Pyrazole compound and harmful organism control agent

Abstract

The present invention provides a new germicide, particularly a new agricultural or horticultural germicide. The present invention provides: a pyrazole compound represented by formula (1) (the formula represents a structure in which G represents G-1 or the like, G1 represents a C1-C6 haloalkyl or the like, RX represents a C1-C6 alkyl or the like, RY represents a hydrogen atom or the like, W represents -O- or -C(Ra)(R2)-, 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, Ra represents a hydrogen atom or the like, Z represents Z-1 or the like, Z1 represents a C1-C6 alkyl or the like, m5 and n5 each represent an integer of 0, 1, 2, 3, 4, or 5, and p represents an integer of 0 or 1); or a salt thereof.

Description

Pyrazole compounds and pest control agents

[0001] The present invention relates to novel pyrazole compounds and salts thereof, and pesticides containing said 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 to 6 disclose that certain pyrazole compounds are useful as fungicides, but do not disclose anything about the pyrazole compounds of the present invention.

[0004] International Publication No. WO 2011 / 117264, International Publication No. WO 2016 / 017719, International Publication No. WO 2009 / 028280, International Publication No. WO 1996 / 038419, International Publication No. WO 2023 / 243678, International Publication No. WO 2024 / 162284

[0005] 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.

[0006] 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.

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

[0008] That is, the present invention relates to the following [1].

[0009] [1] Formula (1):

[0010] [In the formula, G represents G-1 to G-10 or G-11, and G-1 to G-11 each represent a structure represented by the following structural formula:

[0011] G１ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ 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, di(C １ ~C ６ represents —C(═NOR)R′, １ In the relationship, when m2 represents an integer of 2, each G １ may be the same as or different from each other, １ In the relationship, when m3 represents an integer of 2 or 3, each G １ may be the same as or different from each other, １ In the relationship, when m4 represents an integer of 2, 3 or 4, each G １ may be the same as or different from each other, １ In the relationship, when m5 represents an integer of 2, 3, 4 or 5, each G１ may be the same as or different from each other, １ In the relationship, when m7 represents an integer of 2, 3, 4, 5, 6 or 7, each G １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(=NOR)aminocarbonyl, phenyl, —C(=NOR)R′, E-1 to E-62 or E-63. １ ~C ６ R' represents alkyl; １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, R Ｘ -1 to R Ｘ -5 represents a structure represented by the following structural formula,

[0012] X １is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X 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, 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, R ｃ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ represents —C(═NOR)R′, Ｙ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R １ is a hydrogen atom or C １ ~C ６ alkyl, W is —O— or —C(R ａ ) (R ２ )-, R ２ is a hydrogen atom or C １ ~C ６ represents alkyl, R ３ is a hydrogen atom, a hydroxyl, a halogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached, ａ is a hydrogen atom, C １ ~C ６ Alkyl, R ａ -1 to R ａ -5 or R ａ represents −6, and R ａ -1 to R ａ -6 represents a structure represented by the following structural formula,

[0013] R ５ is a hydrogen atom or C １ ~C ６ represents alkyl, R ６ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents an integer of 2, two R ５ and two R ６ may be the same as or different from each other, R ７ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl or phenyl; R ８ is a hydrogen atom or C １ ~C ６ represents alkyl, R ９ is a hydrogen atom or C １ ~C ６ Z represents Z-1 to Z-62 or Z-63, and Z-1 to Z-63 each represent a structure represented by the following structural formula:

[0014] In addition, Z in Z-4 to Z-7 and Z-49 to Z-52 １ represents a substitution on an aromatic ring; Z １is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R １２ C substituted with １ ~C ６ Alkyl, -OR ｄ , -NHC(O)R ｅ , —C(O)NHR ｕ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ NH ２ , -C(=NOH)NH ２ , E-1 to E-62 or E-63; Z １ In the relationship, when n2 is an integer of 2, each Z １ may be the same as or different from each other, １ In the relationship, when n3 represents an integer of 2 or 3, each Z １may be the same as or different from each other, １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, １ In the relationship, when n5 represents an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, １ In the relationship, when n6 represents an integer of 2, 3, 4, 5 or 6, each Z １ may be the same as or different from each other, １ In the relationship, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-62 or E-63, ｄ is C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-62 or E-63, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkylaminocarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C１ ~C ６ alkyl)aminocarbonyl, —C(═NOR)R′, E-1 to E-62 or E-63, ｅ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R １１ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, benzyloxy, E-1 to E-62 or E-63, ｕ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ alkoxy, benzyl, E-1 to E-62 or E-63; R １１ is cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R １２ is cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R ｆ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, di(C １ ~C ６ alkyl)amino, E-1 to E-62 or E-63, R ｇ is a hydrogen atom or tri(C １ ~C ４E-1 to E-63 each represent a structure represented by the following structural formula:

[0015] Z ａ is cyano, halogen atom, thiol, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; 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, ａIn the relationship, when v3 represents an integer of 2 or 3, 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, ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same as or different from each other, ｂ is a hydrogen atom, C １ ~C ６ Alkyl, —SO ２ R ｓ or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(═NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', J-1 to J-4 or J-5, R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5, R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino or R ｔ C substituted with １ ~C ６ represents alkylamino, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｔ is C １ ~C ６ Alkoxy, C １ ~C ６ haloalkyl, J-1 to J-4, or J-5, wherein J-1 to J-5 each represent a structure represented by the following structural formula:

[0016] Z ｃ is C １ ~C ６ represents an alkyl or halogen atom; Z ｃ In the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z ｃ may be the same as or different from each other, m2 represents an integer of 0, 1 or 2, m3 represents an integer of 0, 1, 2 or 3, m4 represents an integer of 0, 1, 2, 3 or 4, m5 represents an integer of 0, 1, 2, 3, 4 or 5, m7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, u4 represents an integer of 0, 1, 2, 3 or 4, u5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2, or 3; n2 represents an integer of 0, 1, or 2; n1 represents an integer of 0 or 1; p represents an integer of 0, 1, or 2; r １ represents an integer of 1 or 2; ２represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, v2 represents an integer of 0, 1 or 2, v3 represents an integer of 0, 1, 2 or 3, v4 represents an integer of 0, 1, 2, 3 or 4, v5 represents an integer of 0, 1, 2, 3, 4 or 5, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0017] The compound of the present invention represented by formula (1) exhibits excellent control activity against many pathogenic bacteria.

[0018] Therefore, the present invention can provide a useful fungicide, particularly a fungicide for agricultural and horticultural use.

[0019] The present invention will be described in detail below.

[0020] The compound of the present invention may exist as geometric isomers of the E- and Z-forms depending on the types of substituents, and the present invention includes mixtures containing these E- and Z-forms in any ratio. Furthermore, in this specification, the E- and Z-forms, or mixtures containing the E- and Z-forms in any ratios are collectively referred to as compounds having a wavy bond as follows:

[0021] Therefore, R ａ When a compound contains a structure represented by R ａ -6-1 and a compound having the following structure represented by R ａ It represents a mixture containing either one of the two geometric isomers of a compound having the following structure represented by formula (6-2), or both of them in any proportion.

[0022] Furthermore, the compound of the present invention may exist in optically active forms due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the present invention encompasses all optically active forms and racemic forms.

[0023] Furthermore, the compounds of the present invention may have tautomers depending on the type of substituent, and the present invention encompasses all tautomers or mixtures of tautomers containing any ratio.

[0024] 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 present invention encompasses all rotational isomers or mixtures of diastereomers containing all rotational isomers in any ratio.

[0025] 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.

[0026] As used herein, the term "aryl" refers to a cyclic group composed of carbon atoms and having aromaticity, and represents a monocyclic or polycyclic aromatic hydrocarbon group having usually 6 to 14, and preferably 6 to 10, carbon atoms, and specific examples thereof include benzene and naphthalene.

[0027] 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.

[0028] In this specification, "C ａ ~C ｂ The term "alkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl, each of which is selected within the range of the number of carbon atoms specified.

[0029] In this specification, "C ａ ~C ｂThe term "haloalkyl" refers to a linear or branched saturated hydrocarbon group having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when the group is substituted with two or more halogen atoms, the halogen atoms may be the same or different from one another. Specific examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, and 2,2,2-trichloroethyl, and each group may be selected within the range of the number of carbon atoms specified.

[0030] In this specification, "C ａ ~C ｂ The term "alkylene" refers to a linear or branched, divalent saturated hydrocarbon group having a to b carbon atoms, and specific examples thereof include ethylene, propylene, and butylene, each of which is selected within the range of the number of carbon atoms specified.

[0031] In this specification, "C ａ ~C ｂ The term "alkenyl" refers to a linear or branched unsaturated hydrocarbon having a to b carbon atoms and having one or more double bonds in the molecule, and specific examples thereof 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, each of which is selected within the range of the specified number of carbon atoms.

[0032] In this specification, "C ａ ~C ｂThe term "alkynyl" refers to a linear or branched unsaturated hydrocarbon having a to b carbon atoms and one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl, each selected from within the range of the number of carbon atoms specified.

[0033] In this specification, "C ａ ~C ｂ The term "alkoxy" represents alkyl-O- as defined above having a to b carbon atoms, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, and the like, and each alkoxy group is selected within the range of the number of carbon atoms specified.

[0034] In this specification, "C ａ ~C ｂ The term "haloalkoxy" represents haloalkyl-O- as defined above, having a to b carbon atoms, and specific examples thereof include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropyloxy, and the like, each selected within the range of the specified number of carbon atoms.

[0035] In this specification, "C ａ ~C ｂ The expression "alkenyloxy" represents alkenyl-O- as defined above having a to b carbon atoms, and specific examples thereof include vinyloxy, 1-propenyloxy, 2-propenyloxy, 1-methylethenyloxy, 2-butenyloxy, 2-methyl-2-propenyloxy, 3-methyl-2-butenyloxy, and 1,1-dimethyl-2-propenyloxy, and each is selected within the range of the specified number of carbon atoms.

[0036] In this specification, "C ａ ~C ｂThe expression "alkylthio" represents alkyl-S- as defined above having a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio, and each is selected within the range of the specified number of carbon atoms.

[0037] In this specification, "C ａ ~C ｂ The term "haloalkylthio" represents haloalkyl-S- as defined above, having a to b carbon atoms, and specific examples thereof include trifluoromethylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthio, heptafluoro-n-propylthio, heptafluoro-i-propylthio, nonafluoro-n-butylthio, nonafluoro-i-butylthio, nonafluoro-s-butylthio, and 4,4,4-trifluoro-n-butylthio, and each of these is selected within the range of the specified number of carbon atoms.

[0038] In this specification, "C ａ ~C ｂ The notation "alkylsulfinyl" represents alkyl-S(O)- as defined above having a to b carbon atoms, and specific examples include methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, n-butylsulfinyl, i-butylsulfinyl, S-butylsulfinyl, tert-butylsulfinyl, etc., selected within the range of the number of carbon atoms specified for each group. Incidentally, -S(O)- can also be simply expressed as -SO-.

[0039] 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 Specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0040] In this specification, "C ａ ~C ｂ The term "cycloalkyl" refers to a cyclic hydrocarbon group having a to b carbon atoms, which can form a single ring or multiple ring structures having 3 to 10 members. Each ring may be optionally substituted with alkyl within the specified range of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each of which is selected within the specified range of carbon atoms.

[0041] In this specification, "C ａ ~C ｂ The term "alkylamino" refers to an amino in which one of the hydrogen atoms is substituted with alkyl having a to b carbon atoms, and specific examples thereof include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino, each selected within the range of the number of carbon atoms specified.

[0042] In this specification, "di(C ａ ~C ｂ The expression "(alkyl)amino" represents amino in which both hydrogen atoms are substituted with alkyl as defined above, which may be the same or different and have a to b carbon atoms, and specific examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., selected within the range of the number of carbon atoms specified for each.

[0043] In this specification, "C ａ ~C ｂ The expression "alkylcarbonyl" represents alkyl-C(O)- having the above-mentioned meaning of a to b carbon atoms, and specific examples thereof include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl, and each alkyl group is selected within the range of the specified number of carbon atoms.

[0044] In this specification, "C ａ ~C ｂ The term "alkoxycarbonyl" represents alkyl-O-C(O)- having a to b carbon atoms as defined above, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl, and each of these is selected within the range of the number of carbon atoms specified.

[0045] In this specification, "C ａ ~C ｂ The expression "alkylaminocarbonyl" represents carbamoyl substituted by alkyl having the above-mentioned meaning, in which one of the hydrogen atoms has a to b carbon atoms, and specific examples thereof include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, tert-butylcarbamoyl, etc., selected within the range of the number of carbon atoms specified for each group.

[0046] In this specification, "C ａ ~C ｂ The term "cycloalkylaminocarbonyl" represents a carbamoyl in which one of the hydrogen atoms is substituted by the above-mentioned cycloalkyl having a to b carbon atoms, and specific examples thereof include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl, each selected from within the range of the number of carbon atoms specified.

[0047] In this specification, "di(C ａ ~C ｂThe expression "(alkyl)aminocarbonyl" represents carbamoyl in which both hydrogen atoms are substituted with alkyl as defined above, each of which may be the same or different and has a to b carbon atoms. Specific examples include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl, and are selected within the range of the number of carbon atoms specified for each group.

