Pyrazole compounds and pest control agents

Abstract

To provide a novel fungicide, particularly a fungicide for agricultural and horticultural use.SOLUTION: Provided is a pyrazole compound represented by formula (1), or a salt thereof. [In the formula, G represents G-1; G1 represents C1-C6 haloalkyl and the like; T represents an oxygen atom and the like; RX represents C1-C6 alkyl and the like; RY represents a hydrogen atom and the like; R1 represents a hydrogen atom and the like; R2 represents a hydrogen atom and the like; R3 represents a hydrogen atom and the like; R4 represents -ORa and the like; Ra represents a hydrogen atom and the like; R5 represents a hydrogen atom and the like; Z represents Z-1 and the like; Z1 represents C1-C6 alkyl and the like; and m5 and n5 each represent an integer of 0, 1, 2, 3, 4 or 5].SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to novel pyrazole compounds and salts thereof, and pest control agents containing said compounds and salts thereof as active ingredients. [Background technology]

[0002] Patent Documents 1 and 2 disclose certain pyrazole compounds.

[0003] Moreover, Patent Documents 3 and 4 disclose that certain pyrazole compounds are useful as fungicides.

[0004] Furthermore, Patent Documents 5 to 8 disclose that certain heterocyclic compounds are useful as fungicides. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2002 / 085860 [Patent Document 2] International Publication No. 2006 / 132197 [Patent Document 3] International Publication No. 2009 / 028280 [Patent Document 4] International Publication No. 1996 / 038419 [Patent Document 5] International Publication No. 2020 / 109391 [Patent Document 6] International Publication No. 2021 / 224220 [Patent Document 7] International Publication No. 2021 / 228734 [Patent Document 8] International Publication No. 2021 / 233861 Summary of the Invention [Problem to be solved by the invention]

[0006] However, long-term use of drugs can lead to the acquisition of drug resistance in pathogens, and therefore there is a constant demand for the development of new drugs with excellent pest control effects. [Means for solving the problem]

[0007] Means for Solving the Problems The present inventors have conducted intensive research aimed at solving the above problems, and as a result have found that a novel pyrazole compound represented by the following formula (1) according to the present invention exhibits excellent control activity as a fungicide, particularly as an agricultural and horticultural fungicide, and have completed the present invention.

[0008] That is, the present invention relates to a pyrazole compound represented by the following formula (1) and a salt thereof.

[0009] Formula (1):

[0010] [ka]

[0011] [In the formula, G represents G-1, G-1 represents a structure represented by the following structural formula:

[0012] [ka]

[0013] G 1 is a hydroxyl, nitro, cyano, halogen atom, C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, R b C replaced with 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, di(C 1 ~C 6 Alkyl)amino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, C 3 ~C 10 Cycloalkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', G 1 In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G 1 may be the same as or different from each other, R b Cyano, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', R is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R' is C 1 ~C 6 represents an alkyl group, T represents an oxygen atom or a sulfur atom; R X is C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, R c C replaced with1 ~C 6 Alkyl, benzyl, R X -1, R X -2, R X -3 or R X represents -4, R X -1~R X -4 represents a structure represented by the following structural formula,

[0014] [ka]

[0015] X 1 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl or C 1 ~C 6 represents alkoxy, X 1 In the relationship, when u5 is an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other, X 1 In the relationship between X and u4, when u4 is an integer of 2, 3 or 4, 1 may be the same as or different from each other, R c Cyano, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', R Y is a hydrogen atom, a halogen atom or C 1 ~C 6 represents an alkyl group, R 1is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 2 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 4 -OR a represents R 5 is a hydrogen atom, C 1 ~C 6 Alkyl or C 1 ~C 6 represents haloalkyl, Or, R 4 and R 5 Together, C 2 ~C 5 By forming an alkylene chain, R 4 and R 5 represents that the ring is formed of 3 to 6 members together with the carbon atom to which it is bonded. R a is a hydrogen atom, C 1 ~C 6 Alkylcarbonyl or C 1 ~C 6 represents haloalkylcarbonyl; Z represents Z-1 to Z-7 or Z-8; Z-1 to Z-8 each represent a structure represented by the following structural formula:

[0016] [ka]

[0017] In addition, Z 1 The substitution position of represents a substitution on the aromatic ring of Z-1 to Z-8, Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C 1 ~C 6 Alkyl, C 3 ~C 10Cycloalkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 10 Halocycloalkyl, C 2 ~C 6 Alkenyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, C 1 ~C 6 Alkylamino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, R i C replaced with 1 ~C 6 Alkyl, -OR d , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R f , -C≡CR g , -SO 2 NH 2 , -C(=NOR)R', E-1 to E-54, F-1 to F-14 or F-15; Z 1 In the case where n7 is an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other, Z 1 In the case where n5 is an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other, Z 1 In the case where n4 is an integer of 2, 3 or 4, each Z 1 may be the same as or different from each other, Z 1 In the case where n3 is an integer of 2 or 3, each Z1 may be the same as or different from each other, R d is C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Haloalkyl, R 10 C replaced with 1 ~C 6 Alkyl, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 alkylaminocarbonyl, E-1 to E-54, F-1 to F-14 or F-15; R 10 is C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, di(C 1 ~C 6 -C(=NOR)R', E-1 to E-54, F-1 to F-14 or F-15; R e is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, C 2 ~C 6 Alkenyloxy, C 1 ~C 6 Alkylamino, di(C 1 ~C 6 alkyl)amino, benzyloxy, E-1 to E-54, F-1 to F-14 or F-15; R f is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, di(C 1 ~C 6alkyl)amino, E-1 to E-54, F-1 to F-14 or F-15; R g is a hydrogen atom or tri(C 1 ~C 4 alkyl)silyl; R h is C 1 ~C 6 represents an alkyl group, R i is hydroxy or C 1 ~C 6 represents alkoxy, E-1 to E-54 each represent a structure represented by the following structural formula:

[0018] [ka]

[0019] [ka]

[0020] F-1 to F-15 each represent a structure represented by the following structural formula:

[0021] [ka]

[0022] Z a is a halogen atom, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkylcarbonyl or C 1 ~C 6 represents an alkoxycarbonyl; Z aIn the case where v7 is an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other, Z a In the case where v6 is an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other, Z a In the relationship between v5 and Z, when v5 is an integer of 2, 3, 4 or 5, a may be the same as or different from each other, Z a In the case where v4 is an integer of 2, 3 or 4, each Z a may be the same as or different from each other, Z a In the case where v3 is an integer of 2 or 3, each Z a may be the same as or different from each other, Z a In the relationship between v2 and each Z a may be the same as or different from each other, Z b is C 1 ~C 6 represents an alkyl group, m5 represents an integer of 0, 1, 2, 3, 4 or 5; n7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; n5 represents an integer of 0, 1, 2, 3, 4 or 5; n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2 or 3; u5 represents an integer of 0, 1, 2, 3, 4 or 5; u4 represents an integer of 0, 1, 2, 3, or 4; v7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; v6 represents an integer of 0, 1, 2, 3, 4, 5, or 6; v5 represents an integer of 0, 1, 2, 3, 4, or 5; v4 represents an integer of 0, 1, 2, 3, or 4; v3 represents an integer of 0, 1, 2, or 3; v2 represents an integer of 0, 1, or 2; v1 represents an integer of 0 or 1. Effect of the Invention

[0023] The compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogens.

[0024] Thus, the present invention can provide novel pyrazole compounds or salts thereof which are useful as fungicides, particularly as agricultural and horticultural fungicides. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] The present invention will be described in detail below.

[0026] The compound of the present invention may have geometric isomers of E- and Z-isomers depending on the type of substituents, and the present invention includes a mixture containing these E-, Z-, or E- and Z-isomers in any ratio.

[0027] Furthermore, the compound of the present invention may exist in optically active forms due to the presence of one or more asymmetric carbon atoms or sulfur atoms, and the present invention includes all optically active forms and racemic forms.

[0028] Furthermore, the compounds of the present invention may have tautomers depending on the type of substituent, and the present invention encompasses all tautomers or a mixture of tautomers containing any ratio.

[0029] In addition, the compound of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, and the present invention encompasses all rotational isomers or a mixture of diastereomers containing them in any ratio.

[0030] Next, specific examples of the substituents shown in the present specification are shown below, where n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.

[0031] In the present specification, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" in the present specification also represents these halogen atoms.

[0032] In this specification, "C a ~C b The term "alkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl, each of which is selected within the range of the number of carbon atoms specified.

[0033] In this specification, "C a ~C b The term "haloalkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms, in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. Specific examples include 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, and are selected within the range of the number of carbon atoms specified for each group.

[0034] In this specification, "C a ~C bThe term "alkenyl" refers to a linear or branched unsaturated hydrocarbon having a to b carbon atoms and having one or more double bonds in the molecule. Specific examples include vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 1,1-dimethyl-2-propenyl, and the like, and each is selected within the range of the specified number of carbon atoms.

[0035] In this specification, "C a ~C b The term "alkynyl" refers to a linear or branched unsaturated hydrocarbon having a to b carbon atoms and having one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl, each of which is selected within the range of the number of carbon atoms specified.

[0036] In this specification, "C a ~C b The term "alkoxy" refers to alkyl-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, and the like, and each is selected within the range of the specified number of carbon atoms.

[0037] In this specification, "C a ~C b The term "haloalkoxy" refers to haloalkyl-O- having a to b carbon atoms, and specific examples thereof include 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-hexafluoropropyloxy, each of which is selected within the range of the number of carbon atoms specified.

[0038] In this specification, "C a ~C b The expression "alkenyloxy" represents alkenyl-O- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, and 1,1-dimethyl-2-propenyloxy, and are selected within the range of the number of carbon atoms specified for each group.

[0039] In this specification, "C a ~C b The notation of "alkylthio" represents alkyl-S- having the above-mentioned meaning containing a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, tert-butylthio, etc., and each of them is selected within the range of the specified number of carbon atoms.

[0040] In this specification, "C a ~C b The notation of "alkylsulfinyl" represents alkyl-S(O)- as defined above having a to b carbon atoms, and specific examples thereof include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl, and the like, each selected within the range of the specified number of carbon atoms.

[0041] In this specification, "C a ~C b The expression "alkylsulfonyl" means an alkyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. 2 Specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, and the like, each of which is selected within the range of the number of carbon atoms specified.

[0042] In this specification, "C a ~C b The term "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, which can form a single ring or a composite ring structure having 3 to 10 members. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each of which is selected within the range of the specified number of carbon atoms.

[0043] In this specification, "C a ~C b The term "halocycloalkyl" refers to a cyclic hydrocarbon having a to b carbon atoms, in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and which can form a single ring or a complex ring structure having 3 to 10 members. Each ring may be optionally substituted with an alkyl within the range of the specified number of carbon atoms, and the halogen atoms may be substituted at the ring structure portion, the side chain portion, or both. Furthermore, when substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. 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, 2,2,3,3-tetrafluorocyclobutyl, etc. are specific examples, and each may be selected within the range of the specified number of carbon atoms.

[0044] In this specification, "C a ~C bThe term "alkylamino" refers to amino in which one of the hydrogen atoms is substituted with the above-mentioned alkyl having a to b carbon atoms, and specific examples thereof include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino, each of which is selected within the range of the number of carbon atoms specified.

[0045] In this specification, "di(C a ~C b The expression "alkyl)amino" represents amino in which both hydrogen atoms are substituted with alkyl as defined above, each of which may be the same or different and has a to b carbon atoms, and specific examples thereof include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., each of which is selected within the range of the specified number of carbon atoms.

[0046] In this specification, "C a ~C b The expression "alkylcarbonyl" represents alkyl-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl, each of which is selected within the range of the specified number of carbon atoms.

[0047] In this specification, "C a ~C b The term "haloalkylcarbonyl" refers to haloalkyl-C(O)- having a to b carbon atoms as defined above, and specific examples thereof include difluoroacetyl, trichloroacetyl, and trifluoroacetyl, each of which is selected within the range of the number of carbon atoms specified.

[0048] In this specification, "C a ~C bThe term "alkoxycarbonyl" represents alkyl-OC(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, and the like, each of which is selected within the range of the specified number of carbon atoms.

[0049] In this specification, "C a ~C b The expression "alkylaminocarbonyl" represents carbamoyl in which one of the hydrogen atoms is substituted with the above-mentioned alkyl having a to b carbon atoms, and specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, tert-butylcarbamoyl, and the like, each of which is selected within the range of the specified number of carbon atoms.

[0050] In this specification, "C a ~C b The term "cycloalkylaminocarbonyl" refers to carbamoyl in which one of the hydrogen atoms is substituted with the above-mentioned cycloalkyl having a to b carbon atoms, and specific examples thereof include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl, each of which is selected within the range of the number of carbon atoms specified.

[0051] In this specification, "di(C a ~C bThe expression "alkylaminocarbonyl" represents carbamoyl in which both hydrogen atoms are substituted with alkyl having a to b carbon atoms, each of which may be the same or different, as defined above. Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl, each of which is selected within the range of the number of carbon atoms specified.

[0052] As used herein, "tri(C a ~C b The expression "alkylsilyl" represents silyl substituted by alkyl having the above-mentioned meaning, each of which may be the same or different and has a to b carbon atoms. Specific examples include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, tert-butyldimethylsilyl, etc., each of which is selected within the range of the number of carbon atoms specified.

[0053] In this specification, "R c C replaced with a ~C b Alkyl, R i C replaced with a ~C b Alkyl" or "R 10 C replaced with a ~C b The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R c , R i or R 10 represents an alkyl having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, each of which is selected within the range of the number of carbon atoms specified. c , R i or R 10 When two or more are present, the substituent R c , R i or R 10 may be the same or different from each other.

