Pyrazole compound, production intermediate thereof, and pest control agent

Abstract

The present invention provides: a pyrazole compound having a structure represented by formula (1) or a salt thereof; and a novel fungicide, particularly an agricultural and horticultural fungicide, containing the pyrazole compound or the salt thereof as an active ingredient. In the formula, G represents G-1, G1 represents a C1-C6 haloalkyl group or the like, T represents an oxygen atom or the like, RX represents a C1-C6 alkyl group or the like, RY represents a hydrogen atom or the like, R1 represents a hydrogen atom or the like, R2 represents a hydrogen atom or the like, R3 represents a hydrogen atom or the like, Ra represents a hydrogen atom or the like, Z represents Z-1 or the like, Z1 represents a C1-C6 alkyl group or the like, m5 and n5 represent integers 0, 1, 2, 3, 4 or 5, and p represents an integer 0 or 1. [Chemical Formula 1] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a novel pyrazole compound and a salt thereof, a production intermediate thereof, and a pest control agent containing the compound and a salt thereof as an active ingredient. Background Art

[0002] Patent Documents 1 and 2 disclose certain pyrazole compounds, but do not disclose the pyrazole compound according to the present invention.

[0003] In addition, Patent Documents 3 and 4 disclose that certain pyrazole compounds are effective as fungicides, but there is no disclosure about the pyrazole compound according to the present invention.

[0004] Furthermore, Patent Documents 5 to 8 disclose that certain heterocyclic compounds are effective as fungicides, but do not disclose anything about the pyrazole compound of the present invention.

[0005] (Prior art literature)

[0006] Patent Document 1: International Publication No. 2002 / 085860

[0007] Patent Document 2: International Publication No. 2006 / 132197

[0008] Patent Document 3: International Publication No. 2009 / 028280

[0009] Patent Document 4: International Publication No. 1996 / 038419

[0010] Patent Document 5: International Publication No. 2020 / 109391

[0011] Patent Document 6: International Publication No. 2021 / 224220

[0012] Patent Document 7: International Publication No. 2021 / 228734

[0013] Patent Document 8: International Publication No. 2021 / 233861 Summary of the invention

[0014] (Problems to be solved by the invention)

[0015] However, long-term use of drugs may lead to the acquisition of drug resistance by pathogens. Therefore, the development of new drugs with excellent control effects has been expected.

[0016] (Technical means to solve the problem)

[0017] The present inventors have conducted intensive studies to solve the above problems and have found that the novel pyrazole compound represented by the following formula (1) of the present invention exhibits excellent control activity as a fungicide, particularly as an agricultural and horticultural fungicide, thereby completing the present invention.

[0018] The pyrazole compound of the present invention is not disclosed in any document, and its usefulness as a pest control agent is also unknown.

[0019] That is, the present invention relates to the following item [1].

[0020] [1]

[0021] A pyrazole compound represented by formula (1) or a salt thereof.

[0022] [Chemical formula 1]

[0023]

[0024] In the formula, G represents G-1, and G-1 represents the structure shown in the following structural formula,

[0025] [Chemical formula 2]

[0026]

[0027] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R',

[0028] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0029] R b Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R',

[0030] R represents a hydrogen atom or a C1-C6 alkyl group,

[0031] R' represents a C1-C6 alkyl group,

[0032] T represents an oxygen atom or a sulfur atom,

[0033] R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0034] R X -1~R X -4 represent the structures shown in the following structural formulas,

[0035] [Chemical formula 3]

[0036]

[0037] X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0038] About X 1 When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0039] About X 1 When u4 represents an integer of 2, 3 or 4, each X 1 may be the same as or different from each other,

[0040] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0041] R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0042] R 1 represents a hydrogen atom or a C1-C6 alkyl group,

[0043] R 2 represents a hydrogen atom or a C1-C6 alkyl group,

[0044] R 3represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0045] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0046] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6, R a -1. R a -2. R a -3. R a -4. R a -5 and R a -6 represent the structures shown in the following structural formulas,

[0047] [Chemical formula 4]

[0048]

[0049] R 5 represents a hydrogen atom or a C1-C6 alkyl group,

[0050] R 6 represents a hydrogen atom or a C1-C6 alkyl group,

[0051] In r 1 In the case of the integer 2, the two R 5 and two R 6 may be the same as or different from each other,

[0052] R 7 Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl or phenyl,

[0053] R 8 represents a hydrogen atom or a C1-C6 alkyl group,

[0054] R 9 represents a hydrogen atom or a C1-C6 alkyl group,

[0055] Z represents Z-1, Z-2, Z-3, Z-4, Z-5, Z-6 or Z-7,

[0056] Z-1 to Z-7 represent the structures shown in the following structural formulas, respectively,

[0057] [Chemical formula 5]

[0058]

[0059] Among them, Z 1 The substitution position refers to substitution on the aromatic rings of Z-1 to Z-7,

[0060] Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, R i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, E-1 to E-54, F-1 to F-15 or -C(=NOR)R',

[0061] About Z 1 When n3 represents an integer of 2 or 3, each Z 1 may be the same as or different from each other,

[0062] About Z 1 When n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other,

[0063] About Z 1 When n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other,

[0064] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, E-1-E-54, F-1-F-15 or C1-C6 alkylaminocarbonyl,

[0065] R 10 Represents C3~C 10Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, E-1-E-54, F-1-F-15 or -C(=NOR)R',

[0066] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, benzyloxy, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino,

[0067] R f represents C1-C6 alkyl, C1-C6 haloalkyl, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino,

[0068] R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group,

[0069] R h represents a C1-C6 alkyl group,

[0070] R i represents a hydroxyl group or a C1-C6 alkoxy group,

[0071] E-1 to E-54 represent the structures shown in the following structural formulas,

[0072] [Chemical formula 6]

[0073]

[0074] F-1 to F-15 represent the structures shown in the following structural formulas,

[0075] [Chemical formula 7]

[0076]

[0077] Z a represents a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylcarbonyl group or a C1-C6 alkoxycarbonyl group,

[0078] About Z a When v7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other,

[0079] About Z a When v6 represents an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other,

[0080] About Z a When v5 represents an integer of 2, 3, 4 or 5, each Z a may be the same as or different from each other,

[0081] About Z a When v4 represents an integer of 2, 3, or 4, each Z a may be the same as or different from each other,

[0082] About Z a The relationship between them is that when v3 represents an integer of 2 or 3, each Z a may be the same as or different from each other,

[0083] About Z a The relationship between them, when v2 represents the integer 2, each Z a may be the same as or different from each other,

[0084] Z b represents a C1-C6 alkyl group,

[0085] m5, n5 and u5 represent integers 0, 1, 2, 3, 4 or 5,

[0086] n3 represents an integer 0, 1, 2 or 3,

[0087] u4 represents an integer 0, 1, 2, 3, or 4,

[0088] n7 represents an integer 0, 1, 2, 3, 4, 5, 6 or 7,

[0089] p represents an integer 0 or 1,

[0090] r 1 represents an integer 1 or 2,

[0091] r 2 Represents an integer 0 or 1,

[0092] t represents an integer 0, 1 or 2,

[0093] v1 represents an integer 0 or 1,

[0094] v2 represents an integer 0, 1, or 2,

[0095] v3 represents an integer 0, 1, 2, or 3,

[0096] v4 represents an integer 0, 1, 2, 3, or 4,

[0097] v5 represents an integer 0, 1, 2, 3, 4, or 5,

[0098] v6 represents an integer 0, 1, 2, 3, 4, 5, or 6,

[0099] v7 represents an integer 0, 1, 2, 3, 4, 5, 6, or 7.

[0100] (Effects of the Invention)

[0101] The compound of the present invention represented by formula (1) exhibits excellent control activity against various pathogenic bacteria.

[0102] Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agricultural and horticultural use. DETAILED DESCRIPTION

[0103] Hereinafter, the present invention will be described in detail.

[0104] The compounds of the present invention may have geometrical isomers such as E-isomers and Z-isomers depending on the types of substituents, but the compounds of the present invention include those containing E-isomers, Z-isomers, or mixtures of E-isomers and Z-isomers in any ratio. In this specification, compounds having geometrical isomers are expressed as follows: For example, the following formula (1-R a -6) A compound having a bond represented by a wavy line.

[0105] [Chemical formula 8]

[0106]

[0107] In addition, the compound of the present invention may have optically active forms due to the presence of one or two or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compound of the present invention includes all optically active forms or racemic forms.

[0108] In addition, the compound of the present invention may exist in tautomers depending on the kind of substituents, and the compound of the present invention includes all tautomers or a mixture containing tautomers in any ratio.

[0109] In addition, the compounds of the present invention may exist as one or more rotational isomers due to bond rotation restricted by steric hindrance between substituents. The compounds of the present invention include all rotational isomers or mixtures containing diastereomers in any ratio.

[0110] Next, specific examples of each substituent described in this specification are shown below. Here, "n-" represents normal, "i-" represents iso, "s-" represents secondary, "tert-" represents tertiary, and "Ph" represents phenyl.

[0111] Examples of the "halogen atom" in the present specification include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Here, the "halogen" in the present specification also represents these halogen atoms.

[0112] In this manual, “C a ~C b "Alkyl" represents a straight-chain or branched saturated hydrocarbon group having a to b carbon atoms. a ~C b Specific examples of the "alkyl" group include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl. a ~C b The "alkyl" is selected from a specified range of carbon atoms.

[0113] In this manual, “C a ~C b "Haloalkyl" represents a linear or branched saturated hydrocarbon group having a to b carbon atoms, in which the hydrogen atoms bonded to the carbon atoms are arbitrarily replaced by halogen atoms. When substituted by two or more halogen atoms, these halogen atoms may be the same or different from each other. a ~C b Specific examples of the “haloalkyl” include, for example, fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl and 2,2,2-trichloroethyl. a ~C b The "haloalkyl" is selected from a specified range of carbon number.

[0114] In this manual, “C a ~C b "Alkenyl" represents a linear or branched unsaturated hydrocarbon having a to b carbon atoms and one or more double bonds in the molecule. a ~C b Specific examples of "alkenyl" include, for example, vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylvinyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl and 1,1-dimethyl-2-propenyl. a ~C b The "alkenyl" group is selected from a specified range of carbon atoms.

[0115] In this manual, “C a ~C b "Alkynyl" represents a linear or branched unsaturated hydrocarbon having a to b carbon atoms and one or more triple bonds in the molecule. a ~Cb Specific examples of "alkynyl" include, for example, ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-hexynyl, and the like. a ~C b The "alkynyl" group is selected from a specified range of carbon atoms.

[0116] In this manual, “C a ~C b "Alkoxy" represents the above alkyl-O- having a carbon atom number of a to b. a ~C b Specific examples of the "alkoxy group" include, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy and 2-ethylhexyloxy. a ~C b The "alkoxy" is selected from a specified range of carbon number.

[0117] In this manual, “C a ~C b "Haloalkoxy" represents the above-mentioned haloalkyl-O- having a carbon number of a to b. a ~C b Specific examples of the "halogenated alkoxy" include, for example, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy and 1,1,2,3,3,3-hexafluoropropoxy. a ~C b The "haloalkoxy" is selected from a specified range of carbon number.

[0118] In this manual, “C a ~C b "Alkenyloxy" represents an alkenyl-O- group having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of "alkenyloxy" include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylvinyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, 1,1-dimethyl-2-propenyloxy, and the like. a ~C b The "alkenyloxy" is selected from a specified range of carbon number.

[0119] In this manual, “C a ~C b "Alkylthio" represents an alkyl-S- group with the above meaning and having a to b carbon atoms. a ~C bSpecific examples of the "alkylthio group" include, for example, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio and tert-butylthio. a ~C b The "alkylthio" group is selected from a specified range of carbon number.

[0120] In this manual, “C a ~C b "Alkylsulfinyl" represents an alkyl-S(O)- group having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of the "alkylsulfinyl group" include, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, s-butylsulfinyl and tert-butylsulfinyl. a ~C b The "alkylsulfinyl" group is selected from a specified range of carbon atoms.

[0121] In this manual, “C a ~C b "Alkylsulfonyl" represents an alkyl-SO2- having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of the "alkylsulfonyl group" include, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl and tert-butylsulfonyl. a ~C b The "alkylsulfonyl" is selected from a specified range of carbon atoms.

[0122] In this manual, “C a ~C b "Cycloalkyl" represents a cyclic hydrocarbon group having a to b carbon atoms. a ~C b The "cycloalkyl" may be formed into a single ring or a double ring structure of, for example, a 3-membered ring to a 10-membered ring. In addition, the hydrogen in each ring may be arbitrarily replaced by an alkyl group having a specified range of carbon atoms. a ~C b Specific examples of "cycloalkyl" include, for example, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. a ~C b The "cycloalkyl" is selected from a specified range of carbon atoms.

[0123] In this manual, “C a ~C bThe term "halogenated cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to carbon atoms are arbitrarily replaced by halogen atoms. When substituted by two or more halogen atoms, these halogen atoms may be the same or different from each other. a ~C b Specific examples of the "halogenated cycloalkyl" include, for example, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl and 2,2,3,3-tetrafluorocyclobutyl. a ~C b The "halocycloalkyl" is selected from a specified range of carbon number.

[0124] In this manual, “C a ~C b "Alkylamino" means an amino group in which a single hydrogen atom is replaced by an alkyl group having a to b carbon atoms as defined above. a ~C b Specific examples of the "alkylamino" include, for example, methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino and tert-butylamino. a ~C b The "alkylamino" is selected from a specified range of carbon number.

[0125] In this specification, “two (C a ~C b "Di(C)-(alkyl)amino" means an amino group in which both hydrogen atoms are replaced by an alkyl group having a to b carbon atoms which may be the same or different and having the above meaning. a ~C b Specific examples of the "di(C-alkyl)amino" group include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino and di(n-butyl)amino. a ~C b Each alkyl group in the "alkyl)amino" is selected from the range of the specified number of carbon atoms.

[0126] In this manual, “C a ~C b "Alkylcarbonyl" means an alkyl-C(O)- group having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of the "alkylcarbonyl group" include, for example, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutyryl, pivaloyl, hexanoyl, heptanoyl, and the like. a ~C bThe "alkylcarbonyl" is selected from a range specifying the number of carbon atoms.

[0127] In this manual, “C a ~C b "Alkoxycarbonyl" represents an alkyl-OC(O)- having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of the "alkylcarbonyl group" include, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl and 2-ethylhexyloxycarbonyl. a ~C b The "alkylcarbonyl" is selected from a range specifying the number of carbon atoms.

[0128] In this manual, “C a ~C b "Alkylaminocarbonyl" represents a carbamoyl group substituted by an alkyl group, wherein one of the hydrogen atoms has the above meanings with a to b carbon atoms. a ~C b Specific examples of the "alkylaminocarbonyl group" include, for example, methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl and tert-butylcarbamoyl. a ~C b The "alkylaminocarbonyl" is selected from a range specifying the number of carbon atoms.

[0129] In this manual, “C a ~C b "Cycloalkylaminocarbonyl" represents a carbamoyl group in which a single hydrogen atom is replaced by a cycloalkyl group having the above-mentioned meaning and having a to b carbon atoms. a ~C b Specific examples of the "cycloalkylaminocarbonyl" include, for example, cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl and cyclohexylcarbamoyl. a ~C b The "cycloalkylaminocarbonyl" is selected from a range with a designated number of carbon atoms.

[0130] In this specification, “two (C a ~C b "(C)-(alkylaminocarbonyl)" represents a carbamoyl group in which both hydrogen atoms are replaced by an alkyl group having a to b carbon atoms which may be the same or different and having the above meaning. a ~C bSpecific examples of the “di(C)alkylaminocarbonyl” group include, for example, N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl and N,N-di(n-butyl)carbamoyl. a ~C b Each alkyl group in the "alkylaminocarbonyl group" is selected from the range of the specified number of carbon atoms.

[0131] In this manual, “three (C a ~C b "Tri(C)alkylsilyl" means a silyl group substituted by an alkyl group having a to b carbon atoms which may be the same or different from the above-mentioned alkyl group. a ~C b Specific examples of the "tri(C)alkylsilyl" group include, for example, trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl and tert-butyldimethylsilyl. a ~C b Each alkyl group in the "alkylsilyl group" is selected from the range of the specified number of carbon atoms.

[0132] In this manual, the term “ c Replaced by C a ~C b Alkyl", "R i Replaced by C a ~C b Alkyl" or "R 10 Substituted C a ~C b "Alkyl" means any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R c , R i or R 10 A partially or fully substituted alkyl group having a to b carbon atoms as defined above. Each of them is selected from the specified range of carbon atoms. c , R i or R 10 When there are two or more substituents, c , R i or R 10 They may be the same as each other or may be different from each other.

[0133] In this manual, the term “ b Replaced by C a ~C b "Alkoxy" means any hydrogen atom bonded to a carbon atom is replaced by one or more substituents R bA partially or fully substituted alkoxy group having a to b carbon atoms as defined above. b Replaced by C a ~C b The alkoxy group is selected from a specified range of carbon atoms. The substituent R b When there are two or more substituents, b They may be the same as each other or may be different from each other.

[0134] The "benzyl group" described in this specification represents -CH2C6H5.

[0135] The "benzyloxy group" described in this specification represents -O-CH2C6H5.

[0136] Next, the method for producing the compound of the present invention represented by formula (1) is described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. Here, the following description is merely illustrative, and the compound of the present invention represented by formula (1) can also be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" is also recorded as "compound (1)", and in addition, "the compound represented by formula (2)" is also recorded as "compound (2)". The recording method of other compounds is also similar.

[0137] (Production Example 1)

[0138] The compound (1) of the present invention can be produced, for example, by the following production method.

[0139] [Chemical formula 9]

[0140]

[0141] In the formula, G, T, R X , R Y , R 1 , R 2 , R 3 , R 4 , R a , Z and p have the same meanings as mentioned above.

[0142] Compound (1) can be produced by reacting compound (1-1), compound (1-a) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate), and a dehydrating condensation agent in a solvent or in the absence of a solvent and optionally in the presence of either or both of a base and an additive.

[0143] The amount of the compound (1-a) or a salt thereof and the amount of the dehydration condensation agent used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (1-1).

[0144] Some of the compounds represented by compound (1-a) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (1-a) other than commercial products may also be produced by synthetic methods of generally known compounds described in literature.

[0145] Examples of the dehydration condensation agent include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N′-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate.

[0146] If a solvent is used, the solvent used may be inactive to the reaction, and examples of the solvent include: water; alcohol solvents such as methanol, ethanol or tert-butanol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane or diethylene glycol dimethyl ether; aromatic hydrocarbon solvents such as benzene, xylene or toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane or cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform or 1,2-dichloroethane; nitrile solvents such as acetonitrile or propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or mixed solvents thereof.

[0147] The reaction can be carried out in the presence of a base. Examples of the base that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabispiro[2.2.2]octane (DABCO), 1,8-diazabispiro[5.4.0]-7-undecene (DBU) or 1,5-diazabispiro[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium carbonate, cesium carbonate or potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide or potassium tert-butoxide. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-1).

[0148] The reaction may be carried out in the presence of an additive. Examples of the additive include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine. The amount of the additive used may be 0.005 to 100 equivalents relative to 1 equivalent of compound (1-1).

[0149] The reaction temperature can be set at any temperature within the range of -78°C to the reflux temperature of the reaction mixture. The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can generally be set at any time within the range of 5 minutes to 100 hours.

[0150] (Production Example 2)

[0151] The compound (2) of the present invention can be produced, for example, by the following production method.

[0152] [Chemical formula 10]

[0153]

[0154] In the formula, L is a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a C1-C4 alkylsulfonyloxy group (e.g., a methanesulfonyloxy group, etc.), a halogenated sulfonyloxy group (e.g., a fluorosulfonyloxy group, etc.), a C1-C4 halogenated alkylsulfonyloxy group (e.g., a trifluoromethanesulfonyloxy group, etc.), or an arylsulfonyloxy group (e.g., a p-toluenesulfonyloxy group, etc.), and R Xa Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl or benzyl, G, T, R Y , R 1 , R 2 , R 3 , R 4 , R a , R c , Z and p have the same meanings as mentioned above.

[0155] Compound (2) can be produced by reacting compound (2-1) with compound (D) in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0156] The amount of the compound (D) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (2-1).

[0157] Some of the compounds represented by compound (D) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (D) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0158] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0159] Examples of the base that can be used in the reaction include the bases listed in Production Example 1. The amount of the base to be used may be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-1).

[0160] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0161] (Production Example 3)

[0162] The compound (5) or the compound (6) of the present invention can be produced, for example, by the following production method.

[0163] [Chemical formula 11]

[0164]

[0165] In the formula, G, T, R X , R Y , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z, r 1 The meanings of and p are the same as above.

[0166] Compound (5) or compound (6) can be produced by reacting compound (4) of the present invention with an oxidizing agent in a solvent or in the absence of a solvent.

[0167] Examples of the oxidizing agent that can be used include hydrogen peroxide and m-chloroperbenzoic acid. The amount of the oxidizing agent used may be 0.1 to 100 equivalents relative to 1 equivalent of the compound (4).

[0168] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0169] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0170] Compound (4) can be synthesized according to the method of Preparation Example 1.

[0171] (Production Example 4)

[0172] The compound (8) of the present invention can be produced, for example, by the following production method.

[0173] [Chemical formula 12]

[0174]

[0175] In the formula, R 1a Represents C1-C6 alkyl, G, L, T, R X , RY , R 2 , R 3 , R 4 , R a , Z and p have the same meanings as mentioned above.

[0176] Compound (8) can be produced by reacting the compound (7) of the present invention with compound (D1) in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0177] The amount of the compound (D1) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (7).

