, such as fruits, tubers or grains, or nursery plants), to resist the harmful organism of above-mentioned type.Can be used before planting, this propagation material is processed, for example, can be processed before sowing, seed.Alternately, can be by being immersed in liquid composition by seed or by applying solid composition layer, this compound is applied to seed grain (coating).Also may be when this propagation material is planted in application site, use these compositions, for example, during drilling, these compositions are applied to seed furrow.These treatment methods for plant propagation materials and the plant propagation materials so processed are other themes of the present invention.Typical treatment ratio will depend on plant to be controlled and harmful organism / fungus, and usually between 1 gram to 200 grams of every 100kg seed, preferably between 5 grams to 150 grams of every 100kg seed, as between 10 grams to 100 grams of every 100kg seed.

[0742] The term seed includes all kinds of seeds and plant propagules including but not limited to true seeds, seed pieces, suckers, kernels, bulbs, fruits, tubers, grains, rhizomes, cuttings, cuttings etc. and in preferred embodiments means true seeds.

[0743] The present invention also includes seeds coated or treated with a compound of formula I or seeds containing a compound of formula I. Although a greater or lesser portion of the ingredient may penetrate into the seed material, depending on the method of application, the term "coated or treated and / or containing" generally means that at the time of application, in most cases, the active ingredient is on the surface of the seed. When the seed product is (re)planted, it can absorb the active ingredient. In an embodiment, the present invention makes it possible to obtain plant propagation material having a compound of formula I attached thereto. Further, thereby making it possible to obtain a composition comprising plant propagation material treated with a compound of formula I.

[0744] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting. Seed treatment with a compound of formula (I) can be applied by any known method, such as spraying or dusting the seeds before sowing or during sowing / planting.

[0745] The compounds of the present invention can be distinguished from other similar compounds by virtue of greater efficacy and / or different pest control at low application rates, which can be distinguished by those skilled in the art using experimental procedures, using lower concentrations (if necessary), such as 10 ppm, 5 ppm, 2 ppm, 1 ppm or 0.2 ppm; or lower application rates, such as 10 ppm per m 2Greater efficacy may be observed through increased safety (to above- and below-ground non-target organisms such as fish, birds, and bees), improved physico-chemical properties, or increased biodegradability.

[0746] In each aspect and embodiment of the present invention, "consisting essentially of and variations thereof are preferred embodiments of "comprising" and variations thereof, and "consisting of and variations thereof are preferred embodiments of "consisting essentially of and variations thereof.

[0747] The disclosure of this application enables every combination of the embodiments disclosed herein.

[0748] It should be noted that the disclosure herein regarding compounds of Formula I also applies to compounds of each of Formulas I-1, I-2, I-3, I-4, I-1a, I-2a, I-3a, I-4a, I-5a, II-1, II-2, II-3, II-4, II-5, V-1, V-2, V-3, V-4, V-5, VI-1, VI-2, VI-3, VI-4, VI-5, VIII-1, VIII-2, VIII-3, VIII-4, VIII-5, XIII-1, XIII-2, XIII-3, XIII-4, XIII-5, XIV-1, XIV-2, XIV-3, XIV-4, XIV-5, XV-1, XV-2, XV-3 or XV-4, as well as the compounds in Tables 1 to 5 and P.

[0749] Examples

[0750] The following examples further illustrate (but do not limit) the present invention.

[0751] The compounds of the invention can be distinguished from known compounds by a greater efficacy at low application rates, which can be demonstrated by a person skilled in the art using the experimental procedures outlined in the examples, using lower application rates (if necessary), for example, 60 ppm, 20 ppm or 2 ppm.

[0752] Throughout this specification, temperatures are given in degrees Celsius (° C.) and “mp.” means melting point. LC / MS means liquid chromatography mass spectrometry, and the apparatus and methods are described as follows

[0753] Recorded on a Bruker 400 MHz spectrometer 1 H NMR and 19 F NMR measurements, chemical shifts relative to TMS ( 1 H) or CFCl3( 19F) Standards are given in ppm. Spectra were measured in deuterated solvents as indicated. The compounds were characterized using any of the following LCMS methods. Characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", reported in minutes) and the measured molecular ion (M+H) + or (MH) - .