[0054] In this specification, "R b C replaced with a ~C b The notation "alkoxy" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R b represents an alkoxy having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, and is selected within the range of the number of carbon atoms specified for each. b When two or more are present, the substituent R b may be the same or different from each other.

[0055] In this specification, the notation "benzyl" is -CH 2 C 6 H 5 Represents.

[0056] In this specification, the term "benzyloxy" is defined as -O-CH 2 C 6 H 5 Represents.

[0057] Next, a method for producing the compound of the present invention represented by formula (1) will be described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. Note that the following explanation is merely illustrative, and the compound of the present invention represented by formula (1) may be produced by other methods. Hereinafter, the "compound of the present invention represented by formula (1)" will also be described as "compound of the present invention (1)", and the "compound of formula (2)" will also be described as "compound (2)". Other compounds will also be described in a similar manner.

[0058] (Production Example 1) The compound (1) of the present invention can be produced, for example, by the following production method.

[0059] [ka]

[0060] [In the formula, J1 is a chlorine atom, a bromine atom, C 1 ~C 4 Alkylcarbonyloxy (e.g., acetoxy, etc.) or C 1 ~C 4 G, T, and R represent a leaving group of alkoxycarbonyloxy (e.g., methoxycarbonyloxy, etc.). X , R Y , R 1 , R 2 , R 3 , R 4 , R 5 , and Z and have the same meanings as above.] The compound (1) of the present invention can be produced by reacting the compound (1-1), the compound (1-1-1) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) with a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of either one or both of a base and an additive.

[0061] Alternatively, compound (1) of the present invention can also be produced by reacting compound (1-2) with compound (1-1-1) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of either or both of a base and an additive.

[0062] The amount of compound (1-1-1) or a salt thereof used is 0.5 to 50 equivalents per equivalent of compound (1-1) or compound (1-2).

[0063] Some of the compounds (1-1-1) are known compounds, some of which are commercially available, and the rest can be prepared according to general synthetic methods for known compounds described in the literature.

[0064] The amount of the dehydration condensation agent used is 0.5 to 50 equivalents relative to 1 equivalent of the compound (1-1).

[0065] Examples of the dehydration condensation agent include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and the like.

[0066] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include water, alcohol solvents such as methanol, ethanol, and tert-butyl alcohol, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglyme, aromatic hydrocarbon solvents such as benzene, xylene, and toluene, aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane, nitrile solvents such as acetonitrile and propionitrile, amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone, dimethyl sulfoxide, pyridine, and mixed solvents thereof.

[0067] Examples of bases that can be used in the reaction include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, N,N-diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of compound (1-1) or compound (1-2).

[0068] Examples of additives that can be used in the reaction include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, 4-(dimethylamino)pyridine, etc. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents relative to 1 equivalent of compound (1-1) or compound (1-2).

[0069] The reaction temperature can be set at any temperature between -78°C and 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 usually be set at any time within the range of 5 minutes to 100 hours.

[0070] (Production Example 2) The compound (3) of the present invention can be produced, for example, by the following production method.

[0071] [ka]

[0072] [In the formula, L 1 is a chlorine atom, a bromine atom, an iodine atom, C 1 ~C 6Alkylcarbonyloxy (e.g., acetoxy, etc.), C 1 ~C 6 represents a leaving group such as haloalkylcarbonyloxy (e.g., trifluoroacetoxy, etc.); R a1 is C 1 ~C 6 Alkylcarbonyl or C 1 ~C 6 It stands for haloalkylcarbonyl, and G, T, R X , R Y , R 1 , R 2 , R 3 , R 5 and Z have the same meaning as above.] The compound (3) of the present invention can be produced by reacting the compound (2) of the present invention with a compound (D) in a solvent or without a solvent, and optionally in the presence of a base.

[0073] The amount of compound (D) used is 0.5 to 50 equivalents per equivalent of compound (2).

[0074] Some of the compounds (D) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds described in the literature.

[0075] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0076] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents relative to 1 equivalent of the compound (2) of the present invention.

[0077] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0078] The compound (2) of the present invention can be synthesized according to the method of Production Method 1.

[0079] (Production Example 3) The compound (4) of the present invention can be produced, for example, by the following production method.

[0080] [ka]

[0081] [In the formula, L is a chlorine atom, a bromine atom, an iodine atom, C 1 ~C 4 Alkyl sulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C 1 ~C 4 R represents a leaving group such as haloalkylsulfonyloxy (e.g., trifluoromethanesulfonyloxy) or arylsulfonyloxy (e.g., p-toluenesulfonyloxy), Xa is C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, R c C replaced with 1 ~C 6 Represents alkyl or benzyl, and G, T, R Y , R 1 , R 2 , R 3 , R 4 , R 5 , R c and Z have the same meaning as above.] The compound (4) of the present invention can be produced by reacting the compound (1-3) with the compound (D1) in a solvent or without a solvent, and optionally in the presence of a base.

[0082] The amount of compound (D1) used is 0.5 to 50 equivalents per equivalent of compound (1-3).

[0083] Some of the compounds (D1) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds described in the literature.

[0084] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0085] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents relative to 1 equivalent of the compound of the present invention (1-3).

[0086] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0087] The compound (1-1) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 1.

[0088] [Reaction Scheme 1]

[0089] [ka]

[0090] [In the formula, X represents a halogen atom; G, T, and R X and R Y has the same meaning as above.] Compound (1-1) can be obtained by reacting compound (1-4) with compound (A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, compound (1-1) can be obtained by reacting compound (1-4) with compound (A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand.

[0091] Some of the compounds (1-4) are known compounds, some of which are commercially available, and the rest can be prepared according to general methods for synthesizing known compounds described in the literature.

[0092] The amount of compound (A) used is 0.5 to 50 equivalents per equivalent of compound (1-4).

[0093] Some of the compounds (A) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds described in the literature.

[0094] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0095] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of compound (1-4).

[0096] 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 that can be used is 0.001 to 50 equivalents relative to 1 equivalent of the compound (1-4).

[0097] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc. The amount (equivalent) of the additive used is 0.001 to 100 equivalents relative to 1 equivalent of the compound (1-4).

[0098] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst that can be used include palladium (divalent) (π-cinnamyl) chloride (dimer), allylpalladium (divalent) chloride (dimer), etc. The amount (equivalent) of the palladium catalyst used is 0.001 to 50 equivalents relative to 1 equivalent of the compound (1-4).

[0099] 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 (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), etc. The amount (equivalent) of the ligand used is 0.001 to 50 equivalents relative to 1 equivalent of the compound (1-4).

[0100] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0101] The compound (1-2) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Scheme 2.

[0102] [Reaction Scheme 2]

[0103] [ka]

[0104] [J 1 , G.T.R. X , and R Y has the same meaning as above.] Compound (1-2) can be obtained by reacting compound (1-1) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride in accordance with a known method described in the literature, for example, the method described in Journal of Medicinal Chemistry [J. Med. Chem.], 1991, Vol. 34, p. 1630, or the like. Alternatively, compound (1-2) can be obtained by reacting compound (1-1) with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, if necessary, in the presence of a base, in accordance with the method described in Tetrahedron Lett., 2003, vol. 44, p. 4819, Journal of Medicinal Chemistry, 1991, vol. 34, p. 222, or the like.

[0105] In the compound (1-1), T is an oxygen atom and R Y The compound (1-5) in which is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 3.

[0106] [Reaction Scheme 3]

[0107] [ka]

[0108] [In the formula, R 101 is C 1 ~C 6 represents alkyl; G and R X has the same meaning as above.] Step 1: Compound (1-7) can be obtained by reacting compound (1-6) with compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.

[0109] Some of the compounds (B) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds described in the literature.

[0110] The amount of compound (B) or a salt thereof used is 0.5 to 50 equivalents relative to 1 equivalent of compound (1-6).

[0111] Some of the compounds (1-6) are known compounds described in Bioorganic & Medicinal Chemistry Letters, 2015, vol. 25, p. 4481, and the other compounds can be synthesized in the same manner as known compounds according to the methods described in the literature.

[0112] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0113] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of compound (1-6).

[0114] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0115] Step 2: Compound (1-5) can be obtained by reacting compound (1-7) with an oxidizing agent in a solvent or without a solvent.

[0116] The oxidizing agent that can be used includes, for example, potassium permanganate, etc. The amount (equivalent) of the oxidizing agent used is 0.1 to 100 equivalents per equivalent of the compound (1-7).

[0117] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0118] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0119] Compound (1-5) can also be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 4.

[0120] [Reaction Scheme 4]

[0121] [ka]

[0122] [Wherein, G and R X has the same meaning as above.] Step 1: Compound (1-9) can be obtained by reacting compound (1-8) under the same conditions as in step 1 of reaction scheme 3.

[0123] Some of the compounds (1-8) are known compounds described in WO 2003 / 016275, and the others can be synthesized in the same manner as known compounds according to the methods described in the document.

[0124] Step 2: Compound (1-5) can be obtained by reacting compound (1-9) with carbon dioxide in the presence of a base, either in a solvent or without a solvent.

[0125] The base that can be used includes, for example, n-butyllithium, etc. The amount (equivalent) of the base used is 0.1 to 100 equivalents relative to 1 equivalent of the compound (1-9).

[0126] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0127] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0128] The compound (1-3) used in Production Example 3 can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Scheme 5.

[0129] [Reaction Scheme 5]

[0130] [ka]

[0131] [In the formula, G, T, R Y , R 1 , R 2 , R 3 , R 4 , R 5 and Z have the same meaning as above.] The compound (1-3) can be produced by reacting the compound (5) of the present invention with an acid in a solvent or without a solvent.

[0132] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples of the solvents include those exemplified in Production Example 1.

[0133] Examples of the acid that can be used in the reaction include hydrochloric acid, sulfuric acid, formic acid, trifluoroacetic acid, etc. The amount (equivalent) of the acid to be used is 0.1 to 100 equivalents relative to 1 equivalent of the compound (5) of the present invention.

[0134] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0135] The compound (5) of the present invention can be synthesized according to the method of Production Method 1.

[0136] The compound of the present invention can generally be used as an agricultural and horticultural bactericide or fungicide against various diseases caused by Phytophthora, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Fungi Imperfecti, bacteria or viruses.

[0137] The compound of the present invention can generally be used as an agricultural and horticultural bactericide or fungicide against various diseases caused by Phytophthora, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Fungi Imperfecti, bacteria or viruses.

[0138] The term "pathogenic microorganism" refers to a microorganism that causes a plant disease, and specific examples thereof include, but are not limited to, the following microorganisms: 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., Cercospora spp. (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.), Phaeoisariopsis 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. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (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., Leptosphaeria coniothyrium, 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., Pyrenophora graminea, 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., Phyllosticta zingiberis, etc.), Schizothyrium spp. (e.g., Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillus spp., Penicillium spp. (e.g., Penicillium digitatum, 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, B. g. f. sp. tritici, etc.), Erysiphe spp. (e.g., Erysiphe betae, E. cichoracearum, E. c. 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, U. n. var. necator, etc.), Uncinuliella spp. (e.g., Uncinuliella simulans var. simulans, U. s. var. 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., Tapesia acuformis, T.yallundae, Lachnum spp., Scleromitrula spp., Botryotinia spp., Botryotinia fuckeliana spp., Botrytis spp. cinerea, B. fabae, B. squamosa, Ciborinia spp., Monilinia spp. laxa , M. vaccinii-corymbosi , Sclerotinia spp heterodoxa spp., Claviceps spp. (Claviceps sorghi, C. sorghicola species), Epichloe spp., Ephelis japonica, Villosiclava virens, Hypomyces spp., Hypomyces solani f. sp. mori, Trichoderma spp., Calonectria spp., Candelospora spp spp., Cylindrocladium spp., Fusarium spp., Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. of sp. asparagus、F. of sp.colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp. lagenariae, F. of sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. of sp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sf sp. cucurbitae, F. sf sp. eumartii, F. sf sp. glycines, F. sf sp. pisi, F. sf sp. Radicicola, F. virguliforme etc.), Gibberella spp. (eg Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (eg Verticillium albo-atrum, V. dahliae, V. longisporum etc.), Ceratocystis spp. (for example, Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp. (for example, Thielaviopsis basicola etc.), Adisciso spp., Monochaetia spp., Pestalotia spp.(Excludes Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae) Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp necatrix spp., Monographella spp., Ophiostoma spp., Cryphonectria spp., Cryphonectria parasitica spp., Diaporthe spp citri, D. nomurai, D. tanakae, Diaporthopsis spp spp., Discula spp., Discula theae-sinensis spp., Gnomonia spp., Coniella spp., Coryneum spp., Greeneria spp., Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp spp. (Excludes Valsa ceratosperma spp.) Tubakia spp. Monosporascus spp. Clasterosporium spp. (Excludes Gaeumannomyces graminis spp.) Magnaporthe spp. (including Magnaporthe grisea), Pyricularia spp., (including Pyricularia zingiberis), Monilochaetes infuscans, Colletotrichum spp. C. cereale, C. fragariae, C. orbiculare.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. Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora spp. (e.g. Phialophora gregata, etc.), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g. Rhynchosporium secalis, Sarocladium spp., Coleophoma spp., Helicoceras oryzae and other Ascomycota fungi. 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, P. c. var. coronata, P. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tanaceti, P. tokyensis, P. zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (eg Blastospora smilacis etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (eg Sporisorium scitamineum etc.), Ustilago spp. (eg Ustilago maydis, U. nuda etc.), Entyloma spp., Exobasidium spp. spp. (for example, Tilletia caries, T. controversa, T. laevis, etc.), Itersonilia spp. (for example, 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., Lepista spp. (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., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani, etc.), Thanatephorus spp. (e.g., Thanatephorus cucumeris, etc.), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, Phanerochaete spp. and other Basidiomycota fungi. Fungi of the phylum Chitridiomycota such as Olpidium spp. Fungi of the phylum Blastocladiomycota such as Physoderma spp. Fungi of the subphylum Mucoromycotina such as 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.) Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g. Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. 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 alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosa f. sparsa, Plasmopara spp., Plasmopara halstedii, P. nivea, P. viticola, Pseudoperonospora spp spp., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, and P. spp. palmivora, P. syringae, P. sp. ARRHENOMANES、P. Taxummaniae、p. Debaryanum 、p. Gramininicola 、p. Horinouchiense、p. Irregularelanp. Freedom 、p. Myriotylute 、p. okanoganenne、p. Paddicum 、p. Paroecandrr. Periplocum 、p. spinosum, P. ultimum, P. vexans. volutum (Heterokontophyta) strains (Oomycetes) of Clavibacter spp., Clavibacter michiganensis subsp.michiganensis, Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli, etc.), Streptomyces spp. (e.g., Streptomyces ipomoeae, etc.). Gram-positive bacteria of the Firmicutes phylum, such as Clostridium sp.. Gram-positive bacteria of the Tenericutes phylum, 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, A. a. subsp. citrulli, A. konjaci etc.), Herbaspirillum spp., Ralstonia spp. (e.g. Ralstonia solanacearum etc.), Xanthomonas spp. (e.g. cucurbitae, X. c. pv. glycines, X. c. pv. mangiferaeindicae, X. c. pv. nigromaculans, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzae pv. marginalis, P. savastanoi pv. glycinea, P. syringae, P. s. pv. actinidiae, P. s. pv.eriobotryae, P. s. pv. helianthi, P. s. pv. lachrymans, P. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s. pv. viridiflava, etc.), Rhizobacter spp., Brenneria spp. (e.g., Brenneria nigrifluens, etc.), Dickeya spp. (e.g., Dickeya dianthicola, D. zeae, etc.), Erwinia spp. (e.g., Erwinia amylovora, E. rhapontici, etc.), Pantoea spp., Pectobacterium spp. (e.g. Pectobacterium Gram-negative bacteria of the Proteobacteria phylum, such as P. atrosepticum, P. carotovorum, P. wasabiae, etc.

