Microbial pyrazol inducer

Abstract

Compounds of formula (I) which can be used as fungicides [Formula 1] JPEG2025539250000070.jpg3447 (wherein the substituents are as defined in claim 1) and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds.

Description

[Technical Field]

[0001] The present invention relates to microbicidal pyrazole derivatives, for example as active ingredients, having microbicidal, particularly fungicidal, activity. The present invention also relates to the preparation of these pyrazole derivatives, intermediates useful for the preparation of these pyrazole derivatives, the preparation of these intermediates, pesticide compositions comprising at least one of these pyrazole derivatives, the preparation of these compositions, and the use of these pyrazole derivatives or compositions in agriculture or horticulture to control or prevent infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, particularly fungi. Summary of the Invention [Means for solving the problem]

[0002] According to a first aspect of the present invention, there is provided a compound of formula (I): [ka] (In the formula, B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 1 is selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C3-C6 cycloalkyl; R 2 is selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl, N-hydroxy-C—C1-C4 alkyl-carbonimidoyl or C1-C4 alkoxycarbonyl; R 3is selected from hydrogen, halogen, C1-C4 haloalkyl, or C1-C4 alkyl; R 4 is selected from hydrogen, halogen, C1-C4 haloalkyl, C3-C6 cycloalkyl, or C1-C4 alkyl; R 5 , R 6 , R 7 , R 8 and R 9 is hydrogen, halogen, hydroxy, amino, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, carbamoyl, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, C1-C4 alkylamino, C1-C4 dialkylamino, trifluoromethylsulfonyloxy independently selected from hydroxy, carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, or a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, and C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and Z 1is selected from C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or selected from halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl, N-hydroxy-C—C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- or 6-membered saturated, partially saturated or or substituted by 1, 2 or 3 substituents independently selected from an aromatic heterocycle or a C3-C6 cycloalkyl, wherein either the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains 1, 2 or 3 heteroatoms selected from O, S or N, provided that not more than one is O or S, and either the phenyl and the 5- or 6-membered saturated, partially saturated or aromatic heterocycle is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted by 1, 2 or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl or C1-C4 alkoxy). or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof.

[0003] Surprisingly, it has now been found that the compounds of formula (I) exhibit a level of biological activity which is highly advantageous in practice for protecting plants against diseases caused by fungi.

[0004] According to a second aspect of the present invention there is provided an agricultural composition comprising a fungicidally effective amount of a compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0005] According to a third aspect of the present invention, there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, wherein a fungicidally effective amount of a compound of formula (I) according to the present invention or a composition comprising a compound of formula (I) is applied to the plant, a part thereof or its habitat.

[0006] According to a fourth aspect of the present invention, there is provided the use of a compound of formula (I) according to the present invention as a fungicide. According to this particular aspect of the present invention, methods for treating the human or animal body by surgery or therapy and diagnostic methods carried out on the human or animal body may be excluded from this use. DETAILED DESCRIPTION OF THE INVENTION

[0007] The compounds of formula (I) having at least one basic centre 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, or with strong organic carboxylic acids, for example C1-C4 alkanecarboxylic acids which are unsubstituted or substituted, for example, by halogens, such as acetic acid, for example saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, for example hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid or for example benzoic acid, or with organic sulfonic acids, for example C1-C4 alkane or arylsulfonic acids which are unsubstituted or substituted, for example, by halogens, such as methane- or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, mineral salts such as alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0008] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example in agriculturally useful salt form.

[0009] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds, as described, for example, in A. Albini and S. Pietra, "Heterocyclic N-oxides," CRC Press, Boca Raton (1991).

[0010] The compounds of formula (I) according to the present invention also include hydrates which may be formed when salts are formed.

[0011] When substituents are indicated as "optionally substituted," this means that they may be substituted with one or more of the same or different substituents, for example, one, two, or three R x It means that it may or may not have a substituent. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens includes -CH2Cl, -CHCl2, -CCl 3、 Examples include, but are not limited to, -CHF, -CHF, -CF, -CHCF, or -CFCH groups. As another example, C1-C6 alkoxy substituted with 1, 2, or 3 halogens includes, but is not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O-, or CH3CF2O- groups.

[0012] As used herein, the term "optionally substituted" means that the referenced group is unsubstituted or unsubstituted with one or more identical or different substituents. The term "optionally substituted" can be used interchangeably with "can be unsubstituted or substituted." As used herein, the term "1 to 3 substituents" can be used interchangeably with "1 to 3 substituents" or "1, 2, or 3 substituents."

[0013] The term "halogen" or "halo" as used herein means fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine. Likewise, this applies to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy and halocycloalkyl.

[0014] As used herein, "amino" refers to the group --NH.sub.2.

[0015] As used herein, "cyano" refers to a -CN group.

[0016] The term "hydroxyl" or "hydroxy" as used herein means an --OH group.

[0017] As used herein, the term "carboxylic acid" refers to a -COOH group.

[0018] As used herein, "C1-C n The term "alkyl" refers to a saturated straight or branched hydrocarbon group having 1 to n carbon atoms and bonded via any carbon atom, such as any one of methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, or 1-ethyl-2-methylpropyl.

[0019] As used herein, "C2-C n The term "alkenyl" refers to a straight or branched alkenyl chain moiety having 2 to n carbon atoms and one or two double bonds, for example ethenyl, prop-1-enyl, but-2-enyl.

[0020] As used herein, "C2-C n The term "alkynyl" refers to a straight or branched alkynyl chain moiety having 2 to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl, but-3-ynyl.

[0021] As used herein, "C3-C nThe term "cycloalkyl" refers to 3 to n-membered cycloalkyl groups, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0022] As used herein, "C1-C n The term "alkoxy" refers to any one of a linear or branched saturated alkyl group (as described above) having 1 to n carbon atoms attached through an oxygen atom, i.e., a methoxy group, an ethoxy group, an n-propoxy group, a 1-methylethoxy group, an n-butoxy group, a 1-methylpropoxy group, a 2-methylpropoxy group, and a 1,1-dimethylethoxy group. n The term "alkenyloxy" refers to a straight or branched alkenyl chain (as described above) having 2 to n carbon atoms attached through an oxygen atom.

[0023] As used herein, "C1-C n Alkoxy-C1~C n The term "alkyl" refers to C1-C n It refers to an alkyl group (as defined above) substituted with an alkoxy group. Examples include methoxymethyl, methoxyethyl, ethoxymethyl, and propoxymethyl.

[0024] As used herein, "C3-C n Cycloalkyl-C1~C n The term "alkyl" refers to C3-C n It refers to an alkyl group (as described above) substituted with a cycloalkyl group. Examples are cyclopropylmethyl and cyclopropylethyl. Similarly, "C3-C n -Halocycloalkyl-C1-C n The term "alkyl" refers to an alkyl group substituted with a cycloalkyl group, where the cycloalkyl group is substituted with one or more of the same or different halogen atoms. Examples are 3,3-difluorobutylmethyl and 1-chlorocyclopropylmethyl.

[0025] As used herein, "C1-Cn The term "haloalkyl" refers to a linear or branched saturated alkyl group having 1 to n carbon atoms (as defined above) bonded via any of the carbon atoms, in which some or all of the hydrogen atoms of the group may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, It refers to any one of 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, and nonafluorobutyl. Thus, the term "C1-C2 fluoroalkyl" refers to any one of C1-C2 alkyl groups having 1, 2, 3, 4 or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl or pentafluoroethyl. Similarly, as used herein, "C2-C n -haloalkenyl" or "C2-C n The term "haloalkynyl" refers to a C-C alkyl group substituted with one or more halogen atoms, each of which may be the same or different. n Alkenyl or C2-C nSimilarly, as used herein, "C3-C" refers to an alkynyl group. n -halocycloalkyl" or "C1-C n The term "haloalkoxy" refers to a C-C alkyl group substituted with one or more halogen atoms, each of which may be the same or different. n Cycloalkyl group or C1-C n Refers to an alkoxyl group.

[0026] As used herein, "C1-C n Alkylthio" or "C1-C n "Alkylsulfanyl" refers to C1-C alkylsulfanyl groups bonded via a sulfur atom. n Refers to an alkyl group.

[0027] As used herein, "C1-C n -haloalkylthio" or "C1-C n The term "haloalkylsulfanyl" refers to a C1-C alkyl group bonded through a sulfur atom. n Refers to haloalkyl groups.

[0028] As used herein, "C1-C n The term "alkylsulfinyl" refers to a C1-C alkyl group bonded through the sulfur atom of the sulfinyl (or S(=O)-) group. n Refers to an alkyl group.

[0029] As used herein, "C1-C n The term "alkylsulfonyl" refers to a C1-C alkyl group bonded through the sulfur atom of the sulfonyl (or S(=O)2-) group. n Refers to an alkyl group.

[0030] As used herein, "C1-C n Alkylsulfonyl-C1~C n The term "alkyl" refers to C1-C n C1-C substituted with alkylsulfonyl groups n Refers to an alkyl group.

[0031] As used herein, "C1-C nThe term "alkylcarbonyl" refers to a C1-C alkyl group bonded through the carbon atom of a carbonyl (C=O) group. n Refers to an alkyl group.

[0032] As used herein, "C1-C n The term "alkoxycarbonyl" refers to a C1-C alkyl group bonded through the carbon atom of a carbonyl (or C=O) group. n Refers to the alkoxy moiety.

[0033] As used herein, "C1-C n Alkoxycarbonyl-C1~C n The term "alkyl" refers to C1-C n C1-C substituted with alkoxycarbonyl group n Refers to an alkyl group.

[0034] The term "benzoyl," as used herein, refers to a phenyl group attached through the carbon atom of a carbonyl (C=O) group.

[0035] As used herein, "C1-C n The term "alkylaminocarbonyl" refers to a group of the formula R bonded through the carbon atom of a carbonyl (C=O) group. a NHC(=O)-(wherein, R a are the general definitions of C1 to C n It refers to the group (which is an alkyl group).

[0036] As used herein, "di(C1-C n The term "aminocarbonyl" refers to a group of the formula R bonded through the carbon atom of a carbonyl (C=O) group. a NR b C(=O)(in the formula, R a are the C1 to C2 defined generally above. n is an alkyl group, and R b are the general definitions of C1 to C n It refers to the group (which is an alkyl group).

[0037] As used herein, the term “N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NO(R b )(wherein, R a is a C1-C4 alkyl group as generally defined above, and R b refers to a group of which the alkyl group is a C1-C4 alkyl group as generally defined above.

[0038] As used herein, the term “N-hydroxy-C—Ci-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NOH(where R a is a C1-C4 alkyl group as generally defined above).

[0039] As used herein, "cyano-C1-C n The term "alkyl" refers to a C1-C6 alkyl group having 1 to n carbon atoms in which one of the hydrogen atoms of the group is replaced by a cyano group. n Alkyl group (as defined above): for example, cyanomethyl, 2-cyanoethyl, 2-cyanopropyl, 3-cyanopropyl, 1-(cyanomethyl)-2-ethyl, 1-(methyl)-2-cyanoethyl, 4-cyanobutyl, etc. Similarly, "cyano-C3-C n The term "cycloalkyl" refers to a C3-C6 alkyl group in which one of the hydrogen atoms is replaced by a cyano group. n It refers to a cycloalkyl group, and is referred to as "cyano-C3-C n Cycloalkyl-C1~C n The term "alkyl" refers to cyano-C3-C n C1-C with cycloalkyl groups n Refers to an alkyl group.

[0040] The term "heteroaryl," as used herein, refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, 3, or 4 heteroatoms independently selected from N, O, and S. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl. "Heteroaryl-C1-C n "Alkyl" or "Heteroaryl-C3-C n The term "cycloalkyl" refers to a C1-C6 alkyl group substituted with a heteroaryl group. n Alkyl or C3-C n This refers to a cycloalkyl group. n Alkyl or heteroaryl-C3-C n The heteroaryl, alkyl and / or cycloalkyl groups of the cycloalkyl group can be optionally substituted.

[0041] As used herein, the terms "4-, 5-, or 6-membered saturated, partially unsaturated, or aromatic heterocycle" "containing 1, 2, or 3 heteroatoms" or "containing heteroatomic groups" refer to those heteroatoms (groups) that are selected from the group consisting of N, O, S, NO, SO, and SO. 2 or a ring member selected from N, O and S refers to a monocyclic group, which is saturated, partially unsaturated or aromatic. The heterocyclic group can be attached to the remainder of the molecule through a carbon ring member or through a nitrogen ring member.

[0042] The term "4-, 5-, or 6-membered saturated, partially unsaturated, or aromatic heterocycle" can be used interchangeably with "4-, 5-, or 6-membered saturated, partially unsaturated, or aromatic heteroaryl" throughout this specification.

[0043] Examples of 4, 5, or 6-membered saturated heterocyclic rings or heterocycles include, but are not limited to, 2 tetrahydrofuranyl, 3-tetrahydrofuranyl, 2 tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3 pyrazolidinyl, 4 pyrazolidinyl, 5-pyrazolidinyl, 2 imidazolidinyl, 4 imidazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5 oxazolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5 isoxazolidinyl, 2 thiazolidinyl, 4 -thiazolidinyl, 5-thiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4 triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4 thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, 2-morpholinyl, 3-morpholinyl, 2-thiomorpholinyl, 3-thiomorpholinyl, 1-oxo Examples include isothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, hexahydrooxepinyl, hexahydro-1,3-diazepinyl, hexahydro-1,4-diazepinyl, hexahydro-1,3-oxazepinyl, hexahydro-1,4-oxazepinyl, hexahydro-1,3-dioxepinyl, and hexahydro-1,4-dioxepinyl.

[0044] Examples of 4-, 5- or 6-membered partially unsaturated heterocyclic rings or heterocycles include 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 3-isoxazolin-4-yl, 3-isoxazolin-5-yl, 3-isoxazolin-6-yl, 3-isoxazolin-7-yl, 3-isoxazolin-8-yl, 3-isoxazolin-9-yl, 3-isoxazolin-10-yl, 3-isoxazolin-11-yl, 3-isoxazolin-12-yl, 3-isoxazolin-13-yl, 3-isoxazolin-14-yl, 3-isoxazolin-15-yl, 3-isoxazolin-16-yl, 3-isoxazolin-17-yl, 3-isoxazolin-18-yl, 3-isoxazolin-19-yl, 3-isoxazolin-20-yl, 3-isoxazolin-21-yl, 3-isoxazolin-22-yl, 3-isoxazolin-23-yl, 3-isoxazolin-24-yl, 3-isoxazolin-25-yl, 3-isoxazolin-19-yl, 3-isoxazolin-2 isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-Isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol pyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotri azin-2-yl, 1,2,4-di- or tetrahydrotriazin-3-yl, 2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydrooxepinyl, for example 2,3,4,5-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl or -7-yl, 2,3,6,7 tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, tetrahydro-1,3-diazepinyl, tetrahydro-1,4-diazepinyl, tetrahydro-1,3-oxazepinyl, tetrahydro-1,4-oxazepinyl, tetrahydro-1,3-dioxepinyl and tetrahydro-1,4-dioxepinyl.

[0045] Examples of 5- or 6-membered aromatic heterocyclic rings or heterocycles, also referred to as heteroaromatic rings or heteroaryls, include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

[0046] The terms "heterocyclyl," "heterocycle," or "heterocyclic," as used herein, refer to a stable 4-, 5-, or 6-membered non-aromatic monocyclic ring group containing one, two, or three heteroatoms independently selected from nitrogen, oxygen, and sulfur, provided that only one is O or S. A heterocyclic group can be attached to the remainder of the molecule through a carbon atom or a heteroatom. Examples of heterocyclic groups include, but are not limited to, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dioxolanyl, morpholinyl, oxazinanyl, oxetanyl, or δ-lactamyl.

[0047] As used herein, the term "controlling" refers to reducing the number of pests, eliminating pests, and / or preventing further pest damage so that damage to plants or plant-derived products is reduced.

[0048] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, storing plant-derived products (such as fruit, grain, and timber), and pests associated with damaging man-made structures. The term pest includes all stages of the pest life cycle.

[0049] As used herein, the term "effective amount" refers to an amount of a compound or a salt thereof that produces a desired effect upon single or multiple applications.

[0050] Effective amounts are readily determined by those skilled in the art using known techniques and by observing results obtained under similar circumstances. Many factors are taken into consideration in determining an effective amount, including, but not limited to, the type of plant or plant-derived product to be applied, the pest to be controlled and its life cycle, the particular compound to be applied, the type of application, and other relevant circumstances.

[0051] As used herein, the terms "room temperature" or "RT" or "rt" refer to a temperature of about 15°C to about 35°C. For example, rt can refer to a temperature of about 20°C to about 30°C.

[0052] The following list describes the substituents R for compounds of formula (I) of the present invention: 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , B 3 and Z 1 Any of the definitions given below for any one of these substituents can be combined with any definition of any other substituent given below or elsewhere in this specification.

[0053] In one embodiment, R 1 is selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or C3-C6 cycloalkyl. Preferably, R 1 is C1-C4 alkyl. More preferably, R 1 is methyl, ethyl or isopropyl. More preferably, R 1 is methyl.

[0054] In one embodiment, R 2 is selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl, N-hydroxy-C—C1-C4 alkyl-carbonimidoyl, or C1-C4 alkoxycarbonyl. Preferably, R 2 is hydrogen, halogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl or N-hydroxy-C-C1-C4 alkyl-carbonimidoyl. More preferably, R 2 is hydrogen, halogen, methyl, ethyl, cyclopropyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl or N-hydroxy-C-C1-C2 alkyl-carbonimidoyl. 2 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, cyclopropyl, acetyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3 or -C(CH3)=NOH. More preferably, R 2 is hydrogen, fluorine, chlorine or methyl. Most preferably, R 2 is hydrogen, chlorine or methyl.

[0055] In one embodiment, R 3 is selected from hydrogen, halogen, C1-C4 haloalkyl or C1-C4 alkyl. Preferably, R 3 is hydrogen or C1-C4 alkyl. More preferably, R 3 is hydrogen or methyl. Most preferably, R 3 is hydrogen.

[0056] In one embodiment, R 4 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C6 cycloalkyl. Preferably, R 4is hydrogen, chlorine, bromine, fluorine, methyl, ethyl, trifluoromethyl, difluoromethyl or cyclopropyl. More preferably, R 4 is hydrogen, chlorine, bromine or methyl. Most preferably, R 4 is hydrogen.

[0057] In one embodiment, R 5 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, carbamoyl, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, amino, C1-C4 alkylamino, C1-C4 dialkylamino, trifluoromethylsulfonyloxy, The 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle is selected from cyano, carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, and a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano. More preferably, R 5is hydrogen, fluorine, chlorine, bromine, methyl or cyano. More preferably, R 5 is hydrogen, fluorine, methyl or cyano. More preferably, R 5 is hydrogen or cyano. Most preferably, R 5 is hydrogen.

[0058] In one embodiment, R 6 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, carbamoyl, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, amino, C1-C4 alkylamino, C1-C4 dialkylamino, trifluoromethylsulfonyloxy The 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle is selected from hydroxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, or a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 6is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, hydroxy, cyano, or C3-C6 cycloalkyl, wherein the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. More preferably, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl or methylcyclopropyl. 6 is hydrogen, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano or cyclopropyl. 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl. Even more preferably, R 6 is hydrogen, cyano or cyclopropyl. Even more preferably, R 6 is hydrogen or cyano. Most preferably, R 6 is hydrogen.

[0059] In one embodiment, B 1 is CR 7 or N. In another embodiment, B 1 is CR 7 In another embodiment, B 1 is N.

[0060] In one embodiment, R 7is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, amino, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, trifluoromethylsulfonyloxy, cyano , carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, or a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycles contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycles is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 7 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, hydroxy, cyano, or C3-C6 cycloalkyl, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. More preferably, R 7is hydrogen, halogen, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, or C3-C6 cycloalkyl, and the C3-C6 cycloalkyl is unsubstituted or substituted with one substituent selected from halogen, cyano, or C1-C4 alkyl. More preferably, R 7 is hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl or methylcyclopropyl. 7 is hydrogen, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano or cyclopropyl. 7 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl. Even more preferably, R 7 is hydrogen, cyano or cyclopropyl. Most preferably, R 7 is hydrogen or cyano.

[0061] In one embodiment, B 2 is CR 8 or N. In another embodiment, B 2 is CR 8 In another embodiment, B 2 is N.

