Pyrazole compound and harmful organism control agent

Abstract

The present invention provides a pyrazole compound represented by formula (1) or a salt thereof, and a novel bactericide, particularly, a bactericide for agricultural and horticultural use, containing the compound as an active ingredient. The formula describes a structure in which: G represents G-1; G1 represents C1-C6 alkyl or the like; RX represents C1-C6 alkyl or the like; RY represents a hydrogen atom or the like; R1 represents a hydrogen atom or the like; R2 represents a hydrogen atom or the like; R3 represents a hydrogen atom or the like; R4 represents a hydrogen atom or the like, R5 represents a hydrogen atom or the like, Z1 represents E-1 or the like; Za represents C1-C6 alkyl or the like; Z2 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; p represents an integer of 0 or 1; and v2 represents an integer of 0, 1 or 2.

Description

Pyrazole compounds and pest control agents

[0001] The present invention relates to novel pyrazole compounds and salts thereof, and pesticides containing the compounds and salts thereof as active ingredients.

[0002] Patent Documents 1 and 2 disclose certain pyrazole compounds, but do not disclose anything about the pyrazole compounds of the present invention.

[0003] Furthermore, Patent Documents 3 and 4 disclose that certain pyrazole compounds are useful as fungicides, but do not disclose anything about the pyrazole compounds of the present invention.

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

[0005] International Publication No. WO 2002 / 085860, International Publication No. WO 2006 / 132197, International Publication No. WO 2009 / 028280, International Publication No. WO 1996 / 038419, International Publication No. WO 2020 / 109391, International Publication No. WO 2021 / 224220, International Publication No. WO 2021 / 228734, International Publication No. WO 2021 / 233861

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

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

[0008] The pyrazole compounds of the present invention have not been disclosed in any literature, and their usefulness as pest control agents is not known.

[0009] That is, the present invention relates to the following [1].

[0010] [1] Formula (1):

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

[0012] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R Ｘ is 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 represents −4, and R Ｘ-1 to R Ｘ -4 represents a structure represented by the following structural formula,

[0013] X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X １ In the above relationship, when u5 represents an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, １ In the relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-29 or E-30, and Z ２ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; Z ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, E-1 to E-30 each represent a structure represented by the following structural formula:

[0014] Z ａ is a hydroxyl, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, —C(═NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Z ａIn the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, ａ In the relationship, when v4 represents an integer of 2, 3 or 4, each Z ａ may be the same as or different from each other, ｂ is C １ ~C ６ represents alkyl, R ａ is hydroxy, cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylcarbonylamino, phenylcarbonylamino, -OR ｇ , -C(O)R ｇ , -NR ｈ SO ２ R ｊ or Q-1, wherein Q-1 represents a structure represented by the following structural formula:

[0015] Q １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, １ In the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Q １ may be the same as or different from each other, R ｂ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｄis amino, hydroxyamino, C １ ~C ６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ R represents (alkyl)amino, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy, R ｆ is a hydrogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkylsulfonyl or C １ ~C ６ represents haloalkylsulfonyl, R ｇ represents Q-1, and R ｈ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６m5 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, p represents an integer of 0 or 1, v4 represents an integer of 0, 1, 2, 3, or 4, v2 represents an integer of 0, 1, or 2, v1 represents an integer of 0 or 1, and w5 represents an integer of 0, 1, 2, 3, 4, or 5.

[0016] The compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogenic bacteria.

[0017] Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agricultural and horticultural use.

[0018] The present invention will be described in detail below.

[0019] The compounds of the present invention may exist as geometric isomers of E- and Z-forms depending on the types of substituents, and the compounds of the present invention include mixtures containing these E-, Z-, or E- and Z-forms in any ratio.

[0020] Furthermore, the compound of the present invention may have optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compound of the present invention includes all optically active forms or racemic forms.

[0021] Furthermore, the compounds of the present invention may have tautomers depending on the type of substituent, and the compounds of the present invention include all tautomers or mixtures of tautomers containing all tautomers in any ratio.

[0022] Furthermore, the compound of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, and the compound of the present invention encompasses all rotational isomers or a mixture of diastereomers containing all rotational isomers in any ratio.

[0023] Next, specific examples of each substituent shown in this specification are shown below, where n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.

[0024] As used herein, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" used herein also represents these halogen atoms.

[0025] In this specification, "C ａ ~C ｂ The term "alkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkyl" 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 from the range of carbon atoms specified.

[0026] In this specification, "C ａ ~C ｂ The term "haloalkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms, in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. ａ ~C ｂ Specific examples 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 ｂThe "haloalkyl" is selected from the range of carbon atoms specified.

[0027] In this specification, "C ａ ~C ｂ The term "alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon having a to b carbon atoms and one or more double bonds in the molecule. ａ ~C ｂ Specific examples of "alkenyl" include vinyl, 1-propenyl, 2-propenyl (hereinafter also referred to as allyl), 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl. ａ ~C ｂ "Alkenyl" is selected from the range of carbon atoms specified.

[0028] In this specification, "C ａ ~C ｂ The term "alkynyl" refers to a straight or branched chain unsaturated hydrocarbon having a to b carbon atoms and one or more triple bonds in the molecule. ａ ~C ｂ Specific examples of "alkynyl" include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl. ａ ~C ｂ "Alkynyl" is selected within the range of carbon atoms specified.

[0029] In this specification, "C ａ ~C ｂ The expression "alkoxy" represents alkyl-O- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific 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 from the range of carbon atoms specified.

[0030] In this specification, "C ａ ~C ｂ The expression "haloalkoxy" represents haloalkyl-O- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "haloalkoxy" 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 from the range of carbon atoms specified.

[0031] In this specification, "C ａ ~C ｂ The expression "alkylthio" represents alkyl-S- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylthio" include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio. ａ ~C ｂ The "alkylthio" is selected from the range of carbon atoms specified.

[0032] In this specification, "C ａ ~C ｂ The expression "haloalkylthio" represents haloalkyl-S- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "haloalkylthio" include difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, and 1,1,2,3,3,3-hexafluoropropylthio.ａ ~C ｂ The "haloalkylthio" is selected from the range of carbon atoms specified.

[0033] In this specification, "C ａ ~C ｂ The expression "alkylsulfinyl" represents alkyl-S(O)- having the above-mentioned meaning of a to b carbon atoms. Incidentally, -S(O)- can also be simply expressed as -SO-. ａ ~C ｂ Specific examples of "alkylsulfinyl" include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, and tert-butylsulfinyl. ａ ~C ｂ The "alkylsulfinyl" is selected from the range of carbon atoms specified.

[0034] In this specification, "C ａ ~C ｂ The expression "alkylsulfonyl" means alkyl-SO 3 having the above-mentioned meaning and containing a to b carbon atoms. ２ - represents "C ａ ~C ｂ Specific examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl. ａ ~C ｂ The "alkylsulfonyl" is selected from the specified range of carbon atoms.

[0035] In this specification, "C ａ ~C ｂ The notation "haloalkylsulfonyl" means a haloalkyl-SO having the above-mentioned meaning and containing a to b carbon atoms. ２ - represents "C ａ ~C ｂSpecific examples of "haloalkylsulfonyl" include difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trifluoroethylsulfonyl, and 1,1,2,3,3,3-hexafluoropropylsulfonyl. ａ ~C ｂ The "haloalkylsulfonyl" is selected from the specified range of carbon atoms.

[0036] In this specification, "C ａ ~C ｂ The term "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms. ａ ~C ｂ "Cycloalkyl" can form a single ring or multiple ring structures, for example, from 3 to 10 members. In addition, hydrogen atoms in each ring may be optionally replaced with alkyl atoms within the specified range of carbon atoms. ａ ~C ｂ Specific examples of "cycloalkyl" include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. ａ ~C ｂ The "cycloalkyl" is selected from the range of carbon atoms specified.

[0037] In this specification, "C ａ ~C ｂ The term "halocycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms. When substituted with two or more halogen atoms, the halogen atoms may be the same or different from each other. ａ ~C ｂSpecific examples of "halocycloalkyl" include 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, and 2,2,3,3-tetrafluorocyclobutyl. ａ ~C ｂ The "halocycloalkyl" is selected from the range of carbon atoms specified.

[0038] In this specification, "C ａ ~C ｂ The expression "alkylamino" refers to an amino in which one of the hydrogen atoms is substituted by an alkyl having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylamino" include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino. ａ ~C ｂ The "alkylamino" is selected from the specified range of carbon atoms.

[0039] In this specification, "C ａ ~C ｂ The expression "cycloalkylamino" refers to an amino in which one of the hydrogen atoms is substituted by a cycloalkyl having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "cycloalkylamino" include cyclopropylamino, cyclobutylamino, cyclopentylamino, and cyclohexylamino. ａ ~C ｂ The "cycloalkylamino" is selected from the range of carbon atoms specified.

[0040] In this specification, "di(C ａ ~C ｂThe expression "di(C alkyl)amino" refers to an amino in which both hydrogen atoms are substituted with alkyls having the above-mentioned meaning and containing a to b carbon atoms, each of which may be the same or different from each other. ａ ~C ｂ Specific examples of "di(C alkyl)amino" include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, and di(n-butyl)amino. ａ ~C ｂ Each alkyl in the "(alkyl)amino" is selected within the specified range of carbon atoms.

[0041] In this specification, "C ａ ~C ｂ The expression "alkylcarbonyl" represents alkyl-C(O)- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylcarbonyl" include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl. ａ ~C ｂ The "alkylcarbonyl" is selected from the specified range of carbon atoms.

[0042] In this specification, "C ａ ~C ｂ The expression "alkoxycarbonyl" represents alkyl-O-C(O)- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkoxycarbonyl" include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl. ａ ~C ｂ The "alkoxycarbonyl" is selected from the range of carbon atoms specified.

[0043] In this specification, "C ａ ~C ｂ The expression "alkylaminocarbonyl" refers to a carbamoyl in which one of the hydrogen atoms is substituted by an alkyl having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylaminocarbonyl" include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, and tert-butylcarbamoyl. ａ ~C ｂ The "alkylaminocarbonyl" is selected from the specified range of carbon atoms.

[0044] In this specification, "C ａ ~C ｂ The expression "cycloalkylaminocarbonyl" refers to a carbamoyl in which one of the hydrogen atoms is substituted by a cycloalkyl having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "cycloalkylaminocarbonyl" include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl. ａ ~C ｂ The "cycloalkylaminocarbonyl" is selected from the specified range of carbon atoms.

[0045] In this specification, "di(C ａ ~C ｂ The expression "di(C) alkylaminocarbonyl" refers to a carbamoyl in which both hydrogen atoms are substituted with alkyl having the above-mentioned meaning and containing a to b carbon atoms, each of which may be the same or different from each other. ａ ~C ｂ Specific examples of "di(C)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 in the "alkylaminocarbonyl" is selected within the range of carbon atoms specified.

[0046] In this specification, "C ａ ~C ｂ The expression "alkylcarbonyloxy" represents alkyl-C(O)O- having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylcarbonyloxy" include acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy, 2-methylbutanoyloxy, pivaloyloxy, hexanoyloxy, and heptanoyloxy. ａ ~C ｂ The "alkylcarbonyloxy" is selected from the range of carbon atoms specified.

[0047] In this specification, "C ａ ~C ｂ The expression "alkylcarbonylamino" represents alkyl-C(O)NH- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylcarbonylamino" include acetoxyamino, propionyloxyamino, butyryloxyamino, etc. ａ ~C ｂ The "alkylcarbonylamino" is selected from the range of carbon atoms specified.

[0048] The term "phenylcarbonylamino" used herein refers to C ６ H ５ represents —C(O)NH—.

[0049] The term "halosulfonyloxy" used herein means a halogen atom -SO ２ Specific examples of "halosulfonyloxy" include fluorosulfonyloxy and chlorosulfonyloxy.

[0050] In this specification, "C ａ ~Cｂ The expression "alkoxycarbonyloxy" represents alkoxy-C(O)O- having the above-mentioned meaning of a to b carbon atoms. ａ ~C ｂ Specific examples of "alkoxycarbonyloxy" include methoxycarbonyloxy and ethoxycarbonyloxy. ａ ~C ｂ The "alkoxycarbonyloxy" is selected from the range of carbon atoms specified.

[0051] In this specification, "C ａ ~C ｂ The expression "alkylsulfonyloxy" means an alkyl-SO 3 group having the above-mentioned meaning and containing a to b carbon atoms. ２ -O-. ａ ~C ｂ Specific examples of "alkylsulfonyloxy" include methanesulfonyloxy and ethanesulfonyloxy. ａ ~C ｂ The "alkylsulfonyloxy" is selected from the specified range of carbon atoms.

[0052] In this specification, "C ａ ~C ｂ The notation "haloalkylsulfonyloxy" means a haloalkyl-SO having the above-mentioned meaning and containing a to b carbon atoms. ２ -O-. ａ ~C ｂ Specific examples of "haloalkylsulfonyloxy" include trifluoromethanesulfonyloxy, chloromethylsulfonyloxy, etc. ａ ~C ｂ The "haloalkylsulfonyloxy" is selected from the specified range of carbon atoms.

[0053] The term "aryl" as used herein refers to an aromatic ring having 6 to 10 carbon atoms. Specific examples include phenyl, α-naphthyl, and β-naphthyl, with phenyl being preferred. The aryl may be substituted with 1 to 3 halogen atoms, alkyl, alkoxy, cyano, nitro, or the like.

[0054] The expression "arylsulfonyloxy" in this specification means aryl-SO ２ Specific examples of "arylsulfonyloxy" include phenylsulfonyloxy and paratoluenesulfonyloxy.

[0055] The term "hydroxyamino" as used herein refers to HO-NH-.

[0056] The designation "thiol" herein refers to HS-.

[0057] In this specification, "R ａ C substituted with ａ ~C ｂ The notation "alkyl" means that any hydrogen atom attached to a carbon atom of the alkyl is bonded to one or more substituents R ａ The substituent R represents an alkyl having the above-mentioned meaning and having a to b carbon atoms, which is partially or completely substituted with: ａ When two or more groups are present, the substituent R ａ may be the same or different from each other.

[0058] The term "benzyl" used herein means -CH ２ C ６ H ５ Represents.

[0059] Next, a method for producing the compound of the present invention represented by formula (1) will be described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. Note that the following explanation is merely illustrative, and the compound of the present invention represented by formula (1) may also be produced by other methods. Hereinafter, "the compound of the present invention represented by formula (1)" will also be described as "compound (1)", and "the compound represented by formula (2)" will also be described as "compound (2)". Other compounds will also be described in a similar manner.

[0060] (Preparation Example 1) Compound (1) of the present invention can be prepared, for example, by the following preparation method.

[0061] [In the formula, J１ is a chlorine atom, a bromine atom, C １ ~C ４ Alkylcarbonyloxy or C １ ~C ４ alkoxycarbonyloxy (e.g., methoxycarbonyloxy), and G and R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z １ , Z ２ , n4 and p have the same meanings as above.] Compound (1) can be produced by reacting compound (2), compound (3) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), and a dehydration condensation agent in a solvent or without a solvent, and optionally in the presence of either a base or an additive, or both.

[0062] Alternatively, compound (1) can also be produced by reacting compound (2-1) with compound (3) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of a base or an additive, or both.

[0063] The amounts of the compound (3) or a salt thereof and the dehydration condensation agent used may be 0.5 to 50 equivalents per equivalent of the compound (2) or compound (2-1).

[0064] Some of the compounds represented by compound (3) are known compounds and are commercially available. In addition, other compounds represented by compound (3) can also be produced according to general synthetic methods for known compounds described in the literature.

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

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

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

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

[0069] The reaction temperature can be set at any temperature between −78° C. and the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reactant or the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0070] (Preparation Example 2) The compound (1-1) of the present invention can be prepared, for example, by the following preparation method.

[0071] [In the formula, Z ａ１ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl, and G and R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-1) can be produced by reacting compound (2-4) in a solvent or without a solvent, and optionally in the presence of a base.

[0072] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0073] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-4).

[0074] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0075] (Preparation Example 3) The compound (1-3) of the present invention can be prepared, for example, by the following preparation method.

[0076] [In the formula, G, J １ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (1-3) can be produced by reacting compound (2-6) with compound (D1) or compound (E1) in a solvent or without a solvent, and optionally in the presence of a base.

[0077] The amount of compound (D1) or compound (E1) used may be 0.5 to 50 equivalents per equivalent of compound (2-6).

[0078] Some of the compounds represented by compound (D1) are known compounds and are commercially available. Other compounds represented by compound (D1) can also be produced according to general synthetic methods for known compounds described in the literature.

[0079] Some of the compounds represented by compound (E1) are known compounds and are commercially available. Other compounds represented by compound (E1) can also be produced according to general synthetic methods for known compounds described in the literature.

[0080] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0081] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-6).

[0082] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0083] (Preparation Example 4) The compound (1-4) of the present invention can be prepared, for example, by the following preparation method.

[0084] [wherein L is a chlorine atom, a bromine atom, an iodine atom, C １ ~C ４ Alkyl sulfonyloxy (e.g., methanesulfonyloxy, etc.), halosulfonyloxy (e.g., fluorosulfonyloxy, etc.), C １ ~C ４ represents a leaving group such as haloalkylsulfonyloxy (e.g., trifluoromethanesulfonyloxy) or arylsulfonyloxy (e.g., paratoluenesulfonyloxy), and Z ａ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, and G and R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , Z ａ１ , n4 and p have the same meanings as above.

[0085] The compound (1-4) can be produced by reacting the compound (2-7) with the compound (C) in a solvent or without a solvent, and optionally in the presence of a base.

[0086] The amount of compound (C) used may be 0.5 to 50 equivalents per equivalent of compound (2-7).

[0087] Some of the compounds represented by compound (C) are known compounds and are commercially available. Other compounds represented by compound (C) can also be produced according to general synthetic methods for known compounds described in the literature.

[0088] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0089] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-7).

[0090] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0091] (Preparation Example 5) The compound (1-5) of the present invention can be prepared, for example, by the following preparation method.

[0092] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (1-5) can be produced by reacting compound (2-8) with a dehydrating agent in a solvent or without a solvent.

[0093] The amount of the dehydrating agent used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-8).

[0094] The dehydrating agent includes, for example, methyl N-(triethylammoniosulfonyl)carbamate.

[0095] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0096] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0097] (Preparation Example 6) The compound (1-6) of the present invention can be prepared, for example, by the following preparation method.

[0098] [In the formula, A represents an oxygen atom or a sulfur atom, G and R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-6) can be produced by reacting compound (2-6) with 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole in a solvent or without a solvent, and optionally in the presence of a base.

[0099] The amount of 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole used may be 0.5 to 50 equivalents per equivalent of compound (2-6).

[0100] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0101] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-6).

[0102] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0103] (Preparation Example 7) The compound (1-7) of the present invention can be prepared, for example, by the following preparation method.

[0104] [In the formula, R １０２ is C １ ~C ６ Alkyl or C １ ~C ６ A, G, L, and R represent haloalkyl. Ｘ , R Ｙ , R１ , R ２ , R ３ , R ４ , R ５ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-7) can be produced by reacting compound (1-6) of the present invention with compound (F) in a solvent or without a solvent, and optionally in the presence of a base.

[0105] The amount of compound (F) used may be 0.5 to 50 equivalents per equivalent of compound (1-6).

[0106] Some of the compounds represented by compound (F) are known compounds and are commercially available. Other compounds represented by compound (F) can also be produced according to general synthetic methods for known compounds described in the literature.

[0107] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0108] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-6).

[0109] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0110] (Preparation Example 8) The compound (1-9) of the present invention can be prepared, for example, by the following preparation method.

[0111] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , R ｄ , Z ２, n4 and p have the same meanings as defined above.] Compound (1-9) can be produced by reacting compound (1-8) with compound (K) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base, in accordance with a known method described in the literature, for example, the method described in Synthesis 2019, Vol. 51, pages 530-537, etc.

[0112] The amount of compound (K) used may be 0.5 to 50 equivalents per equivalent of compound (1-8).

[0113] Some of the compounds represented by compound (K) are known compounds and are commercially available. In addition, other compounds represented by compound (K) can also be produced according to general synthetic methods for known compounds described in the literature.

[0114] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0115] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-8).

[0116] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0117] The compound (1-8) of the present invention can be synthesized according to the method of Production Example 3.

[0118] (Preparation Example 9) The compound (1-11) of the present invention can be prepared, for example, by the following preparation method.

[0119] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , R １０２ , R ｅ , Rｆ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-11) can be produced by reacting compound (2-9) with compound (L) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.

[0120] The amount of compound (L) used may be 0.5 to 50 equivalents per equivalent of compound (2-9).

[0121] Some of the compounds represented by compound (L) are known compounds and are commercially available. Other compounds represented by compound (L) can also be produced according to general synthetic methods for known compounds described in the literature.

[0122] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0123] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-9).

[0124] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0125] Compound (2) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 1.

[0126] [Reaction Scheme 1]

[0127] [wherein X represents a halogen atom, G and R Ｘ and R Ｙhas the same meaning as above.] Compound (2) can be obtained by reacting compound (2-A) with compound (A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, compound (2) can be obtained by reacting compound (2-A) with compound (A) in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand.

[0128] Some of the compounds represented by compound (2-A) are known compounds and are commercially available. Other compounds represented by compound (2-A) can also be produced according to general synthetic methods for known compounds described in the literature.

[0129] The amount of compound (A) used may be 0.5 to 50 equivalents per equivalent of compound (2-A).

[0130] Some of the compounds represented by compound (A) are known compounds and are commercially available. Other compounds represented by compound (A) can also be produced according to general synthetic methods for known compounds described in the literature.

[0131] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0132] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-A).

[0133] The reaction can be carried out in the presence of a copper catalyst. Examples of copper catalysts that can be used include copper (monovalent) iodide, copper (monovalent) trifluoromethanesulfonate benzene complex, and copper (monovalent) trifluoromethanesulfonate toluene complex. The amount of the copper catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2-A).

[0134] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include N,N-dimethylglycine and 4-(dimethylamino)pyridine. The amount of the additive used can be 0.001 to 100 equivalents relative to 1 equivalent of compound (2-A).

[0135] The reaction can be carried out in the presence of a palladium catalyst. Examples of the palladium catalyst that can be used include palladium (divalent) (π-cinnamyl) chloride (dimer) and allylpalladium (divalent) chloride (dimer). The amount of the palladium catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2-A).

[0136] The reaction can be carried out in the presence of a ligand. Examples of the ligand that can be used include 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyl-di-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), and 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos). The amount of the ligand used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2-A).

[0137] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0138] The compound (2-1) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 2.

[0139] [Reaction Scheme 2]

[0140] [J １ , G.R. Ｘ , and R Ｙhas the same meaning as above.] Compound (2-1) can be obtained by reacting compound (2) with a halogenating agent such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride in accordance with a known method described in the literature, for example, the method described in Journal of Medicinal Chemistry [J. Med. Chem.] 1991, Vol. 34, p. 1630, etc.

[0141] Alternatively, it can be obtained by reacting with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, if necessary in the presence of a base, in accordance with the method described in Tetrahedron Lett., 2003, vol. 44, p. 4819, and J. Med. Chem., 1991, vol. 34, p. 222, or the like.

[0142] In compound (2), R Ｙ The compound (2-2) in which is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.

[0143] [Reaction Scheme 3]

[0144] [In the formula, R １０１ is C １ ~C ６ represents alkyl, and G and R Ｘ has the same meaning as above.] Step 1: Compound (2-C) can be obtained by reacting compound (2-B) with compound (B) or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, and optionally in the presence of a base.

[0145] Some of the compounds represented by compound (B) are known compounds and are commercially available. Other compounds represented by compound (B) can also be produced according to general synthetic methods for known compounds described in the literature.

[0146] The amount of compound (B) or a salt thereof used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-B).

[0147] Some of the compounds represented by compound (2-B) are known compounds described in Bioorganic & Medicinal Chemistry Letters, 2015, vol. 25, p. 4481, and other compounds represented by compound (2-B) can also be synthesized in the same manner as known compounds according to the method described in the literature.

[0148] When a solvent is used, the solvent to be used may be any solvent as long as it is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0149] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-B).

[0150] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0151] Step 2: Compound (2-2) can be obtained by reacting compound (2-C) with an oxidizing agent in a solvent or without a solvent.

[0152] Examples of the oxidizing agent that can be used include potassium permanganate, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-C).

[0153] When a solvent is used, the solvent to be used may be any solvent as long as it is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0154] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0155] In compound (2), R Ｙ The compound (2-2) in which is a hydrogen atom can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.

[0156] [Reaction Scheme 4]

[0157] [Wherein G and R Ｘ has the same meaning as above.] Step 1: Compound (2-E) can be obtained by reacting compound (2-D) with compound (B) under the same conditions as in step 1 in Reaction Scheme 3.

[0158] Some of the compounds represented by compound (2-D) are known compounds described in WO 2003 / 016275, and other compounds represented by compound (2-D) can also be synthesized in the same manner as known compounds according to the method described in the document.

[0159] Step 2: Compound (2-2) can be obtained by reacting compound (2-E) with carbon dioxide in the presence of a base, with or without a solvent.

[0160] The base that can be used includes, for example, n-butyllithium, etc. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-E).

[0161] When a solvent is used, the solvent to be used may be any solvent as long as it is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0162] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0163] The compound (2-4) used in Production Example 2 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 5.

[0164] [Reaction Scheme 5]

[0165] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , R １０１ , Z ２ , Z ａ１, n4 and p are as defined above.] Step 1: Compound (2-12) can be obtained by reacting compound (2) or compound (2-1) with compound (3-1) under the same conditions as in Production Example 1.

[0166] Some of the compounds represented by compound (3-1) are known compounds and are commercially available. Other compounds represented by compound (3-1) can also be produced according to general synthetic methods for known compounds described in the literature.

[0167] Step 2: Compound (2-3) can be obtained by reacting compound (2-12) according to a known method known in the literature, for example, the method described in The Journal of Organic Chemistry, 2006, Vol. 24, pages 9045-9050.

[0168] Step 3: Compound (2-4) can be obtained by reacting compound (2-3) with compound (H) according to a known method described in the literature, for example, the method described in WO 2008 / 156721.

[0169] Some of the compounds (H) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0170] The compound (2-6) used in Production Example 3 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 6.

[0171] [Reaction Scheme 6]

[0172] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２, n4 and p are as defined above.] Step 1: Compound (2-5) can be obtained by reacting compound (2) or compound (2-1) with compound (3-2) under the same conditions as in Production Example 1.

[0173] Some of the compounds represented by compound (3-2) are known compounds and are commercially available. Other compounds represented by compound (3-2) can also be produced according to general synthetic methods for known compounds described in the literature.

[0174] Step 2: Compound (2-6) can be obtained by reacting compound (2-5) according to a known method known in the literature, for example, the method described in WO 2009 / 082398.

[0175] The compound (2-7) used in Production Example 4 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 7.

[0176] [Reaction Scheme 7]

[0177] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , Z ２ , n4 and p have the same meanings as defined above.] Compound (2-7) can be obtained by reacting compound (2-5) according to a known method known in the literature, for example, the method described in WO 2011 / 109799.

[0178] The compound (2-8) used in Production Example 5 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 8.

[0179] [Reaction Scheme 8]

[0180] [In the formula, G, R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R５ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (2-8) can be obtained by reacting compound (2-3) with compound (J) according to a known method known in the literature, for example, the method described in WO 2008 / 016123.

[0181] Some of the compounds (J) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0182] The compound (2-C) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.

[0183] [Reaction Scheme 9]

[0184] [In the formula, G, R Ｘ and R １０１ has the same meaning as defined above.] Step 1: Compound (2-F) can be obtained by hydrolyzing compound (2-B) in the presence of water and an acid.