[0139] Specific examples of plant diseases caused by infection and proliferation of these pathogens include, but are not limited to, the following plant diseases. Leaf curl (Taphrina deformans) on peach, Plum pockets (Taphrina pruni) on plum, Leaf spot (Cercospora asparagi) on asparagus, Cercospora leaf spot (Cercospora beticola) on sugar beet, Frogeye leaf spot (Cercospora capsici) on bell pepper, Angular leaf spot (Cercospora kaki) on persimmon, Purple stain (Cercospora kikuchii) on soybean, Brown leaf spot (Mycosphaerella arachidis) on peanut, Cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii) on cherry, Black sigatoka disease (Mycosphaerella fijiensis) on cherry, Yellow sigatoka disease sigatoka (Mycosphaerell musicola), Speckled leaf blotch (Mycosphaerella graminicola), Circular leaf spot (Mycosphaerella nawae), Pea blight (Mycosphaerella pinodes), Zingiberis leaf spot (Mycosphaerella zingiberis), Tomato leaf mold (Mycovellosiella fulva), Eggplant leaf mold (Mycovellosiella nattrassii), Tomato leaf mold (Cercospora fuligena), Grapevine leaf spot (Pseudocercospora vitis), Chinese cabbage leaf spot (Pseudocercosporella capsellae), Chrysanthemum leaf spot (Septoriachrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape anthracnose (Elsinoe ampelina), Araliae spot anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta pisi), Cucumber leaf spot (Corynespora cassiicola), Stem canker (Leptosphaeria coniothyrium), Wheat glume blotch (Leptosphaeria nodorum), Rose leaf spot (Alternaria alternata), Cabbage leaf spot (Alternaria brassicae), Carrot leaf blight (Alternaria dauci), Pear black spot (Alternaria kikuchiana), Alternaria blotch (Alternaria mali) on apple, Alternaria leaf spot (Alternaria porri) on leek, Target spot (Bipolaris sorghicola) on sorghum, Southern leaf blight (Cochliobolus heterostrophus) on corn, Brown spot (Cochliobolus miyabeanus) on rice, Tip blight (Pleospora herbarum) on garlic, Stripe (Pyrenophora graminea) on barley, Net blotch (Pyrenophora teres) on barley, Leaf blight (Setosphaeria turcica) on sorghum, Northern leaf blight (Setosphaeria turcica) on corn, Leaf spot (Stemphylium asparagus)botryosum), Scab (Venturia carpophila) of Rosaceae (Prunus subfamily), Scab (Venturia inaequalis) of apple, Scab (Venturia nashicola) of pear, Gummy stem blight (Didymella bryoniae) of Cucurbitaceae, Leaf spot (Phoma exigua var. exigua) of burdock, Streak (Phoma wasabiae) of wasabi, Ring rot (Botryosphaeria berengeriana f. sp. piricola) of Rosaceae (Prunus subfamily), Soft rot of kiwifruit (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Common green mold (Penicillium digitatum) of citrus, Blue mold (Penicillium italicum), powdery mildew occurring on various crops, powdery mildew on barley (Blumeria graminis f. sp. hordei), powdery mildew on wheat (Blumeria graminis f. sp. tritici), powdery mildew on cucumber (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), powdery mildew on eggplant (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), powdery mildew on carrots and parsley (Erysiphe heraclei), powdery mildew on peas (Erysiphe pisi), powdery mildew on tomatoes (Leveillula taurica, Oidium neolycopersici, Oidium sp.), powdery mildew on peppers (Leveillula taurica), Pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), Bitter melon powdery mildew (Oidium sp.), Persimmon powdery mildew (Phyllactiniakakicola), Burdock powdery mildew (Podosphaera fusca), Apple powdery mildew (Podosphaera leucotricha), Rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), Zucchini and Japanese melon powdery mildew (Podosphaera xanthii), Strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), Watermelon and melon powdery mildew (Sphaerotheca fuliginea), Grape powdery mildew (Uncinula necator, U. n. var. necator), Apple Blotch (Diplocarpon mali), Rose black spot (Diplocarpon rosae), Onion gray mold neck rot (Botrytis allii), Gray mold, Botrytis blight (Botrytis cinerea), Chinese chive leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), Broad bean chocolate spot (Botrytis cinerea, B. elliptica, B. fabae), Brown rot (Monilinia fructicola, M. fructigena, M. laxa), Apple blossom blight (Monilinia mali), Dollar spot (Sclerotinia homoeocarpa), Cottony rot, Sclerotinia rot, Stem rot (Sclerotinia sclerotiorum), False smut (Villosiclava virens), Soybean root necrosis (Calonectria ilicicola), Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae,Monographella nivalis), Fusarium blight (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of taro (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), Fusarium wilt of adzuki bean (Fusarium oxysporum f. sp. adzukicola), Fusarium basal rot of Chinese chive (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem rot of sweet potato (Fusarium oxysporum f. sp. batatas, F. solani), Dry rot of taro (Fusarium oxysporum f. sp. colocasiae), Yellows of cabbage and Komatsuna (Fusarium oxysporum f. sp. conglutinans), Panama disease of banana (Fusarium oxysporum f. sp. cubense), Fusarium wilt of strawberry (Fusarium oxysporum f. sp. fragariae), Root rot of lettuce (Fusarium oxysporum f. sp. lactucae), Fusarium wilt of watermelon (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), Fusarium wilt of tomato (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt of melon (Fusarium oxysporum f. sp. melonis), Yellows of radish (Fusarium oxysporum f. sp.raphani), Fusarium wilt (Fusarium oxysporum f. sp. spinaciae), Soybean Sudden Death Syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), Bakanae disease (Gibberella fujikuroi), Verticillium black spot (Verticillium albo-atrum, V. dahliae), Verticillium wilt (Verticillium dahliae) of tomato, eggplant, and butterbur, Ceratocystis canker (Ceratocystis ficicola) of fig, Black rot (Ceratocystis fimbriata) of sweet potato, Gray spot disease of tea blight (Pestalotiopsis longiseta, P. theae), Endothia canker (Cryphonectria parasitica), Melanose (Diaporthe citri), Stem blight (Phomopsis asparagi), Pear canker (Phomopsis fukushii), Brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Valsa canker (Valsa ceratosperma), Rice blast (Magnaporthe grisea), Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), Bitter rot (Colletotrichum acutatum, Anthracnose (Colletotrichum acutatum, Glomerellacingulata), Plum anthracnose (Colletotrichum acutatum), Grape rot (Colletotrichum acutatum, Glomerella cingulata), Garland chrysanthemum anthracnose (Colletotrichum acutatum), Bean anthracnose (Colletotrichum lindemuthianum), Cucurbit anthracnose (Colletotrichum orbiculare), Chinese yam anthracnose (Glomerella cingulata), Chestnut anthracnose (Glomerella cingulata), Persimmon anthracnose (Glomerella cingulata), Adzuki bean brown stem rot (Phialophora gregata), Chinese yam leaf astringency (Leaf Spot (Pseudophloeosporella dioscoreae), Scald (Rhynchosporium secalis), Brown rust (Puccinia recondita), Stripe rust (Puccinia striiformis), Rust that occurs in various crops, Fig rust (Phakopsora nishidana), Soybean rust (Phakopsora pachyrhizi), Rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Pear red spot (Gymnosporangium asiaticum), Apple red spot (Gymnosporangium yamadae), Onion rust (Puccinia allii), Chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisoriumscitamineum), corn smut (Ustilago maydis), barley loose smut (Ustilago nuda), tea net blister blight (Exobasidium reticulatum), tea blister blight (Exobasidium vexans), stem rot, southern blight (Athelia rolfsii), chrysanthemum root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger sheath blight (Rhizoctonia solani), cabbage damping-off (Rhizoctonia solani), mitsuba damping-off (Rhizoctonia solani), lettuce bottom rot (Rhizoctonia solani), turfgrass brown patch, large patch (Rhizoctonia solani), rice sheath blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), leaf blight (Thanatephorus cucumeris), fig black mold disease (Rhizopus stolonifer var. stolonifer), clubroot disease (Plasmodiophora brassicae), sugar beet black mold disease (Aphanomyces root rot (Aphanomyces cochlioides), white rust (Albugo macrospora), downy mildew on various crops, lettuce downy mildew (Bremia lactucae), chrysanthemum downy mildew (Peronospora chrysanthemi-coronarii), onion and leek downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp. spinaciae), soybean downy mildew (Peronosporamanshurica, Cruciferous downy mildew (Peronospora parasitica), Rose downy mildew (Peronospora sparsa), Sunflower downy mildew (Plasmopara halstedii), Honeybee downy mildew (Plasmopara nivea), Grape downy mildew (Plasmopara viticola), Cucurbit downy mildew (Pseudoperonospora cubensis), Phytophthora root rot (Phytophthora cactorum), Watermelon brown rot (Phytophthora capsici), Pumpkin late blight (Phytophthora capsici), Bell pepper late blight (Phytophthora capsici), Watermelon late blight (Phytophthora cryptogea), Tomato and potato late blight (Phytophthora infestans), Fig Phytophthora Wh Phytophthora powdery rot (Phytophthora palmivora), Leaf blight (Phytophthora porri), Phytophthora root and stem rot (Phytophthora sojae), Phytophthora stem rot (Phytophthora vignae f. sp. adzukicola), Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Root rot (Pythium aristosporum), Browning root rot (Pythium arrhenomanes, P. graminicola), Damping-off (Pythium buismaniae, P. myriotylum), Root rot (Pythium mioga) rot (Pythium myriotylum), ginger root rot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato bacterial canker (Clavibacter michiganensis subsp. michiganensis), potato scab (Streptomyces spp.), rose crown gall (Rhizobium radiobacter), sorghum bacterial stripe (Burkholderia andropogonis), onion soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), rice bacterial grain rot (Burkholderia gladioli, B.glumae), watermelon bacterial fruit blotch (Acidovorax avenae subsp. citrulli), konjac bacterial leaf blight (Acidovorax konjaci), bacterial wilt (Ralstonia solanacearum), peach bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), plum bacterial leaf spot (Xanthomonas arboricola pv. pruni), lettuce bacterial spot (Xanthomonas axonopodis pv. vitians), crucifer black rot (Xanthomonas campestris pv. campestris), soybean bacterial leaf spot pustule (Xanthomonas campestris pv. glycines), bacterial spot (Xanthomonas campestris pv. nigromaculans), bacterial spot (Xanthomonas campestris pv. vesicatoria), citrus canker (Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), kiwifruit bacterial blossom blight (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P.viridiflava), kiwi fruit canker (Pseudomonas syringae pv. actinidiae), loquat canker (Pseudomonas syringae pv. eriobotryae), Cucurbitaceae bacterial spot disease (Pseudomonas syringae pv. lachrymans), Brassicaceae bacterial black spot disease (Pseudomonas syringae pv. maculicola), plum canker disease (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), tea shoot blight disease (Pseudomonas syringae pv. theae), onion soft rot disease (Dickeya sp., Pectobacterium carotovorum), and fire blight disease (Rosaceae Pear subfamily). These include konjac blight (Erwinia amylovora), soft rot (Pectobacterium carotovorum), and bacterial soft rot (Pectobacterium carotovorum).