[0062] In one embodiment, R 8is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, amino, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, trifluoromethylsulfonyloxy, cyano , carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, or a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycles contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycles is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 8is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, amino, C1-C4 alkylamino, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, C1-C4 dialkylamino, hydroxy, cyano, or C3-C6 cycloalkyl, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. More preferably, R 8 is hydrogen, halogen, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, or C3-C6 cycloalkyl, and the C3-C6 cycloalkyl is unsubstituted or substituted with one substituent selected from halogen, cyano, or C1-C4 alkyl. More preferably, R 8 is hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl or methylcyclopropyl. 8 is hydrogen, chlorine, bromine, fluorine, methyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano or cyclopropyl. 8 is hydrogen, chlorine, bromine, fluorine, difluoromethyl, methyl, cyano or cyclopropyl. Even more preferably, R 8is hydrogen, cyano, difluoromethyl or cyclopropyl. Even more preferably, R 8 is hydrogen. Most preferably, R 8 is hydrogen or cyano. Even more preferably, R 8 is hydrogen.

[0063] In one embodiment, B 3 is CR 9 or N. In another embodiment, B 3 is CR 9 In another embodiment, B 3 is N.

[0064] In one embodiment, R 9is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, amino, C1-C4 alkylamino, C1-C4 dialkylamino, C1-C4 alkylaminocarbonyl, di(C1-C4)alkylaminocarbonyl, cyano-C1-C4 alkyl, trifluoromethylsulfonyloxy, cyano , carboxy, phenyl, a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, or a C3-C6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycles contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycles is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C6 cycloalkyl. More preferably, R 9 is hydrogen, halogen, methyl, cyano, difluoromethyl or cyclopropyl. More preferably, R 9 is hydrogen, chlorine, bromine, methyl, cyano, difluoromethyl or cyclopropyl. Most preferably, R 9 is hydrogen or cyano. Even more preferably, R 9 is hydrogen.

[0065] In one embodiment, Z 1 is selected from C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or selected from halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- or 6-membered saturated, partially saturated or or an aromatic heterocycle or a C3-C6 cycloalkyl, wherein either the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycle contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy; and the C3-C6 cycloalkyl is unsubstituted or substituted with 1, 2, or 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, Z 1is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocycle, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains one, two or three heteroatoms selected from O, S or N, and one or less are O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy. Preferably, Z 1 is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl, and a 5- to 6-membered saturated, partially saturated, or aromatic heterocycle, wherein either the phenyl or the 5- to 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one substituent selected from halogen, cyano, or C1-C4 alkyl.

[0066] Therefore, according to the present invention, R as defined above 1 , R 2 , R 3 , R 4 , R 5 , R 6, R 7 , R 8 , R 9 , B 1 , B 2 , B 3 and Z 1 Compounds of formula (I) having any combination / configuration of the above are available.

[0067] Embodiments according to the present invention are provided as follows.

[0068] In one embodiment of the present invention, the compound of formula (I) is R 1 is methyl and R 3 is hydrogen, formula (IA): [ka] wherein R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , B 3 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0069] Preferably, in the compound of formula (IA) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , B 3 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0070] Preferably, in the compound of formula (IA) of the present invention, R 2is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 7 , R 8 , R 9 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0071] Preferably, in the compound of formula (IA) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 7 , R 8 , R 9 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0072] Preferably, in the compound of formula (IA) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0073] Preferably, in the compound of formula (IA) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR9 or N, R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0074] Preferably, in the compound of formula (IA) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1 is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocycle, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocycle contains one, two or three heteroatoms selected from O, S or N, and one or less are O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy.

[0075] In one embodiment of the present invention, the compound of formula (I) is R 1 is methyl and R 3 is hydrogen, and B 1 is CR 7 and B 2 is CR 8 and B 3 is N, Formula (I-A1): [ka] wherein R 2 , R 4 , R 5 , R 6 , R 7 , R 8 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0076] Preferably, in the compound of formula (I-A1) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 , R 6 , R 7 , R 8 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0077] Preferably, in the compound of formula (I-A1) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0078] Preferably, in the compound of formula (I-A1) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; R7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0079] Preferably, in the compound of formula (I-A1) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; Z 1is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocyclic rings contains one, two or three heteroatoms selected from O, S or N; provided that one or less is O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy.

[0080] In one embodiment of the present invention, the compound of formula (I) is R 1 is methyl and R 3 is hydrogen, and B 1 is CR 7 and B 2 is CR 8 and B 3 is CR 9 Formula (I-A2): [ka] wherein R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0081] Preferably, in the compound of formula (I-A2) of the present invention, R2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 , R 6 , R 7 , R 8 , R 9 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0082] Preferably, in the compound of formula (I-A2) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0083] Preferably, in the compound of formula (I-A2) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6are independently selected from hydrogen or cyano; R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0084] Preferably, in the compound of formula (I-A2) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl; R 9 is hydrogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl or C3-C6 cycloalkyl; Z 1is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocyclic rings contains one, two or three heteroatoms selected from O, S or N; provided that one or less is O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy.

[0085] In one embodiment of the present invention, the compound of formula (I) is R 1 is methyl and R 3 is hydrogen, and B 1 , B 2 and B 3 is N, Formula (I-A3): [ka] wherein R 2 , R 4 , R 5 , R 6 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0086] Preferably, in the compound of formula (I-A3) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 , R6 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0087] Preferably, in the compound of formula (I-A3) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; Z 1 is as defined for the compounds of formula (I) according to the invention.

[0088] Preferably, in the compound of formula (I-A3) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, Z 1 is as defined for the compounds of formula (I) according to the invention.

[0089] Preferably, in the compound of formula (I-A3) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 is hydrogen, halogen, C1-C4 alkyl or cyano, R 6 is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl, Z 1is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocyclic rings contains one, two or three heteroatoms selected from O, S or N; provided that one or less is O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy.

[0090] Preferably, in the compound of formula (I-A3) of the present invention, R 2 is hydrogen, chlorine or methyl, R 4 is hydrogen, R 5 and R 6 are independently selected from hydrogen or cyano; Z 1is a C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with one, two or three substituents independently selected from the group consisting of halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 haloalkoxy, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, phenyl or a 5- or 6-membered saturated, partially saturated or aromatic heterocyclic ring, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocyclic rings contains one, two or three heteroatoms selected from O, S or N; provided that one or less is O or S, and either the phenyl or the 5- or 6-membered saturated, partially saturated, or aromatic heterocycle is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy, and the C3-C6 cycloalkyl is unsubstituted or substituted with one or two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl, or C1-C4 alkoxy.

[0091] In any of the compounds selected from compounds of formula (I), (IA), (I-A1), (I-A2) and (I-A3) or compounds selected from compounds set forth in Tables A-1 to A-23 or Table P (described below), the possible presence of one or more asymmetric carbon atoms means that chiral isomeric forms, i.e., enantiomeric or diastereomeric forms, of the compound may exist.

[0092] More preferably, the compound of formula (I) according to the present invention is selected from the compounds set forth in any one of Tables A-1 to A-23.

[0093] More preferably, the compounds of formula (I) according to the present invention are selected from the compounds set out in Table P (below).

[0094] Compounds of formula (I) according to the present invention can be prepared as shown in Schemes 1-10 below, where, unless otherwise specified, the definition of each variable is as defined above for compounds of formula (I).

[0095] In particular, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , B 3 and Z 1 Compounds of formula (I), wherein is as described for formula (I), can be prepared as described in Schemes 1-10 below, where, unless otherwise specified, the definition of each variable is as defined above for compounds of formula (I).

[0096] In any of the following schemes 1 to 10, the possible presence of one or more asymmetric carbon atoms in the compound of formula (I) according to the present invention means that the compound may exist in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0097] The compound of formula (I) can be prepared by methods known to those skilled in the art. More specifically, the compound of formula (I) can be prepared by methods known to those skilled in the art. 1 is as defined above for compounds of formula (I)) or a salt thereof to prepare a compound of formula (II) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 and B 3 can be prepared by reacting a compound of Formula (I) (as defined above for compounds of Formula (I)). This reaction is shown in Scheme 1. [ka] Scheme 1

[0098] In Scheme 1, a compound of formula (II) (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 and B 3 Compounds of formula (IIa) (wherein X is as defined above for compounds of formula (I)) can be activated to compounds of formula (IIa) by methods known to those skilled in the art, for example as described in Tetrahedron 2005, 61(46), 10827-10852. For example, compounds of formula (IIa) (wherein X 0 Compounds of formula (IIa) are formed by treating compounds of formula (II) with, for example, oxalyl chloride or thionyl chloride in an inert solvent such as methylene chloride or tetrahydrofuran (THF) in the presence of a catalytic amount of N,N-dimethylformamide (DMF) at temperatures between 20°C and 100°C, preferably 25°C. Compounds of formula (IIa) are formed by treating compounds of formula (III) (wherein Z is a halogen) with, for example, oxalyl chloride or thionyl chloride in the presence of a catalytic amount of N,N-dimethylformamide (DMF) at temperatures between 20°C and 100°C, preferably 25°C. 1 is as defined above for compounds of formula (I), optionally in the presence of a base such as triethylamine or pyridine, to give compounds of formula (I). Alternatively, compounds of formula (I) can be converted to activated compounds of formula (IIb) (wherein G is as defined above for compounds of formula (I)) by treating compounds of formula (II) with dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) in an inert solvent such as pyridine, DMF, acetonitrile, CHCl or THF, optionally in the presence of a base such as triethylamine, at a temperature between 30° C. and 180° C. 0 is shown below. 01 , G 02 or G 03Finally, compounds of formula (II) can be prepared by reacting with a coupling reagent such as propanephosphonic anhydride (T3P), as described, for example, in Synthesis 2013, 45, 1569, to give compounds of formula (IIa) (wherein G 0 is shown below. 04 Further, by reacting with an amine (or a salt thereof) compound of formula (III), a compound of formula (I) is obtained. [ka]

[0099] Furthermore, the compound of formula (II) can be represented by the formula (IIc) (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 , B 2 and B 3 is as described for formula (I), and R 01 is a C1-C4 alkyl) by hydrolysis of an ester. Various conditions can be used, such as aqueous sodium hydroxide or lithium hydroxide and a water-miscible organic solvent such as THF, dimethoxyethane, methanol, or ethanol. Such ester hydrolysis is well known to those skilled in the art. Alternatively, a compound of formula (IIc) can be directly converted to a compound of formula (I) by reacting the compound of formula (IIc) with a compound of formula (III) in the presence of trimethylaluminum (AlMe3) or trimethylaluminum-DABCO complex (AlMe3-DABCO) in an inert solvent such as toluene or methylene chloride. Such reactions have been reported in the literature (see Tetrahedron Lett. 1977, 4171-4174, Tetrahedron Lett. 2006, 5767-5769 and references cited therein). A further method for preparing a compound of formula (I) involves the reaction of a compound of formula (III) with a compound of formula (IV) (wherein R1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 , B 2 and B 3 is as defined for compounds of formula (I), and X 02 is a halogen, preferably Cl, Br, or I. Such aminocarbonylation involves treating a compound of formula (III) with a compound of formula (IV) in the presence of a palladium catalyst, such as [1,3-bis(diphenylphosphino)propane]palladium(II) chloride, in an inert solvent such as methyl-THF or THF and a base such as triethylamine, under a carbon monoxide atmosphere of 1 to 10 bar. Such aminocarbonylation reactions are well known to those skilled in the art, and similar reactions have been reported, for example, in Org. Lett. 2007, 9, 4575-4578 or Org. Lett. 2015, 17, 3236-3239.

[0100] Compounds of formula (II) and (IIc) are commercially available or can be synthesized as described below.

[0101] Formula (IIa) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), and B 3 is N and X 0 is C1-C4 alkyl), i.e., the compound of formula (IIaa) can be obtained by the compound of formula (IVa) (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2is as defined above for compounds of formula (I) and B3 is N), i.e., compounds of formula (IVaa) can be prepared by reacting a compound of formula (IVaa) with an alcohol X in a high pressure reactor, typically in 1-10 bar of carbon monoxide, using palladium catalyzed conditions similar to those described in US Patent Publication No. 20150218102 or WO 98 / 04557. 0 -OH(wherein, X 0 is C1~C 4 alkyl) and a base, such as triethylamine, whereby X 0 The corresponding esters, in which is C1-C4 alkyl, are obtained (Scheme 2). [ka] Scheme 2

[0102] Formula (IVaa) (where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), and B 3 is nitrogen) can be prepared by the compound of formula (V) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), and B 3 is N + -O - (N-oxide)) with a chlorinating agent such as phosphorus oxychloride, oxalyl chloride, or thionyl chloride, either directly or in the presence of an inert solvent. A similar reaction is described, for example, in Tetrahedron Lett. 2014, 55(51), 7130-7132 (Scheme 3). [ka] Scheme 3

[0103] Formula (V) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), the compound of formula (VI) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 can be prepared by reacting a compound of formula (I) (as defined above for the compound of formula (I)) with an oxidizing agent such as hydrogen peroxide or m-chloroperbenzoic acid in acetic acid in the presence of a solvent. Similar reactions are described in WO 04 / 052370 or Adv. Synth. Cat. 2020, 362(24), 5777-5782. Such oxidations can also be carried out using ruthenium as a catalyst in the presence of oxygen, as described in Chem. Comm. 2002, 10, 1040-1041 (Scheme 4). [ka] Scheme 4

[0104] Formula (VI) (wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), the compound of formula (VIII) 1 , R 2 and R 3 is as defined above for compounds of formula (I), and X 0is a halogen, preferably chlorine, bromine or iodine, by reacting a compound of formula (VII) 4 , R 5 , R 6 , B 1 and B 2 can be prepared by reacting a compound of Formula (I) with a compound of Formula (I) (as defined above for compounds of Formula (I)) using a C—C bond forming reaction, typically under palladium-catalyzed (alternatively nickel-catalyzed) cross-coupling conditions (Scheme 5). [ka] Scheme 5

[0105] The Suzuki-Miyaura cross-coupling reaction of a compound of formula (VII) with a compound of formula (VIII) is known to those skilled in the art and is typically carried out in the presence of a palladium catalyst such as tetrakis(triphenylphosphine)-palladium(0) or [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex and a base such as sodium carbonate or potassium carbonate in a solvent such as N,N-dimethylformamide, dioxane, or a dioxane-water mixture at a temperature between room temperature and 160°C, optionally under microwave heating conditions, preferably under an inert atmosphere. Such reactions are reviewed, for example, in J. Organomet. Chem. 1999, 576, 147-168. Those skilled in the art will recognize that this reaction can be carried out by reacting a compound of formula (X) (wherein R 1 , R 2 and R 3 is as defined above for compounds of formula (I)) with a compound of formula (IX) 4 , R 5 , R 6 , R 7 , B 1 and B 2 is as defined above for compounds of formula (I), and X 0 is a halogen, preferably chlorine, bromine or iodine, to form a compound of formula (VI) 1 , R 2 , R 3 , R4 , R 5 , R 6 , B 1 and B 2 It will be appreciated that the above reaction can also be carried out by obtaining a compound of formula (I) (as defined above for compounds of formula (I)) (Scheme 6). [ka] Scheme 6

[0106] Further cross-coupling chemistry, i.e., C—H activation, can be used to obtain compounds of formula (VI), where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I)) can also be prepared (Scheme 7). [ka] Scheme 7

[0107] As shown in Scheme 7, a compound of formula (XI) (wherein R 4 , R 5 , R 6 , B 1 and B 2 is as defined above for compounds of formula (I), and X 0 is a halogen, preferably chlorine, bromine or iodine, by reacting a compound of formula (XII) 1 , R 2 and R 3is as defined above for compounds of formula (I)) in the presence of a palladium catalyst, typically palladium acetate Pd(OAc)2, a suitable ligand, for example 1,10-phenanthroline, and a base such as cesium carbonate or potassium carbonate, in an inert solvent such as chlorobenzene, toluene or xylene, at temperatures between rt and 180°C, optionally under microwave heating conditions, preferably under an inert atmosphere. Similar reactions have been reported in the literature, for example in Chem. Sci. 2013, 4, 2374-2379.

[0108] Formula (I) (wherein, R 1 , R 2 , R 3 , R 5 , R 6 , B 1 , B 2 and Z 1 is as described for formula (I), and B 3 is nitrogen and R 4 is hydrogen), i.e., compounds of formula (IA), are shown in Scheme 8. [ka] Scheme 8

[0109] As shown in Scheme 9, a compound of formula (XIII) (wherein R 1 , R 2 and R 3 is as defined above for formula (I)) with a compound of formula (XIV) 5 , R 6 , B 1 and B 2 is as defined above) and a compound of formula (XV) 01 is C1-C4 alkyl) in an inert solvent such as methanol under silver / trifluoromethanesulfonic acid catalyzed reaction conditions to give a compound of formula (IId) (wherein R 1 , R 2 , R 3 R 5 , R 6 , B 1, B 2 and R 01 is as defined above), a compound of formula (IId) is obtained. Compounds of formula (IId) are converted to compounds of formula (IA) using the method described in Scheme 1. Such reactions are described, for example, in Tetrahedron Lett. 2019, 60(14), 965-970. A very similar type of reaction can also be used to produce compounds of formula (IId), as shown in Scheme 9. [ka] Scheme 9

[0110] In this case, an acetyl compound of formula (XVI) is used, and the catalytic system is Cu(II) trifluoromethanesulfonate / trifluoromethanesulfonic acid in acetonitrile under air (see Org. Chem. Front. 2018, 5, 1713-1718). Compounds of formula (XIII) and (XVI) can be prepared by the reaction of a compound of formula (XVII) (wherein R 1 , R 2 and R 3 can be easily prepared from a compound of formula (wherein X is as defined above and X is a halogen, preferably chlorine, bromine or iodine) by palladium-catalyzed Sonogashira coupling and Stille coupling, respectively, which are well known to those skilled in the art (Scheme 10). [ka] Scheme 10

[0111] All other compounds depicted in Schemes 1-10, other than those specifically described, can be prepared according to methods known to those skilled in the art or are commercially available.

[0112] Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0113] Salts of compounds of formula (I) can be converted into the free compounds (I) in a conventional manner, for example into acid addition salts by treatment with a suitable basic compound or a suitable ion exchange reagent, and converted into salts with bases, for example by treatment with a suitable acid or a suitable ion exchange reagent.

[0114] Salts of compounds of formula (I) can be converted into other salts of compounds of formula (I) in a manner known per se, for example by converting an acid addition salt into another acid addition salt, for example by treating a salt of an inorganic acid, such as the hydrochloride, with a suitable metal salt, such as the sodium, barium or silver salt of the acid, for example silver acetate, in a suitable solvent in which the inorganic salt formed, for example silver chloride, is insoluble and is therefore precipitated from the reaction mixture.

[0115] Depending on the procedure or reaction conditions, compounds of formula (I) that have salt-forming properties may be obtained in the free form or in the form of a salt.

[0116] The compounds of formula (I) and, where appropriate, their tautomers, in each case in free or salt form, can, depending on the number, the absolute and relative configuration of asymmetric carbon atoms present in the molecule and / or depending on the configuration of non-aromatic double bonds present in the molecule, exist in the form of one of the possible isomers or as a mixture thereof, in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, for example racemates or diastereomeric mixtures; the invention relates to all possible isomeric mixtures as well as to pure isomers, and in each case as mentioned above and hereinafter, even if specific stereochemical details are not stated, to be understood in this sense in each case.

[0117] Diastereomeric or racemic mixtures of compounds of formula (I) in free or salt form, which may be obtained depending on the starting materials and procedures selected, can be separated into pure diastereomers or racemates on the basis of the physicochemical differences of the components in known manner, for example by fractional crystallization, distillation and / or chromatography.

[0118] Enantiomeric mixtures, such as racemates, obtainable in a similar manner can be resolved into their optical antipodes by known methods, such as recrystallization from optically active solvents, chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetylcellulose, by the use of suitable microorganisms, cleavage with specific immobilized enzymes, through the formation of inclusion compounds, for example using chiral crown ethers which complex with only one enantiomer, or conversion of diastereomeric salts, for example by reacting the basic final product racemate with an optically active acid, such as a carboxylic acid, for example camphoric acid, tartaric acid or malic acid, or a sulfonic acid, for example camphorsulfonic acid, and separating the diastereomeric mixture thus obtainable, for example by fractional crystallization based on their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example a basic agent.

[0119] Pure diastereomers or enantiomers can be obtained according to the invention not only by separation of the appropriate isomeric mixture, but also by generally known diastereoselective or enantioselective synthetic methods, e.g., by carrying out the process according to the invention using starting materials with the appropriate stereochemistry.

