Pyrazole compounds and pest control agents

Abstract

Providing a novel agent having an excellent control effect. 【Solution means】Provided are a pyrazole compound represented by formula (1) or a salt thereof, and a novel fungicide containing the same as an active ingredient, particularly a fungicide for agricultural and horticultural use. In the formula, G represents G-1, and G 1 represents C1-C6 alkyl or the like, and R X represents C1-C6 alkyl or the like, and R Y represents a hydrogen atom or the like, and R 2 represents a hydrogen atom or the like, and R 3 represents a hydrogen atom or the like, Z 1 represents E-1 or the like, Z a represents C1-C6 alkyl or the like, Z 2 represents C1-C6 alkyl or the like, m5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, and v2 represents an integer of 0, 1 or 2. JPEG2026069209000025.jpg24104

Description

[Technical Field]

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

[0002] Patent documents 1 to 3 disclose certain pyrazole compounds, but they do not disclose anything regarding the pyrazole compound according to the present invention.

[0003] Furthermore, while Patent Documents 4 to 8 disclose that certain pyrazole compounds are useful as bactericides, they do not disclose anything about the pyrazole compound according to the present invention. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] International Publication No. 2002 / 085860 [Patent Document 2] International Publication No. 2006 / 132197 [Patent Document 3] European Patent Application Publication No. 289879 [Patent Document 4] International Publication No. 2009 / 028280 [Patent Document 5] International Publication No. 1996 / 038419 [Patent Document 6] International Publication No. 2023 / 243678 [Patent Document 7] International Publication No. 2024 / 162284 [Patent Document 8] International Publication No. 2024 / 204842 [Overview of the Initiative] [Problems that the invention aims to solve]

[0005] However, prolonged use of pesticides can lead to the development of drug resistance in pathogenic bacteria. Therefore, the development of new pesticides with superior control efficacy is always highly anticipated. [Means for solving the problem]

[0006] The present inventors conducted extensive research with the goal of solving the above-mentioned problems, and as a result, discovered that a novel pyrazole compound represented by the following formula (1) according to the present invention exhibits excellent pest control activity as a fungicide, particularly as a fungicide for agriculture and horticulture, thus completing the present invention.

[0007] The pyrazole compounds according to the present invention have not been disclosed in any literature, and their usefulness as pest control agents is unknown.

[0008] In other words, the present invention relates to the following [1].

[0009] [1] Formula (1):

[0010] [ka]

[0011] [In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula:

[0012] [ka]

[0013] G 1 These are hydroxy, nitro, cyano, halogen atoms, C1-C6 alkyl, and C3-C 10Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 represents cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, G 1 in the relationship with, 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 X is C1-C6 alkyl, C3-C 10 cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1, R X -2, R X -3 or R X -4, R X -1 to R X -4 each represent a structure represented by the following structural formula,

[0014]

Chemical formula

[0015] X 1 represents a halogen atom, C1-C6 alkyl, C1-C6 haloalkyl or C1-C6 alkoxy, X 1 in the relationship with, when u5 represents 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 with, when u4 represents an integer of 2, 3 or 4, each X 1 may be the same as or different from each other, R Y represents a hydrogen atom or a halogen atom, R 2This represents a hydrogen atom or a C1-C6 alkyl group. R 3 This represents a hydrogen atom or a C1-C6 alkyl group. Z 1 This represents E-1 to E-8 or E-9, Z 2 These are hydroxy, carboxy, amino, nitro, cyano, halogen atoms, C1-C6 alkyl, and C3-C 10 This represents a cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 alkylthio. Z 2 In relation to this, if n4 represents an integer of 2, 3, or 4, then each Z 2 They may be the same as each other, or they may be different from each other. E-1 to E-10 represent structures represented by the following structural formulas,

[0016] [ka]

[0017] Z a These are halogen atoms, C1-C6 alkyl, C3-C 10 This represents a cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 alkylthio. Z a In relation to this, if v3 represents an integer of 2 or 3, then each Z a They may be the same as each other, or they may be different from each other. Z a In relation to this, if v2 represents an integer of 2, then each Z a They may be the same as each other, or they may be different from each other. Z b This represents C1-C6 alkyl, m5 represents an integer of 0, 1, 2, 3, 4, or 5. n4 represents an integer of 0, 1, 2, 3, or 4. u5 represents an integer of 0, 1, 2, 3, 4, or 5. u4 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 either 0 or 1. A pyrazole compound represented by or a salt thereof. [Effects of the Invention]

[0018] The compound of the present invention, represented by formula (1), exhibits excellent control activity against many pathogenic bacteria.

[0019] Therefore, the present invention can provide useful fungicides, particularly fungicides for agricultural and horticultural use. [Modes for carrying out the invention]

[0020] The present invention will be described in detail below.

[0021] The compounds of the present invention, or the compounds shown in the production examples or reaction formulas, may have geometric isomers of E- and Z-forms depending on the type of substituent. However, the compounds of the present invention include mixtures containing these E-forms, Z-forms, or E- and Z-forms in any proportion.

[0022] Furthermore, while the compounds of the present invention may contain optically active forms due to the presence of one or more chiral carbon atoms or chiral sulfur atoms, the compounds of the present invention encompass all optically active forms or racemic mixtures.

[0023] Furthermore, while the compounds of the present invention may have tautomers depending on the type of substituent, the compounds of the present invention encompass all tautomers or mixtures of tautomers containing them in any proportion.

[0024] Furthermore, while the compounds of the present invention may exist as one or more rotational isomers due to limited bond rotation caused by steric hindrance between substituents, the compounds of the present invention encompass all rotational isomers or mixtures of diastereomers containing them in any proportion.

[0025] Next, specific examples of each substituent shown in this specification are given below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.

[0026] In this specification, "halogen atoms" include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. The term "halo" in this specification also refers to these halogen atoms.

[0027] In this specification, "C a ~C b The notation "alkyl" represents a linear or branched saturated hydrocarbon group consisting of a to b carbon atoms. a ~C b Examples of alkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl. a ~C b The "alkyl" is selected within a specified range of carbon atoms.

[0028] In this specification, "C a ~C b The notation "haloalkyl" represents a linear or branched saturated hydrocarbon group consisting of a to b carbon atoms, in which hydrogen atoms bonded to carbon atoms are arbitrarily substituted by halogen atoms. When substituted by two or more halogen atoms, these halogen atoms may be identical or distinct from each other. a ~C bExamples of "haloalkyl" 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. a ~C b "Haloalkyl" is selected within a specified range of carbon atoms.

[0029] In this specification, "C a ~C b The notation "alkoxy" represents alkyl-O-, which has a to b carbon atoms as described above. a ~C b Examples of "alkoxy" include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, and 2-ethylhexyloxy. a ~C b The "alkoxy" is selected within a specified range of carbon atoms.

[0030] In this specification, "C a ~C b The notation "haloalkoxy" represents a haloalkyl-O- which has a number of carbon atoms from a to b. a ~C b Examples of "haloalkoxys" 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. a ~C b The "haloalkoxy" is selected within a specified range of carbon atoms.

[0031] In this specification, "C a ~C b The notation "alkylthio" represents alkyl-S-, which means a to b carbon atoms. a ~C b Examples of alkylthio include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio. a ~C b "Alkylthio" is selected within a specified range of carbon atoms.

[0032] In this specification, "C a ~C b The notation "alkylsulfinyl" represents alkyl-S(O)-, which has a to b carbon atoms. a ~C b Examples of alkyl sulfinyl compounds include methyl sulfinyl, ethyl sulfinyl, n-propyl sulfinyl, i-propyl sulfinyl, n-butyl sulfinyl, i-butyl sulfinyl, S-butyl sulfinyl, and tert-butyl sulfinyl. a ~C b The "alkyl sulfinyl" is selected within a specified range of carbon atoms.

[0033] In this specification, "C a ~C b The notation "alkylsulfonyl" represents alkyl-SO2-, which has a to b carbon atoms. a ~C b Examples of alkylsulfonyl compounds include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl. a ~C b The "alkylsulfonyl" is selected within a specified range of carbon atoms.

[0034] As used herein, the notation "C a ~C b cycloalkyl" represents a cyclic hydrocarbon group having a to b carbon atoms. "C a ~C b cycloalkyl" can form, for example, a monocyclic or polycyclic structure from a 3-membered ring to a 10-membered ring. Further, the hydrogen in each ring may be optionally substituted by alkyl within the specified range of the number of carbon atoms. "C a ~C b cycloalkyl" includes, for example, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl as specific examples. "C a ~C b cycloalkyl" is selected within the specified range of the number of carbon atoms.

[0035] As used herein, the notation "di(C a ~C b alkyl)amino" represents an amino group in which both hydrogen atoms are substituted by alkyl as defined above having a to b carbon atoms, which may be the same or different from each other. "di(C a ~C b alkyl)amino" includes, for example, dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, and di(n-butyl)amino as specific examples. Each alkyl of "di(C a ~C b alkyl)amino" is selected within the specified range of the number of carbon atoms.

[0036] As used herein, the notation "C a ~C b alkylcarbonyl" represents alkyl-C(O)- having a to b carbon atoms as defined above. "C a ~C bExamples of "alkylcarbonyl" include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, heptanoyl, and the like. "C a ~C b "alkylcarbonyl" is selected within the specified range of the number of carbon atoms.

[0037] In this specification, the notation "C a ~C b "alkoxycarbonyl" represents alkyl-O-C(O)- having the above-mentioned meaning with a carbon atom number of a to b. "C a ~C b Examples of "alkoxycarbonyl" include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, 2-ethylhexyloxycarbonyl, and the like. "C a ~C b "alkoxycarbonyl" is selected within the specified range of the number of carbon atoms.

[0038] In this specification, the notation "C a ~C b "alkylaminocarbonyl" represents carbamoyl in which one of the hydrogen atoms is substituted by alkyl having the above-mentioned meaning with a carbon atom number of a to b. "C a ~C b Examples of "alkylaminocarbonyl" include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, tert-butylcarbamoyl, and the like. "C a ~C b "alkylaminocarbonyl" is selected within the specified range of the number of carbon atoms.