[0140] Development of control agents for diseases of agricultural and horticultural crops has progressed, and a wide variety of drugs have been put to practical use to date. However, due to the long-term use of these drugs, in recent years, pathogenic bacteria have acquired drug resistance, and there are increasing cases in which control with existing fungicides that have been used in the past is difficult. In addition, some of the existing drugs are highly toxic, and some of them remain in the environment for a long time, which is causing problems in disrupting the ecosystem. Under such circumstances, the compound of the present invention has excellent control activity against many pathogenic bacteria and is highly safe for the target crops. In addition, the compound of the present invention can exert a sufficient control effect even against pathogenic bacteria that have acquired resistance to existing fungicides. Furthermore, the compound of the present invention does not cause phytotoxicity to the target crops, has almost no adverse effect on mammals, fish, and beneficial insects, and has low residual properties and a low burden on the environment.

[0141] In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as a medical antibacterial agent and an antibacterial agent for animals, used as an antifungal agent or an internal parasite control agent, as an antibacterial and antifungal agent for wood, paper and pulp, adhesives, paints, fibers, leather, etc., and as an industrial fungicide for cooling water channels in manufacturing plants, etc.

[0142] Examples of pathogenic bacteria that can be used as medical antibacterial agents or veterinary antibacterial agents include, but are not limited to, tinea fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Haemophilus influenzae, and gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0143] Examples of strains that can be used as antibacterial and antifungal agents include wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, and material-deteriorating 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, but are not limited to these.

[0144] Examples of fungal strains that can be used as industrial fungicides include slime fungi such as Sphaerotilis natans and Zoogloea ramigera, but are not limited to these.

[0145] The compound of the present invention can be used not only as an agricultural or horticultural fungicide but also as an agent for controlling internal parasites in livestock, poultry, pets, etc.

[0146] Specific examples of target internal parasites include, but are not limited to, the following: Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus ylus, Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, and other nematodes; Filariidae nematodes, such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Dracunculidae nematodes, such as Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium cestodes such as Echinococcus latum), Diphyllobothrium erinacei, Echinococcus granulosus, and Echinococcus multilocularis; Fasciola hepatica, F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma trematodes such as Schistosoma haematobium (japonicum), Schistosoma haematobium, and Schistosoma mansoni; 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., and the like.

[0147] The compounds of the present invention can be used as antifungal agents in addition to being used as agricultural and horticultural fungicides.

[0148] Specific examples of pathogenic bacteria that can be used as antifungal agents include, but are not limited to, the following. Trichophyton rubrum, Trichophyton mentagrophytes and other tinea fungi, Candida albicans and other Candida fungi, Aspergillus fumigatus and other Aspergillus fungi, Cryptococcus neoformas and other Cryptococcus fungi, and the like.

[0149] When the compound of the present invention is applied as a plant disease and plant pest control agent, it is usually mixed with a suitable solid or liquid carrier, and further, if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, antidecomposition agents, etc. are added to the compound, and the compound can be practically used in any formulation such as a soluble concentrate, emulsifiable concentrate, wettable powder, water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, gel, etc. From the viewpoint of labor saving and safety improvement, the compound of any formulation as above can be enclosed in a water-soluble package and used.

[0150] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; synthetic silicic acid; and synthetic silicates.

[0151] Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol, isopropanol, etc., aromatic hydrocarbons such as xylene, alkylbenzene, alkylnaphthalene, etc., ethers such as butyl cellosolve, ketones such as cyclohexanone, esters such as γ-butyrolactone, acid amides such as N-methylpyrrolidone, N-octylpyrrolidone, etc., vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, castor oil, etc., water, etc. These solid and liquid carriers may be used alone or in combination of two or more.

[0152] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styryl phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styryl phenyl ether sulfates or phosphates, polycarboxylates, and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; and amphoteric surfactants such as amino acid type and betaine type.

[0153] The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more kinds.

[0154] When the compound of the present invention is used as a pesticide, it may be mixed with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying, if necessary.

[0155] In particular, by applying it in combination with other pesticides or plant hormones, it is possible to reduce the amount of drug applied and thereby reduce costs, and to expand the bactericidal and insecticidal spectrum and achieve a higher pest control effect due to the synergistic effect of the mixed drug. In this case, it is also possible to combine it with multiple known pesticides at the same time.

[0156] In one embodiment, the types of pesticides to be mixed with the compound of the present invention include, for example, compounds listed in The Pesticide Manual, 18th Edition, 2018. Specific examples of their common names are as follows. However, the pesticides to be mixed are not necessarily limited to these. 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, benzamorph, 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 chromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decaphentin, dehydroacetic acid acid), dichlobentiazox, dichlofluanid, diclone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine,Dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4 nocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine ne), drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamide fenamidone, fenaminosulf, phenaminestrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid,Fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetober, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfa Flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl-aluminium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, furcarbanil, Conazole, fluconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos,8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole ole), ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofetamide, isoflucipram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin, kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil onil, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolone, metconazole, methasulfocarb, metfuroxam, metyltetraprole, metiram, metominostrobin,Metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole fumarate fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, orthophenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxin-D, potassium azide, potassium hydrogen carbonate carbonate), probenazole, prochloraz, procymidone, propamocarb hydrochloride, propiconazole, propineb,Proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid , pyridaclomethyl, pyridinitril, pyriophenone, 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, thiochloro, Thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil, tioximid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide oxide, trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, and shiitake fruiting body extract. Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, a 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 smethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, chlorethxyfos,Chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine zine, clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin alothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezotia z), dicofol, dienochlor, diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC,dT-80-phthalthrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethifencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubenzi Flubendiamide, fluchlordiniliprole, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin,Fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, indoxacarb-MP, isocycloceram seram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, lepimectin, lufenuron, malathion, meperfluthrin luthrin, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrin, milbemectin, momfluorothrin,Monocrotophos, Muscalure, Nicofluprole, Nitenpyram, Novaluron, Noviflumuron, Omethoate, Oxazosulfyl, Oxydemeton-methyl, Oxydeprofos, Parathion, Parathion-methyl arathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, praziquantel iquantel, 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, spiropidione, spirotetramat, spiromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin rin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion and zeta-cypermethrin, etc. Parasiticides: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin fluthrin, zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, Pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos , ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenocarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,Tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin, madeuramycin, milbemycin, milbemycin oxime oxime, moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsomine dihydrochloride, metronidazole, methylidine,Monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, and triclabendazole, etc. Antifungals: such as ketoconazole and miconazole nitrate. Antibacterial 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 acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Talaromyces, Trichoderma, and Uniothyrium, etc.

[0157] The application amount of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but generally, an appropriate amount of active ingredient is 0.005 to 50 kg per hectare (ha), and preferably 0.01 to 1 kg.

[0158] Next, examples of formulations using the compound of the present invention are shown below. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[0159] [Wettable powder] 0.1 to 80 parts of the compound of the present invention Solid carrier 5 to 98.9 parts Surfactant 1-10 parts Others 0~5 Other examples include anti-caking agents, anti-decomposition agents, etc.

[0160] 〔emulsion〕 Compound of the present invention 0.1 to 30 parts Liquid carrier 45-95 parts Surfactant 4.9 to 15 parts Others 0-10 Other examples of the additives include a spreading agent and a decomposition inhibitor.

[0161] [Suspension Agent] 0.1 to 70 parts of the compound of the present invention Liquid carrier 15 to 98.89 parts Surfactant 1-12 parts Others 0.01 to 30 parts Other examples include antifreeze agents and thickeners.

[0162] [Water dispersible granule] 0.1 to 90 parts of the compound of the present invention Solid carrier 0 to 98.9 parts Surfactant 1-20 parts Others 0-10 Other examples include binders, anti-decomposition agents, etc.

[0163] [Liquid] Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 Other examples include antifreeze agents, spreading agents, etc.

[0164] [Granules] Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0-10 Other examples include binders, anti-decomposition agents, etc.

[0165] [Powder] Compound of the present invention 0.01 to 30 parts Solid carrier 65 to 99.99 parts Others 0~5 Other examples include drift inhibitors and decomposition inhibitors.

[0166] When used, the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, and then sprayed, or without dilution.

[0167] Next, specific formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient are shown below, but the present invention is not limited to these. In the following formulation examples, "parts" means parts by weight.

[0168] [Formulation Example 1] Emulsion Compound No. 1-001 of the present invention 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (Mixture of nonionic surfactant and anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) The above ingredients are mixed uniformly to prepare an emulsifiable concentrate. When used, the emulsifiable concentrate is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0169] [Formulation Example 2] Wettable powder Compound No. 1-001 of the present invention 25 parts Pyrophyllite 66 parts Solpol 5039 4th part (Anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Carplex #80D Part 3 (White carbon: product name, manufactured by Shionogi & Co., Ltd.) Calcium lignosulfonate 2 parts The above ingredients are mixed and crushed uniformly to prepare a wettable powder. When used, the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0170] [Formulation Example 3] Powder Compound No. 1-001 of the present invention Part 3 Carplex #80D 0.5 parts (White carbon: product name, manufactured by Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are mixed and crushed uniformly to prepare a powder. When used, the powder is spread so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0171] [Formulation Example 4] Granules Compound No. 1-001 of the present invention Part 5 30 parts bentonite Talc 64 parts Calcium lignosulfonate 1 part The above ingredients are mixed and crushed uniformly, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to obtain granules. When used, the granules are sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0172] [Formulation Example 5] Suspension Compound No. 1-001 of the present invention 25 parts Solpol 3353 5th Division (Nonionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Lunox 1000C 0.5 parts (Anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts The above ingredients except for the active ingredient (the compound of the present invention) are uniformly dissolved, then the compound of the present invention is added and thoroughly stirred, and then wet-pulverized in a sand mill to obtain a flowable formulation. When used, the flowable formulation is diluted 50 to 20,000 times with water and sprayed so that the amount of the active ingredient becomes 0.005 to 50 kg per hectare.

[0173] [Formulation Example 6] Granular water dispersible agent Compound No. 1-001 of the present invention 75 parts High Tenor NE-15 5 parts (Anionic surfactant: Trade name, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) Vanillex N 10 parts (Anionic surfactant: Trade name, manufactured by Nippon Paper Industries Co., Ltd.) Carplex #80D 10 copies (White carbon: product name, manufactured by Shionogi & Co., Ltd.) The above ingredients are mixed and pulverized uniformly, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to make a dry flowable agent. When used, it is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.

[0174] Methods for applying the compound of the present invention include foliage spray, soil treatment, seed disinfection, etc., but common methods commonly used by those skilled in the art are also effective.

[0175] 〔summary〕 As described above, the embodiments of the present invention relate to the following [1] to [7]. [1] Formula (1):

[0176] [ka]

[0177] [In the formula, G represents G-1, G-1 represents a structure represented by the following structural formula:

[0178] [ka]

[0179] G 1 is a hydroxyl, nitro, cyano, halogen atom, C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, R b C replaced with 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, di(C 1 ~C 6 Alkyl)amino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, C 3 ~C 10 Cycloalkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', G 1 In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G1 may be the same as or different from each other, R b Cyano, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', R is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R' is C 1 ~C 6 represents an alkyl group, T represents an oxygen atom or a sulfur atom; R X is C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, R c C replaced with 1 ~C 6 Alkyl, benzyl, R X -1, R X -2, R X -3 or R X represents -4, R X -1~R X -4 represents a structure represented by the following structural formula,

[0180] [ka]

[0181] X 1 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl or C 1 ~C 6 represents alkoxy, X 1 In the relationship, when u5 is an integer of 2, 3, 4 or 5, each X 1 may be the same as or different from each other, X 1 In the relationship between X and u4, when u4 is an integer of 2, 3 or 4, 1 may be the same as or different from each other, R c Cyano, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkoxycarbonyl, C 1 ~C 6 Alkylaminocarbonyl, di(C 1 ~C 6 -C(=NOR)R', R Y is a hydrogen atom, a halogen atom or C 1 ~C 6 represents an alkyl group, R 1 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 2 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 3 is a hydrogen atom or C 1 ~C 6 represents an alkyl group, R 4 -OR a represents R 5 is a hydrogen atom, C 1 ~C 6 Alkyl or C 1 ~C 6 represents haloalkyl, Or, R 4 and R 5 Together, C 2 ~C 5 By forming an alkylene chain, R4 and R 5 represents that the ring is formed of 3 to 6 members together with the carbon atom to which it is bonded. R a is a hydrogen atom, C 1 ~C 6 Alkylcarbonyl or C 1 ~C 6 represents haloalkylcarbonyl; Z represents Z-1 to Z-7 or Z-8; Z-1 to Z-8 each represent a structure represented by the following structural formula:

[0182] [ka]