[0048] As used herein, "tri(C ａ ~C ｂ The expression "silyl" or "silyl group" refers to a silyl group substituted by alkyl groups having a to b carbon atoms, each of which may be the same or different. Specific examples include trimethylsilyl, triethylsilyl, tri(n-propyl)silyl, ethyldimethylsilyl, n-propyldimethylsilyl, n-butyldimethylsilyl, i-butyldimethylsilyl, and tert-butyldimethylsilyl, and are selected within the range of the number of carbon atoms specified for each group.

[0049] In this specification, "R １１ C substituted with ａ ~C ｂ alkyl," "R １２ C substituted with ａ ~C ｂ alkyl," "R ｃ C substituted with ａ ~C ｂ alkyl," "R ｈ C substituted with ａ ~C ｂ alkyl," "R ｊ C substituted with ａ ~C ｂ alkyl" or "R ｔ C substituted with ａ ~C ｂ The notation "alkyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R １１ , R １２ , R ｃ , R ｈ , R ｊ or R ｔTherefore, it represents a partially or fully substituted alkyl having the above-mentioned meaning, which has a to b carbon atoms, and the number of carbon atoms is selected within the range specified for each. １１ , R １２ , R ｃ , R ｈ , R ｊ or R ｔ When two or more groups are present, the substituent R １１ , R １２ , R ｃ , R ｈ , R ｊ or R ｔ may be the same or different from each other.

[0050] In this specification, "R ｊ C substituted with ａ ~C ｂ The notation "alkenyl" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ｊ represents an alkenyl having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, and the number of carbon atoms is selected within the range of each specified number of carbon atoms. ｊ When two or more groups are present, the substituent R ｊ may be the same or different from each other.

[0051] In this specification, "R ｂ C substituted with ａ ~C ｂ alkoxy" or "R ｈ C substituted with ａ ~C ｂ The notation "alkoxy" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ｂ and represents an alkoxy having the above-mentioned meaning, which is partially or completely substituted with a to b carbon atoms, and the number of carbon atoms is selected within the range of each specified number of carbon atoms. ｂ When two or more groups are present, the substituent R ｂ may be the same or different from each other.

[0052] In this specification, "R ｈ C substituted with ａ ~C ｂThe notation "haloalkoxy" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ｈ and the number of carbon atoms is selected within the range of the number of carbon atoms specified for each group. ｈ When two or more groups are present, the substituent R ｈ may be the same or different from each other.

[0053] In this specification, "R ｔ C substituted with ａ ~C ｂ The notation "alkylamino" means that any hydrogen atom attached to a carbon atom is substituted with one or more substituents R ｔ and represents alkylamino as defined above, having a to b carbon atoms, which are partially or completely substituted with the following, and the number of carbon atoms is selected within the range specified for each. ｔ When two or more groups are present, the substituent R ｔ may be the same or different from each other.

[0054] In this specification, "C ａ ~C ｂ The expression "alkylcarbonyloxy" represents alkyl-C(O)-O- having a to b carbon atoms as defined above, and specific examples thereof include acetyloxy, propionyloxy, and pivaloyloxy, and each is selected within the range of the number of carbon atoms specified.

[0055] In this specification, "C ａ ~C ｂ The term "alkoxycarbonyloxy" represents alkyl-O-C(O)-O- having a to b carbon atoms as defined above, and specific examples thereof include methoxycarbonyloxy, ethoxycarbonyloxy, and i-butoxycarbonyloxy, and each of these is selected within the range of the number of carbon atoms specified.

[0056] The term "halosulfonyloxy" used herein means a halogen atom -SO ２Specific examples of "halosulfonyloxy" include fluorosulfonyloxy and chlorosulfonyloxy.

[0057] 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.

[0058] 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.

[0059] The expression "arylsulfonyloxy" in this specification means aryl-SO ２ Specific examples of "arylsulfonyloxy" include phenylsulfonyloxy and paratoluenesulfonyloxy.

[0060] 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 ｂSpecific examples of "cycloalkylamino" include cyclopropylamino, cyclobutylamino, cyclopentylamino, and cyclohexylamino. ａ ~C ｂ The "cycloalkylamino" is selected from the range of carbon atoms specified.

[0061] The term "benzyl" used herein means -CH ２ C ６ H ５ Represents.

[0062] The term "benzyloxy" used herein means -O-CH ２ C ６ H ５ Represents.

[0063] r １ R when is 2 ａ -1 to R ａ R is -5 ａ -1' to R ａ -5', and r ２ R when is 0 ａ R is -6 ａ -6' represents a structure represented by the following structural formula:

[0064] 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) of the present invention," and "compound represented by formula (2)" will also be described as "compound (2)." Other compounds will also be described in a similar manner.

[0065] (Preparation Example 1) The compound (1) of the present invention can be prepared, for example, by the following preparation method.

[0066] [In the formula, J １ is a chlorine atom, a bromine atom, C １ ~C ４ Alkylcarbonyloxy or C１ ~C ４ represents alkoxycarbonyloxy; G and R Ｘ , R Ｙ , R １ , R ３ , R ４ , W, Z, and p have the same meanings as defined above.] Compound (1) of the present invention can be produced by reacting compound (2), compound (3) or a salt thereof (e.g., 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.

[0067] Alternatively, compound (1) of the present invention 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 either a base or an additive, or both.

[0068] The amount of compound (3) or a salt thereof used is 0.5 to 50 equivalents per equivalent of compound (2) or compound (2-1).

[0069] Some of the compounds (3) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds as described in the literature.

[0070] The amount of the dehydration condensation agent used is 0.5 to 50 equivalents per equivalent of compound (2).

[0071] 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.

[0072] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include water; alcohol solvents such as methanol, ethanol, and tert-butyl alcohol; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and diglyme; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and cyclohexane; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1,2-dichloroethane; nitrile solvents such as acetonitrile and propionitrile; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and N,N'-dimethylimidazolidinone; dimethyl sulfoxide; and pyridine; or mixed solvents thereof.

[0073] Examples of bases that can be used in the reaction include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, N,N-diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2) or compound (2-1).

[0074] Examples of additives that can be used in the reaction include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, 4-(dimethylamino)pyridine, etc. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2) or compound (2-1).

[0075] 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 and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0076] (Preparation Example 2) The compound (1-1) of the present invention can also be prepared, for example, by the following preparation method.

[0077] [wherein X represents a halogen atom, G and R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ａ , Z and p have the same meanings as above.] Compound (1-1) can be obtained by reacting compound (1-1-1) with compound (A) in a solvent or without a solvent, in the presence of a base, and optionally in the presence of either a copper catalyst or an additive, or both. Alternatively, compound (1-1) can be obtained by reacting compound (1-1-1) with compound (A) in the presence of a base, and optionally in the presence of a palladium catalyst and a ligand.

[0078] The amount of compound (A) used is 0.5 to 50 equivalents per equivalent of compound (1-1-1).

[0079] Some of the compounds (A) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds as described in the literature.

[0080] 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.

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

[0082] Examples of copper catalysts that can be used in the reaction include copper (monovalent) iodide, copper (monovalent) trifluoromethanesulfonate benzene complex, copper (monovalent) trifluoromethanesulfonate toluene complex, etc. The copper catalyst can be used in an amount of 0.001 to 50 equivalents relative to 1 equivalent of compound (1-1-1).

[0083] Examples of additives that can be used in the reaction include N,N-dimethylglycine, 4-(dimethylamino)pyridine, etc. The amount (equivalent) of the additive used can be 0.001 to 100 equivalents per equivalent of compound (1-1-1).

[0084] Examples of palladium catalysts that can be used in the reaction include palladium(divalent)(π-cinnamyl)chloride(dimer), allylpalladium(divalent)chloride(dimer), and tris(dibenzylideneacetone)dipalladium(zerovalent). The amount (equivalent) of the palladium catalyst used is 0.001 to 50 equivalents per equivalent of compound (1-1-1).

[0085] Examples of the ligand that can be used in the reaction include N-ethylpicolinamide, N-cyclohexylpicolinamide, N-cyclohexyl-4-(dimethylamino)picolinamide, N-cyclohexyl-4-methoxypicolinamide, N-cyclohexyl-1,4-dimethyl-1,2,3,4-tetrahydropyrido[3,4-b]pyrazine-7-carboxamide, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (tert-butyl-XPhos), tetramethyl-di-tert- Examples of suitable ligands include butylphosphino-2',4',6'-triisopropylbiphenyl (tetramethyldi-tert-butyl-XPhos), 2-di-(tert-butyl)phosphino-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (RockPhos), 2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (BrettPhos), and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos). The amount (equivalent) of the ligand used is 0.001 to 50 equivalents per equivalent of compound (1-1-1).

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

[0087] (Preparation Example 3) The compound (1-1-3) of the present invention can be prepared, for example, by the following preparation method.

[0088] [In the formula, G, J １ , R ａ , R ｅ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z １ , n4 and p have the same meanings as defined above.] The compound (1-1-3) of the present invention can also be produced by reacting the compound (1-1-2) of the present invention with the compound (D) or the compound (E) in a solvent or without a solvent, optionally in the presence of either a base or an additive, or both.

[0089] The amount of compound (D) or compound (E) used is 0.5 to 50 equivalents per equivalent of the compound (1-1-2) of the present invention.

[0090] Some of the compounds (D) and (E) are known compounds, and some are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0091] 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.

[0092] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of the compound of the present invention (1-1-2).

[0093] Examples of additives that can be used in the reaction include the additives exemplified in Production Example 1. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of the compound of the present invention (1-1-2).

[0094] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0095] The compound (1-1-2) of the present invention can be synthesized according to the method of Production Example 1.

[0096] (Preparation Example 4) The compound (1-1-4) of the present invention can be prepared, for example, by the following preparation method.

[0097] [In the formula, Z ａ１ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ５ alkenyl, Z-1 to Z-62 or Z-63; G, R ａ , R Ｘ , R Ｙ, R １ , R ２ , R ３ , R ４ and p have the same meaning as defined above.] The compound (1-1-4) of the present invention can be produced by reacting the compound (2-7) in a solvent or without a solvent, and optionally in the presence of a base.

[0098] 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.

[0099] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2-7).

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

[0101] (Preparation Example 5) The compound (1-1-5) of the present invention can be prepared, for example, by the following preparation method.

[0102] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ａ１ and p have the same meaning as defined above.] The compound (1-1-5) of the present invention can be produced by reacting the compound (2-8) with a dehydrating agent in a solvent or without a solvent.

[0103] Examples of the dehydrating agent that can be used include methyl N-(triethylammoniosulfonyl)carbamate, etc. The amount (equivalent) of the dehydrating agent used can be 0.1 to 100 equivalents per equivalent of compound (2-8).

[0104] 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.

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

[0106] (Preparation Example 6) The compound (1-7) of the present invention can be prepared, for example, by the following preparation method.

[0107] [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 R ｄ１ is C １ ~C ６ Alkyl or R ｄ represents G, R ｄ , R Ｘ , R Ｙ , R １ , R ３ , R ４ , Z １ , W, n4 and p have the same meanings as defined above.] The compound (1-7) of the present invention can be produced by reacting the compound (1-6) with the compound (C) in a solvent or without a solvent, optionally in the presence of either a base or an additive, or both.

[0108] The amount of compound (C) used is 0.5 to 50 equivalents per equivalent of compound (1-6).

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

[0110] 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.

[0111] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (1-6).

[0112] Examples of additives that can be used in the reaction include sodium iodide, potassium iodide, etc. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (1-6).

[0113] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0114] The compound (1-6) of the present invention can be synthesized according to the method of Production Example 1.

[0115] (Preparation Example 7) The compound (1-1-8) of the present invention can be prepared, for example, by the following preparation method.

[0116] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (1-1-8) can be produced by reacting compound (2-9) in a solvent or without a solvent, and optionally in the presence of a base.

[0117] 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.

[0118] 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).

[0119] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0120] (Preparation Example 8) The compound of the present invention (1-1-11) can be prepared, for example, by the following preparation method.

[0121] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-1-11) can be obtained by reacting compound (1-1-10) according to a known method known in the literature, for example, a method described in WO 2009 / 082398.

[0122] The compound of the present invention (1-1-10) can be synthesized according to the method of Production Example 1.

[0123] (Preparation Example 9) The compound (1-1-12) of the present invention can be prepared, for example, by the following preparation method.

[0124] [In the formula, G, J １ , R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (1-1-12) can be produced by reacting compound (1-1-11) with compound (D1) or compound (E1) in a solvent or without a solvent, and optionally in the presence of a base.

[0125] The amount of compound (D1) or compound (E1) used may be 0.5 to 50 equivalents per equivalent of compound (1-1-11).

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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 (1-1-11).

[0130] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0131] (Preparation Example 10) The compound of the present invention (1-1-13) can be prepared, for example, by the following preparation method.

[0132] [In the formula, A represents an oxygen atom or a sulfur atom, G and R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , n4 and p are as defined above.] Compound (1-1-13) can be produced by reacting compound (1-1-11) with 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole in a solvent or without a solvent, and optionally in the presence of a base.

[0133] The amount of 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole used may be 0.5 to 50 equivalents per equivalent of compound (1-1-11).

[0134] 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.

[0135] 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 (1-1-11).

[0136] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0137] (Preparation Example 11) The compound of the present invention (1-1-14) can be prepared, for example, by the following preparation method.