[0039] In this specification, the notation "C a ~C bThe notation "cycloalkylaminocarbonyl" represents a carbamoyl in which one of the hydrogen atoms is replaced by a cycloalkyl group having a to b carbon atoms. a ~C b Examples of "cycloalkylaminocarbonyl" include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl. a ~C b The "cycloalkylaminocarbonyl" is selected within a specified range of carbon atoms.

[0040] In this specification, "The (C a ~C b The notation "alkylaminocarbonyl" represents a carbamoyl in which both hydrogen atoms are replaced by alkyl atoms in the sense described above, with a to b carbon atoms, where each hydrogen atom may be the same or different from the others. a ~C b Specific examples of "alkylaminocarbonyl" include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl. a ~C b Each alkyl group in "alkylaminocarbonyl" is selected within a specified range of carbon atoms.

[0041] In this specification, the term "benzyl" refers to -CH2C6H5.

[0042] 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 description 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 referred to as "compound (1)," and "the compound represented by formula (2)" will also be referred to as "compound (2)." Other compounds will be described similarly in accordance with this.

[0043] (Manufacturing Example 1) Compound (1) of the present invention can be produced, for example, by the following manufacturing method.

[0044] [ka]

[0045] [In the formula, J 1 G represents a chlorine atom, a bromine atom, a C1-C4 alkylcarbonyloxy, or a C1-C4 alkoxycarbonyloxy, and R represents a chlorine atom, a bromine atom, a C1-C4 alkylcarbonyloxy, or a C1-C4 alkoxycarbonyloxy. X , R Y , R 2 , R 3 , Z 1 , Z 2 And n4 has the same meaning as above. Compound (1) can be produced by reacting compound (3) and compound (4) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) with a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of a base and / or an additive.

[0046] Alternatively, compound (1) can be produced by reacting compound (3-1) with compound (4) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and possibly in the presence of a base and / or additives.

[0047] The amount of compound (4) or its salt used may be 0.5 to 50 equivalents per equivalent of compound (3) or compound (3-1).

[0048] Examples of dehydration condensation agents that can be used in this reaction include 1H-benzotriazole-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-oxidehexafluorophosphate, and 2-chloro-4,6-dimethoxy-1,3,5-triazine. The amount of dehydration condensation agent used may be 0.5 to 50 equivalents per equivalent of compound (3).

[0049] When a solvent is used, the solvent used only needs to be inert to the reaction. Examples of such solvents include water; alcoholic solvents such as methanol, ethanol, or tert-butyl alcohol; etheric solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, or diglym; aromatic hydrocarbon solvents such as benzene, xylene, or toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, or cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, or 1,2-dichloroethane; nitrile solvents such as acetonitrile or propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or N,N'-dimethylimidazolidinone; dimethyl sulfoxide; pyridine; or mixed solvents thereof.

[0050] Examples of bases that can be used in this reaction include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N,N-diethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), or 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, or potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, or potassium tert-butoxide. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3) or compound (3-1).

[0051] Examples of additives that can be used in this reaction include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, and 4-(dimethylamino)pyridine. The amount of additive used may be 0.005 to 100 equivalents per equivalent of compound (3) or compound (3-1).

[0052] The reaction temperature can be set to any temperature from -78°C to the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reaction substrate or the reaction temperature, but can usually be set to any temperature within the range of 5 minutes to 100 hours.

[0053] (Manufacturing example 2) Compound (1) of the present invention can be produced, for example, by the following manufacturing method.

[0054] [ka]

[0055] [In the formula, L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a C1-C4 alkyl sulfonyloxy (e.g., methanesulfonyloxy), a halosulfonyloxy (e.g., fluorosulfonyloxy), a C1-C4 haloalkylsulfonyloxy (e.g., trifluoromethanesulfonyloxy), or an arylsulfonyloxy (e.g., p-toluenesulfonyloxy), and G, R X , R Y , R 2 , R 3 , Z 1 , Z 2 n4 and p have the same meaning as above. Compound (1) can be produced by reacting compound (3-2) and compound (A) in a solvent or without a solvent, and possibly in the presence of a base and / or an additive.

[0056] The amount of compound (A) used may be 0.5 to 50 equivalents per equivalent of compound (3-2).

[0057] Some of the compounds represented by compound (A) are known compounds and are available commercially. Furthermore, the other compounds represented by compound (A) can also be manufactured according to the general synthesis methods of known compounds described in the literature.

[0058] When a solvent is used, the solvent used only needs to be inert to the reaction, and examples of such solvents include those exemplified in Production Example 1.

[0059] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-2).

[0060] Examples of additives that can be used in this reaction include sodium iodide and potassium iodide. The amount of additive used may be 0.005 to 100 equivalents per equivalent of compound (3-2).

[0061] The reaction temperature and reaction time can be arbitrarily set within the temperature and time ranges described in Manufacturing Example 1.

[0062] The compound (3-1) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in Reaction Equation 1 below.

[0063] [Reaction Equation 1]

[0064] [ka]

[0065] [J 1 , G, R X and R Y This expresses the same meaning as above. Compound (3-1) can be obtained by reacting compound (3) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride, in accordance with known methods described in the literature, for example, the method described in the Journal of Medicinal Chemistry [J.Med.Chem.] 1991, Vol. 34, p. 1630, etc.

[0066] Alternatively, it can be obtained by reacting it with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, in the presence of a base if necessary, in accordance with the methods described in Tetrahedron Lett. 2003, Vol. 44, p. 4819, Journal of Medicinal Chemistry 1991, Vol. 34, p. 222, etc.

[0067] The compound (3-2) used in production example 2 can be produced, for example, according to the production route shown in reaction equation 2 below.

[0068] [Reaction Equation 2]

[0069] [ka]

[0070] [J 1 , G, R X , and R Y This expresses the same meaning as above. Compound (3-2) can be produced by reacting compound (3) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) and a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of a base and / or an additive.

[0071] Alternatively, compound (3-2) can be produced by reacting compound (3-1) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and possibly in the presence of a base and / or an additive.

[0072] The amount of hydroxylamine or its salt used may be 0.5 to 50 equivalents per equivalent of compound (3) or compound (3-1).

[0073] Examples of dehydrating condensing agents that can be used in this reaction include the dehydrating condensing agents exemplified in Production Example 1. The amount of dehydrating condensing agent used may be 0.1 to 100 equivalents per equivalent of compound (3).

[0074] When a solvent is used, it is sufficient that the solvent used is inert to the reaction; for example, the solvent exemplified in Production Example 1 is an example of such a solvent.

[0075] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3) or compound (3-1).

[0076] Examples of additives that can be used in this reaction include the additives exemplified in Production Example 1. The amount of additive used can be 0.005 to 100 equivalents per equivalent of compound (3) or compound (3-1).

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

[0078] The compound (3) used in Production Example 1 can be produced, for example, according to the production route shown in reaction equation 3 below.

[0079] [Reaction Equation 3]

[0080] [ka]

[0081] [In the formula, X represents a halogen atom, G, R X and R Y This expresses the same meaning as above. Compound (3) can be obtained by reacting compound (3-A) and compound (C) 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, it can be obtained by reacting them in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand.

[0082] Some of the compounds (3-A) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0083] The amount of compound (C) used may be 0.5 to 50 equivalents per equivalent of compound (3-A).

[0084] Some of compound (C) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0085] When a solvent is used, it is sufficient that the solvent used is inert to the reaction; for example, the solvent exemplified in Production Example 1 is an example of such a solvent.

[0086] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-A).

[0087] Examples of copper catalysts that can be used in this reaction include monovalent copper iodide, monovalent copper trifluoromethanesulfonate benzene complex, and monovalent copper trifluoromethanesulfonate toluene complex. The amount of copper catalyst used may be 0.001 to 50 equivalents per equivalent of compound (3-A).

[0088] Examples of additives that can be used in this reaction include N,N-dimethylglycine and 4-(dimethylamino)pyridine. The amount of additive used may be 0.001 to 100 equivalents per equivalent of compound (3-A).

[0089] Examples of palladium catalysts that can be used in this reaction include palladium (divalent) (π-cinnamyl) chloride (dimer), allyl palladium (divalent) chloride (dimer), and tris(dibenzylideneacetone)dipalladium (zero valent). The amount of palladium catalyst used may be 0.001 to 50 equivalents per equivalent of compound (3-A).

[0090] Examples of ligands that can be used in this reaction 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), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos). The amount of ligand used may be 0.001 to 50 equivalents per equivalent of compound (3-A).

[0091] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0092] Of the compounds (3), R Y Compound (3-3) in which is a hydrogen atom can be produced, for example, according to the production route shown in reaction equation 4 below.

[0093] [Reaction Equation 4]

[0094] [ka]

[0095] [In the formula, R 103 represents C1-C6 alkyl, and G and R X This expresses the same meaning as above. Step 1: Compound (3-C) can be obtained by reacting compound (3-B) with compound (D) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without a solvent, and possibly in the presence of a base.

[0096] Some of compound (D) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0097] The amount of compound (D) or its salt used can be 0.5 to 50 equivalents per equivalent of compound (3-B).

[0098] Some of compound (3-B) are known compounds described in Bioorganic & Medicinal Chemistry Letters, 2015, Vol. 25, p. 4481, and others can be synthesized in the same manner as known compounds, following the methods described in the said literature.

[0099] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvent exemplified in Production Example 1 is one such example.

[0100] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-B).

[0101] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0102] Step 2: Compound (3-3) can be obtained by reacting compound (3-C) with an oxidizing agent in or without a solvent.

[0103] Examples of oxidizing agents that can be used include potassium permanganate. The amount of oxidizing agent used may be 0.1 to 100 equivalents per equivalent of compound (3-C).

[0104] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvent exemplified in Production Example 1 is one such example.

[0105] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0106] Compound (3-3) can also be produced, for example, by following the production route shown in reaction equation 5 below.

[0107] [Reaction Equation 5]

[0108] [ka]

[0109] [In the formula, G and R X This expresses the same meaning as above. Step 1: Compound (3-D) can be reacted under the same conditions as in Step 1 of Reaction Equation 4 to obtain compound (3-E).

[0110] Some of the compounds (3-D) are known compounds described in International Publication No. 2003 / 016275, and others can be synthesized in the same manner as known compounds, following the methods described in the said publication.

[0111] Step 2: Compound (3-3) can be obtained by reacting compound (3-E) with carbon dioxide in a solvent or without a solvent, in the presence of a base.