[0178] Some of the compounds represented by compound (D1) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (D1) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0179] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0180] Examples of the base that can be used in the reaction include the bases listed in Production Example 1. The base can be used in an amount of 0.1 to 100 equivalents relative to 1 equivalent of Compound (7).

[0181] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0182] Compound (7) can be synthesized according to the method of Preparation Example 1.

[0183] (Production Example 5)

[0184] The compound (10) of the present invention can be produced, for example, by the following production method.

[0185] [Chemical formula 13]

[0186]

[0187] In the formula, G, R X , R Y , R 1 , R 2 , R 3 , R 4 , R a , Z and p have the same meanings as mentioned above.

[0188] Compound (10) can be produced by reacting compound (9) of the present invention with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphatane 2,4-disulfide (hereinafter also referred to as "Lawesson's reagent") in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0189] The amount of Lawesson's reagent used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (9).

[0190] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0191] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0192] Compound (9) can be synthesized according to the method of Preparation Example 1.

[0193] (Production Example 6)

[0194] The compound (12) of the present invention can be produced, for example, by the following production method.

[0195] [Chemical formula 14]

[0196]

[0197] In the formula, R d1 represents C1~C6 alkyl or R d , G, L, T, R X , R Y , R 2 , R 3 , R 4 , R a , R d The meanings of and p are the same as above.

[0198] Compound (12) can be produced by reacting the compound (11) of the present invention with compound (D2) in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0199] The amount of the compound (D2) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (11).

[0200] Some of the compounds represented by compound (D2) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (D2) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0201] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0202] Examples of the base that can be used in the reaction include the bases listed in Production Example 1. The base can be used in an amount of 0.1 to 100 equivalents relative to 1 equivalent of Compound (11).

[0203] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0204] Compound (11) can be synthesized according to the method of Preparation Example 1.

[0205] (Production Example 7)

[0206] The compound (14) or the compound (15) of the present invention can be produced, for example, by the following production method.

[0207] [Chemical formula 15]

[0208]

[0209] Where, L 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom or a C1-C4 alkylcarbonyloxy group (such as an acetoxy group), and L 2 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a C1-C4 alkylsulfonyloxy group (e.g., a methanesulfonyloxy group, etc.), a halogenated sulfonyloxy group (e.g., a fluorosulfonyloxy group, etc.), a C1-C4 halogenated alkylsulfonyloxy group (e.g., a trifluoromethanesulfonyloxy group, etc.), or an arylsulfonyloxy group (e.g., a p-toluenesulfonyloxy group, etc.), and G, T, R X , R Y , R 2 , R 3 , R 4 , R a , R e , R f The meanings of and p are the same as above.

[0210] Compound (14) or Compound (15) can be produced by reacting Compound (13) of the present invention with Compound (E) or Compound (F) in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0211] The amount of the compound (E) or compound (F) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (13).

[0212] Some of the compounds represented by compound (E) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (E) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0213] Some of the compounds represented by compound (F) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (F) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0214] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0215] Examples of the base that can be used in the reaction include the bases listed in Production Example 1. The base can be used in an amount of 0.1 to 100 equivalents relative to 1 equivalent of Compound (13).

[0216] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0217] Compound (13) can be synthesized according to the method of Preparation Example 1.

[0218] The compound (1-1) used in Production Example 1 can be produced, for example, according to the production route (reaction route) shown in the following reaction formula 1.

[0219] [Reaction 1]

[0220] [Chemical formula 16]

[0221]

[0222] In the formula, X represents a halogen atom, G, T, R X and R Y The meaning of representative is the same as above.

[0223] Compound (1-1) can be obtained by reacting compound (1-2) with compound (A) in a solvent or in the absence of a solvent and in the presence of a base and optionally in the presence of a copper catalyst and an additive or both. Alternatively, compound (1-1) can be obtained by reacting compound (1-2) with compound (A) in the presence of a base and optionally in the presence of a palladium catalyst and a ligand.

[0224] Some of the compounds represented by compound (1-2) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (1-2) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0225] The amount of the compound (A) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (1-2).

[0226] Some of the compounds represented by compound (A) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (A) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0227] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0228] This reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases listed in Preparation Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-2).

[0229] The reaction can be carried out in the presence of a copper catalyst. Examples of the copper catalyst that can be used include copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, and copper trifluoromethanesulfonate (monovalent) toluene complex. The amount of the copper catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (1-2).

[0230] The reaction may be carried out in the presence of an additive. Examples of the additive include N,N-dimethylglycine and 4-(dimethylamino)pyridine. The amount of the additive used may be 0.001 to 100 equivalents relative to 1 equivalent of compound (1-2).

[0231] The reaction can be carried out in the presence of a palladium catalyst. Examples of palladium catalysts that can be used include (π-cinnamyl)palladium chloride (divalent) dimer and allylpalladium chloride (divalent) dimer. The amount of the palladium catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (1-2).

[0232] The reaction can be carried out in the presence of a ligand. Examples of the ligand that can be used include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (i.e., tert-butyl-XPhos), tetramethyldi-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (i.e., tetramethyldi-tert-butyl-XPhos), 2-di-tert-butylphosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (i.e., RockPhos), or 2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (i.e., BrettPhos). The amount of the ligand used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (1-2).

[0233] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0234] In the compound (1-1), T is an oxygen atom and R Y When the compound (1-1-1) is a hydrogen atom, it can be produced, for example, according to the production route (reaction route) represented by the following reaction formula.

[0235] [Reaction 2]

[0236] [Chemical formula 17]

[0237]

[0238] In the formula, R 101 Represents C1-C6 alkyl, G and R X The meaning of representative is the same as above.

[0239] Step 1: Compound (1-3) can be obtained by reacting compound (1-4) with compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate, etc.) in a solvent or in the absence of a solvent and optionally in the presence of a base.

[0240] Some of the compounds represented by compound (B) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (B) other than commercial products may also be produced according to the synthesis methods of generally known compounds described in the literature.

[0241] The amount of the compound (B) or a salt thereof to be used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (1-4).

[0242] Some of the compounds represented by compound (1-4) can be known compounds recorded in Bioorganic & Medicinal Chemistry Letters, 2015, Vol. 25, p. 4481. In addition, compounds other than those represented by compound (1-4) can also be synthesized in the same manner as known compounds according to the method described in the document.

[0243] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0244] This reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases listed in Preparation Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-4).

[0245] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0246] Step 2: Compound (1-1-1) can also be obtained by reacting compound (1-3) with an oxidizing agent in a solvent or in the absence of a solvent.

[0247] Examples of the oxidizing agent that can be used include potassium permanganate, etc. The amount of the oxidizing agent used may be 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-3).

[0248] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0249] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0250] In the compound (1-1), T is an oxygen atom and R Y When the compound (1-1-1) is a hydrogen atom, it can also be produced, for example, according to the production route (reaction route) represented by the following reaction formula.

[0251] [Reaction 3]

[0252] [Chemical formula 18]

[0253]

[0254] In the formula, G and R X The meaning of representative is the same as above.

[0255] Step 1: By reacting compound (1-6) under the same conditions as in the corresponding step 1 of reaction formula 2, compound (1-5) can be obtained.

[0256] Some of the compounds represented by compound (1-6) may be known compounds described in International Publication No. 2003 / 016275. Other compounds represented by compound (1-6) may be synthesized in the same manner as known compounds according to the method described in the document.

[0257] Step 2: Compound (1-1-1) can also be obtained by reacting compound (1-5) with carbon dioxide in a solvent or in the absence of a solvent and in the presence of a base.

[0258] Examples of the base that can be used include n-butyllithium, etc. The base can be used in an amount of 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-5).

[0259] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0260] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0261] In the range of the compound (1-a) or a salt thereof (such as hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate) used in Production Example 1, R a For R a The compound (1-a') in the case of -1 can be produced, for example, according to the production route (reaction route) shown in the following reaction formula 4.

[0262] [Reaction 4]

[0263] [Chemical formula 19]

[0264]

[0265] In the formula, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , Z, p and r 1 The meaning of representative is the same as above.

[0266] Step 1: Compound (1-a'-2) can be produced by reacting Compound (1-a'-1) with Compound (C1) or Compound (C2) in a solvent or without a solvent and optionally in the presence of a base and, if necessary, in the presence of a phase transfer catalyst.

[0267] Some of the compounds represented by compound (1-a'-1) may be known compounds and may be commercially available. In addition, compounds represented by compound (1-a'-1) other than commercially available products may also be produced by synthetic methods of generally known compounds described in literature.

[0268] Some of the compounds represented by compound (C1) or compound (C2) may be known compounds and may be obtained from commercial products. In addition, compounds represented by compound (C1) or compound (C2) other than commercial products may also be produced by synthetic methods of generally known compounds described in literature.

[0269] The amount of the compound (C1) or the compound (C2) used may be 0.5 to 50 equivalents relative to 1 equivalent of the compound (1-a′-1).

[0270] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0271] This reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases listed in Preparation Example 1. The amount of the base used can be 0.1 to 100 equivalents based on 1 equivalent of Compound (1-a'-1).

[0272] The reaction can be carried out in the presence of a phase transfer catalyst. Examples of the phase transfer catalyst that can be used include quaternary ammonium salts such as tetrabutylammonium bromide. The amount of the phase transfer catalyst used can be 0.001 to 10 equivalents relative to 1 equivalent of compound (1-a'-1).

[0273] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0274] Step 2: Compound (1-a') or a salt thereof (eg, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate) can be prepared by reacting compound (1-a'-2) with an acid in a solvent or in the absence of a solvent.

[0275] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0276] This reaction can be carried out in the presence of an acid. Examples of the acid that can be used include hydrochloric acid, sulfuric acid, acetic acid, and trifluoroacetic acid. The amount of the acid used can be 0.5 to 1000 equivalents relative to 1 equivalent of compound (1-a'-2).

[0277] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0278] The compound (2-1) used in Production Example 2 can be produced, for example, according to the production route (reaction route) shown in the following reaction formula 5.

[0279] [Reaction 5]

[0280] [Chemical formula 20]

[0281]

[0282] In the formula, G, T, R Y , R 1 , R 2 , R 3 , R 4 , R a, Z and p have the same meanings as mentioned above.

[0283] Compound (2-1) can be produced by reacting compound (3) of the present invention with an acid in a solvent or in the absence of a solvent.

[0284] If a solvent is used, the solvent used may be inert to the reaction, and examples of the solvent include the solvents listed in Production Example 1.

[0285] Examples of the acid that can be used in the reaction include hydrochloric acid, sulfuric acid, formic acid, trifluoroacetic acid, etc. The amount of the acid used can be 0.1 to 100 equivalents relative to 1 equivalent of Compound (3).

[0286] The reaction temperature and reaction time can be arbitrarily set within the temperature range and time range described in Preparation Example 1.

[0287] Compound (3) can be synthesized according to the method of Production Method 1.

[0288] The compounds of the present invention can be generally used as agricultural and horticultural fungicides / fungicides to combat various diseases caused by protoplasmic molds, oomycetes, mucors, ascomycetes, basidiomycetes, deuteromycetes, bacteria or viruses.

[0289] The "pathogen" refers to a microorganism that is a pathogen of a plant disease, and specific examples thereof include the following microorganisms, but the present invention is not limited thereto.

[0290] Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercosporaspp. (e.g., Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g., Cladosporium colocasiae, C. cucumerinum, C. variabile, etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g. Heterosporium allii, etc.), Mycosphaerella spp. (e.g. Mycosphaerella arachidis, M.berkeleyi, M.cerasella, M.fijiensis, M.fragariae, M.graminicola, M.nawae, M.pinodes, M.pomi, M.zingiberis, etc.), Mycovellosiella spp. (e.g. Mycovellosiella fulva, M.nattrassii, etc.), Paracercospora spp. (e.g. Paracercospora egenula, etc.), Phaeosariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g. Pseudocercospora abelmoschi, P.fuligena, P.vitis, etc.), Pseudocercosporella spp. (e.g. Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (such as Septoria albopunctata, S.apiicola, S.chrysanthemella, S.helianthi, S.obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoespp. (e.g. Elsinoe ampelina, E.araliae, E.fawcettii, etc.), Sphaceloma spp. (e.g. Sphaceloma caricae, etc.), Ascochyta spp. (e.g. Ascochyta pisi, etc.), Corynespora spp. (e.g. Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g. Leptosphaeriaconiothyrium, L.maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g. Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp. (e.g. Pyrenophoragraminea, P.teres, etc.), Setosphaeria spp. (e.g. Setosphaeria turcica, etc.), Stemphylium spp.(e.g. Stemphylium botryosum, S. lycopersici, S. solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (e.g. Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. (e.g. Didymella bryoniae, D. fabae, etc.), Hendersonia spp., Phoma spp. (e.g. Phoma erratica var. mikan, P. exigua var. exigua, P. wasabiae, etc.), Pyrenochaeta spp. (e.g. Pyrenochaeta lycopersici, etc.), Stagonospora spp. (e.g. Stagonospora sacchari, etc.), Botryosphaeria spp. (e.g. Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (e.g., Lasiodiplodia theobromae, etc.), Macrophoma spp., Macrophomina spp., Neofusicoccum spp., Phyllosticta spp. (e.g., Phyllostictazingiberis, etc.), Schizothyrium spp. (e.g., Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (e.g., Penicilliumdigitatum, P.italicum, P.sclerotigenum, etc.), Microsporum spp., Trichophyton spp. (e.g., Trichophyton mentagrophytes, T.rubrum, etc.), Histoplasma spp., Blumeria spp. (e.g., Blumeria graminis f.sp.hordei, Bgfsp.tritici, etc.), Erysiphe spp.(e.g. Erysiphebetae, E.

[0291] cichoracearum, Ec var. cichoracearum, E. heraclei, E. pisi, etc.), Golovinomyces spp. (e.g. Golovinomyces cichoracearum var. latisporus, etc.), Leveillula spp. (e.g. Leveillula taurica, etc.), Microsphaera spp., Oidium spp. (e.g. Oidium neolycopersici, etc.), Phyllactinia spp. (e.g. Phyllactinia kakicola, P. mali, P. moricola, etc.), Podosphaera spp. (e.g. Podosphaera fusca, P. leucotricha, P. pannosa, P. tridactyla var. tridactyla, P. xanthii, etc.), Sphaerotheca spp. (e.g. Sphaerotheca aphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (e.g. Uncinula necator, Unvar.necator, etc.), Uncinuliella spp. (e.g. Uncinuliella simulans var.simulans, Usvar.tandae, etc.), Blumeriella spp. (e.g. Blumeriella jaapii, etc.), Cylindrosporium spp., Diplocarpon spp. (e.g. Diplocarpon mali, D.mespili, D.rosae, etc.), Gloeosporium spp. (e.g. Gloeosporium minus, etc.), Marssonina spp., Tapesia spp. (e.g. Tapesiaacuformis, T.yallundae, etc.), Lachnum spp., Scleromitrula spp., Botryotinia spp. (e.g. Botryotinia fuckeliana, etc.), Botrytis spp. (e.g. Botrytis allii, B.byssoidea, B.cinerea, B.elliptica, B.fabae, B.squamosa, etc.), Ciborinia spp., Grovesinia spp.、 Monilia mumecola、Monilinia spp. sorghum、C.sorghicola etc.)、Epichloespp.、Ephelis japonica、Villosiclava virens、Hypomyces spp.(eg Hypomyces solanif.sp.mori、Hsfsp.pisi etc.)、Trichoderma spp.(eg Trichoderma viride etc.)、Calonectria spp.(eg Calonectria ilicicola etc.) spp. (e.g. Fusariumarthrosporioides, F.crookwellense, F.culmorum, F.cuneirostrum, F.oxysporum, Fofsp.adzukicola, Fofsp.allii, Fofsp.asparagi, Fofsp.batatas, Fofsp.cepae, Fofsp.colocasiae, Fofsp.conglutinans, Fofsp.cubense, Fofsp.cucumerinum, Fofsp.fabae, Fofsp.fragariae, Fofsp.lactucae, Fofsp.lagenariae, Fofsp.lycopersici, Fofsp.melongenae, Fofsp.melonis, Fofsp.nelumbinicola, Fofsp.niveum, Fofsp.radicis-lycopersici, Fofsp.raphani, F.ofsp.spinaciae, F.sporotrichioides, F.solani, Fsfsp.cucurbitae, Fsfsp.eumartii, Fsfsp.glycines, Fsfsp.pisi, Fsfsp.Radicicola, F.virguliforme, etc.), Gibberella spp. (such as Gibberellaavenacea, G.baccata, G.fujikuroi, G.zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (such as Verticillium albo-atrum, V.dahliae, V.longisporum, etc.), Ceratocystis spp. (such as Ceratocystis ficicola, C.fimbriata, etc.), Thielaviopsis spp. (e.g. Thielaviopsis basicola, etc.), Adisciso spp., Monochaetia spp., Pestalotia spp. (e.g. Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (e.g. Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Roselliniia spp. (e.g. Roselliniia necatrix, etc.), Monographella spp. (e.g. Monographella nivalis, etc.), Ophiostoma spp., Cryphonectria spp. (e.g. Cryphonectria parasitica, etc.), Diaporthe spp. (e.g. Diaporthe citri, D. kyushuensis, D. nomurai, D. tanakae, etc.), Diaporthopsis spp., Phomopsis spp. (e.g. Phomopsisasparagi, P.fukushii, P.obscurans, P.vexans, etc.), Cryptosporella spp., Discula spp. (e.g., Discula theae-sinensis, etc.), Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp. (e.g., Valsa ceratosperma, etc.), Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp. (e.g., Gaeumannomyces graminis, etc.), Magnaporthe spp. (e.g., Magnaporthe grisea, etc.), Pyricularia spp. (e.g., Pyricularia zingiberis, etc.), Monilochaetes infuscans, Colletotrichum spp. (e.g., Colletotrichum acutatum, C.capsici, C.cereale, C.destructivum, C.fragariae, C.lindemuthianum, C.nigrum, C.orbiculare, C.spinaciae, etc.), Glomerella spp. (e.g. Glomerella cingulata, etc.), Khuskia oryzae, Phyllachora spp. (e.g. Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g. Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g. Peltasterfructicola, etc.), Phaeocytostroma spp., Phialophora spp. (e.g. Phialophora gregata, etc.), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp.Ascomycota fungi such as Rhynchosporium secalis, Sarocladium spp., Coleophoma spp., and Helicocerasoryzae. Septobasidium spp. (e.g. Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g. Helicobasidium longisporum, etc.), Coleosporium spp. (e.g. Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. (e.g. Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.), Physopella spp. (e.g. Physopella ampelopsidis, etc.), Kuehneola spp. (e.g. Kuehneola japonica, etc.), Phragmidium spp. (e.g. Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, etc.), Gymnosporangium spp. (e.g. Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (e.g. Puccinia allii, P.brachypodii var.poae-nemoralis, P.coronata, Pcvar.coronata, P.cynodontis, P.graminis, Pgsubsp.graminicola, P.hordei, P.horiana, P.kuehnii, P.melanocephala, P.recondita, P.striiformisvar.striiformis, P.tanaceti var.tanaceti, P.tokyensis, P.zoysiae, etc.), Uromycesspp. (such as Uromyces phaseoli var.azukicola, Upvar.phaseoli, Uromyces viciae-fabae var.viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucoteliumspp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. (e.g., Ustilago maydis, U. nuda, etc.), Entyloma spp., Exobasidium spp. (e.g., Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. (e.g., Tilletia caries, T. contesta, T. laevis, etc.), Itersonilia spp. (e.g., Itersonilia perplexans, etc.), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha, etc.), Lycoperdon spp. (e.g. Lycoperdon curtisii, L.perlatum, etc.), Conocybe spp. (e.g. Conocybe apala, etc.), Marasmius spp. (e.g. Marasmius oreades, etc.), Armillaria spp., Helotium spp., Lepistaspp. (e.g. Lepista subnuda, etc.), Sclerotium spp. (e.g. Sclerotium cepivorum, etc.), Typhula spp. (e.g. Typhula incarnata, T.ishikariensis var.ishikariensis, etc.), Athelia spp. (e.g. Athelia rolfsii, etc.), Ceratobasidium spp. (e.g. Ceratobasidiumcornigerum, etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g. Rhizoctonia solani, etc.), Thanatephorus spp. (such as Thanatephorus cucumeris, etc.), Laetisaria spp., Waiteaspp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaetespp., etc., Basidiomycota fungi. Olpidium spp., etc., Chitridiomycota fungi. Physoderma spp., etc., Blastocladiomycota fungi. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer, etc., etc., Mucoromycotina fungi. Protists of the phylum Cercozoa, such as Plasmodiophora spp. (e.g. Plasmodiophora brassicae, etc.) and Spongospora subterranea f.sp.Subterranea. Aphanomyces spp. (e.g. Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g. Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g. Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (e.g. Peronospora alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosaf. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g. Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g. Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (e.g. Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P.cryptogea, P.fragariae, P.infestans, P.melonis, P.nicotianae, P.palmivora, P.porri, P.sojae, P.syringae, P.vignae f.sp.adzukicola, etc.), Pythium spp. (such as Pythium afertile, P.aphanidermatum, P.apleroticum, P.aristosporum, P.arrhenomanes, P.buismaniae, P.debaryanum, P.graminicola, P.horinouchiense, P.ir regulare, P.iwayamai, P.myriotylum, P.okanoganense, P.paddicum, P.paroecandrum, P.periplocum, P.spinosum, P.sulcatum, P.sylvaticum, P.ultimum var.ultimum, P.vanterpoolii, P.vexans, P.volutum, etc.) of the phylum Heterokontophyta. Gram-positive bacteria of the phylum Actinobacteria, such as Clavibacter spp. (e.g. Clavibacter michiganensis subsp.michiganensis, etc.), Curtobacterium spp., Leifsonia spp. (e.g. Leifsonia xyli subsp.xyli, etc.), Streptomyces spp. (e.g. Streptomyces ipomoeae, etc.). Gram-positive bacteria of the phylum Firmicutes, such as Clostridium sp.. Gram-positive bacteria of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g. Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g. Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g. Acidovorax avenae subsp. avenae, Aa subsp. citrulli, A.konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (such as Ralstonia solanacearum, etc.), Xanthomonasspp. (such as Xanthomonas albilineans, X.arboricola pv.pruni, X.axonopodispv.vitians, pv.campestris, Xcpv.cucurbitae, Xcpv.glycines, Xcpv.mangiferaeindicae, Xcpv.nigromaculans, cichorii, P.fluorescens, P.marginalis, Pmpv.marginalis, P.savastanoi pv.glycinea, P.syringae, Pspv.actinidiae, Pspv.eriobotryae, Pspv.helianthi, Pspv.lachrymans, Pspv.maculicola, Psp v.mori, Pspv.morsprunorum, Pspv.spinaciae, Pspv.syringae, Pspv.theae, P.viridiflava, etc.), Rhizobacterspp., Brenneria spp. (such as Brenneria nigrifluens, etc.), Dickeya spp. (such as Dickeyadianthicola, D.zeae, etc.), Erwinia spp. (such as Erwinia amylovora, E.rhapontici, etc.), Pantoea spp., Pectobacterium spp. (such as Pectobacterium atrosepticum, P.carotovorum, P.wasabiae, etc.) and other Gram-negative bacteria of the Proteobacteria.