[0754] LC-MS and GC-MS methods:

[0755] Method 1:

[0756] Spectra were recorded on a mass spectrometer from Waters (SQD2 or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative switching, capillary: 0.8-3.00 kV, cone range: 25 °C, source temperature: 120°C-150°C, desolvation temperature: 500°C-600°C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110 to 850 Da) and an Acquity UPLC from Waters: quaternary solvent manager, heated column compartment, diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 x 2.1 mm, temperature: 40°C, DAD wavelength range (nm): 200 to 400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 0 min 10% B; 0.min-0.2 min 10%-50% B; 0.2 min-0.6 min 50%-100% B; 0.6-1.3 min 100% B; 1.3 min-1.4 min 100%-10% B; 1.4 min-1.6 min 10% B; flow rate (mL / min) 0.6.

[0757] Method 2:

[0758] Spectra were recorded on a mass spectrometer from Agilent Technologies (6410 triple quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary voltage: 4.00 kV, fragmentor voltage: 100 V, desolvation temperature: 350°C, gas flow: 11 L / min, nebulizer gas: 45 psi, mass range: 110 to 1000 Da) and a 1200 series HPLC from Agilent: quaternary pump, heated column compartment and VWD detector. Column: KINETEX EVO C18, 2.6 μm, 50×4.6 mm, temperature: 40°C, detector VWD wavelength: 254 nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH: gradient: 0 min 10% B, 90% A; 0.9-1.8 min 100% B; 1.8-2.2 min 100% -10% B; 2.2 min -2.5 min 10% B; flow rate (mL / min) 1.8.

[0759] Method 3:

[0760] Spectra were recorded on a mass spectrometer from Agilent Technologies (MSD-IQ mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary voltage: 3.5 kV, fragmentor voltage: 110 V, desolvation temperature: 325°C, gas flow: 13 L / min, nebulizer gas: 55 psi, mass range: 110 to 850 Da) and a 1290 series HPLC from Agilent: quaternary pump, heated column compartment and diode array detector. Column: AGILENTPOROSHELL 120EC-C18, 1.9 μm, 50 x 2.1 mm, temperature: 40°C, DAD wavelength range (nm): 190 to 400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.1% HCOOH: Gradient: 0-0.5 min 10% B, 90% A; 1.2-1.5 min 95% B, 05% A; 1.8-2.5 min 10% B, 90% A; flow rate (mL / min) 0.8.

[0761] Method 4:

[0762] Spectra were recorded on a mass spectrometer from Waters Corporation (SQD, SQDII or QDA single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative, capillary voltage: 0.8-3.00 kV, cone: 5-30 V, source temperature: 120-150° C., desolvation temperature: 350-600° C., cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass range: 110 to 950 Da) and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, temperature: 60°C, DAD wavelength range (nm): 210 to 400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min) 0.85, gradient: 10% B isocratic for 0.2 min, then 10%-100% B in 1.0 min, 100% B isocratic for 0.2 min, 100%-10% B in 0.05 min, 10% B isocratic for 0.05 min.

[0763] Method 5:

[0764] Spectra were recorded on an ACQUITY mass spectrometer (QDa or SQDII single quadrupole mass spectrometer) from Waters equipped with an electrospray source (polarity: positive or negative, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150°C, desolvation temperature: 400°C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLCHSS T3, 1.8 μm, 30×2.1 mm, temperature: 60° C., DAD wavelength range (nm): 210 to 400, solvent gradient: A=water / methanol 9:1+0.1% formic acid, B=acetonitrile+0.1% formic acid, gradient: 0%-100% B in 3.0 min; flow rate (ml / min) 0.75.

[0765] Preparation Examples

[0766]

[0767] The combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain wettable powders which can be diluted with water to give a suspension of the desired concentration.

[0768]

[0769]

[0770] The combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable grinder to obtain a dust that can be used directly for seed treatment.

[0771] Emulsifiable concentrates

[0772]

[0773] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0774]

[0775] A ready-to-use dust is obtained by mixing the combination with a carrier and grinding the mixture in a suitable grinder. Such a dust can also be used for dry seed dressing of seeds.

[0776] Extruder granules

[0777]

[0778] The combination is mixed with the adjuvants and ground, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0779] Coated granules

[0780] Active ingredient 8%

[0781] Polyethylene glycol (molecular weight 200) 3%

[0782] Kaolin 89%

[0783] The finely ground combination is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol. In this way, dust-free coated granules are obtained.