[0112] Examples of bases that can be used include n-butyllithium. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-E).

[0113] When a solvent is used, it is sufficient that the solvent is inert to the reaction; for example, the solvent exemplified in Production Example 1 is one such example.

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

[0115] Compounds (3-5) can be produced, for example, according to the production route shown in reaction equation 6 below.

[0116] [Reaction Equation 6]

[0117] [ka]

[0118] [In the formula, R 103 represents C1-C6 alkyl, R 104 G represents a hydrogen atom or a C1-C6 alkyl group. 1a represents C1-C6 alkyl or C3-C6 cycloalkyl, and L, X, R X and R Y This expresses the same meaning as above. Step 1: Compound (3-F) can be obtained by reacting compound (3-4) and compound (E) in a solvent or without a solvent in the presence of a base.

[0119] Some of compound (E) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0120] The amount of compound (E) used may be 0.5 to 50 equivalents per equivalent of compound (3-4).

[0121] When a solvent is used, it is sufficient that the solvent used is inert to the reaction; for example, the solvent exemplified in Production Example 1 is an example of such a solvent.

[0122] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-4).

[0123] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0124] Compounds (3-4) can be synthesized according to the method of reaction formula 4.

[0125] Step 2: Compound (3-G) can be obtained by reacting compound (3-F) with compound (F) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of a palladium catalyst and ligand.

[0126] Some of the compounds (F) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0127] The amount of compound (F) used can be 0.5 to 50 equivalents per equivalent of compound (3-F).

[0128] When a solvent is used, it is sufficient that the solvent used is inert to the reaction; for example, the solvent exemplified in Production Example 1 is an example of such a solvent.

[0129] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-F).

[0130] Examples of palladium catalysts that can be used in this reaction include the palladium catalyst illustrated in reaction formula 3. The amount of palladium catalyst used may be 0.001 to 50 equivalents per equivalent of compound (3-F).

[0131] Examples of ligands that can be used in this reaction include the ligands exemplified in reaction formula 3. The amount of ligand used may be 0.001 to 50 equivalents per equivalent of compound (3-F).

[0132] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0133] When a solvent is used, it is sufficient that the solvent used is inert to the reaction; for example, the solvent exemplified in Production Example 1 is an example of such a solvent.

[0134] Step 3: Compound (3-5) can be obtained by reacting compound (3-G) in a solvent or without a solvent, and possibly in the presence of a base.

[0135] Examples of bases that can be used in this reaction include the bases exemplified in Production Example 1. The amount of base used may be 0.1 to 100 equivalents per equivalent of compound (3-G).

[0136] The reaction temperature and reaction time are within the temperature and time ranges described in Production Example 1.

[0137] The compound (4) used in Production Example 1 can be produced, for example, according to the production route shown in the reaction equation 7 below.

[0138] [Reaction Equation 7]

[0139] [ka]

[0140] [In the formula, R 2 , R 3 , Z 1 , Z 2 And n4 has the same meaning as above. Step 1: Compound (4-A) can be obtained by reacting compound (B) with N-hydroxyphthalimide in accordance with known methods described in the literature, for example, the method described in Example 45 of International Publication No. 2010 / 050468.

[0141] Some of compound (B) are known compounds, and some are available commercially. Others can be manufactured according to the general synthesis methods of known compounds described in the literature.

[0142] Step 2: Compound (4) can be obtained by reacting compound (4-A) with hydrazine monohydrate or an aqueous hydrazine solution in accordance with a known method described in the literature, for example, the method described in Example 1 of Japanese Patent Application Publication No. 2014-130014.

[0143] The compounds of the present invention can generally be used as fungicides and antifungal agents for agricultural and horticultural purposes against various diseases caused by root-leaved molds, oomycetes, zygomycetes, ascomycetes, basidiomycetes, imperfect fungi, bacteria, or viruses.

[0144] "Pathogenic fungi" refers to microorganisms that cause plant diseases, and specifically includes, but is not limited to, the following microorganisms.

[0145] 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., S. homoeocarpa, S. minor, S. sclerotiorum 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. (for example, Pestalotia eriobotrifolia, etc.), Pestalotiopsis 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.(e.g., spinaciae), Glomerella spp. (e.g., Glomerella cingulata), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola), Phaeocytostroma spp., Phialophora spp. (e.g., Phialophora gregata), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium Ascomycota fungi such as *Secalis*, *Sarocladium* spp., *Coleophoma* spp., and *Helicoceras oryzae*. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g., Helicobasidium longisporum, etc.), Coleosporium spp. (e.g., Coleosporium plectranthi, etc.), Cronarium 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), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum), Conocybe spp. (e.g., Conocybe apala), Marasmius spp. (e.g., Marasmius oreades), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda), Scleroti. Fungi of the phylum Basidiomycota, such as um spp. (e.g., Sclerotium cepivorum), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis), Athelia spp. (e.g., Athelia rolfsii), Ceratobasidium spp. (e.g., Ceratobasidium cornigerum), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani), Thanatephorus spp. (e.g., Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp. Fungi of the phylum Chitridiomycota, such as Olpidium spp. Fungi of the phylum Blastocoliomycota, such as Physoderma spp. Fungi of the subphylum Mucoromycotina, such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), 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), Spongospora subterranea f. sp. Subterranea. Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyaloperonosspora 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. buismaniae、P. debaryanum、P. graminicola、P. horinouchiense、P. irregulare、P. iwayamai、P. myriotylum、P. okanoganense、P. paddicum、P. paroecandrum、P. periplocum、P. spinosum, P. ultimum, P. vexans. volutum (Heterokontophyta) strains (Oomycetes) of Clavibacter spp., Clavibacter michiganensis subsp.Gram-positive bacteria of the phylum Actinobacteria, such as Actinobacteria michiganensis, Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli), and Streptomyces spp. (e.g., Streptomyces ipomoeae). Gram-positive bacteria of the phylum Firmicutes, such as Clostridium sp. Gram-positive bacteria of the phylum Tenericutes, such as Phytoplasma. Rhizobium spp. (e.g., Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g., Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g., Acidovorax avenae subsp. avenae, 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 belonging to the phylum Proteobacteria (e.g., *P. atrosepticum*, *P. carotovorum*, *P. wasabiae*, etc.).

[0146] Specific examples of plant diseases caused by infection and proliferation of these pathogens include, but are not limited to, the following.