[0183] In addition, Z 1 The substitution position of represents a substitution on the aromatic ring of Z-1 to Z-8, Z 1 is hydroxy, carboxy, amino, nitro, cyano, halogen atom, C 1 ~C 6 Alkyl, C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Haloalkyl, C 3 ~C 10 Halocycloalkyl, C 2 ~C 6 Alkenyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Alkylthio, C 1 ~C 6 Alkylsulfinyl, C 1 ~C 6 Alkylsulfonyl, C 1 ~C 6 Alkylamino, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 Alkoxycarbonyl, R i C replaced with 1 ~C 6 Alkyl, -ORd , -NHC(O)R e , -NR h C(O)R e , -NHSO 2 R f , -C≡CR g , -SO 2 NH 2 , -C(=NOR)R', E-1 to E-54, F-1 to F-14 or F-15; Z 1 In the case where n7 is an integer of 2, 3, 4, 5, 6 or 7, each Z 1 may be the same as or different from each other, Z 1 In the case where n5 is an integer of 2, 3, 4 or 5, each Z 1 may be the same as or different from each other, Z 1 In the case where n4 is an integer of 2, 3 or 4, each Z 1 may be the same as or different from each other, Z 1 In the case where n3 is an integer of 2 or 3, each Z 1 may be the same as or different from each other, R d is C 2 ~C 6 Alkenyl, C 2 ~C 6 Alkynyl, C 1 ~C 6 Haloalkyl, R 10 C replaced with 1 ~C 6 Alkyl, C 1 ~C 6 Alkyl carbonyl, C 1 ~C 6 alkylaminocarbonyl, E-1 to E-54, F-1 to F-14 or F-15; R 10 is C 3 ~C 10 Cycloalkyl, C 1 ~C 6 Alkyl carbonyl, C1 ~C 6 Alkoxycarbonyl, di(C 1 ~C 6 -C(=NOR)R', E-1 to E-54, F-1 to F-14 or F-15; R e is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, C 2 ~C 6 Alkenyloxy, C 1 ~C 6 Alkylamino, di(C 1 ~C 6 alkyl)amino, benzyloxy, E-1 to E-54, F-1 to F-14 or F-15; R f is C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, di(C 1 ~C 6 alkyl)amino, E-1 to E-54, F-1 to F-14 or F-15; R g is a hydrogen atom or tri(C 1 ~C 4 alkyl)silyl; R h is C 1 ~C 6 represents an alkyl group, R i is hydroxy or C 1 ~C 6 represents alkoxy, E-1 to E-54 each represent a structure represented by the following structural formula:

[0184] [ka]

[0185] [ka]

[0186] F-1 to F-15 each represent a structure represented by the following structural formula:

[0187] [ka]

[0188] Z a is a halogen atom, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 Alkoxy, C 1 ~C 6 Haloalkoxy, C 1 ~C 6 Alkylcarbonyl or C 1 ~C 6 represents an alkoxycarbonyl; Z a In the case where v7 is an integer of 2, 3, 4, 5, 6 or 7, each Z a may be the same as or different from each other, Z a In the case where v6 is an integer of 2, 3, 4, 5 or 6, each Z a may be the same as or different from each other, Z a In the relationship between v5 and Z, when v5 is an integer of 2, 3, 4 or 5, a may be the same as or different from each other, Z a In the case where v4 is an integer of 2, 3 or 4, each Z a may be the same as or different from each other, Z a In the case where v3 is an integer of 2 or 3, each Z a may be the same as or different from each other, Za In the relationship between v2 and each Z a may be the same as or different from each other, Z b is C 1 ~C 6 represents an alkyl group, m5 represents an integer of 0, 1, 2, 3, 4 or 5; n7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; n5 represents an integer of 0, 1, 2, 3, 4 or 5; n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2 or 3; u5 represents an integer of 0, 1, 2, 3, 4 or 5; u4 represents an integer of 0, 1, 2, 3, or 4; v7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; v6 represents an integer of 0, 1, 2, 3, 4, 5, or 6; v5 represents an integer of 0, 1, 2, 3, 4, or 5; v4 represents an integer of 0, 1, 2, 3, or 4; v3 represents an integer of 0, 1, 2, or 3; v2 represents an integer of 0, 1, or 2; v1 represents an integer of 0 or 1. A pyrazole compound represented by the following formula (1): [2] G 1 is C 1 ~C 6 Alkyl or C 1 ~C 6 represents haloalkyl, T represents an oxygen atom; R X is C 1 ~C 6 Alkyl or R X represents -2, R Y represents a hydrogen atom, R 1 represents a hydrogen atom, R 2 represents a hydrogen atom, R 3 represents a hydrogen atom, Z represents Z-1 or Z-8; Z 1 is a halogen atom, C 1 ~C 6 Alkyl, C 1 ~C 6 represents alkoxy or E-3, Z a represents a halogen atom, m5 represents an integer of 0 or 1; n5 represents an integer of 0, 1 or 2; n4 represents an integer of 2, u4 represents the integer 0, The pyrazole compound or salt thereof according to the above [1], wherein v4 represents an integer of 1. [3] An agricultural chemical comprising at least one selected from the pyrazole compounds and salts thereof according to any one of [1] and [2] above as an active ingredient. [4] A fungicide comprising at least one pyrazole compound and a salt thereof according to any one of [1] and [2] above as an active ingredient. [5] An agricultural and horticultural fungicide comprising at least one pyrazole compound and a salt thereof according to any one of [1] and [2] above as an active ingredient. [6] An antifungal agent comprising at least one pyrazole compound and a salt thereof according to any one of [1] and [2] above as an active ingredient. [7] An internal parasite control agent comprising, as an active ingredient, at least one selected from the pyrazole compounds and salts thereof according to any one of [1] and [2] above. [Example] The present invention will be explained in more detail below 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.

[0189] The medium pressure preparative liquid chromatography described in the synthesis examples was carried out using a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).

[0190] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter, 1 The chemical shift values ​​of H-NMR are expressed as Me 4 Using Si (tetramethylsilane), measurements were performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). 1 The symbols in the H-NMR chemical shift values ​​have the following meanings. s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, sep: septet, m: multiplet, br: broad singlet.

[0191] [Synthesis example] Synthesis Example 1: Synthesis of 1-(tert-butyl)-N-(2-(2-chloro-4-methylphenyl)-2-hydroxyethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-022) To a mixed solution of 1.50 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 20 ml of dichloromethane, 0.40 ml of oxalyl chloride and 19 mg of N,N-dimethylformamide were added in sequence at room temperature, and the mixture was stirred at the same temperature for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure, and 10 ml of dichloromethane was added to the resulting residue. The reaction mixture was added to a mixed solution of 1.00 g of 2-amino-1-(2-chloro-4-methylphenyl)ethan-1-ol, 1.3 ml of triethylamine, and 10 ml of dichloromethane under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After the reaction was completed, 20 ml of 1 mol / l hydrochloric acid was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml x 1 time). The obtained organic layer was washed with 1 mol / l aqueous sodium hydroxide solution, then dehydrated and 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 n-hexane:ethyl acetate [gradient from 9:1 to 1:9 (volume ratio, the same applies below)] as an eluent, and 1.70 g of the target product was obtained as a white solid. Melting point: 86-89℃.

[0192] Synthesis Example 2: Synthesis of 2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido-1-(2,4-dimethylphenyl)ethyl acetate (Compound No. 1-007) To a mixed solution of 100 mg of 1-(tert-butyl)-N-(2-(2,4-dimethylphenyl)-2-hydroxyethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 33 mg of pyridine, and 2 ml of dichloromethane, 43 mg of acetic anhydride was added at room temperature and stirred at the same temperature for 16 hours. After the reaction was completed, 2 ml of 1 mol / l hydrochloric acid was added and extracted with chloroform (2 ml x 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, and 79 mg of the target product was obtained as a colorless oil. 1 H-NMR (CDCl 3 , Me 4 Si, 300MHz):δ7.48-7.42 (m, 1H), 7.40-7.35 (m, 1H), 7.32-7.28 (m, 1H), 7.20-7.13 (m, 3H), 6.97-6.90 (m, 2H), 6.81-6.71 (m, 1H), 6.05-5.99 (m, 1H), 3.86-3.77 (m, 1H), 3.63-3.53 (m, 1H), 2.35 (s, 3H), 2.26 (s, 3H), 1.91 (s, 3H), 1.72 (s, 9H).

[0193] [Reference example] The methods for producing intermediates for producing the compounds of the present invention are shown below as Reference Examples.

[0194] Reference Example 1: Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid To a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid, 2.5 g of N-iodosuccinimide was added at room temperature and 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. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target product as a pink solid. Melting point: 191-193℃.

[0195] Reference Example 2: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one A mixed solution of 4.7 g of 1-(3-(trifluoromethyl)phenoxy)propan-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 resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent. 10 ml of diisopropyl ether and 10 ml of n-hexane were added to the resulting oily matter, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to obtain 2.36 g of the target product as a light brown solid. Melting point: 112-114°C.

[0196] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-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 resulting residue, and the mixture was extracted with n-hexane (20 ml x 2 times). The resulting organic layer was dehydrated and dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (5:1) as an eluent to obtain 2.51 g of the target product as a pale yellow oil. 1 H-NMR (CDCl 3 , Me 4 Si, 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).

[0197] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 930 mg of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butyl alcohol, and 4.3 ml of water, 1.48 g of potassium permanganate was added at room temperature, 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 the same temperature, and the mixture was stirred at the same temperature for 2 hours. After the reaction was completed, the reaction mixture was filtered through Celite, and the Celite was washed with 20 ml of water. The aqueous layer of the obtained filtrate was washed with chloroform (20 ml x 2 times), and then 1 mol / l aqueous hydrochloric acid was added until the pH became 1, and the mixture was extracted with chloroform (20 ml x 2 times). The obtained organic layer was washed with water, dehydrated and dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 ml of n-hexane and then dried under reduced pressure to obtain 209 mg of the desired product as a white solid. Melting point: 120-124℃.

[0198] Reference Example 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrylaldehyde 5.6 ml of phosphorus oxychloride was added to 15 ml of N,N-dimethylformamide under ice cooling, and the mixture was stirred at the same temperature for 15 minutes. After the stirring was completed, 5 ml of 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 the mixture was 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 the mixture was stirred at room temperature for 1 hour. After the stirring was completed, the reaction mixture was extracted with toluene (40 ml x 2 times). The obtained organic layer was washed with water, dehydrated and dried with saturated saline 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. 1 H-NMR (CDCl 3 , Me 4Si, 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).

[0199] Step 2: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.0 g of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrylaldehyde, 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 1 mol / l aqueous hydrochloric acid was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml x 2 times). The organic layer obtained was washed with water, dehydrated and dried with saturated saline and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, and 400 mg of the target product was obtained as a red oil. 1 H-NMR (CDCl 3 , Me 4 Si, 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) Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Under a nitrogen atmosphere, 0.85 ml of a 1.6 mol / l n-butyllithium n-hexane solution was dropped into 10 ml of a tetrahydrofuran solution of 360 mg of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole at -78°C, and the mixture was stirred at the same temperature for 10 minutes. After the stirring was completed, 1.0 g of dry ice was added to the reaction mixture at -78°C, and the mixture was stirred at the same temperature for 5 minutes. After the reaction was completed, 10 ml of a 1 mol / l aqueous hydrochloric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml x 2 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate:acetic acid (gradient from 74:25:1 to 39:60:1) as an eluent, and 45 mg of the target product was obtained as a colorless solid. Melting point: 124-126℃.

[0200] Reference Example 4: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate (Compound No. ii-004) 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, 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were added successively at room temperature, and the mixture was stirred at the same 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 resulting residue, and the mixture was extracted with ethyl acetate (20 ml x 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target product as a yellow solid. Melting point: 69-71°C.

[0201] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (Compound No. ii-005) Under a nitrogen atmosphere, 0.50 g of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxine, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane were added to a mixture solution at room temperature and stirred at 100°C for 16 hours. After the reaction was completed, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml x 3 times). After dehydration and drying with saturated saline and then anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 10:0 to 9:1) as an eluent, and 0.30 g of the target product was obtained as a yellow oil. 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).

[0202] Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) To a mixed solution of 39.0 g of methyl (1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol, a mixed solution of 27.1 g of sodium hydroxide and 100 ml of water was added at room temperature, and the mixture was stirred at 45° C. for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 50 ml of water was added to the obtained residue, and then 35% by mass hydrochloric acid was added until the pH became 2, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure and washed with 100 ml of n-hexane to obtain 37.0 g of the target product as a white solid. Melting point: 116-118°C.

[0203] The compound 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, which are produced in the same manner as synthesis examples 1 and 2, are shown in Tables 1 to 4, and examples of intermediates produced in the same manner as reference examples 1 to 4 are shown in Tables 5 and 6, but the pyrazole compounds and intermediates included in the present invention are not limited to these.

[0204] In the table, the substituent marked "Me" represents "methyl", and similarly, "tBu" represents "tertiary butyl", "iPr" represents "isopropyl", "cPr" represents "cyclopropyl", "Ph" represents "phenyl", and "Bn" represents "benzyl". In addition, the notation "*" indicates that the compound is an oily or resinous compound with no melting point, and "mp" represents the melting point (unit: °C).

[0205] In the table, for example, the description "4-" in "4-Me-Ph" indicates the substitution position on the phenyl group as described below. For example, "4-Me-Ph" is 4-methylphenyl, "2,6-F 2 For example, the notation "4-" in "1-Me-Ph" represents the substitution position on the phenyl group as described below. For example, "4-Me-Ph" represents 4-methylphenyl, "2,6-F 2 "-Ph" represents 2,6-difluorophenyl.

[0206] [ka]

[0207] The substituents represented by E-2a, E-3a, and E-4a each have the following structure.

[0208] [ka]

[0209] In the above diagram, the numbers in the structural formula indicate the substitution positions, and for example, "6-OMe-(E-3a)" in the table indicates the following structure. Those without a substituent indicate that the compound is unsubstituted.