[0185] Examples of the acid that can be used include hydrochloric acid, acetic acid, etc. The amount of the acid used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-B).

[0186] When a solvent is used, the solvent to be used may be any solvent as long as it is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0187] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0188] Step 2: Compound (2-C) can be obtained by reacting compound (2-F) with compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) under the same conditions as in step 1 in reaction scheme 2.

[0189] The compound (2-9) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme.

[0190] [Reaction Scheme 10]

[0191] [G,R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ５ , R １０２ , Z ２ , n4 and p have the same meanings as defined above.] Compound (2-9) can be produced by reacting compound (1-10) of the present invention with an oxidizing agent in a solvent or without a solvent.

[0192] Examples of the oxidizing agent that can be used include hydrogen peroxide, metachloroperbenzoic acid, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-10).

[0193] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0194] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0195] The compound (1-10) of the present invention can be synthesized according to the method of Production Example 7.

[0196] The compound (2-11) can be produced, for example, according to the production route shown in the following reaction scheme 11.

[0197] [Reaction Scheme 11]

[0198] [In the formula, R １０３ is a hydrogen atom or C １ ~C ６ represents alkyl, G １ａ is C １ ~C ６ Alkyl or C ３ ~C ６ represents cycloalkyl; L, X, and RＸ , R Ｙ and R １０１ has the same meaning as defined above.] Step 1: Compound (2-G) can be obtained by reacting compound (2-10) with compound (F1) in the presence of a base, in a solvent or without a solvent.

[0199] Some of the compounds (F1) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0200] The amount of compound (F1) used may be 0.5 to 50 equivalents per equivalent of compound (2-10).

[0201] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0202] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-10).

[0203] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0204] The compound (2-10) can be synthesized according to the method of Reaction Scheme 1.

[0205] Step 2: Compound (2-H) can be obtained by reacting compound (2-G) with compound (G) in a solvent or without a solvent, in the presence of a base, and, if necessary, in the presence of a palladium catalyst and a ligand.

[0206] Some of the compounds (G) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0207] The amount of compound (G) used may be 0.5 to 50 equivalents per equivalent of compound (2-G).

[0208] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0209] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-G).

[0210] Examples of the palladium catalyst that can be used in the reaction include the palladium catalysts exemplified in Reaction Scheme 1. The amount of the palladium catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2-G).

[0211] Examples of the ligand that can be used in the reaction include the ligands exemplified in Reaction Scheme 1. The amount of the ligand used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (2-G).

[0212] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0213] Step 3: Compound (2-11) can be obtained by reacting compound (2-H) in a solvent or without a solvent, optionally in the presence of a base.

[0214] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-H).

[0215] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0216] The compound (2-N) can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 12.

[0217] [Reaction Scheme 12]

[0218] [In the formula, R １０４ Haji (C １ ~C ６ G and J represent (alkyl)amino, pyrrolidin-1-yl, piperidin-1-yl, or morpholin-1-yl; １ , R Ｘ and R １０１has the same meaning as defined above.] Step 1: Compound (2-K) can be obtained by hydrolyzing compound (2-J) in the presence of an acid, in a solvent or without a solvent.

[0219] Some of the compounds represented by compound (2-J) are known compounds and are commercially available. Other compounds represented by compound (2-J) can also be produced according to general synthetic methods for known compounds described in the literature.

[0220] Examples of the acid that can be used include hydrochloric acid, acetic acid, formic acid, sulfuric acid, etc. The amount of the acid used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-J).

[0221] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0222] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0223] Step 2: Compound (2-L) can be obtained by reacting compound (2-K) with compound (K1) in a solvent or without a solvent.

[0224] Some of the compounds represented by compound (K1) are known compounds and are commercially available. In addition, other compounds represented by compound (K1) can also be produced according to general synthetic methods for known compounds described in the literature.

[0225] The amount of compound (K1) used may be 0.5 to 50 equivalents per equivalent of compound (2-K).

[0226] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0227] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0228] Step 3: Compound (2-M) can be obtained by reacting compound (2-L) with compound (M) in the presence of a base in a solvent or without a solvent.

[0229] Some of the compounds represented by compound (M) are known compounds and are commercially available. Other compounds represented by compound (M) can also be produced according to general synthetic methods for known compounds described in the literature.

[0230] The amount of compound (M) used may be 0.5 to 50 equivalents per equivalent of compound (2-L).

[0231] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0232] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-L).

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

[0234] Step 4: Compound (2-N) can be obtained by reacting compound (2-M) with compound (B) or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of an acid.

[0235] The amount of compound (B) or a salt thereof used may be 0.5 to 50 equivalents per equivalent of compound (2-M).

[0236] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0237] Examples of the acid that can be used in the reaction include the acids exemplified in Step 1 of Reaction Scheme 12. The amount of the base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-M).

[0238] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0239] The compounds of the present invention can generally be used as agricultural and horticultural bactericides and fungicides against various diseases caused by Phytophthora, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Fungi Imperfecti, bacteria or viruses.

[0240] The term "pathogenic fungus" refers to a microorganism that causes a plant disease, and specific examples thereof include, but are not limited to, the following microorganisms: Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. (e.g. Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g. Cladosporium colocasiae, C. cucumerinum, C. variabile etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii, etc.), Mycosphaerella spp. (e.g., Mycosphaerella arachidis, M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis, etc.), Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii, etc.), Paracercospora spp. (e.g., Paracercospora egenula, etc.), Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g., Pseudocercospora abelmoschi, P. fuligena, P. vitis, etc.), Pseudocercosporella spp.(e.g., Pseudocercosporella capsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C.verruculosa spp., Drechslera spp., Pleospora spp., Pleospora herbarum spp., Pyrenophora spp. teres (Setosphaeria spp.) Setosphaeria turcica (Setosphaeria turcica) Stemphylium spp. lycopersici、S. solani、S. vesicarium spp., Venturia spp., Venturia carpophila, V. vesicarium spp. Inaequalis、V. nashicola、V. pyrin activity) and Didymella spp. fabae, Hendersonia spp., Phoma spp., Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae active) Pyrenochaeta spp spp. Botryosphaeria berengeriana f. sp. piricola、B. dothidea activity) Dothiorella spp. Fusicoccum spp. Guignardia spp. Lasiodiplodia spp spp. Phyllosticta spp.(also) Phyllosticta zingiberis spp.(also) Schizothyrium pomi spp.Acrospermum spp.Leptosphaerulina spp.Aspergillus spp., Penicillium spp.(from Penicillium digitatum, P. italicum、P. sclerotigenum spp., Trichophyton spp., Trichophyton mentagrophytes. rubrum spp., Histoplasma spp., Blumeria spp., Blumeria graminis f. sp. hordei、B. gf sp. tritici), Erysiphe spp. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. low activity) Golovinomyces spp. latisporus spp., Leveillula spp., Leveillula taurica spp., Microsphaera spp., Oidium spp., Oidium neolycopersici spp., Phyllactinia spp.(Phyllactinia kakicola)P. mali、P. moricola, Podosphaera spp., Podosphaera fusca, P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii activity) and Sphaerotheca spp. aphanis、S. fuliginea agent) and Uncinula spp. n. var. necator agent) (Uncinuliella spp.) Uncinuliella simulans var. simulans、U.S. s. var. tandae spp., Blumeriella jaapii spp., Cylindrosporium spp., Diplocarpon spp. mespili、D.rosae spp., Gloeosporium spp., Gloeosporium minus spp., Marssonina spp., Tapesia spp. yallundae, Lachnum spp., Scleromitrula spp., Botryotinia spp. byssoidea、B. cinerea、B. elliptic、B. fabae、B. squamosa agent) Ciborinia spp. Grovesinia spp. Monilia mumecola Monilinia spp. fructigena、M. laxa、M. mali、M. vaccinii-corymbosiactivity), Sclerotinia spp. homoeocarp、S. minor、S. sclerotiorum spp., Valdensia heterodoxa spp., Claviceps spp. sorghicola agent) Epichloe spp. Ephelis japonica Villosiclava virens Hypomyces spp. sp. mori、H. sf sp. low activity) Trichoderma spp.(also) Trichoderma viride activity) Calonectria spp.(an activity) Candelospora spp spp., Cylindrocladium spp., Fusarium spp. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. of sp.adzukicola, F. of sp. allii, F. of sp. asparagi, F. of sp. batatas, F. o. f. sp. cepae, 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. (e.g., Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (e.g., Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g., Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp.(including Thielaviopsis basicola) and Adisciso spp. Monochaetia spp. (including Pestalotia eriobotrifolia spp.) in Pestalotiopsis spp.(Pestalotiopsis funerea) P. longiseta、P. neglecta、P. theae, Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp nivalis spp., Ophiostoma spp., Cryphonectria spp., Cryphonectria parasitica spp., Diaporthe spp. kyushuensis、D. nomurai、D. tanakae, Diaporthopsis spp., Phomopsis spp. fukushii、P. obscurans、P. vexans , Cryptosporella spp , Discula spp , Discula theae-sinensis , Gnomonia spp , Coniella spp , Coryneum spp , Greeneria spp , Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp.(also, Valsa ceratosperma activity) Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp.(such as Gaeumannomyces graminis) Magnaporthe spp.(such as Magnaporthe grisea) Pyricularia spp.(such as Pyricularia zingiberis (Monilochaetes infuscans), Colletotrichum spp.(e.g., Colletotrichum acutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C. lindemuthianum, C. nigrum, C. orbiculare, C. spinaciae, etc.), Glomerella spp. (e.g., Glomerella cingulata, etc.), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora Ascomycota fungi such as Phialophora gregata, Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium 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.), Cronartium spp., Phakopsora spp. (e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.), Physopella spp. (e.g., Physopella ampelopsidis, etc.), Kuehneola spp.(e.g., Kuehneola japonica, etc.), Phragmidium spp. (e.g., Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, etc.), Gymnosporangium spp. (e.g., Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (e.g., Puccinia allii, P. brachypodii var. poae-nemoralis, P. coronata, P. c. var. coronata, P. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tanaceti, P. tokyensis, P. zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (e.g., Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (e.g., Blastospora smilacis, etc.), Uredo spp., Sphacelotheca spp., Urocystis spp., Sporisorium spp. (e.g., Sporisorium scitamineum, etc.), Ustilago spp. (e.g., Ustilago maydis, U. nuda, etc.), Entyloma spp., Exobasidium spp. (e.g., Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. (e.g., Tilletia caries, T.controversa, T. laevis, etc.), Itersonilia spp. (e.g., Itersonilia perplexans, etc.), Cryptococcus spp., Bovista spp. (e.g., Bovista dermoxantha, etc.), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum, etc.), Conocybe spp. (e.g., Conocybe apala, etc.), Marasmius spp. (e.g., Marasmius oreades, etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda, etc.), Sclerotium spp. (e.g., Sclerotium cepivorum, etc.), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis, etc.), Athelia spp. (e.g., Athelia Fungi of the phylum Basidiomycota such as Ceratobasidium spp. (e.g., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia spp. (e.g., Rhizoctonia solani, etc.), Thanatephorus spp. (e.g., Thanatephorus cucumeris, etc.), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp.; fungi of the phylum Chitridiomycota such as Olpidium spp.; and fungi of the phylum Blastocladiomycota such as Physoderma spp. Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R.Fungi of the subphylum Mucoromycotina such as stolonifer var. stolonifer, etc. Protists of the phylum Cercozoa such as Plasmodiophora spp. (e.g., Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (e.g., Peronospora alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (e.g., Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (e.g., Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (e.g., Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (e.g., Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. 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. sulcatum, P. sylvaticum, P. ultimum var. ultimum, P. vanterpoolii, P. Oomycetes of the phylum Heterokontophyta, such as P. vexans, P. volutum, etc. Gram-positive bacteria of the Actinobacteria phylum, such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli), and Streptomyces spp. (e.g., Streptomyces ipomoeae). Gram-positive bacteria of the Firmicutes phylum, such as Clostridium sp. Gram-positive bacteria of the Tenericutes phylum, such as Phytoplasma. Rhizobium spp. (e.g., Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g., Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g., Acidovorax avenae subsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. (e.g., Xanthomonas albilineans, X. arboricola pv. pruni, X. axonopodis pv. vitians, X.campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv. mangiferaeindicae, X. c. pv. nigromaculans, X. c. pv. pv. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s. pv. spinaciae, P. s. pv. syringae, P. s. pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. Gram-negative fungi of the phylum Proteobacteria, such as Erwinia spp. (e.g., Erwinia amylovora, E. rhapontici, etc.), Pantoea spp., Pectobacterium spp. (e.g., Pectobacterium atrosepticum, P. carotovorum, P. wasabiae, etc.). .

[0241] Specific examples of plant diseases caused by infection and proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases:

[0242] Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), sugar beet leaf spot (Cercospora beticola), bell pepper leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown leaf spot (Mycosphaerella arachidis), cherry brown hole (Cylindrosporium cerasella, Blumeriella jaapii), black sigatoka disease (Mycosphaerella fijiensis), yellow sigatoka disease (Mycosphaerella musicola), Speckled leaf blotch of wheat (Mycosphaerella graminicola), Circular leaf spot of persimmon (Mycosphaerella nawae), Mycosphaerella blight of pea (Mycosphaerella pinodes), Leaf spot of ginger (Mycosphaerella zingiberis), Leaf mold of tomato (Mycovellosiella fulva), Leaf mold of eggplant (Mycovellosiella nattrassii), Leaf mold of tomato (Cercospora fuligena), Isariopsis leaf spot of grapevine (Pseudocercospora vitis), Leaf spot of Chinese cabbage (Pseudocercosporella capsellae), Leaf spot of chrysanthemum (Septoriachrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape anthracnose (Elsinoe ampelina), Araliae scab anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta pisi), Cucumber leaf spot (Corynespora cassiicola), Rose stem canker (Leptosphaeria coniothyrium), Wheat glume blotch (Leptosphaeria nodorum), Rose leaf spot (Alternaria alternata), Cabbage leaf spot (Alternaria brassicae), Carrot leaf blight (Alternaria dauci), Pear black spot (Alternaria kikuchiana), Alternaria blotch (Alternaria mali) on apple, Alternaria leaf spot (Alternaria porri) on leek, Target spot (Bipolaris sorghicola) on sorghum, Southern leaf blight (Cochliobolus heterostrophus) on corn, Brown spot (Cochliobolus miyabeanus) on rice, Tip blight (Pleospora herbarum) on garlic, Stripe leaf blight (Pyrenophora graminea) on barley, Net blotch (Pyrenophora teres) on barley, Leaf blight (Setosphaeria turcica) on sorghum, Northern leaf blight (Setosphaeria turcica) on corn, Leaf spot (Stemphylium erythrorhizae) on asparagusbotryosum), Scab of Rosaceae (Prunus subfamily) (Venturia carpophila), Scab of apple (Venturia inaequalis), Scab of pear (Venturia nashicola), Gummy stem blight of Cucurbitaceae (Didymella bryoniae), Leaf spot of burdock (Phoma exigua var. exigua), Streak of wasabi (Phoma wasabiae), Ring rot of Rosaceae (Prunus subfamily) (Botryosphaeria berengeriana f. sp. piricola), Soft rot of kiwifruit (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Common green mold of citrus (Penicillium digitatum), Blue mold of citrus (Penicillium italicum), powdery mildew that occurs on various crops, 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.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter gourd powdery mildew (Oidium sp.), persimmon powdery mildew (Phyllactiniakakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha), rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), zucchini and melon powdery mildew (Podosphaera xanthii), strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), watermelon and melon powdery mildew (Sphaerotheca fuliginea), grape powdery mildew (Uncinula necator, U. n. var. necator), apple blotch (Diplocarpon mali), rose black spot (Diplocarpon rosae), onion gray mold neck rot (Botrytis allii), gray mold, Botrytis Blight (Botrytis cinerea), leaf blight of Chinese chives (Botrytis cinerea, B. byssoidea, B. squamosa), chocolate spot of broad beans (Botrytis cinerea, B. elliptica, B. fabae), brown rot of Rosaceae (Monilinia fructicola, M. fructigena, M. laxa), blossom blight of apples (Monilinia mali), dollar spot of shiba (Sclerotinia homoeocarpa), cottony rot, stem rot (Sclerotinia sclerotiorum), false smut of rice (Villosiclava virens), root necrosis of soybeans (Calonectria ilicicola), Fusarium blight of wheat (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae,Monographella nivalis), Fusarium blight (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of taro (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), Fusarium wilt of adzuki bean (Fusarium oxysporum f. sp. adzukicola), Fusarium basal rot of Chinese chive (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem rot of sweet potato (Fusarium oxysporum f. sp. batatas, F. solani), Dry rot of taro (Fusarium oxysporum f. sp. colocasiae), Yellows of cabbage and Komatsuna (Fusarium oxysporum f. sp. conglutinans), Panama disease of banana (Fusarium oxysporum f. sp. cubense), Fusarium wilt of strawberry (Fusarium oxysporum f. sp. fragariae), Root rot of lettuce (Fusarium oxysporum f. sp. lactucae), Fusarium wilt of watermelon (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), Fusarium wilt of tomato (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt of melon (Fusarium oxysporum f. sp. melonis), Yellows of radish (Fusarium oxysporum f. sp.raphani), spinach 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 root blight (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), tea gray blight (Pestalotiopsis longiseta, P. theae), Chestnut canker (Endothia parasitica), Citrus black spot (Melanose) (Diaporthe citri), Asparagus stem blight (Phomopsis asparagi), Pear canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Apple canker (Valsa ceratosperma), Rice blast (Magnaporthe grisea), Strawberry crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), Apple bitter rot (Colletotrichum acutatum, Glomerella cingulata), Anthracnose (Colletotrichum acutatum, Glomerella)cingulata), plum anthracnose (Anthracnose, Colletotrichum acutatum), grape ripening rot (Colletotrichum acutatum, Glomerella cingulata), garland chrysanthemum anthracnose (Anthracnose, Colletotrichum acutatum), kidney bean anthracnose (Anthracnose, Colletotrichum lindemuthianum), cucurbit anthracnose (Anthracnose, Colletotrichum orbiculare), yam anthracnose (Anthracnose, Glomerella cingulata), chestnut anthracnose (Anthracnose, Glomerella cingulata), persimmon anthracnose (Anthracnose, Glomerella cingulata), adzuki bean brown stem rot (Phialophora gregata), Chinese yam leaf spot (Pseudophloeosporella dioscoreae), barley scald (Rhynchosporium secalis), wheat brown rust (Puccinia recondita), wheat stripe rust (Puccinia striiformis), rust that occurs on 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), lecithin rust (Puccinia allii), chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisoriumscitamineum), Corn smut (Ustilago maydis), Barley loose smut (Ustilago nuda), Tea net blister blight (Exobasidium reticulatum), Tea blister blight (Exobasidium vexans), Stem rot, Southern blight (Athelia rolfsii), Chrysanthemum root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), Ginger sheath blight (Rhizoctonia solani), Cabbage seedling damping-off (Rhizoctonia solani), Mitsuba damping-off (Rhizoctonia solani), Lettuce bottom rot (Rhizoctonia solani), Turfgrass brown patch, large patch (Rhizoctonia solani), Rice sheath blight Beet blight (Thanatephorus cucumeris), sugar beet root rot (Thanatephorus cucumeris), sugar beet leaf blight (Thanatephorus cucumeris), fig black mold (Rhizopus stolonifer var. stolonifer), cruciferous vegetables clubroot (Plasmodiophora brassicae), sugar beet black root rot (Aphanomyces cochlioides), cruciferous vegetables white rust (Albugo macrospora), downy mildew that occurs on 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 (Peronosporamanshurica), Crucifer downy mildew (Peronospora parasitica), Rose downy mildew (Peronospora sparsa), Sunflower downy mildew (Plasmopara halstedii), Honeybee downy mildew (Plasmopara nivea), Grape downy mildew (Plasmopara viticola), Cucurbit downy mildew (Pseudoperonospora cubensis), Aralia root rot (Phytophthora cactorum), Watermelon brown rot (Phytophthora capsici), Pumpkin late blight (Phytophthora capsici), Bell pepper late blight (Phytophthora capsici), Watermelon late blight (Phytophthora cryptogea), Tomato and potato late blight (Phytophthora infestans), Fig white powdery mildew rot (Phytophthora palmivora), Leaf blight of onion (Phytophthora porri), Phytophthora root and stem rot of soybean (Phytophthora sojae), Phytophthora stem rot of adzuki beans (Phytophthora vignae f. sp. adzukicola), Damping-off of spinach (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Root rot of konjac (Pythium aristosporum), Browning root rot of corn (Pythium arrhenomanes, P. graminicola), Damping-off of cabbage seedlings (Pythium buismaniae, P. myriotylum), Root rot of ginger (Pythium myriotylum), Ginger rhizome rot Rootrot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato bacterial canker (Clavibacter michiganensis subsp. michiganensis), potato scab (Streptomyces spp.), rose crown gall (Rhizobium radiobacter), sorghum bacterial stripe (Burkholderia andropogonis), onion soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), rice bacterial grain rot (Burkholderia gladioli, B. glumae), watermelon bacterial fruit blotch (Acidovorax avenae subsp. Bacterial leaf blight (Acidovorax konjaci), Bacterial leaf blight (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria) nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial leaf spot (Xanthomonas axonopodis pv. vitians), Black rot (Xanthomonas campestris pv. campestris), Bacterial pustule (Xanthomonas campestris pv. glycines), burdock black spot bacterial disease Bacterialspot (Xanthomonas campestris pv. nigromaculans), bacterial spot of pepper (Xanthomonas campestris pv. vesicatoria), citrus canker (Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), kiwifruit bacterial blossom blight (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), kiwifruit bacterial canker (Pseudomonas syringae pv. actinidiae), Loquat canker (Pseudomonas syringae pv. eriobotryae), Bacterial spot of Cucurbitaceae (Pseudomonas syringae pv. lachrymans), Bacterial black spot of Brassicaceae (Pseudomonas syringae pv. maculicola), Plum canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), Tea shoot blight (Pseudomonas syringae pv. theae), Onion soft rot (Dickeya sp., Pectobacterium carotovorum), Fire blight of Rosaceae (Poidomonaceae) (Erwinia amylovora), Konjac soft rot (Pectobacterium carotovorum), Bacterial softrot (Pectobacterium carotovorum).

[0243] The development of control agents for diseases of agricultural and horticultural crops has progressed, and a wide variety of pesticides have been put to practical use to date. However, due to the long-term use of these pesticides, pathogens have recently acquired drug resistance, making it increasingly difficult to control them with conventionally used fungicides. In addition, some existing pesticides are highly toxic, and some persist in the environment for long periods of time, resulting in the emergence of problems of ecosystem disruption. Under these circumstances, the compounds of the present invention have excellent control activity against many pathogens and are highly safe for target crops. Furthermore, the compounds of the present invention can exert sufficient control effects even against pathogens that have acquired resistance to existing fungicides. Furthermore, the compounds of the present invention do not cause phytotoxicity to target crops, have little adverse effect on mammals, fish, and beneficial insects, and have low residual properties and a low environmental impact.

[0244] In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as a medical antibacterial agent and an antibacterial agent for animals, which are used as antifungal agents or agents for controlling internal parasites; an antibacterial and antifungal agent for wood, paper / pulp, adhesives / paints, fibers, leather, etc.; and an industrial fungicide, such as for cooling water channels in manufacturing plants.

[0245] Examples of pathogenic bacteria that can be used as medical antibacterial agents or veterinary antibacterial agents include, but are not limited to, tinea fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Haemophilus influenzae, and Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0246] Examples of fungal strains that can be used as antibacterial and antifungal agents include, but are not limited to, wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, and material-deteriorating microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.

[0247] Examples of fungal strains that can be used as industrial fungicides include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.

[0248] The compounds of the present invention can be used as agents for controlling internal parasites in livestock, poultry, pets, etc., in addition to being used as agricultural and horticultural fungicides.

[0249] Specific examples of target internal parasites include, but are not limited to, the following:

[0250] Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus ylus), Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, and other nematodes; Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Dracunculidae nematodes such as Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus Tapeworms such as Echinococcus granulosus and Echinococcus multilocularis; Fasciola hepatica (F.trematodes such as Paragonimus gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni; ovinoidalis); Trypanosomsa cruzi, Leishmania, Plasmodium, Babesia, Trichomonadidae, Histomanas, Giardia, Toxoplasma, Entamoeba histolytica, Theileria, etc.

[0251] The compounds of the present invention can be used as antifungal agents in addition to being used as agricultural and horticultural fungicides.

[0252] Specific examples of pathogenic bacteria that can be targeted by antifungal agents include, but are not limited to, the following.

[0253] Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, and the like.

[0254] When the compound of the present invention is applied as a plant disease and plant pest control agent, it is usually mixed with a suitable solid or liquid carrier, and if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, or antidegradants are further added, and the compound can be used in any formulation, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granules, water-soluble granules, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granules, or gel. Furthermore, from the viewpoint of labor saving and improved safety, the above-mentioned formulations of any formulation can be used sealed in a water-soluble package.

[0255] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; synthetic silicic acid; and synthetic silicates.

[0256] Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. These solid and liquid carriers may be used alone or in combination of two or more.

[0257] 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, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, and polystyrenesulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; and amphoteric surfactants such as amino acid types and betaine types.

[0258] The content of these surfactants is not particularly limited, but is generally in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

[0259] When the compound of the present invention is used as a pesticide, it may be mixed with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying, if necessary.

[0260] In particular, by applying it in combination with other pesticides or plant hormones, cost reductions can be achieved by reducing the amount of applied drug, and the synergistic action of the mixed drug can be expected to broaden the fungicidal and insecticidal spectrum or to achieve a higher pest control effect.In this case, it is also possible to combine it with multiple known pesticides at the same time.

[0261] In one embodiment, types of pesticides that can be mixed with the compound of the present invention include, for example, compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of their common names are as follows: However, the pesticides that can be mixed are not necessarily limited to these.