[0292] Specific examples of plant diseases caused by infection and proliferation of these pathogens include the following plant diseases, but are not limited to these.

[0293] Peach Leaf curl (Taphrina deformans), Plum pockets (Taphrinapruni), Asparagus Leaf spot (Cercospora asparagi), Beet leaf spot (Cercospora beticola), Green pepper Frogeye leaf spot (Cercospora capsici), Persimmon Angular leaf spot (Cercospora kaki), Soybean Purple stain (Cercospora kikuchii), Peanut Brown Leaf spot

[0294] spot(Mycosphaerella arachidis), cherry brown spot disease Cylindrosporium leaf

[0295] spot (Mycosphaerella cerasella, Blumeriella jaapii), Black tobacco disease

[0296] sigatoka (Mycosphaerella fijiensis), Yellow sigatoka (Mycosphaerell musicola), Speckled leaf blotch (Mycosphaerella graminicola), Circular leaf spot (Mycosphaerella nawae), Mycosphaerella blight (Mycosphaerella pinodes), Leaf spot (Mycosphaerella zingiberis), Leaf mold (Mycovellosiella fulva), Leaf mold (Mycovellosiella nattrassii), Cercospora leaf mold (Pseudocercospora fuligena), Isariopsis leaf spot (Pseudocercosporavitis), White cabbage leaf spot (Pseudocercosporella capsellae), Chrysanthemum leaf spot spot(Septoria chrysanthemella), Leaf blight(Septoria obesa), Anthracnose(Elsinoe ampelina), Spot anthracnose(Elsinoe araliae), Scab(Elsinoe fawcettii), Leaf spot(Ascochyta pisi), Corynespora leaf spot(Corynespora cassiicola), Stem canker(Leptosphaeria coniothyrium), Glume blotch(Leptosphaeria nodorum), Leaf spot(Alternaria alternata), Alternaria leaf spot(Alternaria brassicae), Leaf blight(Alternaria dauci), Black spot(Alternaria cassiicola),kikuchiana), Alternaria blotch (Alternariamali) of apple, Alternaria leaf spot (Alternaria porri) of onion, Target spot (Bipolaris sorghicola) of sorghum, Southern leaf blight (Cochliobolus heterostrophus) of corn, Brown spot (Cochliobolus miyabeanus) of rice, Tip blight (Pleospora herbarum) of garlic, Stripe (Pyrenophora graminea) of barley, Net blotch (Pyrenophora teres) of barley, Leaf blight (Setosphaeria turcica) of sorghum, Northern leaf blight (Setosphaeria turcica) of corn, Leaf spot (Stemphylium botryosum) of asparagus, Scab (Venturia carpophila) of Rosaceae, Scab (Venturia Inaequalis), Scab (Venturia nashicola), Gummystem blight (Didymella bryoniae), Leaf spot (Phoma exigua var. exigua), Streak (Phoma wasabiae), Ring (Pomyceae subfamily)

[0297] rot(Botryosphaeria berengeriana f.sp.piricola), kiwifruit soft rot

[0298] rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Common green mold (Penicillium digitatum), Blue mold (Penicillium italicum), Powdery mildew on various crops, Blumeria graminis f.sp.hordei, Blumeria graminis f.sp.tritici, Cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), Eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), Carrot / parsley powdery mildew (Erysiphe heraclei), Pea powdery mildew (Erysiphe pisi), Tomato powdery mildew (Leveillula taurica, Oidium sp., Podosphaera xanthii), neolycopersici, Oidium sp.), green pepper powdery mildew (Leveillulataurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter gourd powdery mildew (Oidium sp.), persimmon powdery mildew (Phyllactinia kakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha), rose powdery mildew (Podosphaera pannosa, Uncinuliellasimulans var.simulans, Usvar.tandae), papaya / melon powdery mildew (Podosphaera xanthii), strawberry powdery mildew (Sphaerotheca aphanis var.aphanis), watermelon / honeydew powdery mildew (Sphaerothecafuliginea), grape powdery mildew (Uncinula necator, Unvar.necator), Blotch (Diplocarpon mali), Black spot (Diplocarpon rosae), Gray mold neck rot (Botrytis allii), Gray mold, Botrytis blight (Botrytis cinerea), Leaf blight (Botrytis cinerea, B.byssoidea, B.squamosa), Chocolate spot (Botrytis cinerea, B.elliptica, B.fabae), Brown rot (Monilinia fructicola, M.fructigena, M.laxa), Blossom blight (Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Cottonyrot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False rot smut (Villosiclava virens), soybean black root necrosis (Calonectria ilicicola), wheat red mold Fusarium blight (Fusarium crookwellense, F.culmorum, Gibberella avenacea, G.zeae, Monographella nivalis), barley red mold Fusarium blight (Fusarium culmorum, Gibberella avenacea, G.zeae), konjac dry rot (Fusarium oxysporum, F.solanif.sp.radicicola), yam brown rot (Fusarium oxysporum, F.solani f.sp.pisi, Fsfsp.radicicola), red bean wilt Fusarium oxysporumf.sp.adzukicola), radish dry rot Fusarium basal rot (Fusarium oxysporum f.sp.allii,F.solani f.sp.radicicola), sweet potato vine rot (Fusarium oxysporum f.sp.batatas, F.solani), taro dry rot (Fusarium oxysporum f.sp.colocasiae), cabbage / komatsuna yellow wilt (Fusarium oxysporum f.sp.conglutinans), rubber Panama disease (Fusarium oxysporum f.sp.cubense), strawberry wilt (Fusarium oxysporum f.sp.fragariae), lettuce root rot (Fusarium oxysporumf.sp.lactucae), watermelon vine rot (Fusarium oxysporum f.sp.lagenariae, Fofsp.niveum), tomato wilt (Fusarium oxysporum f.sp.niveum), oxysporumf.sp.lycopersici), melon vine rot Fusarium wilt (Fusarium oxysporum f.sp.melonis), radish yellow wilt Yellows (Fusarium oxysporum f.sp.raphani), spinach wilt Fusarium wilt (Fusarium oxysporum f.sp.spinaciae), soybean acute death syndrome (Fusarium solani f.sp.Glycines, Fusarium virguliforme), rice seedling disease "Bakanae" disease (Gibberella fujikuroi), radish black spot disease Verticillium black spot (Verticilliumalbo-atrum, V.dahliae), tomato, eggplant, bean wilt Verticillium wilt (Verticilliumdahliae), fig stem blight Ceratocystis canker (Ceratocystis ficicola), sweet potato black spot (Ceratocystis fimbriata), tea ring spot (Pestalotiopsis longiseta, P.theae), Endothia canker (Cryphonectria parasitica), Melanose (Diaporthe citri), Stem blight (Phomopsis asparagi), Phomopsis canker (Phomopsis fukushii), Brown spot (Phomopsis vexans), Anthracnose (Discula theae-sinensis), Valsa canker (Valsaceratosperma), Blast (Magnaporthe grisea), Crown rot (Colletotrichum acutatum, C.fragariae, Glomerella cingulata), Bitterrot (Colletotrichum acutatum, Glomerella cingulata), Cherry Anthracnose (Colletotrichum acutatum, Glomerella cingulata), Peach Anthracnose (Colletotrichum acutatum), Ripe rot (Colletotrichum acutatum, Glomerella cingulata), Chrysanthemum Anthracnose (Colletotrichum acutatum), Bean Anthracnose (Colletotrichum lindemuthianum), Cucurbit Anthracnose (Colletotrichum orbiculare), Yam Anthracnose (Glomerella cingulata), Chestnut Anthracnose (Glomerella cingulata), Persimmon Anthracnose (Glomerella cingulata), Red Bean Leaf Fall Disease Brown Stem rot (Phialophora gregata), yam leaf spot (Pseudophloeosporella dioscoreae), barley scald (Rhynchosporium secalis), wheat brown rust (Puccinia recondita), wheat stripe rust (Puccinia striiformis), rust on various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), pear red star (Gymnosporangium asiaticum), apple red star (Gymnosporangium yamadae), onion rust (Puccinia allii), chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var.tanaceti), bean rust (Uromyces viciae-fabae var.viciae-fabae), sugarcane smut (Sporisorium scitamineum), corn smut (Ustilago maydis), barley loose smut (Ustilago nuda), tea net blisterblight (Exobasidium reticulatum), tea blister blight (Exobasidium vexans), white rot, southern blight (Athelia rolfsii), chrysanthemum stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger wilt (Rhizoctonia solani), cabbage seedling damping-off (Rhizoctonia solani), clover damping-off (Rhizoctonia solani), lettuce bottom rot (Rhizoctonia solani), Brownpatch and Large patch (Rhizoctonia solani), Sheath blight (Thanatephoruscucumeris), Root rot (Thanatephorus cucumeris), Leaf blight (Thanatephorus cucumeris), Rhizopus rot (Rhizopus stolonifervar.stolonifer), Clubroot (Plasmodiophora brassicae), Aphanomyces root rot (Aphanomyces cochlioides), White rust (Albugomacrospora), Downy mildew on various crops, Bremia lactucae, Peronospora chrysanthemi-coronarii), onion / Allium downy mildew (Peronosporadestructor), spinach downy mildew (Peronospora farinosa f.sp.spinaciae), soybean downy mildew (Peronospora manshurica), Brassica napus downy mildew (Peronospora parasitica), rose downy mildew (Peronospora sparsa), sunflower downy mildew (Plasmopara halstedii), clover downy mildew (Plasmopara nivea), grape downy mildew (Plasmopara viticola), cucurbit downy mildew (Pseudoperonospora cubensis), Aralia root rot (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), pumpkin blight (Phytophthora rot) (Phytophthora capsici), green pepper blight (Phytophthora capsici), watermelon blight (Phytophthora cryptogea), tomato / potato late blight (Phytophthora infestans), White powdery rot (Phytophthora palmivora), Leaf blight (Phytophthora porri), Phytophthora root and stem rot (Phytophthora sojae), Phytophthora stem rot (Phytophthora vignaef.sp.adzukicola), Damping-off (Pythium aphanidermatum, P.myriotylum, P.paroecandrum, P.ultimum var.ultimum), Root rot (Pythiumaristosporum), Browning root rot (Pythium arrhenomanes, P.graminicola), Damping-off (Pythium buismaniae, P.myriotylum), Root rot (Pythium myriotylum), Root rot (Pythiummyriotylum, P.ultimum var.ultimum), Brown blotted root rot (Pythiumsulcatum), Bacterial canker (Clavibacter michiganensissubsp.michiganensis), Scab (Streptomyces spp.), Crowngall (Rhizobium radiobacter), Bacterial stripe (Burkholderiaandropogonis), Soft rot (Burkholderia cepacia, Pseudomonas marginalispv.marginalis, Erwinia rhapontici), Bacterial grain rot (Burkholderiagladioli, B.glumae), Bacterial fruit blotch (Acidovorax avenaesubsp.citrulli), Bacterial leaf blotch (Acidovorax avenaesubsp.citrulli), leafblight (Acidovorax konjaci), Bacterial wilt (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv.pruni, Pseudomonas syringae pv.syringae, Brennerianigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv.pruni), Bacterial spot (Xanthomonas axonopodis pv.vitians), Black rot (Xanthomonas campestris pv.campestris), Bacterial pustule (Xanthomonas campestris pv.glycines), Bacterial spot (Xanthomonascampestris pv.nigromaculans), Bacterial spot (Xanthomonascampestris pv.nigromaculans) of green pepper spot(Xanthomonascampestris pv.vesicatoria), Citrus canker (Xanthomonas citrisubsp.citri), Garlic spring rot (Pseudomonas cichorii, P.marginalis pv.marginalis, Erwinia sp.), Lettuce rot (Pseudomonas cichorii, P.marginalis pv.marginalis, P.viridiflava), Kiwi blossom blight (Pseudomonas marginalis pv.marginalis, P.syringae pv.syringae, P.viridiflava), Kiwi canker (Pseudomonas syringae pv.actinidiae), Loquat tuber.

[0299] Canker (Pseudomonas syringae pv.eriobotryae), Bacterial spot (Pseudomonas syringae pv.lachrymans) of Cucurbitaceae, Bacterial black spot (Pseudomonas syringae pv.maculicola) of Brassica napus, Bacterial canker (Pseudomonassyringae pv.morsprunorum, Erwinia sp.) of Plum canker, Bacterial shoot blight (Pseudomonas syringae pv.theae) of Tea, Bacterial soft rot (Dickeya sp., Pectobacterium carotovorum) of Alliumaceae, Fire blight (Erwinia amylovora) of Rosaceae, Soft rot (Pectobacterium carotovorum) of Konjac, Bacterial soft rot (Pectobacterium carotovorum).

[0300] The development of pest control agents for agricultural and horticultural crop diseases has been fruitful, and a wide variety of agents have been provided in practice so far. However, due to the long-term use of these agents, in recent years, there has been an increase in the number of pathogens that have acquired resistance to the agents and are difficult to control with the existing fungicides used in the past. In addition, some existing agents are highly toxic, and the problem of some agents remaining in the environment for a long time and disrupting the ecosystem has gradually emerged. In this case, the compounds of the present invention have excellent pest control activity against many pathogens and are highly safe for target crops. In addition, the compounds of the present invention can also exert a sufficient pest control effect on pathogens that have acquired resistance to existing fungicides. In addition, the compounds of the present invention will not cause phytotoxicity to target crops, have almost no adverse effects on mammals, fish and beneficial insects, and have low residue and low environmental load.

[0301] In addition to being useful as agricultural and horticultural fungicides, the compounds of the present invention can also be used as: medical antimicrobial agents and animal antimicrobial agents used as antifungal agents or internal parasite control agents; antibacterial / mildewproof agents for wood, paper / pulp, adhesives / coatings, fibers and leather, etc.; and industrial fungicides for cooling water lines in manufacturing plants, etc.

[0302] Regarding the target pathogens of medical antimicrobial agents or animal antimicrobial agents, for example, Trichophyton rubrum and Trichophyton mentagrophytes, Candida such as Candida albicans, Aspergillus such as Aspergillus fumigatus, Cryptococcus such as Cryptococcus neoformas, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae, Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes, etc. can be mentioned, but are not limited to these.

[0303] Regarding the target strains of antibacterial / antifungal agents, for example, wood decay fungi such as Tyromyces palustris and Coriolus versicolor, and material deterioration microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria can be listed, but are not limited to these.

[0304] Examples of target bacterial strains for industrial fungicides include, but are not limited to, Sphaerotilis natans, Zoogloearamigera and other mycete fungi.

[0305] The compound of the present invention can be used as an agricultural and horticultural fungicide and also as an internal parasite control agent for livestock, poultry or pets.

[0306] The following specific examples are given as the internal parasites to be controlled, but the examples are not limited thereto.

[0307] Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Storongylus, Trichonema, Dictyocaulus, Capillaria, Heterak is), Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, etc.; Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, Loa, etc.; Dracunculidae nematodes such as Deacunculus, etc.; Dipylidium caninum), Taeniataeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus, Echinococcus multilocularis, etc.; Fasciola hepatica (F.gigantica), Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum (E.coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni, etc.; Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria ovinoidalis; Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesia spp.), Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., etc.

[0308] The compounds of the present invention can be used as agricultural and horticultural fungicides as well as antifungal agents.

[0309] The target pathogens of the antifungal agents include the following specific examples, but are not limited thereto.

[0310] Trichophyton rubrum, Trichophyton mentagrophytes, etc., Candida albicans, etc., Aspergillus fumigatus, etc., Cryptococcus, etc.

[0311] When the compound of the present invention is applied as a plant disease control agent and a plant pest control agent, the compound of the present invention can be generally mixed with a suitable solid or liquid carrier, and a surfactant, a penetrant, a spreading agent, a thickener, an antifreeze agent, an adhesive, an anti-caking agent, a disintegrator or an anti-decomposition agent can be added as needed to prepare a liquid (soluble concentrate), an emulsion (emulsifiable concentrate), a wettable powder (wettable powder), a water-soluble powder (water soluble powder), a water dispersible granule (water dispersible granule), a water-soluble granule (water soluble granule), a suspension (suspension concentrate), an emulsion (concentrated emulsion), a suspoemulsion (suspoemulsion), a microemulsion (microemulsion), a dustable powder, a granule (granule) or a gel (gel) and other arbitrary dosage forms for practical use. In addition, from the viewpoint of labor saving and improving safety, the preparation of any dosage form described above can also be provided by sealing in a water-soluble packaging body.

[0312] Examples of the solid carrier include natural minerals such as quartz, kaolin, pyrophyllite, diatomaceous earth, talc, bentonite, acid clay, attapulgite, zeolite or diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate or potassium chloride; synthetic silicic acid; or synthetic silicates.

[0313] Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol, or isopropanol; aromatic hydrocarbons such as xylene, alkylbenzenes, or alkylnaphthalene; ethers such as butyl glycol monoethyl ether (trade name: Cellosolve); ketones such as cyclohexanone; esters such as γ-butyrolactone; amides such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, or castor oil; or water, etc. These solid and liquid carriers may be used alone or in combination of two or more.

[0314] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, or polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formaldehyde condensates of naphthalenesulfonic acid, salts of formaldehyde condensates of alkylnaphthalenesulfonic acid, sulfates or phosphates of polyoxyethylene alkyl aryl ethers, sulfates or phosphates of polyoxyethylene styryl phenyl ethers, polycarboxylates, or polystyrene sulfonates; cationic surfactants such as alkylamine salts or alkyl quaternary ammonium salts; amino acid type or amine inner salt type amphoteric surfactants; and the like.

[0315] The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight based on 100 parts by weight of the preparation of the present invention. In addition, these surfactants may be used alone or in combination of two or more.

[0316] When the compound of the present invention is used as a pesticide, it can be mixed with other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers or soil conditioners during formulation or spraying, if necessary.

[0317] In particular, by mixing with other pesticides or plant hormones, it is expected that the cost reduction brought by the small amount of application, the broad-spectrum fungicide and insecticide effect brought by the synergistic effect of the mixed agents, or the higher pest control effect can be expected. When mixed, it can also be combined with multiple known pesticides at the same time.

[0318] In one embodiment, the types of pesticides mixed with the compounds of the present invention include, for example, compounds described in the 18th edition of "The Pesticide Manual" in 2018. The specific common names of these compounds can be exemplified as follows. However, the pesticides mixed are not limited to these.

[0319] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide polysulfide), benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, BENZAMACRIL, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, bordeaux mixture mixture), boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate,climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate zincchromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetic acid acid, dichlobentiazox, dichlofluanid, dichlone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dim ethirimol), dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbon, diphenylamine, dipymetitrone,Dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimo l), ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpyram ... coxamid), fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet,Fosetyl-aluminium, fthalide, fuberidazole, furaxyl, furametpyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachloride, Hexachlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinolinesulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodopropynyl butylcarbamate b), ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamid, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin ), kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxyl,metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, methfuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, sodium (nabam), naftifine, natamycin, organonic nickel compounds (nickel bis(dimethyldithiocarbamate); nickel bis(dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, 8-hydroxyquinoline copper (oxine copper), oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb,proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid, pyridachlometyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium bicarbonate hydrogen carbonate), sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil,tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc cyclohexane naphthenate), zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract and shiitake fruiting body extract, etc.

[0320] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, BENZPYRIMOXAN, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, but ocarboxim), carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, CHLORETHXYFOS, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide,clofentezine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin, cyhexatine, Cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, diclomezotiaz, dicofol, dienochlor, diflovidazin, diflubenzuron on), dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC, d-tetramethrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon on-metofluthrin), epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatinoxide, fenitrothion, FENMEZODITIAZ, fenobucarb,Fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlorodiniliprole, flucyclopentyl xuron), flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin, fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazole azapyroxamet), indoxacarb, indoxacarb-MP, isocycloseram, isofenphos-methyl, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, lepimectin, lufenuron, malathion,meperfluthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide bromide), metofluthrin, milbemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, chlorpyrifos, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, PRAZIQUANTEL, profenofos, profluthrin, propaphos, propargite, prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfen,resmethrin, rotenone, silafluofen, spidoxamat, spinetoram, spinosad, spirodiclofen, spiromesifen, spiropidion, spirotetramat, spyromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos hlorvinphos), tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion and zeta-cypermethrin, etc.