[0147] Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), sugar beet leaf spot (Cercospora beticola), bell pepper frogeye leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown leaf spot (Mycosphaerella arachidis), cherry brown leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), black sigatoka (Mycosphaerella fijiensis), yellow sigatoka Sigatoka (Mycosphaerella musicola), Wheat leaf blotch (Mycosphaerella graminicola), Persimmon circular leaf spot (Mycosphaerella nawae), Pea brown spot (Mycosphaerella blight) (Mycosphaerella pinodes), Ginger leaf spot (Mycosphaerella zingiberis), Tomato leaf mold (Mycovellosiella fulva), Eggplant sooty mold (Mycovellosiella nattrassii), Tomato sooty mold (Pseudocercospora fuligena), Grape brown spot (Isariopsis leaf spot) (Pseudocercospora vitis), Chinese cabbage white spot (Leaf spot) (Pseudocercosporella capsellae), Chrysanthemum black spot (Leaf spot) (SeptoriaChrysanthemella, Leaf blight (Septoria obesa), Anthracnose (Elsinoe ampelina), Spot anthracnose (Elsinoe araliae), Scab (Elsinoe fawcettii), Leaf spot (Ascochyta pisi), Corynespora leaf spot (Corynespora cassiicola), Stem canker (Leptosphaeria coniothyrium), Glume blotch (Leptosphaeria nodorum), Leaf spot (Alternaria alternata), Cabbage leaf spot (Alternaria brassicae), Leaf blight (Alternaria dauci), Pear black spot (Alternaria Alternaria blotch (Alternaria mali), Alternaria leaf spot (Alternaria porri), Target spot (Bipolaris sorghicola), Southern leaf blight (Cochliobolus heterostrophus), Brown spot (Cochliobolus miyabeanus), Tip blight (Pleospora herbarum), Stripe (Pyrenophora graminea), Net blotch (Pyrenophora teres), Leaf blight (Setosphaeria turcica), Northern leaf blight (Setosphaeria turcica), Leaf spot (Stemphylium)Scab (Venturia carpophila), apple scab (Venturia Inaequalis), pear scab (Venturia nashicola), gummy stem blight (Didymella bryoniae), leaf spot (Phoma exigua var. exigua), wasabi streak (Phoma wasabiae), ring rot (Botryosphaeria berengeriana f. sp. piricola), kiwi fruit soft rot (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), common green mold (Penicillium digitatum), blue mold (Penicillium Powdery mildew affecting various crops (italicum), barley powdery mildew (Blumeria graminis f. sp. hordei), wheat powdery mildew (Blumeria graminis f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), bell pepper powdery mildew (Leveillula Powdery mildew (Oidium sp., Podosphaera xanthii), powdery mildew (Oidium sp., Podosphaera xanthii), powdery mildew (Oidium sp.), powdery mildew (Phyllactinia)Powdery mildew (Potamogeton fusca), powdery mildew (Podosphaera leucotricha), powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), powdery mildew (Podosphaera xanthii) on zucchini and cantaloupe, powdery mildew (Sphaerotheca aphanis var. aphanis) on strawberries, powdery mildew (Sphaerotheca fuliginea) on watermelons and melons, powdery mildew (Uncinula necator, U. n. var. necator) on grapes, apple blotch (Diplocarpon mali), rose black spot (Diplocarpon rosae), gray mold neck rot (Botrytis) Gray mold (Botrytis cinerea), white leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), 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 sclerotiorum). Fusarium blight (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae)Monographella nivalis), Fusarium blight (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of colocasia (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.Fusarium wilt (Fusarium oxysporum f. sp. spinaciae), soybean sudden death syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), rice bakanae disease (Gibberella fujikuroi), radish verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, eggplant, and butterbur verticillium wilt (Verticillium dahliae), fig canker (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), and tea ring spot (Gray). blight (Pestalotiopsis longiseta, P. theae), chestnut blight Endothia canker (Cryphonectria parasitica), citrus black spot Melanose (Diaporthe citri), asparagus stem blight Stem blight (Phomopsis asparagi), pear blight Phhomopsis canker (Phomopsis fukushii), eggplant brown spot (Phomopsis vexans), tea anthracnose (Discula theae-sinensis), apple canker (Valsa ceratosperma), rice blast (Magnaporthe grisea), strawberry anthracnose Crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), apple anthracnose Bitter rot (Colletotrichum acutatum, Anthracnose (Colletotrichum acutatum, GlomerellaAnthracnose (Colletotrichum acutatum), plum anthracnose, grape late blight (Ripe rot, Colletotrichum acutatum, Glomerella cingulata), chrysanthemum anthracnose (Colletotrichum acutatum), kidney bean anthracnose (Colletotrichum lindemuthianum), cucurbit anthracnose (Colletotrichum orbiculare), yam anthracnose (Glomerella cingulata), chestnut anthracnose (Glomerella cingulata), persimmon anthracnose (Glomerella cingulata), adzuki bean leaf spot (Brown stem rot, Philophora gregata), yam leaf spot Spot (Pseudophloeosporella dioscoreae), Barley Scald (Rhynchosporium secalis), Wheat Brown Rust (Puccinia recondita), Wheat Stripe Rust (Puccinia striiformis), Rust affecting various crops, Fig Rust (Phakopsora nishidana), Soybean Rust (Phakopsora pachyrhizi), Rose Rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), Pear Red Rust (Gymnosporangium asiaticum), Apple Red Rust (Gymnosporangium yamadae), Rust of the Alliaceae family (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 (Sporisorium)Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani, Rhizoctonia solani) solani), rice sheath blight (Thanatephorus cucumeris), sugar beet root rot (Thanatephorus cucumeris), sugar beet leaf blight (Thanatephorus cucumeris), fig black mold (Rhizopus rot, Rhizopus stolonifer var. stolonifer), cruciferous vegetable clubroot (Plasmodiophora brassicae), sugar beet black root rot (Aphanomyces cochlioides), cruciferous white rust (Albugo macrospora), downy mildew affecting various crops, lettuce downy mildew (Bremia lactucae), garland chrysanthemum downy mildew (Peronospora chrysanthemi-coronarii), onion and leek downy mildew (Peronospora Destructor), spinach downy mildew (Peronospora farinosa f. sp. spinaciae), soybean downy mildew (PeronosporaDowny mildew of manshurica, Brassicaceae (Peronospora parasitica), rose downy mildew (Peronospora sparsa), sunflower downy mildew (Plasmopara halstedii), three-leaf downy mildew (Plasmopara nivea), grape downy mildew (Plasmopara viticola), Cucurbitaceae downy mildew (Pseudoperonospora cubensis), Aralia elata root rot (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), pumpkin rot (Phytophthora capsici), bell pepper rot (Phytophthora capsici), watermelon rot (Phytophthora cryptogea), tomato and potato late blight (Phytophthora fig blight (infestans) White powdery rot (Phytophthora palmivora), white blight of the onion family (Phytophthora porri), soybean stem blight (Phytophthora root and stem rot, Phytophthora sojae), adzuki bean stem blight (Phytophthora vignae f. sp. adzukicola), spinach damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), konjac root rot (Pythium aristosporum), corn root rot (Pythium arrhenomanes, P. graminicola), cabbage seedling damping-off (Pythium buismaniae, P. myriotylum), myoga rhizome rot rot (Pythium myriotylum), ginger root rot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato 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.Bacterial diseases of various plants including glumae, watermelon fruit blotch (Acidovorax avenae subsp. citrulli), konjac leaf blight (Acidovorax konjaci), bacterial wilt (Ralstonia solanacearum), peach shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria nigrifluens), plum leaf spot (Xanthomonas arboricola pv. pruni), lettuce bacterial spot (Xanthomonas axonopodis pv. vitians), black rot of brassicas (Xanthomonas campestris pv. campestris), and soybean leaf blight. 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.), Bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), 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), bacterial spot disease of the Cucurbitaceae family (Pseudomonas syringae pv. lachrymans), bacterial black spot disease of the Brassicaceae family (Pseudomonas syringae pv. maculicola), bacterial canker disease of the plum (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), bacterial shoot blight of the tea plant (Pseudomonas syringae pv. theae), bacterial soft rot of the leek (Dickeya sp., Pectobacterium carotovorum), fire disease of the Rosaceae family (Porcelain subfamily) blight (Erwinia amylovora), konjac rot Soft rot (Pectobacterium carotovorum), Bacterial soft rot (Pectobacterium carotovorum). .

[0148] The development of control agents for diseases affecting agricultural and horticultural crops has progressed, and a wide variety of agents have been put into practical use to date. However, due to the long-term use of these agents, pathogens have recently acquired drug resistance, making it increasingly difficult to control diseases with conventionally used fungicides. Furthermore, some existing agents are highly toxic, and others remain in the environment for long periods, causing problems that disrupt ecosystems. Under these circumstances, the compound of the present invention has excellent control activity against many pathogens and is highly safe for the target crops. Moreover, the compound of the present invention can exert sufficient control effects even against pathogens 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 effects on mammals, fish, and beneficial insects, has low persistence, and has a light burden on the environment.

[0149] In addition to its use as a fungicide for agriculture and horticulture, the compound of the present invention can also be used as a medical antimicrobial agent and veterinary antimicrobial agent used as an antifungal agent or internal parasite control agent, as an antibacterial and antifungal agent for wood, paper and pulp, adhesives and paints, textiles and leather, etc., and as an industrial disinfectant for cooling water channels in manufacturing plants, etc.

[0150] Examples of pathogenic bacteria targeted as antimicrobial agents for medical or veterinary use include, but are not limited to, dermatophytes such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida such as Candida albicans, Aspergillus such as Aspergillus fumigatus, Cryptococcus such as Cryptococcus neoformas, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa and Haemophilus influenzae, and Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0151] Examples of fungal strains targeted as antibacterial and antifungal agents include wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor, and material degradation 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.

[0152] Examples of bacterial strains targeted for industrial disinfectant use include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.

[0153] In addition to its use as a fungicide for agricultural and horticultural purposes, the compound of the present invention can also be used as a control agent for internal parasites in livestock, poultry, or pet animals.

[0154] The following are some specific examples of internal parasites that may be affected, but they are not limited to these.

[0155] Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Couperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongirus Nematodes such as those belonging to the genera *Trichonema*, *Dictyocaulus*, *Capillaria*, *Heterakis*, *Toxocara*, *Ascaridia*, *Oxyuris*, *Ancylostoma*, *Uncinaria*, *Toxascaris*, and *Parascaris*; Nematodes of the family Filariidae, including genera such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Nematodes of the family Dracunculidae, such as the genus Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium tapeworms such as Diphyllobothrium erinacei, Echinococcus granulosus, and Echinococcus multilocularis; Fasciola hepatica, F. gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma fluke such as Schistosoma haematobium, Schistosoma mansoni; Eimeria spp., such as Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, and Eimeria ovinoidalis; Examples include Trypanosomsa cruzi, Leishmania spp., Plasmodium spp., Babesia spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., etc.

[0156] In addition to its use as a fungicide for agricultural and horticultural purposes, the compound of the present invention can also be used as an antifungal agent.

[0157] The following are some specific examples of pathogens targeted by antifungal agents, but they are not limited to these.

[0158] This includes ringworm fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, and Cryptococcus fungi such as Cryptococcus neoformas.

[0159] When applying the compounds of the present invention as a plant disease and pest control agent, the compounds are usually mixed with a suitable solid or liquid carrier, and optionally, surfactants, penetrating agents, spreading agents, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, or decomposition inhibitors are added to produce formulations of any dosage form, such as soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granule, water-soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, or gel. Furthermore, from the viewpoint of saving labor and improving safety, the formulations of any of the above dosage forms can also be provided enclosed in water-soluble packaging.

[0160] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, or diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, or potassium chloride; synthetic silicic acid; or synthetic silicates.

[0161] Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol, or isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, or alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, or castor oil; or water. These solid and liquid carriers may be used individually or in combination of two or more.

[0162] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, or polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkylnaphthalene sulfonates, salts of formalin condensates of naphthalene sulfonic acid, salts of formalin condensates of alkylnaphthalene sulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, or polystyrene sulfonates; cationic surfactants such as alkylamine salts or alkyl quaternary ammonium salts; or amphoteric surfactants such as amino acid type or betaine type.

[0163] The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention. Furthermore, these surfactants may be used individually or in combination of two or more types.

[0164] When using the compound of the present invention as an agricultural chemical, it may be mixed and applied with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, or soil conditioners, as needed, during formulation or application.

[0165] In particular, by mixing and applying it with other pesticides or plant hormones, it is possible to reduce costs by decreasing the amount of pesticide applied, expand the fungicidal and insecticidal spectrum through the synergistic effect of the mixed agents, or achieve a higher pest control effect. In this case, it is also possible to combine it with multiple known pesticides simultaneously.

[0166] In one embodiment, examples of pesticides used in combination with the compounds of the present invention include compounds described in The Pesticide Manual, 18th edition, 2018. Specific examples of their common names are as follows. However, the pesticides used in combination are not necessarily limited to these.

[0167] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide Polysulfide), Benalaxyl, Benalaxyl-M, Benodanil, Benomyl, Benquinox, Bentaluron, Benthiavalicarb-isopropyl, Benthiazole, Benzamacril, Benzamorf, Benzovindiflupyr, Binapacryl, Biphenyl, Bitertanol, Bixafen, Blastoicidin-S, Bordeaux mixture mixture), boscalid, bromoconazole, bupirimate, butthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, cheshunt mixture, chinomethionate,Chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlorzolinate, 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, decafentin, dehydroacetate acid), diclobentiazox, dichlofluanid, dichloone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine,Dichloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4 Nocap-4), Dinocap-6, Dinocton, Dinosulfon, Dinoterbon, Diphenylamine, Dipymetitrone, Dipyrithione, Disulfiram, Ditalimfos, Dithianon, DNOC, Dodemorph, Dodin ne), drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxyconazole, etaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamid Fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid,Fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumethovell 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, flu Furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole ole), ipuflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isoflucypram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin, Kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil onil), meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb, metofloxam, methyltetraprole, metiram, metominostrobin,Metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazole fumarate fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium bicarbonate 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 Pyridachlometyl, 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, thioc, Lorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinil, tioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide Examples include 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.