[0120] If the biological activity of the individual components differs, it may be advantageous to isolate or synthesize isomers, such as enantiomers or diastereomers, or isomeric mixtures, such as enantiomeric or diastereomeric mixtures, which are in each case more biologically effective.

[0121] For example, compounds with two or more asymmetric carbon atoms may exist in diastereomeric forms, which can optionally be optically separated on chiral columns, for example using supercritical fluid chromatography (SFC) chromatography. Although such diastereomers may exhibit different fungicidal activity profiles, all isomers and diastereomers form part of the present invention.

[0122] As already indicated, it has surprisingly been found that the compounds of formula (I) of the present invention exhibit a level of biological activity which is highly advantageous in practice for protecting plants against diseases caused by fungi.

[0123] The compounds of the present invention selected from the compounds of formula (I), (IA), (I-A1), (I-A2), or (I-A3), or one of the compounds listed in Tables A-1 to A-23 or Table P (described below), can be used as active ingredients in agriculture and related fields of use, for example, to control plant pests or to control spoilage microorganisms on non-living materials or organisms potentially harmful to humans. These novel compounds are distinguished by excellent activity at low application rates, good plant tolerance, and environmental safety. They possess highly useful curative, preventive, and systemic properties, allowing them to be used in the protection of many cultivated plants. The compounds of formula (I) can be used to suppress or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various crops of useful plants, while simultaneously protecting later-growing parts of these plants, for example, from phytopathogenic microorganisms.

[0124] The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and / or harvested food crops that are susceptible to attack by microorganisms by treating the plants or plant propagation material and / or harvested food crops, in which an effective amount of a compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2) or (I-A3) according to the present invention or one compound selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds listed in Table P (described below) is applied to the plant, a part thereof or its habitat.

[0125] A compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2) or (I-A3) according to the present invention or one selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds described in Table P (described below) can also be used as a fungicide. As used herein, the term "fungicide" means a compound that controls, modifies or prevents the growth of fungi. When the term "fungicidally effective amount" is used, it means an amount of such a compound or combination of such compounds that is capable of affecting the growth of fungi. A controlling or modifying effect includes any deviation from natural development, such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in or on the plant that prevents fungal infection.

[0126] A compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2), or (I-A3) according to the present invention, or one selected from the group consisting of the compounds shown in Tables A-1 to A-23 or Table P (described below), may also be used as a dressing agent to treat plant propagation material, such as seeds of fruits, tubers, or grains, or plant cuttings, to protect them from fungal infection and protect them from phytopathogenic fungi present in the soil. The propagation material can be treated with a composition containing a compound of formula (I) before planting; for example, seeds can be dressed before sowing. The active compound of formula (I) can also be applied to grains (coatings) by either impregnating the seeds with a liquid formulation or coating them with a solid formulation. The composition can also be applied to the planting locus before planting the propagation material, for example, by applying it to the sowing furrow at the time of sowing. The present invention also relates to a method for treating such plant propagation material and to the plant propagation material treated in this way.

[0127] Furthermore, the compounds of formula (I) according to the invention can be used to control fungi in related fields, such as the protection of technical products, including wood and wood-related technical products, food storage, hygiene.

[0128] Additionally, the present invention may be used to protect non-living materials such as timber, wall materials and paints from fungal attack.

[0129] A compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2) or (I-A3) according to the present invention, or one compound selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds described in Table P (described below), is effective against, for example, fungi and disease-transmitting fungi, as well as plant pathogenic bacteria and viruses. Examples of these fungi and disease-transmitting fungi, as well as plant pathogenic bacteria and viruses, are as follows: Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. such as Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Aspergillus niger, and Aspergillus terrus, and Aureobasidium spp. such as Aureobasidium pullulans. Botryosphaeria spp., such as Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria dothidea, and Botryosphaeria obtusa; Botrytis spp., such as Botrytis cinerea; Candida spp., such as Candida albicans, Candida glabrata, Candida krusei, Candida lusitaniae, Candida parapsilosis, and Candida tropicalis.), Cephaloascus fragrans, Ceratocystis spp., Cercospora spp. such as Cercospora arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. such as Colletotrichum musae, Cryptococcus neoformans neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erysiphe spp. such as Erwinia amylovora and E. cichoracearum, Eutypa rata Fusarium spp., such as Fusarium lata, Fusarium culmorum, Fusarium graminearum, Fusarium langsethiae, Fusarium moniliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium subglutinans, and Fusarium solani.Histoplasma species such as Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., and Histoplasma capsulatum spp., Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. such as M. graminicola and M. pomi, Oncobasidium theobromaeon theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. such as P. digitatum and P. italicum, Petriellidium spp., and Peronosclerospora maydis (P.maydis, Peronosclerospora spp. such as Peronosclerospora philippinensis and P. sorghi, Peronosclerospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phytophthora spp. such as Phomopsis viticola and P. infestans, Plasmopara spp., such as P. halstedii and P. viticola, Pleospora spp., Podosphaera spp., such as P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp. Pseudoperonospora spp. such as P. cubensis and P. humuli, Puccinia spp. such as Pseudopeziza tracheiphila, P. hordei, Puccinia recondita, P. striiformis, and P. triticina, Pyrenopeziza spp.), Pyrenophora spp., Pyricularia spp. such as Pyricularia oryzae (P. oryzae), Pythium spp. such as Pythium ultimum (P. ultimum), Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp., Scedosporium spp. such as Scedosporium apiospermum and Scedosporium prolificans (S. prolificans), spp.), Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., Septoria spp. such as S. nodorum and S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (= Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp., Trichoderma spp. such as T. harzianum, T. pseudokoningii, and T. viride, and Trichophyton spp.), Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp. such as V. inaequalis, Verticillium spp., and Xanthomonas spp.

[0130] The compounds of formula (I) according to the present invention can be used not only on turf, ornamental plants such as flowers, shrubs, broad-leaved or evergreen trees, such as conifers, but also for trunk injection, pest control, etc.

[0131] Within the scope of the present invention, target crops and / or useful plants to be protected typically include berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar beet and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus fruits, nectarine, peach, pear and plum; grasses, such as dactylon, strawberry vine, bean weed, rice bran, fescue, rye, St. Augustine grass. and lawn grass; aromatic herbs such as basil, borage, chives, coriander, lavender, lovage, peppermint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, groundnuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as grapes.

[0132] The term "useful plants" should also be understood to include useful plants that have been rendered tolerant to herbicides or classes of herbicides such as bromoxynil (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors) as a result of conventional breeding or genetic engineering methods. Crops that have been rendered tolerant to imidazolinones, such as imazamox, by conventional methods of breeding (mutagenesis) include, for example, Clearfield® summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0133] It should be understood that the term "useful plants" also includes useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0134] Examples of such plants include: YieldGard® (a corn variety that expresses the CryIA(b) toxin); YieldGard Rootworm® (a corn variety that expresses the CryIIIB(b1) toxin); YieldGard Plus® (a corn variety that expresses the CryIA(b) and CryIIIB(b1) toxins); Starlink® (a corn variety that expresses the Cry9(c) toxin); Herculex I® (a corn variety that expresses the CryIF(a2) toxin and phosphinothricin N-acetyltransferase (PAT), an enzyme that confers resistance to glufosinate ammonium herbicides); NuCOTN 33B® (a cotton variety that expresses the CryIA(c) toxin); Bollgard I® (a cotton variety that expresses the CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxins); NewLeaf® (a potato variety expressing CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) resistance trait), Agrisure® RW (a corn rootworm resistance trait), and Protecta®.

[0135] It should be understood that the term "crop plant" also includes crop plants that have been transformed using recombinant DNA techniques to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0136] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; or insecticidal proteins derived from Bacillus thuringiensis, such as δ-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3, or Vip3A; or bacteria symbiotic to nematodes, e.g., Photorhabdus luminescens, Xenorhabdus nematophilus, or the like. insecticidal proteins of Xenorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, corn-RIP, abrin, rufin, saporin steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as blockers of sodium channels or calcium channels, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0137] Furthermore, it should be understood that the delta-endotoxins related to the present invention, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative plant insecticidal proteins (Vips), such as Vip1, Vip2, Vip3, or Vip3A, can also be, in particular, hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins (see, for example, WO 02 / 15701). An example of a truncated toxin is known as truncated Cry1Ab. Modified toxins have one or more amino acids substituted in a naturally occurring toxin. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin G recognition sequence is inserted into the Cry3A toxin (see WO 2003 / 018810).

[0138] Such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP 0374753, WO 93 / 07278, WO 95 / 34656, EP 0427529, EP 0451878 and WO 03 / 052073.

[0139] Processes for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. Deoxyribonucleic acids of the CryI type and their production are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0140] The toxins contained in the genetically modified plants confer resistance to harmful insects found in all insect taxa, but particularly in beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0141] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known and commercially available. Examples of such plants include: YieldGard® (a corn variety expressing the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and phosphinothricin N-acetyltransferase (PAT), an enzyme that confers tolerance to glufosinate-ammonium herbicides); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); Vipcot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) resistance trait), and Protecta®.

[0142] Further examples of such genetically modified crops include: 1.1. Bt11 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize (Zea mays) conferred resistance to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) by recombinant expression of a truncated Cry1Ab toxin. Bt11 maize also conferred resistance to the herbicide glufosinate-ammonium by recombinant expression of the PAT enzyme. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically modified maize (Zea mays) conferred resistance to European corn borers (Ostrinia nubilalis and Sesamia nonagrioides) through recombinant expression of the Cry1Ab toxin. Bt176 maize also conferred resistance to the herbicide glufosinate-ammonium through recombinant expression of the PAT enzyme. 3. MIR604 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize conferred insect resistance by recombinantly expressing a modified Cry3A toxin. The toxin is Cry3A055 modified by inserting a cathepsin-G-protease recognition sequence. The generation of such transgenic maize plants is described in WO 2003 / 018810. 4. MON 863 maize, registration number C / DE / 02 / 9, from Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON 863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. IPC 531 Cotton, registration number C / ES / 96 / 02, from Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. 6. 1507 corn from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maize genetically modified to express the Cry1F protein for resistance to certain Lepidoptera insects and the PAT protein for tolerance to the glufosinate-ammonium herbicide. 7. NK603 x MON 810 maize, registration number C / GB / 02 / M3 / 03, from Monsanto Europe SA270-272 Avenue de Tervuren, B 1150 Brussels, Belgium. This conventionally bred hybrid maize variety was obtained by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 maize recombinantly expresses the CP4 EPSPS protein from Agrobacterium sp. strain CP4, which confers tolerance to Roundup® (containing glyphosate) herbicides, as well as the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain lepidopteran insects, such as the European corn borer.

[0143] The compounds of formula (I) according to the invention are effective against phytopathogenic diseases, in particular phytopathogenic fungi, such as Alternaria species on fruits, vegetables and potatoes; Botrytis cinerea on strawberries, tomatoes, sunflowers, pulses, vegetables and grapes; Rhizoctonia solani on potatoes and vegetables; Uncinula necator on grapes; Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium on Cucurbits; Leveillula taurica on Cucurbits and Solanaceae crops. taurica; Fusarium spp. in cereals; Leptosphaeria spp. in cereals; and Zymospetoria spp. in cereals.

[0144] As used herein, the term "habitat" means the field in which the plants are growing or in which the seeds of the plants to be cultivated have been sown or will be sown in the soil, including the soil, the seeds and seedlings, and the established vegetation.

[0145] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, trunks, stems, foliage, and fruits.

[0146] The term "plant propagation material" is understood to refer to reproductive parts, such as seeds, of plants, and vegetative parts, such as cuttings or tubers, for example potatoes, which can be used for their propagation. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Mention may also be made of germinated plants and seedlings that are to be transplanted after germination or emergence from the soil. These seedlings can be protected by treating them in whole or in part by immersion before transplanting. Preferably, "plant propagation material" is understood to refer to seeds.

[0147] The compounds of formula (I) according to the present invention can be used in their original form or, preferably, together with adjuvants conventionally used in the field of formulation. For this purpose, they can be formulated in a known manner as emulsifiable concentrates, coatable pastes, ready-to-spray or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusting powders, granules, or even encapsulated in polymeric materials. The application method, such as spraying, atomizing, dusting, granulation, coating, or pouring, as well as the type of composition, are selected depending on the intended purpose and the circumstances. The composition may also contain further adjuvants, such as stabilizers, antifoaming agents, viscosity modifiers, binders, or tackifiers, as well as fertilizers, sources of trace elements, or other formulations for achieving special effects.

[0148] Suitable carriers and adjuvants, for example those for agricultural applications, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0149] Suspension concentrates are aqueous formulations in which fine solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents, and may also contain anti-foaming and crystal growth inhibitors, as well as wetting agents to enhance activity. For use, these concentrates are diluted with water and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0150] Wettable powders are finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient held in a solid substrate. Typical solid substrates include fuller's earth, kaolin clay, silica, and other readily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient plus small amounts of wetting agents, dispersing agents, or emulsifying agents.

[0151] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may also contain a liquid carrier such as xylene, heavy aromatic naphtha, isophorone, and other non-volatile organic solvents. For use, these concentrates are dispersed in water or other liquid and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0152] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area requiring treatment. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corncob, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials capable of absorbing or coating the active compound. Granular formulations typically contain 5% to 25% of the active ingredient and may contain surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions or vegetable oils, and / or adhesive substances such as dextrin, adhesives, or synthetic resins.

[0153] Powders are free-flowing mixtures of the active ingredient with finely divided solids, such as talc, clay, flour, and other organic and inorganic solids, which act as dispersants and carriers.

[0154] Microcapsules typically contain droplets or granules of an active ingredient encapsulated in an inert, porous shell that allows the encapsulated material to escape into the surrounding environment at a controlled rate. The encapsulated droplets typically range from 1 to 50 microns in diameter. The encapsulated liquid typically comprises 50 to 95% of the capsule's mass and may contain a solvent in addition to the active compound. The encapsulated granules are generally porous granules with porous membranes sealing the pore openings and retaining the active chemical species in liquid form within the pores. The granule diameters are typically in the range of 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters. Granules can be formed by extrusion, agglomeration, or prilling, or can be naturally occurring. Examples of such materials include vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0155] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, and other organic solvents. Pressurized sprayers can also be used, which disperse the active ingredient in finely divided form by evaporation of the solvent carrier, which is a low-boiling dispersant.

[0156] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention into formulations of the type described above are known to those skilled in the art.

[0157] Examples of liquid carriers that can be used include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietic acid, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecane Examples of suitable carriers include citric acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol and amyl alcohol, tetrahydrofurfuryl alcohol, high molecular weight alcohols such as hexanol and octanol, ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. Generally, water is the preferred carrier for diluting concentrates.

[0158] Suitable solid carriers include, for example, talc, titanium dioxide, pyroferritic clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

[0159] A wide range of surfactants are advantageously used in both the liquid and solid compositions, especially those designed to be diluted with a carrier before application. When used, these agents typically comprise 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic, or polymeric in nature and may be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include salts of lauryl sulfate, such as diethanolammonium lauryl sulfate; alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; nonylphenol-C; 18 Alkylphenol-alkylene oxide adducts such as ethoxylates; Tridecyl alcohol-C 16 alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters.

[0160] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light-blocking agents, compatibilizers, defoamers, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants, and adhesives.

[0161] In addition, other biocidal active ingredients or compositions can be used in the method of the present invention in combination with the composition of the present invention, and these can be applied simultaneously or sequentially with the composition of the present invention.When applied simultaneously, these additional active ingredients can be formulated together with the composition of the present invention, or can be mixed, for example, in a spray tank.These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0162] Pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0163] Additionally, the compositions of the present invention may be applied in conjunction with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0164] The compound of formula (I) according to the present invention is usually used in the form of agrochemical compositions, and can be applied to the cropland or the plants to be treated simultaneously or successively with other compounds.These other compounds can be, for example, fertilizers or trace element sources or other preparations that affect plant growth.They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, and if necessary, also contain other carriers, surfactants or application-promoting adjuvants that are commonly used in the technical field of formulation.

[0165] The compounds of formula (I) according to the invention can be used in the form of (fungicidal) compositions for controlling or protecting against phytopathogenic microorganisms, comprising, as active ingredients, at least one compound of formula (I) or at least one preferred individual compound as defined herein, in free form or in the form of an agrochemically useful salt, and at least one adjuvant as defined above.

[0166] Therefore, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) according to the present invention, an agriculturally acceptable carrier, and optionally an adjuvant.Agriculturally acceptable carriers are, for example, carriers suitable for agricultural use.Agricultural carriers are well known in the art.Preferably, the composition may comprise, in addition to the compound of formula (I), at least one or more pesticidal active compounds, for example, additional fungicidal active ingredients.

[0167] The compound of formula (I) according to the invention may be the only active ingredient of the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, etc. In some cases, the additional active ingredients may result in unexpected synergistic effects.

[0168] Examples of suitable additional active ingredients include: acyclic amino acid fungicides, nitrogen-containing aliphatic fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, Plant-based fungicides, bridged diphenyl-based fungicides, carbamate-based fungicides, carbanilate-based fungicides, conazole-based fungicides, copper-based fungicides, dicarboximide-based fungicides, dinitrophenol-based fungicides, dithiocarbamate-based fungicides, dithiolane-based fungicides, fluamide-based fungicides, fluanilide-based fungicides, hydrazide-based fungicides, imidazole-based fungicides, water Silver-based fungicides, morpholine-based fungicides, organophosphorus-based fungicides, organotin-based fungicides, oxathiin-based fungicides, oxazole-based fungicides, phenylsulfamide-based fungicides, polysulfide-based fungicides, pyrazole-based fungicides, pyridine-based fungicides, pyrimidine-based fungicides, pyrrole-based fungicides, quaternary ammonium-based fungicides, quinoline-based fungicides, quinone-based fungicides, Quinoxaline-based fungicides, strobilurin-based fungicides, sulfonanilide-based fungicides, thiadiazole-based fungicides, thiazole-based fungicides, thiazolidine-based fungicides, thiocarbamate-based fungicides, thiophene-based fungicides, triazine-based fungicides, triazole-based fungicides, triazolopyrimidine-based fungicides, urea-based fungicides, valinamide-based fungicides and zinc-based fungicides.