[0321] Antiparasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, cypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid amiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, dimethoate, diazinon), dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, afo afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner, tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin,maduramycin, milbemycin, milbemycin oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, metronidazole, metyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate adipate), piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride,Thiabendazole and triclabendazole, etc.

[0322] Antifungal agents: ketoconazole and miconazole nitrate, etc.

[0323] Antimicrobial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid acid, danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate phosphate), acetylisovaleryl tylosin, tylosin phosphate, tulathromycin, valnemulin, shell calcined calcium (calcium oxide), Tara Rossella, Trichoderma and fungi, etc.

[0324] The dosage of the compound of the present invention varies depending on the application, application period, application method or cultivated crops, but is usually 0.005 to 50 kg, preferably 0.01 to 1 kg, of the active ingredient per hectare (ha).

[0325] The following describes the formulation examples of the compounds of the present invention. However, the formulation examples of the present invention are not limited to these. In addition, in the following formulation examples, "parts" refer to parts by weight.

[0326] 〔Wettable powder〕

[0327]

[0328] Other examples include anti-caking agents and anti-decomposition agents.

[0329] 〔Emulsion〕

[0330]

[0331] Other examples include a spreading agent and an anti-decomposition agent.

[0332] 〔Suspension Concentrate〕

[0333]

[0334] Other examples include antifreeze agents and thickeners.

[0335] 〔Water dispersible granules〕

[0336]

[0337] As other ingredients, for example, there may be mentioned adhesives and anti-decomposition agents.

[0338] 〔Liquid〕

[0339] 0.01 to 70 parts of the compound of the present invention

[0340] Liquid carrier 20~99.99 parts

[0341] Other 0~10

[0342] Other examples include antifreeze agents and spreaders.

[0343] 〔Granules〕

[0344] 0.01 to 80 parts of the compound of the present invention

[0345] Solid carrier 10~99.99 parts

[0346] Other 0~10

[0347] As other ingredients, for example, there may be mentioned adhesives and anti-decomposition agents.

[0348] 〔powder〕

[0349] 0.01 to 30 parts of the compound of the present invention

[0350] Solid carrier 65~99.99 parts

[0351] Other 0~5

[0352] Other examples include drift inhibitors and decomposition inhibitors.

[0353] When used, the above preparation is diluted 1 to 10,000 times, preferably 100 to 10,000 times with water, or spread without dilution.

[0354] The following specifically shows examples of formulations of agricultural and horticultural fungicides using the compound of the present invention as an active ingredient, but the formulation of the present invention and the compound of the present invention are not limited to these examples. In addition, in the following formulation examples, "parts" refer to parts by weight.

[0355] [Preparation Example 1] Emulsion

[0356]

[0357] A mixture of stimulants; a trade name of Toho Chemical Industry Co., Ltd.)

[0358] The above ingredients are uniformly mixed to prepare an emulsion. When used, the emulsion is diluted 50 to 20,000 times with water and spread in a manner such that the average effective ingredient dosage per hectare is 0.005 to 50 kg.

[0359] [Preparation Example 2] Wettable powder

[0360]

[0361]

[0362] The above ingredients are uniformly mixed and crushed to prepare a wettable powder. When used, the wettable powder is diluted 50 to 20,000 times with water and spread in a manner such that the average effective ingredient dosage per hectare is 0.005 to 50 kg.

[0363] [Preparation Example 3] Powder

[0364]

[0365] The above ingredients are uniformly mixed and crushed to prepare a powder. When used, the powder is spread so that the effective ingredient dosage per hectare is 0.005 to 50 kg.

[0366] [Preparation Example 4] Granules

[0367]

[0368] The above ingredients are uniformly mixed and crushed, a small amount of water is added and stirred, granulated with an extrusion granulator, and dried to form granules. When used, the granules are spread in a manner such that the effective ingredient dosage per hectare is 0.005 to 50 kg.

[0369] [Preparation Example 5] Suspension

[0370]

[0371] The above ingredients except the active ingredient (compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred sufficiently, and then wet-pulverized with a sand mill to obtain a flowable agent. When used, the flowable agent is diluted 50 to 20,000 times with water and spread in a manner such that the average active ingredient dosage per hectare is 0.005 to 50 kg.

[0372] [Preparation Example 6] Granular wettable powder

[0373]

[0374] The above ingredients are uniformly mixed and finely pulverized, a small amount of water is added, stirred and mixed, granulated with an extrusion granulator, and dried to form a dry flowable agent. When used, it is diluted 50 to 20,000 times with water and spread in a manner such that the average effective ingredient dosage per hectare is 0.005 to 50 kg.

[0375] The method for applying the compound of the present invention includes foliar spraying, soil treatment, seed disinfection, and the like. However, it is also effective to adopt a general method commonly used by those skilled in the art.

[0376] 〔Summarize〕

[0377] As described above, the present invention relates to the following schemes [1] to

[70] .

[0378] [1] A pyrazole compound represented by the formula (1) or a salt thereof.

[0379] [Chemical formula 21]

[0380]

[0381] In the formula, G represents G-1, and G-1 represents the structure shown in the following structural formula,

[0382] [Chemical formula 22]

[0383]

[0384] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R',

[0385] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0386] R b Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R',

[0387] R represents a hydrogen atom or a C1-C6 alkyl group,

[0388] R' represents a C1-C6 alkyl group,

[0389] T represents an oxygen atom or a sulfur atom,

[0390] R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0391] R X -1~R X -4 represent the structures shown in the following structural formulas,

[0392] [Chemical formula 23]

[0393]

[0394] X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0395] About X 1When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0396] About X 1 When u4 represents an integer of 2, 3 or 4, each X 1 may be the same as or different from each other,

[0397] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0398] R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0399] R 1 represents a hydrogen atom or a C1-C6 alkyl group,

[0400] R 2 represents a hydrogen atom or a C1-C6 alkyl group,

[0401] R 3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0402] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0403] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6, R a -1. R a -2. R a -3. R a -4. R a -5 and R a -6 represent the structures shown in the following structural formulas,

[0404] [Chemical formula 24]

[0405]

[0406] R 5 represents a hydrogen atom or a C1-C6 alkyl group,

[0407] R6 represents a hydrogen atom or a C1-C6 alkyl group,

[0408] In r 1 In the case of the integer 2, the two R 5 and two R 6 may be the same as or different from each other,

[0409] R 7 Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl or phenyl,

[0410] R 8 represents a hydrogen atom or a C1-C6 alkyl group,

[0411] R 9 represents a hydrogen atom or a C1-C6 alkyl group,

[0412] Z represents Z-1, Z-2, Z-3, Z-4, Z-5, Z-6 or Z-7,

[0413] Z-1 to Z-7 represent the following structures respectively:

[0414] [Chemical formula 25]

[0415]

[0416] Among them, Z 1 The substitution position refers to substitution on the aromatic rings of Z-1 to Z-7.

[0417] Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, R i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, E-1 to E-54, F-1 to F-15 or -C(=NOR)R',

[0418] About Z 1When n3 represents an integer of 2 or 3, each Z 1 may be the same as or different from each other,

[0419] About Z 1 When n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other,

[0420] About Z 1 When n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other,

[0421] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, E-1-E-54, F-1-F-15 or C1-C6 alkylaminocarbonyl,

[0422] R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, E-1-E-54, F-1-F-15 or -C(=NOR)R',

[0423] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, benzyloxy, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino,

[0424] R f represents C1-C6 alkyl, C1-C6 haloalkyl, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino,

[0425] R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group,

[0426] R h represents a C1-C6 alkyl group,

[0427] R i represents a hydroxyl group or a C1-C6 alkoxy group,

[0428] E-1 to E-54 represent the structures shown in the following structural formulas,

[0429] [Chemical formula 26]

[0430]

[0431] F-1 to F-15 represent the structures shown in the following structural formulas,

[0432] [Chemical formula 27]

[0433]

[0434] Z a represents a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylcarbonyl group or a C1-C6 alkoxycarbonyl group,

[0435] About Z a When v7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other,

[0436] About Z a When v6 represents an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other,

[0437] About Z a When v5 represents an integer of 2, 3, 4 or 5, each Z a may be the same as or different from each other,

[0438] About Z a When v4 represents an integer of 2, 3, or 4, each Z a may be the same as or different from each other,

[0439] About Z a The relationship between them is that when v3 represents an integer of 2 or 3, each Z a may be the same as or different from each other,

[0440] About Z a The relationship between them, when v2 represents the integer 2, each Z a may be the same as or different from each other,

[0441] Z b represents a C1-C6 alkyl group,

[0442] m5, n5 and u5 each represent an integer of 0, 1, 2, 3, 4 or 5,

[0443] n3 represents an integer 0, 1, 2 or 3,

[0444] u4 represents an integer 0, 1, 2, 3, or 4,

[0445] n7 represents an integer 0, 1, 2, 3, 4, 5, 6 or 7,

[0446] p represents an integer 0 or 1,

[0447] r 1 represents an integer 1 or 2,

[0448] r 2 Represents an integer 0 or 1,

[0449] t represents an integer 0, 1 or 2,

[0450] v1 represents an integer 0 or 1,

[0451] v2 represents an integer 0, 1, or 2,

[0452] v3 represents an integer 0, 1, 2, or 3,

[0453] v4 represents an integer 0, 1, 2, 3, or 4,

[0454] v5 represents an integer 0, 1, 2, 3, 4, or 5,

[0455] v6 represents an integer 0, 1, 2, 3, 4, 5, or 6,

[0456] v7 represents an integer 0, 1, 2, 3, 4, 5, 6, or 7.

[0457] [2] The pyrazole compound or a salt thereof according to [1] above, wherein

[0458] R b represents cyano or phenyl,

[0459] X 1 represents a halogen atom,

[0460] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0461] R Y represents a hydrogen atom,

[0462] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1 or R a -4,

[0463] R 5 represents a hydrogen atom,

[0464] R6 represents a hydrogen atom,

[0465] R 7 represents a C1-C6 alkyl group,

[0466] Z represents Z-1, Z-2, Z-3, Z-4 or Z-6,

[0467] Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, -C(=NOR)R', E-1, E-2, E-3, E-7, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11,

[0468] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1,

[0469] R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6)alkylaminocarbonyl, -C(=NOR)R', E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3,

[0470] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, di(C1-C6)alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-8, E-11, E-13, E-14 or E-23,

[0471] R frepresents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1,

[0472] m5 represents an integer 0, 1 or 2,

[0473] n5 represents an integer 0, 1, 2 or 3,

[0474] n3 represents an integer 0 or 1,

[0475] u5 represents an integer 0 or 1,

[0476] u4 represents the integer 0,

[0477] n7 represents the integer 0,

[0478] r 1 represents the integer 1,

[0479] v1 represents the integer 1,

[0480] v2 represents an integer 0 or 1,

[0481] v3 represents an integer 0, 1, or 2,

[0482] v4 represents an integer 0, 1, 2, or 3,

[0483] v5 represents an integer 0, 1, or 2,

[0484] v6 represents the integer 0.

[0485] [3] The pyrazole compound or a salt thereof according to [2] above, wherein

[0486] R 2 represents a hydrogen atom, and p represents the integer 1.

[0487] [4] The pyrazole compound or a salt thereof according to [3] above, wherein T represents an oxygen atom.

[0488] [5] The pyrazole compound or a salt thereof according to [4] above, wherein R a Represents a hydrogen atom or a C1-C6 alkyl group.

[0489] [6] The pyrazole compound or a salt thereof according to [2] above, wherein p represents an integer of 0.

[0490] [7] The pyrazole compound or a salt thereof according to [6] above, wherein

[0491] G 1 represents a halogen atom, a C1-C6 haloalkyl, a C1-C6 alkoxy or a C1-C6 haloalkoxy,

[0492] T represents oxygen atom,

[0493] R X Represents C1-C6 alkyl, benzyl, R X -1 or R X -2,

[0494] R 1 represents a hydrogen atom,

[0495] R a represents a hydrogen atom, a C1-C6 alkyl group or R a -1,

[0496] Z stands for Z-1, Z-2 or Z-3,

[0497] Z 1 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0498] n5 represents an integer 0, 1 or 2,

[0499] u5 represents the integer 0.

[0500] [8] The pyrazole compound or a salt thereof according to [2] above, wherein

[0501] G 1 represents a halogen atom, a C1-C6 haloalkyl, a C1-C6 alkoxy or a C1-C6 haloalkoxy,

[0502] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0503] T represents oxygen atom,

[0504] R X Represents C1-C6 alkyl, benzyl, R X -1 or R X -2,

[0505] R Y represents a hydrogen atom,

[0506] R 1 represents a hydrogen atom,

[0507] R a represents a hydrogen atom, a C1-C6 alkyl group or R a -1,

[0508] R 5 represents a hydrogen atom,

[0509] R 6 represents a hydrogen atom,

[0510] Z stands for Z-1, Z-2 or Z-3,

[0511] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 alkylthio group,

[0512] About Z 1 The relationship between them, when n5 represents an integer 2, each Z 1 may be the same as or different from each other,

[0513] m5 and n5 each represent an integer 0, 1 or 2,

[0514] u5 represents the integer 0,

[0515] u4 represents the integer 0,

[0516] p represents the integer 0,

[0517] r 1 Represents the integer 1.

[0518] [9] The pyrazole compound or a salt thereof according to [3] above, wherein

[0519] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R',

[0520] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0521] R b represents cyano or phenyl,

[0522] R represents a hydrogen atom or a C1-C6 alkyl group,

[0523] R' represents a C1-C6 alkyl group,

[0524] T represents oxygen atom,

[0525] R X Represents C1~C6 alkyl, C3~C 10Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0526] X 1 represents a halogen atom,

[0527] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0528] R Y represents a hydrogen atom,

[0529] R 1 represents a hydrogen atom,

[0530] R 2 represents a hydrogen atom,

[0531] R 3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0532] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0533] R a represents a hydrogen atom,

[0534] Z represents Z-1, Z-2, Z-3, Z-4 or Z-6,

[0535] Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl or R i Substituted C1-C6 alkyl,

[0536] About Z 1 When n5 represents an integer of 2 or 3, each Z 1 may be the same as or different from each other,

[0537] R i represents a hydroxyl group or a C1-C6 alkoxy group,

[0538] m5 represents an integer 0, 1 or 2,

[0539] n5 represents an integer 0, 1, 2 or 3,

[0540] p represents the integer 1,

[0541] n3 represents an integer 0 or 1,

[0542] u5 represents an integer 0 or 1,

[0543] u4 represents the integer 0,

[0544] n7 represents the integer 0.

[0545]

[10] The pyrazole compound or a salt thereof according to [3] above, wherein

[0546] G 1 represents a halogen atom or a C1-C6 haloalkyl group,

[0547] T represents oxygen atom,

[0548] R X represents a C1-C6 alkyl group,

[0549] R Y represents a hydrogen atom,

[0550] R 1 represents a hydrogen atom,

[0551] R 2 represents a hydrogen atom,

[0552] R 3 represents a hydrogen atom,

[0553] R 4 represents a hydrogen atom,

[0554] R a represents C1-C6 alkyl, R a -1 or R a -4,

[0555] R a -1. R a -2. R a -3. R a -4. R a -5 and R a -6 represent the structures shown in the above structural formula,

[0556] R 5 represents a hydrogen atom,

[0557] R 6 represents a hydrogen atom,

[0558] R 7 represents a C1-C6 alkyl group,

[0559] Z stands for Z-1,

[0560] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0561] About Z 1 The relationship between them, when n5 represents an integer 2, each Z 1 may be the same as or different from each other,

[0562] m5 represents an integer 0 or 1,

[0563] n5 represents the integer 2,

[0564] r 1 represents the integer 1,

[0565] p represents the integer 1.

[0566]

[11] The pyrazole compound or a salt thereof according to [3] above, wherein

[0567] G 1 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group,

[0568] R represents a hydrogen atom or a C1-C6 alkyl group,

[0569] T represents oxygen atom,

[0570] R represents a hydrogen atom or a C1-C6 alkyl group,

[0571] R' represents a C1-C6 alkyl group,

[0572] R X represents a C1-C6 alkyl group,

[0573] R Y represents a hydrogen atom,

[0574] R 1 represents a hydrogen atom,

[0575] R 2 represents a hydrogen atom,

[0576] R 3 represents a hydrogen atom,

[0577] R 4 represents a hydrogen atom,

[0578] R a represents a hydrogen atom,

[0579] Z stands for Z-1,

[0580] Z 1 Representatives i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e , -NHSO2R f 、-C≡CR g , -C(=NOR)R', E-1, E-2, E-3, E-7, E-8, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11,

[0581] About Z 1 When n5 represents an integer of 2 or 3, each Z 1 may be the same as or different from each other,

[0582] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1,

[0583] R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6)alkylaminocarbonyl, -C(=NOR)R', E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3,

[0584] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, di(C1-C6)alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-11, E-13, E-14 or E-23,

[0585] R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1,

[0586] R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group,

[0587] R h represents a C1-C6 alkyl group,

[0588] R i represents a C1-C6 alkoxy group,

[0589] Z a represents a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group or a C1-C6 alkoxycarbonyl group,

[0590] m5 represents an integer 0 or 1,

[0591] n5 represents the integer 1,

[0592] n7 represents the integer 0,

[0593] v1 represents the integer 1,

[0594] v2 represents an integer 0 or 1,

[0595] v3 represents an integer 0, 1, or 2,

[0596] v4 represents an integer 0, 1, or 2,

[0597] v5 represents an integer 0, 1, or 2,

[0598] v6 represents the integer 0.

[0599]

[12] The pyrazole compound or a salt thereof according to [3] above, wherein

[0600] G 1 represents a C1-C6 haloalkyl group,

[0601] T represents oxygen atom,

[0602] R X represents a C1-C6 alkyl group,

[0603] R Y represents a hydrogen atom,

[0604] R 1 represents a C1-C6 alkyl group,

[0605] R 2 represents a hydrogen atom,

[0606] R 3 represents a hydrogen atom,

[0607] R 4 represents a hydrogen atom,

[0608] R a represents a hydrogen atom,

[0609] Z stands for Z-1,

[0610] Z 1 Represents C1~C6 alkyl or R i Substituted C1-C6 alkyl,

[0611] About Z 1 The relationship between them, when n5 represents an integer 2, each Z 1 may be the same as or different from each other,

[0612] R i represents a C1-C6 alkoxy group,

[0613] m5 represents an integer 0 or 1,

[0614] n5 represents an integer of 1 or 2.

[0615]

[13] The pyrazole compound or salt thereof according to [3] above, wherein

[0616] G 1 represents a C1-C6 haloalkyl group,

[0617] T represents sulfur atom,

[0618] R X represents C1~C6 alkyl or R X -1,

[0619] R Y represents a hydrogen atom,

[0620] R 1 represents a hydrogen atom,

[0621] R 2 represents a hydrogen atom,

[0622] R 3 represents a hydrogen atom,

[0623] R 4 represents a hydrogen atom,

[0624] R a represents a hydrogen atom,

[0625] Z stands for Z-1,

[0626] Z 1 represents a C1-C6 alkyl group,

[0627] About Z 1 The relationship between them, when n5 represents an integer 2, each Z 1 may be the same as or different from each other,

[0628] m5 represents the integer 1,

[0629] n5 represents an integer 1 or 2,

[0630] u5 represents the integer 0.

[0631]

[14] The pyrazole compound or a salt thereof according to [3] above, wherein

[0632] G 1 represents a C1-C6 haloalkyl group,

[0633] T represents oxygen atom,

[0634] R X represents a C1-C6 alkyl group,

[0635] R Y represents a hydrogen atom,

[0636] R 1 represents a hydrogen atom,

[0637] R 2 represents a hydrogen atom,

[0638] R 3 represents a hydrogen atom,

[0639] R 4 represents a hydrogen atom,

[0640] R a represents a hydrogen atom,

[0641] Z stands for Z-1,

[0642] Z 1 Represents C1~C6 alkyl or -OR d ,

[0643] About Z 1 The relationship between them, when n5 represents an integer 2, each Z 1 may be the same as or different from each other,

[0644] R d represents a C1-C6 haloalkyl group,

[0645] m5 represents the integer 1,

[0646] n5 represents the integer 2.

[0647]

[15] The pyrazole compound or a salt thereof according to [3] above, wherein

[0648] G 1 represents a C1-C6 haloalkyl group,

[0649] T represents oxygen atom,

[0650] R X represents a C1-C6 alkyl group,

[0651] R Y represents a hydrogen atom,

[0652] R 1 represents a hydrogen atom,

[0653] R 2 represents a hydrogen atom,

[0654] R 3 represents a hydrogen atom,

[0655] R 4 represents a hydrogen atom,

[0656] R a represents a hydrogen atom,

[0657] Z stands for Z-1,

[0658] Z 1 stands for E-1 or E-2,

[0659] Z a represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0660] About Z a The relationship between them, when v5 represents the integer 2, each Z a may be the same as or different from each other,

[0661] m5 represents the integer 2,

[0662] n5 represents the integer 2,

[0663] v4 represents the integer 0,

[0664] v5 represents an integer 1 or 2.

[0665]

[16] The pyrazole compound or a salt thereof according to any one of [1] to

[15] above, wherein

[0666] G 1 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group,

[0667] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0668] R X represents C1~C6 alkyl or R X -1,

[0669] R Y represents a hydrogen atom,

[0670] R a represents a hydrogen atom or a C1-C6 alkyl group,

[0671] Z stands for Z-1,

[0672] Z 1 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, -NHC(O)R e 、-NR h C(O)R e or E-2, n5 represents an integer 0, 1 or 2,

[0673] u5 represents the integer 0.