[0168] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanicarb, aldicarb, allethrin, Alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis (thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, biorethmetrin smethrin), bistrifluron, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionate, chlorantraniliprole, chlorethoxyfos,Chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezine zine), clothianidin, cyanophos, cyantraniliprole, cyclaniliprole, cycloprothrin, cyenopyrafen, cyetpyrafen, cyflumetofen, cyfluthrin, cyhalodiamide, cyhalothrin (cyh alothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezothia z), dicofol, dienochlor, diflovidazin, diflubenzuron, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC,dT-80-phthalthrin (d-tetramethrin), emamectin-benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethiofencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubenji 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, mesoprene, methoxychlor, methoxyfenozide, methyl bromide, metofluthrin, milbemectin, momfluorothrin,Monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, nobiflumulon, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl (p (Parathion-methyl), pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, praziquantel (Praz 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, spiropidion, spirotetramat, spyromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluth Examples include rin, tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, trizamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, and zeta-cypermethrin.

[0169] Antiparasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, alpha-cypermethrin, 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, chlorthulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide), emodepside, epsiplantel, febantel, fenbendazole, flubendazole, glycopyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, metronidazole, methylidine,Examples include 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.

[0170] Antifungal agents: Ketoconazole and miconazole nitrate, etc.

[0171] Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid Oxolinic 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 seashell calcium (calcium oxide), Talaromyces, Trichoderma, and Uniotyrium, etc.

[0172] The appropriate amount of the compound of the present invention to be applied varies depending on the application situation, timing of application, method of application, and cultivated crop, but generally, an amount of 0.005 to 50 kg per hectare (ha) as the amount of active ingredient is appropriate, with 0.01 to 1 kg being preferred.

[0173] Next, examples of formulations using the compound of the present invention are shown. However, the examples of formulations of the present invention are not limited to these. In the following examples of formulations, "parts" means parts by weight.

[0174] [Wettable powder] 0.1 to 80 parts of the compound of the present invention Solid carrier 5-98.9 parts Surfactant 1-10 parts Others: 0-5 copies Other examples include anti-caking agents or anti-decomposition agents.

[0175] 〔emulsion〕 0.1 to 30 parts of the compound of the present invention Liquid carrier 45-95 parts Surfactant 4.9-15 parts Other 0-10 copies Other examples include spreading agents or decomposition inhibitors.

[0176] [Suspension] 0.1 to 70 parts of the compound of the present invention Liquid carrier: 15-98.89 parts Surfactant 1-12 parts Other 0.01-30 copies Other examples include, for instance, antifreeze or thickening agents.

[0177] [Granular wettable powder] 0.1 to 90 parts of the compound of the present invention Solid carrier 0-98.9 parts Surfactant 1-20 parts Other 0-10 copies Other examples include binders or decomposition inhibitors.

[0178] [Liquid formulation] 0.01 - 70 parts of the compound of the present invention 20 - 99.99 parts of liquid carrier 0 - 10 parts of others Examples of others include antifreezing agents or spreading agents, etc.

[0179] [Granule formulation] 0.01 - 80 parts of the compound of the present invention 10 - 99.99 parts of solid carrier 0 - 10 parts of others Examples of others include binders or decomposition inhibitors, etc.

[0180] [Powder formulation] 0.01 - 30 parts of the compound of the present invention 65 - 99.99 parts of solid carrier 0 - 5 parts of others Examples of others include drift inhibitors or decomposition inhibitors, etc.

[0181] In use, the above formulations are diluted 1 - 10000 times, preferably 100 - 10000 times with water, or sprayed without dilution.

[0182] Next, formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient are shown more specifically. However, the formulations of the present invention include, but are not limited to, these including the compound of the present invention. In the following formulation examples, "parts" means parts by weight.

[0183] [Formulation Example 1] Emulsion 20 parts of Compound No.1 - 001 of the present invention 55 parts of methylnaphthalene 20 parts of cyclohexanone 5 parts of Solpol 2680 (Mixture of non - ionic surfactant and anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) The above ingredients are uniformly mixed to form an emulsion. When using, the emulsion is diluted with water 50 to 20,000 times and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0184] [Formulation Example 2] Wettable Powder Compound No. 1-001 of the present invention: 25 parts Pyrophyllite 66 pieces Solpol 5039, 4 parts (Anionic surfactant: Manufactured by Toho Chemical Industry Co., Ltd., product name) Carplex #80D Part 3 (White carbon: Manufactured by Shionogi & Co., Ltd., product name) Calcium lignin sulfonate (2 parts) The above ingredients are uniformly mixed and ground to form a wettable powder. When using, the wettable powder is diluted with water 50 to 20,000 times and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0185] [Formulation Example 3] Powder Compound No. 1-001 of the present invention (3 parts) Carplex #80D 0.5 bu (White carbon: Manufactured by Shionogi & Co., Ltd., product name) Kaolinite 95 copies Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and ground to form a powder. When using, the powder should be spread so that the amount of active ingredients is 0.005 to 50 kg per hectare.

[0186] [Formulation Example 4] Granules Compound No. 1-001 of the present invention (5 parts) Bentonite 30 units Talc 64 pieces Calcium lignin sulfonate (part 1) The above ingredients are uniformly mixed and ground, a small amount of water is added and stirred, then granulated using an extrusion granulator and dried to form granules. When using, the granules should be spread so that the amount of active ingredients is 0.005 to 50 kg per hectare.

[0187] [Formulation Example 5] Flowable Agent 25 parts of Compound No. 1-001 of the present invention 5 parts of Solpol 3353 (Nonionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) 0.5 part of Lennox 1000C (Anionic surfactant: manufactured by Toho Chemical Industry Co., Ltd., trade name) 0.2 part of xanthan gum (natural polymer) 0.4 part of sodium benzoate 10 parts of propylene glycol 58.9 parts of water The above components excluding the active ingredient (the compound of the present invention) were uniformly dissolved, then the compound of the present invention was added and stirred well, and then wet pulverized with a sand mill to obtain a flowable agent. When in use, the flowable agent 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.

[0188] A [Formulation Example 6] Dry Flowable Agent 75 parts of Compound No. 1-001 of the present invention 5 parts of Hitenol NE-15 (Anionic surfactant: manufactured by Daiichi Kogyo Seiyaku Co., Ltd., trade name) 10 parts of Vanirex N (Anionic surfactant: manufactured by Nippon Paper Industries Co., Ltd., trade name) 10 parts of Carplex #80D A (White carbon: manufactured by Shionogi & Co., Ltd., trade name) The above components were uniformly mixed and finely pulverized, a small amount of water was added and stirred and mixed, granulated with an extrusion granulator, and dried to obtain a dry flowable agent. When in use, it is diluted 50 to 20,000 times with water and sprayed so that the active ingredient becomes 0.005 to 50 kg per hectare.

[0189] Examples of the application method of the compound of the present invention include foliar spraying, soil treatment, or seed disinfection, etc., and it is also effective in general methods commonly used by those skilled in the art.

[0190] 〔summary〕 As described above, the present invention relates to the following [1] to [7].

[0191] [1] Formula (1):

[0192] [ka]

[0193] [In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula:

[0194] [ka]

[0195] G 1 These are hydroxy, nitro, cyano, halogen atoms, C1-C6 alkyl, and C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Represents cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, G 1 In relation to this, if m5 represents an integer of 2, 3, 4, or 5, then each G 1 They may be the same as each other, or they may be different from each other. R X C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1, R X -2, R X -3 or R X -4 represents, R X -1~R X-4 represents the structure shown in the following structural formulas,

[0196] [ka]

[0197] X 1 This represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. X 1 In relation to X, if u5 represents an integer of 2, 3, 4, or 5, then each X 1 They may be the same as each other, or they may be different from each other. X 1 In relation to u4, if u4 represents an integer of 2, 3, or 4, then each X 1 They may be the same as each other, or they may be different from each other. R Y This represents a hydrogen atom or a halogen atom, R 2 This represents a hydrogen atom or a C1-C6 alkyl group. R 3 This represents a hydrogen atom or a C1-C6 alkyl group. Z 1 This represents E-1 to E-8 or E-9, Z 2 These are hydroxy, carboxy, amino, nitro, cyano, halogen atoms, C1-C6 alkyl, and C3-C 10 This represents a cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 alkylthio. Z 2 In relation to this, if n4 represents an integer of 2, 3, or 4, then each Z 2 They may be the same as each other, or they may be different from each other. E-1 to E-10 represent structures represented by the following structural formulas,

[0198] [ka]

[0199] Z a These are halogen atoms, C1-C6 alkyl, C3-C 10 This represents a cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, or C1-C6 alkylthio. Z a In relation to this, if v3 represents an integer of 2 or 3, then each Z a They may be the same as each other, or they may be different from each other. Z a In relation to this, if v2 represents an integer of 2, then each Z a They may be the same as each other, or they may be different from each other. Z b This represents C1-C6 alkyl, m5 represents an integer of 0, 1, 2, 3, 4, or 5. n4 represents an integer of 0, 1, 2, 3, or 4. u5 represents an integer of 0, 1, 2, 3, 4, or 5. u4 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 either 0 or 1. A pyrazole compound represented by or a salt thereof.

[0200] [2] G 1 This represents a C1-C6 alkyl or C1-C6 haloalkyl group. R X This represents C1-C6 alkyl, R Y This represents a hydrogen atom, R 2 This represents a hydrogen atom, R 3 This represents a hydrogen atom, Z a C1-C6 alkyl or C3-C 10 Represents cycloalkyl, m5 represents the integer 1, n4 represents an integer equal to 0. v3 represents an integer of 0 or 1. v2 represents an integer of 0 or 1. v1 is the pyrazole compound or salt thereof described in [1] above, representing an integer of 0.

[0201] [3] A pesticide containing one or more pyrazole compounds and salts thereof selected from either item [1] or [2] above as an active ingredient.

[0202] [4] A bactericide containing one or more pyrazole compounds and salts thereof selected from either item [1] or [2] above as an active ingredient.

[0203] [5] A fungicide for agricultural and horticultural use, containing one or more pyrazole compounds and salts thereof selected from either item [1] or [2] above as an active ingredient.