[0784] Suspension concentrates

[0785]

[0786] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such a dilution, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0787] Flowable concentrate for seed treatment

[0788]

[0789] The finely ground combination is intimately mixed with adjuvants to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such a dilution, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0790] Extended-release capsule suspension

[0791] 28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water until the desired particle size is reached. To this emulsion, 2.8 parts of a mixture of 1,6-hexanediamine in 5.3 par...

Claims

1. A compound having formula (I) in: A is O or S; X is N or CR 8 ; Y is N or CR 8 ; Z is N or CR 8 ; The premise is that at least one of X, Y, and Z is N; R 1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6 C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl-C1-C6-alkyl, cyano-heterocycloalkyl, hydroxy-C3-C6-cycloalkyl, C1-C6-alkyl-carbonyloxy-C3-C6-cycloalkyl, C1-C6-alkylsulfonyloxy-C3-C6-cycloalkyl C1-C6-alkyl, C1-C6-alkyloxy-C3-C6-cycloalkyl, C1-C6-haloalkyloxy-C3-C6-cycloalkyl, C1-C6-alkylthio-C3-C6-cycloalkyl, C1-C6-haloalkylthio-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfinyl-C3-C6-cycloalkyl, C1-C6-alkylsulfonyl-C3-C6-cycloalkyl, C1-C6-haloalkylsulfonyl-C3-C6-cycloalkyl, C2-C6-alkynyl-C3-C6-cycloalkyl, C1-C6-alkoxycarbonyl-C3-C6-cycloalkyl, carboxyl-C3-C6-cycloalkyl, carbamoyl-C3-C6-cycloalkyl, C1-C6-alkylaminocarbonyl-C3-C6-cycloalkyl (which may be replaced by R 8 monosubstituted or polysubstituted), C4-C8-bicycloalkyl, C1-C6-alkoxyimino, phenyl (which may be R 10 monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 monosubstituted or polysubstituted), heteroaryl-C3-C6-cycloalkyl (the heteroaryl may be R 10 monosubstituted or polysubstituted), heterocycloalkyl (which may be R 8 substituted), heterocycloalkyl-C1-C6-alkyl (which may be replaced by R 8 substituted) or heterocycloalkyl-C3-C6-cycloalkyl (the heterocycloalkyl may be replaced by R 8 replace); R 2 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, phenyl (which may be replaced by R 10 monosubstituted or polysubstituted), phenyl-C1-C6-alkyl (the phenyl group may be R 10 monosubstituted or polysubstituted), heteroaryl (the heteroaryl may be R 10 monosubstituted or polysubstituted), heteroaryl-C1-C3-alkyl (the heteroaryl may be R 10 monosubstituted or polysubstituted), cyano, cyano-C1-C6-alkyl, cyano-C3-C6-cycloalkyl, hydroxyl, formyl, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-cycloalkylcarbonyl, 10 Mono- or poly-substituted benzoyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyloxycarbonyl, carbamoyl, C1-C6-alkylaminocarbonyl (the amino group may be replaced by R 8 substituted), C1-C6-alkoxycarbonyl C1-C6-alkylamino (the amino group may be R 8 Substituted), C1-C6-alkoxycarbonylamino (the amino group may be R 8 substituted), (C1-C6-alkylthio)carbonyl, (C1-C6-alkyl)thiocarbonyl, (C1-C6-alkoxy)thiocarbonyl, thiocarbamoyl, C1-C6-alkylamino-thiocarbonyl (the amino group may be replaced by R 8 substituted), C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, sulfamoyl, C1-C6-alkylaminosulfonyl (the amino group may be R 8 substituted), C1-C6-alkoxycarbonyl-C1-C6-alkyl, aminocarbonyl-C1-C6-alkyl, C1-C6-alkylaminocarbonyl-C1-C6-alkyl (the amino group may be replaced by R 8 substituted), C3-C6-cycloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 substituted), C1-C6-haloalkylaminocarbonyl-C1-C6-alkyl (the amino group may be R 8 substituted), C1-C6-alkylcarbonyl-C1-C6-alkyl, C1-C6-haloalkylcarbonyl-C1-C6-alkyl, C1-C6-alkylcarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonyloxy-C1-C6-alkyl, C1-C6-alkoxycarbonylamino-C1-C6-alkyl (the amino group may be replaced by R 8 substituted), hydroxyimino, hydroxyamino-C1-C6-alkyl, C1-C6-alkoxyimino, C1-C6-alkoxyimino-C1-C6-alkyl or C1-C6-haloalkoxyimino-C1-C6-alkyl; R 3 is halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C1-C6-haloalkyl or C1-C6-haloalkoxy; R 4 yes or R 5 is C1-C3-alkylsulfonylamino, C1-C3-haloalkylsulfonylamino, or C3-C6-cycloalkylsulfonylamino, wherein any one of the amino groups is unsubstituted or replaced by R 6 substituted; and wherein any of the cycloalkyl groups may be R 9 Single or multiple substitution; R 6 is C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, cyano-C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkylcarbonyl or C1-C6-alkoxycarbonyl; R 8 is hydrogen, halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano; R 9 is halogen, C1-C3-alkyl, C1-C3-alkoxy, C1-C3-haloalkyl or cyano; and R 10 is halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6- Alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-haloalkylthio-C1-C6-alkyl, C1-C6-alkylsulfonyloxy, C1-C6-haloalkylsulfonyloxy, phenyl (which may be independently selected from halogen, C1-C6-alkyl and C1-C6-haloalkyl mono- or poly-substituted), phenyl-C1-C6-alkyl, phenyl-C1-C6-alkoxy, cyano and nitro; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer and N-oxide of the compound of formula (I).