[0674]

[17] The pyrazole compound or a salt thereof according to (16) above, wherein

[0675] G 1 represents a chlorine atom, a bromine atom, a methyl group or a trifluoromethyl group,

[0676] R X Represents tert-butyl or R X -1,

[0677] R a represents a hydrogen atom or a methyl group,

[0678] Z 1 Represents methyl.

[0679]

[18] The pyrazole compound or a salt thereof according to any one of [1] to [6] above, wherein

[0680] G 1 represents a halogen atom, a C1-C6 alkyl group, a C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl,

[0681] di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl,

[0682] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0683] m5 represents an integer of 0, 1 or 2.

[0684]

[19] The pyrazole compound or a salt thereof according to

[18] above, wherein

[0685] G 1represents a halogen atom, a C1-C6 alkyl group, a C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl,

[0686] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0687] m5 represents an integer of 0, 1 or 2.

[0688]

[20] The pyrazole compound or a salt thereof according to

[19] above, wherein

[0689] G 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylcarbonyl group or a C1-C6 alkoxycarbonyl group,

[0690] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0691] m5 represents an integer of 0, 1 or 2.

[0692]

[21] The pyrazole compound or salt thereof according to

[20] above, wherein

[0693] G 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group or a C1-C6 haloalkoxy group,

[0694] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0695] m5 represents an integer of 0, 1 or 2.

[0696]

[22] The pyrazole compound or a salt thereof according to [7] or

[21] above, wherein

[0697] G 1 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group,

[0698] About G 1The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0699] m5 represents an integer of 0, 1 or 2.

[0700]

[23] The pyrazole compound or salt thereof according to

[22] above, wherein

[0701] G 1 represents a chlorine atom, a bromine atom, a methyl group, an ethyl group or a trifluoromethyl group,

[0702] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0703] m5 represents an integer of 0, 1 or 2.

[0704]

[24] The pyrazole compound or a salt thereof according to

[22] above, wherein

[0705] G 1 represents a halogen atom or a C1-C6 haloalkyl group,

[0706] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0707] m5 represents an integer of 0, 1 or 2.

[0708]

[25] The pyrazole compound or a salt thereof according to

[24] above, wherein

[0709] G 1 represents a chlorine atom, a bromine atom or a trifluoromethyl group,

[0710] About G 1 The relationship between them, when m5 represents the integer 2, each G 1 may be the same as or different from each other,

[0711] m5 represents an integer of 0, 1 or 2.

[0712]

[26] The pyrazole compound or a salt thereof according to any one of [1] to

[25] above, wherein m5 represents an integer of 0 or 1.

[0713]

[27] The pyrazole compound or a salt thereof according to

[26] above, wherein m5 represents an integer of 1.

[0714]

[28] The pyrazole compound or a salt thereof according to any one of [1] to [6] and

[18] to

[27] above, wherein

[0715] R X represents C1~C6 alkyl, C1~C6 haloalkyl, c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0716] X 1 represents a halogen atom,

[0717] About X 1 When u5 represents an integer of 2 or 3, each X 1 may be the same as or different from each other,

[0718] X 1 represents a halogen atom,

[0719] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl,

[0720] u5 represents an integer 0 or 1,

[0721] u4 represents the integer 0.

[0722]

[29] The pyrazole compound or a salt thereof according to

[28] above, wherein

[0723] R X represents C1-C6 alkyl, C1-C6 haloalkyl, R X -1. R X -2. R X -3 or R X -4, u5 represents the integer 0,

[0724] u4 represents the integer 0.

[0725]

[30] The pyrazole compound or a salt thereof according to

[29] above, wherein

[0726] R X represents C1-C6 alkyl, C1-C6 haloalkyl, R X -1 or R X -2,

[0727] u5 represents the integer 0,

[0728] u4 represents the integer 0.

[0729]

[31] The pyrazole compound or salt thereof according to

[30] above, wherein

[0730] R X represents C1-C6 alkyl, C1-C6 haloalkyl or R X -1,

[0731] u5 represents the integer 0.

[0732]

[32] The pyrazole compound or salt thereof according to

[31] above, wherein

[0733] R X represents C1~C6 alkyl or R X -1,

[0734] u5 represents the integer 0.

[0735]

[33] The pyrazole compound or a salt thereof according to [7] or

[32] above, wherein R X Represents C1~C6 alkyl.

[0736]

[34] The pyrazole compound or a salt thereof according to

[33] above, wherein R X Stands for tert-butyl.

[0737]

[35] The pyrazole compound or a salt thereof according to any one of [1] to [6] and

[18] to

[34] above, wherein

[0738] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1 or R a -4,

[0739] R 5 represents a hydrogen atom,

[0740] R 6 represents a hydrogen atom,

[0741] R 7 represents a C1-C6 alkyl group,

[0742] r 1 represents the integer 1,

[0743] t represents an integer of 0, 1 or 2.

[0744]

[36] The pyrazole compound or a salt thereof according to

[35] above, wherein

[0745] R a Represents R a -1 or R a -4,

[0746] R 5 represents a hydrogen atom,

[0747] R 6 represents a hydrogen atom,

[0748] R 7 represents a C1-C6 alkyl group,

[0749] r 1 represents the integer 1,

[0750] t represents an integer of 0, 1 or 2.

[0751]

[37] The pyrazole compound or salt thereof according to [7] or

[36] above, wherein

[0752] R a Represents R a -1,

[0753] R 5 represents a hydrogen atom,

[0754] R 6 represents a hydrogen atom,

[0755] R 7 Represents methyl,

[0756] r 1 Represents the integer 1.

[0757]

[38] The pyrazole compound or a salt thereof according to

[36] above, wherein

[0758] R a Represents R a -4,

[0759] R 5 represents a hydrogen atom,

[0760] R 6 represents a hydrogen atom,

[0761] R 7 Represents methyl,

[0762] r 1 Represents the integer 1.

[0763]

[39] The pyrazole compound or a salt thereof according to [7] or

[35] above, wherein R a Represents a hydrogen atom or a C1-C6 alkyl group.

[0764]

[40] The pyrazole compound or a salt thereof according to

[39] above, wherein R a Represents a hydrogen atom.

[0765]

[41] The pyrazole compound or a salt thereof according to

[39] above, wherein R a , represents C1~C6 alkyl.

[0766]

[42] The pyrazole compound or a salt thereof according to

[41] above, wherein R a Represents methyl.

[0767]

[43] The pyrazole compound or a salt thereof according to any one of [1] to [7] and

[18] to

[42] above, wherein Z represents Z-1.

[0768]

[44] The pyrazole compound or a salt thereof according to any one of [1] to [5] and

[18] to

[43] above, wherein

[0769] Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, -C(=NOR)R', E-1, E-2, E-3, E-7, E-8, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11,

[0770] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1,

[0771] R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6)alkylaminocarbonyl, -C(=NOR)R', E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3,

[0772] R erepresents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, di(C1-C6)alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-11, E-13, E-14 or E-23,

[0773] R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1,

[0774] R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group,

[0775] R h represents a C1-C6 alkyl group,

[0776] R i represents a hydroxyl group or a C1-C6 alkoxy group,

[0777] n5 represents an integer of 0, 1, 2 or 3.

[0778]

[45] The pyrazole compound or a salt thereof according to

[44] above, wherein

[0779] Z 1 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e NHSO2R f , -C(=NOR)R' or E-2.

[0780]

[46] The pyrazole compound or a salt thereof according to

[45] above, wherein

[0781] Z 1 represents a hydroxyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e or E-2;

[0782] Rd Represents C1~C6 haloalkyl.

[0783]

[47] The pyrazole compound or a salt thereof according to

[46] above, wherein

[0784] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e or E-2;

[0785] R d Represents C1~C6 haloalkyl.

[0786]

[48] ​​The pyrazole compound or salt thereof according to

[47] above, wherein

[0787] Z 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, -OR d or E-2,

[0788] R d Represents C1~C6 haloalkyl.

[0789]

[49] The pyrazole compound or salt thereof according to [7] or

[48] above, wherein

[0790] Z 1 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0791] n5 represents an integer of 0, 1 or 2.

[0792]

[50] The pyrazole compound or a salt thereof according to

[49] above, wherein

[0793] Z 1 represents a chlorine atom, a bromine atom, a methyl group or a methoxy group,

[0794] n5 represents an integer of 0, 1 or 2.

[0795]

[51] The pyrazole compound or a salt thereof according to

[49] above, wherein Z 1 Represents C1~C6 alkyl.

[0796]

[52] The pyrazole compound or a salt thereof according to any one of [1] to

[51] above, wherein n5 represents an integer of 1 or 2.

[0797]

[53] The pyrazole compound or the salt thereof according to

[52] above, wherein n5 represents an integer of 2.

[0798]

[54] The pyrazole compound or a salt thereof according to any one of [1] to [7] and

[18] to

[42] above, wherein

[0799] Z stands for Z-2 or Z-3,

[0800] n7 represents the integer 0.

[0801]

[55] The pyrazole compound or a salt thereof according to any one of [1] to [6] and

[18] to

[42] above, wherein

[0802] Z stands for Z-4 or Z-6,

[0803] Z 1 represents a halogen atom,

[0804] n3 represents an integer 0 or 1.

[0805]

[56] The pyrazole compound or a salt thereof according to any one of [1] to [2] and

[18] to

[55] above, wherein p represents an integer of 0.

[0806]

[57] The pyrazole compound or a salt thereof according to any one of [1] to [2] and

[18] to

[55] above, wherein p represents 1.

[0807]

[58] The pyrazole compound or salt thereof according to [1] above, wherein

[0808] G 1 represents a halogen atom, a C3-C6 cycloalkyl group or a C1-C6 haloalkyl group,

[0809] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0810] R X represents C1-C6 alkyl, benzyl or R X -1,

[0811] X 1 represents a halogen atom or a C1-C6 alkyl group,

[0812] About X 1 When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0813] R Yrepresents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0814] R 1 represents a hydrogen atom or a C1-C6 alkyl group,

[0815] R 2 represents a hydrogen atom or a C1-C6 alkyl group,

[0816] R 3 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0817] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0818] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6,

[0819] R 5 represents a hydrogen atom or a C1-C6 alkyl group,

[0820] R 6 represents a hydrogen atom or a C1-C6 alkyl group,

[0821] In r 1 In the case of the integer 2, the two R 5 and two R 6 may be the same as or different from each other,

[0822] R 7 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group or a phenyl group,

[0823] R 8 represents a hydrogen atom or a C1-C6 alkyl group,

[0824] R 9 represents a hydrogen atom or a C1-C6 alkyl group,

[0825] Z stands for Z-1,

[0826] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0827] About Z 1 When n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other,

[0828] m5, n5 and u5 represent integers 0, 1, 2, 3, 4 or 5,

[0829] p represents an integer 0 or 1,

[0830] r 1 represents an integer 1 or 2,

[0831] r 2 Represents an integer 0 or 1,

[0832] t represents an integer of 0, 1 or 2.

[0833]

[59] The pyrazole compound or a salt thereof according to

[58] above, wherein

[0834] T represents oxygen atom,

[0835] X 1 represents a halogen atom,

[0836] R Y represents a hydrogen atom,

[0837] R 1 represents a hydrogen atom,

[0838] R 3 represents a halogen atom,

[0839] R 4 represents a halogen atom,

[0840] R a represents a hydrogen atom or a C1-C6 alkyl group,

[0841] Z 1 represents a C1-C6 alkyl group,

[0842] m5 and n5 represent integers 1 or 2,

[0843] u5 represents an integer 0 or 1.

[0844]

[60] The pyrazole compound or salt thereof according to [1] above, wherein

[0845] G 1 Represents halogen atoms, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy or di(C1-C6 alkylamino),

[0846] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0847] R X Represents C1~C6 alkyl, C3~C10 Cycloalkyl, benzyl or R X -1,

[0848] X 1 represents a halogen atom or a C1-C6 alkyl group,

[0849] About X 1 When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0850] R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0851] R 1 represents a hydrogen atom or a C1-C6 alkyl group,

[0852] R 2 represents a hydrogen atom or a C1-C6 alkyl group,

[0853] R 3 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0854] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0855] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6,

[0856] R 5 represents a hydrogen atom or a C1-C6 alkyl group,

[0857] R 6 represents a hydrogen atom or a C1-C6 alkyl group,

[0858] In r 1 In the case of the integer 2, the two R 5 and two R 6 may be the same as or different from each other,

[0859] R 7 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group or a phenyl group,

[0860] R 8 represents a hydrogen atom or a C1-C6 alkyl group,

[0861] R 9represents a hydrogen atom or a C1-C6 alkyl group,

[0862] Z stands for Z-1, Z-2 or Z-3,

[0863] Z 1 represents a halogen atom or a C1-C6 alkyl group,

[0864] About Z 1 When n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other,

[0865] About Z 1 When n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other,

[0866] m5, n5 and u5 represent integers 0, 1, 2, 3, 4 or 5,

[0867] n7 represents an integer 0, 1, 2, 3, 4, 5, 6 or 7,

[0868] p represents an integer 0 or 1,

[0869] r 1 represents an integer 1 or 2,

[0870] r 2 Represents an integer 0 or 1,

[0871] t represents an integer of 0, 1 or 2.

[0872]

[61] The pyrazole compound or a salt thereof according to

[60] above, wherein

[0873] G 1 Represents halogen atoms, C3~C 10 Cycloalkyl or C1-C6 haloalkyl,

[0874] T represents oxygen atom,

[0875] X 1 represents a halogen atom,

[0876] R Y represents a hydrogen atom,

[0877] R 1 represents a hydrogen atom,

[0878] R 3 represents a hydrogen atom or a halogen atom,

[0879] R 4 represents a hydrogen atom or a halogen atom,

[0880] R a represents a hydrogen atom, a C1-C6 alkyl group or R a -1,

[0881] R 5 represents a hydrogen atom,

[0882] R 6 represents a hydrogen atom,

[0883] R 7 represents a C1-C6 alkyl group,

[0884] Z stands for Z-1 or Z-2,

[0885] m5 represents an integer 0, 1 or 2,

[0886] n5 represents an integer 1 or 2,

[0887] u5 represents an integer 0 or 1,

[0888] n7 represents the integer 0,

[0889] r 1 Represents the integer 1. (62)

[0891] The pyrazole compound or a salt thereof according to (1) above, wherein

[0892] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, or -C(=NOR)R',

[0893] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0894] R b Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R',

[0895] R represents a hydrogen atom or a C1-C6 alkyl group,

[0896] R' represents a C1-C6 alkyl group,

[0897] T represents an oxygen atom or a sulfur atom,

[0898] R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0899] X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0900] About X 1 When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0901] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0902] R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0903] R 1 represents a hydrogen atom or a C1-C6 alkyl group,

[0904] R 2 represents a hydrogen atom or a C1-C6 alkyl group,

[0905] R 3 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0906] R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0907] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6,

[0908] R5 represents a hydrogen atom or a C1-C6 alkyl group,

[0909] R 6 represents a hydrogen atom or a C1-C6 alkyl group,

[0910] In r 1 In the case of the integer 2, the two R 5 and two R 6 may be the same as or different from each other,

[0911] R 7 Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl or phenyl,

[0912] R 8 represents a hydrogen atom or a C1-C6 alkyl group,

[0913] R 9 represents a hydrogen atom or a C1-C6 alkyl group,

[0914] Z represents Z-1 to Z-7,

[0915] Z 1 represents a hydroxyl group, an amino group, a nitro group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkoxycarbonyl group, -OR d 、-NHC(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2 or E-1~E-34,

[0916] About Z 1 When n5 represents an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other,

[0917] About Z 1 When n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other,

[0918] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl, E-1-E-33 or E-34,

[0919] R 10represents a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, -C(=NOR)R', E-1-E-33 or E-34,

[0920] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylamino, di(C1-C6 alkyl)amino, E-1-E-33 or E-34,

[0921] R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino, E-1-E-33 or E-34,

[0922] R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group,

[0923] Z a represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0924] About Z a When v5 represents an integer of 2, 3, 4 or 5, each Z a may be the same as or different from each other,

[0925] About Z a When v4 represents an integer of 2, 3, or 4, each Z a may be the same as or different from each other,

[0926] About Z a The relationship between them is that when v3 represents an integer of 2 or 3, each Z a may be the same as or different from each other,

[0927] About Z a The relationship between them, when v2 represents the integer 2, each Z a may be the same as or different from each other,

[0928] Z b represents a C1-C6 alkyl group,

[0929] m5, n5 and u5 represent integers 0, 1, 2, 3, 4 or 5,

[0930] u4 represents an integer 0, 1, 2, 3, or 4,

[0931] n7 represents an integer 0, 1, 2, 3, 4, 5, 6 or 7,

[0932] p represents an integer 0 or 1,

[0933] r 1 represents an integer 1 or 2,

[0934] r 2 Represents an integer 0 or 1,

[0935] t represents an integer 0, 1 or 2,

[0936] v2 represents an integer 0, 1, or 2,

[0937] v3 represents an integer 0, 1, 2, or 3,

[0938] v4 represents an integer 0, 1, 2, 3, or 4,

[0939] v5 represents an integer 0, 1, 2, 3, 4, or 5.

[0940]

[63] The pyrazole compound or salt thereof according to

[62] above, wherein

[0941] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R',

[0942] R b represents cyano or phenyl,

[0943] T represents oxygen atom,

[0944] R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl or R X -1,

[0945] X 1 represents a halogen atom,

[0946] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0947] R Y represents a hydrogen atom,

[0948] R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1 or R a -4,

[0949] R 5 represents a hydrogen atom,

[0950] R 6 represents a hydrogen atom,

[0951] R 7 represents a C1-C6 alkyl group,

[0952] Z represents Z-1~Z-3 or Z-4,

[0953] Z 1 represents a hydroxyl group, an amino group, a nitro group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfonyl group, a C1-C6 alkoxycarbonyl group, -OR d 、-NHC(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, E-1, E-3, E-7, E-12, E-14, E-21, E-23, E-24 or E-31,

[0954] R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1,

[0955] R 10 represents a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a di(C1-C6)alkylaminocarbonyl group, -C(=NOR)R', E-1 or E-2,

[0956] R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylamino, di(C1-C6)alkylamino, E-1, E-2, E-4 or E-23,

[0957] R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1,

[0958] Z a represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group,

[0959] m5 represents an integer 0, 1 or 2,

[0960] n5 represents an integer 0, 1, 2 or 3,

[0961] u5 represents an integer 0 or 1,

[0962] n7 represents the integer 0,

[0963] r 1 represents the integer 1,

[0964] v2 represents an integer 0 or 1,

[0965] v3 represents the integer 0,

[0966] v4 represents an integer 0 or 1,

[0967] v5 represents an integer 0 or 1.

[0968]

[64] A production intermediate represented by formula (1-1a), which is a production intermediate of the pyrazole compound described in any one of the above [1] to

[63] .

[0969] [Chemical formula 28]

[0970]

[0971] In the formula, G represents G-1, and G-1 represents the structure shown in the following structural formula,

[0972] [Chemical formula 29]

[0973]

[0974] G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R',

[0975] About G 1 In the case where m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other,

[0976] Rb Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R',

[0977] R represents a hydrogen atom or a C1-C6 alkyl group,

[0978] R' represents a C1-C6 alkyl group,

[0979] R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4,

[0980] R X -1~R X -4 represent the structures shown in the following structural formulas,

[0981] [Chemical formula 30]

[0982]

[0983] X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group,

[0984] About X 1 When u5 represents an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other,

[0985] About X 1 When u4 represents an integer of 2, 3 or 4, each X 1 may be the same as or different from each other,

[0986] R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R',

[0987] R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group,

[0988] m5 and u5 represent integers 0, 1, 2, 3, 4, or 5.

[0989] u4 represents the integer 0, 1, 2, 3, or 4.

[0990]

[65] The production intermediate according to

[64] above, wherein

[0991] G 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group or a C1-C6 alkylthio group,

[0992] R X Represents C1-C6 alkyl, benzyl, R X -1. R X -2 or R X -3,

[0993] X 1 represents a halogen atom,

[0994] R Y represents a hydrogen atom,

[0995] m5 represents an integer 0, 1 or 2,

[0996] u5 represents an integer 0 or 1,

[0997] u4 represents the integer 0.

[0998]

[66] A pesticide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof selected from any one of [1] to

[63] above.

[0999]

[67] A fungicide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof selected from any one of [1] to

[63] above.

[1000]

[68] An agricultural and horticultural fungicide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof selected from any one of [1] to

[63] above.

[1001]

[69] An antifungal agent comprising, as an active ingredient, at least one pyrazole compound or a salt thereof selected from any one of [1] to

[63] above.

[1002]

[70] An internal parasite control agent comprising, as an active ingredient, at least one pyrazole compound or a salt thereof selected from any one of [1] to

[63] above.

[1003] [Example]

[1004] Hereinafter, the present invention will be described in more detail by describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited to these examples.

[1005] As the medium-pressure fractionation liquid chromatography apparatus described in the synthesis examples, a medium-pressure fractionation apparatus YFLC-Wprep (flow rate 18 ml / min, 40 μm silica gel column) manufactured by Yamazen Co., Ltd. was used.

[1006] In addition, regarding the proton nuclear magnetic resonance spectrum (hereinafter referred to as 1 The chemical shift values ​​on H-NMR were measured at 300 MHz (model JNM-ECX300 or JNM-ECP300; manufactured by JEOL) or 400 MHz (model JNM-ECZ400S; manufactured by JEOL) using Me4Si (tetramethylsilane) as a standard. 1 The chemical shift values ​​in H-NMR have the following meanings.