[0169] Examples of suitable additional active ingredients include: petroleum oils, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenyl phenyl sulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, alamite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate Ndil, bixafen, brofenvalerate, bromocyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphechlor, carbanolate, carbophenothion, cymiazole, chinomethionate, chlorbenside, chlordimeform, chlordimeform hydrochloride, chlorphenetole, chlorfenson, chlorfen sulfide, chlorobenzilate, chloromebuform, chloromethiron, chloropropanol Lopirate, Chlorthiophos, Cinerin I, Cinerin II, Cinerins, Closantel, Coumaphos, Crotamiton, Crotoxyphos, Kufraneb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-methyl, Demeton-O, Demeton-O-methyl, Demeton-S, Demeton-S-methyl, Demeton-S-methyl sulfone, Dichlofluanid, Dichlorvos, Dicrifos, Dienochlor, Dimefox, Zinex, Zinex-diclexin, Zinox Cap-4, Dinocap-6, Dinoctone, Dinopentone, Dinosulfone, Dinotervone, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dofenapine, Doramectin, Endothion, Eprinomectin, Ethoate-methyl, Etrimphos, Fenazaflor, Fenbutatin Oxide, Fenothiocarb, Fenpyrad, Fenpyroximate, Fenpyrazamine, Fenson, Fentrifanil, Flubenzimine, Flucycloxuron, Fluenethyl, Fluorobenside, FMC 1137, Formetanate, Formetanate Hydrochloride, Formoparanate, γ-HCH, Gliodin, Halfenprox, Hexadecyl Cyclopropanecarboxylate, Isocarbophos, Jasmolin I,Jasmolin II, iodofenphos, lindane, malonobene, mecarbam, mefosfolan, mesulfen, methacrifos, methyl bromide, metolcarb, mexacarbate, milbemycin oxime, mipafox, monocrotophos, morphothion, moxidectin, naled, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifururidide, nikkomycin, nitrilacarb, nitrilacarb·1:1 zinc chloride complex, omethoate, oxydeprophos, oxydi Sulfoton, pp'-DDT, parathion, permethrin, fenkapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxur, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pirimitate, quinalphos, quinthiofos, R-1492, phosglycine, rotenone, shradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflobidazin, tau Fluvalinate TEPP, Terbam, Tetradifon, Tetrasulf, Thiafenox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringiensin, Triamiphos, Triatene, Triazophos, Triazuron, Trifenofos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Dichloron, Dichlorophen, Endothal, Fentin, Hydrated lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Crufomate, Piperazine, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodisin, fenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, octhilinone, oxolinic acid, oxytetracycline,Hydroxyquinoline potassium sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana granulovirus (GV), Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera nucleopolyhedrovirus (NPV), Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica nucleopolyhedrovirus (ACP), NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora bacteriophora and Heterorhabditis megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae nucleopolyhedrovirus (NPV),Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and Neodiprion lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii lecanii), afolate, bisazilyl, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl afolate, molzide, penfluron, tepa, thiohempa, thiotepa, toretamine, uredepa, (E)-dec-5-en-1-yl acetate in combination with (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E,Z)-tetradec-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal,(Z)-Hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methyl- Chiloctadec-1-ene, 4-methylnonan-5-ol in combination with 4-methylnonan-5-one, α-multistriatin, brevicomin, codrelure, codlemone, curua, disparlua, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicale, ethyl 4-methyloctanoate, eugenol, frontalin, grandolure, grandolure I, grandolure II, grandolure III, grandolure IV, hexalure, ipsdienol, ips Senol, Japonirua, Lineatin, Litirua, Lupulua, Medulua, Megatomoic Acid, Methyleugenol, Muscalua, Octadeca-2,13-dien-1-yl Acetate, Octadeca-3,13-dien-1-yl Acetate, Olfuralua, Orictalua, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl Acetate, Trimedulua, Trimedulua A, Trimedulua B1, Trimedulua B2, Trimedulua C, Trancol, 2-(Octylthio)ethanol, Butopyroneoxyl, Butoxy(po propylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyl toluamide, dimethyl carbamate, dimethyl phthalate, ethyl hexanediol, hexamide, methoxbutyl, methyl neodecanoate, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 1,3-dichloropropene in combination, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate,2,2-Dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethene, Alcohol, 2-chlorovinyldiethyl phosphate, 2-imidazolidone, 2-isovalerylindan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, alixycarb, α-ecdysone, aluminum phosphide, aminocarb, anabasine, thidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin (Bacillus thuringiensis delta endotoxins), barium hexafluorosilicate, barium sulfide, varsuline, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenbiphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenite, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sevadine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, cumitoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, 5-methylpyrazol-3-yl diethyl phosphate, dilol, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb,Fenitrothion, fenoxacrim, fenpyrithrin, fensulfothion, fenthion-ethyl, flucofuron, fosmetilan, fospirate, fostietan, furathiocarb, freslin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikincarb, IPSP, isazophos, isobenzan, isodrin, isofenphos, isolane, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kerevan, kinoprene, lead arsenate, leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menasone, mercurous chloride, mesulfenphos, metam , metam potassium, metam sodium, methanesulfonyl fluoride, methocrotophos, methoprene, methotrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, Mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion methyl, pentachlorophenol, pentachlorophenyl laurate, PH 60-38, fenkapton, phosnichlor, phosphine, phoximmethyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, cassia, quinalphos-methyl, quinothion, lafoxanide, resmethrin, rotenone, cadethrin, ryania, ryanodine, sabadila, shradan, cebufos, SI-0009, tiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide,Sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron sodium, sulfuryl fluoride, sulprofos, tar oil, thazimcarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap sodium, tralomethrin, trans-permethrin, triazamate, trichlorometaphos-3, trichloronate, trimethacarb, tolprocarb, triclopiricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphide, zolaprofos, meperfluthrin, tetrachloroethane Methylfluthrin, bis(tributyltin) oxide, bromoacetamide, iron(III) phosphate, niclosamide olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, anicifluprine, benclothiaz, cytokinins, DCIP, furfural, isamidophos, kinetin, Myrothecium verrucaria (Myrothecium verrucaria) compound, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis) extract, α-chlorohydrin, Antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciliroside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone,Farnesol in combination with nerolidol, berubutin, MGK 264, piperonyl butoxide, piprotal, propyl isomers, S421, sesamex, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chlorinconazide, mercuric oxide, thiophanate methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol , furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidil phenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, diclozolin, myclozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodin, imipenem Noctadine, azoxystrobin, dimoxystrobin, enestroblin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine copper,Nitrothal-isopropyl, edifenphos, iprobenfos, phosdifen, tolclofos-methyl, anilazine, benthiavalicarb, blasticidin S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, Flusulfamide, fluxapyroxad, fenhexamid, fosetylaluminum, hymexazole, iprovalicarb, cyazofamid, metasulfocarb, metrafenone, pencycuron, phthalide, polyoxins, propamocarb, pyribencarb, proquinazide, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, valifenalate, zoxamide, mandipropamide, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflu Metofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucipram, isotianil, dipimethitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carboxamide rubonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, cumoxystrobin, rubenmixianan, diclobenthiazox, mandestrobin,3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl, tert-Butyl [(4-(4,5-dichlorothiazol-2-yl)oxy)-2,5-dimethyl-N-[(4-(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethyl-N-methyl-4-(4-methyl-2-pyridyl)-2-methyl-2-pyridyl]carbamate, pyraziflumide, inpirfluxam, tolprocarb, mefentrifluconazole, bufentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-N-methyl-4-(4-methyl-2-pyridyl)-2-methyl-2-pyridyl]carbamate -phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate but-3-ynyl, N-[[5-[4-(2,4-dimethylphenyl)triazole methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4 -(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (can be prepared from the method described in WO 2020 / 056090), 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (can be prepared from the method described in WO 2020 / 056090), N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-

[0033] methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared from 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 (which can be prepared from 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- -methyl-pyridazine-4-carboxamide (which can be prepared from 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 (which can be prepared from the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2-methyl-pyridazine-4-carboxamide] N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide (which can be prepared from the method described in WO 2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobilin, fenamacryl, 5-amino-1,3,4-Thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, flutianil, fluopimomide, pyrapropoin, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazoline) [4'-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester, (Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]prop-2-enoic acid methyl ester, (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl) ... methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (these compounds can be prepared from the method described in WO 2020 / 079111), (Z )-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate methyl (these compounds can be prepared from the method described in WO 2020 / 193387), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 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, 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, Trinexapac, Cumoxystrobin, Zongshenmycin, Thio Diazole copper, thiazole zinc, amethotractin, iprodione, seboxylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy) N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared by the method described in WO 2015 / 155075). N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from 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, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2 -trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide Fluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl )-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridine, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3 , 3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl) )-1,2,4-Oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate ethyl, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from 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 (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3 -[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylate (4-phenoxyphenyl)methyl (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2 ,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 2011 / 138281), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2 -methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in WO 2016 / 202742);2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl )-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the method described in WO 2018 / 202428);

[0170] The compounds of the present invention can also be used in combination with roundworm repellents. Such roundworm repellents include compounds selected from the macrocyclic lactone class of compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives, as described in EP 0357460, EP 0444964, and EP 0594291. Additional roundworm repellents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Pat. No. 5,015,630, WO 9415944, and WO 9522552. Further ascaricides include benzimidazoles such as albendazole, cambandazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole and other ascaricides that make up this class. Further ascaricides include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Further ascaricides include trematocides such as triclabendazole and clorsulon and cestocides such as praziquantel and epsiprantel.

[0171] The compounds of the present invention can be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of ascaricides and antiparasitic oxazolines such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 and German Patent No. 19,520,936.

[0172] The compounds of the invention may also be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents described in WO 9615121, as well as with cyclic depsipeptides with ascaricidal activity such as those described in WO 9611945, WO 9319053, WO 9325543, EP 0626375, EP 0382173, WO 9419334, EP 0382173 and EP 0503538.

[0173] The compounds of the invention can be used in combination with other ectoparasiticides, for example, fipronil, pyrethroids, organophosphates, insect growth regulators such as lufenuron, ecdysone agonists such as tebufenozide, and neonicotinoids such as imidacloprid.

[0174] The compounds of the present invention may be used in combination with terpene alkaloids such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0175] Other examples of such biologically active compounds that can be used in combination with the compounds of the present invention include, but are not limited to:

[0176] Organophosphate esters: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Cadusafos, Chlorethoxyphos, Chlorpyrifos, Chlorfenvinphos, Chlormephos, Demeton, Demeton-S-methyl, Demeton-S-methylsulfone, Dialifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Ethoprophos, Etrimphos, Fanflu, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonophos, Formothion, Fosthiazate, Heptenophos, Isazophos, Isothioate, Iso Xathion, malathion, methacrifos, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proethamfos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion.

[0177] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

[0178] Pyrethroids: acrinatin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate 5-benzyl-3-furylmethyl, bifenthrin, β-cyfluthrin, cyfluthrin, α-cypermethrin, β-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cytisrin, cyphenothrin methacrylate, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, λ-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, θ-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, ζ-cypermethrin.

[0179] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentadine, b) Ecdysone agonists: Halofenozide, Methoxyfenozide, Tebufenozide, c) Juvenile hormone-like substances: Pyriproxyfen, Methoprene (including S-Methoprene), Fenoxycarb, d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0180] Other antiparasitic agents: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, campechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclor, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzin, flufenprox, fluproxifen, ha Lofenprox, hydramethylnon, IKI-220, Kanemite, NC-196, Niemgard, Nidinolterfuran, Nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymetrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn, trinactin, belbutin, Bertalec, YI-5301.

[0181] Biological agents: Bacillus thuringiensis ssp. aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0182] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0183] Other biological agents: enrofloxacin, febantel, penetamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiofur, carprofen, metaflumizone, praziquantel, triclabendazole.

[0184] A mixture of a compound of formula (I) shown below with an active ingredient is preferred. The abbreviation "TX" means one compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2), (I-A3), or one compound selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds described in Table P (described below): A compound selected from the group consisting of the following substances: petroleum oil + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic trioxide + TX, azobenzene + TX, azotoa To + TX, Benomyl + TX, Benoxafos + TX, Benzyl Benzoate + TX, Bixafen + TX, Brofenvalerate + TX, Bromocyclen + TX, Bromophos + TX, Bromopropylate + TX, Buprofezin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium Polysulfide + TX, Camphechlor + TX, Carbanolate + TX, Carbophenothion + TX, Cymiazole + TX, Chinomethionate + TX, Chlorbenside + TX, Chlordimeform + TX, Chlordimeform Hydrochloride + TX , Chlorphenetole + TX, Chlorfenson + TX, Chlorphenesulfide + TX, Chlorobenzilate + TX, Chlormebform + TX, Chlormethiuron + TX, Chloropropylate + TX, Chlorthiophos + TX, Cinerin I + TX, Cinerin II + TX, Cinerins + TX, Closantel + TX, Coumaphos + TX, Crotamiton + TX, Crotoxyphos + TX, Kufraneb + ​​TX, Cyanthoate + TX, DCPM + TX, DDT + TX, Demefion + TX, Demefion-O + TX, Demefion-S + TX, Demeton-methyl + TX , Demeton-O+TX, Demeton-O-methyl+TX, Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Dicrifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-Diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX,Dofenapine +TX, Doramectin +TX, Endothion +TX, Eprinomectin +TX, Ethoate methyl +TX, Etrimphos +TX, Fenazaflor +TX, Fenbutatin oxide +TX, Fenothiocarb +TX, Fenpyrad +TX, Fenpyroximate +TX, Fenpyrazamine +TX, Fenson +TX, Fentrifanil +TX, Flubenzimine +TX, Flucycloxuron +TX, Fluenethyl +TX, Fluorobenside +TX, FMC1137 +TX, Formetanate +TX, Formetanate Hydrochloride +TX, Formparanate +TX, γ-HCH +TX, Gliodin +TX, Halfenprox +TX, Hexadecyl Cyclopropanecarboxylate +TX, Isocarbophos +TX, Jasmolin I +TX, Jasmolin II +TX, Iodofenphos +TX, Lindane +TX, Malonoben +TX, Mecarbam +TX, Mefosorane +TX, Mesulfen +TX, Methacrifos +TX, Methyl Bromide +TX, Metolcarb +TX, Mexacarbate +TX, Milbemycin Oxime +TX, Mipafox +TX, Monocrotophos +TX, Morphothion +TX, Moxidectin +TX, Naled + TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifururizide + TX, nikkomycin + TX, nitrilacarb + TX, nitrilacarb 1:1 zinc chloride complex + TX, omethoate + TX, oxydeprophos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, fencapton + TX, phosalone + TX, phospholan + TX, phosphamidon + TX, polychloroterpenes + TX, polynactin + TX, Proclonol +TX, Promacyl +TX, Propoxur +TX, Protidathion +TX, Protoate +TX, Pyrethrin I +TX, Pyrethrin II +TX, Pyrethrins +TX, Pyridaphenthion +TX, Pirimitate +TX, Quinalphos +TX, Quinthiofos +TX, R-1492 +TX, Phosglycine +TX, Rotenone +TX, Schradan +TX, Cebufos +TX, Selamectin +TX, Sofamid +TX, SSI-121 +TX, Sulfiram +TX, Sulfuramide +TX, Sulfotep +TX, Sulfur +TX, Diflobidazine +TX,Taufluvalinate + TX, TEPP + TX, Terbam + TX, Tetradifon + TX, Tetrasulf + TX, Thiafenox + TX, Thiocarboxim + TX, Thiofanox + TX, Thiometon + TX, Thioquinox + TX, Thuringiensin + TX, Triamiphos + TX, Triatene + TX, Triazophos + TX, Triazuron + TX, Trifenofos + TX, Trinactin + TX, Vamidothion + TX, Vaniliprole + T X, bethoxadin +TX, copper dioctanoate +TX, copper sulfate +TX, sibutrin +TX, dichloron +TX, dichlorophen +TX, endothall +TX, fentin +TX, hydrated lime +TX, nabam +TX, quinoclamine +TX, quinonamide +TX, simazine +TX, triphenyltin acetate +TX, triphenyltin hydroxide +TX, crufomate +TX, piperazine +TX, thiophanate +TX, chloralose +TX, fenthion +T X, pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodisin + TX, fenaminosulf + TX, formaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin + TX Gamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana granulovirus (Adoxophyes orana GV) + TX, Agrobacterium radiobacter (Agrobacterium radiobacter) + TX, Amblyseius spp. (Amblyseius spp.) + TX, Anagrapha falcifera nucleopolyhedrovirus (Anagrapha falcifera NPV) + TX, Anagrus atomus (Anagrus atomus) + TX,Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica nuclear polyhedrosis virus (NPV) + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella granulosa virus (GV) + TX, Dacnusa sibirica sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and Heterorhabditis megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae nucleopolyhedrovirus (NPV) + TX, Metaphycus herbolis helvolus) + TX, Metarhizium anisopliae var. acridum (Metarhizium anisopliae var. acridum) + TX, Metarhizium anisopliae var. anisopliae (Metarhizium anisopliae var. anisopliae) + TX,Neodiprion sertifer nuclear polyhedrosis virus (NPV) and Neodiprion lecontei nuclear polyhedrosis virus (NPV) + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii) + TX, Afolate + TX, Bisazilyl + TX, Busulfan + TX, Dimatif + TX, Hemel + TX, Hempa + TX, Metepa + TX, Methiotepa + TX, Methyl Afolate + TX, Molzide + TX, Penfluron + TX, Tepa + TX, Thiohempa + TX, Thiotepa + TX, Tretamine + TX, Uredepa + TX, (E)-Decem-5-en-1-yl acetate and (E)-Decem-5- combination with hexadec-11-enal + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX,(Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradec-9,11-dien-1-yl acetate + TX, (9Z,12E)-tetradec-9,12-dien-1-yl, Dodec-8-en-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one combination + TX, α-multistriatin + TX, Brevicomin + TX, Codrelure + TX, Codlemone + TX, Cureure + TX, Disparlua + TX, Dodec-8-en-1-yl acetate + TX, Dodec-9-en-1-yl acetate + TX, Dodec-8,10-dien-1-yl acetate + TX, Dominicale + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Glycerol Landrua + TX, Grandrua I + TX, Grandrua II + TX, Grandrua III + TX, Grandrua IV + TX, Hexalua + TX, Ipsdienol + TX, Ipsenol + TX, Japonilua + TX, Lineatin + TX, Litulua + TX, Lupulua + TX, Medulua + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalua + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Olfrulua + TX, Orictalua + TX, Ostramon + TX , Cigla + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedlure + TX, Trimedlure A + TX, Trimedlure B1 + TX, Trimedlure B2 + TX, Trimedlure C + TX, Trancol + TX, 2-(octylthio)ethanol + TX, Butopyroneoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Diethyltoluamide + TX, Dimethyl carbate + TX, Dimethyl phthalate + TX, Ethyl hexanediol + TX, hexamide + TX, methoquinbutyl + TX, methyl neodecanamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane and 1,3-dichloropropene combined + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methylphosphate + TX,2-(1,3-Dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1 -ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixycarb + TX, α-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis delta endotoxins + TX, barium hexafluorosilicate + TX, barium sulfide + TX, valsuline + TX, Bayer 22 / 190 + TX, Bayer 22408+TX, β-cyfluthrin+TX, β-cypermethrin+TX, bioethanomethrin+TX, biopermethrin+TX, bis(2-chloroethyl) ether+TX, borax+TX, bromfenbiphos+TX, bromo-DDT+TX, bufencarb+TX, butacarb+TX, butathiophos+TX, butonate+TX, calcium arsenite+TX, calcium cyanide+TX, carbon disulfide+TX , carbon tetrachloride + TX, cartap hydrochloride + TX, sevadin + TX, chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocitrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, chumithoate + TX, cryolite + TX,CS 708+TX, cyanofenphos+TX, cyanophos+TX, cyclethrin+TX, cythioate+TX, d-tetramethrin+TX, DAEP+TX, dazomet+TX, decarbofuran+TX, diamidaphos+TX, dikapton+TX, diclofenthion+TX, dicresyl+TX, dicyclanil+TX, dieldrin+TX, 5-methylpyrazol-3-yl diethyl phosphate+TX, dilol+TX, dimefluthrin+TX, dimethane+TX, dimethryn+TX, dimethylvinphos+TX, dimethyllan+TX, dinoprop+TX, dinosam+TX, dinoseb+TX, diofenolan+TX, dioxabenzophos+TX, dicyclophos+TX, DSP+TX, ecdysterone+TX, EI 1642+TX, EMPC+TX, EPBP+TX, Ethaphos+TX, Ethiofencarb+TX, Ethyl formate+TX, Ethylene dibromide+TX, Ethylene dichloride+TX, Ethylene oxide+TX, EXD+TX, Fenchlorphos+TX, Fenetacarb+TX, Fenitrothion+TX, Fenoxacrim+TX, Fenpyrithrin+TX, Fensulfothion+TX, Fenthion-ethyl+TX, Flucofuron+TX, Fosmetilan+TX, Fospirate+TX, Fostietan+TX, Furathiocarb+TX, Frethlin+TX, Guazatine+TX, Guazatine acetate+TX, Sodium tetrathiocarbonate+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterofos+TX, HHDN+TX, Cyanide Hydrogen + TX, Hikincarb + TX, IPSP + TX, Isazophos + TX, Isobenzan + TX, Isodrin + TX, Isofenphos + TX, Isolane + TX, Isoprothiolane + TX, Isoxathion + TX, Juvenile Hormone I + TX, Juvenile Hormone II + TX, Juvenile Hormone III + TX, Kelevan + TX, Kinoprene + TX, Lead Arsenate + TX, Leptophos + TX, Lilimphos + TX, Ritidathion + TX, m-Cumenylmethylcarbamate + TX, Magnesium Phosphide + TX, Magidox + TX, Mecarfone + TX, Menasone + TX, Mercurous Chloride + TX, Mesulfenphos + TX, Metam + TX, Metam Potassium + TX, Metam Sodium + TX, Methanesulfonyl Fluoride + TX, Metocrotophos + TX, Methoprene + TX, Methotrin + TX,Methoxychlor + TX, Methyl isothiocyanate + TX, Methyl chloroform + TX, Methylene chloride + TX, Methoxadiazone + TX, Mirex + TX, Naphthalophos + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nicotine sulfate + TX, Nithiazine + TX, Nornicotine + TX, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-diethyl O-6-methyl-2-propyl phosphorothioate Rimidin-4-yl + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, Oleic acid + TX, para-dichlorobenzene + TX, parathion methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH60-38 + TX, fenkapton + TX, phosnichlor + TX, phosphine + TX, phoxim methyl + TX, pyrimetaphos + TX, polychlorodicyclopentadiene isomers + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene II + TX, precocene II I+TX, Primidophos+TX, Profluthrin+TX, Promecarb+TX, Prothiofos+TX, Pyrazophos+TX, Pyresmethrin+TX, Cassia+TX, Quinalphos-methyl+TX, Quinothione+TX, Lafoxanide+TX, Resmethrin+TX, Rotenone+TX, Kadesrin+TX, Rhiania+TX, Ryanodine+TX, Sabadila+TX, Schradan+TX, Cebufos+TX, SI-0009+TX, Tiapronil+TX, Sodium arsenite+TX, Sodium cyanide+TX, Sodium fluoride+TX, Sodium hexafluorosilicate +TX, sodium pentachlorophenoxide +TX, sodium selenate +TX, sodium thiocyanate +TX, sulcofuron +TX, sulcofuron sodium +TX, sulfuryl fluoride +TX, sulprofos +TX, tar oil +TX, thazimcarb +TX, TDE +TX, tebupirimfos +TX, temephos +TX, telalethrin +TX, tetrachloroethane +TX, cyclofos +TX, thiocyclam +TX, thiocyclam hydrogen oxalate +TX, thionazine +TX, thiosultap +TX, thiosultap sodium +TX, tralomethrin +TX,trans-permethrin +TX, triazamate +TX, trichlorometaphos-3 +TX, trichloronate +TX, trimethacarb +TX, tolprocarb +TX, triclopyricarb +TX, triplenone +TX, veratridine +TX, veratrine +TX, XMC +TX, zetamethrin +TX, zinc phosphide +TX, zolaprofos +TX, meperfluthrin +TX, tetramethylfluthrin +TX, bis(tributyltin) oxide +TX, bromoacetamide +TX, iron(III) phosphate +TX, niclosamide olamine +TX, tributyltin oxide +TX, pyrimorph +TX, triphenmorph +TX, 1 , 2-Dibromo-3-chloropropane + TX, 1,3-Dichloropropene + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-Isopentenylaminopurine + TX, 2-Fluoro-N-(3-methoxyphenyl)9H-purin-6-amine + TX, Benclotiaz + TX, Cytokinins + TX, DCIP + TX, Furfural + TX, Isamidophos + TX, Kinetin + TX, Myrothecium verrucaria (Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenols + TX, zeatin + TX, potassium ethylxanthogenate + TX, acibenzolar + TX, acibenzolar-S-methyl + TX, giant knotweed (Reynoutria sachalinensis) extract +TX, α-chlorohydrin +TX, Antu +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumarol +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX, ergocalciferol +TX, flocoumafen +TX, fluoroacetamide +TX, flupropazine +TX, flupropazine hydrochloride +TX, norbormide +TX, fosacetim +TX, phosphorus +TX, pindone +TX, pyrinuron +TX, sciriloside +TX, sodium fluoroacetate +TX, thallium sulfate +TX,Warfarin + TX, 2-(2-butoxyethoxy)ethyl piperonate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol and nerolidol combination + TX, verbutin + TX, MGK264 + TX, piperonyl butoxide + TX, Piprotar, propyl isomers + TX, S421 + TX, sesamex + TX, sesasmolin + TX, sulfoxide + TX, anthraquinone + TX, copper naphthenate + TX, copper oxychloride + TX, dicyclopentadiene + TX, thiram + TX, zinc naphthenate + TX, ziram + TX, imanin + TX, ribavirin + TX, mercuric oxide + TX, thiophanate methyl + TX, azaconazole + TX, bitertanol + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX , fenbuconazole +TX, fluquinconazole +TX, flusilazole +TX, flutriafol +TX, furametpyr +TX, hexaconazole +TX, imazalil +TX, imibenconazole +TX, ipconazole +TX, metconazole +TX, myclobutanil +TX, paclobutrazol +TX, pefurazoate +TX, penconazole +TX, prothioconazole +TX, pyrifenox +TX, prochloraz +TX, propiconazole +TX, pyrisoxazole +TX, simeconazole +TX, tebuconazole +TX, tetraco Nazole + TX, Triadimefon + TX, Triadimenol + TX, Triflumizole + TX, Triticonazole + TX, Ancymidol + TX, Fenarimol + TX, Nuarimol + TX, Bupirimate + TX, Dimethirimol + TX, Ethirimol + TX, Dodemorph + TX, Fenpropidin + TX, Fenpropimorph + TX, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fludioxonil + TX, Benalaxyl + TX, Furalaxyl + TX, Meta Laxyl + TX, R-metalaxyl + TX, Ofurace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazole + TX, Chlozolinate + TX, Diclozolin + TX, Mycrozolin + TX, Procymidone + TX, Vinclozolin + TX, Boscalid + TX, Carboxin + TX, Fenfuram + TX, Flutolanil + TX, Mepronil + TX, Oxycarboxin + TX, Penthiopyrad + TX, Thifluzamide + TX, Dodin + TX, Iminoctadine + TX, Azoxystrobin + TX,Dimoxystrobin +TX, Enestrobulin +TX, Phenaminestrobin +TX, Flufenoxystrobin +TX, Fluoxastrobin +TX, Kresoxim-methyl +TX, Metominostrobin +TX, Trifloxystrobin +TX, Orysastrobin +TX, Picoxystrobin +TX, Pyraclostrobin +TX, Pyrametstrobin +TX, Pyraoxystrobin +TX, Ferbam +TX, Mancozeb +TX, Maneb +TX, Metiram +TX, Propineb +TX, Zineb +TX, Captafol +TX, Captan +T X, Fluorimide +TX, Folpet +TX, Tolylfluanid +TX, Bordeaux mixture +TX, Copper oxide +TX, Mancopper +TX, Oxine copper +TX, Nitrothar-isopropyl +TX, Edifenphos +TX, Iprobenfos +TX, Fosdifen +TX, Tolclofos methyl +TX, Anilazine +TX, Benthiavalicarb +TX, Blasticidin S +TX, Chloroneb +TX, Chlorothalonil +TX, Cyflufenamid +TX, Cymoxanil +TX, Cyclobutrifluram +TX, Diclocymet +TX, Diclomedine +TX, Di Chlorane +TX, Diethofencarb +TX, Dimethomorph +TX, Flumorph +TX, Dithianon +TX, Ethaboxam +TX, Etridiazole +TX, Famoxadone +TX, Fenamidon +TX, Fenoxanil +TX, Ferimzone +TX, Fluazinam +TX, Fluopicolide +TX, Flusulfamide +TX, Fluxapyroxad +TX, Fenhexamid +TX, Fosetylaluminum +TX, Hymexazole +TX, Iprovalicarb +TX, Cyazofamid +TX, Metasulfocarb +TX, Metrafenone +TX, Pencycuron +TX, phthalide +TX, polyoxins +TX, propamocarb +TX, pyribencarb +TX, proquinazide +TX, pyroquilon +TX, pyriophenone +TX, quinoxyfen +TX, quintozene +TX, tiadinil +TX, triazoxide +TX, tricyclazole +TX, triforine +TX, validamycin +TX, valifenalate +TX, zoxamide +TX, mandipropamide +TX, flubeneteram +TX, isopyrazam +TX, sedaxane +TX, benzovindiflupir +TX, pydiflumetofen +TX,3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isotianil + TX, dipimethitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino1,2-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 Ir-pyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, Fluindapyr + TX, Cumoxystrobin (Jiaxi angjunzhi) + TX, rubenmixianan + TX, diclobenthiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate tert-butyl + TX, pyridyl Diflumid + TX, Inpirfluxam + TX, Tolprocarb + TX, Mefentrifluconazole + TX, Ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX,[2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate + TX, N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate but-3-ynyl + TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl] Methyl carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethyl (1-(4-chlorophenyl)pyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, flurylpicoxamide + TX, fenpicoxamide + TX, tebufloquin + TX, ipflufenoquin + TX, quinofumelin + TX, isofetamide + TX, N-[2-[2,4-dichloro -phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, benzothiostrobin + TX, fenamacryl + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropoin + TX, picarbutrazox + TX,2-(Difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2-(Difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Methyltetraprole + TX, α-(1,1-dimethylethyl) -α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazole- 1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, cumoxystrobin + TX, zongshenmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino) )ethyl]ethane-1,2-diamine + TX, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX,N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared from the method described in WO 2015 / 155075), N'-[5-bromo-2-methyl-6-(2-propoxypropoxy), N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX (this compound can be prepared from 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 from 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 from the method described in WO 2019 / 110427 can be prepared from the method); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl ]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl) -8-Fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared from the method described in WO 2017 / 153380), 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-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 from the method described in WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5 -trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-Dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared from the method described in WO 2016 / 156085), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-Triazole-3-amine + TX. The compounds of this paragraph can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348, and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from 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 from the method described in WO 2017 / 029179); [2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2017 / 029179); [2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); [2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); propyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylate (4-phenoxyphenyl)methyl + TX (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']di Pyrrole-1,3,5,7(2H,6H)-tetrone + TX (this compound can be prepared from the method described in WO 2011 / 138281), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-Dimethyl-pent-3-enamide + TX (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl (3-methylisoxazol-5-yl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared from the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these The compound can be prepared from the method described in WO 2017 / 220485; 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared from the method described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]ethyl pyrazole-4-carboxylate + TX (this compound can be prepared from the method described in WO 2018 / 065414). can be prepared from the method described in PCT Publication No. 2018 / 158365; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX,N-[N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared from the method described in WO 2018 / 202428), chlorinconazide + TX, flumethylsulfolim + TX, fluoxythioconazole + TX, flufenoxadiazam + TX, methallylpicoxamide + TX.