[0138] [In the formula, R ｒ１ is benzyl or C １ ~C ６ A, G, L, and R represent alkyl. ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-1-14) can be produced by reacting compound (1-1-13) of the present invention with compound (C1) in a solvent or without a solvent, and optionally in the presence of a base.

[0139] The amount of compound (C1) used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-1-13).

[0140] Some of the compounds represented by compound (C1) are known compounds and are commercially available. In addition, other compounds represented by compound (C1) can also be produced according to general synthetic methods for known compounds described in the literature.

[0141] 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.

[0142] 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 (1-1-13).

[0143] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0144] (Preparation Example 12) The compound of the present invention (1-1-16) can be prepared, for example, by the following preparation method.

[0145] [In the formula, G, R ａ , R ｒ１ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , n4 and p have the same meanings as defined above.] Compound (1-1-16) can be obtained by reacting compound (1-1-15) with an oxidizing agent in a solvent or without a solvent.

[0146] Examples of the oxidizing agent that can be used include metachloroperbenzoic acid, aqueous hydrogen peroxide, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents per equivalent of compound (1-1-15).

[0147] 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.

[0148] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0149] The compound of the present invention (1-1-15) can be synthesized according to the method of Production Example 11.

[0150] (Preparation Example 13) The compound of the present invention (1-1-17) can be prepared, for example, by the following preparation method.

[0151] [In the formula, Z ａ２ is C １ ~C ６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ alkyl)amino, -N(R ｐ ) C(O)Rｐ ', -N(R ｑ ) SO ２ R ｑ ', J-1 to J-4 or J-5; G, R ａ , R ｒ１ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ｐ , R ｐ ', R ｑ , R ｑ ', Z ２ , n4 and p are as defined above.] Compound (1-1-17) can be produced by reacting compound (1-1-16) of the present invention 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.

[0152] The amount of compound (K) used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-1-16).

[0153] 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.

[0154] 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.

[0155] 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 (1-1-16).

[0156] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0157] (Preparation Example 14) The compound (1-1-17) and the compound (1-1-19) of the present invention can be prepared, for example, by the following preparation method.

[0158] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , Z ａ２ , n4 and p are as defined above.] Compound (1-1-17) and compound (1-1-19) can be produced by reacting compound (1-1-18) of the present invention 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.

[0159] The amount of compound (K) used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-1-18).

[0160] 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.

[0161] 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.

[0162] 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 (1-1-18).

[0163] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0164] The compound of the present invention (1-1-18) can be synthesized according to the method of Production Example 9.

[0165] (Preparation Example 15) The compound of the present invention (1-1-21) can be prepared, for example, by the following preparation method.

[0166] [In the formula, Z ａ３ is C １ ~C ６ Alkylamino, C ３ ~C １０ Cycloalkylamino, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5; G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , n4 and p are as defined above.] Compound (1-1-21) can be produced by reacting compound (1-1-20) with compound (K1) in the presence of a halogenating agent, in a solvent or without a solvent.

[0167] The amount of compound (K1) used may be 0.5 to 50 equivalents per equivalent of compound (1-1-20).

[0168] 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.

[0169] 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.

[0170] Examples of halogenating agents that can be used in the reaction include N-chlorosuccinimide, and the amount of the halogenating agent used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-1-20).

[0171] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0172] The compound of the present invention (1-1-20) can be synthesized according to the method of Production Example 10.

[0173] (Preparation Example 16) The compound of the present invention (1-1-22) can be prepared, for example, by the following preparation method.

[0174] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , Z ａ３ , n4 and p are as defined above.] Compound (1-1-22) can be produced by reacting compound (1-1-21) with an oxidizing agent in a solvent or without a solvent, and optionally in the presence of a catalyst.

[0175] Examples of the oxidizing agent that can be used in the reaction include metachloroperbenzoic acid, aqueous hydrogen peroxide, etc. The amount of the oxidizing agent used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-1-21).

[0176] Examples of the catalyst that can be used in the reaction include ammonium molybdate(tetravalent) tetrahydrate, sodium tungstate dihydrate, phosphotungstic acid, etc. The amount of the catalyst used can be 0.001 to 50 equivalents relative to 1 equivalent of compound (1-1-21).

[0177] The reaction temperature and reaction time can be set arbitrarily within the temperature and time ranges described in Production Example 1. Production Example 17 The compound of the present invention (1-1-24) can be produced, for example, by the following production method.

[0178] [In the formula, R ｄ２ is a hydrogen atom or C １ ~C ６ represents alkyl, and R ｄ３ Ha-C(O)R ｐ ' or -SO ２ R ｑ ', G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４, R ｐ ', R ｑ ', Z ２ , Z ａ , n4 and p are as defined above.] Compound (1-1-24) can be produced by reacting compound (1-1-23) with compound (C3) or compound (C4) in a solvent or without a solvent, and optionally in the presence of a base.

[0179] The amount of compound (C3) or compound (C4) used may be 0.5 to 50 equivalents per equivalent of compound (1-1-23).

[0180] Some of the compounds represented by compound (C3) or compound (C4) are known compounds and are commercially available. In addition, other compounds represented by compound (C3) or compound (C4) can also be produced according to general synthetic methods for known compounds described in the literature.

[0181] 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.

[0182] 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 (1-1-23).

[0183] The reaction temperature and reaction time can be set arbitrarily within the temperature range and time range described in Production Example 1.

[0184] The compound of the present invention (1-1-23) can be synthesized according to the method of Production Example 13.

[0185] (Preparation Example 18) The compound (2-1-1) of the present invention can be prepared, for example, by the following preparation method.

[0186] [In the formula, G, L, R Ｘ , R Ｙ , R １ , R ３ , R ４and Z have the same meaning as defined above.] The compound (2-1-1) of the present invention can be produced by reacting the compound (2-11) with the compound (C5) in a solvent or without a solvent, optionally in the presence of either a base or an additive, or both.

[0187] The amount of compound (C5) used is 0.5 to 50 equivalents per equivalent of compound (2-11).

[0188] Some of the compounds (C5) 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.

[0189] 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.

[0190] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2-11).

[0191] Examples of additives that can be used in the reaction include sodium iodide, potassium iodide, etc. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2-11).

[0192] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0193] 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.

[0194] [Reaction Scheme 1]

[0195] [In the formula, R １００ is C １ ~C ６ represents alkyl, and G and R Ｘ and R Ｙhas the same meaning as above.] Compound (2) can be obtained by reacting compound (2-2) with a base in a solvent or without a solvent.

[0196] Some of the compounds (2-2) are known compounds described in Synlett, 2008, Vol. 11, p. 1673, and the other compounds can be synthesized in the same manner as known compounds according to the methods described in the literature.

[0197] Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2-2).

[0198] 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.

[0199] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0200] 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.

[0201] [Reaction Scheme 2]

[0202] [In the formula, G, J １ , 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. Alternatively, compound (2-1) can be obtained by reacting compound (2) with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, if necessary in the presence of a base, in accordance with the methods described in Tetrahedron Lett., 2003, vol. 44, p. 4819 and Journal of Medicinal Chemistry [J. Med. Chem.], 1991, vol. 34, p. 222, etc.

[0203] Among the compound (3) used in Production Example 1 or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), W is —C(R ａ ) (R ２ )- and R ａ is R ａ The compound (3') which is -1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 3.

[0204] [Reaction Scheme 3]

[0205] [In the formula, L, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , Z, p and r １ has the same meaning as above.] Step 1: Compound (3'-2) can be produced by reacting compound (3'-1) with compound (C6) or compound (C2) in a solvent or without a solvent, optionally in the presence of a base, and if necessary in the presence of a phase transfer catalyst.

[0206] Some of the compounds (3'-1) 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] Some of the compounds (C6) and (C2) are known compounds, and some are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0208] The amount of compound (C6) or compound (C2) used is 0.5 to 50 equivalents per equivalent of compound (3'-1).

[0209] 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.

[0210] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (3'-1).

[0211] The reaction can be carried out in the presence of a phase transfer catalyst. Examples of the phase transfer catalyst that can be used include quaternary ammonium salts such as tetrabutylammonium bromide. The amount (equivalent) of the phase transfer catalyst used can be 0.001 to 10 equivalents per equivalent of compound (3'-1).

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

[0213] Step 2: Compound (3') or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) can be produced by reacting compound (3'-2) with an acid in a solvent or without a solvent.

[0214] 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.

[0215] The reaction can be carried out in the presence of an acid. Examples of acids that can be used include hydrochloric acid, sulfuric acid, acetic acid, and trifluoroacetic acid. The amount of the acid used can be 0.5 to 1000 equivalents per equivalent of compound (3'-2).

[0216] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0217] The compound (1-1-1) used in Production Example 2 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 4.

[0218] [Reaction Scheme 4]

[0219] [In the formula, X, J １ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , R ａ , Z and p are as defined above.] Compound (1-1-1) can be produced by reacting compound (2-3), compound (3-6) or a salt thereof (e.g., 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.

[0220] Alternatively, compound (1-1-1) can also be produced by reacting compound (2-4) with compound (3-6) 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.

[0221] The amount of compound (3-6) or a salt thereof used is 0.5 to 50 equivalents per equivalent of compound (2-3) or compound (2-4).

[0222] Some of the compounds (2-3) 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.

[0223] Some of the compounds (3-6) 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.

[0224] The amount of the dehydration condensation agent used is 0.5 to 50 equivalents per equivalent of the compound (2-3).

[0225] Examples of the dehydration condensation agent include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and the like.

[0226] Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2-3).

[0227] 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.

[0228] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0229] Examples of additives that can be used in the reaction include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, 4-(dimethylamino)pyridine, etc. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2-3) or compound (2-4).

[0230] 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 and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0231] The compound (2-4) used in Reaction Scheme 4 can be produced, for example, according to the production route (reaction pathway) shown in Reaction Scheme 5 below.

[0232] [Reaction Scheme 5]

[0233] [In the formula, X, J １ , R Ｘ and R Ｙ has the same meaning as above.] Compound (2-4) can be obtained by reacting compound (2-3) 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. Alternatively, compound (2-4) can be obtained by reacting compound (2-3) with an organic acid halide such as pivaloyl chloride or isobutyl chloroformate, if necessary in the presence of a base, in accordance with the methods described in Tetrahedron Lett., 2003, vol. 44, p. 4819 and Journal of Medicinal Chemistry [J. Med. Chem.], 1991, vol. 34, p. 222, etc.

[0234] [Reaction Scheme 6]

[0235] [In the formula, R １０１ is C １ ~C ６ represents alkyl, and G and R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ and p have the same meaning as above.] Compound (2-6) can be obtained by hydrolyzing compound (2-5) in a solvent or without a solvent, and optionally in the presence of a base.

[0236] 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.

[0237] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2-5).

[0238] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0239] The compound (2-5) can be synthesized according to the method of Production Example 1.

[0240] 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.

[0241] [Reaction Scheme 7] Compound (2-7) can be produced, for example, by the following production method.

[0242] [In the formula, G, Z ａ１ , R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ and p have the same meaning as defined above.] Compound (2-7) can be obtained by reacting compound (2-6) with compound (G) according to a known method described in the literature, for example, the method described in WO 2008 / 156721.

[0243] 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.

[0244] 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.

[0245] [Reaction Scheme 8]

[0246] [In the formula, G, Z ａ１ , R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ and p have the same meaning as defined above.] Compound (2-8) can be obtained by reacting compound (2-6) with compound (H) according to a known method described in the literature, for example, the method described in WO 2008 / 016123.

[0247] 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.

[0248] The compound (2-9) used in Production Example 7 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 9.

[0249] [Reaction Scheme 9]

[0250] [In the formula, G, R ａ , R Ｘ , R Ｙ , R １ , R ２ , R ３ , R ４ , Z ２ , Z ａ１ , n4 and p have the same meanings as defined above.] Compound (2-9) can be obtained by reacting compound (2-10) with compound (M) according to a known method described in the literature, for example, the method described in WO 2008 / 156721.

[0251] Some of the compounds (M) 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.

[0252] The compound (2-10) can be synthesized according to the method of Production Example 1.

[0253] [Reaction Scheme 10]

[0254] Compound (2-11) can be produced by reacting compound (2), hydroxylamine or a salt thereof (e.g., 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.

[0255] Alternatively, the compound (2-11) of the present invention can also be produced by reacting the compound (2-1) with hydroxylamine or a salt thereof (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.) in a solvent or without a solvent, optionally in the presence of either a base or an additive, or both.

[0256] The amount of hydroxylamine or a salt thereof used is 0.5 to 50 equivalents per equivalent of compound (2) or compound (2-1).

[0257] Examples of the dehydrating condensing agent that can be used in the reaction include the dehydrating condensing agents exemplified in Production Example 1. The amount (equivalent) of the dehydrating condensing agent to be used is 0.1 to 100 equivalents per equivalent of compound (2).

[0258] 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.

[0259] Examples of the base that can be used in the reaction include the bases exemplified in Production Example 1. The amount (equivalent) of the base to be used is 0.1 to 100 equivalents per equivalent of compound (2) or compound (2-1).

[0260] Examples of additives that can be used in the reaction include the additives exemplified in Production Example 1. The amount (equivalent) of the additive used can be 0.005 to 100 equivalents per equivalent of compound (2) or compound (2-1).

[0261] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0262] Among the compound (3) used in Production Example 1 or a salt thereof (for example, hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, para-toluenesulfonate, etc.), W is —O— and R １ The compound (3-1) in which is a hydrogen atom and p is 1 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 11 or 17.