[1007] s: singlet; d: doublet; dd: doublet of doublets, t: triplet, dt: doublet of triplet, q: quadruple; sep: septuple; m: multiplet; br: broad singlet.

[1008] [Synthesis example]

[1009] Synthesis Example 1: Synthesis of N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-001)

[1010] Step 1: Synthesis of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[1011] At room temperature, 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid 1.0g and dimethylbenzene 5ml mixed solution, sequentially add 3-(trifluoromethyl) phenol 0.42ml, cesium carbonate 1.6g, 4-(dimethylamino) pyridine 19mg and trifluoromethanesulfonic acid copper (1 valence) toluene complex 33mg. After nitrogen ventilation, stir at reflux temperature for 8 hours. After the reaction is completed, add water 10ml to the reaction mixture, wash the water layer with diethyl ether 10ml. Add 35 mass % hydrochloric acid aqueous solution to the obtained water layer until pH reaches 1, then extract with ethyl acetate 20ml. The obtained organic layer is dehydrated / dried with saturated brine and then anhydrous sodium sulfate, and then the solvent is distilled off under reduced pressure to obtain the target 566mg, which is a brown solid.

[1012] Step 2: Synthesis of N-(2-(2,4-dimethylphenyl)-2,2-difluoroethyl)-1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-001)

[1013] At room temperature, 226 mg of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 0.17 ml of N,N-diisopropylethylamine, and 92 mg of 2-(2,4-dimethylphenyl)-2,2-difluoroethane-1-amine were added to a mixed solution of 173 mg of 1-phenyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid obtained in step 1 and 4 ml of dichloromethane, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, 5 ml of a 1 mol / l aqueous hydrochloric acid solution was added to the reaction mixture, and extraction was performed with 5 ml of dichloromethane. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using a mixture of n-hexane:ethyl acetate (gradient of 9:1 to 1:9 (volume ratio; the same applies hereinafter)) as the eluent to obtain 62 mg of the target product as a yellow solid with a melting point of 82-85°C.

[1014] Synthesis Example 2: Synthesis of N-(2,4-dimethylphenethyl)-1-ethyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-159)

[1015] At room temperature, 0.19 ml of iodoethane was added to a mixed solution of 500 mg of N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 332 mg of potassium carbonate and 5 ml of dimethylformamide, and stirred at 50°C for 1 hour. After the reaction was completed, 5 ml of saturated aqueous ammonium chloride solution was added at room temperature, and extraction was performed with diisopropyl ether (5 ml × 2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane:ethyl acetate (mixing gradient of 9:1 to 1:9) as an eluent to obtain 66 mg of the target product as a colorless oil.

[1016] 1H-NMR (CDCl3, Me4Si, 300MHz): δ7.51-7.34(m,2H),7.28-7.04(m,3H),6.97-6.65(m,4H),4.67(q,J=7 .2Hz,2H),3.69-3.52(m,2H),2.80(t,J=6.8Hz,2H),2.23(s,3H),2.21(s,3H),1.46(t,J=7.2Hz,3H).

[1017] Synthesis Example 3: Synthesis of 1-(tert-butyl)-N-(1-(2,4-dimethylphenyl)-3-(methylsulfonyl)propan-2-yl)-4-phenoxy-1H-pyrazole-5-carboxamide (Compound No. 3-011)

[1018] Under ice cooling, 158 mg of m-chloroperbenzoic acid (containing 30% by mass of water) was added to a mixed solution of 289 mg of 1-(tert-butyl)-N-(1-(2,4-dimethylphenyl)-3-(methylthio)propane-2-yl)-4-phenoxy-1H-pyrazole-5-carboxamide and 5 ml of dichloromethane, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, 5 ml of a saturated aqueous sodium sulfite solution was added at room temperature, and extraction was performed with chloroform (5 ml × 1 time). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane:ethyl acetate (mixing gradient of 9:1 to 1:9) as an eluent to obtain 61 mg of the target substance as a solid with a melting point of 131 to 133°C.

[1019] Synthesis Example 4: Synthesis of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-N-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 5-001)

[1020] Under ice cooling, 16 mg of 63% by mass sodium hydride (dispersed in mineral oil) and 25 μl of methyl iodide were added to a mixed solution of 92 mg of 1-(tert-butyl)-N-(2,4-dimethylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 1 ml of N,N-dimethylformamide in sequence, and stirred at room temperature for 4 hours. After the reaction was completed, 3 ml of saturated aqueous ammonium chloride solution was added at room temperature, and extraction was performed with diisopropyl ether (3 ml × 2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane:ethyl acetate (mixing gradient of 9:1 to 1:9) as an eluent to obtain 65 mg of the target substance as a colorless oil.

[1021] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.43-7.35(m,1H),7.32-7.27(m,2H),7.20-7.12(m,1H),7.03-6.90( m,3H),6.89-6.83(m,1H),3.80-3.28(m,2H),3.10-2.55(m,5H),2.30-2.16(m,6H),1.68-1.59(m,9H).

[1022] Synthesis Example 5: Synthesis of 1-isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-thiocarboxamide (Compound No. 6-002)

[1023] At room temperature, to a mixed solution of 300 mg of 1-isopropyl-N-(4-methylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 ml of xylene, 340 mg of Lawesson's reagent was added, and the mixture was stirred at room temperature to 120°C for 2 hours. After the reaction was completed, 5 ml of n-hexane was added at room temperature, and the insoluble matter was filtered out. The solvent was distilled off from the obtained filtrate under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane: ethyl acetate (with a gradient of 9:1 to 1:9 as the eluent, and 311 mg of the target substance was obtained as a resinous substance.

[1024] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ8.05-7.92(m,1H),7.45-7.32(m,2H),7.20(s,1H),7.18-7.14(m,1H),7.07-6.9 8(m,5H),5.87(sep,J=6.5Hz,1H),4.02-3.93(m,2H),2.87(t,J=6.8Hz,2H),2.26(s,3H),1.48(d,J=6.5Hz,6H).

[1025] Synthesis Example 6: Synthesis of 1-(tert-butyl)-N-(4-ethoxyphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 2-092)

[1026] To a mixed solution of 80 mg of 1-(tert-butyl)-N-(4-hydroxyphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 3 ml of N,N-dimethylformamide, 62 mg of potassium carbonate and 36 μl of iodoethane were added in sequence at room temperature, and stirred at 60°C for 3 hours. After the reaction was completed, 3 ml of saturated aqueous ammonium chloride solution was added at room temperature, and extraction was performed with diisopropyl ether (3 ml × 2 times). The obtained organic layer was washed with water, dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 74 mg of the target product as a light yellow solid with a melting point of 74 to 77°C.

[1027] Synthesis Example 7: Synthesis of N-(4-acetylaminophenethyl)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 4-001)

[1028] To a mixed solution of 200 mg of N-(4-aminophenethyl)-1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml of dichloromethane at room temperature, 91 mg of acetic anhydride was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, 3 ml of water was added at room temperature, and extraction was performed with dichloromethane (3 ml × 2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane: ethyl acetate (2:1) as an eluent to obtain 120 mg of the target product as a resinous substance.

[1029] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.47-7.39(m,1H),7.38-7.29(m,3H),7.23-7.16(m,1H),7.14(s,1H),7 .12-6.99(m,4H),6.50-6.35(m,1H),3.66-3.56(m,2H),2.76(t,J=6.8Hz,2H),2.17(s,3H),1.72(s,9H).

[1030] [Reference example]

[1031] Hereinafter, a method for producing a production intermediate of the compound of the present invention will be described as a reference example.

[1032] Reference Example 1: Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid

[1033] At room temperature, 2.5 g of N-iodosuccinimide was added to a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid, and the mixture was stirred at 80°C for 30 minutes. After the reaction was completed, 50 ml of water was added at room temperature, and the precipitated solid was filtered out. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target product, which was a pink solid with a melting point of 191 to 193°C.

[1034] Reference Example 2: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[1035] Step 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)-3-buten-2-one

[1036] A mixed solution of 4.7 g of 1-(3-(trifluoromethyl)phenoxy)propane-2-one and 2.9 g of N,N-dimethylformamide dimethyl acetal was stirred at 80°C for 16 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as the eluent. 10 ml of diisopropyl ether and 10 ml of n-hexane were added to the obtained oily substance, and the precipitated solid was filtered out. The obtained solid was dried under reduced pressure to obtain 2.36 g of the target product, which was a light brown solid with a melting point of 112 to 114°C.

[1037] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole

[1038] A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)-3-butene-2-one, 1.64 g of tert-butylhydrazine hydrochloride and 25 ml of 1,4-dioxane was stirred at 100°C for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and extraction was performed with n-hexane (20 ml × 2 times). The obtained organic layer was dehydrated / dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue and a mixed solution of n-hexane: ethyl acetate (5:1) were used as eluents and purified by silica gel column chromatography to obtain 2.51 g of the target product as a light yellow oil.

[1039] 1H-NMR (CDCl3, Me4Si, 300MHz): δ7.42-7.32(m,1H),7.28(s,1H),7.28-7.22(m,1H),7.21-7.14(m,1H),7.12-7.04(m,1H),2.29(s,3H),1.66(s,9H).

[1040] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[1041] At room temperature, 1.48 g of potassium permanganate was added to a mixed solution of 930 mg of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butanol and 4.3 ml of water, and the mixture was stirred at 100°C for 2 hours. After the stirring was completed, 1.48 g of potassium permanganate was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the reaction mixture was filtered with diatomaceous earth and washed with 20 ml of water. The water layer of the obtained filtrate was washed with chloroform (20 ml × 2 times), and then a 1 mol / l hydrochloric acid aqueous solution was added until the pH reached 1, and then extracted with chloroform (20 ml × 2 times). The obtained organic layer was washed with water, then dehydrated / dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 5 ml of n-hexane and then dried under reduced pressure to obtain 209 mg of the target product as a white solid with a melting point of 120 to 124°C.

[1042] Reference Example 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[1043] Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrolein

[1044] Under ice cooling, 5.6 ml of phosphorus oxychloride was added to 15 ml of N,N-dimethylformamide, and the mixture was stirred at the ice-cooling temperature for 15 minutes. After the stirring was completed, a solution of 5.0 g of 1-(2,2-dimethoxyethoxy)-3-(trifluoromethyl)benzene in 5 ml of N,N-dimethylformamide was added to the reaction mixture under ice cooling, and stirred at 70°C for 30 minutes. After the reaction was completed, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water and 5 ml of ethanol, and stirred at room temperature for 1 hour. After the stirring was completed, the reaction mixture was extracted with toluene (40 ml × 2 times). The obtained organic layer was washed with water, then dehydrated / dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.40 g of the target product as a brown oil.

[1045] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ8.82 (s, 1H), 7.52-7.03 (m, 3H), 7.03-6.95 (m, 1H), 6.62 (s, 1H), 3.12 (br, 6H).

[1046] Step 2: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole

[1047] A mixed solution of 2.0 g of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrolein, 2.4 g of benzylhydrazine hydrochloride, 2.1 ml of triethylamine and 25 ml of 1,4-dioxane was stirred at 100°C for 3 hours. After the reaction was completed, 20 ml of a 1 mol / l aqueous hydrochloric acid solution was added to the reaction mixture at room temperature, and then extracted with chloroform (30 ml x 2 times). The obtained organic layer was washed with water, then dehydrated / dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane:ethyl acetate (mixing gradient of 9:1 to 1:9) as an eluent to obtain 400 mg of the target product as a red oil.

[1048] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.46-7.20(m,7H),7.20-7.14(m,2H),7.10-7.06(m,1H),7.03-6.96(m,1H),5.29(s,2H).

[1049] Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid

[1050] Under nitrogen atmosphere, 0.85 ml of 1.6 mol / l n-hexane solution of n-butyl lithium was added dropwise at -78°C to a solution of 360 mg of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole in 10 ml of tetrahydrofuran, and stirred at the same temperature for 10 minutes. After stirring, 1.0 g of dry ice was added to the reaction mixture at -78°C, and stirred at the same temperature for 5 minutes. After the reaction was completed, 10 ml of 1 mol / l hydrochloric acid aqueous solution was added to the reaction mixture, and extraction was performed with ethyl acetate (10 ml×2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using a mixture of n-hexane:ethyl acetate:acetic acid (gradient: 74:25:1 to 39:60:1) as the eluent to obtain 45 mg of the target product as a colorless solid with a melting point of 124-126°C.

[1051] Reference Example 4: Synthesis of 1-(2,4-dimethylphenyl)-3-ethoxypropane-2-amine

[1052] Step 1: Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-hydroxypropan-2-yl)carbamate

[1053] At room temperature, 2.7 g of sodium borohydride was added to 110 ml of a tetrahydrofuran solution of 11.5 g of ethyl 2-(tert-butoxycarbonylamino)-3-(2,4-dimethylphenyl)propanoate. After the addition was completed, 22 ml of methanol was added dropwise at 65°C and stirred at this temperature for 2 hours. After the reaction was completed, water was added to the reaction mixture at room temperature, and the solvent was distilled off under reduced pressure. Saturated brine was added to the obtained residue, and extraction was performed with ethyl acetate (50 ml × 2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 9.76 g of a crude product of the target substance as a colorless solid. The product was used directly in the next step without further purification.

[1054] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.07-6.91(m,3H),4.89-4.64(m,1H),3.93-3.74(m,1H),3 .74-3.49(m,2H),2.89-2.72(m,2H),2.43(br,1H),2.33(s,3H),2.29(s,3H),1.42(s,9H).

[1055] Step 2: Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-ethoxypropan-2-yl)carbamate

[1056] At room temperature, 2 ml of 50 mass % sodium hydroxide aqueous solution, 12 mg of tetrabutylammonium bromide, and 828 mg of diethyl sulfate were added to a mixed solution of 1.0 g of tert-butyl (1-(2,4-dimethylphenyl)-3-hydroxypropane-2-yl)carbamate and 20 ml of n-hexane, and stirred at 65°C for 5 hours. After the stirring was completed, the mixture was stirred for another 14 hours at room temperature, and then stirred for another 8 hours at 65°C. After the reaction was completed, 20 ml of water was added at room temperature, and then extracted with 10 ml of ethyl acetate. The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as the eluent to obtain 1.04 g of the target product as a colorless oil.

[1057] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.06-6.99(m,1H),6.98-6.88(m,2H),5.02-4.87(m,1H),3.94-3.76(m,1H),3.52 -3.38(m,2H),3.36-3.23(m,2H),2.90-2.75(m,2H),2.33(s,3H),2.28(s,3H),1.42(s,9H),1.21(t,J=6.9Hz,3H).

[1058] Step 3: Synthesis of 1-(2,4-dimethylphenyl)-3-ethoxypropane-2-amine

[1059] At room temperature, 5 ml of 35 mass % hydrochloric acid aqueous solution was added to a mixed solution of 1.04 g of (1-(2,4-dimethylphenyl)-3-ethoxypropane-2-yl)carbamic acid tert-butyl ester and 15 ml of 1,4-dioxane, and stirred at room temperature for 18 hours. After the reaction was completed, the solvent of the reaction mixture was distilled off under reduced pressure, and then 10 ml of water was added to the obtained residue, and washed with a mixed solution of 10 ml of n-hexane and 10 ml of ethyl acetate. 1 mol / l sodium hydroxide aqueous solution was added to the obtained water layer until the pH reached 10, and then extracted with 20 ml of ethyl acetate. The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 657 mg of the target product as a colorless oil.

[1060] 1H-NMR (CDCl3, Me4Si, 300MHz): δ7.06-6.90 (m, 3H), 3.56-3.39 (m, 3H), 3.31-3.15 (m, 2H), 2.80-2.69 (m, 1H), 2.57-2.46 (m, 1H), 2.29 (s, 6H), 1,21 (t, J = 6.9 Hz, 3H). No proton peak of NH2 was observed.

[1061] Reference Example 5: Synthesis of N-(2,4-dimethylphenyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide

[1062] To a mixed solution of 459 mg of 1-(tert-butyl)-N-(2,4-dimethylphenyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 5 ml of dichloromethane was added 1 ml of trifluoroacetic acid at room temperature, and the mixture was stirred at room temperature for 2 hours and 30 minutes. After the reaction was completed, the solvent of the reaction mixture was distilled off under reduced pressure, and then 10 ml of toluene was added to the obtained residue, and the solvent was distilled off again under reduced pressure. The obtained residue was washed with 3 ml of diisopropyl ether to obtain 131 mg of the target product as a white solid with a melting point of 132 to 134°C.

[1063] Reference Example 6: Synthesis of 1-(2,4-dimethylphenyl)-3-(methylthio)propane-2-amine

[1064] Step 1: Synthesis of 2-(tert-butoxycarbonylamino)-3-(2,4-dimethylphenyl)propyl 4-methylbenzenesulfonate

[1065] At room temperature, 4.09 g of p-toluenesulfonyl chloride was added to a mixed solution of 5.00 g of tert-butyl (1-(2,4-dimethylphenyl)-3-hydroxypropane-2-yl)carbamate, 1.76 g of N-methylimidazole, 2.17 g of triethylamine and 30 ml of toluene, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, 30 ml of water was added at room temperature, and extraction was performed with ethyl acetate (30 ml × 1 time). The obtained organic layer was washed with 1 mol / l hydrochloric acid, dehydrated / dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using ethyl acetate as the eluent. The obtained solid was washed with 20 ml of diisopropyl ether to obtain 5.20 g of the target product as a white solid with a melting point of 90 to 93°C.

[1066] Step 2: Synthesis of S-(2-(tert-butoxycarbonylamino)-3-(2,4-dimethylphenyl)propyl thioacetate

[1067] To a mixed solution of 1.90 g of 2-(tert-butoxycarbonylamino)-3-(2,4-dimethylphenyl)propyl 4-methylbenzenesulfonate and 9 ml of N,N-dimethylformamide was added 0.75 g of potassium thioacetate, and stirred at room temperature for 2 hours and 30 minutes. After the reaction was completed, 20 ml of water was added at room temperature, and extraction was performed with ethyl acetate (20 ml × 1 time). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.51 g of the target product as a yellow solid with a melting point of 92 to 94°C.

[1068] Step 3: Synthesis of tert-butyl (1-(2,4-dimethylphenyl)-3-(methylthio)propan-2-yl)carbamate

[1069] At room temperature, 0.93 g of methyl iodide was added to a mixed solution of 1.51 g of S-(2-(tert-butoxycarbonylamino)-3-(2,4-dimethylphenyl)propyl thioacetate, 1.21 g of potassium carbonate and 8 ml of methanol, and the mixture was stirred at room temperature for 1 hour and 30 minutes. After the reaction was completed, the solvent was distilled off under reduced pressure. 10 ml of water was added to the obtained residue, and extraction was performed with ethyl acetate (10 ml×1 time). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.28 g of the target product as a white solid with a melting point of 70 to 72°C.

[1070] Step 4: Synthesis of 1-(2,4-dimethylphenyl)-3-(methylthio)propane-2-amine

[1071] At room temperature, 35 mass % hydrochloric acid 3 ml was added to a mixed solution of 1.28 g of tert-butyl (1-(2,4-dimethylphenyl)-3-(methylthio)propane-2-yl)carbamate and 10 ml of 1,4-dioxane, and stirred at room temperature for 3 hours and 30 minutes. After the reaction was completed, the solvent was distilled off under reduced pressure. The obtained aqueous layer was washed with a mixed solution of n-hexane:ethyl acetate = 1:1 (volume ratio) (100 ml × 2 times). A 1 mol / l sodium hydroxide aqueous solution was added to the obtained aqueous layer until the pH reached 13, and then extracted with ethyl acetate (10 ml × 1 time). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.61 g of the target product.

[1072] 1H-NMR (CDCl3, Me4Si, 400MHz): δ7.07-6.89 (m, 3H), 3.21-3.28 (m, 1H), 2.92-2.39 (m, 4H), 2.29 (s, 6H), 2.11 (s, 3H). No NH2 proton peak was observed.

[1073] Reference Example 7: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036)

[1074] Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate (Compound No. ii-004)

[1075] At room temperature, 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were added to a mixed solution of 1.00 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid and 10 ml of acetone, and the mixture was stirred at room temperature for 3 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 20 ml of water was added to the obtained residue, and then extracted with ethyl acetate (20 ml × 2 times). The obtained organic layer was dehydrated / dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.90 g of the target product as a yellow solid with a melting point of 69 to 71°C.

[1076] Step 2: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid methyl ester (Compound No. ii-005)

[1077] Under nitrogen atmosphere, 0.10 g of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (2-valent) was added to a mixed solution of 0.50 g of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxane, 0.92 g of cesium carbonate and 10 ml of 1,4-dioxane at room temperature, and then stirred at 100°C for 16 hours. After the reaction was completed, 20 ml of water was added to the reaction mixture, and extraction was performed with ethyl acetate (20 ml × 3 times). After dehydration / drying with saturated brine and then with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solution of n-hexane:ethyl acetate (mixing gradient of 10:0 to 9:1) as an eluent to obtain 0.30 g of the target product as a yellow oil.

[1078] 1H-NMR (CDCl3, Me4Si, 400MHz): δ7.24(s,1H),7.20-7.13(m,1H),6.90-6.85(m,1H),6.84-6.76(m,2H),3.77(s,3H),2.33(s,3H),1.72(s,3H).

[1079] Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036)

[1080] At room temperature, to a mixed solution of 39.0 g of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid methyl ester and 100 ml of methanol, a mixed solution of 27.1 g of sodium hydroxide and 100 ml of water was added, and stirred at 45°C for 16 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. 50 ml of water was added to the obtained residue, and then a 35% by mass aqueous hydrochloric acid solution was added until the pH reached 2, and the precipitated solid was filtered out. The obtained solid was dried under reduced pressure and then washed with 100 ml of n-hexane to obtain 37.0 g of the target product, which was a white solid with a melting point of 116 to 118°C.