[0210] [ka]

[0211] [Table 1]

[0212] [ka]

[0213] ---------------------------------------------------------------------------------- No. GZR X R 4 R 5 mp(℃) ---------------------------------------------------------------------------------- 1-001 3-CF 3 -Ph2-OMe-PhtBuOHH* 1-002 3-CF 3 -Ph4-Cl-PhtBuOH CF 3 * 1-003 3-CF 3 -Ph4-Cl-PhtBuOHH* 1-004 Ph 4-Cl-Ph tBu OH H 119-121 1-005 3-CF 3 -Ph 4-Me-Ph tBu OH H * 1-006 3-CF 3 -Ph4-Me-PhtBuOHMe* 1-007 3-CF 3 -Ph 2,4-Me 2 -Ph tBu OC(O)Me H * 1-008 3-CF 3 -Ph 2,4-Me2 -Ph tBu OC(O)CF 3 H * 1-009 Ph 4-Me-Ph tBu OH Me * 1-010 Ph 2,4-Me 2 -Ph tBu OH H * 1-011 3-CF 3 -Ph 2,4-Cl 2 -Ph tBu OH H * 1-012 3-Me-Ph 2,4-Me 2 -Ph tBu OH H * 1-013 3-Me-Ph 4-Me-Ph tBu OH Me * 1-014 3-CF 3 -Ph 2,4-Me 2 -Ph tBu OH H * 1-015 3-CF 3 -Ph 4-Cl-Ph tBu OH Me * 1-016 3-CF 3 -Ph 2,4-Me 2 -Ph E-2a OH H * 1-017 3-CF 3 -Ph 2,4-Cl 2 -Ph E-2a OH H * 1-018 3-CF 3 -Ph 4-Me-Ph E-2a OH Me * 1-019 3-CF 3 -Ph 4-OMe-Ph tBu OH H * 1-020 Ph 4-OMe-Ph tBu OH H * 1-021 3-Me-Ph 4-OMe-Ph tBu OH H * 1-022 3-CF 3 -Ph 2-Cl-4-Me-Ph tBu OH H 86-89 1-023 Ph 2-Cl-4-Me-Ph tBu OH H 103-106 1-024 3-Me-Ph 2-Cl-4-Me-Ph tBu OH H 76-79 1-025 3-Methylphenyl 4-Chlorophenyl tert-Butyl Hydroxide Methyl 94-96 1-026 3-Methylphenyl 4-Bromophenyl tert-Butyl Hydroxide Methyl 99-101 1-027 3-Methylphenyl 2,4-Dimethyl 2 -Phenyl tert-Butyl Hydroxide Methyl * 1-028 3-Methylphenyl 2,4-Dichloro 2 -Phenyl tert-Butyl Hydroxide Methyl * 1-029 3-Trifluoromethyl 3 -Phenyl 4-Bromophenyl tert-Butyl Hydroxide Methyl * 1-030 3-Trifluoromethyl 3 -Phenyl 2,4-Dimethyl 2 -Phenyl tert-Butyl Hydroxide Methyl * 1-031 3-Trifluoromethyl 3 -Phenyl 2,4-Dichloro 2 -Phenyl tert-Butyl Hydroxide Methyl * ―――――――――――――――――――――――――――――――――― [Table 2]

[0214]

Chem.

[0215] ―――――――――――――――――――――――――――――――― No. G Z R X m.p.(°C) ―――――――――――――――――――――――――――――――― 2-001 3-Trifluoromethyl 3 -Phenyl 2-Methoxyphenyl tert-Butyl * 2-002 Phenyl 2-Methoxyphenyl tert-Butyl * 2-003 3-Trifluoromethyl 3 -Phenyl 2-Chloro-4-Bromophenyl tert-Butyl * 2-004 3-Trifluoromethyl 3 -Phenyl 4-Methylphenyl tert-Butyl * 2-005 3-Methylphenyl 4-Methylphenyl tert-Butyl * 2-006 Ph 4-Me-Ph tBu * 2-007 3-CF 3 -Ph 4-Br-Ph tBu * 2-008 Ph 4-Br-Ph tBu * 2-009 3-CF 3 -Ph Ph tBu * 2-010 Ph Ph tBu * 2-011 3-Me-Ph 4-Cl-Ph tBu 79-80 2-012 3-Me-Ph 4-Br-Ph tBu * 2-013 3-CF 3 -Ph 4-Cl-Ph tBu 103-104 2-014 3-Me-Ph 4-OMe-Ph tBu * 2-015 3-CF 3 -Ph 4-OMe-Ph tBu * 2-016 3-Me-Ph 2,4-Cl 2 -Ph tBu * 2-017 3-CF 3 -Ph 2,4-Cl 2 -Ph tBu * 2-018 3-CF 3 -Ph 4-(6-F-(E-3a))-Ph tBu 127-129 2-019 Ph 4-(6-F-(E-3a))-Ph tBu * 2-020 3-Me-Ph 3,4-(OMe) 2 -Ph tBu * 2-021 3-CF 3 -Ph 3,4-(OMe) 2 -Ph tBu * 2-022 3-CF 3 -Ph 2-Cl-4-OMe-Ph tBu 2-023 3-Me-Ph 2-Cl-4-OMe-Ph tBu 2-024 3-Cl-Ph 2-Cl-4-OMe-Ph tBu 2-025 Ph 2-Cl-4-OMe-Ph tBu 2-026 3-CF3 -Ph 2-Me-4-OMe-Ph tBu 2-027 3-Me-Ph 2-Me-4-OMe-Ph tBu 2-028 3-Cl-Ph 2-Me-4-OMe-Ph tBu 2-029 Ph 2-Me-4-OMe-Ph tBu 2-030 3-CF 3 -Ph 2-Br-4-OMe-Ph tBu 2-031 3-Me-Ph 2-Br-4-OMe-Ph tBu 2-032 3-Cl-Ph 2-Br-4-OMe-Ph tBu 2-033 Ph 2-Br-4-OMe-Ph tBu 2-034 3-CF 3 -Ph 2,4-(OMe) 2 -Ph tBu 2-035 3-Me-Ph 2,4-(OMe) 2 -Ph tBu 2-036 3-Cl-Ph 2,4-(OMe) 2 -Ph tBu 2-037 Ph 2,4-(OMe) 2 -Ph tBu 2-038 3-CF 3 -Ph 2-OMe-4-Cl-Ph tBu 2-039 3-Me-Ph 2-OMe-4-Cl-Ph tBu 2-040 3-Cl-Ph 2-OMe-4-Cl-Ph tBu 2-041 Ph 2-OMe-4-Cl-Ph tBu 2-042 3-CF 3 -Ph 2-OMe-4-Br-Ph tBu 2-043 3-Me-Ph 2-OMe-4-Br-Ph tBu 2-044 3-Cl-Ph 2-OMe-4-Br-Ph tBu 2-045 Ph 2-OMe-4-Br-Ph tBu 2-046 3-CF 3-Ph 3-Cl-5-Br-(E-2a) tBu 57-60 ―――――――――――――――――――――――――――――――― [Table 3]

[0216]

Chem.

[0217] ――――――――――――――――――――――――――――――――― No. G Z R X m.p.(°C) ――――――――――――――――――――――――――――――――― 3-001 3-Me-Ph 4-Cl-Ph tBu 79-81 3-002 3-CF 3 -Ph 4-Cl-Ph tBu * ――――――――――――――――――――――――――――――――― [Table 4]

[0218]

Chem.

[0219] ―――――――――――――――――――――――――――――――― No. G Z R X m.p.(°C) ―――――――――――――――――――――――――――――――― 4-001 3-Me-Ph 4-Cl-Ph tBu * 4-002 3-CF 3 -Ph 4-Cl-Ph tBu * ―――――――――――――――――――――――――――――――― [Table 5]

[0220]

Chem.

[0221] ――――――――――――――――――――――――――――― No. G R X R Y m.p.(℃) ――――――――――――――――――――――――――――― i-001 3-CF 3 -Ph Ph H 177-179 i-002 3-CF 3 -Ph tBu H 120-124 i-003 3-CF 3 -Ph Bn H 124-126 i-004 3-CF 3 -Ph Me H i-005 3-CF 3 -Ph 2-Cl-Ph H i-006 3-CF 3 -Ph 3-Cl-Ph H 177-180 i-007 3-CF 3 -Ph 4-Cl-Ph H i-008 2-F-3-cPr-Ph Ph H i-009 3-Br-Ph tBu H 95-102 i-010 2-F-3-Cl-Ph tBu H 153-155 i-011 Ph tBu H 142-144 i-012 2-CF 3 -Ph tBu H 139-141 i-013 4-CF 3 -Ph tBu H 131-133 i-014 3-F-Ph tBu H 154-156 i-015 2-Cl-Ph tBu H 166-168 i-016 3-Cl-Ph tBu H 122-124 i-017 4-Cl-Ph tBu H 119-121 i-018 2,3-Cl 2-Ph tBu H 160 - 162 i - 019 2,4 - Cl 2 -Ph tBu H 143 - 145 i - 020 3,4 - Cl 2 -Ph tBu H 143 - 145 i - 021 3 - I - Ph tBu H 121 - 123 i - 022 3 - OMe - Ph tBu H 145 - 147 i - 023 3 - OCF 3 -Ph tBu H 112 - 114 i - 024 3 - NMe 2 -Ph tBu H 126 - 130 i - 025 3 - CF 3 -Ph iPr H 177 - 179 i - 026 Ph iPr H 142 - 144 i - 027 Ph Ph H 176 - 178 i - 028 2 - F - 3 - Br - Ph tBu H i - 029 2 - F - 3 - cPr - Ph tBu H i - 030 3 - CF 3 -Ph E - 2a H 115 - 117 i - 031 3 - CF 3 -Ph E - 3a H 191 - 193 i - 032 3 - CF 3 -Ph E - 4a H 166 - 168 i - 033 Ph E - 2a H 121 - 123 i - 034 Ph E - 3a H 187 - 189 i - 035 Ph E - 4a H 153 - 155 i - 036 3 - Me - Ph tBu H 116 - 118 i - 037 3 - SMe - Ph tBu H 117 - 119 ――――――――――――――――――――――――――――― [Table 6]

[0222] [Chemical formula]

[0223] ------------------------------------------------------------------ No.GR X R Y R 101 mp(℃) ------------------------------------------------------------------ ii-001 3-CF 3 -Ph tBu H Me ii-002 2-F-3-Br-Ph tBu H Me ii-003 2-F-3-cPr-Ph tBu H Me ii-004 3-Br-Ph tBu H Me 69-71 ii-005 3-Me-Ph tBu H Me * ------------------------------------------------------------------ Among the compounds of the present invention shown in Tables 1 to 4, those for which the melting point is not recorded are 1 The H-NMR data is shown in Table 7. The following data was measured in deuterated chloroform, with "#1" indicating that the data was measured at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL), and "#2" indicating that the data was measured at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).