[0263] [Reaction Scheme 11]

[0264] [In the formula, R ｄ４ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl, R ｄ５ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl, R ３ , R ４ and Z have the same meaning as defined above.] Compound (3-1) can be produced by reacting compound (3-2) in a solvent in the presence of an acid such as 35% by mass hydrochloric acid or trifluoroacetic acid, in accordance with a known method described in the literature, for example, the method described in WO 2008 / 008398.

[0265] [Reaction Scheme 12]

[0266] [In the formula, L, R ３ , R ４ , R ｄ４ , R ｄ５and Z have the same meaning as defined above.] Compound (3-2) can be produced by reacting compound (3-3) with compound (C5) in a solvent in the presence of a base such as sodium hydroxide, sodium hydride, or diisopropylethylamine, in accordance with a known method described in the literature, for example, the method described in WO 2007 / 099385.

[0267] Some of the compounds (3-3) 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.

[0268] [Reaction Scheme 13]

[0269] [In the formula, R ３ , R ４ , R ｄ４ , R ｄ５ and Z have the same meaning as defined above.] Compound (3-2) can be produced by reacting compound (3-3) with compound (C7) in a solvent in the presence of a base such as triethylamine or diisopropylethylamine, a phosphorus compound such as triphenylphosphine or tri-n-butylphosphine, or an azo compound such as diethyl azodicarboxylate or diisopropyl azodicarboxylate, in accordance with a known method described in the literature, for example, the method described in WO 2013 / 110643.

[0270] Compound (C7) is a known compound, and some of them are commercially available. Others can also be prepared according to general synthetic methods for known compounds described in the literature.

[0271] [Reaction Scheme 14]

[0272] [In the formula, R ３ , R ４ , R ｄ４ , R ｄ５ , Z ａ１ , Z １and n4 have the same meaning as defined above.] Compound (3-4) can be obtained by reacting compound (3-5) with an acid such as hydrochloric acid, trifluoroacetic acid, or sulfuric acid in accordance with a known method described in the literature, for example, the method described in Journal of Organic Chemistry [J. Org. Chem.] 2007, Vol. 72, p. 658.

[0273] [Reaction Scheme 15]

[0274] [In the formula, J １ , R ３ , R ４ , R ｄ４ , R ｄ５ , Z １ , Z ａ１ and n4 have the same meaning as above.] Compound (3-5) can be produced by reacting compound (3-6) with compound (D1) or compound (E1) in a solvent or without a solvent, optionally in the presence of a base such as triethylamine or pyridine, according to a known method described in the literature, for example, the method described in WO 2012 / 116145. Alternatively, compound (3-6) can be produced by reacting compound (D2) with a dehydration condensation agent such as 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in a solvent or without a solvent, optionally in the presence of a base and / or an additive, according to the method described in WO 2012 / 162635.

[0275] Compound (D2) is a known compound, and some of them are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0276] [Reaction Scheme 16]

[0277] [In the formula, R ３ , R ４ , R ｄ４ , R ｄ５ , Z １and n4 have the same meaning as defined above.] Compound (3-6) can be produced by reacting compound (3-7) with hydroxylamine or a salt thereof in a solvent or without a solvent, and optionally in the presence of a base such as triethylamine, pyridine, or potassium carbonate, in accordance with a known method described in the literature, for example, the method described in WO 2013 / 000994.

[0278] The compound (3-7) can be synthesized according to the method of Reaction Scheme 12 or 13.

[0279] [Reaction Scheme 17]

[0280] [In the formula, R ３ , R ４ and Z have the same meaning as defined above.] Compound (3-1) can be produced by reacting compound (3-8) with hydrazine monohydrate, hydrazine monohydrochloride, or the like in a solvent, optionally in the presence of a base such as triethylamine or pyridine, in accordance with a known method described in the literature, for example, the method described in WO 2011 / 020861.

[0281] Some of the compounds (3-8) 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.

[0282] [Reaction Scheme 18]

[0283] [In the formula, R ３ , R ４ and Z have the same meaning as defined above.] Compound (3-8) can be produced by reacting compound (3-9) with compound (C7) in a solvent in the presence of a base such as triethylamine or diisopropylethylamine, a phosphorus compound such as triphenylphosphine or tri-n-butylphosphine, or an azo compound such as diethyl azodicarboxylate or diisopropyl azodicarboxylate, in accordance with a known method described in the literature, for example, the method described in WO 2013 / 110643.

[0284] The compound (3-9) is a known compound and is commercially available.

[0285] [Reaction Scheme 19]

[0286] [In the formula, L, R ３ , R ４ and Z have the same meaning as defined above.] Compound (3-8) can be produced by reacting compound (3-9) with compound (C5) in a solvent in the presence of a base such as sodium hydride, sodium hydroxide, or diisopropylethylamine, in accordance with a known method described in the literature, for example, the method described in WO 2011 / 020861.

[0287] The compound of the present invention can generally be used as an agricultural and horticultural bactericide or fungicide against various diseases caused by Phytophthora species, oomycetes, zygomycetes, ascomycetes, basidiomycetes, fungi imperfecti, bacteria or viruses.

[0288] "Pathogenic fungus" refers to a microorganism that causes a plant disease, and specific examples thereof include, but are not limited to, the following microorganisms:

[0289] Taphrina spp. (Taphrina deformans) T. Pneumocystis spp., Geotrichum spp., Candida spp. sorbosa, Pichia spp., Pichia kluyveri, Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp apii、C. asparagus、C. beticola、C. capsici、C. carotae、C. khaki、C. kikuchii、C. zonata, Cercosporidium spp., Cladosporium spp. cucumerinum、C. variabile agents) Davidiella spp., Didymosporium spp., Heterosporium spp. berkeley、M. cerasella、M. fijiensis、M. fragariae、M. graminicola、M. nawae、M. pinodes、M. pomi、M. zingiberis, Mycovellosiella spp. nattrassii, Paracercospora spp., Paracercospora egenula, Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp abelmoschi、P. fuligena、P. vitis, Pseudocercosporella spp., Ramichloridium spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp.(from Pyrenophora graminea, P. 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., Penicillium digitatum, P. spp. italicum、P. sclerotigenum activity) (Microsporum spp.) Trichophyton spp.(from Trichophyton mentagrophytes, T.S. 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. asparagus、F. of sp. potatoes、F. o. s. 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. (eg、Verticillium albo-atrum、V. dahliae、V. longisporum etc.), Ceratocystis spp. (eg Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp.(from 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 activity), Monilochaetes infuscans, Colletotrichum spp. capsici、C. cereal、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 spp. (e.g., Phialophora gregata, etc.), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis, etc.), Sarocladium Fungi of the Ascomycota phylum, such as Coleophoma spp., Helicoceras oryzae, etc. 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-fabe etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (eg Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. spp. (for example, Ustilago maydis, U. nuda etc.), Entyloma spp., Exobasidium spp. (eg, Exobasidium reticulatum, E. vexans etc.), Microstroma spp., Tilletia spp. (eg, Tilletia caries, T. controversial、T. laevis etc.), Itersonilia spp. (for example, Itersonilia perplexans etc.), Cryptococcus spp., Bovista spp.(e.g., Bovista dermoxantha, etc.), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum, etc.), Conocybe spp. (e.g., Conocybe apala, etc.), Marasmius spp. (e.g., Marasmius oreades, etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda, etc.), Sclerotium spp. (e.g., Sclerotium cepivorum, etc.), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis, etc.), Athelia spp. (e.g., Athelia rolfsii, etc.), Ceratobasidium spp. (e.g., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia Fungi of the phylum Basidiomycota such as Rhizoctonia solani, Thanatephorus spp. (e.g., Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp. Fungi of the phylum Chitridiomycota such as Olpidium spp. Fungi of the phylum Blastocladiomycota such as Physoderma spp. Fungi of the subphylum Mucoromycotina, such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), and Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer, etc.). Plasmodiophora spp.Protists of the phylum Cercozoa such as (for example, Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. Aphanomyces spp. (for example, Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (for example, Albugo macrospora, A. wasabiae, etc.), Bremia spp. (for example, Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (for example, Peronospora alliariae - wasabi, P. chrysanthemi - coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (for example, Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (for example, Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (for example, 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. (for example, 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. vexans, P. Oomycetes of the phylum Heterokontophyta, such as volutum, etc. Gram-positive fungi of the phylum Actinobacteria, such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis, etc.), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli, etc.), Streptomyces spp. (e.g., Streptomyces ipomoeae, etc.). Gram-positive bacteria of the 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. vesicatoria, X. citri subsp. citri, X. oryzae pv. pv. glycinea, P. syringae, P. s. pv. actinidiae, P. s. pv. eriobotryae, P. s. pv. helianthi, P. s. pv. lachrymans, P. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s. spinaciae, P. s. Gram-negative bacteria of the Proteobacteria phylum, such as P. pv. syringae, P. s. pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. (e.g., Brenneria nigrifluens, etc.), Dickeya spp. (e.g., Dickeya dianthicola, D. zeae, etc.), Erwinia spp. (e.g., Erwinia amylovora, E. rhapontici, etc.), Pantoea spp., and Pectobacterium spp. (e.g., Pectobacterium atrosepticum, P. carotovorum, P. wasabiae, etc.).

[0290] Specific examples of plant diseases caused by infection and proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases.

[0291] 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 of barley (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) is an example.

[0292] 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 these diseases 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 compound of the present invention has excellent control activity against many pathogens and is highly safe for target crops. Furthermore, the compound of the present invention can exert sufficient control effect even against pathogens that have acquired resistance to existing fungicides. Furthermore, the compound of the present invention does not cause phytotoxicity to target crops, has almost no adverse effects on mammals, fish, and beneficial insects, and has low residual properties and a low environmental impact.

[0293] 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 antifungals or endoparasite control agents, as antibacterial and antifungal agents for wood, paper and pulp, adhesives and paints, fibers, leather, etc., and as an industrial fungicide for cooling water channels in manufacturing plants, etc.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] The compounds of the present invention can be used as agricultural and horticultural fungicides as well as agents for controlling internal parasites in livestock, poultry, pets, and the like.

[0298] Specific examples of target internal parasites include, but are not limited to, the following:

[0299] Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus Nematodes such as the genera Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, and Parascaris; 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, Diphyllobothrix latum, Diphyllobothrix 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; Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima, Eimeria necatrix, Eimeria bovis, Eimeria obinoidaris ovinoidalis); Trypanosomsa cruzi, Leishmania, Plasmodium, Babesia, Trichomonadidae, Histomanas, Giardia, Toxoplasma, Entamoeba histolytica, Theileria, etc.

[0300] The compounds of the present invention can be used as agricultural and horticultural fungicides as well as antifungal agents.

[0301] Specific examples of pathogenic bacteria that can be targeted by antifungal agents include, but are not limited to, the following.

[0302] 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.

[0303] When the compound of the present invention is applied as a plant disease and plant pest control agent, it is usually mixed with an appropriate solid or liquid carrier, and if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, antidegradants, etc. may be added to form the compound into 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, gel, etc. From the viewpoint of labor saving and improved safety, the compound of the present invention can also be provided in any of the above formulations sealed in a water-soluble package.

[0304] 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; and the like.

[0305] 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; water; etc. These solid and liquid carriers may be used alone or in combination of two or more.

[0306] 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 type and betaine type.

[0307] The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the formulation of the present invention containing the surfactant. These surfactants may be used alone or in combination of two or more.

[0308] 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.

[0309] In particular, by applying it in combination with other pesticides or plant hormones, costs can be reduced by reducing the amount of applied chemicals, and the synergistic action of the mixed chemicals can be expected to broaden the fungicidal and insecticidal spectrum and to produce a more effective pest control effect. In this case, it is also possible to combine it with multiple known pesticides at the same time.

[0310] In one embodiment, types of pesticides to 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 to be mixed with the compound of the present invention are not necessarily limited to these.

[0311] 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.

[0312] 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.

[0313] 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.

[0314] Antifungals, such as ketoconazole and miconazole nitrate.

[0315] 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.

[0316] 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 of 0.005 to 50 kg per hectare (ha) is appropriate, and 0.01 to 1 kg is preferred.

[0317] Next, formulation examples for the preparation using the compound 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.

[0318] [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, an anti-decomposition agent and the like can be mentioned.

[0319] [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 ingredients, for example, a spreading agent, a decomposition inhibitor, etc. may be mentioned.

[0320] [Suspension Agent] Compound of the present invention 0.1-70 parts Liquid carrier 15-98.89 parts Surfactant 1-12 parts Others 0.01-30 parts As the other ingredients, for example, an antifreeze agent, a thickener, etc. may be mentioned.

[0321] [Water Dispersible Granules] 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, binders, antidecomposition agents and the like can be mentioned.

[0322] [Liquid Formulation] Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts Examples of other ingredients include antifreezing agents and spreading agents.

[0323] [Granules] Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts As the other ingredients, for example, a binder, a decomposition inhibitor and the like can be mentioned.

[0324] [Dust] Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts As the other ingredients, for example, anti-drift agents, anti-decomposition agents and the like can be mentioned.

[0325] 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.

[0326] Next, specific formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient are shown below, but the present invention is not limited to these examples. In the following formulation examples, "parts" means parts by weight.

[0327] 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 (mixture of 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.

[0328] 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.

[0329] Formulation Example 3: Dust Compound of the present invention No. 1-001 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.