2. The compound according to claim 1, wherein The compound having formula (I) is represented by formula (I-1), (I-2), (I-3) or (I-4), wherein A, R 1 , R 2 , R 3 and R 4 As defined in claim 1.

3. The compound according to claim 1, wherein The compound having formula (I) is represented by formula (I-1a), (I-2a), (I-3a) or (I-4a), wherein R 1 , R 2 , R 3 and R 6 As defined in claim 1; and wherein R 7 is independently selected from C1-C3-alkyl, C1-C3-haloalkyl or C3-C6-cycloalkyl, wherein the cycloalkyl may be R 9 Monosubstituted or polysubstituted, wherein R 9 As defined in claim 1.

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

5. The compound according to any one of claims 1 to 4, wherein R 1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkynyl, C3-C6-cycloalkyl, cyano-C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, heterocyclyl or C1-C6-alkoxy-C3-C6-cycloalkyl; and R 2 It is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-alkoxy-C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or C1-C6-alkylcarbonyl.

6. The compound according to any one of claims 1 to 5, wherein R 1 is C1-C3-alkyl, C1-C3-haloalkyl, C2-C4-alkynyl, C3-C4-cycloalkyl, C3-C4-halocycloalkyl, C3-C4-cycloalkyl-C1-C3-alkyl, a 4-membered heterocyclic group having SO2, or a cyano-C3-C4-cycloalkyl group; and R 2 is hydrogen, C1-C3-alkyl, C1-C3-alkylcarbonyl or C1-C3-alkoxycarbonyl.

7. The compound according to any one of claims 1 to 6, wherein R 3 is halogen, C1-C6-alkyl or cyano.

8. The compound according to claim 7, wherein R 3 It is chlorine, bromine or methyl.

9. The compound according to any one of claims 1 to 8, wherein R 5 It is isopropylsulfonylamino, difluoromethylsulfonylamino, trifluoromethylsulfonylamino, difluoromethylsulfonylamino or cyclopropylsulfonylamino.

10. The compound according to any one of claims 1 to 8, wherein R 6 It is hydrogen, C1-C3-alkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C4-cycloalkyl-C1-C3-alkyl or C1-C3-alkylcarbonyl.

11. A method for preparing a compound of formula (I) wherein A is O, comprising reacting a compound of formula (II) wherein R 3 , R 4 , X, Y, Z as defined in any one of claims 1 to 10 - a compound having formula (III) - wherein R 1 and R 2 As defined in any one of claims 1, 5 or 6 - converting:

12. A composition comprising a compound as defined in any one of claims 1 to 10, one or more adjuvants and diluents and optionally one or more other active ingredients.

13. A method for combating and controlling insects, acarines or molluscs, which comprises applying an insecticidal, acaricidal or molluscicidal effective amount of a compound of formula I as defined in any one of claims 1 to 10 or a composition as defined in claim 12 to the pest, the locus of the pest, or a plant susceptible to attack by the pest.

14. A method for protecting plant propagation material from insect, mite or mollusk attacks, comprising treating the propagation material or the site where the propagation material is planted with an effective amount of a compound of formula I as defined in any one of claims 1 to 10 or a composition as defined in claim 12.

15. A plant propagation material, such as a seed, comprising, treated with or having attached thereto, a compound of formula I as defined in any one of claims 1 to 10.

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