[0262] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide polysulfide), benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorph, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture mixture), boscalid (boscalid), bromoconazole (bromoconazole), bupirimate (bupirimate), buthiobate (buthiobate), butylamine (butylamine), lime sulfur mixture (calcium polysulfide), captafol (captafol), captan (captan), carbamorph (carbamorph), carbendazim (carbendazim), carboxin (carboxin), carpropamid (carpropamid), carvone (carvone), cheshunt mixture (cheshunt mixture), chinomethionate (chinomethionat),Chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate chromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetate acid), dichlobentiazox, dichlofluanid, diclone, dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine,Dicloran (dicloran), diethofencarb (diethofencarb), difenoconazole (difenoconazole), diflumetorim (diflumetorim), dimethirimol (dimethirimol), dimethomorph (dimethomorph), dimoxystrobin (dimoxystrobin), diniconazole (diniconazole), diniconazole-M (diniconazole-M), dinobuton (dinobuton), dinocap (dinocap), dinocap-4 (dinocap-4), dinocap-6 (dinocap-6), dinocton (dinocton), dinosulfon (dinosulfon), dinoterbone (dinoterbon), diphenylamine (diphenylamine), dipymetitrone (dipymetitrone), dipyrithione (dipyr ithione), disulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolone, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulf, Phenaminestrobin (fenaminstrobin), fenapanil (fenapanil), fenarimol (fenarimol), fenbuconazole (fenbuconazole), fenfuram (fenfuram), fenhexamid (fenhexamid), fenitropan (fenitropan), fenoxanil (fenoxanil), fenpiclonil (fenpicoxamid),Fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, fluopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfa Flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpet, fosetyl aluminum, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbanil, fluconazole, fluconazole-cis, furmecyclox, furophanate, glycine, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos,8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole ole), ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofetamide, isoflecipram, isotianil, isoprothiolane, isopyrazam, isovaledione, kasugamycin, Kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil onil), meptyldinocap (meptyldinocap), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), metam (metam), metazoxolone (metazoxolon), metconazole (metconazole), methasulfocarb (methasulfocarb), metofuroxam (methfuroxam), methyltetraprole (metyltetraprole), metiram (metiram), metominostrobin (metominostrobin),Metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organic nickel (nickel bis (dimethyldithiocarbamate)), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole fumarate fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxin-D, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb,Proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropoyne, pyraziflumid , pyridaclomethyl (pyridachlometyl), pyridinitril (pyridinitril), pyriophenone (pyriofenone), pyrisoxazole (pyrisoxazole), pyroxychlor (pyroxychlor), pyroxyfur (pyroxyfur), quinacetol-sulfate (quinacetol-sulfate), quinazamid (quinazamid), quinconazole (quinoxyfen), quinofumelin (quinofumelin), quintozene (quintozene), rabenzazole (rabenzazole), salicylanilide (salicylanilide), sedaxane (sedaxane), silthiofam (silthiofam), simeconazole (simeconazole), sodium bicarbonate (sodium hydrogen carbonate), sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tefloctalam, tecnazene, tecoram, tetraconazole, thiabendazole,Thiadifluor (thiadifluor), thicyofen (thicyofen), thifluzamide (thifluzamide), thiochlorfenphim (thiochlorfenphim), thiophanate (thiophanate), thiophanate - methyl (thiophanate-methyl), thiuram (thiram), tiadinil (tiadinil), tioximid (tioximid), tolclofos - methyl (tolclofos-methyl), tolprocarb (tolprocarb), tolylfluanid (tolylfluanid), triadimefon (triadimefon), triadimenol (triadimenol), triamiphos (triamiphos), triarimol (triarimol), triazbutil (triazbutil), triazoxide (triazoxide), tributyltin oxide (tributyltin oxide), trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zalilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zoxamide, shiitake mycelium extract, shiitake fruiting body extract, etc.

[0263] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin 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 alothrin), cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dichloromezothiazol z), dicofol (dicofol), dienochlor (dienochlor), diflovidadin (diflovidazin), diflubenzuron (diflubenzuron), dimefluthrin (dimefluthrin), dimethoate (dimethoate), dimethylvinphos (dimethylvinphos), dimpropyridaz (dimpropyridaz), dinotefuran (dinotefuran), diofenolan (diofenolan), disulfoton (disulfoton), DNOC (DNOC),d-T-80-phthalthrin, emamectin benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethifencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrypyrim, fluazuron, flubenzi amide (flubendiamide), fluchlordiniliprole (fluchlorodiniliprole), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), flufenerim (flufenerim), flufenoxuron (flufenoxuron), flufenprox (flufenprox), flufiprole (flufiprole), fluhexafon (fluhexafon), flumethrin (flumethrin), flupentiofenox (flupentiofenox), flupyradifurone (flupyradifurone), flupirimin (flupyrimin),Fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb, gamma-cyhalothrin, halfenprox, halofenozide, 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, metaflumizone, metalcarb, metaldehyde, methacrifos, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, methyl bromide bromide), metofluthrin, milbemectin, momfluorothrin,Monocrotophos (monocrotophos), muscalure (muscalure), nicofluprole (nicofluprole), nitenpyram (nitenpyram), novaluron (novaluron), noviflumuron (noviflumuron), omethoate (omethoate), oxazosulfyl (oxazosulfyl), oxydemeton-methyl (oxydemeton-methyl), oxydeprofos (oxydeprofos), parathion (parathion), parathion-methyl (parathion-methyl), pentachlorophenol (pentachlorophenol), permethrin (permethrin), phenothrin (phenothrin), phenthoate (phenthoate), phorate (phorate), phosalone (phosalone), phosmet (phosmet), phosphamidon (phosphamidon), phoxim (phoxim), pirimicarb (pirimicarb), pirimiphos-methyl (pirimiphos-methyl), praziquantel (Praziquantel) iquantel), profenofos, profluthrin, propaphos, propargite, prothiofos, protrifenbute, pyflubumide, pymetrozine, pyraclofos, pyrafluprole, pyrethrins, pyridaben ), pyridalyl (pyridalyl), pyrifluquinazon (pyrifluquinazon), pyrimidifen (pyrimidifen), pyriprole (pyriprole), pyriproxyfen (pyriproxyfen), resmethrin (resmethrin), rotenone (rotenone), silafluofen (silafluofen), spidoxamat (spidoxamat), spinetoram (spinetoram), spinosad (spinosad), spirodiclofen (spirodiclofen),Spiromesifen, spiropidione, spirotetramate, spiromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorantraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin rin), tetraniliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, and zeta-cypermethrin, etc.

[0264] Parasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin fluthrin), zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, Pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos , ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenocarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,Tigolaner (tigolaner), esafoxolaner (esafoxolaner), modoflaner (modoflaner), umifoxolaner (umifoxolaner), mivorilaner (mivorilaner), avermectin (avermectin), ivermectin (ivermectin), doramectin (doramectin), eprinomectin (eprinomectin), madeuramycin (maduramycin), milbemycin (milbemycin), milbemycin oxime (milbemycin oxime), moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide), emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsomine dihydrochloride, metronidazole, methylidine,Monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, and triclabendazole, etc.

[0265] Antifungal agents: ketoconazole and miconazole nitrate, etc.

[0266] Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid acid), danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid acid), oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Talaromyces, Trichoderma, and Uniothyrium, etc.

[0267] The application amount of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but generally, an amount of the active ingredient is 0.005 to 50 kg per hectare (ha), and preferably 0.01 to 1 kg.

[0268] Next, formulation examples for formulations using the compounds of the present invention are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[0269] [Wettable powder] Compound of the present invention 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts As the others, for example, an anti-caking agent or an anti-decomposition agent can be mentioned.

[0270] [Emulsifiable concentrate] Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts As the other, for example, a spreading agent or a decomposition inhibitor can be mentioned.

[0271] [Suspending agent] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As the others, for example, an antifreeze agent or a thickener can be mentioned.

[0272] [Water Dispersible Granule] Compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts As the others, for example, a binder or a decomposition inhibitor can be mentioned.

[0273] [Liquid Formulation] Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts As the other ingredients, for example, an antifreeze agent or a spreading agent can be mentioned.

[0274] [Granules] Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts As the others, for example, a binder or a decomposition inhibitor can be mentioned.

[0275] [Dust] Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts As the other, for example, an anti-drift agent or anti-decomposition agent can be mentioned.

[0276] When used, the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or is sprayed without dilution.

[0277] Next, specific formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient are shown below, but the formulations of the present invention, including the compound of the present invention, are not limited to these. In the following formulation examples, "parts" means parts by weight.

[0278] Formulation Example 1: Emulsifiable concentrate Compound No. 1-001 of the present invention 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Sorpol 2680 5 parts (a mixture of a nonionic surfactant and anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) The above ingredients are uniformly mixed to prepare an emulsifiable concentrate. When used, the emulsifiable concentrate is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient becomes 0.005 to 50 kg per hectare.

[0279] Formulation Example 2: Wettable Powder Compound No. 1-001 of the present invention 25 parts Pyrophyllite 66 parts Sorpol 5039 4 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Carplex #80D 3 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) Calcium lignosulfonate 2 parts The above ingredients are uniformly mixed and pulverized to prepare a wettable powder. When used, the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient becomes 0.005 to 50 kg per hectare.

[0280] Formulation Example 3: Dust Compound No. 1-001 of the present invention 3 parts Carplex #80D 0.5 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and pulverized to prepare a dust. When used, the dust is applied so that the amount of the active ingredient becomes 0.005 to 50 kg per hectare.

[0281] Formulation Example 4: Granules Compound No. 1-001 of the present invention 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part The above ingredients are homogeneously mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give granules. When used, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

[0282] Formulation Example 5: Suspension Compound No. 1-001 of the present invention 25 parts Sorpol 3353 5 parts (nonionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Lunox 1000C 0.5 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts The above ingredients except for the active ingredient (compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred well, followed by wet pulverization in a sand mill to obtain a flowable formulation. When used, the flowable formulation is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0283] Formulation Example 6: Granular Water Dispersible Agent Compound No. 1-001 of the present invention 75 parts Hitenol NE-15 5 parts (anionic surfactant: trade name, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) Vanilex N 10 parts (anionic surfactant: trade name, manufactured by Nippon Paper Industries Co., Ltd.) Carplex #80D 10 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) The above ingredients are uniformly mixed and finely pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give a dry flowable formulation. When used, the mixture is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.

[0284] The compound of the present invention can be applied by foliage spray, soil treatment, seed disinfection, etc., but common methods commonly used by those skilled in the art are also effective.

[0285] [Summary] As described above, the present invention relates to the following [1] to

[78] .

[0286] [1] Formula (1):

[0287] [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula:

[0288] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R Ｘ is 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 represents −4, and R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula,

[0289] X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X １ In the above relationship, when u5 represents an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, １ In the relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-29 or E-30, and Z ２ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; Z ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, E-1 to E-30 each represent a structure represented by the following structural formula:

[0290] Z ａ is a hydroxyl, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, —C(═NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａmay be the same as or different from each other, ａ In the relationship, when v4 represents an integer of 2, 3 or 4, each Z ａ may be the same as or different from each other, ｂ is C １ ~C ６ represents alkyl, R ａ is hydroxy, cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylcarbonylamino, phenylcarbonylamino, -OR ｇ , -C(O)R ｇ , -NR ｈ SO ２ R ｊ or Q-1, wherein Q-1 represents a structure represented by the following structural formula:

[0291] Q １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, １ In the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Q １ may be the same as or different from each other, R ｂ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｄ is amino, hydroxyamino, C １ ~C６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ R represents (alkyl)amino, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy, R ｆ is a hydrogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkylsulfonyl or C １ ~C ６ represents haloalkylsulfonyl, R ｇ represents Q-1, and R ｈ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６m5 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, p represents an integer of 0 or 1, v4 represents an integer of 0, 1, 2, 3, or 4, v2 represents an integer of 0, 1, or 2, v1 represents an integer of 0 or 1, and w5 represents an integer of 0, 1, 2, 3, 4, or 5.

[0292] [2] G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ Alkyl, R Ｘ -1 or R Ｘ represents −2, and R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ represents a hydrogen atom, R ４ represents a hydrogen atom; ５ represents a hydrogen atom; Z １ represents E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z ２ is C １ ~C ６ represents alkoxy; Z ａ is a hydroxyl, thiol, halogen atom, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １~C ６ Alkoxy, C １ ~C ６ Alkylthio, -C(=NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Q １ represents a halogen atom; ｂ is C １ ~C ６ represents alkyl, R ｃ is C １ ~C ６ represents alkyl, R ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents alkoxy, R ｈ is C １ ~C ６ m5 represents an integer of 0 or 1, n4 represents an integer of 0 or 1, u5 represents an integer of 0, u4 represents an integer of 0, p represents an integer of 1, v4 represents an integer of 0, and w5 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to [1] above,

[0293] [3] Z １ represents E-3, E-4, E-5, E-6, E-8, E-9, E-12, E-13, or E-29, or a salt thereof.

[0294] [4] Z ａ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, —C(═NOR ｂ ) R ｃ, -NR ｅ R ｆ , phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; R ａ is C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to the above [3], wherein alkylthio is represented.

[0295] [5] Z １ represents E-3, E-4, E-5 or E-29, or a salt thereof according to the above [3] or [4].

[0296] [6] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ The pyrazole compound or salt thereof according to the above [1], wherein alkylsulfonyl is represented.

[0297] [7] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to the above [1], wherein the compound represents haloalkoxy.

[0298] [8] G １is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to the above [1], wherein the compound represents haloalkoxy.

[0299] [9] G １ is a nitro, cyano, halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ The pyrazole compound or salt thereof according to the above [1], wherein haloalkyl is present.

[0300]

[10] G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ m5 represents an integer of 0 or 1. The pyrazole compound or salt thereof according to [1] above.

[0301]

[11] G １ is C １ ~C ６ Alkyl or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [3] to

[10] , wherein haloalkyl is represented.

[0302]

[12] G １ is C １ ~C ６ The pyrazole compound or salt thereof according to the above

[11] , wherein R represents alkyl.

[0303]

[13] G １ is C １ ~C ６ The pyrazole compound or salt thereof according to the above

[11] , wherein haloalkyl is present.

[0304]

[14] G １ represents a halogen atom, or a salt thereof.

[0305]

[15] The pyrazole compound or salt thereof according to any one of the above [1] to

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

[0306]

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

[14] , wherein m5 represents an integer of 1.

[0307]

[17] The pyrazole compound or salt thereof according to any one of the above [1] to [5], wherein m5 represents an integer of 0.

[0308]

[18] R Ｘ is C １ ~C ６ Alkyl, R Ｘ -1 or R Ｘ The pyrazole compound or salt thereof according to any one of the above [1] and [6] to

[17] , wherein R represents -2.

[0309]

[19] R Ｘ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[17] , wherein R represents alkyl.

[0310]

[20] R Ｘ represents tert-butyl, or a salt thereof.

[0311]

[21] R Ｘ is R Ｘ -1 or R Ｘ -2, u5 represents an integer of 0, and u4 represents an integer of 0. The pyrazole compound or a salt thereof according to any one of [1] to

[17] above.

[0312]

[22] R Ｘ is R Ｘ The pyrazole compound or salt thereof according to the above

[21] , wherein R represents -1.

[0313]

[23] R Ｘ is R Ｘ The pyrazole compound or salt thereof according to the above

[21] , wherein R represents -2.

[0314]

[24] R Ｙ is a hydrogen atom, a halogen atom or C１ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] and [6] to

[23] , wherein R represents alkyl.

[0315]

[25] R Ｙ represents a hydrogen atom, or a salt thereof.

[0316]

[26] R Ｙ represents a halogen atom, or a salt thereof.

[0317]

[27] R Ｙ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[23] , wherein R represents alkyl.

[0318]

[28] R １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ５ represents a hydrogen atom, and p represents an integer of 1. The pyrazole compound or salt thereof according to any one of [1] and [6] to

[27] above.

[0319]

[29] Z １ represents E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z ２ is C １ ~C ６ n4 represents an integer of 0 or 1. The pyrazole compound or salt thereof according to any one of [1] and [6] to

[28] above.

[0320]

[30] Z １ represents E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-12, E-13, E-21 or E-29.

[0321]

[31] Z １ represents E-3, E-4, E-5, E-6, E-8, E-9, E-12, E-13, or E-29, or a salt thereof.

[0322]

[32] Z １ represents E-3, E-4, E-5, E-6, E-12 or E-29, or a salt thereof.

[0323]

[33] Z １ represents E-3, E-4, E-5 or E-29, or a salt thereof.

[0324]

[34] Z １ represents E-3, E-4 or E-5, or a salt thereof.

[0325]

[35] Z １ represents E-3. The pyrazole compound or salt thereof according to

[30] above.

[0326]

[36] Z １ represents E-4. The pyrazole compound or salt thereof according to the above

[30] .

[0327]

[37] Z １ represents E-5.

[0328]

[38] Z １ represents E-29.

[0329]

[39] Z ａ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, —C(═NOR ｂ ) R ｃ , -NR ｅ R ｆ, phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; R ｂ is C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents alkoxy, R ｆ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[38] , wherein R represents (alkyl)aminocarbonyl.

[0330]

[40] R ｅ is a hydrogen atom, C １ ~C ６ Alkyl or C ３ ~C １０ represents cycloalkyl, R ｆ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ The pyrazole compound or salt thereof according to the above

[39] , wherein R is 1 or 2, R is 2 or 3, R is 3 or 4, R is 4 or 5, R is 5 or 6, R is 6 or 7, R is 7 or 8, R is 8 or 9, R is 9 or 10, R is 10 or 11, R is 11 or 12, R is 13 or 14, R is 15 or

[0331]

[41] R ｅ is a hydrogen atom or C １~C ６ represents alkyl, R ｆ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ The pyrazole compound or salt thereof according to the above

[39] , wherein R represents alkylcarbonyl.

[0332]

[42] Z ａ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl, R ａ is C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , which represents alkylthio.

[0333]

[43] Z ａ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ａ is C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[42] , which represents alkylthio.

[0334]

[44] Z ａ is C １ ~C ６ Alkyl or R ａ C substituted with １ ~C ６ represents alkyl, R ａ is C １ ~C ６The pyrazole compound or salt thereof according to the above

[43] , wherein R represents alkoxy.

[0335]

[45] Z ａ is C １ ~C ６ Alkyl or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , wherein haloalkyl is represented.

[0336]

[46] Z ａ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , wherein R represents alkyl.

[0337]

[47] Z ａ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , wherein haloalkyl is represented.

[0338]

[48] ​​Z ａ is R ａ C substituted with １ ~C ６ represents alkyl, R ａ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , wherein R represents alkoxy.

[0339]

[49] Z １ represents E-3, Z ａ is C １ ~C ６ Alkyl or R ａ C substituted with １ ~C ６ represents alkyl, R ａ is C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[39] , wherein R represents alkoxy.

[0340]

[50] Z ａ is -C(=NOR ｂ ) R ｃ , -NR ｅ Rｆ , phenyl, pyrrolidin-1-yl, morpholin-1-yl, or piperidin-1-yl, or a salt thereof.

[0341]

[51] Z ａ is -C(=NOR ｂ ) R ｃ or -C(O)R ｄ represents R ｂ is C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｅ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｆ is a hydrogen atom or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[38] , wherein R represents alkyl.

[0342]

[52] R ａ is C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylcarbonylamino, phenylcarbonylamino, -OR ｇ , -C(O)R ｇ , -NR ｈ SO ２ R ｊ or Q-1.

[0343]

[53] R ａ is C １ ~C ６ Alkoxy, C １ ~C６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[41] , which represents alkylcarbonylamino or phenylcarbonylamino.

[0344]

[54] R ａ is C １ ~C ６ Alkoxy, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylcarbonylamino, -OR ｇ , -C(O)R ｇ or -NR ｈ SO ２ R ｊ represents R ｇ represents Q-1, and Q １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R ｈ is C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６

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

[41] above, wherein w5 represents an integer of 0 or 1.

[0345]

[55] Q １ represents a halogen atom, and w5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[54] above.

[0346]

[56] The pyrazole compound or salt thereof according to the above

[54] , wherein w5 represents an integer of 0.

[0347]

[57] R ａ is C １ ~C ６ Alkoxy or C １ ~C ６

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

[41] above, wherein R represents alkylcarbonylamino. ａ is C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ The pyrazole compound or salt thereof according to any one of the above [1] to

[41] , wherein alkylsulfonyl is present.

[0348]

[59] R ａ is C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ The pyrazole compound or salt thereof according to any one of [1] to

[41] above, wherein alkylsulfonyl is present.

[0349]

[60] R ａ Is -OR ｇ , -C(O)R ｇ , -NR ｈ SO ２ R ｊ or Q-1, １ represents a halogen atom; and w5 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of [1] to

[41] above.

[0350]

[61] Formula (1):

[0351] [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula:

[0352] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C１０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R Ｘ is 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 represents −4, and R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula,

[0353] X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C６ represents alkoxy; X １ In the above relationship, when u5 represents an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, １ In the relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-4 or E-5, and Z ２ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C１ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; Z ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, E-1 to E-5 each represent a structure represented by the following structural formula:

[0354] Z ａ is a hydroxyl, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ represents an alkoxycarbonyl; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, R ａ is cyano or C １ ~C ６ 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, p represents an integer of 0 or 1, v2 represents an integer of 0, 1, or 2, and v1 represents an integer of 0 or 1.

[0355]

[62] G １ is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ５ represents a hydrogen atom; Z １ represents E-2 to E-4 or E-5, and Z ２ is C １ ~C ６ represents alkoxy; Z ａ is hydroxy, thiol, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents alkylthio, R ａ is C １ ~C ６ m5 represents an integer of 1; n4 represents an integer of 0; p represents an integer of 1; v2 represents an integer of 1; and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to

[62] above.

[0356]

[63] Formula (1):

[0357] [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula:

[0358] G １is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R Ｘ is 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 represents −4, and R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula,

[0359] X １ is a halogen atom, C １~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X １ In the above relationship, when u5 represents an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, １ In the relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-4 or E-5, and Z ２ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C１ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; Z ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, E-1 to E-5 each represent a structure represented by the following structural formula:

[0360] Z ａ is a hydroxyl, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ represents an alkoxycarbonyl; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, R ａ is cyano or C １ ~C ６m5 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, p represents an integer of 0 or 1, v2 represents an integer of 0, 1, or 2, and v1 represents an integer of 0 or 1.

[0361]

[64] G １ is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ５ represents a hydrogen atom; Z １ represents E-2 to E-4 or E-5, and Z ２ is C １ ~C ６ represents alkoxy; Z ａ is hydroxy, thiol, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents alkylthio, R ａ is C １ ~C ６m5 represents an integer of 1; n4 represents an integer of 0; p represents an integer of 1; and v2 represents an integer of 1. The pyrazole compound or a salt thereof according to

[63] above,

[0362]

[65] Formula (1):

[0363] [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula:

[0364] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same as or different from each other, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０Cycloalkyl, C １ ~C ６ Haloalkyl, benzyl, R Ｘ -1, R Ｘ -2, R Ｘ -3 or R Ｘ represents −4, and R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula,

[0365] X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X １ In the above relationship, when u5 represents an integer of 2, 3, 4 or 5, each X １ may be the same as or different from each other, １ In the relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same as or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-26 or E-27,２ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; Z ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, E-1 to E-27 each represent a structure represented by the following structural formula:

[0366] Z ａ is a hydroxyl, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl, C １ ~C ６Alkoxycarbonyl, —C(═NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, ａ In the relationship, when v4 represents an integer of 2, 3 or 4, each Z ａ may be the same as or different from each other, ｂ is C １ ~C ６ represents alkyl, R ａ is hydroxy, cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy or C １ ~C ６ represents alkylcarbonylamino, R ｂ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｄ is amino, C １ ~C ６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ R represents (alkyl)amino, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy, R ｆ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl or C １ ~C ６ 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, p represents an integer of 0 or 1, v4 represents an integer of 0, 1, 2, 3, or 4, v2 represents an integer of 0, 1, or 2, and v1 represents an integer of 0 or 1.

[0367]

[66] G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ５ represents a hydrogen atom; Z １represents E-2 to E-4, E-5, E-7, E-9 to E-13, E-16 to E-19, E-21, E-24 to E-26, or E-27; Z ２ is C １ ~C ６ represents alkoxy; Z ａ is a hydroxyl, thiol, halogen atom, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, -C(=NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ , pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; R ａ is hydroxy, C １ ~C ６ Alkoxy or C １ ~C ６ represents alkylcarbonyloxy; R ｂ is C １ ~C ６ represents alkyl, R ｃ is C １ ~C ６ represents alkyl, R ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents alkoxy, R ｆ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C１ ~C ６ alkyl)aminocarbonyl or C １ ~C ６ m5 represents an integer of 1; n4 represents an integer of 0; p represents an integer of 1; and v4 represents an integer of 0. The pyrazole compound or a salt thereof according to

[65] above,

[0368]

[67] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein n4 represents an integer of 1.

[0369]

[68] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein n4 represents an integer of 0.

[0370]

[69] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein v2 represents an integer of 0 or 1.

[0371]

[70] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein v2 represents an integer of 0.

[0372]

[71] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein v2 represents an integer of 1.

[0373]

[72] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein v1 represents an integer of 0.

[0374]

[73] The pyrazole compound or salt thereof according to any one of the above [1] to

[66] , wherein v1 represents an integer of 1.

[0375]

[74] An agricultural chemical containing, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of [1] to

[73] above.

[0376]

[75] A fungicide containing, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of [1] to

[73] above.

[0377]

[76] An agricultural and horticultural fungicide containing, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of [1] to

[73] above.

[0378]

[77] An antifungal agent containing, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of [1] to

[73] above.

[0379]

[78] An internal parasite control agent containing, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of [1] to

[73] above.

[0380] EXAMPLES The present invention will be explained in more detail below by describing examples of synthesis and testing of the compounds of the present invention, but the present invention is not limited to these examples.

[0381] For the medium pressure preparative liquid chromatography described in the synthesis examples, a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column) was used.

[0382] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter, １ The chemical shift values ​​of H-NMR are expressed as Me as a standard substance. ４ Using Si (tetramethylsilane), measurements were made at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). １ The symbols in the H-NMR chemical shift values ​​have the following meanings.

[0383] s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, sep: septet, m: multiplet, br: broad singlet.

[0384] [Synthesis Examples] Synthesis Example 1: Synthesis of 1-(tert-butyl)-N-(4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-013) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(((2,2,2-trifluoroacetimidamido)oxy)carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 150 mg of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoic acid and 3 ml of dichloromethane, 92 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 49 mg of 2,2,2-trifluoro-N'-hydroxyacetimidamide, 49 mg of triethylamine, and 4 mg of 1-hydroxy-7-azabenzotriazole were added successively at room temperature, and the mixture was stirred at the same temperature for 16 hours. After completion of the reaction, 3 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (3 ml × 1). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 220 mg of the target product as an oil.

[0385] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide A mixed solution of 220 mg of 1-(tert-butyl)-N-(4-(((2,2,2-trifluoroacetimidamido)oxy)carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide obtained in Step 1 and 3 ml of pyridine was stirred at 80°C for 6 hours. After completion of the reaction, 1 mol / l hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate (3 ml x 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent to give 108 mg of the desired product as a white solid, melting point 125-127°C.

[0386] Synthesis Example 2: Synthesis of 1-(tert-butyl)-N-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-003) To a mixed solution of 150 mg of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 3 ml of N,N-dimethylformamide, 171 mg of potassium carbonate and 63 mg of acetic anhydride were added at room temperature, and the mixture was stirred at 50°C for 3 hours. After completion of the reaction, 6 ml of water was added to the reaction mixture, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate=1:2 (volume ratio, the same applies hereinafter) (5 ml x 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate [gradient from 9:1 to 1:9 (volume ratio, the same applies hereinafter)] as an eluent to obtain 111 mg of the target compound as a white solid. Melting point: 119-121°C.

[0387] Synthesis Example 3: Synthesis of 1-(tert-butyl)-N-(4-(4-methyl-thiazol-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-011) To a mixed solution of 100 mg of 1-(tert-butyl)-N-(4-carbamothioylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml of N,N-dimethylformamide, 19 mg of 1-chloropropan-2-one was added at room temperature, and the mixture was stirred at 60°C for 20 hours. After completion of the reaction, 6 ml of water was added to the reaction mixture, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate=1:1 (3 ml × 1 time). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 111 mg of the desired product as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz):δ7.76 (d, J = 8.1 Hz, 2H), 7.40-7.27 (m, 2H), 7.25-7.13 (m, 4H), 7.08-7.01 (m, 1H), 6.85 (s, 1H), 6.50-6.40 (m, 1H), 3.66 (q, J = 6.7 Hz, 2H), 2.83 (t, J = 6.9 Hz, 2H), 2.98 (s, 3H), 1.72 (s, 9H).

[0388] Synthesis Example 4: Synthesis of 1-(tert-butyl)-N-(4-(5-propyl-1,3,4-oxadiazol-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-027) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(2-butyrylhydrazine-1-carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 100 mg of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoic acid and 3 ml of tetrahydrofuran, 68 mg of 1,1'-carbonyldiimidazole and 107 mg of butyrohydrazide were added under ice-cooling, and the mixture was stirred at room temperature for 4 hours. After stirring was completed, the reaction mixture was stirred at 60°C for 4 hours, and then stirred under reflux for 2 hours. After the reaction was completed, 5 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (5 ml x 1). The resulting organic layer was washed with 1 mol / l hydrochloric acid, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 138 mg of the target product as an oil.