[0330] 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 uniformly 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 applied so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

[0331] Formulation Example 5: Flowable Compound of the present invention No. 1-001 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. When used, the flowable 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.

[0332] Formulation Example 6: Dry flowable formulation 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, the mixture is granulated in an extrusion granulator, and the mixture is 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.

[0333] 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.

[0334] [Summary] Based on the above, the embodiments of the present invention relate to the following [1] to

[68] .

[0335] [1] Formula (1):

[0336] [In the formula, G represents G-1 to G-10 or G-11, and G-1 to G-11 each represent a structure represented by the following structural formula:

[0337] 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 ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ 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, di(C １ ~C ６ represents —C(═NOR)R′, １ In the relationship, when m2 represents an integer of 2, each G １ may be the same as or different from each other, １ In the relationship, when m3 represents an integer of 2 or 3, each G １ may be the same as or different from each other, １In the relationship, when m4 represents an integer of 2, 3 or 4, each G １ may be the same as or different from each other, 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, １ In the relationship, when m7 represents an integer of 2, 3, 4, 5, 6 or 7, each G １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(=NOR)aminocarbonyl, phenyl, —C(=NOR)R′, E-1 to E-62 or E-63. １ ~C ６ R' represents alkyl; １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘrepresents -5, R Ｘ -1 to R Ｘ -5 represents a structure represented by the following structural formula,

[0338] X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X 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, 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, R ｃ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ represents —C(═NOR)R′, Ｙ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R １ is a hydrogen atom or C １ ~C ６ alkyl, W is —O— or —C(R ａ ) (R ２ )-, R ２ is a hydrogen atom or C １ ~C ６ represents alkyl, R ３ is a hydrogen atom, a hydroxyl, a halogen atom or C １ ~C ６represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached, ａ is a hydrogen atom, C １ ~C ６ Alkyl, R ａ -1 to R ａ -5 or R ａ represents −6, and R ａ -1 to R ａ -6 represents a structure represented by the following structural formula,

[0339] R ５ is a hydrogen atom or C １ ~C ６ represents alkyl, R ６ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents an integer of 2, two R ５ and two R ６ may be the same as or different from each other, R ７ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl or phenyl; R ８ is a hydrogen atom or C １ ~C ６ represents alkyl, R ９ is a hydrogen atom or C １ ~C ６ Z represents Z-1 to Z-62 or Z-63, and Z-1 to Z-63 each represent a structure represented by the following structural formula:

[0340] In addition, Z in Z-4 to Z-7 and Z-49 to Z-52 １ represents a substitution on an aromatic ring; Z １ is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R １２ C substituted with １ ~C ６ Alkyl, -OR ｄ , -NHC(O)R ｅ , —C(O)NHR ｕ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ NH ２ , -C(=NOH)NH ２ , E-1 to E-62 or E-63; Z １ In the relationship, when n2 is an integer of 2, each Z １may be the same as or different from each other, １ In the relationship, when n3 represents an integer of 2 or 3, each Z １ may be the same as or different from each other, １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, １ In the relationship, when n5 represents an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, １ In the relationship, when n6 represents an integer of 2, 3, 4, 5 or 6, each Z １ may be the same as or different from each other, １ In the relationship, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-62 or E-63, ｄ is C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-62 or E-63, ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６Alkylcarbonyl, C １ ~C ６ Alkylaminocarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, —C(═NOR)R′, E-1 to E-62 or E-63, ｅ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R １１ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, benzyloxy, E-1 to E-62 or E-63, ｕ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ alkoxy, benzyl, E-1 to E-62 or E-63; R １１ is cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R １２ is cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R ｆ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, di(C １ ~C ６alkyl)amino, E-1 to E-62 or E-63, R ｇ is a hydrogen atom or tri(C １ ~C ４ E-1 to E-63 each represent a structure represented by the following structural formula:

[0341] Z ａ is cyano, halogen atom, thiol, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; 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 v3 represents an integer of 2 or 3, 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, ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same as or different from each other, ｂ is a hydrogen atom, C １ ~C ６ Alkyl, —SO ２ R ｓ or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(═NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', J-1 to J-4 or J-5, R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5, R ｎ is a hydrogen atom or C １~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino or R ｔ C substituted with １ ~C ６ represents alkylamino, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｔ is C １ ~C ６ Alkoxy, C １ ~C ６haloalkyl, J-1 to J-4, or J-5, wherein J-1 to J-5 each represent a structure represented by the following structural formula:

[0342] Z ｃ is C １ ~C ６ represents an alkyl or halogen atom; Z ｃ In the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z ｃ may be the same as or different from each other, m2 represents an integer of 0, 1 or 2, m3 represents an integer of 0, 1, 2 or 3, m4 represents an integer of 0, 1, 2, 3 or 4, m5 represents an integer of 0, 1, 2, 3, 4 or 5, m7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, u4 represents an integer of 0, 1, 2, 3 or 4, u5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2, or 3; n2 represents an integer of 0, 1, or 2; n1 represents an integer of 0 or 1; p represents an integer of 0, 1, or 2; r １ represents an integer of 1 or 2; ２represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, v2 represents an integer of 0, 1 or 2, v3 represents an integer of 0, 1, 2 or 3, v4 represents an integer of 0, 1, 2, 3 or 4, v5 represents an integer of 0, 1, 2, 3, 4 or 5, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0343] [2] G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; ２ is C １ ~C ６ represents alkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ represents alkoxy or E-1, Ｘ is C １ ~C ６ Alkyl, C ３ ~C１０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano or C １ ~C ６ represents haloalkyl, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, R ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, and R ５ represents a hydrogen atom, R ６ represents a hydrogen atom, R ７ is C １ ~C ６ represents alkyl, Z is Z-1, Z-3, Z-4, Z-6, Z-8, Z-9, Z-10, Z-11, Z-18, Z-23, Z-25, Z-26, Z -27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42, Z-49, Z-53, Z-58 or Z-60, Z １ is a carboxy, hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ, -C(=NOH)NH ２ , represents E-1 to E-3, E-5, E-18, E-20, E-21, E-22, E-23, E-28 to E-30, E-40, E-41, E-42, E-43 to E-45, E-48, E-58, E-62 or E-63, Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5, R ｄ represents E-2 or E-4, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; Z ａ is a halogen atom, hydroxy, thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(Rｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; Z ｂ is a hydrogen atom, C １ ~C ６ Alkyl, —SO ２ R ｓ or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ' or J-5, R ｋ is C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino, J-2 or J-5; R ｎ ' is C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or J-5, ｑ ' is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔ represents J-5, m2 represents an integer of 0 or 1, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0 or 2, u5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 0, 1, 2 or 3, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n1 represents an integer of 1, r １ represents an integer of 1, v2 represents an integer of 0 or 1, v3 represents an integer of 0 or 1, v4 represents an integer of 0, 1 or 2, v5 represents an integer of 0 or 1, w5 represents an integer of 0, w7 represents an integer of 0, w8 represents an integer of 0 or 1, and w10 represents an integer of 0. The pyrazole compound or a salt thereof according to the above [1].

[0344] [3] W is -C(R ａ ) (R ２ )-, G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; ２ is C １ ~C ６ represents alkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ represents alkoxy or E-1, Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano or C １ ~C ６ represents haloalkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, and R ５ represents a hydrogen atom; ６ represents a hydrogen atom; ７ is C １ ~C ６ represents alkyl, Z represents Z-1, Z-3, Z-4, Z-8, Z-9, Z-11, Z-25, Z-26, Z-33, Z-34, Z-41, Z-42, Z-53, Z-58 or Z-60; １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C１０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -C(=NOH)NH ２ , represents E-1 to E-3, E-18, E-20, E-21, E-22, E-23, E-28 to E-30, E-40 to E-45, E-48, E-58, E-62 or E-63, Z ２ represents E-2, and R ｄ represents E-2 or E-4, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; Z ａ represents a halogen atom, a thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with１ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-3 or J-5; Z ｂ is a hydrogen atom, C １ ~C ６ Alkyl, —SO ２ R ｓ or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ' or J-5, R ｋ is C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino, J-2 or J-5; R ｎ ' is C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６represents alkoxy or J-5, ｑ ' is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔ represents J-5, m2 represents an integer of 0 or 1, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0 or 2, u5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 1, 2 or 3, n4 represents an integer of 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 1, n1 represents an integer of 1, p represents an integer of 0 or 1, r １ represents an integer of 1, v2 represents an integer of 0 or 1, v4 represents an integer of 0, 1 or 2, v5 represents an integer of 1, w5 represents an integer of 0, w7 represents an integer of 0, and w8 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to [1] above.

[0345] [4] W represents —O—; １ is a halogen atom, C １ ~C ６Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 or R Ｘ represents −2, and R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ represents a hydrogen atom, Z is Z-1, Z-6, Z-8, Z-9, Z-10, Z-11, Z-18, Z-23, Z-26, Represents Z-27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42 or Z-49, Z １ is a carboxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ alkoxycarbonyl, E-2, E-3, E-5, E-18, E-20, E-21, E-23, E-28, E-29, E-30, E-40, E-41, E-42 or E-63; Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5, R ｈis C ３ ~C １０ Cycloalkyl, C １ ~C ６ alkoxy, E-2 or E-3; Z ａ is a halogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; Z ｂ is C １ ~C ６ Alkyl or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', and R ｋ is C １ ~C ６ represents alkyl, R ｋ ' represents a hydrogen atom, R ｍ Is Ji (C １ ~C ６ alkyl)amino or J-2, ｎ is C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｐ represents a hydrogen atom, R ｐ' represents J-5, and R ｑ is C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ represents alkyl, R ｒ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, n1 represents an integer of 1, u5 represents an integer of 0, u4 represents an integer of 0, v5 represents an integer of 0, v4 represents an integer of 0 or 1, v3 represents an integer of 0 or 1, v2 represents an integer of 0 or 1, v1 represents an integer of 1, w8 represents an integer of 0, and w10 represents an integer of 0. The pyrazole compound or a salt thereof according to the above [1].

[0346] [5] G represents G-1, G-2, G-3 or G-4, １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents haloalkoxy; R Ｘ is C １ ~C ６ Alkyl or C ３ ~C １０ represents cycloalkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ２ represents a hydrogen atom; ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached, ａ is a hydrogen atom or C １ ~C ６ Z represents Z-1, Z-8, Z-9, Z-10, Z-11, Z-25, Z-26, Z-33, Z-34 or Z-49; Z １ is a carboxy, hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ haloalkoxy, E-40, E-41 or E-63; Z ２ is a hydrogen atom, C １ ~C ６ represents alkyl or E-1; Z ａ is a halogen atom, hydroxy, thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ represents alkoxy, R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl; Z ｂ is a hydrogen atom or C １ ~C ６ m4 represents an integer of 1, m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, n2 represents an integer of 1, v5 represents an integer of 0, and v1 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to [1] or [2] above.

[0347] [6] G represents G-1, 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 ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ By forming an alkylene chain, R ３ and R ４ represents that R forms a three-membered ring together with the carbon atom to which it is attached; ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C６ alkoxy, E-40, E-41 or E-63; Z ａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ represents alkoxy, R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl; Z ｂ is C １ ~C ６ m5 represents an integer of 1; n5 represents an integer of 1 or 2; and v1 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to [5] above.

[0348] [7] G represents G-1, 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, R １ represents a hydrogen atom, R ２ represents a hydrogen atom, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a three-membered ring together with the carbon atom to which it is attached; ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ alkoxy, E-40 or E-41; Z ａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ represents alkoxy, R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ m5 represents an integer of 1; n5 represents an integer of 1 or 2; and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [6].

[0349] [8] G represents G-1, １is 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 is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, R ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ alkoxy, E-40 or E-41; Z ａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ represents alkoxy, R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６m5 represents an integer of 1; n5 represents an integer of 1 or 2; and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [6].

[0350] [9] G represents G-1, 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, 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 ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６

[0023]

[0024] The pyrazole compound or salt thereof according to any one of [1] to [6] above, wherein m5 represents an alkoxy group, p represents an integer of 1, m5 represents an integer of 1, and n5 represents an integer of 1 or 2.

[0351]

[10] R Ｘ is C ４ m5 represents an integer of 1; and n5 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of [1] to [9] above.

[0352]

[11] G represents G-1, １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｘis C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ is a hydrogen atom or C １ ~C ６ represents alkyl, R ａ is a hydrogen atom or C １ ~C ６ alkyl; Z represents Z-1 or Z-41; Z １ is hydroxy, cyano, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ alkoxycarbonyl, E-2 or E-41; R ｈ represents E-2, and Z ａ is a halogen atom or C １ ~C ６ m5 represents an integer of 0 or 1; n5 represents an integer of 1; n1 represents an integer of 1; v1 represents an integer of 1; and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0353]

[12] G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ２ represents a hydrogen atom, R ａ represents a hydrogen atom, Z represents Z-1, Z １ is C １ ~C ６ alkyl, E-2 or E-41; Z ａ is a halogen atom or C １ ~C ６m5 represents an integer of 1; n5 represents an integer of 1; v1 represents an integer of 1; and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to

[11] above.