[0204] [6] An antifungal agent containing one or more pyrazole compounds and salts thereof selected from either item [1] or [2] above as an active ingredient.

[0205] [7] An internal parasite control agent containing one or more pyrazole compounds and salts thereof selected from either item [1] or [2] above as an active ingredient.

[0206] [Examples] The present invention will be further described below by illustrating examples of the synthesis and testing of the compounds of the present invention, but the present invention is not limited thereto.

[0207] For the intermediate-pressure preparative liquid chromatography described in the synthesis example, we used the YAMAZEN Corporation intermediate-pressure preparative apparatus; YFLC-Wprep (flow rate 18 ml / min, silica gel column 40 μm).

[0208] Furthermore, the proton nuclear magnetic resonance spectra described below (hereinafter,1 The chemical shift values ​​of ¹H-NMR (referred to as ¹H-NMR) were measured using Me₄Si (tetramethylsilane) as the reference material, at 300 MHz (model: JNM-ECX300 or JNM-ECP300, JEOL Corporation) or 400 MHz (model: JNM-ECZ400S, JEOL Corporation). 1 The symbols used in the chemical shift values ​​of H-NMR represent the following:

[0209] s: singlet, d: doublet, t: triplet, m: multiplet, br: broad singlet.

[0210] [Example of combination] Synthesis Example 1: Synthesis of 1-(tert-butyl)-N-((4-(5-cyclopropylisoxazole-3-yl)benzyl)oxy)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-015).

[0211] To a mixed solution of 82 mg of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid and 1 ml of N,N-dimethylformamide, 171 mg of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 0.20 ml of N,N-diisopropylethylamine, and 80 mg of O-(4-(5-cyclopropylisoxazole-3-yl)benzyl)hydroxylamine hydrochloride were sequentially added at room temperature, and the mixture was stirred at the same temperature for 16 hours. After the reaction was complete, 3 ml of water was added to the reaction mixture, and it was extracted with a mixed solution of n-hexane:ethyl acetate = 1:1 (volume ratio, the same applies hereafter) (4 ml x 1 time). The resulting organic layer was washed with 1 mol / l hydrochloric acid, dehydrated and dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as the eluent, yielding 79 mg of the target substance as an oily material.

[0212] 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.15 (br, 1H), 7.70-7.65 (m, 2H), 7.44-7.40 (m, 2H), 7.17-7.10 (m, 2H), 6.92-6.87 (m, 1H), 6.74-6.71 (m, 2H), 6.17 (s, 1H), 4.96 (s, 2H), 2.28 (s, 3H), 2.14-2.05 (m, 1H), 1.72 (s, 9H), 1.15-0.98 (m, 4H).

[0213] Synthesis Example 2: Synthesis of 1-(tert-butyl)-N-((4-(1-methyl-1H-pyrazole-3-yl)benzyl)oxy)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-002).

[0214] 300 mg of 1-(tert-butyl)-N-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 144 mg of sodium iodide, and 2 ml of N,N-dimethylformamide were mixed together. To this mixture, 0.3 ml of N,N-diisopropylethylamine was added under ice cooling, and the mixture was stirred at room temperature for 18 hours. After the reaction was complete, 5 ml of water was added to the reaction mixture, and it was extracted with ethyl acetate (5 ml x 1 time). The resulting organic layer was washed with water, dehydrated and dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate [gradient from 8:2 to 5:5 (volume ratio, the same applies below)] as the eluent, and 99 mg of the target product was obtained as an oil.

[0215] 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 8.87 (br, 1H), 7.71 (d, J = 8.2 Hz, 2H), 7.37-7.33 (m, 5H), 7.23-7.21 (m, 1H), 7.14-7.11 (m, 1H), 7.09-7.02 (m, 1H), 6.50 (d, J = 2.4 Hz, 1H), 4.94 (s, 2H), 3.95 (s, 3H), 1.72 (s, 9H).

[0216] [Reference example] The following shows a method for producing the intermediate compound of the present invention as a reference example.

[0217] Reference example 1: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid.

[0218] Step 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)buta-3-en-2-one.

[0219] 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 complete, the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as the eluent. 10 ml of diisopropyl ether and 10 ml of n-hexane were added to the resulting oily substance, and the precipitated solid was filtered off. The resulting solid was dried under reduced pressure to obtain 2.36 g of the target product as a light brown solid.

[0220] Melting point: 112-114°C.

[0221] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole.

[0222] A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)buta-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 complete, the solvent was removed under reduced pressure. 20 ml of water was added to the resulting residue, and the mixture was extracted with n-hexane (20 ml twice). The resulting organic layer was dehydrated and dried with saturated brine, then anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (5:1) as the eluent, yielding 2.51 g of the target product as a pale yellow oil.

[0223] 1 H-NMR (CDCl3, Me4Si, 300MHz):δ7.42-7.32 (m, 1H), 7.28 (s, 1H), 7.28-7.22 (m, 1H), 7.21-7.14 (m, 1H), 7.12-7.04 (m, 1H), 2.29 (s, 3H), 1.66 (s, 9H).

[0224] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid.

[0225] 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 were mixed and 1.48 g of potassium permanganate was added at room temperature and the mixture was stirred at 100°C for 2 hours. After stirring, 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 complete, the reaction mixture was filtered through Celite and washed with 20 ml of water. The aqueous layer of the resulting filtrate was washed with chloroform (20 ml twice), and then 1 mol / l hydrochloric acid was added until the pH became 1, and the mixture was extracted with chloroform (20 ml twice). The resulting organic layer was washed with water, dehydrated and dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained solid was washed with 5 ml of n-hexane and dried under reduced pressure to obtain 209 mg of the target substance as a white solid.

[0226] Melting point: 120-124°C.

[0227] Reference example 2: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid.

[0228] Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrylaldehyde.

[0229] To 15 ml of N,N-dimethylformamide, 5.6 ml of phosphorus oxychloride was added under ice cooling, and the mixture was stirred at the same temperature for 15 minutes. After stirring, a 5 ml solution of 1-(2,2-dimethoxyethoxy)-3-(trifluoromethyl)benzene in 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 complete, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water, and 5 ml of ethanol, and stirred at room temperature for 1 hour. After stirring, the reaction mixture was extracted with toluene (40 ml x 2 times). The resulting organic layer was washed with water, dehydrated and dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 4.40 g of the target product as a brown oily substance.

[0230] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ8.82 (s, 1H), 7.52-7.03 (m, 3H), 7.03-6.95 (m, 1H), 6.62 (s, 1H), 3.12 (br, 6H).

[0231] 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 complete, 20 ml of 1 mol / l hydrochloric acid was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml twice). The resulting organic layer was washed with water, then dehydrated and dried with saturated brine, followed by anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (a gradient from 9:1 to 1:9) as the eluent, and 400 mg of the target product was obtained as a red oil.

[0232] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.46-7.20 (m, 7H), 7.20-7.14 (m, 2H), 7.10-7.06 (m, 1H), 7.03-6.96 (m, 1H), 5.29 (s, 2H).

[0233] Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid.

[0234] Under a nitrogen atmosphere, 0.85 ml of 1.6 mol / l n-butyllithium in n-hexane solution was added dropwise to 10 ml of 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 stirring, 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 complete, 10 ml of 1 mol / l hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml x 2 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting 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 the eluent, and 45 mg of the target product was obtained as a colorless solid.

[0235] Melting point: 124-126°C.

[0236] Reference example 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid.

[0237] Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate.

[0238] 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 sequentially added at room temperature, and the mixture was stirred at the same temperature for 3 hours. After the reaction was complete, the solvent was removed 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 with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 0.90 g of the target product as a yellow solid.

[0239] Melting point: 69-71°C.

[0240] Step 2: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate methyl (compound No. ii-005).

[0241] 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 mixed and 0.10 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride was added at room temperature and the mixture was stirred at 100°C for 16 hours. After the reaction was complete, 20 ml of water was added to the reaction mixture and extracted with ethyl acetate (20 ml x 3 times). After dehydration and drying with saturated brine and then anhydrous sodium sulfate, the solvent was removed 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 the eluent to obtain 0.30 g of the target product as a yellow oily substance.

[0242] 1 H-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).

[0243] Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid A mixed solution of 39.0 g of methyl (1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate) and 100 ml of methanol was mixed with a mixed solution of 27.1 g of sodium hydroxide and 100 ml of water at room temperature, and the mixture was stirred at 45°C for 16 hours. After the reaction was complete, the solvent was removed under reduced pressure. 50 ml of water was added to the resulting residue, and then 35% by mass hydrochloric acid was added until the pH became 2. The precipitated solid was filtered off. 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.

[0244] Melting point: 116-118°C.

[0245] Reference example 4: Synthesis of 1-(tert-butyl)-N-hydroxy-4-phenoxy-1H-pyrazole-5-carboxamide.

[0246] To a mixed solution of 1.00 g of 1-(tert-butyl)-4-phenoxy-1H-pyrazole-5-carboxylic acid and 10 ml of dichloromethane, 0.98 g of oxalyl chloride and 11 mg of N,N-dimethylformamide were sequentially added under ice cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, the solvent was removed under reduced pressure, and 70 ml of dichloromethane was added to the resulting residue. This reaction mixture was added under ice cooling to a mixed solution of 1.06 g of hydroxylamine hydrochloride, 1.96 g of N,N-diisopropylethylamine and 30 ml of dichloromethane, and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, 1 mol / l hydrochloric acid was added to the reaction mixture, and it was extracted with dichloromethane (10 ml x 1 time). The resulting organic layer was dehydrated and dried with saturated brine, then with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 1.08 g of the target product as a pale yellow solid.

[0247] Melting point: 122-124°C.

[0248] Reference Example 5: Synthesis of O-(4-(5-cyclopropylisoxazole-3-yl)benzyl)hydroxylamine hydrochloride.

[0249] Step 1: Synthesis of 2-((4-(5-cyclopropylisoxazole-3-yl)benzyl)oxy)isoindoline-1,3-dione.

[0250] A mixed solution of 1.08 g of 4-(5-cyclopropylisoxazole-3-yl)phenyl)methanol, 862 mg of N-hydroxyphthalimide, 1.39 g of triphenylphosphine, and 15 ml of tetrahydrofuran was mixed and 1.22 g of diisopropyl azodicarboxylic acid was added under ice cooling, and the mixture was stirred overnight at room temperature. After the reaction was complete, the solvent was removed under reduced pressure. 3 ml of ethanol was added to the resulting residue, and the precipitated solid was filtered to obtain 1.48 g of the target product as a white solid.