[0224] [Table 7] ---------------------------------------------------------------------------------- No. 1 H-NMR (CDCl 3 , Me 4 Si) ---------------------------------------------------------------------------------- 1-001(#1):δ7.46-7.10 (m, 8H), 6.92-6.77 (m, 2H), 5.02-4.91 (m, 1H), 3.89-3.77 (m, 4H), 3.63-3.51 (m, 1H), 3.35-3.12 (m, 1H), 1.73 (s, 9H)。 1-002(#2):δ7.50-7.39 (m, 4H), 7.26-7.18 (m, 3H), 7.08 (s, 1H), 7.05-6.99 (m, 1H), 6.90-6.80 (m, 1H), 5.33 (s, 1H), 4.28-4.19 (m, 1H), 3.95-3.86 (m, 1H), 1.68 (s, 9H)。 1-003(#1):δ7.51-7.23 (m, 7H), 7.18 (s, 1H), 7.17-7.10 (m, 1H), 6.92-6.81 (m, 1H), 4.82-4.76 (m, 1H), 3.84-3.73 (m, 1H), 3.49-3.37 (m, 1H), 3.08-2.69 (m, 1H), 1.72 (s, 9H)。 1-005(#1):δ7.50-7.05 (m, 9H), 6.90-6.77 (m, 1H), 4.80-4.69 (m, 1H), 3.86-3.72 (m, 1H), 3.50-3.37 (m, 1H), 2.60-2.48 (m, 1H), 2.30 (s, 3H), 1.73 (s, 9H)。 1-006(#2):δ7.47-7.33 (m, 2H), 7.31-7.20 (m, 3H), 7.14 (s, 1H), 7.12-7.01 (m, 3H), 6.76-6.64 (m, 1H), 3.84-3.75 (m, 1H), 3.60-3.51 (m, 1H), 2.73-2.65 (m, 1H), 2.27 (s, 3H), 1.68 (s, 9H), 1.49 (s, 3H)。 1-007(#2):δ7.48-7.42 (m, 1H), 7.40-7.35 (m, 1H), 7.32-7.28 (m, 1H), 7.20-7.13 (m, 3H), 6.97-6.90 (m, 2H), 6.81-6.71 (m, 1H), 6.05-5.99 (m, 1H), 3.86-3.77 (m, 1H), 3.63-3.53 (m, 1H), 2.35 (s, 3H), 2.26 (s, 3H), 1.91 (s, 3H), 1.72 (s, 9H)。 1-008(#2):δ7.49-7.43 (m, 1H), 7.42-7.38 (m, 1H), 7.30-7.25 (m, 1H), 7.19-7.12 (m, 3H), 7.00-6.91 (m, 2H), 6.88-6.78 (m, 1H), 6.23-6.17 (m, 1H), 3.97-3.89 (m, 1H), 3.73-3.62 (m, 1H), 2.39 (s, 3H), 2.27 (s, 3H), 1.73 (s, 9H)。 1-009(#2):δ7.36-7.23 (m, 4H), 7.13-6.99 (m, 4H), 6.98-6.83 (m, 3H), 3.84-3.73 (m, 1H), 3.55-3.46 (m, 1H), 3.02-2.87 (m, 1H), 2.28 (s, 3H), 1.68 (s, 9H), 1.47 (s, 3H)。 1-010(#2):δ7.36-7.26 (m, 3H), 7.19-7.16 (m, 1H), 7.13-6.88 (m, 6H), 4.88-4.81 (m, 1H), 3.79-3.70 (m, 1H), 3.32-3.23 (m, 1H), 2.66-2.58 (m, 1H), 2.26 (s, 3H), 2.24 (s, 3H), 1.73 (s, 9H)。 1-011(#2): δ 7.51 - 7.47 (m, 1H), 7.32 - 7.23 (m, 2H), 7.19 (s, 1H), 7.17 - 7.09 (m, 2H), 7.03 - 7.00 (m, 1H), 6.90 - 6.83 (m, 2H), 5.17 - 5.13 (m, 1H), 3.86 - 3.78 (m, 1H), 3.62 - 3.53 (m, 1H), 1.73 (s, 9H). The OH proton was not observed. 1-012(#2): δ 7.37 - 7.29 (m, 1H), 7.25 - 7.15 (m, 2H), 7.13 - 7.02 (m, 1H), 7.01 - 6.88 (m, 3H), 6.88 - 6.79 (m, 2H), 4.93 - 4.86 (m, 1H), 3.81 - 3.72 (m, 1H), 3.36 - 3.27 (m, 1H), 2.71 - 2.58 (m, 1H), 2.33 (s, 3H), 2.28 (s, 3H), 2.27 (s, 3H), 1.75 (s, 9H). 1-013(#2): δ 7.32 - 7.25 (m, 2H), 7.22 - 7.15 (m, 1H), 7.11 (s, 1H), 7.10 - 7.03 (m, 2H), 6.96 - 6.85 (m, 2H), 6.80 - 6.70 (m, 2H), 3.84 - 3.76 (m, 1H), 3.56 - 3.48 (m, 1H), 2.99 - 2.88 (m, 1H), 2.32 (s, 3H), 2.28 (s, 3H), 1.69 (s, 9H), 1.48 (s, 3H). 1-014(#2): δ 7.35 - 7.27 (m, 3H), 7.20 - 7.15 (m, 1H), 7.13 - 6.88 (m, 5H), 4.89 - 4.81 (m, 1H), 3.80 - 3.69 (m, 1H), 3.33 - 3.22 (m, 1H), 2.67 - 2.57 (m, 1H), 2.26 (s, 3H), 2.24 (s, 3H), 1.73 (s, 9H). 1-015(#2):δ7.48-7.29 (m, 4H), 7.26-7.16 (m, 3H), 7.14 (s, 1H), 7.10-7.04 (m, 1H), 6.81-6.68 (m, 1H), 3.79-3.71 (m, 1H), 3.63-3.56 (m, 1H), 3.12-3.03 (m, 1H), 1.67 (s, 9H), 1.49 (s, 3H)。 1-016(#1):δ8.51-8.43 (m, 1H), 7.95-7.84 (m, 1H), 7.78-7.68 (m, 1H), 7.53-7.24 (m, 7H), 7.21-7.09 (m, 1H), 6.98-6.89 (m, 2H), 5.11-5.00 (m, 1H), 3.86-3.74 (m, 1H), 3.42-3.28 (m, 1H), 2.84-2.72 (m, 1H), 2.33-2.22 (m, 6H)。 1-017(#1):δ8.46-8.40 (m, 1H), 7.95-7.86 (m, 1H), 7.77-7.71 (m, 1H), 7.55-7.19 (m, 9H), 7.15-7.08 (m, 1H), 5.30-5.18 (m, 1H), 4.21-3.94 (m, 1H), 3.92-3.79 (m, 1H), 3.66-3.50 (m, 1H)。 1-018(#1):δ8.48-8.42 (m, 1H), 7.93-7.83 (m, 1H), 7.72-7.65 (m, 1H), 7.51-7.15 (m, 8H), 7.08-7.02 (m, 2H), 6.93-6.82 (m, 1H), 4.01-3.85 (m, 1H), 3.59-3.43 (m, 1H), 3.09-2.81 (m, 1H), 2.27 (s, 3H), 1.51 (s, 3H)。 1-019(#2):δ7.47-7.40 (m, 1H), 7.39-7.34 (m, 1H), 7.32-7.28 (m, 1H), 7.26-7.21 (m, 2H), 7.20-7.18 (m, 1H), 7.17-7.13 (m, 1H), 6.90-6.78 (m, 3H), 4.75-4.69 (m, 1H), 3.79-3.71 (m, 4H), 3.47-3.38 (m, 1H), 2.75-2.59 (m, 1H), 1.72 (s, 9H)。 1-020(#2):δ7.37-7.30 (m, 2H), 7.26-7.22 (m, 2H), 7.18-7.16 (m, 1H), 7.14-7.08 (m, 1H), 7.04-6.98 (m, 3H), 6.84-6.78 (m, 2H), 4.74-4.68 (m, 1H), 3.81-3.69 (m, 4H), 3.47-3.37 (m, 1H), 2.76-2.67 (m, 1H), 1.73 (s, 9H)。 1-021(#2):δ7.30-7.15 (m, 4H), 7.08-7.01 (m, 1H), 6.95-6.90 (m, 1H), 6.85-6.79 (m, 4H), 4.76-4.71 (m, 1H), 3.79-3.70 (m, 4H), 3.48-3.40 (m, 1H), 2.82-2.73 (m, 1H), 2.33 (s, 3H), 1.73 (s, 9H)。 1-027(#1):δ7.34-7.27 (m, 1H), 7.21-7.09 (m, 2H), 6.95-6.83 (m, 4H), 6.78-6.67 (m, 2H), 3.93-3.84 (m, 1H), 3.75-3.65 (m, 1H), 2.64 (s, 1H), 2.46 (s, 3H), 2.32 (s, 3H), 2.24 (s, 3H), 1.70 (s, 9H), 1.53 (s, 3H)。 1-028(#1): δ 7.83-7.76 (m, 1H), 7.25-6.91 (m, 5H), 6.88-6.77 (m, 1H), 6.74-6.64 (m, 2H), 4.15-4.05 (m, 1H), 4.02-3.91 (m, 1H), 2.34 (s, 3H), 1.73 (s, 3H), 1.64 (s, 9H). No OH protons were observed. 1-029(#2):δ7.48-7.32 (m, 4H), 7.30-7.22 (m, 3H), 7.14 (s, 1H), 7.11-7.02 (m, 1H), 6.76-6.65 (m, 1H), 3.81-3.70 (m, 1H), 3.64-3.52 (m, 1H), 2.92 (s, 1H), 1.68 (s, 9H), 1.48 (s, 3H). 1-030(#2): δ 7.46-7.31 (m, 2H), 7.30-7.24 (m, 1H), 7.24-7.19 (m, 1H), 7.15 (s, 1H), 7.11-7.01 (m, 1H), 6.93-6.81 (m, 2H), 6.78-6.66 (m, 1H), 3.91-3.81 (m, 1H), 3.78-3.68 (m, 1H), 2.45 (s, 3H), 2.23 (s, 3H), 1.69 (s, 9H), 1.53 (s, 3H). No OH protons were observed. 1-031(#2): δ 7.80-7.73 (m, 1H), 7.49-7.31 (m, 3H), 7.23-7.19 (m, 1H), 7.12-7.04 (m, 2H), 7.04-6.97 (m, 1H), 6.93-6.82 (m, 1H), 4.20-4.07 (m, 1H), 3.99-3.87 (m, 1H), 1.75 (s, 3H), 1.64 (s, 9H). No OH protons were observed. 2-001(#1):δ7.43-7.14 (m, 5H), 7.13-7.08 (m, 1H), 7.08-7.01 (m, 1H), 6.94-6.72 (m, 3H), 3.83 (s, 3H), 3.42 (d, J = 4.8 Hz, 2H), 1.66 (s, 9H), 0.79-0.73 (m, 4H)。 2-002(#1):δ7.36-7.02 (m, 6H), 7.01-6.69 (m, 5H), 3.83 (s, 3H), 3.43 (d, J = 5.1 Hz, 2H), 1.66 (s, 9H), 0.82-0.68 (m, 4H)。 2-003(#2):δ7.51-7.36 (m, 2H), 7.33-7.26 (m, 1H), 7.25-7.22 (m, 1H), 7.16 (s, 1H), 7.14-7.10 (m, 2H), 7.00-6.93 (m, 1H), 6.52-6.42 (m, 1H), 3.61-3.53 (m, 2H), 1.67 (s, 9H), 1.00-0.92 (m, 2H), 0.91-0.77 (m, 2H)。 2-004(#2):δ7.45-7.33 (m, 2H), 7.20-7.16 (m, 1H), 7.15 (s, 1H), 7.09-6.95 (m, 5H), 6.51-6.42 (m, 1H), 3.52 (d, J = 5.5 Hz, 2H), 2.26 (s, 3H), 1.69 (s, 9H), 0.82-0.78 (m, 4H)。 2-005(#2):δ7.22-7.15 (m, 1H), 7.13 (s, 1H), 7.11-7.06 (m, 2H), 7.00-6.94 (m, 2H), 6.94-6.89 (m, 1H), 6.75-6.64 (m, 3H), 3.52 (d, J = 5.5 Hz, 2H), 2.32 (s, 3H), 2.27 (s, 3H), 1.69 (s, 9H), 0.83-0.75 (m, 4H)。 2-006(#2):δ7.35-7.27 (m, 2H), 7.16-7.05 (m, 4H), 7.01-6.88 (m, 4H), 6.72-6.58 (m, 1H), 3.51 (d, J = 5.5 Hz, 2H), 2.26 (s, 3H), 1.69 (s, 9H), 0.81-0.76 (m, 4H)。 2-007(#2):δ7.46-7.34 (m, 2H), 7.30-7.22 (m, 2H), 7.21-7.14 (m, 2H), 7.07-6.98 (m, 3H), 6.45 (br, 1H), 3.54 (d, J = 5.6 Hz, 2H), 1.69 (s, 9H), 0.90-0.78 (m, 4H)。 2-008(#2):δ7.36-7.30 (m, 2H), 7.25-7.21 (m, 2H), 7.15-7.10 (m, 2H), 7.07-7.02 (m, 2H), 6.94-6.88 (m, 2H), 6.66 (br, 1H), 3.52 (d, J = 5.2 Hz, 2H), 1.69 (s, 9H) 0.88-0.76 (m, 4H)。 2-009(#1):δ7.40-7.34 (m, 2H), 7.20-7.12 (m, 7H), 7.05-7.00 (m, 1H), 6.97-6.45 (br, 1H), 3.55 (d, J = 5.4 Hz, 2H), 1.69 (s, 9H) 0.85-0.82 (m, 4H)。 2-010(#1):δ7.34-7.26 (m, 2H), 7.22-7.05 (m, 7H), 6.94-6.87 (m, 2H), 6.64 (br, 1H), 3.54 (d, J = 5.4 Hz, 2H), 1.69 (s, 9H) 0.85-0.79 (m, 4H)。 2-012(#2):δ7.28-7.16 (m, 4H), 7.07-7.01 (m, 2H), 6.97-6.90 (m, 1H), 6.75-6.66 (m, 3H), 3.53 (d, J = 5.6 Hz, 2H), 2.34 (s, 3H), 1.70 (s, 9H), 0.89-0.75 (m, 4H)。 2-014(#1):δ7.22-7.07 (m, 4H), 6.95-6.87 (m, 1H), 6.77-6.62 (m, 5H), 3.72 (s, 3H), 3.49 (d, J = 5.4 Hz, 2H), 2.33 (s, 3H), 1.69 (s, 9H), 0.85-0.71 (m, 4H)。 2-015(#1):δ7.45-7.31 (m, 2H), 7.23-7.17 (m, 1H), 7.15 (s, 1H), 7.13-7.02 (m, 3H), 6.73-6.65 (m, 2H), 6.50-6.36 (m, 1H), 3.73 (s, 3H), 3.50 (d, J = 5.4 Hz, 2H), 1.69 (s, 9H), 0.82-0.73 (m, 4H)。 2-016(#1):δ7.30-7.28 (m, 1H), 7.26-7.18 (m, 1H), 7.11 (s, 1H), 7.01-6.92 (m, 2H), 6.84-6.74 (m, 3H), 6.72-6.61 (m, 1H), 3.55 (d, J = 5.7 Hz, 2H), 2.35 (s, 3H), 1.68 (s, 9H), 1.02-0.91 (m, 2H), 0.83-0.75 (m, 2H)。 2-017(#1):δ7.52-7.35 (m, 2H), 7.31-7.24 (m, 2H), 7.14 (s, 1H), 7.14-7.08 (m, 1H), 7.04-6.98 (m, 1H), 6.93-6.85 (m, 1H), 6.51-6.36 (m, 1H), 3.55 (d, J = 6.0 Hz, 2H), 1.67 (s, 9H), 1.00-0.91 (m, 2H), 0.83-0.76 (m, 2H)。 2-019(#1):δ8.30 (d, J = 2.4 Hz, 1H), 7.89-7.81 (m, 1H), 7.31-7.22 (m, 6H), 7.11-7.23 (m, 2H), 7.01-6.95 (m, 1H), 6.95-6.88 (m, 2H), 6.73 (br, 1H), 3.59 (d, J = 5.7 Hz, 2H), 1.69 (s, 9H) 0.94-0.83 (m, 4H)。 2-020(#1):δ7.22-7.09 (m, 2H), 6.95-6.87 (m, 1H), 6.83-6.66 (m, 5H), 6.62-6.54 (m, 1H), 3.80 (s, 3H), 3.79 (s, 3H), 3.51 (d, J = 5.4 Hz, 2H), 2.32 (s, 3H), 1.70 (s, 9H), 0.89-0.70 (m, 4H)。 2-021(#1):δ7.45-7.30 (m, 2H), 7.23-7.18 (m, 1H), 7.16 (s, 1H), 7.07-6.99 (m, 1H), 6.81-6.75 (m, 1H), 6.72-6.65 (m, 1H), 6.64-6.56 (m, 1H), 6.51-6.40 (m, 1H), 3.82 (s, 3H), 3.80 (s, 3H), 3.51 (d, J = 5.4 Hz, 2H), 1.69 (s, 9H), 0.84-0.73 (m, 4H)。 3-002(#1):δ7.48-7.34 (m, 2H), 7.20-7.09 (m, 4H), 7.06-6.99 (m, 1H), 6.98-6.90 (m, 2H), 6.21-6.08 (m, 1H), 3.72 (d, J = 5.8 Hz, 2H), 2.30-2.06 (m, 5H), 1.96-1.78 (m, 1H), 1.69 (s, 9H)。 4-001(#1):δ7.24-7.16 (m, 1H), 7.11-7.08 (m, 4H), 7.06 (s, 1H), 6.97-6.91 (m, 1H), 6.72-6.65 (m, 2H), 6.43-6.32 (m, 1H), 3.52 (d, J = 6.1 Hz, 2H), 2.35 (s, 3H), 1.96-1.51 (m, 17H). 4-002(#2):δ7.49-7.34 (m, 2H), 7.20-7.06 (m, 6H), 7.05-6.96 (m, 1H), 6.17-6.02 (m, 1H), 3.53 (d, J = 5.8 Hz, 2H), 1.93-1.48 (m, 17H). ---------------------------------------------------------------------------------- [Test example] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically explained in the following test examples, but the present invention is not limited to these. In the test examples, "RH" stands for relative humidity, and for example, "humidity 100% RH" means that the relative humidity is 100%.