[0354]

[13] G represents G-1, G-2, G-3, G-4, G-5, G-6, G-7 or G-8, １ is a cyano, a halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1, R Ｘ -2, R Ｘ -3 or R Ｘ represents −4, and R Ｙ represents a hydrogen atom; １ is a hydrogen atom or C １ ~C ６ represents alkyl, W represents —C(R ａ ) (R ２)-, R ２ represents a hydrogen atom, R ３ represents a hydrogen atom, a hydroxyl or a halogen atom; R ４ represents a hydrogen atom or a halogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z-3, Z-4 or Z-11, Z １ is a cyano, a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ haloalkoxy or R ｈ C substituted with １ ~C ６ represents alkoxy, R ｈ is cyano, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl or C ２ ~C ６ m2 represents an integer of 1, m3 represents an integer of 0, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0, u5 represents an integer of 0, n7 represents an integer of 1, n5 represents an integer of 1, 2 or 3, n3 represents an integer of 0 or 1, and p represents an integer of 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [3].

[0355]

[14] G represents G-1, １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, R ２ represents a hydrogen atom, R３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ m5 represents an integer of 1; and n5 represents an integer of 1 or 2. The pyrazole compound or a salt thereof according to

[13] above.

[0356]

[15] G represents G-1, １ represents a halogen atom; Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z １ is R ｈ C substituted with １ ~C ６ represents alkoxy, R ｈ represents E-1 or E-2, Z ａ is a halogen atom or C １ ~C ６ m5 represents an integer of 1; n5 represents an integer of 1; v4 represents an integer of 1; and v5 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0357]

[16] G represents G-1, １ is a halogen atom or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６represents alkyl, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom, R ３ and R ４ is R ３ and R ４ Together, C ２-４ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 5-membered ring together with the carbon atom to which it is attached; ａ represents a hydrogen atom, Z represents Z-1 or Z-8, Z １ is a cyano, a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ alkoxycarbonyl, E-40 or E-41; Z ａ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl or di(C １ ~C ６ R represents alkyl)amino; ｊ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 1 or 2, n4 represents an integer of 2, p represents an integer of 1, v1 represents an integer of 1, and v2 represents an integer of 0, 1, or 2. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0358]

[17] R ３ and R ４ is R ３ and R ４ Together, C２ By forming an alkylene chain, R ３ and R ４ represents a three-membered ring formed together with the carbon atom to which it is attached; Z represents Z-1; Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ The pyrazole compound or salt thereof according to the above

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

[0359]

[18] G １ represents a halogen atom; ３ and R ４ is R ３ and R ４ Together, C ４ By forming an alkylene chain, R ３ and R ４ represents a 5-membered ring formed together with the carbon atom to which it is attached; Z represents Z-1; Z １ represents a halogen atom; m5 represents an integer of 1; and n5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[16] above.

[0360]

[19] G represents G-1, １ is a halogen atom or C １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, R Ｘ -1, R Ｘ -2 or R Ｘ represents -5, and X １ is a halogen atom, cyano or C １ ~C ６ represents haloalkyl, R Ｙ represents a hydrogen atom, R １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom, R ３ represents a hydrogen atom, R ４represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1 or Z-9, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy or C １ ~C ６ m5 represents an integer of 1, u4 represents an integer of 2, u5 represents an integer of 1 or 2, n5 represents an integer of 1 or 2, and p represents an integer of 1. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0361]

[20] G １ is a halogen atom or C １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ represents alkyl, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ m5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[19] above.

[0362]

[21] G represents G-1, １ is a halogen atom or C １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom; ３ is a hydrogen atom, a hydroxyl, a halogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C６ represents alkyl, R ａ is a hydrogen atom or R ａ represents −1, and R ５ and R ６ represents a hydrogen atom; ７ is C １ ~C ６ alkyl, Z represents Z-1 or Z-8, Z １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or E-40; Z ａ is C １ ~C ６ m5 represents an integer of 1, n5 represents an integer of 1 or 2, n4 represents an integer of 1 or 2, v1 represents an integer of 1, r1 represents an integer of 1, and p represents an integer of 1. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0363]

[22] R ２ represents a hydrogen atom; ３ is a hydroxyl, halogen atom or C １ ~C ６ represents alkyl, R ａ represents a hydrogen atom, or a salt thereof.

[0364]

[23] G １ represents a halogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ is R ａ -1, Z represents Z-1, Z １ is C １ ~C ６ The pyrazole compound or salt thereof according to the above

[21] , wherein n5 represents an integer of 2.

[0365]

[24] G represents G-1, G-2, G-3, G-4, G-6, G-9, G-10 or G-11, １is a hydroxyl, halogen atom, C １ ~C ６ Haloalkyl, R ｂ C substituted with １ ~C ６ Alkoxy or C １ ~C ６ represents haloalkoxy; G ２ is C １ ~C ６ represents alkyl, R ｂ represents E-1 and R Ｘ is C １ ~C ６ represents alkyl, 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 ａ represents a hydrogen atom, Z represents Z-1, Z-8, Z-25, Z-26, Z-33 or Z-34, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or E-1; Z ａ is C １ ~C ６ represents haloalkyl; Z ２ represents E-1, p represents an integer of 1, m2 represents an integer of 0, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, n5 represents an integer of 1 or 2, n4 represents an integer of 2, n2 represents an integer of 0 or 1, and v5 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [3].

[0366]

[25] G represents G-1, １ is a halogen atom or C １ ~C ６ Z represents Z-1; Z １ is a halogen atom, C １ ~C６ Alkyl or C １ ~C ６ m5 represents an integer of 1; and n5 represents an integer of 1 or 2. The pyrazole compound or a salt thereof according to

[24] above.

[0367]

[26] G represents G-1, １ is a hydroxyl, 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, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -C(=NOH)NH ２, E-2, E-3, E-18, E-20, E-22, E-23, E-28, E-29, E-30, E-42, E-43, E-45, E-48, E-58, E-62 or E-63, R ｄ represents E-2 or E-4, R ｈ is hydroxy, C ３ ~C １０ cycloalkyl, E-1, E-2, E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; Z ａ is a cyano, a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfonyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -SO ２ R ｓ represents Z ｂ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ represents alkoxy, R ｓ is C １ ~C ６ represents haloalkyl, p represents an integer of 1, m5 represents an integer of 0 or 1, n5 represents an integer of 1, v1 represents an integer of 1, v2 represents an integer of 0 or 1, v3 represents an integer of 0, v4 represents an integer of 0, 1 or 2, and v5 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [3].

[0368]

[27] 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, Z represents Z-1, Z １ is a halogen atom or C １ ~C ６ The pyrazole compound or salt thereof according to the above

[26] , wherein R represents alkyl.

[0369]

[28] G represents G-1, 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 or R Ｘ represents −2, and R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z １ represents E-40, and Z ａ is a thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, di(C １ ~C ６ alkyl)amino, -C(=NORｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1, J-2, J-3 or J-5; ｊ is C １ ~C ６ Alkoxy, —C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ' or -N(R ｑ ) SO ２ R ｑ ', and R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino, J-2 or J-5; R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or J-5, ｑ is C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ represents alkyl, R ｒ is benzyl, C １ ~C ６ Alkyl, C１ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔ represents J-5, and Z ｃ is a halogen atom or C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 1, u4 represents an integer of 0, p represents an integer of 1, v1 represents an integer of 0 or 1, w5 represents an integer of 0 or 1, w7 represents an integer of 0, and w8 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1] to [3].

[0370]

[29] R Ｘ is C １ ~C ６ represents alkyl; Z ａ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ represents alkoxy, R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C１ ~C ６ m5 represents an integer of 1; and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to

[28] above.

[0371]

[30] G represents G-1, １ is a halogen atom or C １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents -C(R ａ ) (R ２ )-, R ２ represents a hydrogen atom; ３ represents a hydrogen atom; ４ represents a hydrogen atom; ａ represents a hydrogen atom, Z represents Z-1, Z １ represents E-41 or E-44, Z ａ is C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl or R ｊ C substituted with １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ m5 represents an integer of 0 or 1; n5 represents an integer of 1; p represents an integer of 1; and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of [1] to [3] above.

[0372]

[31] Z １ represents E-44, and Z ａ is C １ ~C ６ Alkyl or C ３ ~C １０cycloalkyl; and m5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[30] above.

[0373]

[32] Z １ represents E-41, and m5 represents an integer of 1. The pyrazole compound or salt thereof according to

[30] above.

[0374]

[33] G represents G-1, １ is a halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents —O—, R ３ represents a hydrogen atom; ４ represents a hydrogen atom, Z represents Z-1, Z-6, Z-8, Z-9, Z-10, Z-11, Z-18, Z-23, Z-26, Z-27, Z-28, Z-30, Z-33, Z-34, Z-41 or Z-42, Z １ is a carboxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkoxycarbonyl, R １２ C substituted with １ ~C ６ alkyl, E-2, E-3, E-18, E-20, E-21, E-23, E-28, E-29 or E-30; １２ is C １~C ６ represents alkoxy; Z ａ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C ３ ~C １０ represents cycloalkyl; Z ｂ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, n2 represents an integer of 0 or 1, n1 represents an integer of 1, p represents an integer of 1, v1 represents an integer of 1, v2 represents an integer of 0 or 1, and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0375]

[34] G １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ Z represents Z-1; Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ m5 represents an integer of 1; and n5 represents an integer of 1 or 2. The pyrazole compound or a salt thereof according to

[33] above.

[0376]

[35] G represents G-1, 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; １represents a hydrogen atom, W represents —O—, R ３ is C １ ~C ６ represents alkyl, R ４ represents a hydrogen atom, Z represents Z-1, Z １ is a cyano, a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ m5 represents an integer of 0 or 1; n5 represents an integer of 0 or 1; and p represents an integer of 1. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0377]

[36] Z １ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ m5 represents an integer of 1; and n5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[35] above.

[0378]

[37] G represents G-1, １ represents a halogen atom; Ｘ is C １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents —O—, R ３ represents a hydrogen atom; ４ represents a hydrogen atom, Z represents Z-27, Z ２ is R ｈ C substituted with １ ~C ６ alkyl, E-1, E-2 or E-3; R ｈ is C １ ~C ６ represents alkoxy; Z ａ is C １ ~C ６m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n2 represents an integer of 0, p represents an integer of 1, and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0379]

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

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

[0380]

[39] G represents G-1, １ is a halogen atom or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 or R Ｘ represents −2, and R Ｙ represents a hydrogen atom; １ represents a hydrogen atom, W represents —O—, R ３ represents a hydrogen atom; ４ represents a hydrogen atom, Z represents Z-1, Z １ is a carboxyl, cyano, halogen atom, C １ ~C ６ represents alkyl or E-40; Z ａ is C １ ~C ６ m5 represents an integer of 0 or 1, u4 represents an integer of 0, u5 represents an integer of 0, n5 represents an integer of 1 or 2, p represents an integer of 1, and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0381]

[40] G １ is a halogen atom or C １ ~C ６ represents haloalkyl, R Ｘ is C １ ~C ６ represents alkyl; Z １is a halogen atom or C １ ~C ６ m5 represents an integer of 1. The pyrazole compound or a salt thereof according to

[39] above.

[0382]

[41] G represents G-1, 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, W represents —O—, R ３ represents a hydrogen atom; ４ represents a hydrogen atom, Z represents Z-1 or Z-49, Z １ is a halogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkoxy, E-29, E-40, E-42 or E-63; R ｈ is C ３ ~C １０ cycloalkyl, E-2 or E-3; Z ａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl or di(C １ ~C ６ Z represents (alkyl)amino; ｂ is C １ ~C ６ Alkyl or R ｈ C substituted with １ ~C ６m5 represents an alkyl, m4 represents an integer of 0, 1 or 2, n5 represents an integer of 1, p represents an integer of 0 or 1, v1 represents an integer of 1, v2 represents an integer of 1, and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0383]

[42] Z represents Z-1, １ represents E-29, E-40, E-42 or E-63, m5 represents an integer of 0 or 1, n4 represents an integer of 1, n5 represents an integer of 1, and p represents an integer of 1. The pyrazole compound or a salt thereof according to the above

[41] .

[0384]

[43] Z １ is a halogen atom or C １ ~C ６ m5 represents an integer of 0 or 1; and p represents an integer of 0. The pyrazole compound or a salt thereof according to

[41] above.

[0385]

[44] G １ represents a halogen atom, Z represents Z-1, Z １ represents a halogen atom; m5 represents an integer of 1; n5 represents an integer of 1; and p represents an integer of 2. The pyrazole compound or a salt thereof according to

[41] above.

[0386]

[45] G represents G-1, 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, R １ represents a hydrogen atom, W represents —O—, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ represents a hydrogen atom, Z represents Z-1, Z１ represents E-40, and Z ａ is hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', and R ｋ is C １ ~C ６ represents alkyl, R ｋ ' represents a hydrogen atom, R ｍ Is Ji (C １ ~C ６ alkyl)amino or J-2, ｎ is C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｐ represents a hydrogen atom; ｐ ' represents J-5, and R ｑ is C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ represents alkyl, R ｒ is C １ ~C ６m5 represents an integer of 0 or 1, n5 represents an integer of 1, p represents an integer of 1, v1 represents an integer of 1, w5 represents an integer of 0, w8 represents an integer of 0, and w10 represents an integer of 0. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0387]

[46] Z ａ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', and R ｊ is C １ ~C ６ The pyrazole compound or salt thereof according to the above

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

[0388]

[47] G represents G-1, 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, W represents —O—, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ represents a hydrogen atom, Z represents Z-1, Z １ represents E-41, and Z ａ is C １ ~C ６ Alkyl, C ３ ~C １０Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or J-2, ｊ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 1, p represents an integer of 1, v1 represents an integer of 1, and w8 represents an integer of 0. The pyrazole compound or a salt thereof according to any one of the above [1], [2] and [4].