[1081] The compounds of the present invention can be synthesized according to the above-mentioned synthesis examples and reference examples. Examples of pyrazole compounds included in the present invention prepared in the same manner as in Synthesis Examples 1 to 7 are shown in Tables 1 to 7, and examples of manufacturing intermediates prepared in the same manner as in Reference Examples 1 to 6 are shown in Tables 8 to 9, but the pyrazole compounds and manufacturing intermediates included in the present invention are not limited thereto.

[1082] The substituents written as "Me" in the table represent "methyl", and "Et" written in the same manner below represents "ethyl", "nPr" represents "n-propyl", "nBu" represents "n-butyl", "tBu" represents "tert-butyl", "iBu" represents "isobutyl", "iPr" represents "isopropyl", "cPr" represents "cyclopropyl", "cHx" represents "cyclohexyl", "Ph" represents "phenyl", and "Bn" represents "benzyl". In addition, "*" means that the compound is an oily substance with no melting point or a resinous compound, "**" means that the compound decomposes when subjected to a melting point measurement, and "mp" represents a melting point (in ° C). In addition, ">" in the table represents a temperature higher than that. For example, ">300" in the table means that the compound subjected to a melting point measurement did not melt at 300 ° C.

[1083] In addition, the "4-" in "4-Me-Ph" recorded in the table, for example, refers to the substitution position on the phenyl group. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl. For another example, the "4-" in "1-Me-Ph" refers to the substitution position on the phenyl group. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl.

[1084] [Chemical formula 31]

[1085]

[1086] In addition, the substituents represented by E-2a, E-3a, E-4a, E-5a, E-7a, E-11a, E-12a, E-13a, E-14a, E-21a, E-22a, E-23a, E-24a, E-30a, E-31a, E-41a, F-3a, F-10a, F-11a, L-1 to L-4, Z-1a, Z-1b, Z-1c, Z-1d, Z-2a, Z-3a, Z-4a, Z-4b and Z-6a respectively represent the following structures.

[1087] [Chemical formula 32]

[1088]

[1089] [Chemical formula 33]

[1090]

[1091] [Chemical formula 34]

[1092]

[1093] [Chemical formula 35]

[1094]

[1095] In addition, the numbers in the above structural formulas indicate the substitution positions. For example, "6-OMe-(E-3a)" in the table represents the following structure. A structural formula without a substituent indicates that there is no substitution.

[1096] [Chemical formula 36]

[1097]

[1098] [Table 1]

[1099] [Chemical formula 37]

[1100]

[1101]

[1102]

[1103] [Table 2]

[1104] [Chemical formula 38]

[1105]

[1106]

[1107]

[1108]

[1109]

[1110]

[1111]

[1112]

[1113]

[1114]

[1115]

[1116]

[1117]

[1118]

[1119] [Table 3]

[1120] [Chemical formula 39]

[1121]

[1122]

[1123]

[1124] [Table 4]

[1125] [Chemical formula 40]

[1126]

[1127]

[1128]

[1129]

[1130]

[1131]

[1132] [Table 5]

[1133] [Chemical formula 41]

[1134]

[1135]

[1136] [Table 6]

[1137] [Chemical formula 42]

[1138]

[1139]

[1140] [Table 7]

[1141] [Chemical formula 43]

[1142]

[1143]

[1144] [Table 8]

[1145] [Chemical formula 44]

[1146]

[1147]

[1148] [Table 9]

[1149] [Chemical formula 45]

[1150]

[1151]

[1152]

[1153]

[1154] [Table 10]

[1155] [Chemical formula 46]

[1156]

[1157]

[1158] Compounds of the present invention listed in Tables 1 to 8 for which melting points are not listed 1 H-NMR data are shown in Table 11. Here, the following data are data measured in deuterated chloroform, and "#1" refers to data measured at 300 MHz (model; JNM-ECX300 or JNM-ECP300; manufactured by JEOL), and similarly, "#2" refers to data measured at 400 MHz (model; JNM-ECZ400S; manufactured by JEOL).

[1159] [Table 11]

[1160]

[1161]

[1162]

[1163]

[1164]

[1165]

[1166]

[1167]

[1168]

[1169]

[1170]

[1171]

[1172]

[1173]

[1174]

[1175]

[1176]

[1177]

[1178]

[1179]

[1180]

[1181]

[1182]

[1183]

[1184]

[1185]

[1186]

[1187]

[1188]

[1189]

[1190]

[1191]

[1192]

[1193]

[1194]

[1195]

[1196]

[1197] [Test example]

[1198] Next, the usefulness of the compounds of the present invention as pest control agents is specifically described in the following test examples, but the present invention is not limited thereto. Here, "RH" in the test examples refers to relative humidity, for example, "humidity 100% RH" means that the relative humidity is 100%.

[1199] (Preparation of test solution)

[1200] The compound of the present invention was dissolved in an emulsified white sample (a mixture of Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone and Solvesso (registered trademark) 200 (manufactured by ExxonMobil Corporation) [1:5:28 (weight ratio)), and emulsions with concentrations of 1 mass %, 5 mass %, and 20 mass % were prepared, respectively. These emulsions were used as test solutions in the following Test Examples 1 to 7.

[1201] Test Example 1: Experiment on the control effect of wheat husk blight

[1202] At 90cm 3 Wheat (variety name: HARAYUTAKA) was planted in a plastic pot, and at the 1.3 leaf stage, the test solution was diluted with water to prepare a 500 ppm solution and 5 ml of it was sprayed. One day after the spraying, the conidia suspension of wheat blight fungus (Septorianodorum) was sprayed on the wheat and placed in an inoculation box at a temperature of 20°C and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 20°C, humidity 80% RH) and kept for 8 days. The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the following calculation formula.

[1203] Control value = [1-(lesion area ratio of treated area / lesion area ratio of untreated area)] × 100

[1204] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1205] Compound No.: 1-005, 1-006, 1-008, 1-024, 2-001, 2-004, 2-008, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015, 2-016, 2-018, 2-019, 2-020, 2-021, 2-022, 2-0 23, 2-024, 2-026, 2-027, 2-029, 2-030, 2-031, 2-032, 2-033, 2-036, 2-040, 2-043, 2-048, 2-050, 2-056, 2-059, 2-063, 2-077, 2-088, 2-091, 2-092, 2- 093, 2-094, 2-095, 2-096, 2-098, 2-103, 2-105, 2-107, 2-114, 2-120, 2-121, 2-122, 2-129, 2-130, 2-131, 2-132, 2-133, 2-135, 2-141, 2-142, 2-143, 2-146, 2-147, 2-148, 2-149, 2-151, 2-154, 2-156, 2-157, 2-158, 2-164, 2-165, 2-166, 2-167, 2-168, 2-171, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182 ,2-183,2-184,2-185,2-186,2-187,2-188,2-189,2-190,2-191,2-192,2-193,2-194,2-195,2-196,2-197,2-198,2-199,2-200,2-201,2-202,2-2 03, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-227, 2- 228, 2-229, 2-230, 2-231, 2-232, 2-233, 2-235, 2-236, 2-237, 2-238, 2-239, 2-240, 2-241, 2-242, 2-243, 2-250, 2-256, 2-270, 2-271, 2-272, 2-273, 2 -274, 2-275, 2-276, 2-277, 2-278, 2-279, 2-280, 2-281, 2-282, 2-283, 2-284, 2-285, 2-286, 2-287, 2-288, 2-289, 2-290, 2-291, 2-292, 2-293, 2-294,2-295, 2-296, 2-297, 2-298, 2-299, 2-300, 2-302, 2-303, 2-304, 2-305, 2-306, 2-307, 2-309, 2-311, 2-313, 2-314, 2-315, 2-317, 2-318, 2-320, 2-321, 2-324, 2-325, 2-326, 2-327, 2-328, 2-329, 2-330, 2-331, 2-332, 2-333, 2-334, 2-335, 2-336, 2-343, 2-345, 2-347, 2-351, 2-352, 2-359, 2-360 60. 2-361, 2-362, 4-005, 4-010, 4-016, 4-020, 4-022, 4-029, 4-030, 4-032, 4-039, 4-040, 4-041, 4-042, 4-046, 4-047, 4-053, 4-059, 4-060, 4-061, 4-064, 4-067, 4-076, 4-078, 4-079, 4-084, 4-085, 4-087, 4-089, 4-090, 4-092, 4-093, 4-094, 4-095, 4-096, 4-097, 4-098, 6-001, 7-001, 7-003. ,

[1206] Test Example 2 Test on the effect of controlling tomato powdery mildew

[1207] At 90cm 3 Tomatoes (variety name: Momotaro) were planted in plastic pots of , and at the 2-leaf stage, the test solution was diluted with water to prepare a 500 ppm solution and 5 ml of the solution was sprayed. After air drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and sprayed with a conidia suspension of tomato powdery mildew (Leveillula taurica). After 14 days, the proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated using the same calculation formula as in Test Example 1.

[1208] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1209] Compound No.: 1-001, 1-002, 1-003, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-024, 1-025, 1-027, 1-028, 1-029, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 2-001, 2-002, 2-003, 2-004, 2-005, 2-006, 2- 007, 2-008, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047, 2-048, 2-049, 2-050, 2-051 ,2-052,2-053,2-055,2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-064,2-065,2-066,2-067,2-068,2-069,2-070,2-071,2-072,2-0 75, 2-076, 2-077, 2-078, 2-080, 2-081, 2-082, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-101, 2- 102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2 -123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143,2-144、2-145、2-146、2-147、2-148、2-149、2-150、2-151、2-152、2-153、2-154、2-155、2-156、2-157、2-158、2-159、2-160、2-161、2-162、2-163、2-164、2-165、2-166、2-167、2-168、2-169、2-170、2-171、2-172、2-173、2-175、2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-187、2-188、2-189、2-190、2-191、2-192、2-193、2-194、2-195、2-196、2-197、2-198、2-199、2-200、2-201、2-202、2-203、2-204、2-205、2-206、2-207、2-208、2-209、2-210、2-211、2-212、2-213、2-214、2-215、2-216、2-217、2-218、2-219、2-220、2-221、2-222、2-223、2-224、2-225、2-226、2-227、2-228、2-229、2-230、2-231、2-232、2-233、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-242、2-243、2-244、2-247、2-248、2-249、2-250、2-251、2-252、2-253、2-254、2-255、2-256、2-257、2-258、2-259、2-260、2-261、2-262、2-263、2-264、2-265、2-266、2-267、2-268、2-269、2-270、2-271、2-272、2-273、2-274、2-275、2-276、2-277、2-278、2-279、2-280、2-281、2-282、2-283、2-284、2-285、2-286、2-287、2-288、2-289、2-290、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-305、2-306、2-307、2-308、2-309、2-310、2-311、2-312、2-313、2-314, 2-315, 2-316, 2-317, 2-318, 2-319, 2-320, 2-321, 2-322, 2-323, 2-324, 2-325, 2-326, 2-327, 2-328, 2-329, 2-330, 2-331, 2-332, 2-333, 2-334, 2-335, 2-336, 2-337, 2-338, 2-339, 2-340, 2-341, 2-342, 2-343, 2-344, 2-345, 2-346, 2-347, 2-348, 2-349, 2-350, 2-351 51, 2-352, 2-353, 2-354, 2-356, 2-357, 2-358, 2-359, 2-360, 2-361, 2-362, 3-001, 3-002, 3-003, 3-004, 3-005, 3-006, 3-007, 3-008, 3-009, 3-010, 3-011, 3-012, 4-001, 4-002, 4-003, 4-005, 4-010, 4-016, 4-020, 4-021, 4-022, 4-024, 4-025, 4-026, 4-027, 4-028, 4-029, 4-030, 4-031, 4-032, 4-033, 4-035, 4-036, 4-037, 4-038, 4-039, 4-040, 4-041, 4-042, 4-045, 4-046, 4-047, 4-048, 4-049, 4-050, 4-051, 4-052, 4-053, 4-054, 4-055, 4-056, 4-057, 4-058, 4-059, 4-060, 4-061, 4-062, 4-063, 4-064, 4-067, 4-070, 4-071, 4-072, 4-076, 4-077 77, 4-078, 4-079, 4-081, 4-082, 4-084, 4-085, 4-086, 4-087, 4-088, 4-089, 4-090, 4-091, 4-092, 4-093, 4-094, 4-095, 4-096, 4-097, 4-098, 4-099, 4-101, 4-102, 4-103, 5-001, 6-001, 6-002, 6-003, 7-001, 7-002, 7-003, 7-004, 7-006, 7-007, 8-001, 8-002, 8-003, 8-005.

[1210] Test Example 3: Cucumber gray mold control effect test

[1211] At 90cm 3Cucumbers (variety name: SHIMOSHIRAZUJIBAI) were planted in plastic pots. At the cotyledon stage, the test solution was diluted with water to prepare a 500ppm solution and 5ml of spray treatment was performed, and air-dried. After that, the treated leaves were cut and placed in a plastic container. The conidia suspension of cucumber gray mold (Botrytis cinerea) was mixed with the dissolved PDA culture medium in a ratio of 1:1 (volume ratio), and 30μl was dripped on the treated leaves each time for inoculation. After inoculation, it was placed at 20°C and humid (humidity 100% RH) for 3 days. After that, the proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the same calculation formula as in Test Example 1.

[1212] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1213] Compound No.: 1-002, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-014, 1-016, 1-017, 1-018, 1-022, 1-024, 1-025, 1-026, 1-028, 1-029, 1-031, 1-0 32, 1-033, 1-034, 1-035, 1-036, 2-001, 2-004, 2-008, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015, 2-016, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2- 024, 2-025, 2-026, 2-027, 2-029, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047, 2-048, 2-049, 2-050, 2-051, 2-052, 2-055, 2-056, 2-057, 2-058, 2-059, 2-060, 2-061, 2-062, 2-063, 2-064, 2-065, 2-066, 2-067, 2-068, 2-070, 2-071, 2-072, 2-075 , 2-076, 2-077, 2-078, 2-080, 2-081, 2-082, 2-087, 2-088, 2-089, 2-090, 2-091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-101, 2-1 02, 2-103, 2-104, 2-105, 2-106, 2-107, 2-109, 2-110, 2-111, 2-113, 2-114, 2-115, 2-116, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-129, 2-130, 2- 131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2 -152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-160, 2-161, 2-164, 2-165, 2-166, 2-167, 2-168, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-176,2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-187、2-188、2-189、2-190、2-191、2-192、2-193、2-194、2-195、2-196、2-197、2-198、2-199、2-200、2-201、2-202、2-203、2-204、2-205、2-206、2-207、2-208、2-209、2-210、2-211、2-212、2-213、2-214、2-215、2-216、2-217、2-218、2-219、2-220、2-221、2-222、2-223、2-224、2-225、2-226、2-227、2-228、2-229、2-230、2-231、2-232、2-233、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-242、2-243、2-244、2-246、2-247、2-248、2-249、2-250、2-251、2-252、2-253、2-254、2-255、2-256、2-257、2-258、2-259、2-260、2-261、2-262、2-263、2-264、2-265、2-266、2-267、2-268、2-269、2-270、2-271、2-272、2-273、2-274、2-275、2-276、2-277、2-278、2-279、2-280、2-281、2-282、2-283、2-284、2-285、2-286、2-287、2-288、2-289、2-290、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-305、2-306、2-307、2-308、2-309、2-310、2-311、2-313、2-314、2-315、2-316、2-317、2-318、2-319、2-320、2-321、2-322、2-323、2-324、2-325、2-326、2-327、2-328、2-329、2-330、2-331、2-332、2-333、2-334、2-335、2-336、2-337、2-338、2-339、2-340、2-341、2-342、2-343、2-344、2-345, 2-346, 2-347, 2-348, 2-349, 2-350, 2-351, 2-352, 2-353, 2-354, 2-355, 2-356, 2-357, 2-358, 2-359, 2-360, 2-361, 2-362, 3-001, 3-007, 3-008, 4-001, 4-002, 4-003, 4-004, 4-005, 4-007, 4-009, 4-001 10. 4-014, 4-016, 4-019, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-026, 4-027, 4-029, 4-030, 4-031, 4-032, 4-033, 4-035, 4-036, 4-037, 4-038, 4-039, 4-040, 4-041, 4-042, 4-043, 4-045, 4-046, 4-047, 4-049, 4-050, 4-052, 4-053, 4-054, 4-057, 4-058, 4-059, 4-060, 4-061, 4-064, 4-065, 4-066, 4-067, 4-068, 4-069, 4-070, 4-071, 4-072, 4-073, 4-074, 4-076, 4-077, 4-078, 4-079, 4-081, 4-082, 4-083, 4-084 84, 4-085, 4-086, 4-087, 4-089, 4-090, 4-091, 4-092, 4-093, 4-094, 4-095, 4-096, 4-097, 4-098, 4-099, 4-102, 4-103, 5-002, 6-001, 6-002, 7-001, 7-002, 7-003, 7-004, 7-007, 8-001, 8-002, 8-003, 8-005.

[1214] Test Example 4: Test on the effect of preventing and controlling cucumber sclerotinia

[1215] At 90cm 3Cucumbers (variety name: SHIMOSHIRAZUJIBAI) were planted in plastic pots, and at the cotyledon stage, the test solution was diluted with water to prepare a 500ppm solution and 5ml of it was sprayed and air-dried. After that, the treated leaves were placed in a plastic container. A bacterial agar piece (5mm in diameter) of cucumber sclerotinia sclerotiorum that had been cultured in advance on PDA medium was inoculated on the cotyledons of the cucumber treated with the agent. After inoculation, the plastic container was covered with a vinyl plastic film to humidify (humidity 100% RH) and placed at 20°C for 2 days. After that, the proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the same calculation formula as in Test Example 1.

[1216] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1217] Compound No.: 1-002, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-014, 1-015, 1-016, 1-017, 1-018, 1-020, 1-024, 1-025, 1-026, 1-028, 1-029, 1-0 31, 1-032, 1-033, 1-034, 1-035, 1-036, 1-038, 2-001, 2-003, 2-004, 2-008, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015, 2-016, 2-018, 2-019, 2-020, 2- 021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-028, 2-029, 2-030, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047, 2-048, 2-049, 2-050, 2-051, 2-052, 2-055, 2-056, 2-057, 2-058, 2-059, 2-060, 2-061, 2-062, 2-063, 2-064, 2-065, 2-066, 2-067 ,2-068,2-069,2-070,2-071,2-072,2-075,2-076,2-077,2-078,2-080,2-081,2-087,2-088,2-089,2-090,2-091,2-092,2-093,2-094,2-095,2-0 96, 2-097, 2-098, 2-099, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2- 119, 2-120, 2-121, 2-122, 2-123, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-140, 2-141, 2-142, 2-143, 2-144, 2-146, 2 -147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-162, 2-164, 2-165, 2-166, 2-167, 2-168,2-169、2-171、2-172、2-173、2-174、2-175、2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-187、2-188、2-189、2-190、2-191、2-192、2-193、2-194、2-195、2-196、2-197、2-198、2-199、2-200、2-201、2-202、2-203、2-204、2-205、2-206、2-207、2-208、2-209、2-210、2-211、2-212、2-213、2-214、2-215、2-216、2-217、2-218、2-219、2-220、2-221、2-222、2-223、2-224、2-225、2-226、2-227、2-228、2-229、2-230、2-231、2-232、2-233、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-242、2-243、2-244、2-246、2-247、2-248、2-249、2-250、2-251、2-252、2-253、2-254、2-255、2-256、2-257、2-258、2-259、2-260、2-261、2-262、2-263、2-264、2-265、2-266、2-267、2-268、2-269、2-270、2-271、2-272、2-273、2-274、2-275、2-276、2-277、2-278、2-279、2-280、2-281、2-282、2-283、2-284、2-285、2-286、2-287、2-288、2-289、2-290、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-305、2-306、2-307、2-309、2-310、2-311、2-312、2-313、2-314、2-315、2-316、2-317、2-318、2-320、2-321、2-322、2-323、2-324、2-325、2-326、2-327、2-328、2-329、2-330、2-331、2-332、2-333、2-334、2-335、2-336、2-337、2-338、2-339、2-340, 2-341, 2-342, 2-343, 2-344, 2-345, 2-346, 2-347, 2-348, 2-349, 2-350, 2-351, 2-352, 2-353, 2-354, 2-355, 2-356, 2-358, 2-359, 2-360, 2-361, 2-362, 3-001, 3-002, 3-003, 3-004, 3-005, 3-006, 3-008, 3-010, 3-011, 3-012, 4-0 01, 4-002, 4-005, 4-007, 4-008, 4-009, 4-010, 4-011, 4-014, 4-016, 4-017, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-026, 4-027, 4-029, 4-030, 4-031, 4-032, 4-033, 4-035, 4-036, 4-037, 4-038, 4-039, 4-040, 4-041, 4-042, 4-043, 4-045, 4-046, 4-047, 4-048, 4-049, 4-050, 4-051, 4-052, 4-053, 4-054, 4-056, 4-057, 4-058, 4-059, 4-060, 4-061, 4-062, 4-064, 4-065, 4-066, 4-067, 4-068, 4-069, 4-070, 4-071, 4-072, 4-073, 4-074, 4-076, 4-077, 4-078, 4-079, 4-080 81, 4-082, 4-083, 4-084, 4-085, 4-086, 4-087, 4-088, 4-089, 4-090, 4-091, 4-092, 4-093, 4-094, 4-095, 4-096, 4-097, 4-098, 4-099, 4-100, 4-101, 4-102, 4-103, 6-001, 7-001, 7-002, 7-003, 7-004, 7-007, 8-001, 8-002, 8-003, 8-005.