[0389] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(5-propyl-1,3,4-oxadiazol-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 138 mg of 1-(tert-butyl)-N-(4-(2-butyrylhydrazine-1-carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 ml of 1,2-dichloroethane, 100 mg of methyl N-(triethylammoniosulfonyl)carbamate was added at room temperature, and the mixture was stirred under reflux for 3 hours. After stirring was completed, 20 mg of methyl N-(triethylammoniosulfonyl)carbamate was added to the reaction mixture under reflux, and the mixture was stirred at the same temperature for 1 hour. After the reaction was completed, 5 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (3 ml x 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent to obtain 42 mg of the target compound as a white solid. Melting point: 83-86°C.

[0390] Synthesis Example 5: Synthesis of 1-(tert-butyl)-N-(4-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-002) To a mixed solution of 100 mg of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml of tetrahydrofuran, 65 mg of 1,1'-carbonyldiimidazole was added at room temperature, and the mixture was stirred at 50°C for 20 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 5 ml of 1 mol / L hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate (5 ml x 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 2 ml of diisopropyl ether to obtain 90 mg of the target product as a white solid. Melting point: 197-199°C.

[0391] Synthesis Example 6: Synthesis of 1-(tert-butyl)-N-(4-(5-methoxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-009) To a mixed solution of 100 mg of 1-(tert-butyl)-N-(4-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 40 mg of potassium carbonate, and 2 ml of acetonitrile, 33 mg of methyl iodide was added at room temperature, and the mixture was stirred at 50°C for 14 hours. After stirring was completed, 73 mg of methyl iodide was added to the reaction mixture at the same temperature, and the mixture was stirred at 60°C for 1 hour. After the reaction was completed, the solvent was distilled off under reduced pressure. To the resulting residue, 3 ml of water was added, and the mixture was extracted with ethyl acetate (3 ml x 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, to obtain 83 mg of the target product as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz):δ7.44-7.40 (m, 3H), 7.39-7.30 (m, 3H), 7.26-7.22 (m, 1H), 7.16 (s, 1H), 7.14-7.07 (m, 1H), 6.60-6.50 (m, 1H), 3.67 (q, J = 6.8 Hz, 2H), 2.88 (t, J = 7.1 Hz, 2H), 3.27 (s, 3H), 1.72 (s, 9H).

[0392] Synthesis Example 7: Synthesis of N-(4-(5-amino-1,2,4-oxadiazol-3-yl)phenethyl)-1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-145) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(5-(methylsulfinyl)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.19 g of 1-(tert-butyl)-N-(4-(5-(methylthio)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide and 30 ml of dichloromethane, 1.00 g of metachloroperbenzoic acid (containing 30% by mass of water) was added under ice-cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, 30 ml of saturated aqueous sodium hydrogen carbonate solution and 30 ml of saturated aqueous sodium thiosulfate solution were added at room temperature, and the mixture was extracted with dichloromethane (50 ml x 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.20 g of the target product as a resinous substance.

[0393] Step 2: Synthesis of N-(4-(5-amino-1,2,4-oxadiazol-3-yl)phenethyl)-1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide A mixed solution of 520 mg of 1-(tert-butyl)-N-(4-(5-(methylsulfinyl)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide, 8 ml of 30% by mass aqueous ammonia, and 4 ml of tetrahydrofuran was stirred at room temperature for 5 hours. After completion of the reaction, 50 ml of water was added at room temperature, and the mixture was extracted with ethyl acetate (50 ml x 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 0:10) as an eluent to give 380 mg of the target product as a white solid, melting point 174-176°C.

[0394] Synthesis Example 8: Synthesis of 3-(4-(2-(1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide)ethyl)phenyl)-N-isopropyl-1,2,4-oxadiazole-5-carboxamide (Compound No. 1-147) To a mixed solution of 50 mg of 1-(tert-butyl)-4-(3-methylphenoxy)-N-(4-(5-(trichloromethyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide and 1 ml of tetrahydrofuran, 90 μl of isopropylamine was added at room temperature, and the mixture was stirred at the same temperature for 16 hours. After completion of the reaction, 10 ml of water was added at room temperature, and the mixture was extracted with chloroform (15 ml × 3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 35 mg of the desired product as an oil. 1 H-NMR (CDCl3, Me4Si, 400MHz):δ7.94-7.90 (m, 1H), 7.42-7.40 (m, 1H), 7.29-7.12 (m, 3H), 7.10 (s, 1H), 7.00-6.87 (m, 2H), 6.76-6.72 (m, 3H), 4.37-4.27 (m, 1H), 3.71-3.63 (m, 2H), 2.91-2.84 (m, 2H), 2.35-2.25 (m, 3H), 1.76-1.66 (m, 9H), 1.35-1.30 (m, 3H), 1.28-1.19 (m, 3H).

[0395] Synthesis Example 9: Synthesis of 1-(tert-butyl)-N-(4-(2-methyl-2H-tetrazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole (Compound No. 1-322) A mixed solution of 38 mg of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 1 ml of N,N-dimethylformamide was added with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium at room temperature. 44 mg of 3-oxide hexafluorophosphate, 40 mg of N,N-diisopropylethylamine, and 25 mg of 2-(4-(2-methyl-2H-tetrazol-5-yl)phenylethan-1-amine hydrochloride were added, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, 2 ml of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate=1:1 (2 ml × 1). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, and 28 mg of the target product was obtained as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz):δ7.96-7.93 (m, 2H), 7.39-7.03 (m, 8H), 4.38 (s, 3H), 3.70-3.63 (m, 2H), 2.84 (t, J = 6.8 Hz, 2H), 1.66 (s, 9H).

[0396] Reference Examples The following are reference examples of methods for producing intermediates for the compounds of the present invention.

[0397] Reference Example 1: Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid 2.5 g of N-iodosuccinimide was added to a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid at room temperature, and the mixture was stirred at 80°C for 30 minutes. After completion of the reaction, 50 ml of water was added at room temperature, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target product as a pink solid. Melting point: 191-193°C.

[0398] Reference Example 2: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one A mixed solution of 4.7 g of 1-(3-(trifluoromethyl)phenoxy)propan-2-one and 2.9 g of N,N-dimethylformamide dimethyl acetal was stirred at 80°C for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent. To the resulting oily substance were added 10 ml of diisopropyl ether and 10 ml of n-hexane, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure to obtain 2.36 g of the target product as a light brown solid. Melting point: 112-114°C.

[0399] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one, 1.64 g of tert-butylhydrazine hydrochloride, and 25 ml of 1,4-dioxane was stirred at 100°C for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the resulting residue, and the mixture was extracted with n-hexane (20 ml x 2). The resulting organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (5:1) as an eluent to obtain 2.51 g of the target product as a pale yellow oil. 1 H-NMR (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).

[0400] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 930 mg of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml of tert-butyl alcohol, and 4.3 ml of water, 1.48 g of potassium permanganate was added at room temperature, and the mixture was stirred at 100°C for 2 hours. After stirring was completed, 1.48 g of potassium permanganate was added to the reaction mixture at the same temperature, and the mixture was stirred at the same temperature for 2 hours. After the reaction was completed, the reaction mixture was filtered through Celite, and the Celite was washed with 20 ml of water. The aqueous layer of the obtained filtrate was washed with chloroform (20 ml × 2 times), and then 1 mol / l hydrochloric acid was added until the pH reached 1, followed by extraction with chloroform (20 ml × 2 times). The resulting organic layer was washed with water, then dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 ml of n-hexane and dried under reduced pressure to obtain 209 mg of the target product as a white solid. Melting point: 120-124°C.

[0401] Reference Example 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)acrylaldehyde 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 was completed, a solution of 5.0 g of 1-(2,2-dimethoxyethoxy)-3-(trifluoromethyl)benzene in 5 ml of N,N-dimethylformamide was added under ice-cooling to the reaction mixture, and the mixture was stirred at 70°C for 30 minutes. After the reaction was completed, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water, and 5 ml of ethanol, and the mixture was stirred at room temperature for 1 hour. After stirring was completed, the reaction mixture was extracted with toluene (40 ml x 2). The resulting organic layer was washed with water, dehydrated and dried over saturated brine and then over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.40 g of the target product as a brown oil. 1H-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).

[0402] 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 completion of the reaction, 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 x 2). The resulting organic layer was washed with water, then dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 400 mg of the target product as a red oil. 1H-NMR (CDCl3, Me4Si, 400MHz): δ 7.46-7.20 (m, 7H), 7.20-7.14 (m, 2H), 7.10-7.06 (m, 1H), 7.03-6.96 (m, 1H), 5.29 (s, 2H) Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Under a nitrogen atmosphere, 0.85 ml of a 1.6 mol / l n-butyllithium n-hexane solution was added dropwise to a solution of 360 mg of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole in 10 ml of tetrahydrofuran at −78° C., and the mixture was stirred at the same temperature for 10 minutes. After stirring was completed, 1.0 g of dry ice was added to the reaction mixture at -78°C, and the mixture was stirred at the same temperature for 5 minutes. After the reaction was completed, 10 ml of 1 mol / L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate:acetic acid (gradient from 74:25:1 to 39:60:1) as the eluent, to obtain 45 mg of the target product as a colorless solid. Melting point: 124-126°C.

[0403] Reference Example 4: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate (Compound No. ii-004) To a mixed solution of 1.00 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid and 10 ml of acetone, 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were added successively at room temperature, and the mixture was stirred at the same temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the resulting residue, 20 ml of water was added, and the mixture was extracted with ethyl acetate (20 ml × 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target product as a yellow solid. Melting point: 69-71°C.

[0404] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (Compound No. ii-005) Under a nitrogen atmosphere, 0.10 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride was added to a mixed solution of 0.50 g of methyl (4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxine, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane at room temperature, and the mixture was stirred at 100°C for 16 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml x 3 times). The mixture was dehydrated and dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 10:0 to 9:1) as an eluent, to obtain 0.30 g of the target product as a yellow oil. 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).

[0405] Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (Compound No. i-036) (To a mixed solution of 39.0 g of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol, a mixed solution of 27.1 g of sodium hydroxide and 100 ml of water was added at room temperature, and the mixture was stirred at 45°C for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 50 ml of water was added, and then 35% by mass hydrochloric acid was added until the pH reached 2, and the precipitated solid was collected by filtration. The obtained solid was dried under reduced pressure and washed with 100 ml of n-hexane to obtain 37.0 g of the target product as a white solid. Melting point: 116-118°C.

[0406] Reference Example 5: Synthesis of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoic acid Step 1: Synthesis of methyl 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoate To a mixed solution of 3.25 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 20 ml of dichloromethane were added 7 mg of N,N-dimethylformamide and 1.3 ml of oxalyl chloride successively at room temperature, followed by stirring at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and 25 ml of dichloromethane was added to the resulting residue. The reaction mixture was added to a mixed solution of 2.35 g of methyl 4-(2-aminoethyl)benzoate hydrochloride, 4.1 ml of triethylamine, and 20 ml of dichloromethane under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 30 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml x 1). The resulting organic layer was washed with 1 mol / l hydrochloric acid, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 8:2) as the eluent. The resulting solid was washed with 10 ml of n-hexane, yielding 3.19 g of the target product as a white solid. 1H-NMR (CDCl3, Me4Si, 300MHz):δ7.88-7.81 (m, 2H), 7.45-7.30 (m, 2H), 7.23-7.16 (m, 3H), 7.13 (s, 1H), 7.10-7.00 (m, 1H), 6.52-6.39 (m, 1H), 3.89 (s, 3H), 3.73-3.61 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H). . Step 2: Synthesis of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoic acid To a mixed solution of 1.20 g of methyl 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamido)ethyl)benzoate and 8 ml of ethanol, 8 ml of 1 mol / l aqueous sodium hydroxide solution was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure. 10 ml of 1 mol / l hydrochloric acid was added to the resulting residue, and the mixture was extracted with ethyl acetate (20 ml × 1 time). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 ml of diisopropyl ether to obtain 0.84 g of the target product as a white solid.

[0407] Reference Example 6: Synthesis of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide Step 1: Synthesis of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.63 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 10 ml of dichloromethane were added 0.95 g of oxalyl chloride and 4 mg of N,N-dimethylformamide in that order at room temperature, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure, and 10 ml of ethyl acetate was added to the resulting residue. The reaction mixture was added to a mixed solution of 1.00 g of 4-(2-aminoethyl)benzonitrile hydrochloride, 1.71 g of potassium carbonate, and 10 ml of water under ice-cooling, and stirred at room temperature for 15 hours. After completion of the reaction, the organic layer of the reaction mixture was washed with 1 mol / l hydrochloric acid, dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent, yielding 2.26 g of the target product as an orange solid. Melting point: 124-125°C.

[0408] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.26 g of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 10 ml of ethanol, 0.23 g of hydroxylamine hydrochloride and 0.46 g of potassium carbonate were added successively at room temperature, and the mixture was stirred at 80°C for 1 hour. After stirring was completed, 0.36 g of a 50% by mass aqueous hydroxylamine solution was added at the same temperature, and the mixture was stirred at the same temperature for 3 hours. After the reaction was completed, 30 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure and washed with 20 ml of diisopropyl ether to give 1.00 g of the target product as a pale pink solid, melting point 126-128°C.

[0409] Reference Example 7: Synthesis of 1-(tert-butyl)-N-(4-carbamothioylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 0.50 g of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 5 ml of N,N-dimethylformamide, 0.11 g of magnesium chloride and 176 mg of sodium hydrosulfide hydrate (purity: 70% by mass) were added successively at room temperature, and the mixture was stirred at the same temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and 10 ml of ethyl acetate was added to the resulting residue. The reaction mixture was added to a mixed solution of 1.00 g of 4-(2-aminoethyl)benzonitrile hydrochloride, 1.71 g of potassium carbonate, and 10 ml of water under ice-cooling, and the mixture was stirred at room temperature for 15 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml x 1). The resulting organic layer was washed with water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 530 mg of the target product as a pale yellow solid. Melting point: 164-166°C.

[0410] Reference Example 8: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole Step 1: Synthesis of 3-oxo-2-(3-(trifluoromethyl)phenoxy)butanal To a mixed solution of 3.00 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one and 30 ml of toluene, 1 mol / l hydrochloric acid was added at room temperature, and the mixture was stirred at 50°C for 7 hours. After completion of the reaction, the reaction mixture was extracted with toluene (30 ml x 1). The obtained organic layer was dehydrated and dried with saturated brine and then with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained solid was washed with 10 ml of diisopropyl ether, and 2.34 g of the target product was obtained as a pale brown solid. Melting point: 115-117°C.

[0411] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 830 mg of 3-oxo-2-(3-(trifluoromethyl)phenoxy)butanal, 500 mg of tert-butylhydrazine hydrochloride, and 8 ml of toluene was stirred at 50°C for 4 hours. After completion of the reaction, the reaction mixture was washed with 10 ml of water and then with 10 ml of a 1 mol / l aqueous sodium hydroxide solution. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 970 mg of the target product as a pale yellow oil. 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).

[0412] Reference Example 9: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate To a mixed solution of 1.00 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid and 10 ml of acetone, 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were added sequentially at room temperature, and the mixture was stirred at the same temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of water was added to the resulting residue, and the mixture was extracted with ethyl acetate (20 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target product as a yellow solid. Melting point: 69-71°C.

[0413] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (Compound No. ii-005) Under a nitrogen atmosphere, 0.50 g of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylboroxine, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane were mixed at room temperature, and 0.10 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride was added thereto, followed by stirring at 100°C for 16 hours. After completion of the reaction, 20 ml of water was added to the reaction mixture, which was then extracted with ethyl acetate (20 ml x 3 times). The mixture was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 10:0 to 9:1) as an eluent to obtain 0.30 g of the desired product as a yellow oil. 1 H-NMR (CDCl3, Me4Si, 400MHz) δ 7.24 (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) Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 39.0 g of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 mL of methanol, a mixed solution of 27.1 g of sodium hydroxide and 100 mL of water was added at room temperature, and the mixture was stirred at 45°C for 16 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the resulting residue was added 50 ml of water, and then 35% by mass hydrochloric acid was added until the pH reached 2, and the precipitated solid was collected by filtration. The resulting solid was dried under reduced pressure and washed with 100 ml of n-hexane to obtain 37.0 g of the target product as a white solid. Melting point: 116-118°C.

[0414] Reference Example 10: Synthesis of ethyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate Step 1: Synthesis of 2-(3-methylphenoxy)acetaldehyde To a mixed solution of 102 ml of 20% by mass hydrochloric acid and 60 ml of acetone, 20 g of 1-(2,2-dimethoxyethoxy)-3-methylbenzene was added dropwise over 2.5 hours at room temperature, and the mixture was stirred at the same temperature for 1 hour. After stirring was completed, 34 ml of 20% by mass hydrochloric acid was added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. After the reaction was completed, 6.6 ml of toluene and 13.4 ml of heptane were added to the reaction mixture, and the aqueous layer was separated by a separation operation. 40 ml of water was added to the obtained organic layer, and the aqueous layer was extracted. The obtained aqueous layers were combined, 12 g of sodium chloride was added, and the mixture was extracted with chloroform (120 ml x 3 times). The obtained organic layer was dehydrated and dried over saturated saline and then anhydrous sodium sulfate, and then about 200 ml of the solvent was distilled off under reduced pressure. 200 ml of toluene was added, and the solvent was again distilled off under reduced pressure to obtain 45 g of a toluene solution containing 14.5 g of the target product. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.88-9.86 (m, 1H), 7.20-7.14 (m, 1H), 6.87-6.67 (m, 3H), 4.56 (s, 2H), 2.33 (s, 3H).

[0415] Step 2: Synthesis of ethyl 4-morpholino-2-oxo-3-(3-methylphenoxy)but-3-enoate To a mixed solution of 12.7 g of morpholine and 300 ml of toluene, 42 g of a toluene solution containing 13.8 g of 2-(3-methylphenyl)acetaldehyde obtained in step 1 was added dropwise over 2 hours under reflux conditions of 20 kPa and 58°C. As the addition was completed, the mixed solution of toluene and water was distilled. After the addition was completed, the mixture was stirred for 1 hour under the same conditions. After the stirring was completed, the initial distillate was combined, and 92 g of a mixed solution of toluene and water was distilled. After ice-cooling to 10°C under the same reduced pressure, the reduced pressure was released. To the reaction mixture, 19.6 g of triethylamine and 26.4 g of ethyl chloroglyoxylate were added dropwise in that order under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. After the stirring was completed, the mixture was stirred overnight at room temperature. After the reaction was completed, 60 ml of water was added to the reaction mixture, and the organic layer was extracted by a separation operation. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:4) as the eluent, to obtain 19 g of the target product as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.53-7.51 (m, 1H), 7.17-7.11 (m, 1H), 6.83-6.70 (m, 3H), 4.38-4.25 (m, 2H), 3.75-3.40 (m, 8H), 1.42-1.22 (m, 6H).

[0416] Step 3: Synthesis of ethyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate To a mixed solution of 5.1 g of ethyl 4-morpholino-2-oxo-3-(3-methylphenoxy)but-3-enoate, 2.2 g of tert-butylhydrazine hydrochloride, and 30 ml of toluene, 1 ml of acetic acid was added, and the mixture was stirred at 80°C for 3 hours. After stirring was completed, 30 ml of ethanol was added to the reaction mixture, and 36 g of a 10% by mass aqueous sodium hydroxide solution was added dropwise under ice cooling. After addition was completed, the mixture was stirred at 40°C for 3 hours. After the reaction was completed, 20 ml of toluene was added to the reaction mixture, and the organic layer was extracted by a separation operation. The obtained organic layer was dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.1 g of the target product as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.20-7.09 (m, 2H), 6.87-6.61 (m, 3H), 4.24-4.16 (m, 2H), 2.31 (s, 3H), 1.71 (s, 9H), 1.15-1.10 (m, 3H).

[0417] The compounds of the present invention can be synthesized in accordance with the above Synthesis Examples and Reference Examples. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 9 are shown in Tables 1 and 2, and examples of the production intermediates produced in the same manner as in Reference Examples 1 to 10 are shown in Tables 3 to 5. However, the compounds and production intermediates of the present invention are not limited to these.

[0418] In the tables, the substituent marked "Me" represents "methyl," and similarly, "Et" represents "ethyl," "nPr" represents "normal propyl," "tBu" represents "tertiary butyl," "iPr" represents "isopropyl," "cPr" represents "cyclopropyl," "cHex" represents "cyclohexyl," "nBu" represents "normal butyl," "iBu" represents "isobutyl," "Ac" represents "acetyl," "Ph" represents "phenyl," and "Bn" represents "benzyl." The symbol "*" indicates that the compound is an oily or resinous compound with no melting point, and "m.p." represents the melting point (unit: °C).

[0419] 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.

[0420] Furthermore, D-1a, D-2a, D-3a, E-2a, E-3a, E-4a, E-5a, E-6a, E-7a, E-8a, E-9a, E-10a, E-11a, E-12a, E-13a, E-16a, E-17a, E-18a, E-19a, E-20a, E-21a, E-24a, E-25a, E-26a, E-27a, E-29a, E-30a, F-2a, F-3a, F-4a, L-1, L-2, L-3, L-4, L-5, L-6, L-7, L-8 and L-9 each represent the following structures. The numbers in the structural formulae above represent the substitution positions, and for example, "4-Me-(E-2a)" in the table represents the following structure: A structural formula without a substituent indicates that the compound is unsubstituted.