[0389]

[48] ​​Z ａ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl or di(C １ ~C ６ m5 represents an integer of 1; or a salt thereof.

[0390]

[49] Formula (1):

[0391] [In the formula, G represents G-1, and G-1 represents a structure represented by the following structural formula:

[0392] 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 ~C６ Alkyl sulfonyl or di(C １ ~C ６ G represents (alkyl)amino; 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 to 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,

[0393] X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X 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, 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, R Ｙ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R １ 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 ４is a hydrogen atom or C １ ~C ６ Z represents Z-1 to Z-49 or Z-50, and Z-1 to Z-50 each represent a structure represented by the following structural formula:

[0394] In addition, Z in Z-4 to Z-7 and Z-49 to Z-50 １ represents a substitution on an aromatic ring; Z １ 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 ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R １２ C substituted with １ ~C ６ Alkyl, -OR d , -NHC(O)R e , -C(O)NHR u , -C(=NOH)NH ２ , E-1 to E-56 or E-57; Z １ In the relationship, when n2 is an integer of 2, each Z １ may be the same as or different from each other, １ In the relationship, when n3 represents an integer of 2 or 3, each Z１ may be the same as or different from each other, １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, １ In the relationship, when n5 represents an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, １ In the relationship, when n6 represents an integer of 2, 3, 4, 5 or 6, each Z １ may be the same as or different from each other, １ In the relationship, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-56 or E-57; R d is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, R １０ C substituted with １ ~C ６ Alkyl, R １０ C substituted with １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-56 or E-57; R １０ , R １２ , and R ｈ are each independently cyano, C １ ~C ６ alkoxy, E-1 to E-56 or E-57; R ｅ is C １ ~C ６ Alkyl, C ３ ~C１０ Cycloalkyl, C １ ~C ６ Haloalkyl, R １１ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, benzyloxy, E-1 to E-56 or E-57; R １１ is cyano, C １ ~C ６ alkoxy, E-1 to E-56 or E-57; R ｕ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ alkoxy, benzyl, E-1 to E-56, or E-57, wherein E-1 to E-57 each represent a structure represented by the following structural formula:

[0395] Z ａ is a halogen atom, cyano, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ Alkoxycarbonyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; Z ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same as or different from each other, 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, ａ In the relationship, when v3 represents an integer of 2 or 3, each Z ａ may be the same as or different from each other, ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, ｂ is C １ ~C ６ represents alkyl, R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(═NOR ｋ ) R ｋ ', -C(O)R ｍ or -N(R ｐ ) C(O)R ｐ ', and R ｋ is a hydrogen atom or C １ ~C ６represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5, R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino or R ｔ C substituted with １ ~C ６ represents alkylamino, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｔ is C １ ~C ６ Alkoxy, C １ ~C ６ haloalkyl, J-1 to J-4, or J-5, wherein J-1 to J-5 each represent a structure represented by the following structural formula:

[0396] Z ｃ is C １ ~C ６ represents alkyl; Z ｃ In the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z ｃmay be the same as or different from each other, m5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, n3 represents an integer of 0, 1, 2 or 3, n2 represents an integer of 0, 1 or 2, n1 represents an integer of 0 or 1, 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, 1 or 2, v5 represents an integer of 0, 1, 2, 3, 4 or 5, v4 represents an integer of 0, 1, 2, 3 or 4, v3 represents an integer of 0, 1, 2 or 3, v2 represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0397]

[50] G １ is a halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 or R Ｘ represents −2, and R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ３represents a hydrogen atom, Z is Z-1, Z-6, Z-8, Z-9, Z-10, Z-17, Z-19, Z-23, Z-26, Represents Z-27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42 or Z-49, Z １ is a carboxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , represents E-2, E-3, E-18, E-20, E-24, E-26, E-31, E-32, E-33, E-40 or E-41, Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5, R ｄ is R ４ C substituted with １ ~C ６ represents alkyl, R １２ and R １２ are each independently C １ ~C ６ alkoxy, E-2 or E-3; Z ａ is a halogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, —C(O)R ｍ , -N(R ｎ ) ORｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , J-1 or J-2; R ｊ is C １ ~C ６ represents alkoxy, R ｍ represents J-2, and R ｎ is C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｑ is C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ represents alkyl, R ｒ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, u5 represents an integer of 0, u4 represents an integer of 0, v5 represents an integer of 0, v4 represents an integer of 0 or 1, v3 represents an integer of 0 or 1, v2 represents an integer of 0 or 1, v1 represents an integer of 1, and w8 represents an integer of 0. The pyrazole compound or a salt thereof according to the above

[49] .

[0398]

[51] 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, C１ ~C ６ Alkyl sulfonyl or di(C １ ~C ６ G represents (alkyl)amino; 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 to R Ｘ -3 or R Ｘ represents -4, and X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; X 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, 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, R Ｙ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R １ 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 or C １ ~C ６ alkyl; Z represents Z-1 to Z-49 or Z-50; Z １is a hydroxy, carboxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R ４ C substituted with １ ~C ６ Alkyl, -OR ｄ , -NHC(O)R ｅ , -C(O)NHR ｕ , -C(=NOH)NH ２ , E-1 to E-56 or E-57; Z １ In the relationship, when n2 is an integer of 2, each Z １ may be the same as or different from each other, １ In the relationship, when n3 represents an integer of 2 or 3, each Z １ may be the same as or different from each other, １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, １ In the relationship, when n5 represents an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, １In the relationship, when n6 represents an integer of 2, 3, 4, 5 or 6, each Z １ may be the same as or different from each other, １ In the relationship, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-56 or E-57; R ｄ is R １０ C substituted with １ ~C ６ Alkyl, R １０ C substituted with １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-56 or E-57; R １０ , R １２及び R ｈ are each independently cyano, C １ ~C ６ alkoxy, E-1 to E-56 or E-57; R ｅ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R １１ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, benzyloxy, E-1 to E-56 or E-57; R １１is cyano, C １ ~C ６ alkoxy, E-1 to E-56 or E-57; R ｕ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ alkoxy, benzyl, E-1 to E-56 or E-57; Z ａ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylcarbonyl or C １ ~C ６ represents an alkoxycarbonyl; Z ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, 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, ａ In the relationship, when v3 represents an integer of 2 or 3, each Z ａ may be the same as or different from each other, ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same as or different from each other, ｂ is C １ ~C ６m5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3 or 4, n3 represents an integer of 0, 1, 2 or 3, n2 represents an integer of 0, 1 or 2, n1 represents an integer of 0 or 1, 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, 1 or 2, v5 represents an integer of 0, 1, 2, 3, 4 or 5, v4 represents an integer of 0, 1, 2, 3 or 4, v3 represents an integer of 0, 1, 2 or 3, v2 represents an integer of 0, 1 or 2, and v1 represents an integer of 0 or 1.

[0399]

[52] G １ is a halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ cycloalkyl, benzyl or R Ｘ represents −1, and R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ３ represents a hydrogen atom, Z is Z-1, Z-6, Z-8, Z-9, Z-10, Z-17, Z-19, Z-23, Z-26, Represents Z-27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42 or Z-49, Z １ is a carboxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , E-2 or E-40; Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5, R ｄ is R １０ C substituted with １ ~C ６ represents alkyl, R １０ and R ｈ are each independently C １ ~C ６ alkoxy, E-2 or E-3; Z ａ is a halogen atom or C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, u5 represents an integer of 0, v5 represents an integer of 0, v4 represents an integer of 0 or 1, v3 represents an integer of 0, and v1 represents an integer of 1. The pyrazole compound or a salt thereof according to the above

[51] .

[0400]

[53] Formula (1):

[0401] [In the formula, G represents G-1 to G-10 or G-11, and G-1 to G-11 each represent a structure represented by the following structural formula:

[0402] G １ is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ 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, di(C １ ~C ６ represents —C(═NOR)R′, １ In the relationship, when m2 represents an integer of 2, each G １ may be the same as or different from each other, １ In the relationship, when m3 represents an integer of 2 or 3, each G １ may be the same as or different from each other, １ In the relationship, when m4 represents an integer of 2, 3 or 4, each G １ may be the same as or different from each other, 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, １ In the relationship, when m7 represents an integer of 2, 3, 4, 5, 6 or 7, each G １may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(=NOR)aminocarbonyl, phenyl, —C(=NOR)R′, E-1 to E-61 or E-62. １ ~C ６ R' represents alkyl; １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, R Ｘ -1 to R Ｘ -5 represents a structure represented by the following structural formula,

[0403] X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C６ represents alkoxy; X 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, 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, R ｃ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ represents —C(═NOR)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, a hydroxyl, a halogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached, ａ is a hydrogen atom, C １ ~C ６ Alkyl, R ａ -1 to R ａ-5 or R ａ represents −6, and R ａ -1 to R ａ -6 represents a structure represented by the following structural formula,

[0404] R ５ is a hydrogen atom or C １ ~C ６ represents alkyl, R ６ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents an integer of 2, two R ５ and two R ６ may be the same as or different from each other, R ７ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl or phenyl; R ８ is a hydrogen atom or C １ ~C ６ represents alkyl, R ９ is a hydrogen atom or C １ ~C ６ Z represents Z-1 to Z-61 or Z-62, and Z-1 to Z-62 each represent a structure represented by the following structural formula:

[0405] Z １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with１ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ NH ２ , -C(=NOH)NH ２ , E-1 to E-61 or E-62; Z １ In the relationship, when n2 is an integer of 2, each Z １ may be the same as or different from each other, １ In the relationship, when n3 represents an integer of 2 or 3, each Z １ may be the same as or different from each other, １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same as or different from each other, １ In the relationship, when n5 represents an integer of 2, 3, 4 or 5, each Z １ may be the same as or different from each other, １ In the relationship, when n7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same as or different from each other, ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-61 or E-62, ｄ is C２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Haloalkyl, R １０ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-61 or E-62, ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-61 or E-62, １０ is C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, —C(═NOR)R′, E-1 to E-61 or E-62, ｅ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, E-1 to E-61 or E-62, R ｆ is C １ ~C ６ Alkyl, C １ ~C ６Haloalkyl, di(C １ ~C ６ alkyl)amino, E-1 to E-61 or E-62, R ｇ is a hydrogen atom or tri(C １ ~C ４ E-1 to E-62 each represent a structure represented by the following structural formula:

[0406] Z ａ is cyano, halogen atom, thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkoxycarbonyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; 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 v3 represents an integer of 2 or 3, 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, ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same as or different from each other, ｂ is a hydrogen atom, C １ ~C ６ Alkyl or -SO ２ R ｓ represents R ｊ is cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, —C(═NOR ｋ ) R ｋ ', -C(O)R ｍ or -N(R ｐ ) C(O)R ｐ ', and R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5, R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, Rｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino or R ｔ C substituted with １ ~C ６ represents alkylamino, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｔ is C １ ~C ６ Alkoxy, C １ ~C ６ haloalkyl, J-1 to J-4, or J-5, wherein J-1 to J-5 each represent a structure represented by the following structural formula:

[0407] Z ｃ is C １ ~C ６ represents alkyl; Z ｃIn the relationship, when w5 represents an integer of 2, 3, 4 or 5, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w8 represents an integer of 2, 3, 4, 5, 6, 7 or 8, each Z ｃ may be the same as or different from each other, ｃ In the relationship, when w10 represents an integer of 2, 3, 4, 5, 6, 7, 8, 9 or 10, each Z ｃ may be the same as or different from each other, m2 represents an integer of 0, 1 or 2, m3 represents an integer of 0, 1, 2 or 3, m4 represents an integer of 0, 1, 2, 3 or 4, m5 represents an integer of 0, 1, 2, 3, 4 or 5, m7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, u4 represents an integer of 0, 1, 2, 3 or 4, u5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2, or 3; n2 represents an integer of 0, 1, or 2; n1 represents an integer of 0 or 1; p represents an integer of 0 or 1; r １ represents an integer of 1 or 2; ２represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, v2 represents an integer of 0, 1 or 2, v3 represents an integer of 0, 1, 2 or 3, v4 represents an integer of 0, 1, 2, 3 or 4, v5 represents an integer of 0, 1, 2, 3, 4 or 5, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0408]

[54] G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; ２ is C １ ~C ６ represents alkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ represents alkoxy or E-1, Ｘ is C １ ~C ６ Alkyl, C ３ ~C１０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, and R ５ represents a hydrogen atom; ６ represents a hydrogen atom; ７ is C １ ~C ６ Z represents Z-1, Z-3, Z-4, Z-8, Z-9, Z-11, Z-41, Z-42, Z-53, Z-58 or Z-60; Z １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -C(=NOH)NH ２, represents E-1 to E-3, E-20, E-22, E-23, E-28 to E-30, E-40, E-41, E-43 to E-45, E-58 or E-62, Z ２ represents E-2, and R ｄ represents E-2 or E-4, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; Z ａ represents a halogen atom, a thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-3 or J-5; R ｊis cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino or -N(R ｐ ) C(O)R ｐ ', and R ｋ is C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino or J-2, ｎ ' is C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ represents alkoxy or J-5, ｑ ' is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｒ is benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔrepresents J-5, m2 represents an integer of 0 or 1, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0, 1 or 2, u5 represents an integer of 0 or 2, n7 represents an integer of 0, n5 represents an integer of 1, 2 or 3, n4 represents an integer of 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 1, n1 represents an integer of 1, r １ represents an integer of 1, v1 represents an integer of 0 or 1, v2 represents an integer of 0 or 1, v4 represents an integer of 0, 1 or 2, v5 represents an integer of 1, w5 represents an integer of 0, w7 represents an integer of 0, w8 represents an integer of 0 or 1, and w10 represents an integer of 0. The pyrazole compound or a salt thereof according to the above

[53] .