[0185] The reference number in parentheses following the active ingredient, for example, [3878-19-1], represents the Chemical Abstracts Registry Number. The above-mentioned mixing partners are publicly known. When the active ingredients are listed in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are listed therein by the parenthetical identifier number shown above for the specific compound in this specification; for example, the compound "abamectin" is listed as identifier number (1). When a specific compound shown above in this specification is marked with "[CCN]", the compound in question is listed in the "Compendium of Pesticide Common Names" available on the Internet at [A. Wood; Compendium of Pesticide Common Names, Copyright 1995-2004]; for example, the compound "acetoprole" is listed at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0186] Most of the active ingredients listed herein above are listed by so-called "common names," and in each case, the appropriate "ISO nonproprietary name" or other "common name" is used. When the designation is not a "common name," the type of designation used instead for that particular compound is listed in parentheses, either an IUPAC name, IUPAC / Chemical Abstracts name, "chemical name," "traditional name," "compound name," or "development code" is used, or, if neither one of these nor a "common name" is used, an "synonym" is used. "CAS Reg. No." refers to the Chemical Abstracts Registry Number.

[0187] The mixing ratio of the active ingredient mixture of a compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2) or (I-A3), or one compound selected from the group consisting of the compounds shown in A-1 to A-23 or the compounds described in Table P (described later), is preferably 100:1 to 1:100, particularly 50:1 to 1:50, more particularly 20:1 to 1:20, even more particularly 10:1 to 1:10, and even more particularly 5:1 to 1:5. These mixing ratios are by weight.

[0188] The mixture can be used in a method for controlling pests, which method comprises applying a composition comprising the mixture to the pest or its environment, but excludes methods for surgical or therapeutic treatment of the human or animal body and diagnostic methods performed on the human or animal body.

[0189] Mixtures containing a compound selected from the group consisting of compounds of formula (I), (IA), (I-A1), (I-A2), or (I-A3), or a compound selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds shown in Table P (infra), and one or more of the active ingredients described above can be applied, for example, in the form of a single "ready-to-use" mixture, in a spray mixture consisting of a mixture of separate formulations of a single active ingredient, such as a "tank mix," or in a combination in which the single active ingredients are applied sequentially, i.e., one after the other, over a reasonably short period of time, such as a few hours or days. The order of application of a compound selected from the group consisting of compounds of formula (I), (IA), (I-A1), (I-A2), or (I-A3), or a compound selected from the group consisting of the compounds shown in Tables A-1 to A-23 or the compounds shown in Table P (infra), and the active ingredients described above, is not critical to the practice of the invention.

[0190] The compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity modifiers, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0191] The compositions according to the invention can be prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient, and in the presence of at least one auxiliaries, for example by intimately mixing and / or grinding the active ingredient together with the auxiliaries. These processes for preparing the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0192] Another aspect of the present invention relates to the use of a compound of formula (I) according to the present invention or a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein in a mixture with other fungicides or insecticides as mentioned above, on plants, useful plants such as crop plants, their propagation material such as seeds, harvested crops, for example harvested food crops, or non-living material, for controlling or preventing infestation by insects or phytopathogenic microorganisms, preferably fungal organisms.

[0193] A further aspect of the present invention relates to a method for controlling or preventing infestation of plants, for example useful plants such as crop plants, their propagation material, for example seeds, harvested crops, for example harvested food crops or non-living material, by phytopathogenic or spoilage microorganisms or organisms potentially harmful to humans, in particular fungal organisms, which method comprises applying as active ingredient a compound of formula (I) according to the invention or a preferred individual compound as defined herein to the plant, to parts of the plant or its habitat, its propagation material or any part of the non-living material.

[0194] Control or prevention means reducing infestation by insects or plant pathogenic or spoilage microorganisms or organisms potentially harmful to humans, especially fungal organisms, to a level that demonstrates improvement.

[0195] A preferred method for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, particularly fungal organisms or insects, involves the application of a compound of formula (I) according to the present invention or an agrochemical composition containing at least one compound of formula (I). The frequency and rate of application will vary depending on the risk of infestation by the corresponding pathogen or insect. However, the compound of formula (I) according to the present invention can also be introduced into the plant through the roots (systemic action) by drenching the plant habitat with a liquid formulation or by applying a solid form of the compound to the soil, for example, in the form of granules (soil application). In rice cultivation, such granules can be applied to flooded rice fields. The compound of formula (I) can also be applied to seeds (coating) by either immersing the seeds or tubers in a liquid formulation of the fungicide or coating them with a solid formulation.

[0196] Formulations, such as compositions comprising a compound of formula (I) according to the invention and, optionally, a solid or liquid auxiliary or a monomer for encapsulating the compound of formula (I), can be prepared in a known manner, typically by intimately mixing and / or grinding the compound with an extender, such as a solvent, a solid carrier and, optionally, a surface-active compound (surfactant).

[0197] Advantageous application rates are usually from 5g to 2kg of active ingredient (ai) per hectare (ha), preferably from 10g to 1kg ai / ha, most preferably from 20g to 600g ai / ha.When used as a seed drenching agent, convenient application rates are from 10mg to 1g of active substance per kg of seed.

[0198] As used herein, the term "g ai / ha" refers to a rate given in grams [g] of active ingredient [ai] per unit surface [ha]. The hectare (symbol ha) is a square measuring 100 m on a side (1 hm 2 ) or 10,000 square meters. The hectare is a commonly used metric unit of area.

[0199] When the combinations according to the invention are used as seed treatment, a rate of compound of formula (I) of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g per kg of seed, is generally sufficient.

[0200] Preferably, the compositions containing the compounds of formula (I) according to the invention are applied either preventively, ie before the onset of disease, or curatively, ie after the onset of disease.

[0201] The compositions of the present invention may be in any conventional form, for example in two-part form, dry seed treatment powder (DS), seed treatment emulsion (ES), seed treatment flowable (FS), seed treatment solution (LS), seed treatment water dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsifiable concentrate (EC), suspension concentrate (SC), suspoemulsion (SE), capsule suspension (CS), water dispersible granules (WG), emulsifiable granules (E), The composition may be used in the form of a water-in-oil emulsion (EO), oil-in-water emulsion (EW), microemulsion (ME), oil dispersion (OD), oil-flowable formulation (OF), oil-liquid formulation (OL), soluble concentrate (SL), ULV-suspension (SU), ULV-liquid (UL), technical concentrate (TK), dispersible concentrate (DC), wettable powder (WP) or any technically feasible formulation in combination with an agriculturally acceptable adjuvant.

[0202] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable inert ingredients (diluents, solvents, fillers, and optionally other ingredients, such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing auxiliary effects). If long-lasting efficacy is intended, conventional sustained-release formulations can also be used. In particular, formulations applied in the form of sprays, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents and dispersants, as well as other compounds that provide auxiliary effects, such as condensation products of formaldehyde with naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0203] The seed dressing formulation is applied to seeds in a manner known per se, using the combination of the present invention and diluents in a suitable seed dressing formulation form, for example, as an aqueous suspension or in the form of a dry powder that adheres well to seeds.Such seed dressing formulations are known in the art.The seed dressing formulation can contain a single active ingredient or a combination of active ingredients in an encapsulated form, for example, as a sustained-release capsule or microcapsule.

[0204] Typically, the formulations contain 0.01 to 90% by weight of active agent, 0 to 20% by weight of agriculturally acceptable surfactant, and 10 to 99.99% by weight of inactive substances and adjuvants for solid or liquid formulations, where the active agent consists of at least a compound of formula (I) according to the present invention, optionally together with other active agents, particularly microbicides or preservatives. Concentrate forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of active agent. The application form of the formulation may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of active agent. Commercially available products are preferably formulated as concentrates, but end users will typically use diluted formulations.

[0205] Commercially available products are preferably formulated as concentrates, although end users will typically use diluted formulations.

[0206] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing climatic conditions and other factors which depend on the method, time of application and the target crop. As a general guideline, the compounds may be applied at rates of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0207] A preferred formulation may have the following composition (% by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0208] Powder: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0209] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0210] Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0211] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0212] The present disclosure contemplates the use of any and all combinations of the embodiments disclosed herein.

[0213] The compounds according to the following Tables A-1 to A-23 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the present invention and show preferred compounds of formula (I). In any of the following Tables A-1 to A-23, the possible presence of one or more asymmetric carbon atoms in the compounds of formula (I) according to the present invention means that chiral isomeric forms, i.e., enantiomeric or diastereomeric forms, of the compounds can exist.

[0214] Table A: This table shows the substituent Z of the compounds of formula (IA) according to the invention 1 This paper discloses 32 definitions of the term. [ka] Z according to the compounds of formula (I) of the present invention 1 is defined below.

[0215] [Table 1]

[0216] Therefore, compounds in which the substituents of formula (IA) are specifically described are shown in the following Tables A-1 to A-23.

[0217] Table A-1: ​​This table shows the R 2 , R 4 , R 5 and R 6 is H and B 1 , B 2 and B 3 is CH and Z 1 and 36 compounds (A-1.01) to (A-1.36) of formula (IA) in which the substituents are as defined in Table A. For example, compound (A-1.01) has the following structure: [ka] It has.

[0218] Table A-2: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 , B 2 and B 3 is CH and Z 1 and 36 compounds (A-2.01) to (A-2.36) of formula (IA) in which the substituents are as defined in Table A. For example, compound (A-2.08) has the following structure: [ka] It has.

[0219] Table A-3: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 , B 2 and B 3 is CH and Z 1 and 36 compounds (A-3.01) to (A-3.36) of formula (IA) in which the substituents are as defined in Table A.

[0220] Table A-4: This table shows the R 2 , R 4 , R 5 and R 6 is H and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-4.01) to (A-4.36) of formula (IA), wherein the substituents are as defined in Table A.

[0221] Table A-5: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 and B 2 is CH and B 3is N and Z 1 and 36 compounds (A-5.01) to (A-5.36) of formula (IA), wherein the substituents are as defined in Table A. For example, compound (A-5.35) has the following structure: [ka] It has.

[0222] Table A-6: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-6.01) to (A-6.36) of formula (IA), wherein the substituents are as defined in Table A.

[0223] Table A-7: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-7.01) to (A-7.36) of formula (IA), wherein the substituents are as defined in Table A.

[0224] Table A-8: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 is CH and B 2 is C-Cl, and B 3 is N and Z 1 and 36 compounds (A-8.01) to (A-8.36) of formula (IA), wherein the substituents are as defined in Table A.

[0225] Table A-9: This table shows the R 4 , R5 and R 6 is H and R 2 is CH3 and B 1 is CH and B 2 is C-Br, and B 3 is N and Z 1 and 36 compounds (A-9.01) to (A-9.36) of formula (IA), wherein the substituents are as defined in Table A.

[0226] Table A-10: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 is CH and B 2 is C-CN, and B 3 is N and Z 1 and 36 compounds (A-10.01) to (A-10.36) of formula (IA), wherein the substituents are as defined in Table A.

[0227] Table A-11: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 is CH and B 2 is C-Cl, and B 3 is N and Z 1 and 36 compounds (A-11.01) to (A-11.36) of formula (IA), wherein the substituents are as defined in Table A.