[0421] [Table 1] ―――――――――――――――――――――――――――――――― No. G Z 1 R X R Y R 4 R 5m.p.(℃) ―――――――――――――――――――――――――――――――――― 1-001 3-CF3-Ph 3-Me-(E-4a) tBu H H H 129-130 1-002 3-CF3-Ph 5-OH-(E-3a) tBu H H H 197-199 1-003 3-CF3-Ph 5-Me-(E-3a) tBu H H H 119-121 1-004 3-CF3-Ph 5-cPr-(E-3a) tBu H H H 114-116 1-005 3-CF3-Ph 5-Et-(E-3a) tBu H H H 117-119 1-006 3-CF3-Ph 5-iPr-(E-3a) tBu H H H 116-118 1-007 3-CF3-Ph 5-CF3-(E-3a) tBu H H H 126-128 1-008 3-CF3-Ph 5-CF2H-(E-3a) tBu H H H 123-125 1-009 3-CF3-Ph 5-OMe-(E-3a) tBu H H H * 1-010 3-CF3-Ph 5-OEt-(E-3a) tBu H H H * 1-011 3-CF3-Ph 4-Me-(E-2a) tBu H H H * 1-012 3-CF3-Ph 4-cPr-(E-2a) tBu H H H * 1-013 3-CF3-Ph 3-CF3-(E-4a) tBu H H H 125-127 1-014 3-CF3-Ph 4-CF3-(E-2a) tBu H H H 118-120 1-015 3-CF3-Ph 3-Et-(E-4a) tBu H H H 136-138 1-016 3-Me-Ph 3-Me-(E-4a) tBu H H H 109-111 1-017 3-Me-Ph 3-Et-(E-4a) tBu H H H 50-53 1-0183-Me-Ph 5-Me-(E-3a) tBu H H H * 1-019 3-Me-Ph 5-CF3-(E-3a) tBu H H H * 1-020 3-Me-Ph 5-CF2H-(E-3a) tBu H H H * 1-021 3-Me-Ph 5-Et-(E-3a) tBu H H H * 1-022 3-Me-Ph 5-nPr-(E-3a) tBu H H H * 1-023 3-Me-Ph 5-iPr-(E-3a) tBu H H H * 1-024 3-Me-Ph 5-cPr-(E-3a) tBu H H H * 1-025 3-Me-Ph 5-CH2OMe-(E-3a) tBu H H H * 1-026 3-Me-Ph 5-SMe-(E-3a) tBu H H H 109-111 1-027 3-CF3-Ph 5-nPr-(E-5a) tBu H H H 83-86 1-028 3-CF3-Ph 5-Me-(E-5a) tBu H H H 111-113 1-029 3-Me-Ph 5-SH-(E-3a) tBu H H H 162-164 1-030 Ph 5-Me-(E-3a) tBu H H H 90-92 1-031 Ph 5-Et-(E-3a) tBu H H H 94-96 1-032 Ph 5-nPr-(E-3a) tBu H H H 75-77 1-033 Ph 5-iPr-(E-3a) tBu H H H * 1-034 Ph 5-cPr-(E-3a) tBu H H H 117-119 1-035 Ph 5-nBu-(E-3a) tBu H H H 58-60 1-036 Ph 5-CH2OMe-(E-3a) tBu H H H 85-87 1-037 Ph5-CF2H-(E-3a) tBu H H H 85-87 1-038 Ph 5-CF3-(E-3a) tBu H H H 116-118 1-039 Ph 5-SH-(E-3a) tBu H H H 171-173 1-040 Ph 5-SMe-(E-3a) tBu H H H 110-112 1-041 3-Cl-Ph 5-Me-(E-3a) tBu H H H 122-124 1-042 3-Cl-Ph 5-Et-(E-3a) tBu H H H 117-119 1-043 3-Cl-Ph 5-nPr-(E-3a) tBu H H H 109-111 1-044 3-Cl-Ph 5-iPr-(E-3a) tBu H H H 80-82 1-045 3-Cl-Ph 5-cPr-(E-3a) tBu H H H 142-144 1-046 3-Cl-Ph 5-nBu-(E-3a) tBu H H H 105-107 1-047 3-Cl-Ph 5-CH2OMe-(E-3a) tBu H H H 97-99 1-048 3-Cl-Ph 5-CF2H-(E-3a) tBu H H H 117-119 1-049 3-Cl-Ph 5-CF3-(E-3a) tBu H H H 102-104 1-050 3-Cl-Ph 5-SH-(E-3a) tBu H H H 169-171 1-051 3-Cl-Ph 5-SMe-(E-3a) tBu H H H 117-119 1-052 Ph 3-Me-(E-4a) tBu H H H 100-102 1-053 Ph 3-Et-(E-4a) tBu H H H 109-111 1-054 Ph 3-nPr-(E-4a) tBu H H H 77-79 1-055 Ph 3-cPr-(E-4a) tBu H H H131-133 1-056 Ph 3-iPr-(E-4a) tBu H H H 128-130 1-057 Ph 5-Me-(E-5a) tBu H H H 131-133 1-058 Ph 5-Et-(E-5a) tBu H H H 128-130 1-059 Ph 5-nPr-(E-5a) tBu H H H 100-102 1-060 Ph 5-iPr-(E-5a) tBu H H H 97-99 1-061 Ph 5-cPr-(E-5a) tBu H H H 127-129 1-062 Ph 5-CH2OMe-(E-5a) tBu H H H 95-97 1-063 3-Cl-Ph 3-Me-(E-4a) tBu H H H 115-117 1-064 3-Cl-Ph 3-Et-(E-4a) tBu H H H 117-119 1-065 3-Cl-Ph 3-nPr-(E-4a) tBu H H H 97-99 1-066 3-Cl-Ph 3-cPr-(E-4a) tBu H H H 141-143 1-067 3-Cl-Ph 3-iPr-(E-4a) tBu H H H 84-86 1-068 3-Cl-Ph 5-Me-(E-5a) tBu H H H 112-114 1-069 3-Cl-Ph 5-Et-(E-5a) tBu H H H 149-151 1-070 3-Cl-Ph 5-nPr-(E-5a) tBu H H H 127-129 1-071 3-Cl-Ph 5-iPr-(E-5a) tBu H H H 115-117 1-072 3-Cl-Ph 5-cPr-(E-5a) tBu H H H 169-171 1-073 3-Cl-Ph 5-CH2OMe-(E-5a) tBu H H H 127-129 1-074 3-CF3-PhE-4a tBu H H H * 1-075 3-Me-Ph 5-SH-(E-3a) tBu H H H 162-164 1-076 3-Me-Ph 5-CH2OEt-(E-3a) tBu H H H * 1-077 3-Me-Ph 3-nPr-(E-4a) tBu H H H * 1-078 3-Me-Ph 3-cPr-(E-4a) tBu H H H * 1-079 3-Me-Ph 2-Me-(E-12a) tBu H H H * 1-080 3-CF3-Ph 3-nPr-(E-4a) tBu H H H 117-119 1-081 3-CF3-Ph 3-cPr-(E-4a) tBu H H H 135-137 1-082 3-Me-Ph E-25a tBu H H H * 1-083 3-Me-Ph 5-Me-(E-7a) tBu H H H * 1-084 3-Me-Ph E-12a tBu H H H 98-99 1-085 3-Me-Ph E-13a tBu H H H * 1-086 3-Me-Ph 2-Me-(E-13a) tBu H H H 91-93 1-087 3-Me-Ph 3,5-Me2-(E-7a) tBu H H H * 1-088 3-Me-Ph E-26a tBu H H H * 1-089 3-Me-Ph 1-Me-(E-9a) tBu H H H 113-115 1-090 3-Me-Ph 5-Cl-(E-17a) tBu H H H * 1-091 3-Me-Ph 1-iPr-(E-21a) tBu H H H * 1-092 3-Me-Ph 2-cPr-(E-11a) tBu H H H * 1-093 3-Me-Ph 1,2-Me2-(E-16a) tBu H H H * 1-0943-CF3-Ph 2-Me-(E-12a) tBu H H H * 1-095 3-Me-Ph 5-C(=NOMe)Me-(E-3a) tBu H H H * 1-096 3-CF3-Ph 5-C(=NOMe)Me-(E-3a) tBu H H H * 1-097 3-Me-Ph 5-CH(OMe)Me-(E-3a) tBu H H H 60-62 1-098 3-CF3-Ph 5-CH(OMe)Me-(E-3a) tBu H H H * 1-099 3-CF3-Ph 2-Et-(E-12a) tBu H H H * 1-100 3-CF3-Ph 2-iPr-(E-12a) tBu H H H * 1-101 3-CF3-Ph 2-cPr-(E-12a) tBu H H H * 1-102 3-CF3-Ph 2-CH2OMe-(E-12a) tBu H H H * 1-103 3-Me-Ph 2-Et-(E-12a) tBu H H H * 1-104 3-Me-Ph 2-iPr-(E-12a) tBu H H H * 1-105 3-Me-Ph 2-cPr-(E-12a) tBu H H H * 1-106 3-Me-Ph 2-CH2OMe-(E-12a) tBu H H H * 1-107 3-CF3-Ph 5-CCl3-(E-3a) tBu H H H 149-151 1-108 3-Me-Ph E-24a tBu H H H * 1-109 3-Me-Ph 1-Et-(E-9a) tBu H H H * 1-110 3-Me-Ph 1-CH2OMe-(E-9a) tBu H H H * 1-111 3-CF3-Ph 1-Me-(E-9a) tBu H H H * 1-112 3-CF3-Ph 1-CH2OMe-(E-9a) tBu H H H * 1-113 3-CF3-Ph1-Et-(E-9a) tBu H H H * 1-114 3-CF3-Ph 5-CH2OMe-(E-3a) tBu H H H * 1-115 3-CF3-Ph 5-SH-(E-3a) tBu H H H * 1-116 3-CF3-Ph 5-SMe-(E-3a) tBu H H H * 1-117 3-CF3-Ph 5-Et-(E-5a) tBu H H H 116-118 1-118 3-CF3-Ph 5-cPr-(E-5a) tBu H H H * 1-119 3-CF3-Ph 5-CH2OMe-(E-5a) tBu H H H * 1-120 3-CF3-Ph E-27 tBu H H H * 1-121 3-CF3-Ph 3-Me-(E-18a) tBu H H H * 1-122 3-Me-Ph 3-Me-(E-18a) tBu H H H 117-119 1-123 3-Me-Ph 5-Et-(E-5a) tBu H H H * 1-124 3-Me-Ph 5-cPr-(E-5a) tBu H H H * 1-125 3-Me-Ph 5-Me-(E-5a) tBu H H H 79-81 1-126 3-Me-Ph 5-nPr-(E-5a) tBu H H H * 1-127 3-CF3-Ph 2-Me-(E-10a) tBu H H H 144-146 1-128 3-CF3-Ph 5-NHcHex-(E-3a) tBu H H H * 1-129 3-CF3-Ph 5-(D-3a)-(E-3a) tBu H H H * 1-130 3-CF3-Ph 5-C(O)(D-3a)-(E-3a) tBu H H H * 1-131 3-CF3-Ph 1-iPr-(E-9a) tBu H H H * 1-132 3-Me-Ph 1-iPr-(E-9a)tBu H H H * 1-133 3-CF3-Ph 5-NH2-(E-3a) tBu H H H 192-194 1-134 3-CF3-Ph 5-N(Me)C(O)Me-(E-3a) tBu H H H 169-171 1-135 3-CF3-Ph 5-C(O)NHMe-(E-3a) tBu H H H * 1-136 3-Me-Ph 5-(D-3a)-(E-3a) tBu H H H * 1-137 3-Me-Ph 5-C(O)(D-3a)-(E-3a) tBu H H H * 1-138 3-CF3-Ph 5-N(Me)SO2Me-(E-3a) tBu H H H * 1-139 3-Me-Ph 5-CH2OMe-(E-5a) tBu H H H * 1-140 3-CF3-Ph 5-C(O)NHnBu-(E-3a) tBu H H H * 1-141 3-CF3-Ph 3-NMe2-(E-4a) tBu H H H 144-146 1-142 3-CF3-Ph 5-NHC(O)Me-(E-3a) tBu H H H 171-173 1-143 3-Me-Ph 5-C(O)NHMe-(E-3a) tBu H H H * 1-144 3-Me-Ph 5-C(O)NHEt-(E-3a) tBu H H H * 1-145 3-Me-Ph 5-NH2-(E-3a) tBu H H H 174-176 1-146 3-Me-Ph 5-NHEt-(E-3a) tBu H H H * 1-147 3-Me-Ph 5-C(O)NHiPr-(E-3a) tBu H H H * 1-148 3-CF3-Ph 5-cPr-(E-19a) tBu H H H 128-130 1-149 3-Me-Ph 5-cPr-(E-19a) tBu H H H * 1-150 3-Me-Ph 5-C(O)NH2-(E-3a) tBu H H H * 1-1513-Me-Ph 5-NHiPr-(E-3a) tBu H H H * 1-152 3-Me-Ph 5-NHC(O)Me-(E-3a) tBu H H H * 1-153 3-Me-Ph 5-C(O)NHcHex-(E-3a) tBu H H H * 1-154 3-Me-Ph 5-C(O)NHtBu-(E-3a) tBu H H H * 1-155 3-Me-Ph 5-NHcHex-(E-3a) tBu H H H * 1-156 3-Me-Ph 5-NHMe-(E-3a) tBu H H H * 1-157 3-Me-Ph 5-(D-1a)-(E-3a) tBu H H H * 1-158 3-Me-Ph 5-C(O)(D-1a)-(E-3a) tBu H H H * 1-159 3-Me-Ph 5-CH2OC(O)Me-(E-3a) tBu H H H * 1-160 3-Me-Ph 5-CH2OH-(E-3a) tBu H H H 55-57 1-161 3-Me-Ph 5-NHC(O)NEt2-(E-3a) tBu H H H * 1-162 3-Me-Ph 5-C(O)N(Me)Et-(E-3a) tBu H H H * 1-163 3-Me-Ph 5-(D-2a)-(E-3a) tBu H H H * 1-164 3-Me-Ph 5-NHC(O)OMe-(E-3a) tBu H H H * 1-165 3-Me-Ph 5-C(O)(D-2a)-(E-3a) tBu H H H * 1-166 3-Me-Ph 5-N(Me)Et-(E-3a) tBu H H H * 1-167 3-Me-Ph 5-NHSO2Me-(E-3a) tBu H H H * 1-168 3-Me-Ph 5-NMe2-(E-3a) tBu H H H 132-135 1-169 3-Me-Ph 5-N(OMe)Me-(E-3a) tBu H H H * 1-1703-Me-Ph 5-NHC(O)NMe2-(E-3a) tBu H H H * 1-171 3-Me-Ph 5-C(O)NMe2-(E-3a) tBu H H H * 1-172 3-CF3-Ph 5-C(O)NMe2-(E-3a) tBu H H H 140-142 1-173 Ph 5-CH(SMe)Me-(E-3a) tBu H H H 1-174 3-CF3-Ph 5-CH(SMe)Me-(E-3a) tBu H H H 102-104 1-175 Ph 5-CH(SOMe)Me-(E-3a) tBu H H H 49-51 1-176 3-CF3-Ph 5-CH(SOMe)Me-(E-3a) tBu H H H 121-123 1-177 Ph 5-CH(SO2Me)Me-(E-3a) tBu H H H 52-54 1-178 3-CF3-Ph 5-CH(SO2Me)Me-(E-3a) tBu H H H 146-148 1-179 Ph 5-CH2SMe-(E-3a) tBu H H H 74-76 1-180 3-CF3-Ph 5-CH2SMe-(E-3a) tBu H H H * 1-181 Ph 5-CH2SOMe-(E-3a) tBu H H H 54-56 1-182 3-CF3-Ph 5-CH2SOMe-(E-3a) tBu H H H 142-144 1-183 Ph 5-CH2SO2Me-(E-3a) tBu H H H 151-153 1-184 3-CF3-Ph 5-CH2SO2Me-(E-3a) tBu H H H 130-132 1-185 Ph 5-CH(SEt)Me-(E-3a) tBu H H H * 1-186 3-CF3-Ph 5-CH(SEt)Me-(E-3a) tBu H H H 75-77 1-187 Ph 5-CH(SOEt)Me-(E-3a) tBu H H H * 1-188 3-CF3-Ph5-CH(SOEt)Me-(E-3a) tBu H H H 77-79 1-189 Ph 5-CH(SO2Et)Me-(E-3a) tBu H H H * 1-190 3-CF3-Ph 5-CH(SO2Et)Me-(E-3a) tBu H H H 95-97 1-191 Ph 5-CH2SEt-(E-3a) tBu H H H 80-82 1-192 3-CF3-Ph 5-CH2SEt-(E-3a) tBu H H H 80-82 1-193 Ph 5-CH2SOEt-(E-3a) tBu H H H * 1-194 3-CF3-Ph 5-CH2SOEt-(E-3a) tBu H H H * 1-195 Ph 5-CH2SO2Et-(E-3a) tBu H H H 115-117 1-196 3-CF3-Ph 5-CH2SO2Et-(E-3a) tBu H H H 65-67 1-197 Ph 5-CH(SMe)Et-(E-3a) tBu H H H * 1-198 3-CF3-Ph 5-CH(SMe)Et-(E-3a) tBu H H H * 1-199 Ph 5-CH(SOMe)Et-(E-3a) tBu H H H * 1-200 3-CF3-Ph 5-CH(SOMe)Et-(E-3a) tBu H H H * 1-201 Ph 5-CH(SO2Me)Et-(E-3a) tBu H H H 99-101 1-202 3-CF3-Ph 5-CH(SO2Me)Et-(E-3a) tBu H H H 120-122 1-203 Ph 5-CH(SEt)Et-(E-3a) tBu H H H 100-102 1-204 3-CF3-Ph 5-CH(SEt)Et-(E-3a) tBu H H H 72-74 1-205 Ph 5-CH(SOEt)Et-(E-3a) tBu H H H 130-132 1-206 3-CF3-Ph5-CH(SOEt)Et-(E-3a) tBu H H H * 1-207 Ph 5-CH(SO2Et)Et-(E-3a) tBu H H H * 1-208 3-CF3-Ph 5-CH(SO2Et)Et-(E-3a) tBu H H H * 1-209 Ph 5-CH2tBu-(E-3a) tBu H H H * 1-210 3-CF3-Ph 5-CH2tBu-(E-3a) tBu H H H * 1-211 Ph 5-cHex-(E-3a) tBu H H H * 1-212 3-CF3-Ph 5-cHex-(E-3a) tBu H H H * 1-213 Ph 5-Ph-(E-3a) tBu H H H * 1-214 3-CF3-Ph 5-Ph-(E-3a) tBu H H H 117-119 1-215 Ph 5-CH(NHAc)Me-(E-3a) tBu H H H 89-91 1-216 3-CF3-Ph 5-CH(NHAc)Me-(E-3a) tBu H H H * 1-217 Ph 5-CH2NHAc-(E-3a) tBu H H H 171-173 1-218 3-CF3-Ph 5-CH2NHAc-(E-3a) tBu H H H 100-102 1-219 3-Me-Ph 5-CH2tBu-(E-3a) tBu H H H 70-72 1-220 3-Me-Ph 5-cHex-(E-3a) tBu H H H 55-57 1-221 3-Me-Ph 5-Ph-(E-3a) tBu H H H 112-114 1-222 3-Me-Ph 5-CH(NHAc)Me-(E-3a) tBu H H H 1-223 3-Me-Ph 5-CH2NHAc-(E-3a) tBu H H H 1-224 Ph 5-NMe2-(E-3a) tBu H H H * 1-225 3-CF3-Ph5-NMe2-(E-3a) tBu H H H 1-226 Ph 5-N(OMe)Me-(E-3a) tBu H H H * 1-227 3-CF3-Ph 5-N(OMe)Me-(E-3a) tBu H H H 1-228 Ph 5-NHOMe-(E-3a) tBu H H H 1-229 3-CF3-Ph 5-NHOMe-(E-3a) tBu H H H 1-230 Ph 5-(D-1a)-(E-3a) tBu H H H 94-96 1-231 3-CF3-Ph 5-(D-1a)-(E-3a) tBu H H H 1-232 Ph 5-(D-2a)-(E-3a) tBu H H H 130-132 1-233 3-CF3-Ph 5-(D-2a)-(E-3a) tBu H H H 115-117 1-234 Ph 5-N(Me)SO2Me-(E-3a) tBu H H H 1-235 3-CF3-Ph 5-N(Me)SO2Me-(E-3a) tBu H H H 1-236 Ph 5-N(Et)SO2Me-(E-3a) tBu H H H 1-237 3-CF3-Ph 5-N(Et)SO2Me-(E-3a) tBu H H H 1-238 Ph 5-N(L-1)SO2Me-(E-3a) tBu H H H 1-239 3-CF3-Ph 5-N(L-1)SO2Me-(E-3a) tBu H H H 1-240 Ph 5-N(L-2)SO2Me-(E-3a) tBu H H H 1-241 3-CF3-Ph 5-N(L-2)SO2Me-(E-3a) tBu H H H 1-242 Ph 5-N(Me)Et-(E-3a) tBu H H H 82-84 1-243 3-CF3-Ph 5-N(Me)Et-(E-3a) tBu H H H 1-244 Ph5-C(O)NHMe-(E-3a) tBu H H H 1-245 3-CF3-Ph 5-C(O)NHMe-(E-3a) tBu H H H 1-246 Ph 5-C(O)NHEt-(E-3a) tBu H H H 1-247 3-CF3-Ph 5-C(O)NHEt-(E-3a) tBu H H H 1-248 Ph 5-C(O)(D-1a)-(E-3a) tBu H H H 1-249 3-CF3-Ph 5-C(O)(D-1a)-(E-3a) tBu H H H 55-57 1-250 Ph 5-C(O)(D-3a)-(E-3a) tBu H H H 1-251 3-CF3-Ph 5-C(O)(D-3a)-(E-3a) tBu H H H 1-252 Ph 5-C(O)(D-2a)-(E-3a) tBu H H H 1-253 3-CF3-Ph 5-C(O)(D-2a)-(E-3a) tBu H H H 1-254 Ph 5-C(O)N(Me)Et-(E-3a) tBu H H H 1-255 3-CF3-Ph 5-C(O)N(Me)Et-(E-3a) tBu H H H 1-256 Ph 5-CCl3-(E-3a) tBu H H H 1-257 Ph 5-N(Me)Ac-(E-3a) tBu H H H 1-258 3-CF3-Ph 5-N(Me)Ac-(E-3a) tBu H H H 1-259 Ph 5-CH(OEt)Me-(E-3a) tBu H H H * 1-260 3-Me-Ph 5-NHSO2CF3-(E-3a) tBu H H H * 1-261 3-Me-Ph 5-CH(OEt)Me-(E-3a) tBu H H H * 1-262 3-Me-Ph 5-CH(OEt)Et-(E-3a) tBu H H H * 1-2633-Me-Ph 5-CH(OH)Et-(E-3a) tBu H H H 139-141 1-264 3-Me-Ph 5-(L-3)-(E-3a) tBu H H H * 1-265 3-Me-Ph 5-NHC(O)NHMe-(E-3a) tBu H H H * 1-266 3-Me-Ph 5-C(O)NHOH-(E-3a) tBu H H H * 1-267 3-Me-Ph 5-CH(SO2Me)Me-(E-3a) tBu H H H * 1-268 3-Me-Ph 5-CH(SO2Et)Me-(E-3a) tBu H H H * 1-269 3-Me-Ph 5-CF2Cl-(E-3a) tBu H H H 82-84 1-270 Ph 5-CF2Cl-(E-3a) tBu H H H 112-114 1-271 3-Me-Ph 5-N(Me)C(O)Me-(E-3a) tBu H H H * 1-272 3-Me-Ph 5-NHOH-(E-3a) tBu H H H * 1-273 3-Me-Ph 5-CH(SMe)Me-(E-3a) tBu H H H * 1-274 3-Me-Ph 5-CH(SEt)Me-(E-3a) tBu H H H * 1-275 3-Me-Ph 5-C(=NOMe)Et-(E-3a) tBu H H H * 1-276 3-Me-Ph 5-CH2SMe-(E-3a) tBu H H H * 1-277 3-Me-Ph 5-CH2SEt-(E-3a) tBu H H H * 1-278 3-Me-Ph 5-CH2SOMe-(E-3a) tBu H H H * 1-279 3-Me-Ph 5-CH2SOEt-(E-3a) tBu H H H * 1-280 3-Me-Ph 5-CH2SO2Me-(E-3a) tBu H H H * 1-281 3-Me-Ph 5-CH2SO2Et-(E-3a) tBu H H H *1-282 3-Me-Ph 5-NHOMe-(E-3a) tBu H H H * 1-283 3-Me-Ph 5-CH(Cl)Me-(E-3a) tBu H H H * 1-284 3-Me-Ph 5-CH2Br-(E-3a) tBu H H H 95-97 1-285 3-Me-Ph 5-CH2CN-(E-3a) tBu H H H * 1-286 3-Me-Ph 5-N(Me)SO2Me-(E-3a) tBu H H H 132-134 1-287 3-CF3-Ph 5-tBu-(E-3a) tBu H H H 93-95 1-288 3-Me-Ph 5-tBu-(E-3a) tBu H H H * 1-289 Ph 5-tBu-(E-3a) tBu H H H * 1-290 3-CF3-Ph 3-tBu-(E-4a) tBu H H H 123-124 1-291 3-Me-Ph 3-tBu-(E-4a) tBu H H H * 1-292 Ph 3-tBu-(E-4a) tBu H H H * 1-293 3-CF3-Ph 3-iBu-(E-4a) tBu H H H * 1-294 3-Me-Ph 3-iBu-(E-4a) tBu H H H * 1-295 Ph 3-iBu-(E-4a) tBu H H H * 1-296 3-CF3-Ph 5-Et-(E-3a) iPr H H H * 1-297 Ph 5-Et-(E-3a) iPr H H H * 1-298 3-CF3-Ph 5-Et-(E-3a) F-2a H H H * 1-299 Ph 5-Et-(E-3a) F-2a H H H 123-124 1-300 Ph 5-Et-(E-3a) Ph H H H 139-140 1-301 3-CF3-Ph5-CH(OMe)Et-(E-3a) tBu H H H * 1-302 3-CF3-Ph 5-(L-4)-(E-3a) tBu H H H * 1-303 3-Me-Ph 5-CH(OMe)Et-(E-3a) tBu H H H * 1-304 3-Me-Ph 5-(L-4)-(E-3a) tBu H H H * 1-305 Ph 5-CH(OMe)Et-(E-3a) tBu H H H * 1-306 Ph 5-(L-4)-(E-3a) tBu H H H * 1-307 3-Me-Ph 5-CH(=NOMe)-(E-3a) tBu H H H * 1-308 3-CF3-Ph E-3a tBu H H H * 1-309 3-Me-Ph E-3a tBu H H H * 1-310 Ph E-3a tBu H H H 112-114 1-311 3-Me-Ph 5-CH2NHC(O)Ph-(E-3a) tBu H H H 147-149 1-312 3-Me-Ph 5-CH2NHC(O)Me-(E-3a) tBu H H H 146-148 1-313 3-Me-Ph 5-(L-5)-(E-3a) tBu H H H * 1-314 3-CF3-Ph 5-Et-(E-3a) Me H H H * 1-315 3-Me-Ph 3-Me-(E-8a) tBu H H H 107-109 1-316 3-CF3-Ph 3-Me-(E-8a) tBu H H H 139-141 1-317 3-Me-Ph 5-Me-(E-6a) tBu H H H 121-122 1-318 3-CF3-Ph 5-Me-(E-6a) tBu H H H 124-125 1-319 Ph 5-Me-(E-6a) tBu H H H 106-107 1-3203-Me-Ph 2-Me-(E-29a) tBu H H H * 1-321 Ph 2-Me-(E-29a) tBu H H H * 1-322 3-CF3-Ph 2-Me-(E-29a) tBu H H H * 1-323 3-Me-Ph 2-Et-(E-29a) tBu H H H * 1-324 Ph 2-Et-(E-29a) tBu H H H * 1-325 3-CF3-Ph 2-Et-(E-29a) tBu H H H * 1-326 3-Me-Ph 5-(L-6)-(E-3a) tBu H H H 113-114 1-327 Ph 4-Me-(E-30a) tBu H H H 124-126 1-328 3-Me-Ph 4-Me-(E-30a) tBu H H H 152-154 1-329 3-CF3-Ph 4-Me-(E-30a) tBu H H H 157-159 1-330 3-Me-Ph 5-CFH2-(E-3a) tBu H H H * 1-331 Ph 5-CFH2-(E-3a) tBu H H H * 1-332 3-CF3-Ph 5-CFH2-(E-3a) tBu H H H 120-122 1-333 Ph 5-CH2NMeSO2Me-(E-3a) tBu H H H 132-134 1-334 3-Me-Ph 5-CH2NMeSO2Me-(E-3a) tBu H H H 132-134 1-335 3-CF3-Ph 5-CH2NMeSO2Me-(E-3a) tBu H H H 132-134 1-336 Ph 3-OMe-(E-4a) tBu H H H * 1-337 3-Me-Ph 3-OMe-(E-4a) tBu H H H * 1-338 3-Me-Ph 5-(L-7)-(E-3a) tBu H H H * 1-3393-Me-Ph 5-CH(Me)Ph-(E-3a) tBu H H H * 1-340 3-CF3-Ph 3-OMe-(E-4a) tBu H H H 149-151 1-341 3-Me-Ph 2-nPr-(E-29a) tBu H H H * 1-342 Ph 2-nPr-(E-29a) tBu H H H * 1-343 3-CF3-Ph 2-nPr-(E-29a) tBu H H H * 1-344 3-Me-Ph 2-iPr-(E-29a) tBu H H H * 1-345 Ph 2-iPr-(E-29a) tBu H H H * 1-346 3-CF3-Ph 2-iPr-(E-29a) tBu H H H * 1-347 Ph 5-(D-3a)-(E-3a) tBu H H H * 1-348 3-CF3-Ph 5-(L-8)-(E-3a) tBu H H H * 1-349 3-CF3-Ph 5-(L-9)-(E-3a) tBu H H H * ―――――――――――――――――――――――――――――――――― [Table 2] ―――――――――――――――――――――――――――――――――― No. G Z 1 Z 2 R X R Y R 4 R 5m.p. (°C) ――――――――――――――――――――――――――――――――― 2-001 3-CF3-Ph 1-Me-(E-21a) OMe tBu H H H * 2-002 3-CF3-Ph 1-Me-(E-20a) OMe tBu H H H * 2-003 3-Me-Ph 3-Me-(E-4a) OMe tBu H H H * 2-004 3-Me-Ph 3-cPr-(E-4a) OMe tBu H H H * ――――――――――――――――――――――――――――――――― [Table 3] ――――――――――――――――――――――――――――― No. G R X R Ym.p.(℃) ――――――――――――――――――――――――――――― i-001 3-CF3-Ph Ph H 177-179 i-002 3-CF3-Ph tBu H 120-124 i-003 3-CF3-Ph Bn H 124-126 i-004 3-CF3-Ph Me H i-005 3-CF3-Ph 2-Cl-Ph H i-006 3-CF3-Ph 3-Cl-Ph H 177-180 i-007 3-CF3-Ph 4-Cl-Ph H i-008 2-F-3-cPr-Ph Ph H i-009 3-Br-Ph tBu H 95-102 i-010 2-F-3-Cl-Ph tBu H 153-155 i-011 Ph tBu H 142-144 i-012 2-CF3-Ph tBu H 139-141 i-013 4-CF3-Ph tBu H 131-133 i-014 3-F-Ph tBu H 154-156 i-015 2-Cl-Ph tBu H 166-168 i-016 3-Cl-Ph tBu H 122-124 i-017 4-Cl-Ph tBu H 119-121 i-018 2,3-Cl2-Ph tBu H 160-162 i-019 2,4-Cl2-Ph tBu H 143-145 i-020 3,4-Cl2-Ph tBu H 143-145 i-021 3-I-Ph tBu H 121-123 i-022 3-OMe-Ph tBu H 145-147 i-023 3-OCF3-Ph tBu H 112-114 i-024 3-NMe2-Ph tBu H 126-130 i-025 3-CF3-Ph iPr H 177-179 i-026 Ph iPr H 142-144 i-027 Ph Ph H 176-178 i-028 2-F-3-Br-Ph tBu H i-029 2-F-3-cPr-Ph tBu H i-030 3-CF3-Ph F-2a H 115-117 i-031 3-CF3-Ph F-3a H 191-193 i-032 3-CF3-Ph F-4a H 166-168 i-033 Ph F-2a H 121-123 i-034 Ph F-3a H 187-189 i-035 Ph F-4a H 153-155 i-036 3-Me-Ph tBu H 116-118 i-037 3-SMe-Ph tBu H 117-119 i-038 3-CF3-Ph tBu Br 126-128 i-039 3-Me-Ph tBu Cl 105-107 i-040 2-F-Ph tBu H 118-120 i-041 2,3-F2-Ph tBu H 129-131 i-042 2-F-3-OMe-Ph tBu H 171-174 ――――――――――――――――――――――――――――― [Table 4], ―――――――――――――――――――――――――――― No. G R X R Y R 101 mp(℃) ―――――――――――――――――――――――――― ii-001 3-CF3-Ph tBu H Me ii-002 2-F-3-Br-Ph tBu H Me ii-003 2-F-3-cPr-Ph tBu H Me ii-004 3-Br-Ph tBu H Me 69-71 ii-005 3-Me-Ph tBu H Me * ―――――――――――――――――――――――――― [Table 5] ―――――――――――――――――――――――――――――――― No. G Z 1 R X R Y R 4 R 5 mp(℃) ------------------------------------------------ ia-001 Ph C(=NOH)NH2 tBu H H H 142-144 ia-002 3-Cl-Ph C(=NOH)NH2 tBu H H H 169-171 ia-003 Ph C(O)OMe tBu H H H ia-004 3-Cl-Ph C(O)OMe tBu H H H ia-005 Ph C(O)OH tBu H H H 73-76 ia-006 3-Cl-Ph C(O)OH tBu H H H 142-144 ---------------------------------------------------------------- Among the compounds of the present invention shown in Tables 1 and 2, for compounds without melting points １The H-NMR data are shown in Table 6. The following data were measured in deuterated chloroform, with "#1" indicating that the measurement was performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL), and similarly, "#2" indicating that the measurement was performed at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).