[0225] Preparation of test drug solutions The compound of the present invention was dissolved in an emulsion 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 Corp.) [1:5:28 (weight ratio)] to prepare emulsions with concentrations of 1 mass %, 5 mass %, or 20 mass %. These emulsions were used as test chemical solutions in the following Test Examples 1 to 7.

[0226] Test Example 1: Wheat blight control effect test 90cm 3Wheat (variety: Haruyutaka) was planted in plastic pots and, at the 1.3-leaf stage, 5 ml of the test solution, which had been diluted with water to 500 ppm, was sprayed onto the pots. One day after spraying, the wheat was inoculated by spraying a suspension of conidia of the wheat leaf spot fungus (Septoria nodorum), and placed in an inoculation box at a temperature of 20°C and a humidity of 100% for two days. The pots were then kept in an air-conditioned greenhouse (temperature 20°C, humidity 80% for eight days). The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated according to the following formula.

[0227] Control value = [1-(lesion area rate in treated area / lesion area rate in untreated area)] x 100 As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0228] Compounds; No. 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-011, 1-013, 1-014, 1-015, 1-019, 1-022, 1-023, 1-026, 1-027, 1-028, 1-029, 1-030, 1-031, 2-001, 2-003, 2-004, 2-005, 2-006, 2-007, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-046, 3-001, 3-002, 4-001.

[0229] Test Example 2: Tomato powdery mildew control effect test 90cm 3 Tomatoes (variety: Momotaro) were planted in plastic pots, and at the 2-leaf stage, 5 ml of the test solution, which had been diluted with water to 500 ppm, was sprayed on the plants. After air drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated with a suspension of conidia of tomato powdery mildew (Leveillula taurica) by spraying. After leaving the plants for 14 days, the proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0230] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0231] Compound No. 1-001, 1-002, 1-003, 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, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028 , 1-029, 1-030, 1-031, 2-001, 2-002, 2-003, 2-004, 2-005, 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, 2-046, 3-001, 3-002, 4-001, 4-002.

[0232] Test Example 3: Cucumber gray mold control effect test 90cm 3 A cucumber (variety: Sagami Hanshiro) was planted in a plastic pot, and at the cotyledon stage, 5 ml of the test solution, which was diluted with water to 500 ppm, was sprayed and air-dried. The treated leaves were then cut off and placed in a plastic container. A conidial suspension of cucumber gray mold fungus (Botrytis cinerea) and dissolved PDA medium were mixed in a 1:1 (volume ratio) ratio, and 30 μl of the mixture was dropped onto the treated leaves for inoculation. After inoculation, the plants were left at 20°C and in a humid environment (100% RH) for 3 days. The proportion of the formed lesions on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0233] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0234] Compound No. 1-001, 1-002, 1-003, 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, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028 , 1-029, 1-030, 1-031, 2-001, 2-002, 2-003, 2-004, 2-005, 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, 2-046, 3-001, 3-002, 4-001, 4-002.

[0235] Test Example 4: Cucumber stem rot control effect test 90cm 3 A cucumber (variety: Sagami Hanshiro) was planted in a plastic pot, and at the cotyledon stage, 5 ml of a test solution prepared by diluting the solution with water to 500 ppm was sprayed and air-dried. The treated leaves were then placed in a plastic container. A piece of agar (diameter 5 mm) containing cucumber sclerotinia sclerotiorum, which had been cultured in advance on PDA medium, was inoculated onto the cotyledons of the drug-treated cucumber. After inoculation, the plastic container was covered with vinyl, humidified (humidity 100% RH), and left at 20°C for 2 days. The proportion of the formed lesions on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0236] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0237] Compound No. 1-001, 1-002, 1-003, 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, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1- 027, 1-028, 1-029, 1-030, 1-031, 2-001, 2-002, 2-003, 2-004, 2-005, 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, 2-046, 4-001.

[0238] Test Example 5: Cucumber powdery mildew control effect test 90cm 3 Cucumbers (variety: Sagami Hanshiro) were planted in plastic pots, and at the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed on the plants. After air drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated with a conidiospore suspension of cucumber powdery mildew fungus (Erysiphe polygoni) by spraying. After leaving the plants for 9 days, the proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0239] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0240] Compound No. 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-011, 1-012, 1-013, 1-014, 1-015, 1-019, 1-022, 1-023, 1-024, 1-026, 1-027, 1-029, 1-030, 1-031, 2-001, 2- 002, 2-003, 2-004, 2-005, 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, 2-046, 3-001, 3-002, 4-002.

[0241] Test Example 6: Cucumber anthracnose control effect test 90cm 3 Cucumbers (variety: Sagami Hanshiro) were planted in plastic pots, and at the cotyledon stage, 5 ml of the test solution, which had been diluted with water to 500 ppm, was sprayed. One day after spraying, the cucumbers were inoculated by spraying with a conidial suspension of cucumber anthracnose fungus (Colletotrichum lagenarium), and placed in an inoculation box at a temperature of 25°C and a humidity of 100% for two days. Thereafter, the cucumbers were placed in an air-conditioned greenhouse (temperature 23°C, humidity 60% for seven days). The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0242] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0243] Compound No. 1-001, 1-002, 1-003, 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, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1- 028, 1-029, 1-030, 1-031, 2-001, 2-002, 2-003, 2-004, 2-005, 2-006, 2-007, 2-008, 2-009, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-046, 3-001, 3-002, 4-001, 4-002.

[0244] Test Example 7: Soybean rust disease control effect test 90cm 3 Soybeans (variety: Enrei) were planted in plastic pots, and at the single leaf stage, 5 ml of the test solution, which had been diluted with water to 500 ppm, was sprayed. One day after spraying, the soybeans were inoculated by spraying a suspension of conidia of soybean rust fungus (Phakopsora pachyrhizi), and placed in an inoculation box at a temperature of 20°C and a humidity of 100% for two days. Thereafter, the soybeans were placed in an air-conditioned greenhouse (temperature 20°C, humidity 60% for 10 days). The proportion of the formed lesions on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0245] As a result, among the compounds tested, the following compounds showed a control value of 70% or more.

[0246] Compounds: Nos. 1-004, 1-005, 1-010, 1-012, 1-018, 1-023, 2-003, 2-008, 2-020, 2-021, 2-046. [Industrial Applicability]

[0247] The pyrazole compounds according to the present invention are extremely useful compounds which exhibit excellent pest control activity, particularly fungicidal activity, and have almost no adverse effects on non-target organisms such as mammals, fish and useful insects.

Claims

1. Formula (1): 【Chemistry 1】 [In the formula, G represents G-1, G-1 represents a structure represented by the following structural formula: 【Chemistry 2】 G １ is a hydroxyl, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl, di(C １ ~C ６ -C(=NOR)R', G １ In the above relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R ｂ Cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ -C(=NOR)R', R is a hydrogen atom or C １ ~C ６ represents an alkyl group, R' is C １ ~C ６ represents an alkyl group, T represents an oxygen atom or a sulfur atom; R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1, R Ｘ -2, R Ｘ -3 or R Ｘ represents −4, R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula, 【Chemistry 3】 X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, X １ In the above relationship, when u5 is an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, X １ In the above relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R ｃ Cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ -C(=NOR)R', R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents an alkyl group, R １ is a hydrogen atom or C １ ~C ６ represents an alkyl group, R ２ is a hydrogen atom or C １ ~C ６ represents an alkyl group, R ３ is a hydrogen atom or C １ ~C ６ represents an alkyl group, R ４ is -OR ａ represents R ５ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, Or, R ４ and R ５ Together, C ２ ~C ５ By forming an alkylene chain, R ４ and R ５ represents that the ring is formed of 3 to 6 members together with the carbon atom to which it is attached. R ａ is a hydrogen atom, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ represents haloalkylcarbonyl; Z represents Z-1 to Z-7 or Z-8; Z-1 to Z-8 each represent a structure represented by the following structural formula: 【Chemistry 4】 In addition, Z １ represents a substitution position on the aromatic ring of Z-1 to Z-8, Z １ is a hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylamino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R ｉ C substituted with １ ~C ６ Alkyl, -OR ｄ , -NHC(O)R ｅ , -NR ｈ C(O)R ｅ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ N.H. ２ , —C(═NOR)R′ , E-1 to E-54, F-1 to F-14 or F-15; Z １ In the above relationship, when n7 is an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, Z １ In the above relationship, when n5 is an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, Z １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, Z １ In the case where n3 is an integer of 2 or 3, each Z １ may be the same as or different from each other, R ｄ is C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Haloalkyl, R １０ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-54, F-1 to F-14 or F-15; R １０ is C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C １ ~C ６ -alkyl)aminocarbonyl, -C(=NOR)R', E-1 to E-54, F-1 to F-14 or F-15; R ｅ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, benzyloxy, E-1 to E-54, F-1 to F-14 or F-15; R ｆ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, di(C １ ~C ６ alkyl)amino, E-1 to E-54, F-1 to F-14 or F-15; R ｇ is a hydrogen atom or a tri(C １ ~C ４ represents an alkyl)silyl; R ｈ is C １ ~C ６ represents an alkyl group, R ｉ is hydroxy or C １ ~C ６ represents alkoxy, E-1 to E-54 each represent a structure represented by the following structural formula: 【Chemistry 5】 【Chemistry 6】 F-1 to F-15 each represent a structure represented by the following structural formula: 【Chemistry 7】 Z ａ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ represents an alkoxycarbonyl; Z ａ In the relationship, 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, Z ａ In the relationship, 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, Z ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same as or different from each other, Z ａ In the relationship, when v4 represents an integer of 2, 3 or 4, each Z ａ may be the same as or different from each other, Z ａ In the relationship, when v3 represents an integer of 2 or 3, each Z ａ may be the same as or different from each other, Z ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, Z ｂ is C １ ~C ６ represents an alkyl group, m5 represents an integer of 0, 1, 2, 3, 4 or 5; n7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; n5 represents an integer of 0, 1, 2, 3, 4 or 5; n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2 or 3; u5 represents an integer of 0, 1, 2, 3, 4 or 5; u4 represents an integer of 0, 1, 2, 3 or 4; v7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7; v6 represents an integer of 0, 1, 2, 3, 4, 5, or 6; v5 represents an integer of 0, 1, 2, 3, 4 or 5; v4 represents an integer of 0, 1, 2, 3 or 4; v3 represents an integer of 0, 1, 2 or 3; v2 represents an integer of 0, 1 or 2; v1 represents an integer of 0 or 1. A pyrazole compound represented by the following formula (1):

2. G １ is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, T represents an oxygen atom; R Ｘ is C １ ~C ６ Alkyl or R Ｘ represents −2, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, R ２ represents a hydrogen atom, R ３ represents a hydrogen atom, Z represents Z-1 or Z-8; Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or E-3, Z ａ represents a halogen atom, m5 represents an integer of 0 or 1; n5 represents an integer of 0, 1 or 2; n4 represents an integer of 2; u4 represents an integer of 0; The pyrazole compound or a salt thereof according to claim 1 , wherein v4 represents an integer of 1.

3. 3. An agricultural chemical comprising at least one selected from the pyrazole compounds and salts thereof according to claim 1 or 2 as an active ingredient.

4. A fungicide comprising at least one selected from the pyrazole compounds and salts thereof according to claim 1 or 2 as an active ingredient.

5. 3. An agricultural and horticultural fungicide comprising at least one selected from the pyrazole compounds and salts thereof according to claim 1 or 2 as an active ingredient.

6. An antifungal agent comprising at least one selected from the pyrazole compounds and salts thereof according to claim 1 or 2 as an active ingredient.

7. An internal parasite control agent comprising at least one selected from the pyrazole compounds and salts thereof according to claim 1 or 2 as an active ingredient.

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