[1218] Test Example 5: Test on the effect of preventing and controlling cucumber powdery mildew

[1219] At 90cm 3Cucumbers (variety name: SHIMOSHIRAZUJIBAI) were planted in plastic pots. At the cotyledon stage, the test solution was diluted with water to prepare a 500 ppm solution and 5 ml of the solution was sprayed. After air drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and sprayed with a conidia suspension of cucumber powdery mildew (Erysiphe polygoni). After 9 days, the proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the same calculation formula as in Test Example 1.

[1220] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1221] Compound No.: 1-002, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-014, 1-016, 1-024, 1-028, 1-029, 1-032, 1-034, 1-035, 1-036, 2-001, 2-004, 2-007, 2-0 08, 2-009, 2-010, 2-012, 2-013, 2-014, 2-015, 2-016, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-029, 2-030, 2-031, 2- 032, 2-033, 2-034, 2-035, 2-036, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047, 2-048, 2-050, 2-056, 2-057, 2-058, 2-059, 2-060, 2-061, 2-062, 2-063, 2-064, 2-065, 2-066, 2-067, 2-069, 2-070, 2-071, 2-072, 2-075, 2-076, 2-077, 2-078, 2-080, 2-081, 2-082, 2-087, 2-088, 2-089, 2-091 ,2-092,2-093,2-094,2-095,2-096,2-097,2-098,2-099,2-101,2-102,2-103,2-104,2-105,2-107,2-109,2-110,2-111,2-112,2-113,2-114,2-1 15, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2- 141, 2-142, 2-143, 2-144, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-159, 2-160, 2-161, 2-163, 2 -164, 2-165, 2-166, 2-167, 2-168, 2-170, 2-171, 2-172, 2-173, 2-175, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187,2-188、2-189、2-190、2-191、2-192、2-193、2-194、2-195、2-196、2-197、2-198、2-199、2-200、2-201、2-202、2-203、2-204、2-205、2-206、2-207、2-208、2-209、2-210、2-211、2-212、2-213、2-214、2-215、2-216、2-217、2-218、2-219、2-220、2-221、2-222、2-223、2-224、2-225、2-226、2-227、2-228、2-229、2-230、2-231、2-232、2-233、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-242、2-243、2-244、2-247、2-248、2-249、2-250、2-251、2-252、2-253、2-254、2-256、2-257、2-258、2-259、2-260、2-261、2-262、2-263、2-264、2-265、2-266、2-267、2-268、2-270、2-271、2-272、2-273、2-274、2-275、2-276、2-277、2-278、2-279、2-280、2-281、2-282、2-283、2-284、2-285、2-286、2-287、2-288、2-289、2-290、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-305、2-306、2-307、2-308、2-309、2-310、2-311、2-313、2-314、2-315、2-316、2-317、2-318、2-320、2-321、2-322、2-324、2-325、2-326、2-327、2-328、2-329、2-330、2-331、2-332、2-333、2-334、2-335、2-336、2-338、2-339、2-342、2-343、2-345、2-346、2-347、2-348、2-351、2-352、2-353、2-354、2-355、2-356、2-357、2-358、2-359、2-360、2-361、2-362、3-001、3-002、3-003、3-004、3-005, 3-006, 3-007, 3-010, 3-011, 4-005, 4-010, 4-016, 4-020, 4-021, 4-022, 4-023, 4-024, 4-025, 4-026, 4-028, 4-029, 4-030, 4-031, 4-032, 4-033 3, 4-034, 4-035, 4-036, 4-037, 4-038, 4-039, 4-040, 4-041, 4-042, 4-045, 4-046, 4-047, 4-049, 4-050, 4-052, 4-053, 4-054, 4-057, 4-058, 4-059, 4-060 60, 4-061, 4-062, 4-064, 4-066, 4-067, 4-068, 4-070, 4-071, 4-076, 4-077, 4-078, 4-079, 4-081, 4-084, 4-085, 4-086, 4-087, 4-089, 4-090, 4-091, 4 -092, 4-093, 4-094, 4-095, 4-096, 4-097, 4-098, 4-099, 4-102, 4-103, 6-001, 6-002, 7-001, 7-002, 7-003, 7-004, 7-007, 8-001, 8-002, 8-003, 8-005.

[1222] Test Example 6: Test on the effect of preventing and controlling cucumber anthracnose

[1223] At 90cm 3 Cucumbers (variety name: SHIMOSHIRAZUJIBAI) were planted in plastic pots, and at the cotyledon stage, the test solution was diluted with water and prepared into 500ppm solution and 5ml spraying treatment was carried out. One day after spraying, the conidia suspension of cucumber anthracnose (Colletotrichum lagenarium) was sprayed on the cucumbers and placed in an inoculation box at a temperature of 25°C and a humidity of 100%RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 23°C, humidity 60%RH) and kept for 7 days. The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the same calculation formula as in Test Example 1.

[1224] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1225] Compound No.: 1-001, 1-002, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-029, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 2-001, 2-002, 2-003, 2- 004, 2-006, 2-007, 2-008, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 2-047 ,2-048,2-049,2-050,2-052,2-053,2-055,2-056,2-057,2-058,2-059,2-060,2-061,2-062,2-063,2-064,2-065,2-066,2-067,2-068,2-069,2-0 70, 2-071, 2-072, 2-073, 2-074, 2-075, 2-076, 2-077, 2-078, 2-079, 2-080, 2-081, 2-082, 2-083, 2-084, 2-085, 2-086, 2-087, 2-088, 2-089, 2-090, 2- 091, 2-092, 2-093, 2-094, 2-095, 2-096, 2-097, 2-098, 2-099, 2-100, 2-101, 2-102, 2-104, 2-107, 2-109, 2-114, 2-115, 2-116, 2-118, 2-119, 2-120, 2 -121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141,2-142、2-143、2-144、2-145、2-146、2-147、2-148、2-149、2-150、2-151、2-152、2-153、2-154、2-155、2-156、2-157、2-158、2-159、2-160、2-161、2-162、2-163、2-164、2-165、2-166、2-167、2-168、2-169、2-170、2-171、2-172、2-173、2-174、2-175、2-176、2-177、2-178、2-179、2-180、2-181、2-182、2-183、2-184、2-185、2-186、2-187、2-188、2-189、2-190、2-191、2-192、2-193、2-194、2-195、2-196、2-197、2-198、2-199、2-200、2-201、2-202、2-203、2-204、2-205、2-206、2-207、2-208、2-209、2-210、2-211、2-212、2-213、2-214、2-215、2-216、2-217、2-218、2-219、2-220、2-221、2-222、2-223、2-224、2-225、2-226、2-227、2-228、2-229、2-230、2-231、2-232、2-233、2-234、2-235、2-236、2-237、2-238、2-239、2-240、2-241、2-242、2-243、2-244、2-245、2-246、2-247、2-249、2-250、2-251、2-252、2-253、2-256、2-257、2-258、2-259、2-261、2-262、2-263、2-264、2-265、2-266、2-267、2-268、2-269、2-270、2-271、2-272、2-273、2-274、2-275、2-276、2-277、2-278、2-279、2-280、2-281、2-282、2-283、2-284、2-285、2-286、2-287、2-288、2-289、2-290、2-291、2-292、2-293、2-294、2-295、2-296、2-297、2-298、2-299、2-300、2-301、2-302、2-303、2-304、2-305、2-306、2-307、2-308、2-309、2-310、2-311、2-312、2-313、2-314、2-315、2-316、2-317、2-318、2-319、2-320、2-321、2-322、2-323、2-324、2-325、2-326、2-327、2-328、2-329、2-330、2-331、2-332、2-333、2-334、2-335、2-336、2-337、2-338、2-339、2-340、2-341、2-342、2-343、2-344、2-345、2-346、2-347、2-348、2-349、2-350、2-351、2-352、2-353、2-354、2-355、2-356、2-357、2-358、2-359、2-360、2-361、2-362、3-001、3-002、3-003、3-004、3-005、3-006、3-007、3-008、3-009、3-010、3-011、3-012、4-001、4-002、4-003、4-004、4-005、4-006、4-007、4-009、4-010、4-011、4-012、4-013、4-014、4-015、4-016、4-017、4-019、4-020、4-021、4-022、4-023、4-024、4-025、4-026、4-027、4-028、4-029、4-030、4-031、4-032、4-033、4-034、4-035、4-036、4-037、4-038、4-039、4-040、4-041、4-042、4-043、4-044、4-045、4-046、4-047、4-048、4-049、4-050、4-051、4-052、4-053、4-054、4-055、4-056、4-057、4-058、4-059、4-060、4-061、4-062、4-063、4-064、4-065、4-066、4-067、4-068、4-069、4-070、4-071、4-072、4-073、4-074、4-075、4-076、4-077、4-078、4-079、4-080、4-081、4-082、4-083、4-084、4-085、4-086、4-087、4-088、4-089、4-090、4-091、4-092、4-093、4-094、4-095、4-096、4-097、4-098、4-099、4-100、4-101、4-102、4-103、5-001、5-002、6-001, 6-002, 6-003, 7-001, 7-002, 7-003, 7-004, 7-005, 7-006, 7-007, 8-001, 8-002, 8-003, 8-004, 8-005.

[1226] Test Example 7: Soybean rust control effect test

[1227] At 90cm 3 Soybeans (variety name: ENREI) were planted in plastic pots, and at the single-leaf stage, the test solution was diluted with water to prepare a 500 ppm solution and 5 ml of the solution was sprayed. One day after the spraying, the soybeans were spray-inoculated with a conidia suspension of soybean rust fungus (Phakopsora pachyrhizi) and placed in an inoculation box at a temperature of 20°C and a humidity of 100% RH for 2 days. After that, it was placed in an air-conditioned greenhouse (temperature 20°C, humidity 60% RH) and kept for 10 days. The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the same calculation formula as in Test Example 1.

[1228] As a result, among the tested compounds, the following compounds showed a control value of 70% or more.

[1229] Compound No.: 1-001, 1-005, 1-007, 1-008, 1-009, 1-010, 1-012, 1-016, 1-017, 1-020, 1-021, 1-022, 1-023, 1-024, 1-025, 1-027, 1-030, 1-035, 1-037, 1-0 38, 2-001, 2-010, 2-012, 2-013, 2-014, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-023, 2-024, 2-029, 2-030, 2-038, 2-040, 2-043, 2-048, 2-053, 2- 079, 2-081, 2-084, 2-085, 2-088, 2-093, 2-121, 2-122, 2-123, 2-125, 2-142, 2-143, 2-144, 2-145, 2-147, 2-148, 2-149, 2-150, 2-153, 2-155, 2-157, 2-163, 2-165, 2-166, 2-170, 2-171, 2-172, 2-173, 2-174, 2-176, 2-179, 2-180, 2-181, 2-182, 2-190, 2-201, 2-203, 2-218, 2-220, 2-221, 2-222, 2-223 , 2-224, 2-226, 2-227, 2-228, 2-229, 2-231, 2-234, 2-235, 2-236, 2-238, 2-239, 2-241, 2-245, 2-246, 2-247, 2-248, 2-249, 2-252, 2-256, 2-257, 2-2 59, 2-262, 2-263, 2-265, 2-266, 2-270, 2-278, 2-281, 2-282, 2-285, 2-288, 2-292, 2-300, 2-301, 2-302, 2-303, 2-304, 2-305, 2-306, 2-309, 2-310, 2- 311, 2-312, 2-314, 2-316, 2-317, 2-319, 2-361, 2-362, 3-001, 3-004, 3-005, 3-006, 3-011, 4-001, 4-004, 4-005, 4-006, 4-021, 4-025, 4-034, 4-035, 4 -039, 4-042, 4-047, 4-049, 4-050, 4-051, 4-054, 4-057, 4-062, 4-063, 4-066, 4-067, 4-068, 4-070, 4-074, 4-078, 4-079, 4-080, 4-081, 4-082, 4-084,4-085, 4-086, 4-087, 4-088, 4-090, 4-092, 4-095, 4-096, 4-098, 6-001, 7-002, 7-004, 7-005, 7-006, 8-001, 8-005.

[1230] (Industrial Applicability)

[1231] The pyrazole compound of the present invention exhibits excellent pest control activity, especially fungicidal activity, and has almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects, and is therefore an extremely useful compound.

Claims

1. A pyrazole compound or a salt thereof, which is represented by formula (1), In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula, G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R', About G 1 The relationship between them, when m5 represents an integer of 2, 3, 4 or 5, allows each G 1 Same or different from each other, R b Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R', R represents a hydrogen atom or a C1-C6 alkyl group, R' represents a C1-C6 alkyl group, T represents an oxygen atom or a sulfur atom, R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4, R X -1~R X -4 represent the structures shown in the following structural formulas, X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group, About X 1 The relationship between them allows each X to 1 Same or different from each other, About X 1 The relationship between them allows each X to 1 Same or different from each other, R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R', R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group, R 1 represents a hydrogen atom or a C1-C6 alkyl group, R 2 represents a hydrogen atom or a C1-C6 alkyl group, R 3 represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group, R 4 represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group, R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1. R a -2. R a -3. R a -4. R a -5 or R a -6, R a -1. R a -2. R a -3. R a -4. R a -5 and R a -6 represent the structures shown in the following structural formulas, R 5 represents a hydrogen atom or a C1-C6 alkyl group, R 6 represents a hydrogen atom or a C1-C6 alkyl group, In r 1 In the case of the integer 2, two R 5 and two R 6 Same or different from each other, R 7 Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl or phenyl, R 8 represents a hydrogen atom or a C1-C6 alkyl group, R 9 represents a hydrogen atom or a C1-C6 alkyl group, Z represents Z-1, Z-2, Z-3, Z-4, Z-5, Z-6 or Z-7, Z-1 to Z-7 represent the following structures respectively: in, Z 1 The substitution position refers to substitution on the aromatic rings of Z-1 to Z-7. Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, R i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, E-1 to E-54, F-1 to F-15 or -C(=NOR)R', About Z 1 The relationship between them, when n3 represents an integer of 2 or 3, allows each Z 1 Same or different from each other, About Z 1 The relationship between n5 and Z is such that when n5 represents an integer of 2, 3, 4 or 5, each Z 1 Same or different from each other, About Z 1 The relationship between n7 and 7 is that when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z is allowed to 1 Same or different from each other, R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, E-1-E-54, F-1-F-15 or C1-C6 alkylaminocarbonyl, R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6 alkyl)aminocarbonyl, E-1-E-54, F-1-F-15 or -C(=NOR)R', R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, benzyloxy, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino, R f represents C1-C6 alkyl, C1-C6 haloalkyl, E-1-E-54, F-1-F-15 or di(C1-C6 alkyl)amino, R g represents a hydrogen atom or a tri(C1-C4 alkyl)silyl group, R h represents a C1-C6 alkyl group, R i represents a hydroxyl group or a C1-C6 alkoxy group, E-1 to E-54 represent the structures shown in the following structural formulas, F-1 to F-15 represent the structures shown in the following structural formulas, Z a represents a halogen atom, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylcarbonyl group or a C1-C6 alkoxycarbonyl group, About Z a The relationship between them allows each Z to a Same or different from each other, About Z a The relationship between them allows each Z to a Same or different from each other, About Z a The relationship between them is that when v5 represents an integer of 2, 3, 4, or 5, each Z is allowed to a Same or different from each other, About Z a The relationship between them allows each Z to a Same or different from each other, About Z a The relationship between them, when v3 represents an integer 2 or 3, allows each Z a Same or different from each other, About Z a The relationship between them, when v2 represents the integer 2, allows each Z a Same or different from each other, Z b represents a C1-C6 alkyl group, m5, n5 and u5 each represent an integer of 0, 1, 2, 3, 4 or 5, n3 represents an integer 0, 1, 2 or 3, u4 represents an integer 0, 1, 2, 3, or 4, n7 represents an integer 0, 1, 2, 3, 4, 5, 6 or 7, p represents an integer 0 or 1, r 1 represents an integer 1 or 2, r 2 Represents an integer 0 or 1, t represents an integer 0, 1 or 2, v1 represents an integer 0 or 1, v2 represents an integer 0, 1, or 2, v3 represents an integer 0, 1, 2, or 3, v4 represents an integer 0, 1, 2, 3, or 4, v5 represents an integer 0, 1, 2, 3, 4, or 5, v6 represents an integer 0, 1, 2, 3, 4, 5, or 6, v7 represents an integer 0, 1, 2, 3, 4, 5, 6, or 7.

2. The pyrazole compound or a salt thereof according to claim 1, wherein R b represents cyano or phenyl, X 1 represents a halogen atom, R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R', R Y represents a hydrogen atom, R a represents a hydrogen atom, a C1-C6 alkyl group, R a -1 or R a -4, R 5 represents a hydrogen atom, R 6 represents a hydrogen atom, R 7 represents a C1-C6 alkyl group, Z represents Z-1, Z-2, Z-3, Z-4 or Z-6, Z 1 represents hydroxyl, carboxyl, amino, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, i Substituted C1-C6 alkyl, -OR d 、-NHC(O)R e 、-NR h C(O)R e 、-NHSO2R f 、-C≡CR g , -SO2NH2, -C(=NOR)R', E-1, E-2, E-3, E-7, E-12, E-14, E-21, E-23, E-24, E-31, F-10 or F-11, R d represents C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, 10 Substituted C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylaminocarbonyl or E-1, R 10 Represents C3~C 10 Cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, di(C1-C6)alkylaminocarbonyl, -C(=NOR)R', E-1, E-2, E-3, E-5, E-22, E-30, E-41 or F-3, R e represents C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C2-C6 alkenyloxy, C1-C6 alkylamino, di(C1-C6)alkylamino, benzyloxy, E-1, E-2, E-3, E-4, E-8, E-11, E-13, E-14 or E-23; R f represents C1-C6 alkyl, C1-C6 haloalkyl, di(C1-C6 alkyl)amino or E-1, m5 represents an integer 0, 1 or 2, n5 represents an integer 0, 1, 2 or 3, n3 represents an integer 0 or 1, u5 represents an integer 0 or 1, u4 represents the integer 0, n7 represents the integer 0, r 1 represents the integer 1, v1 represents the integer 1, v2 represents an integer 0 or 1, v3 represents an integer 0, 1, or 2, v4 represents an integer 0, 1, 2, or 3, v5 represents an integer 0, 1, or 2, v6 represents the integer 0.

3. The pyrazole compound or a salt thereof according to claim 2, wherein R 2 represents a hydrogen atom, and p represents the integer 1.

4. The pyrazole compound or a salt thereof according to claim 3, wherein T represents an oxygen atom.

5. The pyrazole compound or a salt thereof according to claim 4, wherein R a represents a hydrogen atom or a C1-C6 alkyl group.

6. The pyrazole compound or a salt thereof according to claim 2, wherein p represents the integer 0.

7. The pyrazole compound or a salt thereof according to claim 6, wherein G 1 represents a halogen atom, a C1-C6 haloalkyl, a C1-C6 alkoxy or a C1-C6 haloalkoxy, T represents oxygen atom, R X Represents C1-C6 alkyl, benzyl, R X -1 or R X -2, R 1 represents a hydrogen atom, R a represents a hydrogen atom, a C1-C6 alkyl group or R a -1, Z stands for Z-1, Z-2 or Z-3, Z 1 represents a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group, n5 represents an integer 0, 1 or 2, u5 represents the integer 0.

8. A production intermediate, which is represented by formula (1-1a) and is a production intermediate of the pyrazole compound according to any one of claims 1 to 6, In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula, G 1 Represents hydroxyl, nitro, cyano, halogen, C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, b Substituted C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl, di(C1-C6alkyl)aminocarbonyl, or -C(=NOR)R', About G 1 The relationship between them, when m5 represents an integer of 2, 3, 4 or 5, allows each G 1 Same or different from each other, R b Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl, phenyl or -C(=NOR)R', R represents a hydrogen atom or a C1-C6 alkyl group, R' represents a C1-C6 alkyl group, R X Represents C1~C6 alkyl, C3~C 10 Cycloalkyl, C1-C6 haloalkyl, R c Substituted C1-C6 alkyl, benzyl, R X -1. R X -2. R X -3 or R X -4, R X -1~R X -4 represent the structures shown in the following structural formulas, X 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a C1-C6 alkoxy group, About X 1 The relationship between them allows each X to 1 Same or different from each other, About X 1 The relationship between them allows each X to 1 Same or different from each other, R c Represents cyano, C3~C 10 Cycloalkyl, C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, di(C1-C6 alkyl)aminocarbonyl or -C(=NOR)R', R Y represents a hydrogen atom, a halogen atom or a C1-C6 alkyl group, m5 and u5 represent integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4.

9. The manufacturing intermediate according to claim 7, wherein: G 1 represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group or a C1-C6 alkylthio group, R X Represents C1-C6 alkyl, benzyl, R X -1. R X -2 or R X -3, X 1 represents a halogen atom, R Y represents a hydrogen atom, m5 represents an integer 0, 1 or 2, u5 represents an integer 0 or 1, u4 represents the integer 0. 10 . A pesticide comprising, as an active ingredient, at least one compound selected from the group consisting of the pyrazole compounds and salts thereof according to claim 1 . 11 . A fungicide comprising, as an active ingredient, at least one selected from the pyrazole compound and a salt thereof according to claim 1 . 12 . An agricultural and horticultural fungicide comprising, as an active ingredient, at least one selected from the group consisting of the pyrazole compounds and salts thereof according to claim 1 . 13 . An antifungal agent comprising, as an active ingredient, at least one selected from the group consisting of the pyrazole compounds and salts thereof according to claim 1 .

14. An endoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the pyrazole compound and a salt thereof according to any one of claims 1 to 7.

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