[0422] [Table 6] ------------------------------------------------------------------ No. 1H-NMR (CDCl3, Me4Si) ―――――――――――――――――――――――――――――――――― 1-009(#1):δ7.44-7.40 (m, 3H), 7.39-7.30 (m, 3H), 7.26-7.22 (m, 1H), 7.16 (s, 1H), 7.14-7.07 (m, 1H), 6.60-6.50 (m, 1H), 3.67 (q, J = 6.8 Hz, 2H), 2.88 (t, J = 7.1 Hz, 2H), 3.27 (s, 3H), 1.72 (s, 9H)。 1-010(#1):δ7.48-7.30 (m, 6H), 7.26-7.23 (m, 1H), 7.16 (s, 1H), 7.13-7.07 (m, 1H), 6.55-6.45 (m, 1H), 3.74-3.62 (m, 4H), 2.88 (t, J = 7.1 Hz, 2H), 1.72 (s, 9H), 1.24 (t, J = 7.2 Hz, 3H)。 1-011(#1):δ7.76 (d, J = 8.1 Hz, 2H), 7.40-7.27 (m, 2H), 7.25-7.13 (m, 4H), 7.08-7.01 (m, 1H), 6.85 (s, 1H), 6.50-6.40 (m, 1H), 3.66 (q, J = 6.7 Hz, 2H), 2.83 (t, J = 6.9 Hz, 2H), 2.98 (s, 3H), 1.72 (s, 9H)。 1-012(#1):δ7.73 (d, J = 8.7 Hz, 2H), 7.40-7.28 (m, 2H), 7.24-7.20 (m, 1H), 7.19-7.12 (m, 3H), 7.07-7.01 (m, 1H), 6.80 (s, 1H), 6.48-6.38 (m, 1H), 3.65 (q, J = 6.5 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 2.14-1.95 (m, 1H), 1.72 (s, 9H), 0.99-0.93 (m, 4H)。1-018(#1):δ7.89 (d, J = 8.4 Hz, 2H), 7.24 (d, J = 8.1 Hz, 2H), 7.19-7.10 (m, 2H), 6.92-6.85 (m, 1H), 6.77-6.68 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H), 2.86 (t, J = 7.1 Hz, 2H), 2.64 (s, 3H), 2.29 (s, 3H), 1.72 (s, 9H)。 1-019(#1):δ7.90 (d, J = 8.4 Hz, 2H), 7.28 (d, J = 8.1 Hz, 2H), 7.19-7.11 (m, 1H), 7.09 (s, 1H), 6.90-6.84 (m, 1H), 6.78-6.68 (m, 3H), 3.69 (q, J = 6.5 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。 1-020(#1):δ7.91 (d, J = 8.1 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 7.19-7.09 (m, 2H), 6.90-6.84 (m, 1H), 6.86 (t, J = 52.5 Hz, 1H), 6.78-6.68 (m, 3H), 3.68 (q, J = 6.6 Hz, 2H), 2.88 (t, J = 6.9 Hz, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。 1-021(#2):δ7.91 (d, J = 6.0 Hz, 2H), 7.24 (d, J = 6.3 Hz, 2H), 7.19-7.15 (m, 1H), 7.12 (s, 1H), 6.91-6.86 (m, 1H), 6.78-6.69 (m, 3H), 3.67 (q, J = 4.9 Hz, 2H), 2.98 (q, J = 6.0 Hz, 2H), 2.86 (t, J = 5.3 Hz, 2H), 2.29 (s, 3H), 1.72 (s, 9H), 1.46 (t, J = 5.6 Hz, 3H)。<h2 style=";text-align:left;direction:ltr">1-022(#1):δ7.90 (d, J = 8.1 Hz, 2H), 7.23 (d, J = 8.1 Hz, 2H), 7.20-7.09 (m, 2H), 6.91-6.84 (m, 1H), 6.78-6.68 (m, 3H), 3.66 (q, J = 6.3 Hz, 2H), 2.96-2.82 (m, 4H), 2.29 (s, 3H), 2.00-1.84 (m, 2H), 1.73 (s, 9H), 1.07 (t, J = 7.5 Hz, 3H)。 1-023(#1):δ7.90 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.7 Hz, 2H), 7.19-7.09 (m, 2H), 6.91-6.85 (m, 1H), 6.78-6.67 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H), 3.28 (sep, J = 7.1 Hz, 1H), 2.86 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H), 1.46 (d, J = 7.2 Hz, 6H)。 1-024(#1): δ7.86 (d, J = 8.1 Hz, 2H), 7.22 (d, J = 8.1 Hz, 2H), 7.19-7.09 (m, 2H), 6.92-6.85 (m, 1H), 6.80-6.66 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H), 2.85 (t, J = 6.9 Hz, 2H), 2.30-2.20 (m, 4H), 1.72 (s, 9H), 1.35-1.20 (m, 4H)。 1-025(#1):δ7.93 (d, J = 7.8 Hz, 2H), 7.26 (d, J = 8.1 Hz, 2H), 7.19-7.09 (m, 2H), 6.91-6.85 (m, 1H), 6.78-6.68(m, 3H), 4.74 (s, 2H), 3.67 (q, J = 6.6 Hz, 2H), 3.56 (s, 3H), 2.86 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。1-033(#1):δ7.93-7.87 (m, 2H), 7.82-7.18 (m, 4H), 7.12 (s, 1H), 7.09-7.03 (m, 1H), 6.95-6.87 (m, 2H), 6.88-6.56 (m, 1H), 3.70-3.62 (m, 2H), 3.34-3.21 (m, 1H), 2.84 (t, J = 7.0 Hz, 2H), 1.73 (s, 9H), 1.47 (d, J = 6.8 Hz, 6H)。 1-074(#1):δ8.47 (s, 1H), 8.00-7.94 (m, 2H), 7.43-7.36 (m, 1H), 7.35-7.28 (m, 3H), 7.19 (s, 1H), 7.14 (s, 1H), 7.10-7.05 (m, 1H), 6.56-6.48 (m, 1H), 3.753.64 (m, 2H), 2.94-2.86 (m, 2H), 1.72 (s, 9H)。 1-076(#2):δ7.93 (d, J = 8.4 Hz, 2H), 7.25 (d, J = 8.1 Hz, 2H), 7.16 (t, J = 7.9 Hz, 1H), 7.12 (s, 1H), 6.89 (d, J = 7.7 Hz, 1H), 6.75-6.71 (m, 3H), 4.79 (s, 2H), 3.72-3.67 (m, 4H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 1.74 (d, J = 11.7 Hz, 9H), 1.31 (t, J = 7.0 Hz, 3H)。 1-077(#1):δ7.96-7.86 (m, 2H), 7.32-7.21 (m, 2H), 7.19-7.07 (m, 2H), 6.91-6.66 (m, 4H), 3.76-3.62 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.77 (t, J = 7.5 Hz, 2H), 2.28 (s, 3H), 1.93-1.79 (m, 2H), 1.73 (s, 9H), 1.04 (t, J = 7.3 Hz, 3H)。1-078(#1):δ7.94-7.78 (m, 2H), 7.32-7.19 (m, 2H), 7.19-7.05 (m, 2H), 6.94-6.82 (m, 1H), 6.81-6.61 (m, 3H), 3.76-3.59 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 2.22-2.08 (m, 1H), 1.73 (s, 9H), 1.18-1.02 (m, 4H)。 1-079(#1):δ7.73-7.68 (m, 2H), 7.23-7.11 (m, 5H), 6.91-6.86 (m, 1H), 6.78-6.64 (m, 3H), 3.69-3.60 (m, 2H), 2.86-2.79 (m, 2H), 2.77 (s, 3H), 2.27 (s, 3H), 1.73 (s, 9H)。 1-082(#1):δ8.68 (s, 1H), 8.61 (s, 1H), 7.41-7.35 (m, 2H), 7.23-7.07 (m, 4H), 6.93-6.86 (m, 1H), 6.77-6.68 (m, 3H), 3.71-3.61 (m, 2H), 2.90-2.77 (m, 2H), 2.27 (s, 3H), 1.72 (s, 9H)。 1-083(#1):δ8.34 (s, 1H), 7.19-7.07 (m, 6H), 6.96-6.89 (m, 1H), 6.81-6.67 (m, 3H), 3.70-3.57 (m, 2H), 2.88-2.78 (m, 2H), 2.38 (s, 3H), 2.28 (s, 3H), 1.75 (s, 9H)。 1-085(#1):δ8.74 (s, 1H), 8.00 (s, 1H), 7.40-7.35 (m, 2H), 7.21-7.09 (m, 4H), 6.93-6.88 (m, 1H), 6.78-6.68 (m, 3H), 3.70-3.62 (m, 2H), 2.87-2.80 (m, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。1-087(#1):δ 7.25-7.07 (m, 6H), 6.94-6.89 (m, 1H), 6.82-6.70 (m, 3H), 3.70-3.62 (m, 2H), 2.87-2.80 (m, 2H), 2.37 (s, 3H), 2.30 (s, 3H), 2.23 (s, 3H), 1.74 (s, 9H)。 1-088(#1):δ8.47-8.44 (m, 1H), 7.43-7.37 (m, 2H), 7.34-7.31 (m, 1H), 7.23-7.09 (m, 4H), 6.93-6.88 (m, 1H), 6.78-6.69 (m, 3H), 3.71-3.62 (m, 2H), 2.89-2.81 (m, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。 1-090(#1):δ7.74-7.68 (m, 2H), 7.30-7.24 (m, 2H), 7.19-7.07 (m, 2H), 6.92-6.87 (m, 1H), 6.78-6.69 (m, 3H), 3.73-3.64 (m, 2H), 2.93-2.86 (m, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。 1-091(#1):δ7.96 (s, 1H), 7.45-7.40 (m, 2H), 7.32-7.27 (m, 2H), 7.23-7.11 (m, 2H), 6.95-6.88 (m, 1H), 6.82-6.68 (m, 3H), 4.70-4.60 (m, 1H), 3.71-3.62 (m, 2H), 2.91-2.83 (m, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.51 (d, J = 6.5 Hz, 6H)。 1-092(#1):δ7.39-7.34 (m, 2H), 7.19-7.05 (m, 5H), 6.92-6.87 (m, 1H), 6.75-6.67 (m, 3H), 3.69-3.61 (m, 2H), 2.86-2.78 (m, 2H), 2.28 (s, 3H), 2.17-2.06 (m, 1H), 1.73 (s, 9H), 1.18-1.02 (m, 4H)。<h2 style=";text-align:left;direction:ltr">1-093(#1):δ7.22-7.15 (m, 5H), 7.12 (s, 1H), 6.94-6.89 (m, 2H), 6.81-6.69 (m, 3H), 3.70-3.62 (m, 2H), 3.47 (s, 3H), 2.87-2.80 (m, 2H), 2.44 (s, 3H), 2.30 (s, 3H), 1.73 (s, 9H)。 1-094(#1):δ7.78-7.66 (m, 2H), 7.44-7.00 (m, 8H), 6.51-6.35 (m, 1H), 3.72-3.60 (m, 2H), 2.82 (t, J = 7.0 Hz, 2H), 2.77 (s, 3H), 1.72 (s, 9H)。 1-095(#1): δ7.98-7.92 (m, 2H), 7.28-7.21 (m, 2H), 7.19-7.10 (m, 2H), 6.90-6.84 (m, 1H), 6.76-6.68 (m, 3H), 4.20-4.15 (m, 3H), 3.74-3.60 (m, 2H), 2.92-2.81 (m, 2H), 2.39 (s, 3H), 2.30 (s, 3H), 1.73 (s, 9H)。 1-096(#1):δ7.99-7.90 (m, 2H), 7.44-7.29 (m, 2H), 7.28-7.17 (m, 3H), 7.16-7.00 (m, 2H), 6.52-6.43 (m, 1H), 4.17 (s, 3H), 3.74-3.61 (m, 2H), 2.91-2.80 (m, 2H), 2.38 (s, 3H), 1.72 (s, 9H)。 1-098(#1):δ7.97-7.89 (m, 2H), 7.44-7.16 (m, 5H), 7.16-7.03 (m, 2H), 6.58-6.44 (m, 1H), 4.77-4.64 (m, 1H), 3.71-3.61 (m, 2H), 3.47 (s, 3H), 2.91-2.79 (m, 2H), 1.72 (s, 9H), 1.69-1.62 (m, 3H)。1-099(#1):δ7.79-7.65 (m, 2H), 7.48-6.94 (m, 8H), 6.54-6.33 (m, 1H), 3.72-3.57 (m, 2H), 3.09 (q, J = 7.6 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H), 1.44 (t, J = 7.6 Hz, 3H)。 1-100(#1):δ7.79-7.67 (m, 2H), 7.53-6.94 (m, 8H), 6.53-6.33 (m, 1H), 3.74-3.56 (m, 2H), 3.44-3.31 (m, 1H), 2.88-2.69 (m, 2H), 1.72 (s, 9H), 1.45 (d, J = 6.8 Hz, 6H)。 1-101(#1):δ7.77-7.65 (m, 2H), 7.51-6.94 (m, 8H), 6.52-6.35 (m, 1H), 3.72-3.55 (m, 2H), 2.90-2.71 (m, 2H), 2.45-2.29 (m, 1H), 1.72 (s, 9H), 1.22-1.05 (m, 4H)。 1-102(#1):δ7.77-7.65 (m, 2H), 7.47-6.99 (m, 8H), 6.55-6.36 (m, 1H), 4.79 (s, 2H), 4.27 (s, 3H), 3.74-3.60 (m, 2H), 2.82 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。 1-103(#1):δ7.80-7.63 (m, 2H), 7.33-7.02 (m, 5H), 6.95-6.56 (m, 4H), 3.70-3.58 (m, 2H), 3.09 (q, J = 7.7 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 2.27 (s, 3H), 1.73 (s, 9H), 1.44 (t, J = 7.7 Hz, 3H)。1-104(#1):δ7.78-7.66 (m, 2H), 7.33-7.05 (m, 5H), 6.94-6.58 (m, 4H), 3.70-3.59 (m, 2H), 3.44-3.31 (m, 1H), 2.82 (t, J = 6.8 Hz, 2H), 2.26 (s, 3H), 1.73 (s, 9H), 1.45 (d, J = 6.8 Hz, 6H)。 1-105(#1):δ7.75-7.64 (m, 2H), 7.22-7.06 (m, 5H), 6.92-6.83 (m, 1H), 6.80-6.55 (m, 3H), 3.70-3.57 (m, 2H), 2.81 (t, J = 6.8 Hz, 2H), 2.42-2.30 (m, 1H), 2.27 (s, 3H), 1.73 (s, 9H), 1.21-1.05 (m, 4H)。 1-106(#1):δ7.77-7.65 (m, 2H), 7.38 (s, 1H), 7.24-7.05 (m, 4H), 6.93-6.83 (m, 1H), 6.80-6.62 (m, 3H), 4.79 (s, 2H), 3.72-3.59 (m, 2H), 3.53 (s, 3H), 2.82 (t, J = 7.0 Hz, 2H), 2.27 (s, 3H), 1.73 (s, 9H)。 1-108(#1):δ8.72-8.69 (m, 1H), 7.83-7.78 (m, 2H), 7.57-7.53 (m, 1H), 7.25-7.20 (m, 2H), 7.17-7.10 (m, 2H), 6.90-6.85 (m, 1H), 6.78-6.68 (m, 3H), 3.70-3.64 (m, 2H), 2.89-2.82 (m, 2H), 2.26 (s, 3H), 1.73 (s, 9H)。 1-109(#1):δ7.69-7.60 (m, 2H), 7.25-7.08 (m, 4H), 6.95-6.60 (m, 5H), 6.49-6.43 (m, 1H), 4.21 (q, J = 7.3 Hz, 2H), 3.73-3.58 (m, 2H), 2.90-2.75 (m, 2H), 2.27 (s, 3H), 1.73 (s, 9H), 1.54 (t, J = 7.3 Hz, 3H)。1-110(#1):δ7.73-7.63 (m, 2H), 7.60-7.56 (m, 1H), 7.24-7.08 (m, 4H), 6.93-6.84 (m, 1H), 6.80-6.54 (m, 4H), 5.42 (s, 2H), 3.69-3.58 (m, 2H), 3.37 (s, 3H), 2.81 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。 1-111(#1):δ7.69-7.59 (m, 2H), 7.53-6.97 (m, 6H), 6.56-6.37 (m, 3H), 6.28-6.21 (m, 1H), 3.94 (s, 3H), 3.73-3.59 (m, 2H), 2.87-2.75 (m, 2H), 1.72 (s, 9H)。 1-112(#1):δ7.74-7.62 (m, 2H), 7.61-7.56 (m, 1H), 7.45-7.00 (m, 7H), 6.62-6.54 (m, 1H), 6.53-6.36 (m, 1H), 5.42 (s, 2H), 3.73-3.59 (m, 2H), 3.37 (s, 3H), 2.81 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。 1-113(#1):δ7.69-7.59 (m, 2H), 7.44-7.00 (m, 8H), 6.52-6.35 (m, 2H), 4.21 (q, J = 7.4 Hz, 2H), 3.72-3.58 (m, 2H), 2.80 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H), 1.53 (t, J = 7.4 Hz, 3H)。 1-114(#1):δ7.99-7.89 (m, 2H), 7.76-7.66 (m, 1H), 7.57-7.50 (m, 1H), 7.43-7.17 (m, 3H), 7.14 (s, 1H), 7.11-7.02 (m, 1H), 6.53-6.40 (m, 1H), 4.75 (s, 2H), 4.18-4.07 (m, 2H), 3.57 (s, 3H), 2.87 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H)。1-115(#2):δ7.62-7.60 (m, 2H), 7.45-7.41 (m, 1H), 7.37-7.35 (m, 1H), 7.31-7.29 (m, 2H), 7.21 (m, 2H), 7.15 (s, 1H), 7.11-7.08 (m, 1H), 6.54-6.51 (m, 1H), 3.71-3.66 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 1.71 (s, 9H)。 1-116(#2):δ7.89-7.87 (m, 2H), 7.47-7.32 (m, 2H), 7.27-7.21 (m, 3H), 7.14 (s, 1H), 7.08-7.04 (m, 1H), 6.48-6.45 (m, 1H), 3.70-3.65 (m, 2H), 2.88-2.84 (m, 2H) 2.79 (s, 3H), 1.72 (s, 9H)。 1-118(#2):δ7.81-7.78 (m, 2H), 7.40-7.29 (m, 2H), 7.25-7.23 (m, 2H), 7.19 (m, 1H), 7.13 (s, 1H), 7.07-7.04 (m, 1H), 6.50-6.47 (m, 1H), 3.71-3.61 (m, 2H), 2.87 (t, J = 6.8, 2H), 2.24-2.19 (m, 1H), 1.72 (s, 9H), 1.22-1.18 (m, 4H)。 1-119(#1):δ7.89-7.86 (m, 2H), 7.40-7.28 (m, 4H), 7.18 (m, 1H), 7.13 (s, 1H), 7.07-7.02 (m, 1H), 6.51(m, 1H), 4.70 (s, 2H), 3.72-3.65 (m, 2H), 3.50 (s, 3H), 2.90-2.86 (m, 2H), 1.71 (s, 9H)。1-120(#2):δ8.13-8.03 (m, 2H), 7.80-7.73 (m, 1H), 7.64-7.55 (m, 1H), 7.39-7.35 (m, 4H), 7.33-7.27 (m, 3H), 7.14 (s, 1H), 7.09-7.03 (m, 1H), 6.53-6.46 (m, 1H), 3.75-3.65 (m, 2H), 2.93-2.84 (m, 2H), 1.72 (s, 9H)。 1-121(#2):δ7.80-7.73 (m, 2H), 7.45-7.32 (m, 3H), 7.31-7.21 (m, 2H), 7.14 (s, 1H), 7.12-7.03 (m, 1H), 6.54-6.43 (m, 1H), 3.74-3.61 (m, 2H), 2.93-2.81 (m, 2H), 2.71 (s, 3H), 1.71 (s, 9H)。 1-123(#2):δ7.85-7.83 (m, 2H), 7.27-7.25 (m, 2H), 7.17-7.13 (m, 1H), 7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.71 (m, 3H), 3.73-3.61 (m, 2H), 2.96 (dd, J = 8.0, 14.4 Hz, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H) 1.45 (t, J = 6.8 Hz, 3H)。 1-124(#2):δ7.80-7.77 (m, 2H), 7.27-7.23 (m, 2H), 7.17-7.13 (m, 1H), 7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.67 (m, 3H), 3.70-3.65 (m, 2H), 2.88-2.84 (m, 2H), 2.29 (s, 3H), 2.26-2.19 (m, 1H), 1.72 (s, 9H), 1.22-1.18 (m, 4H)。1-126(#2):δ7.85-7.82 (m, 2H), 7.27-7.25 (m, 2H), 7.17-7.13 (m, 1H), 7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.67 (m, 3H), 3.70-3.65 (m, 2H), 2.94-2.86 (m, 4H), 2.29 (s, 3H), 1.92-1.86 (m, 2H), 1.72 (s, 9H), 1.07 (t, J = 7.2 Hz, 3H)。 1-128(#2):δ7.83-7.81 (m, 2H), 7.41-7.31 (m, 2H), 7.22-7.19 (m, 3H), 7.14 (s, 1H), 7.06-7.03 (m, 1H), 6.47(m, 1H),5.17-5.13 (m, 1H) 3.73-3.63 (m, 3H), 2.84 (t, J = 7.2 Hz, 2H), 2.12-2.08 (m, 2H),1.80-1.75 (m, 2H) 1.71 (s, 9H), 1.50-1.19 (m, 6H)。 1-129(#2):δ7.86-7.81 (m, 2H), 7.44-7.29 (m, 2H), 7.22-7.18 (m, 3H), 7.15 (s, 1H), 7.06-7.00 (m, 1H), 6.49-6.38 (m, 1H), 3.72-3.63 (m, 6H), 2.99-2.82 (t, J = 6.8 Hz, 2H), 1.79-1.69 (m, 15H)。 1-130(#2):δ7.95-7.92 (m, 2H), 7.41-7.37 (m, 1H), 7.33-7.30 (m, 1H), 7.29-7.25 (m, 2H), 7.19 (s, 1H), 7.15-7.13 (s, 1H), 7.08-7.05 (m, 1H), 6.50-6.48 (m, 1H), 3.83-3.76 (m, 2H), 3.68 (dd, J = 12.8, 6.8 Hz, 2H), 3.63-3.60 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.79-1.66 (m, 15H)。1-131(#2):δ7.70-7.62 (m, 2H), 7.49-7.09 (m, 7H), 7.08-7.01 (m, 1H), 6.54-6.37 (m, 2H), 4.60-4.49 (m, 1H), 3.71-3.60 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H), 1.54 (d, J = 7.0 Hz, 6H)。 1-132(#2):δ7.69-7.62 (m, 2H), 7.45-7.40 (m, 1H), 7.26-7.10 (m, 4H), 6.99-6.62 (m, 4H), 6.50-6.44 (m, 1H), 4.60-4.49 (m, 1H), 3.68-3.59 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.27 (s, 3H), 1.73 (s, 9H), 1.54 (d, J = 7.0 Hz, 6H)。 1-135(#2):δ7.98-7.68 (m, 2H), 7.50-7.29 (m, 2H), 7.26-7.22 (m, 2H), 7.20-7.12 (m, 2H), 7.11 (s, 1H), 7.06-6.87 (m, 1H), 6.51-6.39 (m, 1H), 3.73-3.46 (m, 2H), 3.13-3.02 (m, 3H), 3.00-2.80 (m, 2H), 1.67 (s, 9H)。 1-136(#1):δ7.95-7.92 (m, 2H), 7.29-7.25 (m, 2H), 7.14-7.11 (m, 2H), 6.80-6.97 (1H), 6.74 (s, 3H), 3.78-3.63 (m, 6H), 2.90-2.88 (m, 2H), 2.32-2.29 (m, 3H), 1.75-1.73 (m, 15H)。1-137(#2):δ8.09-7.90 (m, 2H), 7.37-7.20 (m, 2H), 7.18-7.14 (m, 1H), 7.10 (s, 1H), 7.00-6.84 (m, 1H), 6.74-6.72 (m, 3H), 3.80-3.74 (m, 2H), 3.72-3.60 (m, 4H), 2.88 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.70 (s, 15H)。 1-138(#2):δ7.47-7.37 (m, 2H), 7.34-7.17 (m, 2H), 7.15-7.11 (s, 1H), 6.97-6.88 (m, 1H), 6.74-6.60 (m, 3H), 3.67 (m, 3H), 2.90-2.81 (m, 2H), 2.35 (m, 3H), 1.75 (s, 12H)。 1-139(#2):δ7.95-7.82 (m, 2H), 7.33-7.27 (m, 2H), 7.22-7.05 (m, 2H), 6.94-6.87 (m, 1H), 6.82-6.72 (m, 3H), 4.78-4.67 (s, 2H), 3.78-3.61 (m, 2H), 3.58-3.47 (s, 3H), 2.98-2.81 (m, 2H), 2.33-2.24 (s, 3H), 1.89-1.68 (s,9H)。 1-140(#1):δ7.96-7.82 (m, 2H), 7.44-7.28 (m, 3H), 7.22-7.19 (m, 2H), 7.15-7.06 (m, 2H), 6.51-6.44 (m, 1H), 5.16-5.12 (m, 1H), 3.73-3.63 (m, 2H), 3.50 (m, 2H), 2.91-2.82 (m, 2H), 1.83-1.58 (m, 9H), 1.52-1.24 (m, 4H), 1.01-0.95 (m, 3H)。1-143(#2):δ7.95-7.93 (m, 1H), 7.45-7.43 (m, 1H), 7.32-7.28 (m, 2H), 7.25-7.22 (m, 1H), 7.20-7.11 (m, 2H), 7.02-6.90 (m, 1H), 6.76-6.70 (m, 3H), 3.73-3.65 (m, 2H), 3.13 (d, J = 4.8 Hz, 3H), 2.94-2.85 (m, 2H), 2.37-2.29 (m, 3H), 1.79-1.68 (m, 9H)。 1-144(#2):δ7.95-7.93 (m, 1H), 7.43-7.41 (m, 1H), 7.30-7.27 (m, 2H), 7.25-7.21 (m, 1H), 7.19-7.12 (m, 2H), 7.01-6.89 (m, 1H), 6.75-6.73 (m, 3H), 3.71-3.62 (m, 2H), 3.60-3.55 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.36-2.28 (m, 3H), 1.74 (m, 9H), 1.36-1.22 (m, 3H)。 1-146(#2):δ7.85-7.81 (m, 1H), 7.41-7.33 (m, 1H), 7.30-7.07 (m, 4H), 6.99-6.87 (m, 1H), 6.73-6.65 (m, 3H), 5.16-5.15 (m, 1H), 3.69-3.62 (m, 2H), 3.55-3.36 (m, 2H), 2.88-2.81 (m, 2H), 2.45-2.16 (m, 3H), 1.71 (s, 9H), 1.35-1.15 (m, 3H)。 1-147(#2):δ7.94-7.90 (m, 1H), 7.42-7.40 (m, 1H), 7.29-7.12 (m, 3H), 7.10 (s, 1H), 7.00-6.87 (m, 2H), 6.76-6.72 (m, 3H), 4.37-4.27 (m, 1H), 3.71-3.63 (m, 2H), 2.91-2.84 (m, 2H), 2.35-2.25 (m, 3H), 1.76-1.66 (m, 9H), 1.35-1.30 (m, 3H), 1.28-1.19 (m, 3H)。1-149(#1):δ7.74-7.66 (m, 2H), 7.24-7.08 (m, 4H), 6.92-6.84 (m, 1H), 6.78-6.66 (m, 3H), 3.73-3.60 (m, 2H), 2.85 (t, J = 6.8 Hz, 2H), 2.48-2.37 (m, 1H), 2.28 (s, 3H), 1.72 (s, 9H), 1.32-1.13 (m, 4H)。 1-150(#2):δ7.94-7.91 (m, 2H), 7.35-7.26 (m, 2H), 7.23-7.10 (m, 2H), 7.07-7.03 (m, 1H), 6.94-6.87 (m, 2H), 6.81-6.72 (m, 3H), 3.76-3.63 (dd, J = 12.8, 6.8 Hz, 2H), 2.90-2.83 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.75 (s, 9H)。 1-151(#2):δ7.86-7.81 (m, 2H), 7.20-7.12 (m, 4H), 6.98-6.89 (m, 1H), 6.76-6.69 (m, 3H), 5.23 (br, 1H), 4.08-3.97 (m, 1H), 3.70-3.64 (m, 2H), 2.92-2.79 (m, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.36-1.32 (m, 6H)。 1-152(#2):δ7.84-7.79 (m, 2H), 7.38-7.19 (m, 3H), 7.17-7.02 (m, 2H), 6.96-6.84 (m, 1H), 6.74-6.67 (m, 3H), 3.65 (dd, J = 12.8, 6.8 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.59-2.36 (m, 3H), 2.30 (s, 3H), 1.71 (s, 9H)。1-153(#1):δ7.94-7.81 (m, 2H), 7.32-7.26 (m, 2H), 7.22-7.11 (m, 2H), 6.99-6.87 (m, 2H), 6.74-6.72 (m, 3H), 4.16-3.99 (m, 1H), 3.71-3.62 (m, 2H), 2.90-2.82 (t, J = 6.6 Hz, 2H), 2.35-2.30 (m, 3H), 2.09 (m, 1H), 1.73 (m, 12H), 1.51-1.22 (m, 6H)。 1-154(#1):δ7.94-7.91 (m, 1H), 7.43-7.40 (m, 1H), 7.29-7.19 (m, 4H), 7.11 (s, 1H), 6.97-6.88 (m, 1H), 6.74-6.71 (m, 3H), 3.71-3.63 (m, 2H), 2.87 (t, J = 6.6 Hz, 2H), 2.35-2.30 (m, 3H), 1.73 (s, 9H), 1.63-1.53 (m, 9H)。 1-155(#1):δ7.84-7.81 (m, 2H), 7.23-7.11 (m, 4H), 6.91-6.88 (m, 1H), 6.74-6.66 (m, 3H), 5.07-5.05 (m, 1H), 3.76-3.62 (m, 3H), 2.86 (t, J = 6.9 Hz, 2H), 2.33 (s, 3H), 2.13-2.09 (m, 1H), 1.73 (m, 12H), 1.51-1.22 (m, 6H)。 1-156(#1):δ7.85-7.82 (m, 2H), 7.22-7.12 (m, 4H), 6.91-6.88 (m, 1H), 6.75-6.66 (m, 3H), 5.14 (s, 1H), 3.65 (dd, J = 12.8, 7.0 Hz, 2H), 3.15 (s, 3H), 2.84 (t, J = 7.0 Hz, 2H), 2.31 (s, 3H), 1.76 (s, 9H)。1-157(#2):δ7.86-7.84 (m, 1H), 7.42-7.40 (m, 1H), 7.30-7.11 (m, 3H), 7.00-6.89 (m, 2H), 6.75-6.67 (m, 3H), 3.69-3.62 (m, 6H), 3.02 (m, 1H), 2.89-2.82 (m, 2H), 2.33 (m, 3H), 1.66 (s, 12H)。 1-158(#2):δ7.97-7.95 (m, 2H), 7.33-7.27 (m, 2H), 7.19-7.12 (m, 2H), 6.90-6.89 (m, 1H), 6.75-6.73 (m, 3H), 4.00-3.97 (m, 2H), 3.77-3.66 (m, 4H), 2.97-2.87 (m, 2H), 2.30 (s, 3H), 2.10-2.00 (m, 4H), 1.75 (s, 9H)。 1-159(#2):δ7.91-7.89 (m, 2H), 7.42-7.11 (m, 4H), 6.90-6.88 (m, 1H), 6.74-6.72 (m, 3H), 3.67 (dd, J = 12.8, 6.8 Hz, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.35-2.05 (m, 8H), 1.57 (s, 9H)。 1-161(#1):δ8.06-7.90 (m, 1H), 7.83-7.77 (m, 2H), 7.22-7.04 (m, 4H), 6.92-6.84 (m, 1H), 6.79-6.70 (m, 3H), 3.68-3.61 (m, 2H), 3.48-3.36 (m, 4H), 2.88-2.72 (m, 2H), 2.28 (s, 3H), 1.70 (s, 9H), 1.33-1.18 (m, 6H)。1-162(#1):δ7.97-7.93 (m, 2H), 7.29-7.27 (m, 2H), 7.20-7.12 (m, 2H), 6.95-6.89 (m, 1H), 6.75-6.73 (m, 3H), 3.72-3.56 (m, 4H), 3.27-3.18 (m, 3H), 2.90 (t, J = 6.6 Hz, 2H), 2.34 (s, 3H), 1.74 (s, 9H), 1.36-1.25 (m, 3H)。 1-163(#1):δ7.93-7.81 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.87 (m, 1H), 6.79-6.61 (m, 3H), 3.91-3.76 (m, 4H), 3.73-3.55 (m, 6H), 2.83 (t, J = 7.0 Hz, 2H), 2.35 (s, 3H), 1.77 (s, 9H)。 1-164(#1):δ7.86-7.79 (m, 2H), 7.43-7.08 (m, 5H), 6.93-6.87 (m, 1H), 6.79-6.71 (m, 3H), 3.89 (s, 3H), 3.76-3.57 (m, 2H), 2.87 (t, J = 6.9 Hz, 2H), 2.27 (s, 3H), 1.77 (s, 9H)。 1-165(#1):δ7.92-7.90 (m, 2H), 7.28-7.25 (m, 2H), 7.21-7.06 (m, 2H), 6.93-6.86 (m, 1H), 6.73-6.70 (m, 3H), 3.91-3.76 (m, 8H), 3.66 (dd, J = 12.8, 6.9 Hz, 2H), 2.85 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.70 (s, 9H)。 1-166(#2):δ7.84-7.81 (m, 2H), 7.21-7.07 (m, 4H), 6.93-6.87 (m, 1H), 6.73-6.64 (m, 3H), 3.67-3.54 (m, 4H), 3.16 (s, 3H), 2.87-2.79 (t, J = 6.8 Hz, 2H), 2.23 (s, 3H), 1.77 (s, 9H), 1.31-1.23 (m, 3H)。<h2 style=";text-align:left;direction:ltr">1-167(#1):δ7.62-7.60 (m, 2H), 7.20-6.99 (m, 4H), 6.91-6.68 (m, 5H), 3.61-3.46 (m, 2H), 3.07 (s, 3H), 2.63-2.63 (m, 2H), 2.31-2.18 (m, 3H), 1.73-1.65 (m, 9H)。 1-169(#2):δ7.87-7.85 (m, 1H), 7.44-7.12 (m, 6H), 6.96-6.90 (m, 1H), 6.80-6.64 (m, 2H), 3.91 (s, 3H), 3.77-3.64 (m, 2H), 3.39 (s, 3H), 2.97-2.80 (m, 2H), 2.32 (s, 3H), 1.79 (s, 9H)。 1-170(#2): δ8.04-7.81 (m, 2H), 7.22-7.10 (m, 5H), 6.90-6.88 (m, 1H), 6.74-6.72 (m, 3H), 3.68-3.63 (m, 2H), 3.06 (s, 6H), 2.85 (t, J = 6.7 Hz, 2H), 2.31 (s, 3H), 1.75 (s, 9H)。 