[0228] Table A-12: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 is CH and B 2 is C-Br, and B 3 is N and Z 1 and 36 compounds (A-12.01) to (A-12.36) of formula (IA), wherein the substituents are as defined in Table A.

[0229] Table A-13: This table shows the R 4 , R 5 and R 6 is H and R 2 is Cl and B 1 is CH and B 2 is C-CN, and B 3 is N and Z 1 and 36 compounds (A-13.01) to (A-13.36) of formula (IA), wherein the substituents are as defined in Table A.

[0230] Table A-14: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 is CH and B 2 is C-CH3, and B 3 is N and Z 1 and 36 compounds (A-14.01) to (A-14.36) of formula (IA), wherein the substituents are as defined in Table A.

[0231] Table A-15: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 is C-CH3, and B 2 is C-Cl, and B 3 is N and Z 1 and 36 compounds (A-15.01) to (A-15.36) of formula (IA), wherein the substituents are as defined in Table A.

[0232] Table A-16: This table shows the R 2 , R 5 and R 6 is H and R 4 is CH3 and B 1 and B 2 is CH and B 3 is N and Z 1and 36 compounds (A-16.01) to (A-16.36) of formula (IA), wherein the substituents are as defined in Table A.

[0233] Table A-17: This table shows the R 5 and R 6 is H and R 2 and R 4 is CH3 and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-17.01) to (A-17.36) of formula (IA), wherein the substituents are as defined in Table A.

[0234] Table A-18: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 1 is CH and B 2 and B 3 is N and Z 1 and 36 compounds (A-18.01) to (A-18.36) of formula (IA), wherein the substituents are as defined in Table A.

[0235] Table A-19: This table shows the R 4 , R 5 and R 6 is H and R 2 is CH3 and B 2 is CH and B 1 and B 3 is N and Z 1 and 36 compounds (A-19.01) to (A-19.36) of formula (IA), wherein the substituents are as defined in Table A.

[0236] Table A-20: This table is for R 4 , R 5 and R 6 is H and R 2 is CH3 and B 2 , B 1 and B 3is N and Z 1 and 36 compounds (A-20.01) to (A-20.36) of formula (IA), wherein the substituents are as defined in Table A. For example, compound (A-20.09) has the following structure: [ka] It has.

[0237] Table A-21: This table shows the R 4 and R 5 is H and R 6 is C-Cl and R 2 is CH3 and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-21.01) to (A-21.36) of formula (IA), wherein the substituents are as defined in Table A.

[0238] Table A-22: This table shows the R 4 and R 5 is H and R 6 is C-Br and R 2 is CH3 and B 1 and B 2 is CH and B 3 is N and Z 1 and 36 compounds (A-22.01) to (A-22.36) of formula (IA), wherein the substituents are as defined in Table A. For example, compound (A-22.04) has the following structure: [ka] It has.

[0239] Table A-23: This table shows the R 4 and R 5 is H and R 6 is C-CN and R 2 is CH3 and B 1 and B 2 is CH and B 3 is N and Z 1and 36 compounds (A-23.01) to (A-23.36) of formula (IA), wherein the substituents are as defined in Table A. [Example]

[0240] The examples presented below serve to illustrate the invention and are not intended to limit it in any way.

[0241] The compounds of the present invention can be distinguished from known compounds by exhibiting higher efficacy at lower application rates, which can be confirmed by one skilled in the art using the experimental procedures outlined in the Examples, using lower application rates, such as 60 ppm, 20 ppm or 2 ppm, if necessary.

[0242] The compounds of formula (I) may have any number of advantages, such as advantageous levels of biological activity to protect plants from diseases caused by fungi or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, advantageous spectrum of activity, improved safety profile (including improved crop tolerance), improved physicochemical properties or improved biodegradability), among others.

[0243] Throughout this specification, temperatures are given in degrees Celsius and "mp" means melting point. LC / MS means liquid chromatography mass spectrometry. A description of the instrument and method follows.

[0244] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer. Chemical shifts are expressed as TMS( 1 H) and CFCl3 ( 19 F) are expressed in ppm relative to a standard. Spectra were measured in deuterated solvents as specified. Compounds were characterized using one of the LC-MS methods listed below. Characteristic LC-MS values ​​obtained for each compound include retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - is.

[0245] LC-MS method LC-MS Method A: Spectra were recorded using: a mass spectrometer (SQD, SQDII or QDA single quadrupole mass spectrometer) from Waters Corporation equipped with an electrospray source (polarity: positive and negative ions): capillary voltage: 0.8-3.00 kV, cone voltage: 5-30 V, source temperature: 120-150 °C, desolvation temperature: 350-600 °C, cone gas flow: 50-150 l / h, desolvation gas flow: 650-1000 l / h, mass scan range: 100-900 Da and an Acquity UPLC from Waters Corporation: binary pump, heated column compartment, diode array detector and ELSD, column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210-400, run time: 1.5 min; solvent: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; flow rate (ml / min) 0.85, gradient: 10% B isocratic (0.2 min), then 10-100% B (1.0 min), 100% B isocratic (0.2 min), 100-10% B (0.05 min), 10% B isocratic (0.05 min).

[0246] LC-MS Method B: Spectra were recorded using an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporations equipped with an electrospray source (polarity: positive and negative ions, capillary voltage: 3.0 kV, cone voltage: 30 V, extractor voltage: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass scan range: 140-800 Da) and an ACQUITY UPLC from Waters Corporations equipped with a solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210-400, solvent gradient: A = water / methanol. 9:1 ​​+ 0.1% formic acid, B = acetonitrile + 0.1% formic acid, gradient: 0-100% B (2.5 min); flow rate (ml / min) 0.75.

[0247] LC-MS C method: Spectra were recorded using a mass spectrometer (SQD2 or QDA single quadrupole mass spectrometer) from Waters equipped with an electrospray source (polarity: reversible polarity, capillary voltage: 0.8-3.00 kV, cone voltage range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 1000 L / h, mass scan range: 110-850 Da) and an Acquity UPLC from Waters equipped with a quaternary solvent manager, heated column compartment, diode array detector, column: Acquity UPLC HSS T3 C18, 1.8 μm, 30 × 2.1 mm, temperature: 40 °C, DAD wavelength range (nm): 200-400, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 10%B (0 min); 10-50%B (0-0.2 min); 50-100%B (0.2-0.6 min); 100%B (0.6-1.3 min); 100-10%B (1.3-1.4 min); 10%B (1.4-1.6 min); Flow rate (mL / min) 0.6.

[0248] LC-MS D method: Spectra were recorded using a mass spectrometer (6410 Triple Quadrupole Mass Spectrometer) from Agilent Technologies equipped with an electrospray source (polarity: positive or negative ion, MS2 scan, capillary voltage: 4.00 kV, fragmentor voltage: 100 V, desolvation temperature: 350 °C, gas flow rate: 11 L / min, nebulizer gas: 45 psi, mass scan range: 110-1000 Da) and a 1200 Series HPLC from Agilent equipped with a quaternary pump, heated column compartment and VWD detector, column: KINETEX EVO C18, 2.6 μm, 50 × 4.6 mm, temperature: 40 °C, VWD detector wavelength: 254 nm, solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile 0.1% HCOOH: Gradient: 10% B, 90% A (0 min); 100% B (0.9-1.8 min); 100-10% B (1.8-2.2 min); 10% B (2.2-2.5 min); flow rate (mL / min) 1.8.

[0249] LC-MS E method: Spectra were recorded using an ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) from Waters Corporations equipped with an electrospray source (polarity: positive or negative ion, capillary voltage: 3.0 kV, cone voltage: 30 V, extractor voltage: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass scan range: 140-800 Da) and an ACQUITY UPLC from Waters Corporations equipped with a solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210-400, solvent gradient: A = water / methanol. 9:1 ​​+ 0.1% formic acid, B = acetonitrile + 0.1% formic acid, gradient: 0-100% B (3.0 min); flow rate (ml / min) 0.75.

[0250] Formulation Examples

[0251] [Table 2]

[0252] This combination is thoroughly mixed with an adjuvant and the mixture is thoroughly ground in a suitable grinder to give a wettable powder which can be diluted with water to give a suspension of the desired concentration.

[0253] [Table 3]

[0254] This combination is thoroughly mixed with an adjuvant, and the mixture is thoroughly ground in a suitable grinder to obtain a dust that can be used directly for seed treatment.

[0255] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (ethylene oxide 4-5 moles) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 moles) 4% Cyclohexanone 30% Xylene mixture 50%

[0256] This concentrate can be diluted with water to obtain an emulsion of the required dilution that can be used for plant protection.

[0257] [Table 4]

[0258] This combination is mixed with a carrier and the mixture is ground in a suitable grinder to give a ready-to-use dust, which can also be used as a dry seed dressing.

[0259] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0260] This combination is mixed with the adjuvants and ground, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0261] Coated granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0262] This combination is finely ground and applied uniformly in a mixer to kaolin moistened with polyethylene glycol, thus obtaining non-dusting coated granules.

[0263] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (ethylene oxide 15 moles) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (75% emulsion in water) 1% water 32%

[0264] This combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect them from microbial infestation.

[0265] Flowable seed treatment Active ingredient 40% Propylene glycol 5% Butanol PO / EO copolymer 2% Tristyrenephenol with 10-20 moles of EO 2% 1,2-Benzisothiazolin-3-one (20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (75% emulsion in water) 0.2% Water 45.3%

[0266] This combination is pulverized and intimately mixed with adjuvants to form a suspension concentrate, which can be diluted with water to obtain a suspension of the desired dilution, allowing growing plants, as well as plant propagation material, to be treated by spraying, pouring, or dipping to protect them from microbial infestation.

[0267] Sustained-release capsule suspension 28 parts of this combination are mixed with 2 parts aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is reached. To this emulsion, a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added. The mixture is stirred until polymerization is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. This capsule suspension formulation contains 28% active ingredient. The median capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension using equipment suitable for that purpose.

[0268] Formulation types include emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), oil dispersions (OD), oil-flowable formulations (OF), oil-liquid formulations (OL), soluble concentrates (SL), ULV-suspensions (SU), ULV-liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), water-soluble granules (SG) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0269] Shorthand: CDCl3 deuterated chloroform CO Carbon monoxide DABCO 1,4-diazabicyclo[2.2.2]octane, also known as triethylenediamine or TEDA DCC dicyclohexylcarbodiimide DIPEA Diisopropylethylamine (N,N-diisopropylethylamine) DMA Dimethylacetamide DMF Dimethylformamide DMSO dimethyl sulfoxide DMSO-d6 Deuterated dimethyl sulfoxide EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Et3N Triethylamine EtOAc ethyl acetate HATU 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate HCl Hydrochloric acid hr / hrs time LC-MS Liquid Chromatography Mass Spectrometry (LC-MS or LCMS) ppm parts per million rh relative humidity rt room temperature Rt retention time ssp. subspecies TBME Methyl tert-butyl ether or tert-butyl methyl ether

[0270] Preparation Examples The compounds of formula (I) according to the invention can be prepared using the synthetic techniques described above and below.

[0271] Example P1: Synthesis of 4-(1-methylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide (compound P-3, Table P) [ka] Step A: Preparation of 4-(1-methylpyrazol-4-yl)quinoline [ka] A 250 mL flask was charged with 4-bromoquinoline (2.50 g, 12.0 mmol [CAS 3964-04-3]), THF (36 mL), water (6 mL), cesium carbonate (15.7 g, 48.1 mmol), and (1-methylpyrazol-4-yl)boronic acid (2.12 g, 16.8 mmol) at room temperature under an argon atmosphere. The resulting reaction mixture was again purged with argon, and Pd(dppf)Cl2·CHCl2 (0.496 mg, 0.601 mmol) was added. The reaction mixture was stirred at 95 °C for 2 hours and 30 minutes. After this time, additional Pd(dppf)Cl2·CHCl2 (0.496 mg, 0.601 mmol) and (1-methylpyrazol-4-yl)boronic acid (2.12 g, 16.8 mmol) were added, and the resulting reaction mixture was stirred at 95 °C for an additional 2 hours. The reaction mixture was cooled to room temperature and diluted with saturated aqueous NH4Cl and EtOAc. The aqueous layer was separated and back-extracted with EtOAc, and the organic extracts were combined, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to give 4-(1-methylpyrazol-4-yl)quinoline. LC-MS: 210[M+H], Rt: 0.27-30 minutes (A method) 1 H NMR(400MHz,CDCl3)δ ppm 4.05-4.10(m,3H)7.34-7.39(m,1H)7.55-7.62(m,1H)7.73-7.79(m,2H)7.83-7.88(m,1H)8.15-8.25(m,2H)8.85-8.97(m,1H)

[0272] Step B: Preparation of 4-(1-methylpyrazol-4-yl)-1-oxide-quinolin-1-ium [ka] A 25 mL flask was charged with 4-(1-methylpyrazol-4-yl)quinoline (1.37 g, 6.55 mmol) and dichloromethane (32 mL), and the resulting solution was treated with 3-chlorobenzenecarboperoxoic acid (3.39 g, 19.6 mmol) in small portions at room temperature under an argon atmosphere. The resulting reaction mixture was stirred at room temperature for 1 hour and then quenched with saturated NaSO solution. The resulting reaction mixture was stirred for 30 minutes after quenching and then diluted with DCM and saturated aqueous NaHCO solution. The organic phase was separated and washed twice with saturated NaHCO solution, once with water, and once with saturated brine. A peroxide test still showed very small amounts of peroxide, so the dichloromethane solution was diluted with saturated NaSO solution and stirred at room temperature over the weekend. The organic phase was separated, and the aqueous phase was back-extracted with dichloromethane. The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure to give pure 4-(1-methylpyrazol-4-yl)-1-oxide-quinolin-1-ium. LC-MS: 226[M+H], Rt: 0.52 min (A method) 1 H NMR(400MHz,CDCl3)δ ppm 8.82-8.99(m,1H)8.58(br s,1H)8.20(br d,J=8.0Hz,1H)7.65-7.85(m,4H)7.28(s,1H)4.03-4.11(m,3H).

[0273] Step C: Preparation of 2-chloro-4-(1-methylpyrazol-4-yl)quinoline [ka] A solution of 4-(1-methylpyrazol-4-yl)-1-oxide-quinolin-1-ium (1.05 g, 4.66 mmol) in phosphoryl chloride (9 mL) was mixed, and the resulting black solution was stirred at 60 °C for 45 minutes. The phosphoryl chloride was removed by concentration under vacuum, and the resulting residue was diluted with EtOAc and water. The solution was neutralized by slowly adding saturated aqueous NaHCO3. The EtOAc was removed, and the aqueous phase was back-extracted with EtOAc. The combined organic phases were washed once with saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give 2-chloro-4-(1-methylpyrazol-4-yl)quinoline. LC-MS: 244[M+H], Rt: 0.86 min (A method) 1H NMR(400MHz,CDCl3)δ ppm 8.18(dd,J=8.4,1.1Hz,1H)8.09-8.14(m,1H)7.86(s,1H)7.75-7.82(m,2H)7.60(ddd,J=8.4,7.0,1.3Hz,1H)7.38(s,1H)4.08(s,3H)

[0274] Step D: Preparation of methyl 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylic acid [ka] A solution of 2-chloro-4-(1-methylpyrazol-4-yl)quinoline (300 mg, 1.23 mmol) and triethylamine (0.347 mL, 2.46 mmol) in methanol (4.5 mL) was treated with Pd(dppf)Cl₂·CHCl₂ (0.102 mg, 0.1231 mmol), and the reaction mixture was purged with a stream of argon for 5 minutes. The reaction mixture was stirred overnight at 80 °C under 10 bar of carbon monoxide (CO) in an autoclave. The reaction mixture was cooled, purged with argon, evaporated, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to give methyl 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylate. LC-MS:268[M+H], Rt:0.75min (A method) 1H NMR(400MHz,CDCl3)δ ppm 4.08-4.10(m,3H)4.11-4.14(m,3H)7.65-7.72(m,1H)7.79-7.87(m,2H) 7.89-7.93(m,1H)8.16-8.21(m,1H)8.25-8.32(m,1H)8.35-8.41(m,1H)

[0275] Step E: Preparation of lithium 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylate [ka] A solution of methyl 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylate (226 mg, 0.845 mmol) in 3:1 THF / HO (8 mL) was treated with LiOH HO (39.82 mg, 0.930 mmol), and the resulting reaction mixture was stirred at room temperature for 1 h. The title compound was obtained by removing the solvent in vacuo. LC-MS: 254[M+H], Rt: 0.49 min (free acid) (method A) 1 H NMR(400MHz,DMSO-d6)δ ppm 3.99(s,3H)7.61-7.68(m,1H)7.76-7.83(m,1H)7.94-7.97(m,1H)7.99-8.04(m,1H)8.11-8.16(m,1H)8.26-8.32(m,1H)8.36-8.40(m,1H)

[0276] Step F: Synthesis of 4-(1-methylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-3, Table P) Step F - Option A: A sample of 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylic acid (114 mg, 0.450 mmol) was dissolved in EtOAc (1 mL) and treated with pentan-1-amine (0.041 mg, 0.472 mmol), T3P (0.670 mL, 1.125 mmol), and diisopropylamine (0.236 mL, 1.350 mmol) at room temperature under argon. The resulting reaction mixture was stirred at room temperature for 30 minutes and then diluted with water, saturated NaHCO3, and EtOAc. The organic layer was separated, the aqueous phase was back-extracted with EtOAc, and the combined organic phases were washed once with saturated brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified once by normal-phase chromatography and once by reverse-phase chromatography to give 4-(1-methylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide as a white solid. LC-MS: 323[M+H], Rt: 1.04 min (A method) 1 H NMR(400MHz,CDCl3)δ ppm 0.90-1.02(m,3H)1.38-1.51(m,4H)1.69-1.81(m,2H)3.52-3.63(m,2H)4.04-4.13(m,3H) 7.60-7.69(m,1H)7.76-7.86(m,2H)7.89-7.96(m,1H)8.14-8.20(m,1H)8.26-8.39(m,3H)

[0277] Step F - Option B: The autoclave was flushed with argon and Pd(dppp)Cl2 (0.063 g, 0.103 mmol) was added followed by a suspension of 2-chloro-4-(1-methylpyrazol-4-yl)quinoline (0.500 g, 2.05 mmol), pentan-1-amine (0.268 g, 3.08 mmol) and triethylamine (0.715 mL, 5.13 mmol) in THF (10 mL) and the reaction mixture was heated at 100 °C under 10 bar of CO (carbon monoxide) pressure overnight. Additional Pd(dppp)Cl (0.063 g, 0.103 mmol), pentan-1-amine (0.268 g, 3.08 mmol), and triethylamine (0.715 mL, 5.13 mmol) were added, and the resulting reaction mixture was heated at 100° C. under a CO atmosphere (10 bar) for an additional 2 days. LCMS analysis then indicated complete conversion to the desired compound. The reaction mixture was adsorbed directly onto Isolute®, the solvent was removed in vacuo, and the resulting residue was purified by chromatography on silica gel to give 4-(1-methylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide.