[0251] 1 H-NMR (CDCl3, Me4Si, 400MHz) δ: 7.83-7.72 (m, 6H), 7.64-7.59 (m, 2H), 6.22 (s, 1H), 5.22 (s, 2H), 2.13-2.04 (m, 1H), 1.13-0.99 (m, 4H).

[0252] Step 2: Synthesis of O-(4-(5-cyclopropylisoxazole-3-yl)benzyl)hydroxylamine hydrochloride.

[0253] 1.48 g of 2-((4-(5-cyclopropylisoxazole-3-yl)benzyl)oxy)isoindoline-1,3-dione and 15 ml of ethanol were mixed and 252 mg of hydrazine monohydrate was added under ice cooling, and the mixture was stirred overnight at room temperature. After the reaction was complete, 3 ml of toluene was added to the reaction mixture, and the ethanol was removed under reduced pressure. 3 ml of dichloromethane was added to the resulting residue, and the precipitated solid was filtered off. The solvent was removed from the obtained filtrate under reduced pressure, and 8 ml of diisopropyl ether was added. 4 ml of 4 mol / l hydrochloric acid-dioxane solution was added dropwise to the resulting mixed solution under ice cooling, and the mixture was stirred at the same temperature for 3 hours. After stirring, the precipitated solid was filtered off, and 890 mg of the target product was obtained as a white solid.

[0254] 1H-NMR (DMSO-d6, Me4Si, 400MHz) δ: 11.12 (br, 3H), 7.88-7.83 (m, 2H), 7.55-7.51 (m, 2H), 6.78 (s, 1H), 5.09 (s, 2H), 2.22-2.13 (m, 1H), 1.13-1.07 (m, 2H), 0.96-0.90 (m, 2H).

[0255] The compounds of the present invention can be synthesized in accordance with the above synthesis examples and reference examples. Examples of compounds of the present invention prepared in the same manner as in Synthesis Examples 1 and 2 are shown in Table 1, but the compounds of the present invention are not limited to these.

[0256] In the table, the substituent labeled "Me" represents "methyl," and similarly, "tBu" represents "tert-butyl," and "cPr" represents "cyclopropyl." The notation "*" indicates that the compound is an oily or resinous compound with no melting point, and "mp" represents the melting point (in °C).

[0257] Furthermore, in the table, for example, the "4-" in "4-Me-Ph" indicates the substitution position on the phenyl group, as described below. For example, "4-Me-Ph" represents 4-methylphenyl, and "2,6-F2-Ph" represents 2,6-difluorophenyl.

[0258] [ka]

[0259] Furthermore, the substituents represented by E-1a to E-10a each represent the following structures.

[0260] [ka]

[0261] [Table 1]

[0262] [ka]

[0263] ―――――――――――――――――――――――――――――――――― No. G Z 1 R X m.p.(℃) ―――――――――――――――――――――――――――――――――― 1-001 3-CF3-Ph E-3a tBu * 1-002 3-CF3-Ph 1-Me-(E-4a) tBu * 1-003 3-CF3-Ph 2-Me-(E-6a) tBu * 1-004 3-CF3-Ph 1-Me-(E-9a) tBu * 1-005 3-Me-Ph 1-Me-(E-4a) tBu 66-68 1-006 3-Me-Ph 2-Me-(E-6a) tBu * 1-007 3-Me-Ph 1-Me-(E-5a) tBu * 1-008 3-Me-Ph 2-Me-(E-8a) tBu * 1-009 3-Me-Ph 2-Me-(E-7a) tBu * 1-010 3-CF3-Ph 1-Me-(E-5a) tBu * 1-011 3-CF3-Ph 2-Me-(E-8a) tBu * 1-012 3-CF3-Ph 2-Me-(E-7a) tBu * 1-013 3-Me-Ph 1-Me-(E-9a) tBu * 1-014 3-Me-Ph 3-Me-(E-2a) tBu * 1-015 3-Me-Ph 5-cPr-(E-1a) tBu * 1-016 3-Me-Ph 3-Me-(E-3a) tBu * 1-017 3-Me-Ph 1-Me-(E-10a) tBu * ―――――――――――――――――――――――――――――――――― Among the compounds of the present invention shown in Table 1, compounds for which the melting point is not specified. 1 The H-NMR data is shown in Table 2. Note that the data below was measured in deuterated chloroform. "#1" indicates that the measurement was performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL), and similarly, "#2" indicates that the measurement was performed at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).

[0264] [Table 2] ------------------------------------------------------------------ No. 1 H-NMR (CDCl3, Me4Si) ------------------------------------------------------------------ 1-001(#1):δ 8.90 (br, 1H), 7.90-7.86 (m, 1H), 7.73-7.71 (m, 1H), 7.61 (d, J = 8.5 Hz, 2H), 7.41-7.34 (m, 4H), 7.24-7.22 (m, 1H), 7.14 (s, 1H), 7.10-7.05 (m, 1H), 6.48-6.46 (m, 1H), 4.96 (s, 2H), 1.73 (s, 9H). 1-002(#1):δ 8.87 (br, 1H), 7.71 (d, J = 8.2 Hz, 2H), 7.37-7.33 (m, 5H), 7.23-7.21 (m, 1H), 7.14-7.11 (m, 1H), 7.09-7.02 (m, 1H), 6.50 (d, J = 2.4 Hz, 1H), 4.94 (s, 2H), 3.95 (s, 3H), 1.72 (s, 9H). 1-003(#2):δ 8.89 (br, 1H), 7.79 (s, 1H), 7.63 (d, J = 8.4 Hz, 2H), 7.40-7.34 (m, 4H), 7.23-7.21 (m, 1H), 7.14 (s, 1H), 7.10-7.07 (m, 1H), 4.95 (s, 2H), 2.52 (s, 3H), 1.72 (s, 9H)。 1-004(#2):δ 9.16 (br, 1H), 7.92 (s, 1H), 7.64 (d, J = 8.4 Hz, 2H), 7.53-7.49 (m, 1H), 7.46-7.33 (m, 3H), 7.27-7.25 (m, 1H), 7.16-7.12 (m, 2H), 4.99 (s, 2H), 3.97 (s, 3H), 1.73 (s, 9H)。 1-006(#1):δ 9.05 (br, 1H), 7.78 (s, 1H), 7.65-7.60 (m, 2H), 7.40-7.36 (m, 2H), 7.17-7.10 (m, 2H), 6.91-6.87 (m, 1H), 6.75-6.71 (m, 2H), 4.94 (s, 2H), 2.52 (s, 3H), 2.29 (s, 3H), 1.73 (s, 9H)。 1-007(#1):δ 9.05 (br s, 1H), 7.72 (s, 1H), 7.58 (s, 1H), 7.38-7.33 (m, 4H), 7.17-7.10 (m, 2H), 6.92-6.87 (m, 1H), 6.75-6.72 (m, 2H), 4.92 (s, 2H), 3.95 (s, 3H), 2.28 (s, 3H), 1.73 (s, 9H)。 1-008(#1):δ 9.09 (br s, 1H), 7.75 (s, 1H), 7.42-7.35 (m, 4H), 7.19-7.12 (m, 2H), 6.92-6.88 (m, 1H), 6.75-6.72 (m, 2H), 4.94 (s, 2H), 2.73 (s, 3H), 2.28 (s, 3H), 1.72 (s, 9H)。 1-009(#1):δ 9.04 (br, 1H), 7.82-7.78 (m, 2H), 7.42-7.37 (m, 2H), 7.28 (s, 1H), 7.16-7.12 (m, 2H), 6.90-6.86 (m, 1H), 6.74-6.72 (m, 2H), 4.96 (s, 2H), 2.78 (s, 3H), 2.27 (s, 3H), 1.73 (s, 9H)。 1-010(#1):δ 8.94 (br, 1H), 7.69 (s, 1H), 7.58-7.52 (m, 2H), 7.48-7.29 (m, 8H), 7.24-7.22 (m, 1H), 7.16-7.14 (m, 1H), 7.11-7.06 (m, 1H), 4.92 (s, 2H), 3.94 (s, 3H), 1.74 (s, 9H)。 1-011(#1):δ 9.08 (br, 1H), 7.71-7.68 (m, 1H), 7.45-7.31 (m, 6H), 7.25-7.22 (m, 1H), 7.16-7.13 (m, 1H), 7.10-7.06 (m, 1H), 4.93 (s, 2H), 2.72 (s, 3H), 1.72 (s, 9H)。 1-012(#1):δ 8.85 (br s, 1H), 7.81-7.77 (m, 2H), 7.39-7.30 (m, 5H), 7.23-7.21 (m, 1H), 7.14-7.12 (m, 1H), 7.09-7.04 (m, 1H), 4.96 (s, 2H), 2.77 (s, 3H), 1.73 (s, 9H)。 1-013(#2):δ 9.52 (br, 1H), 7.92-7.89 (m, 1H), 7.64-7.58 (m, 2H), 7.53-7.49 (m, 2H), 7.21-7.14 (m, 1H), 7.12-7.10 (m, 1H), 6.93-6.89 (m, 1H), 6.80-6.74 (m, 2H), 4.99 (s, 2H), 3.95 (s, 3H), 2.29 (s, 3H), 1.72 (s, 9H)。 1-014(#1): δ 9.15 (broad, 1H), 7.67-7.63 (multiplet, 2H), 7.45-7.41 (multiplet, 2H), 7.19-7.07 (multiplet, 2H), 6.91-6.87 (multiplet, 1H), 6.73-6.71 (multiplet, 2H), 6.34 (singlet, 1H), 4.96 (singlet, 2H), 2.36 (singlet, 3H), 2.28 (singlet, 3H), 1.72 (singlet, 9H). 1-015(#1): δ 9.15 (broad, 1H), 7.70-7.65 (multiplet, 2H), 7.44-7.40 (multiplet, 2H), 7.17-7.10 (multiplet, 2H), 6.92-6.87 (multiplet, 1H), 6.74-6.71 (multiplet, 2H), 6.17 (singlet, 1H), 4.96 (singlet, 2H), 2.28 (singlet, 3H), 2.14-2.05 (multiplet, 1H), 1.72 (singlet, 9H), 1.15-0.98 (multiplet, 4H). 1-016(#1): δ 9.13 (broad, 1H), 7.76-7.75 (multiplet, 1H), 7.57-7.52 (multiplet, 2H), 7.42-7.37 (multiplet, 2H), 7.15-7.11 (multiplet, 2H), 6.90-6.86 (multiplet, 1H), 6.74-6.72 (multiplet, 2H), 6.25-6.23 (multiplet, 1H), 4.94 (singlet, 2H), 2.37 (singlet, 3H), 2.27 (singlet, 3H), 1.73 (singlet, 9H). 1-017(#2): δ 9.12 (broad, 1H), 8.07 (doublet, J = 8.1 Hz, 2H), 7.49 (doublet, J = 8.1 Hz, 2H), 7.17-7.11 (multiplet, 2H), 6.89-6.88 (multiplet, 1H), 6.77-6.72 (multiplet, 2H), 5.00 (singlet, 2H), 4.41 (singlet, 3H), 2.28 (singlet, 3H), 1.73 (singlet, 9H) ―――――――――――――――――――――――――――――――――― [Test Example] Next, the usefulness of the compounds of the present invention as pest control agents will be specifically explained in the following test examples, but the present invention is not limited to these. In the test examples, "RH" represents relative humidity, and for example, "humidity 100%RH" indicates that the relative humidity is 100%.