1-171(#1):δ7.98-7.88 (m, 2H), 7.31-7.23 (m, 2H), 7.21-7.08 (m, 2H), 6.95-6.84 (m, 1H), 6.81-6.67 (m, 3H), 3.75-3.61 (m, 2H), 3.31 (s, 3H), 3.20 (s, 3H), 2.94-2.82 (m, 2H), 2.30 (s, 3H), 1.74 (s, 9H)。 1-173(#2):δ7.94-7.91 (m, 2H), 7.30-7.24 (m, 4H), 7.13 (s, 1H), 7.12-7.05 (m, 1H), 6.95-6.92 (m, 2H), 6.68-6.65 (m, 1H), 4.16 (q, J = 7.6 Hz, 1H), 3.70-3.64 (m, 2H), 2.86 (t, J = 7.2 Hz, 2H), 2.23 (s, 3H), 1.79 (d, J = 7.6 Hz, 3H), 1.74 (s, 9H)。1-180(#2):δ7.94-7.91 (m, 2H), 7.41-7.20 (m, 5H), 7.15 (s, 1H), 7.09-7.05 (m, 1H), 6.50-6.6.45 (m, 1H), 3.90 (s, 2H), 3.72-3.65 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H)。 1-185(#2):δ7.94-7.91 (m, 2H), 7.32-7.23 (m, 4H), 7.13 (s, 1H), 7.12-7.05 (m, 1H), 6.95-6.92 (m, 2H), 6.69-6.65 (m, 1H), 4.25 (q, J = 7.2 Hz, 1H), 3.70-3.64 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 2.72-2.66 (m, 2H), 1.79 (d, J = 7.2 Hz, 3H), 1.73 (s, 9H), 1.28 (t, J = 7.6 Hz, 3H)。 1-187(#2):δ7.94-7.89 (m, 2H), 7.32-7.24 (m, 4H), 7.13 (s, 1H), 7.12-7.07 (m, 1H), 6.95-6.92 (m, 2H), 6.70-6.65 (m, 1H), 4.35-4.26 (m, 1H), 3.69-3.63 (m, 2H), 2.88-2.69 (m, 4H), 1.90 (t, J = 7.4 Hz, 3H), 1.73 (s, 9H), 1.43-1.35 (m, 3H)。 1-189(#2):δ7.93-7.89 (m, 2H), 7.32-7.25 (m, 4H), 7.13 (s, 1H), 7.12-7.08 (m, 1H), 6.95-6.92 (m, 2H), 6.72-6.66 (m, 1H), 4.67-4.62 (q, J = 7.2 Hz, 1H), 3.71-3.64 (m, 2H), 3.34-3.22 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 1.99 (d, J = 7.6 Hz, 3H), 1.74 (s, 9H), 1.49 (t, J = 7.6 Hz, 3H)。1-193(#2):δ7.94-7.90 (m, 2H), 7.32-7.24 (m, 4H), 7.13 (s, 1H), 7.14-7.95 (m, 1H), 6.95-6.6.91 (m, 2H), 6.70-6.66 (m, 1H), 4.38-4.26 (m, 2H), 3.71-3.64 (m, 2H), 3.03-2.84 (m, 4H),1.73 (s, 9H), 1.45 (t, J = 7.6 Hz, 3H)。 1-194(#2):δ7.94-7.91 (m, 2H), 7.43-7.34 (m, 2H), 7.28-7.06 (m, 5H), 6.51-6.47 (m, 1H), 4.40-4.27 (m, 2H), 3.74-3.68 (m, 2H), 3.03-2.87 (m, 4H), 1.74 (s, 9H), 1.47 (t, J = 7.6 Hz, 3H)。 1-197(#2):δ7.95-7.91 (m, 2H), 7.30-7.24 (m, 4H), 7.13 (s, 1H), 7.10-7.06 (m, 1H), 6.95-6.91 (m, 2H), 6.69-6.64 (m, 1H), 3.93 (t, J = 7.6 Hz, 1H), 3.71-3.64 (m, 2H), 2.86 (t, J = 7.2 Hz, 2H), 2.24-2.07 (m, 5H), 1.74 (s, 9H), 1.10 (t, J = 7.6 Hz, 3H)。 1-198(#2):δ7.97-7.93 (m, 2H), 7.42-7.33 (m, 2H), 7.29-7.22 (m, 3H), 7.17 (s, 1H), 7.11-7.07 (m, 1H), 6.50-6.46 (m, 1H), 3.96-3.91 (m, 1H), 3.73-3.67 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.25-2.06 (m, 5H), 1.75 (s, 9H), 1.14-1.08 (m, 3H)。1-199(#2):δ7.95-7.90 (m, 2H), 7.32-7.25 (m, 4H), 7.14 (s, 1H), 7.11-7.07 (m, 1H), 6.96-6.6.93 (m, 2H), 6.70-6.66 (m, 1H), 4.20-4.15 (m, 1H), 3.70-3.64 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.63 (s, 3H), 2.46-2.20 (m, 2H), 1.74 (s, 9H), 1.22-1.07 (m, 3H)。 1-200(#2):δ7.87-7.83 (m, 2H), 7.34-6.99 (m, 7H), 6.43-6.39 (m, 1H), 4.12-3.95 (m, 1H), 3.640-3.58 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.56-2.54 (m, 3H), 2.42-2.12 (m, 2H), 1.67 (s, 9H), 1.13-1.02 (m, 3H)。 1-206(#2):δ7.88-7.83 (m, 2H), 7.34-6.99 (m, 7H), 6.43-6.39 (m, 1H), 4.10-3.95 (m, 1H), 3.64-3.58 (m, 2H), 2.82-2.52 (m, 4H), 2.40-2.15 (m, 2H), 1.66 (s, 9H), 1.35-1.25 (m, 3H), 1.13-0.97 (m, 3H)。 1-207(#2):δ7.95-7.89 (m, 2H), 7.32-7.25 (m, 4H), 7.13 (s, 1H), 7.11-7.06 (m, 1H), 6.95-6.6.92 (m, 2H), 6.71-6.66 (m, 1H), 4.48-4.41 (m, 1H), 3.72-3.63 (m, 2H), 3.31-3.09 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.61-2.36 (m, 2H), 1.74 (s, 9H), 1.50-1.43 (m, 3H), 1.15-1.06 (m, 3H)。1-208(#2):δ7.86-7.83 (m, 2H), 7.33-6.98 (m, 7H), 6.44-6.39 (m, 1H), 4.40-4.35 (m, 1H), 3.65-3.55 (m, 2H), 3.23-3.01 (m, 2H), 2.81 (t, J = 6.8 Hz, 2H), 2.53-2.30 (m, 2H), 1.66 (s, 9H), 1.43-1.32 (m, 3H), 1.07-0.96 (m, 3H)。 1-209(#2):δ7.94-7.91 (m, 2H), 7.35-7.22 (m, 5H), 7.13 (s, 1H), 7.10-7.07 (m, 1H), 6.95-6.92 (m, 1H), 6.68-6.65 (m, 1H), 3.70-3.62 (m, 2H), 2.88-2.82 (m, 4H), 1.73 (s, 9H), 1.11 (s, 9H)。 1-210(#2):δ7.95-7.91 (m, 2H), 7.40-7.34 (m, 2H), 7.28-7.21 (m, 3H), 7.16 (s, 1H), 7.09-7.05 (m, 1H), 6.48-6.45 (m, 1H), 3.72-3.65 (m, 2H), 2.89-2.84 (m, 4H), 1.73 (s, 9H), 1.22 (s, 9H)。 1-211(#2):δ7.93-7.89 (m, 2H), 7.31-7.22 (m, 4H), 7.13 (s, 1H), 7.10-7.07 (m, 1H), 6.94-6.91 (m, 2H), 6.69-6.64 (m, 1H), 3.70-3.63 (m, 2H), 3.05-3.01 (m, 1H), 2.88-2.82 (t, J = 6.8 Hz, 2H), 2.14-2.12 (m, 2H), 1.91-1.85 (m, 2H), 1.78-1.67 (m, 11H), 1.61-1.26 (m, 4H)。1-212(#2):δ7.95-7.91 (m, 2H), 7.42-7.27 (m, 2H), 7.27-7.21 (m, 3H), 7.17 (s, 1H), 7.10-7.06 (m, 1H), 6.49-6.46 (m, 1H), 3.73-3.68 (m, 2H), 3.07-3.01 (m, 1H), 2.88 (t, J = 6.8 Hz, 2H), 2.16-2.13 (m, 2H), 1.91-1.87 (m, 2H), 1.79-1.26 (m, 15H)。 1-216(#2):δ7.91-7.87 (m, 2H), 7.40-7.33 (m, 2H), 7.28-7.19 (m, 3H), 7.14 (s, 1H), 7.09-7.05 (m, 1H), 6.51-6.47 (m, 1H), 6.20-6.16 (m, 1H), 5.52-5.45 (m, 1H), 3.72-3.65 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.11 (s, 3H), 1.73 (s, 9H), 1.67-1.61 (m, 3H)。 1-224(#2):δ7.82-7.74 (m, 2H), 7.25-7.18 (m, 2H), 7.14-7.11 (m, 2H), 7.07 (s, 1H), 7.02-6.6.97 (m, 1H), 6.87-6.84 (m, 2H), 6.57-6.53 (m, 1H), 3.60-3.54 (m, 2H), 3.14 (s, 6H), 2.75 (t, J = 7.2 Hz, 2H),1.65 (s, 9H)。 1-226(#2):δ7.88-7.85 (m, 2H), 7.33-7.20 (m, 4H), 7.14 (s, 1H), 7.11-7.07 (m, 1H), 6.95-6.6.92 (m, 1H), 6.66-6.63 (m, 1H), 6.57-6.53 (m, 1H), 3.92 (s, 3H), 3.69-3.63 (m, 2H), 3.41 (s, 3H), 2.84 (t, J = 7.2 Hz, 2H), 1.73 (s, 9H)。1-259(#1):δ7.92 (d, J = 8.2 Hz, 2H), 7.35-7.20 (m, 4H), 7.12 (s, 1H), 7.11-7.02 (m, 1H), 6.98-6.88 (m, 2H), 6.75-6.58 (m, 1H), 4.86-4.74 (m, 1H), 3.74-3.54 (m, 4H), 2.85 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H), 1.67 (d, J = 6.8 Hz, 3H), 1.27 (t, J = 7.0 Hz, 3H)。 1-260(#2):δ7.52-6.75 (m, 11H), 3.59 (s, 2H), 2.74 (s, 2H), 2.32-2.26 (m, 3H), 1.90-1.66 (m, 9H)。 1-261(#2):δ7.93 (d, J = 7.7 Hz, 2H), 7.33-7.10 (m, 4H), 6.94-6.85 (m, 1H), 6.80-6.67 (m, 3H), 4.80 (q, J = 6.6 Hz, 1H), 3.75-3.55 (m, 4H), 2.92-2.82 (m, 2H), 2.29 (s, 3H), 1.77-1.64 (m, 12H), 1.27 (t, J = 7.0 Hz, 3H)。 1-262(#2):δ7.94 (d, J = 8.4 Hz, 2H), 7.31-7.10 (m, 3H), 6.96-6.84 (m, 2H), 6.78-6.68 (m, 3H), 4.58 (t, J = 6.8 Hz, 1H), 3.72-3.51 (m, 4H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 2.08-1.97 (m, 2H), 1.73 (s, 9H), 1.26 (t, J = 7.0 Hz, 3H), 1.02 (t, J = 7.3 Hz, 3H)。<h2 style=";text-align:left;direction:ltr">1-264(#2):δ7.89-7.87(m, 2H), 7.26-7.08(m, 4H), 6.94-6.89(m, 1H), 6.75-6.69(m, 3H), 3.98(s, 3H), 3.75-3.66(m, 2H), 3.59(s, 3H), 2.88-2.83 (m, 2H), 2.33 (s, 3H), 1.56 (s, 9H)。 1-265(#2):δ8.02-7.79 (m, 2H), 7.38-7.09 (m, 7H), 6.95-6.89 (m, 1H), 6.78-6.70 (m, 2H), 3.70-3.64 (m, 2H), 3.05-3.00 (m, 2H), 2.90-2.83 (m, 3H), 2.33-2.20 (m, 3H), 1.75 (s, 9H)。 1-266(#2): δ7.94-7.87 (m, 2H), 7.31-7.10 (m, 6H), 7.00-6.73 (m, 4H), 3.71-3.63 (m, 2H), 2.91-2.82 (m, 2H), 2.35-2.18 (m, 3H), 1.71 (s, 9H)。 1-267(#1): δ7.96-7.84 (m, 2H), 7.36-7.21 (m, 2H), 7.21-7.05 (m, 2H), 6.97-6.83 (m, 1H), 6.82-6.61 (m, 3H), 4.70-4.54 (m, 1H), 3.74-3.62 (m, 2H), 3.13 (s, 3H), 2.88 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.98 (d, J = 7.2 Hz, 3H), 1.73 (s, 9H)。1-268(#1):δ7.95-7.86 (m, 2H), 7.31-7.22 (m, 2H), 7.21-7.10 (m, 2H), 6.93-6.85 (m, 1H), 6.79-6.66 (m, 3H), 4.64 (q, J = 7.4 Hz, 1H), 3.74-3.61 (m, 2H), 3.39-3.16 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.98 (d, J = 7.4 Hz, 3H), 1.73 (s, 9H), 1.48 (t, J = 7.5 Hz, 3H)。 1-271(#2):δ7.89-7.86 (m, 1H), 7.52-7.40 (m, 1H), 7.30-7.11 (m, 5H), 7.00-6.89 (m, 1H), 6.76-6.69 (m, 2H), 3.71-3.64 (m, 2H), 3.53 (s, 3H), 2.87 (t, J = 6.7 Hz, 2H), 2.71 (s, 3H), 2.32 (s, 3H), 1.57 (s, 9H)。 1-272(#2):δ7.91-7.77 (m, 2H), 7.53-7.07 (m, 6H), 6.93-6.70 (m, 4H), 3.69-3.62 (m, 2H), 2.90-2.81 (m, 2H), 2.25 (s, 3H), 1.77-1.67 (m, 9H)。 1-273(#1):δ7.97-7.86 (m, 2H), 7.30-7.09 (m, 4H), 6.93-6.84 (m, 1H), 6.80-6.66 (m, 3H), 4.14 (q, J = 7.2 Hz, 1H), 3.74-3.60 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 2.21 (s, 3H), 1.78 (d, J = 7.2 Hz, 3H), 1.73 (s, 9H)。1-274(#1):δ7.97-7.88 (m, 2H), 7.30-7.09 (m, 4H), 6.92-6.84 (m, 1H), 6.78-6.65 (m, 3H), 4.23 (q, J = 7.4 Hz, 1H), 3.72-3.61 (m, 2H), 2.86 (t, J = 7.0 Hz, 2H), 2.76-2.60 (m, 2H), 2.29 (s, 3H), 1.77 (d, J = 7.5 Hz, 3H), 1.73 (s, 9H), 1.27 (t, J = 7.4 Hz, 3H)。 1-275(#2):δ7.97-7.94 (m, 2H), 7.26-7.11 (m, 4H), 6.94-6.70 (m, 4H), 4.19 (s, 3H), 3.71-3.64 (m, 2H), 2.93-2.76 (m, 4H), 2.32 (s, 3H), 1.71 (s, 9H), 1.31-1.16 (m, 3H)。 1-276(#2):δ7.97-7.87 (m, 2H), 7.30-7.22 (m, 2H), 7.21-7.09 (m, 2H), 6.93-6.86 (m, 1H), 6.79-6.67 (m, 3H), 3.89 (s, 2H), 3.73-3.62 (m, 2H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 6H), 1.73 (s, 9H)。 1-277(#2):δ7.97-7.88 (m, 2H), 7.30-7.22 (m, 2H), 7.21-7.09 (m, 2H), 6.93-6.86 (m, 1H), 6.80-6.68 (m, 3H), 3.93 (s, 2H), 3.71-3.63 (m, 2H), 2.87 (t, J = 7.0 Hz, 2H), 2.73 (q, J = 7.3 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.33 (t, J = 7.3 Hz, 3H)。1-278(#1):δ7.97-7.87 (m, 2H), 7.31-7.10 (m, 4H), 6.95-6.85 (m, 1H), 6.82-6.65 (m, 3H), 4.45-4.27 (m, 2H), 3.79-3.60 (m, 2H), 2.96-2.81 (m, 5H), 2.31 (s, 3H), 1.74 (s, 9H)。 1-279(#1):δ7.96-7.87 (m, 2H), 7.31-7.08 (m, 4H), 6.94-6.85 (m, 1H), 6.80-6.65 (m, 3H), 4.41-4.22 (m, 2H), 3.73-3.59 (m, 2H), 3.06-2.80 (m, 4H), 2.30 (s, 3H), 1.73 (s, 9H), 1.44 (t, J = 7.5 Hz, 3H)。 1-280(#1):δ7.95-7.86 (m, 2H), 7.34-7.08 (m, 4H), 6.91-6.84 (m, 1H), 6.78-6.66 (m, 3H), 4.64 (s, 2H), 3.74-3.59 (m, 2H), 3.24 (s, 3H), 2.93-2.82 (m, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。 1-281(#1):δ7.93-7.85 (m, 2H), 7.30-7.21 (m, 2H), 7.21-7.08 (m, 2H), 6.93-6.84 (m, 1H), 6.82-6.68 (m, 3H), 4.61 (s, 2H), 3.76-3.60 (m, 2H), 3.34 (q, J = 7.5 Hz, 2H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H), 1.52 (t, J = 7.5 Hz, 3H)。 1-282(#2):δ7.94-7.92 (m, 1H), 7.84-7.82 (m, 1H), 7.33-7.08 (m, 5H), 6.98-6.86 (m, 1H), 6.80-6.67 (m, 3H), 3.95-3.88 (m, 3H), 3.64 (s, 2H), 2.89-2.78 (m, 2H), 2.26 (s, 3H), 1.71 (s, 9H)。<h2 style=";text-align:left;direction:ltr">1-283(#2):δ7.96-7.88 (m, 2H), 7.29-7.08 (m, 4H), 6.93-6.86 (m, 1H), 6.80-6.67 (m, 3H), 4.20-4.08 (m, 1H), 3.72-3.62 (m, 2H), 2.91-2.82 (m, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.36-1.20 (m, 3H)。 1-285(#2):δ7.95-7.85 (m, 2H), 7.31-7.23 (m, 2H), 7.21-7.08 (m, 2H), 6.94-6.87 (m, 1H), 6.79-6.68 (m, 3H), 4.13 (s, 2H), 3.75-3.62 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H)。 1-288(#1): δ7.95-7.86 (m, 2H), 7.31-7.08 (m, 3H), 6.94-6.84 (m, 2H), 6.80-6.65 (m, 3H), 3.74-3.60 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H), 1.49 (s, 9H)。 1-289(#1):δ7.95-7.85 (m, 2H), 7.36-7.17 (m, 4H), 7.15-7.01 (m, 2H), 6.99-6.86 (m, 2H), 6.73-6.59 (m, 1H), 3.73-3.59 (m, 2H), 2.84 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H), 1.50 (s, 9H)。 1-291(#1):δ7.97-7.86 (m, 2H), 7.30-7.22 (m, 2H), 7.19-7.07 (m, 2H), 6.94-6.83 (m, 1H), 6.80-6.65 (m, 3H), 3.77-3.60 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 1.73 (s, 9H), 1.44 (s, 9H)。1-292(#1):δ7.96-7.86 (m, 2H), 7.32-7.21 (m, 4H), 7.14-6.99 (m, 2H), 6.96-6.86 (m, 2H), 6.75-6.60 (m, 1H), 3.79-3.59 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.73 (s, 9H), 1.44 (s, 9H)。 1-293(#1):δ7.99-7.90 (m, 2H), 7.50-7.25 (m, 5H), 7.24-7.18 (m, 1H), 7.15 (s, 1H), 7.12-7.03 (m, 1H), 3.78-3.63 (m, 2H), 2.90 (t, J = 6.8 Hz, 2H), 2.68 (d, J = 7.2 Hz, 2H), 2.31-2.15 (m, 1H), 1.73 (s, 9H), 1.04 (d, J = 6.5 Hz, 6H)。 1-294(#1):δ7.96-7.86 (m, 2H), 7.33-7.22 (m, 2H), 7.21-7.06 (m, 2H), 6.94-6.83 (m, 1H), 6.82-6.65 (m, 3H), 3.75-3.63 (m, 2H), 2.89 (t, J = 6.6 Hz, 2H), 2.67 (d, J = 7.2 Hz, 2H), 2.35-2.14 (m, 4H), 1.73 (s, 9H), 1.03 (d, J = 6.5 Hz, 6H)。 1-295(#1):δ7.97-7.87 (m, 2H), 7.32-7.21 (m, 4H), 7.14-7.01 (m, 2H), 6.96-6.86 (m, 2H), 6.76-6.62 (m, 1H), 3.75-3.61 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 2.67 (d, J = 7.2 Hz, 2H), 2.30-2.15 (m, 1H), 1.72 (s, 9H), 1.03 (d, J = 6.8 Hz, 6H)。1-296(#1):δ7.93-7.82 (m, 2H), 7.50-7.00 (m, 7H), 6.93-6.76 (m, 1H), 5.83-5.67 (m, 1H), 3.78-3.66 (m, 2H), 3.05-2.85 (m, 4H), 1.57-1.41 (m, 9H)。 1-297(#1):δ7.95-7.82 (m, 2H), 7.37-6.84 (m, 9H), 5.85-5.67 (m, 1H), 3.79-3.63 (m, 2H), 2.98 (q, J = 7.6 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 1.55-1.43 (m, 9H)。 1-298(#1):δ8.49-8.39 (m, 1H), 7.96-7.79 (m, 3H), 7.72-7.61 (m, 1H), 7.51-7.12 (m, 8H), 6.96-6.77 (m, 1H), 3.76-3.63 (m, 2H), 2.97 (q, J = 7.6 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 1.46 (t, J = 7.7 Hz, 3H)。 1-301(#2):δ8.00-7.91 (m, 2H), 7.44-7.18 (m, 5H), 7.15 (s, 1H), 7.11-7.04 (m, 1H), 6.59-6.44 (m, 1H), 4.50 (t, J = 6.6 Hz, 1H), 3.73-3.63 (m, 2H), 3.46 (s, 3H), 2.87 (t, J = 6.8 Hz, 2H), 2.11-1.97 (m, 2H), 1.72 (s, 9H), 1.02 (t, J = 7.5 Hz, 3H)。1-302(#2):δ7.96-7.87 (m, 2H), 7.49-7.28 (m, 2H), 7.27-7.18 (m, 3H), 7.15 (s, 1H), 7.11-7.03 (m, 1H), 6.54-6.43 (m, 1H), 3.98-3.88 (m, 1H), 3.72-3.64 (m, 2H), 3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.09-3.00 (m, 1H), 2.86 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H), 1.31 (d, J = 6.2 Hz, 3H)。 1-303(#2):δ7.98-7.91 (m, 2H), 7.30-7.21 (m, 2H), 7.20-7.10 (m, 2H), 6.92-6.86 (m, 1H), 6.78-6.68 (m, 3H), 4.50 (t, J = 6.6 Hz, 1H), 3.71-3.63 (m, 2H), 3.46 (s, 3H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 2.10-1.97 (m, 2H), 1.73 (s, 9H), 1.02 (t, J = 7.5 Hz, 3H)。 1-304(#2):δ7.96-7.88 (m, 2H), 7.30-7.09 (m, 4H), 6.94-6.86 (m, 1H), 6.78-6.66 (m, 3H), 3.98-3.89 (m, 1H), 3.73-3.62 (m, 2H), 3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.08-3.00 (m, 1H), 2.86 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H), 1.31 (d, J = 6.2 Hz, 3H)。1-305(#2):δ7.99-7.90 (m, 2H), 7.35-7.22 (m, 4H), 7.13 (s, 1H), 7.12-7.03 (m, 1H), 6.97-6.89 (m, 2H), 6.73-6.63 (m, 1H), 4.50 (t, J = 6.6 Hz, 1H), 3.72-3.62 (m, 2H), 3.46 (s, 3H), 2.85 (t, J = 7.0 Hz, 2H), 2.11-1.98 (m, 2H), 1.73 (s, 9H), 1.02 (t, J = 7.5 Hz, 3H)。 1-306(#2):δ7.95-7.87 (m, 2H), 7.34-7.20 (m, 4H), 7.15-7.03 (m, 2H), 6.97-6.87 (m, 2H), 6.75-6.61 (m, 1H), 3.98-3.88 (m, 1H), 3.71-3.61 (m, 2H), 3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.08-2.99 (m, 1H), 2.85 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H), 1.32 (d, J = 6.2 Hz, 3H)。 1-307(#1):δ8.16 (s, 1H), 7.96-7.93 (m, 2H), 7.28-7.11 (m, 4H), 6.97-6.87 (m, 1H), 6.74-6.72 (m, 3H), 4.26 (s, 3H), 3.71-3.64 (m, 2H), 2.96-2.85 (m, 2H), 2.32 (s, 3H), 1.72 (s, 9H)。 1-308(#1):δ8.73 (s, 1H), 7.99-7.89 (m, 2H), 7.46-7.00 (m, 7H), 6.58-6.40 (m, 1H), 3.74-3.62 (m, 2H), 2.87 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H)。1-309(#1):δ8.73 (s, 1H), 7.99-7.89 (m, 2H), 7.32-7.21 (m, 2H), 7.20-7.06 (m, 2H), 6.94-6.83 (m, 1H), 6.81-6.63 (m, 3H), 3.74-3.62 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。 1-313(#2):δ8.00-7.89 (m, 2H), 7.41-7.06 (m, 4H), 6.94-6.82 (m, 1H), 6.80-6.73 (m, 3H), 6.29 (s, 1H), 5.52-5.45 (m, 1H), 3.74-3.62 (m, 2H), 2.93-2.83 (m, 2H), 2.31 (s, 3H), 2.20-2.02 (m, 3H), 1.85-1.74 (m, 9H), 1.33-1.11 (m, 3H)。 1-314(#1):δ7.93-7.80 (m, 2H), 7.49-7.03 (m, 7H), 6.88-6.69 (m, 1H), 4.22 (s, 3H), 3.79-3.65 (m, 2H), 2.98 (q, J = 7.6 Hz, 2H), 2.90 (t, J = 6.8 Hz, 2H), 1.46 (t, J = 7.7 Hz, 3H)。 1-320(#1):δ7.99-7.96 (m, 2H), 7.27-7.24 (m, 2H), 7.18-7.11 (m, 2H), 6.91-6.86 (m, 1H), 6.74-6.72 (m, 3H), 4.40 (s, 3H), 3.67 (dd, J = 12.8, 7.0 Hz, 2H), 2.86 (t, J = 7.0 Hz, 2H), 2.25 (s, 3H), 1.68 (d, J = 26.2 Hz, 9H)。 1-321(#1):δ7.99-7.96 (m, 2H), 7.30-7.24 (m, 4H), 7.13-7.00 (m, 2H), 6.94-6.91 (m, 2H), 6.65 (s, 1H), 4.40 (s, 3H), 3.70-3.63 (m, 2H), 2.85 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。<h2 style=";text-align:left;direction:ltr">1-322(#1):δ7.96-7.93 (m, 2H), 7.39-7.03 (m, 8H), 4.38 (s, 3H), 3.70-3.63 (m, 2H), 2.84 (t, J = 6.8 Hz, 2H), 1.66 (s, 9H)。 1-323(#1):δ7.99-7.97 (m, 2H), 7.33-6.98 (m, 5H), 6.95-6.83 (m, 1H), 6.79-6.72 (m, 2H), 4.74-4.67 (m, 2H), 3.71-3.64 (m, 2H), 2.93-2.80 (m, 2H), 2.27 (s, 3H), 1.79-1.54 (m, 12H)。 1-324(#1):δ8.04-7.96 (m, 2H), 7.49-6.91 (m, 8H), 6.75-6.65 (m, 1H), 4.74-4.67 (m, 2H), 3.72-3.63 (m, 2H), 2.91-2.82 (m, 2H), 1.69-1.77 (m, 12H)。 1-325(#1):δ8.12-7.96 (m, 2H), 7.52-7.05 (m, 7H), 6.48 (s, 1H), 4.74-4.66(m, 2H), 3.76-3.65 (m, 2H), 2.94-2.80 (m, 2H), 1.91-1.54 (m, 12H)。 1-330(#1): δ7.93-7.91 (m, 2H), 7.27-7.11 (m, 3H), 7.03-6.87 (m, 2H), 6.79-6.72 (m, 3H), 3.71-3.64 (m, 2H), 2.90-2.80 (m, 2H), 2.35-2.33 (m, 1H), 2.29 (s, 3H), 1.94-1.80 (m, 3H), 1.74 (s, 9H)。 1-331(#1): δ7.98-7.91 (m, 2H), 7.46-7.01 (m, 6H), 6.94-6.91 (m, 2H), 6.67-6.65 (m, 1H), 5.97-5.75 (m, 1H), 3.70-3.63 (m, 2H), 2.88-2.80 (m, 2H), 1.94-1.84 (m, 3H), 1.76 (s, 9H)。<h2 style=";text-align:left;direction:ltr">1-336(#1):δ7.95-7.82 (m, 2H), 7.42-7.00 (m, 6H), 6.97-6.85 (m, 2H), 6.83-6.66 (m, 1H), 4.10 (s, 3H), 3.78-3.59 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。 1-337(#1):δ7.92-7.81 (m, 2H), 7.33-6.66 (m, 8H), 4.10 (s, 3H), 3.76-3.60 (m, 2H), 2.89 (t, J = 6.6 Hz, 2H), 2.29 (s, 3H), 1.72 (s, 9H)。 1-338(#1):δ7.97-7.86 (m, 2H), 7.32-7.08 (m, 5H), 7.07-6.66 (m, 7H), 5.31 (s, 2H), 3.77-3.58 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 1.72 (s, 9H)。 1-339(#1):δ7.95-7.84 (m, 2H), 7.36-7.05 (m, 7H), 7.04-6.92 (m, 2H), 6.88-6.60 (m, 4H), 5.63 (q, J = 6.6 Hz, 1H), 3.75-3.56 (m, 2H), 2.86 (t, J = 6.6 Hz, 2H), 2.26 (s, 3H), 1.86 (d, J = 6.6 Hz, 3H), 1.72 (s, 9H)。 1-341(#1):δ8.00-7.97 (m, 2H), 7.33-7.12 (m, 5H), 6.95-6.86 (m, 1H), 6.79-6.72 (m, 2H), 3.71-3.64 (m, 2H), 2.93-2.84 (m, 2H), 2.28 (s, 3H), 2.20-1.99 (m, 2H), 1.76 (s, 9H), 1.58-1.51 (m, 3H), 1.04-0.91 (m, 2H).1-342(#1):δ7.98 (d, J = 8.2 Hz, 2H), 7.48-7.20 (m, 5H), 7.15-6.91 (m, 4H), 4.64-4.60 (m, 2H), 3.70-3.63 (m, 2H), 2.91-2.83 (m, 2H), 2.17-2.05 (m, 2H), 1.69 (s, 9H), 1.06-0.88 (m, 3H)。 1-343(#1):δ8.09-7.96 (m, 2H), 7.54-7.05 (m, 7H), 6.47-6.45 (m, 1H), 4.64-4.59 (m, 2H), 3.73-3.63 (m, 2H), 2.91-2.84 (m, 2H), 2.16-2.05 (m, 2H), 1.67 (s, 9H), 1.06-0.94 (m, 3H)。 1-344(#1):δ8.00-7.97 (m, 2H), 7.46-7.12 (m, 4H), 6.98-6.81 (m, 1H), 6.74-6.72 (m, 3H), 5.16-5.07 (m, 1H), 3.71-3.64 (m, 2H), 3.02-2.84 (m, 2H), 2.31 (s, 3H), 1.82-1.50 (m, 15H)。 1-345(#2):δ7.99-7.97 (m, 2H), 7.46-7.20 (m, 4H), 7.17-7.03 (m, 2H), 6.98-6.91 (m, 2H), 6.66 (s, 1H), 5.16-5.07 (m, 1H), 3.70-3.63 (m, 2H), 2.91-2.82 (m, 2H), 1.83-1.55 (m, 15H)。 1-346(#1):δ8.13-7.96 (m, 2H), 7.49-7.05 (m, 7H), 6.47 (s, 1H), 5.16-5.06 (m, 1H), 3.72-3.63 (m, 2H), 3.01-2.81 (m, 2H), 1.77-1.51 (m, 15H)。1-347(#2):δ7.81-7.72 (m, 2H), 7.25-7.18 (m, 4H), 7.13 (s, 1H), 7.07-7.00 (m, 1H), 6.87-6.84 (m, 2H), 6.56-6.52 (m, 1H), 3.62-3.53 (m, 6H), 2.75 (t, J = 6.8 Hz, 2H),1.67-1.60 (m, 15H)。 1-348(#1):δ7.89 (d, J = 7.8 Hz, 2H), 7.37-7.23 (m, 7H), 7.14 (s, 1H), 7.07-7.04 (m, 1H), 6.97-6.87 (m, 3H), 6.48-6.45 (m, 1H), 4.14-4.10 (m, 2H), 3.70-3.63 (m, 2H), 3.17 (t, J = 7.5 Hz, 2H), 2.92-2.78 (m, 2H), 2.46-2.30 (m, 2H), 1.72 (s, 9H)。 1-349(#1):δ7.89 (d, J = 17.7 Hz, 2H), 7.38-7.31 (m, 2H), 7.25-7.19 (m, 5H), 7.14 (s, 1H), 7.08-7.02 (m, 3H), 6.48-6.45 (m, 1H), 3.71-3.64 (m, 2H), 3.27-3.23 (m, 4H), 2.90-2.82 (m, 2H), 1.72 (s, 9H)。 2-001(#2):δ7.93 (s, 1H), 7.42-7.31 (m, 2H), 7.27-7.15 (m, 4H), 7.13-7.06 (m, 1H), 7.03-6.98 (m, 1H), 6.59-6.49 (m, 1H), 3.97 (s, 3H), 3.86 (s, 3H), 3.67-3.58 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。2-002(#2):δ8.05 (s, 1H), 7.58-7.52 (m, 2H), 7.41-7.27 (m, 2H), 7.23-7.02 (m, 4H), 6.62-6.51 (m, 1H), 3.98 (s, 3H), 3.88 (s, 3H), 3.66-3.56 (m, 2H), 2.85 (t, J = 6.6 Hz, 2H), 1.71 (s, 9H). 2-003(#1):δ7.56-7.45 (m, 2H), 7.31-7.22 (m, 3H), 7.20-7.07 (m, 3H), 6.95-6.83 (m, 1H), 3.89 (s, 3H), 3.71-3.60 (m, 2H), 2.91-2.85 (m, 2H), 2.46 (s, 3H), 2.26 (s, 3H), 1.74 (s, 9H). 2-004(#2):δ 7.56-7.37 (m, 2H), 7.34-7.22 (m, 3H), 7.21-7.08 (m, 3H), 6.96-6.85 (m, 1H), 3.86 (s, 3H), 3.70-3.54 (m, 2H), 3.01-2.83 (m, 2H), 2.29 (s, 3H), 2.21-2.08 (m, 1H), 1.70 (s, 9H), 1.18-0.98 (m, 4H). ------------------------------------------------ [Test Examples] 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" stands for relative humidity. For example, "humidity 100% RH" indicates that the relative humidity is 100%.