[0278] Example P2: Preparation of N-[(2,4-difluorophenyl)methyl]-4-(1-methylpyrazol-4-yl)quinoline-2-carboxamide (compound P-1, Table P) [ka] A 25 mL flask was charged with 4-(1-methylpyrazol-4-yl)quinoline-2-carboxylic acid (42 mg, 0.162 mmol), and then 0.65 mL of EtOAc and one drop of DMF were added. Then, 0.035 mL of oxalyl chloride (0.405 mmol) was slowly added at room temperature under an argon atmosphere. After 30 minutes, the reaction mixture was concentrated under reduced pressure to give 4-(1-methylpyrazol-4-yl)quinoline-2-carbonyl chloride (0.044 g, 0.1619 mmol). To a mixture of the above 4-(1-methylpyrazol-4-yl)quinoline-2-carbonyl chloride (0.026 g, 0.09569 mmol) in CHCN (0.78 mL) under an argon atmosphere, (2,4-difluorophenyl)methanamine (0.013 g, 0.095 mmol) and potassium iodide (0.008 mg, 0.047 mmol) were added. The reaction mixture was stirred at 60 °C for 1 h, cooled to room temperature, diluted with water and EtOAc, and saturated aqueous NaHCO was added. The organic layer was removed, and the aqueous phase was back-extracted with EtOAc. The combined organic layers were washed with saturated brine, dried over NaSO, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to give N-[(2,4-difluorophenyl)methyl]-4-(1-methylpyrazol-4-yl)quinoline-2-carboxamide. LC-MS:379[M+H], Rt:1.01min (A method) 1 H NMR(400MHz,CDCl3)δ ppm 4.04-4.12(m,3H)4.74-4.83(m,2H)6.83-6.93(m,2H)7.45-7.53(m,1H)7.63-7.69(m,1H) 7.77-7.83(m,2H)7.90-7.95(m,1H)8.14-8.23(m,1H)8.26-8.34(m,2H)8.64-8.86(m,1H)

[0279] Example P3: Synthesis of 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide (compound P-2, Table P) [ka] Step A: Preparation of methyl 1-oxidoquinolin-1-ium-2-carboxylate [ka] To a solution of methyl quinoline-2-carboxylate (CAS 19575-07-6) (0.670 g, 3.579 mmol [CAS 19575-07-6]) in trifluoromethylbenzene (10 mL) at 0°C, 3-chlorobenzenecarboperoxoic acid (2.37 g, 8.947 mmol, 65% by mass) was added at 0°C. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was quenched with 2N aqueous NaOH and water and extracted with EtOAc. The combined organic layer was washed with saturated brine, dried over Na2SO4, and concentrated under reduced pressure to give methyl 1-oxidequinolin-1-ium-2-carboxylate. LC-MS:204[M+H], Rt:0.46min (B method)

[0280] Step B: Preparation of methyl 4-chloroquinoline-2-carboxylate [ka] A sample of methyl 1-oxidoquinolin-1-ium-2-carboxylate (900 mg, 3.100 mmol) was dissolved in phosphorus(V) oxychloride (18 mL). The resulting reaction mixture was heated to 80 °C and stirred at this temperature for 3 h. The reaction mixture was cooled to room temperature and added dropwise to water at room temperature with stirring over 20 min, followed by quenching with ice-cold saturated NaHCO solution. The reaction mixture was extracted with EtOAc, and the combined organic layers were dried over NaSO and concentrated under reduced pressure. The crude product was purified by CombiFlash® using 10-20% EtOAc in cyclohexane to give methyl 4-chloroquinoline-2-carboxylate. LC-MS:222[M+H], Rt:1.07min (C method) 1H NMR(400MHz,CDCl3-d)δ ppm 8.33-8.38(m,1H)8.28-8.32(m,2H)8.07-8.11(m,1H)7.97-8.02(m,1H)7.84-7.91(m, 1H)7.76-7.76(m,1H)7.75-7.81(m,1H)7.56-7.63(m,1H)7.40-7.48(m,1H)4.11(s,3H)

[0281] Step C: Preparation of methyl 4-(1,5-dimethylpyrazol-4-yl)quinoline-2-carboxylate [ka] A solution of methyl 4-chloroquinoline-2-carboxylate (0.197 mg, 0.445 mmol) and 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole (100 mg, 0.4052 mmol) in 2-methyltetrahydrofuran (1.6 mL) was treated with potassium phosphate (0.263 g, 1.216 mmol), and the resulting reaction mixture was degassed with nitrogen. A sample of [(di(1-adamantyl)-n-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) mesylate, [(di(1-adamantyl)-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate (cataCXium® A PdG®) (0.031 g, 0.0405 mmol [1651823-59-4]) was added (brown suspension), and the reaction mixture was stirred at 80 °C for 1 h. The reaction mixture was poured into water and then extracted with EtOAc (3 × 20 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by combi flash chromatography on silica gel to give methyl 4-(1,5-dimethylpyrazol-4-yl)quinoline-2-carboxylate. LC-MS: 282[M+H], Rt: 0.98 min (C method) 1H NMR(400MHz,CDCl3-d)δ ppm 8.27(d,J=8.68Hz,1H)7.96(s,1H)7.85-7.95(m,1H)7.66-7.76(m,1H)7.57( s,2H)7.50-7.55(m,1H)7.20(s,1H)3.86(s,3H)3.65-3.71(m,3H)2.33(s,3H)

[0282] Step D: Synthesis of 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide (Compound P-2, Table P) A MW vial was charged with methyl 4-(1,5-dimethylpyrazol-4-yl)quinoline-2-carboxylate (70.0 mg, 0.174 mmol) and pentan-1-amine (0.020 mL, 0.174 mmol). The reaction mixture was then microwaved at 100 °C for 1 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to give the crude product. The crude product was adsorbed onto Celite and purified by RP chromatography eluting with 50-65% water in CHCN to give 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-quinoline-2-carboxamide. LC-MS (Agilent): 337[M+H], Rt: 1.61 min (D method) 1 H NMR(400MHz,CDCl3-d)δ ppm 8.29-8.37(m,1H)8.12-8.19(m,2H)7.99-8.06(m,1H)7.75-7.82(m,1H)7.64-7.68(m,1H)7.55-7.63(m,1H)3.90- 3.99(m,3H)3.55(q,J=6.77Hz,2H)2.30(s,3H)1.73(quin,J=7.24Hz,3H)1.35-1.51(m,5H)0.94(t,J=7.03Hz,3H)

[0283] General synthetic procedure for library synthesis: 4-(1,5-dimethylpyrazol-4-yl)quinoline-2-carboxylic acid (prepared as described in Example P-1, see above), 8-bromo-4-(1,5-dimethylpyrazol-4-yl)quinoline-2-carboxylic acid (prepared similarly to the example described in Example P-1), and 4-(1,5-dimethylpyrazol-4-yl)-8-fluoro-quinoline-2-carboxylic acid (CAS [2866323-20-6]) (2 mmol / 0.04 mmol planned reaction) were dissolved in 10 mL of DMA (dimethylacetamide) in a 20 mL amber glass bottle. After gentle stirring, 200 μL of each scaffold was added to each reaction well of a 1.5 mL deep well plate (DWP). One DWP was used per scaffold. DIPEA (N,N-diisopropylethylamine, Hunig's base) (6 eq., 0.24 mmol, 40 μL) was added to each reaction well of each DWP using a multi-pipette. Each amine building block (6 eq., 0.024 mmol) was weighed into a 4 mL test tube and dissolved in 0.9 mL of DMA. Using a Tecan Robot, 0.3 mL aliquots were dispensed into each corresponding reaction well of each DWP (2 eq., 0.08 mmol, three times for each building block). HATU (5.88 mmol total, 0.08 mmol per planned reaction, 4.517 g) was weighed into a 100 mL flask and dissolved in 73.5 mL of DMA. 0.5 mL aliquots were dispensed into each reaction well of each DWP. The DWP was sealed and heated in a 60 °C oven with vigorous shaking for 8 hours. Reaction monitoring was performed by diluting 20 μL of each DWP reaction mixture with acetonitrile (800 μL). Analysis by UPLC-MS generally indicated excellent formation of the desired product. The reaction mixture was mixed with MeOH (200 μL), transferred to a Nunc 96-deep-well plate, and purified by reverse-phase preparative HPLC. 50 μL of collected fractions were diluted with 100 μL of acetonitrile and analyzed by UPLC. The fraction solvent was removed from the samples using a Genevac evaporator. A Tecan robot performed pooling and reformatting steps, and the final product was placed in a final destination container. Final product quality control was performed by concentrating the product by evaporation (5 μL aliquot, diluted with 100 μL of acetonitrile).The predicted mass was confirmed by UPLC-MS (Method B). Compounds that passed QC were sent for biological evaluation.

[0284] Further examples of compounds of formula (I) that have been synthesized are shown in Table P.

[0285] [Table 5-1]

[0286] [Table 5-2]

[0287] [Table 5-3]

[0288] [Table 5-4]

[0289] [Table 5-5]

[0290] [Table 5-6]

[0291] [Table 5-7]

[0292] [Table 5-8]

[0293] [Table 5-9]

[0294] Table 5-10

[0295] Table 5-11

[0296] Table 5-12

[0297] Table 5-13

[0298] Table 5-14

[0299] Table 5-15

[0300] Table 5-16

[0301] Table 5-17

[0302] Table 5-18

[0303] Table 5-19

[0304] Table 5-20

[0305] Table 5-21

[0306] Table 5-22

[0307] Table 5-23

[0308] Table 5-24

[0309] Table 5-25

[0310] Table 5-26

[0311] Table 5-27

[0312] Table 5-28

[0313] Table 5-29

[0314] [Table 5-30]

[0315] Biological Examples Example B1: Alternaria solani / Tomato / Leaf disc (Tomato ring spot) Leaf discs of Baby tomato varieties were placed on agar medium in a multiwell plate (24-well type) and sprayed with formulated test compounds diluted in water. Two days after application, the leaf discs were inoculated with a fungal spore suspension. The inoculated leaf discs were incubated in a constant temperature room at 23°C / 21°C (day / night) and 80% rh under a 12 / 12 h photoperiod (light / dark). When the disease damage on the untreated leaf discs reached an appropriate level (5-7 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0316] The following compounds, at 200 ppm, provided at least 80% control of Alternaria solani compared to untreated controls under the same widespread disease conditions: P-2, P-9, P-11, P-14, P-16, P-18, P-21, P-22, P-23, P-24, P-25, P-26, P-29, P-30, P-38, P-41, P-44, P- 46, P-47, P-48, P-49, P-50, P-51, P-52, P-53, P-54, P-56, P-57, P-59, P-60, P-62, P-63, P-64, P-67, P- 68, P-69, P-70, P-71, P-74, P-75, P-77, P-81, P-83, P-85, P-86, P-89, P-91, P-92, P-93, P-94, P-95, P- 97, P-98, P-99, P-100, P-102, P-105, P-106, P-107, P-110, P-113, P-116, P-117, P-118, P-120, P-122, P -124, P-125, P-127, P-128, P-131, P-133, P-141, P-142, P-144, P-145, P-146, P-148, P-149, P-150, P- 151, P-152, P-155, P-156, P-158, P-159, P-161, P-162, P-163, P-164, P-165, P-166, P-167, P-168, P-17 0, P-172, P-178, P-181, P-184, P-185, P-189, P-194, P-197, P-198, P-203, P-204, P-218, P-229, P-230 , P-231, P-232, P-235, P-236, P-237, P-240, P-241, P-242, P-244, P-245, P-247, P-248, P-250 and P-256.

[0317] Example B2: Botryotinia fuckeliana (Botrytis cinerea) / liquid culture (gray mold) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium). A solution of the test compound (DMSO) is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 3-4 days after application.

[0318] The following compounds, at 20 ppm, provided at least 80% control of Botryotinia fuckeliana compared to untreated controls under the same widespread disease conditions: P-2, P-6, P-9, P-11, P-13, P-14, P-16, P-17, P-18, P-19, P-21, P-22, P-23, P-24, P-25, P -26, P-29, P-30, P-31, P-32, P-34, P-37, P-38, P-40, P-46, P-48, P-54, P-56, P-57, P-59, P-60, P-62, P-64, P-65, P-68, P-69, P-72, P-78, P-83, P-85, P-91, P-92, P-94, P-95, P-9 7, P-98, P-100, P-102, P-106, P-107, P-110, P-113, P-117, P-118, P-119, P-120, P-121, P -122, P-124, P-125, P-127, P-128, P-146, P-148, P-149, P-150, P-151, P-152, P-155, P- 156, P-158, P-161, P-162, P-164, P-166, P-167, P-168, P-176, P-178, P-181, P-184, P-18 5, P-191, P-193, P-194, P-195, P-197, P-214, P-219, P-223, P-236, P-237, P-240, P-241 , P-242, P-244, P-245, P-246, P-247, P-248, P-249, P-250, P-251, P-253, P-254 and P-256.

[0319] Example B3: Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (anthrax) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A (DMSO) solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is measured photometrically 3-4 days after application.

[0320] The following compounds, at 20 ppm, provided at least 80% control of Glomerella lagenarium compared to untreated controls under the same widespread disease conditions: P-2, P-3, P-6, P-9, P-10, P-11, P-12, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-20, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-30, P-31, P-32, P-33, P-34, P-37, P-40, P-41, P-43, P-44, P-45, P-46, P-47, P-48, P-49, P-50, P-51, P-52, P-53, P-54, P-55, P-56, P-57, P-59, P-60, P-61, P-62, P-63, P-64, P-68, P-69, P-70, P-71, P-72, P-73, P-74, P-77, P-78, P-81, P-82, P-83, P-84, P-85, P-86, P-87, P-88, P-89, P-90, P-91, P-92, P-93, P-94, P-95, P-97, P-98, P-99, P-100, P-101, P-102, P-106, P-107, P-108, P-109, P-110, P-113, P-117, P-118, P-119, P-120, P-121, P-122, P-124, P-125, P-128, P-148, P-149, P-150, P-152, P-158, P-159, P-161, P-162, P-163, P-164, P-167, P-168, P-171, P-173, P-176, P-178, P-181, P-182, P-184, P-185, P-189, P-191, P-193, P-194, P-195, P-197, P-198, P-203, P-204, P-214, P-218, P-219, P-223, P-224, P-231, P-236, P-237, P-240, P-241, P-242, P-244, P-245, P-246, P-247, P-248, P-250, P-251, P-253 and P-254.

[0321] Example B4: Blumeria graminis f.sp.tritici (Erysiphe graminis f.sp.tritici) / Wheat / Leaf Disk (Preventive) (Wheat Powdery Mildew) Wheat leaf segments of the Kanzler variety were placed on agar medium in a multiwell plate (24-well type) and sprayed with formulated test compounds diluted in water. One day after application, powdery mildew-infected plants were inoculated onto the leaf discs by shaking them over the test plates. The inoculated leaf discs were incubated in a constant temperature room at 20°C and 60% rh under a 24-h dark period followed by a 12-h light / 12-h dark photoperiod. When the disease damage on untreated control leaf segments reached an appropriate level (6-8 days after application), the activity of the compounds was evaluated as the disease control rate compared to the untreated control.

[0322] The following compounds, at 200 ppm, provided at least 80% control of Blumeria graminis f.sp. tritici compared to untreated controls under the same widespread disease conditions: P-2, P-6, P-9, P-18, P-21, P-22, P-23, P-24, P-25, P-26, P-29, P-32, P-38, P-44, P-56, P-57, P-59, P-78, P-8 1, P-91, P-92, P-94, P-95, P-97, P-98, P-99, P-100, P-118, P-120, P-124, P-125, P-127, P-128, P-142, P-144, P-146, P-148, P-149, P-150, P-151, P-152, P-155, P-156, P-158, P-161, P-162, P-163, P-164, P-165, P-167, P-173, P-178, P-181, P-230, P-232, P-240, P-241, P-242, P-244, P-245, P-247, P-248, P-249, P-250 and P-251.

[0323] Example B5: Fusarium culmorum / liquid culture (fusarium head blight) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A DMSO solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 3-4 days after application.

[0324] The following compounds, at 20 ppm, provided at least 80% control of Fusarium culmorum compared to untreated controls under the same widespread disease conditions: P-2, P-3, P-4, P-6, P-9, P-11, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-29, P-30, P-31, P-32, P-37, P-38, P-41, P-46, P-48, P-49, P-50, P-52, P-54, P-56, P-57, P-59, P-60, P-63, P-64, P-68, P-69, P-74, P-78, P-81, P-83, P-85, P-86, P-88, P-89, P-90, P-91, P-92, P-94, P-95, P-97, P-98, P-99, P-100, P-101, P-102, P-106, P-107, P-113, P-116, P-117, P-118, P-119, P-120, P-121, P-122, P-124, P-125, P-127, P-128, P-146, P-148, P-149, P-150, P-151, P-152, P-155, P-156, P-158, P-161, P-162, P-163, P-164, P-165, P-167, P-168, P-170, P-171, P-173, P-174, P-176, P-178, P-181, P-182, P-184, P-185, P-189, P-191, P-193, P-194, P-195, P-197, P-198, P-200, P-203, P-204, P-214, P-218, P-219, P-221, P-223, P-224, P-235, P-236, P-237, P-240, P-241, P-242, P-244, P-245, P-247, P-248, P-249, P-250, P-251, P-253 and P-256.

[0325] Example B6: Fusarium culmorum / Wheat / Spikelet (Preventive) (Scab) Spikelets of Monsun wheat are placed on agar medium in a multiwell plate (24-well type) and sprayed with a formulated test compound diluted with water. One day after application, the spikelets are inoculated with a fungal spore suspension. The inoculated spikelets are incubated in a constant temperature room at 20°C and 60% rh under a photoperiod of 72 hours of semi-darkness followed by 12 hours of light and 12 hours of darkness. When the disease damage on untreated control spikelets reaches an appropriate level (6 to 8 days after application), the activity of the compound is evaluated as the disease control rate compared to the untreated control.

[0326] The following compounds, at 200 ppm, provided at least 80% control of Fusarium culmorum compared to untreated controls under the same widespread disease conditions: P-6, P-17, P-18, P-21, P-22, P-23, P-25, P-26, P-29, P-56, P-78, P-83, P-9 4, P-95, P-97, P-99, P-106, P-118, P-120, P-122, P-124, P-125, P-128, P-1 48, P-149, P-150, P-161, P-162, P-163, P-167, P-168, P-178, P-181, P-184 , P-185, P-193, P-194, P-195, P-197, P-242, P-244, P-247, P-248 and P-251.

[0327] Example B7: Gibberella zeae (Fusarium graminearum) / wheat / spikelet (preventive) (Scab) Spikelets of Monsun wheat were placed on agar medium in a multiwell plate (24-well type) and sprayed with the formulated test compound diluted in water. One day after application, the spikelets were inoculated with a fungal spore suspension. After application, the inoculated test leaf discs were incubated in a constant temperature room at 20°C and 60% RH under a photoperiod of 72 hours of semi-darkness followed by 12 hours of light and 12 hours of darkness. When the disease damage on untreated control spikelets reached an appropriate level (6 to 8 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0328] The following compounds, at 200 ppm, provided at least 80% control of Gibberella zeae compared to untreated controls under the same widespread disease conditions: P-6, P-18, P-21, P-22, P-23, P-25, P-38, P-46, P-56, P-59, P-60, P-83, P-94, P-95, P-97, P-117, P-118 , P-120, P-124, P-125, P-128, P-149, P-150, P-161, P-162, P-167, P-168, P-178, P-181, P-193 and P-194.

[0329] Example B8: Phaeosphaeria nodorum (Septoria nodorum) / Wheat / Leaf disc (Preventive) (Septoria blight) Wheat leaf segments of the Kanzler variety were placed on agar medium in a multiwell plate (24-well type) and sprayed with a formulated test compound diluted with water. Two days after application, the leaf discs were inoculated with a fungal spore suspension. After inoculation, the test leaf discs were incubated in a constant temperature room at 20°C and 75% RH under a 12-hour light / 12-hour dark photoperiod. When the disease damage on the untreated control leaf discs reached an appropriate level (5-7 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0330] The following compounds, at 200 ppm, provided at least 80% control of Phaeosphaeria nodorum compared to untreated controls under the same widespread disease conditions: P-2, P-6, P-9, P-12, P-13, P-14, P-16, P-17, P-18, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-29, P-30, P-31, P-32, P-34, P-38 ,P-40,P-41,P-42,P-43,P-44,P-46,P-47,P-48,P-49,P-50,P-51,P-52,P-53,P-54,P-55,P-56,P-57,P-59,P-60,P-61,P-62,P -63, P-64, P-67, P-68, P-69, P-71, P-75, P-77, P-78, P-79, P-80, P-81, P-82, P-83, P-85, P-86, P-89, P-90, P-91, P-92, P-93, P- 94. P-95, P-97, P-98, P-99, P-100, P-101, P-102, P-103, P-105, P-106, P-107, P-109, P-110, P-114, P-116, P-117, P-118, P-120, P-121, P-122, P-124, P-125, P-127, P-128, P-133, P-135, P-142, P-144, P-145, P-148, P-149, P-150, P-151, P-152, P-153, P-15 5. P-156, P-158, P-159, P-160, P-161, P-162, P-163, P-164, P-165, P-167, P-168, P-170, P-171, P-172, P-173, P-174, P-176, P-1 78. P-181, P-184, P-185, P-187, P-189, P-193, P-194, P-195, P-197, P-198, P-203, P-204, P-218, P-219, P-223, P-229, P-230, P- 231, P-232, P-235, P-236, P-237, P-240, P-241, P-242, P-244, P-245, P-247, P-248, P-249, P-250, P-251, P-253, P-254 and P-256.

[0331] Example B9: Monographella nivalis (Microdochium nivale) / liquid culture (Microdochium nivale) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A DMSO solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 4-5 days after application.