[0265] Preparation of test reagents Emulsions of the compound of the present invention were prepared at concentrations of 1% by mass, 5% by mass, and 20% by mass, respectively, in accordance with the emulsion formulation examples described above. These emulsions were used as test solutions in the following Test Examples 1 to 7.

[0266] Test Example 1: Test of the effectiveness of wheat rot control 90cm 3 Wheat (variety: Haruyutaka) was planted in plastic pots, and at the 1.3-leaf stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed onto the plants. One day after spraying, a conidial spore suspension of the wheat blight fungus (Septoria nodorum) was spray-inoculated onto the wheat plants, and they were placed in an inoculation box at 20°C and 100% RH for two days. After that, they were placed in an air-conditioned greenhouse (20°C, 80% RH) and kept there for eight days. The percentage of diseased leaves on the inoculated leaves was measured, and the control efficacy was calculated according to the following formula.

[0267] 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 efficacy of 70% or higher.

[0268] Compounds; No. 1-002, 1-003, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-014, 1-015, 1-016, 1-017.

[0269] Test Example 2: Efficacy Test for Controlling Powdery Mildew in Tomatoes 90cm 3Tomato plants (variety: Momotaro) were planted in plastic pots, and at the 2-leaf stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed on. After air drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and spray-inoculated with a conidial suspension of the tomato powdery mildew fungus (Leveillula taurica). After 14 days, the percentage of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0270] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0271] Compounds; 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, 1-014, 1-015, 1-016, 1-017.

[0272] Test Example 3: Efficacy Test for Controlling Gray Mold in Cucumbers 90cm 3 Cucumber plants (variety: Sagami Hanpaku) were planted in plastic pots. At the cotyledon stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed onto the plants and air-dried. The treated leaves were then cut off and placed in plastic containers. 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 this mixture was dropped onto each treated leaf. After inoculation, the plants were left at 20°C and high humidity (100% RH) for 3 days. Subsequently, the percentage of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0273] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0274] Compounds; 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.

[0275] Test Example 4: Efficacy Test for Controlling Cucumber Sclerotinia Disease 90cm 3 Cucumber plants (variety: Sagami Hanpaku) were planted in plastic pots, and at the cotyledon stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed on them and air-dried. The treated leaves were then placed in a plastic container. Agar pieces (5 mm in diameter) containing Sclerotinia sclerotiorum, which had been cultured in PDA medium beforehand, were inoculated onto the cotyledons of the fungicide-treated cucumbers. After inoculation, the plastic container was covered with plastic sheeting, humidified (100% RH), and left at 20°C for 2 days. The proportion of lesions formed on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0276] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0277] Compounds; 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.

[0278] Test Example 5: Cucumber Powdery Mildew Control Efficacy Test 90cm 3 Cucumbers (variety: Sagami Hanpaku) were planted in plastic pots, and at the cotyledon stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed onto the plants. After air drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and spray-inoculated with a conidial suspension of the cucumber powdery mildew fungus (Erysiphe polygoni). After 9 days, the percentage of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0279] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0280] Compounds; 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.

[0281] Test Example 6: Efficacy Test for Controlling Cucumber Anthracnose 90cm 3 Cucumbers (variety: Sagami Hanpaku) were planted in plastic pots, and at the cotyledon stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed onto the plants. One day after spraying, a conidial suspension of the cucumber anthracnose fungus (Colletotrichum lagenarium) was spray-inoculated onto the cucumbers, and they were placed in an inoculation box at 25°C and 100% RH for two days. After that, they were placed in an air-conditioned greenhouse (23°C, 60% RH) and kept there for seven days. The percentage of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0282] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0283] Compounds; 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.

[0284] Test Example 7: Soybean Rust Disease Control Efficacy Test 90cm 3 Soybeans (variety: Enrei) were planted in plastic pots, and at the single-leaf stage, 5 ml of a 500 ppm solution of the test fungicide was sprayed onto the plants. One day after spraying, a conidial suspension of the soybean rust fungus (Phakopsora pachyrhizi) was spray-inoculated onto the soybeans, and they were placed in an inoculation box at 20°C and 100% RH for two days. After that, they were placed in an air-conditioned greenhouse (20°C, 60% RH) and kept there for 10 days. The percentage of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0285] As a result, among the compounds tested, the following compounds showed a control efficacy of 70% or higher.

[0286] Compounds; No. 1-001, 1-004, 1-007, 1-008, 1-009, 1-012, 1-014, 1-015, 1-016. [Industrial applicability]

[0287] The pyrazole compound according to the present invention exhibits excellent pest control activity, particularly bactericidal activity, and is an extremely useful compound that has almost no adverse effects on non-target organisms such as mammals, fish, and beneficial insects.

Claims

1. Formula (1): 【Chemistry 1】 [In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula, 【Chemistry 2】 G １ represents hydroxy, nitro, cyano, a halogen atom, C １ to C ６ alkyl, C ３ to C １０ cycloalkyl, C １ to C ６ haloalkyl, C １ to C ６ alkoxy, C １ to C ６ haloalkoxy, C １ to C ６ alkylthio, C １ to C ６ alkylsulfinyl, C １ to C ６ alkylsulfonyl, di(C １ to C ６ alkyl)amino, C １ to C ６ alkylcarbonyl, C １ to C ６ alkoxycarbonyl, C １ to C ６ alkylaminocarbonyl, C ３ to C １０ cycloalkylaminocarbonyl or di(C １ to C ６ alkyl)aminocarbonyl, G １ In relation to this, if m5 represents an integer of 2, 3, 4, or 5, then each G １ They may be the same as each other, or they may be different from each other. R Ｘ C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, benzyl, R Ｘ -1, R Ｘ -2, R Ｘ -3 or R Ｘ -4 represents, R Ｘ -1 to R Ｘ -4 represents the structure shown in the following structural formulas, 【Transformation 3】 X １ C is a halogen atom. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ Represents alkoxy, X １ In relation to this, if u5 represents an integer of 2, 3, 4, or 5, then each X １ They may be the same as each other, or they may be different from each other. X １ In relation to this, if u4 represents an integer of 2, 3, or 4, then each X １ They may be the same as each other, or they may be different from each other. R Ｙ This represents a hydrogen atom or a halogen atom, R ２ is a hydrogen atom or C １ ~C ６ Represents alkyl, R ３ is a hydrogen atom or C １ ~C ６ Represents alkyl, Z １ This represents E-1 to E-8 or E-9, Z ２ C is a hydroxyl, carboxyl, amino, nitro, cyano, halogen atom. １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy or C １ ~C ６ Represents alkylthio, Z ２ In relation to this, if n4 represents an integer of 2, 3, or 4, then each Z ２ They may be the same as each other, or they may be different from each other. E-1 to E-10 represent structures represented by the following structural formulas, 【Chemistry 4】 Z ａ represents a halogen atom, C １ to C ６ alkyl, C ３ to C １０ cycloalkyl, C １ to C ６ haloalkyl, C １ to C ６ alkoxy, C １ to C ６ haloalkoxy or C １ to C ６ alkylthio, Z ａ In relation to this, if v3 represents an integer of 2 or 3, then each Z ａ They may be the same as each other, or they may be different from each other. Z ａ In relation to this, if v2 is an integer of 2, then each Z ａ They may be the same as each other, or they may be different from each other. Z ｂ represents C １ to C ６ alkyl, and m5 represents an integer of 0, 1, 2, 3, 4, or 5. n4 represents an integer of 0, 1, 2, 3, or 4. u5 represents an integer of 0, 1, 2, 3, 4, or 5. u4 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 or a salt thereof.

2. G １ C １ ~C ６ Alkyl or C １ ~C ６ Represents a haloalkyl group, R Ｘ C １ ~C ６ Represents alkyl, R Ｙ This represents a hydrogen atom, R ２ This represents a hydrogen atom, R ３ This represents a hydrogen atom, Z ａ C １ ~C ６ Alkyl or C ３ ~C １０ Represents cycloalkyl, m5 represents the integer 1, n4 represents an integer of 0, v3 represents an integer of 0 or 1. v2 represents an integer of 0 or 1, The pyrazole compound or salt thereof according to claim 1, wherein v1 represents an integer of 0.

3. A pesticide containing one or more pyrazole compounds and salts thereof selected from those described in any one of claims 1 and 2 as an active ingredient.

4. A bactericide containing one or more pyrazole compounds and salts thereof selected from those described in any one of claims 1 and 2 as an active ingredient.

5. A fungicide for agricultural and horticultural use, comprising one or more selected from the pyrazole compounds and salts thereof described in either claim 1 or 2 as an active ingredient.

6. An antifungal agent containing one or more pyrazole compounds and salts thereof selected from those described in any one of claims 1 and 2 as an active ingredient.

7. An internal parasite control agent containing one or more selected from the pyrazole compounds and salts thereof described in either claim 1 or 2 as an active ingredient.

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