[0423] Preparation of Test Solution The compound of the present invention was dissolved in an emulsified white sample (a mixture of Sorpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry Co., Ltd.), N-methylpyrrolidone, and Solvesso (registered trademark) 200 (manufactured by ExxonMobil Corporation) [1:5:28 (weight ratio)]) to prepare emulsions with concentrations of 1 mass %, 5 mass %, or 20 mass %. These emulsions were used as test solutions in the following Test Examples 1 to 7.

[0424] Test Example 1: Wheat blight control effect test 90 cm ３ Wheat (variety: Haruyutaka) was planted in plastic pots of 1.0 mm diameter, and at the 1.3-leaf stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the plants. One day after spraying, the wheat plants were inoculated by spraying with a conidial suspension of Septoria nodorum, and then placed in an inoculation box at 20°C and 100% RH for 2 days. The plants were then placed in an air-conditioned greenhouse (temperature 20°C, humidity 80% RH) and maintained there for 8 days. The proportion of lesions formed relative to the inoculated leaves was measured, and the control value was calculated according to the following formula:

[0425] Control titer = [1 - (lesion area rate in treated plots / lesion area rate in untreated plots)] x 100 As a result, of the compounds tested, the following compounds showed a control titer of 70% or more.

[0426] Compounds: No. 1-001, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-012, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022, 1-023, 1-024, 1-025, 1-0 26, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1-044, 1-045, 1-046, 1-047, 1-048, 1 -049, 1-050, 1-051, 1-052, 1-053, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-071 , 1-073, 1-075, 1-076, 1-077, 1-078, 1-079, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086, 1-088, 1-089, 1-090, 1-092, 1-094, 1-095, 1-096, 1-097, 1-0 98, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-127, 1-129, 1-132, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-145, 1-146, 1-148, 1-149, 1-150, 1-154, 1-155, 1-156, 1-157, 1-15 8, 1-159, 1-160, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1- 185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205,1-206, 1-207, 1-208, 1-210, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-300, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311, 1-312, 1-313, 1-314, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0427] Test Example 2: Tomato powdery mildew control effect test 90 cm ３ Tomatoes (variety: Momotaro) were planted in plastic pots of 100 mm diameter, and at the two-leaf stage, 5 ml of a test solution diluted with water to a concentration of 500 ppm was sprayed onto the plants. After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated with a conidial suspension of tomato powdery mildew (Leveillula taurica) by spray inoculation. After leaving the plants for 14 days, the proportion of lesions formed on the inoculated leaves was measured, and the control titer was calculated using the same formula as in Test Example 1.

[0428] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0429] 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, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1 -044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-059, 1-060, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067 , 1-068, 1-071, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086, 1-088, 1-089, 1-090, 1-091, 1-094, 1-0 95, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-134, 1-135, 1-136, 1-13 7, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1- 159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-179, 1-180, 1-181,1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-209, 1-210, 1-211, 1 -212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-2 76, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-298, 1-301, 1-302, 1-303, 1-304, 1-307, 1-308, 1-30 9, 1-310, 1-313, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-348, 1-349.

[0430] Test Example 3: Cucumber gray mold control effect test 90 cm ３ Cucumbers (variety: Sagamihanjiro) were planted in plastic pots. At the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed on the plants and air-dried. The treated leaves were then cut off and placed in a plastic container. A conidial suspension of Botrytis cinerea and dissolved PDA medium were mixed at a 1:1 (volume ratio), and 30 μl of the mixture was dropwise inoculated onto the treated leaves. After inoculation, the plants were left at 20°C and humid (100% RH) for 3 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.

[0431] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0432] 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, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1 -043, 1-044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063 , 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-0 84, 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-12 5, 1-126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1- 146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166,1-167, 1-168, 1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311, 1-312, 1-313, 1-314, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0433] Test Example 4: Cucumber stem rot control effect test 90 cm ３Cucumbers (variety: Sagamihanjiro) were planted in plastic pots. At the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the plants and air-dried. The treated leaves were then placed in a plastic container. Agar pieces (5 mm in diameter) containing cucumber stem rot (Sclerotinia sclerotiorum) that had been previously cultured on PDA medium were inoculated onto the treated cucumber cotyledons. After inoculation, the plastic container was covered with vinyl, humidified (100% RH), and left at 20°C for 2 days. The proportion of lesions formed relative to the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0434] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0435] Compounds: No. 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-0 22, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1 -044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064 , 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-0 85, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-12 6, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1- 147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-167, 1-168,1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311, 1-312, 1-313, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0436] Test Example 5 Cucumber powdery mildew control effect test 90 cm ３Cucumbers (variety: Sagami Hanpaku) were planted in plastic pots of 100 mm diameter, and at the cotyledon stage, 5 ml of a test solution diluted with water to a concentration of 500 ppm was sprayed onto the plants. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying with a conidial suspension of cucumber powdery mildew (Erysiphe polygoni). After leaving the plants for 9 days, the proportion of formed lesions on the inoculated leaves was measured, and the control titer was calculated using the same formula as in Test Example 1.

[0437] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0438] Compounds: No. 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022, 1-0 23, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1-044, 1 -045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065 , 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086, 1-0 88, 1-089, 1-090, 1-091, 1-092, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-13 0, 1-131, 1-132, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-153, 1- 154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176,1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-261, 1-262, 1-264, 1-267, 1-268, 1-269, 1-270, 1-271, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-313, 1-315, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0439] Test Example 6 Cucumber anthracnose control effect test 90 cm ３Cucumbers (variety: Sagamihanjiro) were planted in plastic pots of 100 mm diameter, and at the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the cucumbers. One day after spraying, a conidial suspension of cucumber anthracnose fungus (Colletotrichum lagenarium) was sprayed onto the cucumbers, which were then placed in an inoculation box at 25°C and 100% RH for 2 days. The cucumbers were then placed in an air-conditioned greenhouse (temperature: 23°C, humidity: 60% RH) and maintained there for 7 days. The proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0440] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0441] Compounds: No. 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-0 22, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1 -044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064 , 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-0 85, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-12 6, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1- 147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169,1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-184, 1-186, 1-187, 1-188, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-204, 1-2 05, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-259, 1-261, 1-262, 1-264, 1-265, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-307, 1-308, 1-309, 1-3 10, 1-311, 1-312, 1-313, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-348, 1-349.

[0442] Test Example 7 Soybean rust control effect test 90 cm ３Soybeans (variety: Enrei) were planted in plastic pots of 100 mm diameter, and at the single-leaf stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the plants. One day after spraying, the soybeans were inoculated by spraying with a conidial suspension of soybean rust (Phakopsora pachyrhizi), and then placed in an inoculation box at 20°C and 100% RH for 2 days. The plants were then placed in an air-conditioned greenhouse (temperature: 20°C, humidity: 60% RH) and maintained there for 10 days. The proportion of lesions formed relative to the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0443] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0444] Compounds: Nos. 1-003, 1-012, 1-015, 1-016, 1-022, 1-023, 1-025, 1-026, 1-027, 1-028, 1-032, 1-036, 1-038, 1-040, 1-041, 1-042, 1-043, 1-044, 1-045, 1-046, 1-048, 1-049, 1-050, 1-051, 1-074, 1-080, 1-082, 1-083, 1-085, 1-087, 1-088, 1-114, 1-175, 1-176, 1-178, 1-180, 1-182, 1-183, 1-184, 1-186, 1-215, 1-268, 1-270, 1-272, 1-273, 1-284, 1-314, 1-340.

[0445] The pyrazole compounds according to the present invention are extremely useful compounds which exhibit excellent pest control activity, particularly fungicidal activity, and which have almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects.

Claims

1. Formula (1): [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula: G １ is a hydroxyl, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl or di(C １ ~C ６ G represents an alkyl)aminocarbonyl; １ In the above relationship, when m5 represents an integer of 2, 3, 4 or 5, each G １ may be the same or different from each other, R Ｘ is 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, R Ｘ -1 to R Ｘ -4 represents a structure represented by the following structural formula, X １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X １ In the above relationship, when u5 is an integer of 2, 3, 4 or 5, each X １ may be the same or different from each other, X １ In the above relationship, when u4 represents an integer of 2, 3 or 4, each X １ may be the same or different from each other, R Ｙ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, 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, R ４ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy; R ５ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl; Z １ represents E-1 to E-29 or E-30; Z ２ is a hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Halocycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents an alkylsulfonyl group; ２ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same or different from each other, E-1 to E-30 each represent a structure represented by the following structural formula: Z ａ is hydroxy, thiol, halogen atom, cyano, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, -C(=NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ , phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same or different from each other, Z ａ In the relationship, when v4 represents an integer of 2, 3 or 4, each Z ａ may be the same or different from each other, Z ｂ is C １ ~C ６ represents alkyl, R ａ is hydroxy, cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyloxy, C １ ~C ６ Alkylcarbonylamino, phenylcarbonylamino, -OR ｇ , -C(O)R ｇ , -NR ｈ SO ２ R ｊ or Q-1, Q-1 being a structure represented by the following structural formula: Q １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; １ In the relationship, when w5 is an integer of 2, 3, 4 or 5, each Q １ may be the same or different from each other, R ｂ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｃ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｄ is amino, hydroxyamino, C １ ~C ６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ R represents (alkyl)amino, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy; R ｆ is a hydrogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, C １ ~C ６ Alkylsulfonyl or C １ ~C ６ represents haloalkylsulfonyl; R ｇ represents Q-1; ｈ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ 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, p represents an integer of 0 or 1, v4 represents an integer of 0, 1, 2, 3 or 4, v2 represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, and w5 represents an integer of 0, 1, 2, 3, 4 or 5.

2. G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R Ｘ is C １ ~C ６ Alkyl, R Ｘ -1 or R Ｘ -2, R Ｙ represents a hydrogen atom; R １ represents a hydrogen atom; R ２ represents a hydrogen atom; R ３ represents a hydrogen atom; R ４ represents a hydrogen atom; R ５ represents a hydrogen atom; Z １ represents E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z ２ is C １ ~C ６ represents alkoxy; Z ａ is a hydroxyl, thiol, halogen atom, C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, -C(=NOR ｂ ) R ｃ , -C(O)R ｄ , -NR ｅ R ｆ , phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; Q １ represents a halogen atom; ｂ is C １ ~C ６ represents alkyl, R ｃ is C １ ~C ６ represents alkyl, R ｅ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents alkoxy; R ｈ is C １ ~C ６ m5 represents an integer of 0 or 1; n4 represents an integer of 0 or 1; u5 represents an integer of 0; u4 represents an integer of 0; p represents an integer of 1; v4 represents an integer of 0; and w5 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to claim 1 .

3. Z １ The pyrazole compound or a salt thereof according to claim 2, wherein E-3, E-4, E-5, E-6, E-8, E-9, E-12, E-13, or E-29 is represented.

4. Z ａ is C １ ~C ６ Alkyl, R ａ C substituted with １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, -C(=NOR ｂ ) R ｃ , -NR ｅ R ｆ , phenyl, pyrrolidin-1-yl, morpholin-1-yl or piperidin-1-yl; R ａ is C １ ~C ６ Alkoxy or C １ ~C ６ The pyrazole compound or salt thereof according to claim 3, which represents alkylthio.

5. Z １ The pyrazole compound or a salt thereof according to claim 3 or 4, wherein E-3, E-4, E-5 or E-29 is represented.

6. An agricultural chemical comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 5.

7. A fungicide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 5.

8. An agricultural and horticultural fungicide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 5.

9. An antifungal agent comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 5.

10. An internal parasite control agent comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 5.

Images