[0332] The following compounds, at 20 ppm, provided at least 80% control of Monographella nivalis compared to untreated controls under the same widespread disease conditions: P-2, P-3, P-6, P-9, P-11, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-30 , P-31, P-34, P-37, P-40, P-45, P-46, P-47, P-48, P-49, P-50, P-51, P-52, P-54, P-55, P-56, P-57, P-59, P-60, P-62, P-63, P-64, P-65, P-68, P-69, P-71, P-72, P-74, P-77, P-83, P-84, P-85, P-86, P-88, P-89, P-90, P-92, P-93, P-94, P-95, P-97, P-98, P-100, P-101, P-102, P-106, P-107, P-110, P-112, P-113, P-117, P-118, P-119, P-120, P-121, P-1 22. P-124, P-125, P-127, P-128, P-133, P-142, P-146, P-148, P-149, P-150, P-152, P-155, P-156, P-158, P-159, P- 160, P-161, P-162, P-163, P-164, P-165, P-166, P-167, P-168, P-170, P-172, P-173, P-176, P-178, P-181, P-182, P- 184, P-185, P-186, P-189, P-191, P-193, P-194, P-195, P-197, P-198, P-203, P-204, P-214, P-218, P-219, P-223, P -224, P-231, P-235, P-236, P-240, P-241, P-242, P-244, P-245, P-246, P-247, P-248, P-250, P-253, P-254 and びP-256.

[0333] Example B10: Mycosphaerella arachidis (Mycosphaerella arachidis) arachidicola)) / liquid culture (early leaf spot) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A DMSO solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 4-5 days after application.

[0334] The following compounds, at 20 ppm, provided at least 80% control of Mycosphaerella arachidis compared to untreated controls under the same widespread disease conditions: P-1, P-2, P-4, P-6, P-7, P-9, P-11, P-12, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-28, P-29, P-30, P-31, P-32, P-34, P-37, P-38, P-39, P-40, P-41, P-44, P-45, P-46, P-47, P-48, P-49, P-50, P-51, P-52, P-53, P-54, P-55, P-56, P-57, P-59, P-60, P-61, P-62, P-63, P-64, P-68, P-69, P-71, P-72, P-74, P-77, P-78, P-81, P-83, P-84, P-85, P-86, P-88, P-89, P-90, P-91, P-92, P-93, P-94, P-95, P-97, P-98, P-99, P-100, P-101, P-102, P-104, P-106, P-107, P-109, P-110, P-113, P-117, P-118, P-119, P-120, P-121, P-122, P-124, P-125, P-127, P-128, P-131, P-133, P-142, P-144, P-145, P-146, P-148, P-149, P-150, P-151, P-152, P-155, P-156, P-157, P-158, P-159, P-160, P-161, P-162, P-163, P-164, P-165, P-166, P-167, P-168, P-170, P-171, P-172, P-173, P-176, P-178, P-181, P-182, P-184, P-185, P-189, P-191, P-192, P-193, P-194, P-195, P-197, P-198, P-203, P-204, P-214, P-218, P-219, P-223, P-224, P-230, P-231, P-235, P-236, P-237, P-238, P-240, P-241, P-242, P-244, P-245, P-246, P-247, P-248, P-249, P-250, P-251, P-253, P-254 and P-256.

[0335] Example B11: Puccinia recondita f.sp. tritici / wheat / leaf disc (therapeutic) (leaf rust) Leaf segments of wheat cultivar Kanzler are placed on agar medium in a multiwell plate (24-well type). The leaf segments are inoculated with a fungal spore suspension. The plates are stored in the dark at 19°C and 75% rh. The formulated test compound is diluted with water and applied one day after inoculation. The leaf segments are incubated in a constant temperature room at 19°C and 75% rh under a 12-hour light / 12-hour dark photoperiod. When the disease damage on the untreated control leaf segments reaches an appropriate level (6 to 8 days after application), the activity of the compound is evaluated as the disease control rate compared to the untreated control.

[0336] The following compounds at 200 ppm provided at least 80% control of Puccinia recondita f.sp. tritici compared to untreated controls under the same widespread disease conditions: P-15, P-44, P-52, P-53, P-56, P-60, P-89, P-94, P-95, P-98, P-99, P-118, P-142, P-148, P-151, P-167, P-172, P-173, P-206, P-242, P-247 and P-254.

[0337] Example B12: Puccinia recondita f.sp. tritici / wheat / leaf disc (preventive) (leaf rust) Kanzler wheat leaf segments were placed on agar medium in a multiwell plate (24-well type) and sprayed with formulated test compounds diluted in water. One day after application, the leaf discs were inoculated with a fungal spore suspension. The inoculated leaf segments were incubated in a constant temperature room at 19°C and 75% RH under a 12-hour light / 12-hour dark photoperiod. When the disease damage on the untreated control leaf segments reached an appropriate level (7-9 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0338] The following compounds at 200 ppm provided at least 80% control of Puccinia recondita f.sp. tritici compared to untreated controls under the same widespread disease conditions: P-21, P-23, P-24, P-38, P-46, P-52, P-55, P-56, P-61, P-68, P-89, P-94, P-95, P-97, P-98, P-107, P-118, P-120, P-124, P- 127, P-128, P-142, P-148, P-149, P-150, P-155, P-161, P-164, P-165, P-167, P-168, P-172, P-173, P-181, P-194 and P-206.

[0339] Example B13: Magnaporthe grisea (Pyricularia oryzae) / liquid culture (rice blast) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A DMSO solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 3-4 days after application.

[0340] The following compounds, at 20 ppm, provided at least 80% control of Magnaporthe grisea compared to untreated controls under the same widespread disease conditions: P-117, P-118, P-119, P-120, P-121, P-122, P-124, P-125, P-127, P-128, P-146, P-148, P-149, P-150, P-151, P-152, P-155, P-156, P-158, P -161, P-162, P-163, P-164, P-165, P-167, P-171, P-173, P-174, P-175, P-176, P-178, P-179, P-181, P-182, P-183, P-184, P-185, P-189, P-1 91, P-192, P-193, P-194, P-195, P-197, P-198, P-200, P-203, P-204, P-205, P-214, P-216, P-218, P-219, P-221, P-222, P-223, P-224, P-22 6, P-235, P-236, P-237, P-239, P-240, P-241, P-242, P-244, P-245, P- 246, P-247, P-248, P-249, P-250, P-251, P-253, P-254, P-255, P-256.

[0341] Example B14: Magnaporthe grisea (Pyricularia oryzae) / Rice / Leaf disc (Preventive) (Rice blast) Leaf segments of Ballila rice cultivar were placed on agar medium in a multiwell plate (24-well type) and sprayed with formulated test compounds diluted in water. Two days after application, the leaf segments were inoculated with a fungal spore suspension. The inoculated leaf segments were incubated in a constant temperature room at 22°C and 80% RH under a 24-h dark period followed by a 12-h light / 12-h dark photoperiod. When the disease damage on untreated control leaf segments reached an appropriate level (5-7 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0342] The following compounds, at 200 ppm, provided at least 80% control of Magnaporthe grisea compared to untreated controls under the same widespread disease conditions: P-21, P-22, P-23, P-29, P-53, P-78, P-94.

[0343] Example B15: Pyrenophora teres / barley / leaf disc (preventive) (net blotch) Leaf segments of Hasso barley were placed on agar medium in a multiwell plate (24-well type) and sprayed with a formulated test compound diluted with water. Two days after application, the leaf segments were inoculated with a fungal spore suspension. The inoculated leaf segments were incubated in a constant temperature room at 20°C and 65% rh under a 12-hour light / 12-hour dark photoperiod. When the disease damage on the untreated control leaf segments reached an appropriate level (5-7 days after application), the activity of the compound was evaluated as the disease control rate compared to the untreated control.

[0344] The following compounds, at 200 ppm, provided at least 80% control of Pyrenophora teres compared to untreated controls under the same widespread disease conditions: P-2, P-3, P-6, P-9, P-10, P-11, P-12, P-13, P-14, P-15, P-16, P-17, P-18, P-19, P-21, P-22, P-23, P-24, P-25, P-26, P-27, P-29, P-30, P-31, P-32, P-33, P-35, P-38, P-40, P-41, P-42, P-43, P-44, P-46, P-47, P-48, P-49, P-50, P-51, P-52, P-53, P-54, P-55, P-56, P-57, P-59, P-60, P-61, P-62, P-63, P-64, P-67, P-68, P-69, P-71, P-75, P-77, P-78, P-79, P-81, P-83, P-85, P-86, P-87, P-88, P-89, P-90, P-91, P-92, P-93, P-94, P-95, P-96, P-97, P-98, P-99, P-100, P-101, P-102, P-103, P-105, P-106, P-107, P-108, P-109, P-110, P-112, P-114, P-116, P-117, P-118, P-120, P-121, P-122, P-124, P-125, P-127, P-128, P-129, P-131, P-133, P-142, P-144, P-145, P-146, P-147, P-148, P-149, P-150, P-151, P-152, P-153, P-155, P-156, P-158, P-159, P-160, P-161, P-162, P-163, P-164, P-165, P-166, P-167, P-168, P-169, P-170, P-171, P-172, P-173, P-174, P-176, P-178, P-179, P-181, P-184, P-185, P-186, P-187, P-189, P-191, P-193, P-194, P-195, P-196, P-197, P-198, P-203, P-204, P-214, P-218, P-219, P-220, P-221, P-223, P-224, P-229, P-230, P-231, P-232, P-235, P-237, P-239, P-240, P-241, P-242, P-244, P-245, P-247, P-248, P-249, P-250, P-251, P-253, P-254 and P-256.

[0345] Example B16: Thanatephorus cucumeris (Rhizoctonia solani) / liquid culture (foot rot, damping-off) Mycelial fragments from freshly grown liquid cultures of the fungus are mixed directly into nutrient medium (PDB potato dextrose medium). A solution of the test compound (DMSO) is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal material is added. The test plates are incubated at 24°C, and growth inhibition is determined photometrically 3-4 days after application.

[0346] The following compounds, at 20 ppm, provided at least 80% control of Thanatephorus cucumeris compared to untreated controls under the same widespread disease conditions: P-2, P-21, P-22, P-23, P-24, P-26, P-46, P-47, P-48, P-54, P-55, P-56, P-57, P-59, P-60, P-62, P-64 , P-68, P-69, P-71, P-72, P-74, P-94, P-95, P-97, P-98, P-100, P-106, P-109, P-118, P-120, P-122, P- 124, P-125, P-127, P-128, P-148, P-149, P-150, P-152, P-155, P-161, P-162, P-164, P-168, P-178, P -181, P-184, P-185, P-194, P-214, P-219, P-236, P-240, P-241, P-242, P-244, P-245, P-247 and P-256.

[0347] Example B17: Sclerotinia sclerotiorum / liquid culture (sclerotinia rot) Mycelial fragments from freshly grown liquid cultures of the fungus are mixed directly into nutrient medium (PDB potato dextrose medium). A solution of the test compound (DMSO) is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal material is added. The test plates are incubated at 24°C, and growth inhibition is determined photometrically 3-4 days after application.

[0348] The following compounds, at 20 ppm, provided at least 80% control of Sclerotinia sclerotiorum compared to untreated controls under the same widespread disease conditions: P-18, P-21, P-22, P-23, P-25, P-94, P-118, P-120, P-122, P-124, P-125, P-127, P-128, P-129, P-148, P-149, P-150, P-155, P-156, P-168, P-181, P-184, P-194, P-241, P-242, P-244 and P-247.

[0349] Example B18: Mycosphaerella graminicola (Septoria tritici) / liquid culture (leaf blight) Cryogenically preserved fungal conidia are mixed directly into nutrient medium (Vogel's medium (PDB potato dextrose medium)). A DMSO solution of the test compound is placed in a 96-well microtiter plate, after which the nutrient medium containing the fungal spores is added. The test plate is incubated at 24°C, and growth inhibition is determined photometrically 4-5 days after application.

[0350] The following compounds, at 20 ppm, provided at least 80% control of Mycosphaerella graminicola compared to untreated controls under the same widespread disease conditions: P-2、P-3、P-4、P-5、P-6、P-9、P-10、P-11、P-12、P-13、P-14、P-15、P-16、P-17、P-18、P-19、P-21、P-22、P-23、P-24、P-25、P-26、P-27、P-28、P-29、P-30、P-31、P-32、P-34、P-36、P-37、P-38、P-39、P-40、P-41、P-42、P-43、P-44、P-45、P-46、P-47、P-48、P-49、P-50、P-51、P-52、P-53、P-54、P-55、P-56、P-57、P-58、P-59、P-60、P-61、P-62、P-63、P-64、P-65、P-67、P-68、P-69、P-70、P-71、P-72、P-73、P-74、P-76、P-77、P-78、P-80、P-81、P-82、P-83、P-84、P-85、P-86、P-88、P-89、P-90、P-91、P-92、P-93、P-94、P-95、P-97、P-98、P-99、P-100、P-101、P-102、P-103、P-105、P-106、P-107、P-108、P-109、P-110、P-111、P-112、P-113、P-116、P-117、P-118、P-119、P-120、P-121、P-122、P-124、P-125、P-127、P-128、P-131、P-133、P-134、P-141、P-142、P-144、P-145、P-146、P-148、P-149、P-150、P-151、P-152、P-153、P-155、P-156、P-157、P-158、P-159、P-160、P-161、P-162、P-163、P-164、P-165、P-166、P-167、P-168、P-169、P-170、P-171、P-172、P-173、P-174、P-176、P-178、P-179、P-181、P-182、P-184、P-185、P-186、P-189、P-190、P-191、P-192、P-193、P-194、P-195、P-197、P-198、P-200、P-203、P-204、P-214、P-216、P-218、P-219、P-221、P-223、P-224、P-225、P-226、P-229、P-230、P-231、P-232、P-233、P-234、P-235、P-236, P-237, P-238, P-240, P-241, P-242, P-244, P-245, P-246, P-247, P-248, P-249, P-250, P-251, P-252, P-253, P-254, P-255 and P-256.

Claims

1. Formula (I): 【Chemistry 1】 (In the formula, B 1 is CR 7 or N, B 2 is CR 8 or N, B 3 is CR 9 or N, R 1 is hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl or C 3 ~C 6 cycloalkyl; R 2 is hydrogen, halogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 4 Alkylcarbonyl, N—C 1 ~C 4 Alkoxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 Alkyl-carbonimidoyl or C 1 ~C 4 alkoxycarbonyl; R 3 is hydrogen, halogen, C 1 ~C 4 Haloalkyl or C 1 ~C 4 alkyl, R 4 is hydrogen, halogen, C 1 ~C 4 Haloalkyl, C 3 ~C 6 Cycloalkyl or C 1 ~C 4 alkyl, R 5 , R 6 , R 7 , R 8 and R 9 is hydrogen, halogen, hydroxy, amino, cyano, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxy, C 2 to C4 alkenyloxy, C 2 ~C 4 Alkynyloxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkoxy-C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 Alkylcarbonyl, carbamoyl, C 1 ~C 4 Alkylaminocarbonyl, di(C 1 ~C 4 ) alkylaminocarbonyl, cyano-C 1 ~C 4 Alkyl, N-C 1 ~C 4 Alkoxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, C 1 ~C 4 Alkylamino, C 1 ~C 4 dialkylamino, trifluoromethylsulfonyloxy, carboxy, phenyl, 5- to 6-membered saturated, partially saturated or aromatic heterocycle or C 3 ~C 6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycles contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; and any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocycles is unsubstituted or selected from halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl and C 1 ~C 4 substituted with 1, 2 or 3 substituents independently selected from alkoxy; 3 ~C 6 Cycloalkyl is unsubstituted or substituted with halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 substituted with 1, 2, or 3 substituents independently selected from alkoxy; Z 1 is C 1 ~C 6 alkyl, wherein C 1 ~C 6 The alkyl may be unsubstituted or may contain halogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 2 ~C 4 Alkynyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 Haloalkoxy, C 2 ~C 4 Alkenyloxy, C 2 ~C 4 Alkynyloxy, C 1 ~C 4 Alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 Alkylsulfonyl, C 1 ~C 4 Alkoxy-C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 Alkylcarbonyl, N—C 1 ~C 4 Alkoxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- to 6-membered saturated, partially saturated or aromatic heterocycle or C 3 ~C 6 cycloalkyl, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocycles contains 1, 2, or 3 heteroatoms selected from O, S, or N, provided that not more than one is O or S; and any of the phenyl and the 5- to 6-membered saturated, partially saturated, or aromatic heterocycles is unsubstituted or is selected from halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 substituted with 1, 2 or 3 substituents independently selected from alkoxy; 3 ~C 6 Cycloalkyl is unsubstituted or substituted with halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 substituted with 1, 2, or 3 substituents independently selected from alkoxy; or an agrochemically acceptable salt, stereoisomer or N-oxide thereof.

2. R 1 is methyl, and R 3 The compound of formula (I) according to claim 1, wherein is hydrogen.

3. R 2 3. A compound of formula (I) according to claim 1 or 2, wherein is hydrogen, chlorine or methyl.

4. R 4 A compound of formula (I) according to any one of claims 1 to 3, wherein is hydrogen.

5. B 1 is CR 7 and B 2 is CR 8 and B 3 A compound of formula (I) according to any one of claims 1 to 4, wherein is N.

6. R 7 and R 8 is hydrogen, halogen, cyano, hydroxy, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkoxy, C 1 ~C 4 haloalkoxy or C 3 ~C 6 cycloalkyl, wherein C 3 ~C 6 Cycloalkyl is unsubstituted or is substituted with halogen, cyano or C 1 ~C 4 A compound of formula (I) according to any one of claims 1 to 5, substituted with one substituent selected from alkyl.

7. R 7 and R 8 are independently selected from hydrogen, chlorine, bromine, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methoxy, ethoxy, methoxymethoxy, 2-methoxyethoxy, methoxycarbonyl, hydroxy, cyano, cyclopropyl, cyanocyclopropyl, or methylcyclopropyl.

8. R 5 A compound of formula (I) according to any one of claims 1 to 7, wherein is hydrogen, fluorine, chlorine, bromine, methyl or cyano.

9. R 6 A compound of formula (I) according to any one of claims 1 to 8, wherein is hydrogen, chlorine, bromine, fluorine, methyl, cyano or cyclopropyl.

10. Z 1 is C 1 ~C 6 alkyl, 1 ~C 6 The alkyl may be unsubstituted or may contain halogen, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 and substituted with 1, 2 or 3 substituents independently selected from alkylcarbonyl, phenyl, and a 5- to 6-membered saturated, partially saturated or aromatic heterocyclic ring, wherein any of the 4-, 5- or 6-membered saturated, partially saturated or aromatic heterocyclic rings contains 1, 2 or 3 heteroatoms selected from O, S or N, provided that not more than one is O or S; and any of the phenyl and 5- to 6-membered saturated, partially saturated or aromatic heterocyclic rings is unsubstituted or is selected from halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 substituted with one or two substituents independently selected from alkoxy; 3 ~C 6 Cycloalkyl is unsubstituted or substituted with halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 A compound of formula (I) according to any one of claims 1 to 9, substituted with one or two substituents independently selected from alkoxy.

11. Z 1 is C 1 ~C 6 alkyl, 1 ~C 6 The alkyl may be unsubstituted or may contain halogen, C 1 ~C 4 Haloalkyl, C 1 ~C 4 Alkyl, C 1 ~C 4 Haloalkoxy, C 1 ~C 4 Alkoxycarbonyl, C 1 ~C 4 and substituted with one or two substituents independently selected from alkylcarbonyl, phenyl, or a 5- to 6-membered saturated, partially saturated, or aromatic heterocyclic ring, wherein any of the 4-, 5-, or 6-membered saturated, partially saturated, or aromatic heterocyclic rings contains one, two, or three heteroatoms selected from O, S, or N, provided that not more than one is O or S; and any of the phenyl and 5- to 6-membered saturated, partially saturated, or aromatic heterocyclic rings is unsubstituted or is selected from halogen, C 1 ~C 4 Haloalkyl, cyano, C 1 ~C 4 Alkyl or C 1 ~C 4 substituted with one or two substituents independently selected from alkoxy; 3 ~C 6 Cycloalkyl is unsubstituted or substituted with halogen, C 1 Cyano or C 1 ~C 4 11. A compound of formula (I) according to claim 10, substituted with one substituent selected from alkyl.

12. A pesticide composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 11.

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

14. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 11 or a composition comprising said compound of formula (I) to said plants, parts thereof or their habitats.

15. Use of a compound according to any one of claims 1 to 11 as a fungicide.

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