[0409]

[55] 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 ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C ２ ~C ６ Alkylsulfinyl, C ２ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl, di(C １ ~C ６ represents —C(═NOR)R′, ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(=NOR)aminocarbonyl, phenyl, —C(=NOR)R′, E-1 to E-60 or E-61. １ ~C ６ R' represents alkyl; １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６represents alkoxy, R ｃ is cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ represents —C(═NOR)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, a hydroxyl, a halogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached, ａ is a hydrogen atom, C １ ~C ６ Alkyl, R ａ -1 to R ａ -5 or R ａ represents −6, and R ５ is a hydrogen atom or C １ ~C ６ represents alkyl, R ６ is a hydrogen atom or C １ ~C ６ represents alkyl, １ represents an integer of 2, two R ５and two R ６ may be the same as or different from each other, R ７ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ represents haloalkyl or phenyl; R ８ is a hydrogen atom or C １ ~C ６ represents alkyl, R ９ is a hydrogen atom or C １ ~C ６ alkyl; Z represents Z-1 to Z-61 or Z-62; Z １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ NH ２ , E-1 to E-60 or E-61; Z２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-60 or E-61; R ｄ is C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Haloalkyl, R １０ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-60 or E-61, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-60 or E-61, R １０ is C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C １ ~C ６ alkyl)aminocarbonyl, —C(═NOR)R′, E-1 to E-60 or E-61, ｅ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６Alkylamino, di(C １ ~C ６ alkyl)amino, E-1 to E-60 or E-61, R ｆ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, di(C １ ~C ６ alkyl)amino, E-1 to E-60 or E-61, R ｇ is a hydrogen atom or tri(C １ ~C ４ represents alkyl)silyl; Z ａ is a cyano, a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; Z ｂ is C １ ~C ６ m2 represents an integer of 0, 1 or 2, m3 and n3 represent an integer of 0, 1, 2 or 3, m4 and n4 represent an integer of 0, 1, 2, 3 or 4, m5, n5 and u5 each independently represent an integer of 0, 1, 2, 3, 4 or 5, u4 represents an integer of 0, 1, 2, 3 or 4, u5 represents an integer of 0, 1, 2, 3, 4 or 5, m7 and n7 represent an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2, or 3; n2 represents an integer of 0, 1, or 2; n1 represents an integer of 0 or 1; p represents an integer of 0 or 1; r １ represents an integer of 1 or 2; ２represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, v2 represents an integer of 0, 1 or 2, v3 represents an integer of 0, 1, 2 or 3, v4 represents an integer of 0, 1, 2, 3 or 4, and v5 represents an integer of 0, 1, 2, 3, 4 or 5. The pyrazole compound or a salt thereof according to the above

[53] .

[0410]

[56] G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents alkylsulfonyl; ２ is C １ ~C ６ represents alkyl, R ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl or C １ ~C ６ represents alkoxy or E-1, Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -3 or R Ｘ represents −4, and R Ｙ represents a hydrogen atom, R １represents a hydrogen atom, R ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, and R ５ represents a hydrogen atom, R ６ represents a hydrogen atom, R ７ is C １ ~C ６ Z represents Z-1, Z-3, Z-4, Z-8, Z-11, Z-41, Z-42, Z-53, Z-58 or Z-60; Z １ is a hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , E-1 to E-3, E-41 or E-58; Z ２ represents E-2, and R ｄ represents E-2 or E-4, R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C６ m2 represents an integer of 0 or 1; m3 represents an integer of 0 or 1; m4 represents an integer of 1; m5 represents an integer of 0, 1 or 2; m7 represents an integer of 0; r １ represents an integer of 1, n7 represents an integer of 0, n5 represents an integer of 1, 2 or 3, n4 represents an integer of 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 1, n1 represents an integer of 1, u4 represents an integer of 0, u5 represents an integer of 0, v1 represents an integer of 1, v2 represents an integer of 1, v4 represents an integer of 0, 1 or 2, and v5 represents an integer of 1. The pyrazole compound or a salt thereof according to the above

[55] .

[0411]

[57] Formula (1-1a):

[0412] [In the formula, R ｚ is R ｚ -1, R ｚ -2 or R ｚ represents -3, and R ｚ -1, R ｚ -2 and R ｚ -3 represents a structure represented by the following structural formula,

[0413] R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that Z forms a 3- to 6-membered ring together with the carbon atom to which it is attached; １ represents E-40 or E-41, and E-40 and E-41 each represent a structure represented by the following structural formula:

[0414] Z ａis hydroxy, C １ ~C ６ Alkyl, difluoromethyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', and R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ J-1 to J-5 each represent a structure represented by the following structural formula:

[0415] R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C１ ~C ６ alkyl, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｒ is C １ ~C ６ represents alkyl, R ｖ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl, R ｗ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６

[0039] wherein v1 represents an integer of 1, w5 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0416]

[58] Formula (1-1a):

[0417] [In the formula, R ｚ is R ｚ -1, R ｚ -2 or R ｚ represents -3, and R ｚ -1, R ｚ -2 and R ｚ -3 represents a structure represented by the following structural formula,

[0418] R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that Z forms a 3- to 6-membered ring together with the carbon atom to which it is attached; １ represents E-18, E-20, E-22, E-23, E-24, E-28, E-29, E-30, E-42 or E-63, and E-18, E-20, E-22, E-23, E-24, E-28, E-29, E-30, E-42 and E-63 each represent a structure represented by the following structural formula:

[0419] Z ａ is C ２ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) SO ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; Z ａ In the relationship, when v2 represents an integer of 2, each Z ａmay be the same as or different from each other, ｂ is C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ Alkyl or -SO ２ R ｓ represents R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', and R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ J-1 to J-5 each represent a structure represented by the following structural formula:

[0420] R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｒ is C １ ~C ６represents alkyl, R ｖ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl, R ｗ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６

[0039] The intermediate or salt thereof for producing the pyrazole compound according to any one of the above [1], [2], [4] to

[10] , and

[33] to

[48] , wherein: v1 represents an integer of 1, v2 represents an integer of 1 or 2, w5 represents an integer of 0, 1, 2, 3, 4, or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0421]

[59] R ４ represents a hydrogen atom; Z ａ is C １ ~C ６ Alkyl, difluoromethyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , J-1 or J-2; R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', and R ｋ ' represents a hydrogen atom, R ｍ Is Ji (C１ ~C ６ alkyl)amino or J-2, ｐ represents a hydrogen atom, R ｐ ' represents J-5, and R ｖ is C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy, R ｗ is C １ ~C ６ w5 represents an integer of 0; w8 represents an integer of 0; and w10 represents an integer of 0. The intermediate or a salt thereof according to

[58] above.

[0422]

[60] R ３ represents a hydrogen atom, R ４ represents a hydrogen atom; Z ａ is C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylamino or di(C １ ~C ６ Z represents (alkyl)amino; ｂ is C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ represents alkoxy, R ｖ is C １ ~C ６ represents alkoxy, R ｗ is C １ ~C ６ The intermediate or salt thereof according to the above

[59] , wherein R represents alkyl.

[0423]

[61] Formula (1-2a):

[0424] W １ is -OR １３ or -N(R １ ) OH, G １is a hydroxy, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ 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, di(C １ ~C ６ represents —C(═NOR)R′, ｂ is cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(=NOR)aminocarbonyl, phenyl or -C(=NOR)R'１ ~C ６ R' represents alkyl; １ ~C ６ represents alkyl, R Ｙ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl, R １ is a hydrogen atom or C １ ~C ６ represents alkyl, R １３ is a hydrogen atom or C １ ~C ６

[0023] The intermediate for producing the pyrazole compound according to any one of [1] to

[56] above, or a salt thereof, is represented by the formula:

[0425]

[62] W １ is -OR １３ represents １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy, R Ｙ represents a hydrogen atom, R １３ represents a hydrogen atom or a salt thereof according to

[61] above.

[0426]

[63] W １ is -N(R １ ) OH, G １ represents a halogen atom; Ｙ represents a hydrogen atom, R １ represents a hydrogen atom or a salt thereof according to

[61] above.

[0427]

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

[56] above.

[0428]

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

[56] above.

[0429]

[66] 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

[56] above.

[0430]

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

[56] above.

[0431]

[68] 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

[56] above.

[0432] 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.

[0433] The medium pressure preparative liquid chromatography described in the synthesis examples was carried out using a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).

[0434] 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.

[0435] s: singlet, d: doublet, dd: double doublet, t: triplet, dt: double triplet, q: quartet, sep: septet, m: multiplet, br: broad singlet.

[0436] still, １ The solvent name and reference frequency (MHz) used in the H-NMR measurement are shown in parentheses in the chemical shift value data.

[0437] The retention times (hereinafter referred to as Rt) and associated mass ions (hereinafter referred to as m / z) of the liquid chromatography mass spectrometry (LC / MS) described below were measured by ESI (electrospray ionization) or APCI (atmospheric pressure chemical ionization) under the following conditions. In each chromatography and experimental procedure, "number / number" refers to the volume ratio of each solvent unless otherwise specified.

[0438] [LC / MS conditions] Apparatus: NexeraX2 LC-30 (Shimadzu Corporation) / LCMS-2020 (ESI / APCI mode, Shimadzu Corporation) Column: InertSustain Phenyl column (GL Sciences, 2.1 x 30 mm, 2 µm) Column temperature: 40°C Injection volume: 2 µL Solvent: Solution A: 0.1 vol% formic acid aqueous solution Solution B: 0.1 vol% formic acid-acetonitrile solution Gradient conditions: After starting the measurement at a flow rate of 0.3 mL / min and a mixing ratio of solution A to solution B of 60 / 40, the mixing ratio of solution A to solution B was changed linearly to 5 / 95 over 5 minutes.

[0439] Thereafter, the mixture ratio of solution A and solution B was fixed at 5 / 95 for 0.3 minutes.

[0440] Detection wavelength: PDA (190-600 nm) [Synthesis Examples] Synthesis Example 1: Synthesis of 1-(tert-butyl)-N-(2,4-dichlorophenethyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxamide (Compound No. 2-001) Step 1: Synthesis of 3-(dimethylamino)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-one To a mixed solution of 2.66 g of 1-(3-(trifluoromethyl)phenyl)ethan-1-one and 14 ml of toluene, 2.01 g of N,N-dimethylformamide dimethyl acetal was added at room temperature, and the mixture was stirred at 110°C for 1 day. 0.5 g of N,N-dimethylformamide dimethyl acetal was added to the reaction mixture, and the mixture was stirred for 1 day. After completion of the reaction, the solvent was distilled off under reduced pressure, and 3.48 g of the target product was obtained as a brown oil. 1H-NMR (CDCl3) δ: 8.13 (s, 1H), 8.09-8.05 (m, 1H), 7.85 (d, J = 12.3 Hz, 1H), 7.72-7.67 (m, 1H), 7.56-7.50 (m, 1H), 5.69 (d, J = 12.3 Hz, 1H), 3.18 (br s, 3H), 2.95 (br s, 3H).

[0441] Step 2: Synthesis of ethyl 4-(dimethylamino)-2-oxo-3-(3-(trifluoromethyl)benzoyl)but-3-enoate To a mixed solution of 3.48 g of 3-(dimethylamino)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-one and 28 ml of dichloromethane, 1.23 g of pyridine was added at room temperature. The reaction mixture was ice-cooled to 0°C, and then a mixed solution of 2.02 g of ethyl 2-chloro-2-oxoacetate and 28 ml of dichloromethane was added, followed by stirring at room temperature for 1 day. After completion of the reaction, 50 ml of water was added at room temperature, and the mixture was extracted with dichloromethane (20 ml × 1). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 5.42 g of the target product as a brown oil. 1 H-NMR (CDCl3) δ: 7.99 (s, 1H), 7.95-7.84 (m, 2H), 7.77-7.72 (m, 1H), 7.59-7.50 (m, 1H), 3.90 (q, J = 7.2 Hz, 2H), 3.37 (s, 3H), 2.83 (s, 3H), 1.10 (t, J = 7.2 Hz, 3H).

[0442] Step 3: Synthesis of ethyl 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylate To a mixed solution of 5.42 g of ethyl (Z)-4-(dimethylamino)-2-oxo-3-(3-(trifluoromethyl)benzoyl)but-3-enoate and 140 ml of ethanol, 1.93 g of tert-butylhydrazine hydrochloride was added, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue, 33 ml of ethyl acetate and 67 ml of n-hexane were added, and the mixture was washed with a saturated aqueous solution of sodium bicarbonate. The mixture was then purified by silica gel column chromatography using n-hexane:ethyl acetate = 2:1 (volume ratio, the same applies hereinafter) as an eluent, and 4.99 g of the target product was obtained as an orange oil. 1 H -NMR (CDCl3) δ: 8.10 (s, 1H), 8.03-7.99 (m, 1H), 7.85-7.80 (m, 1H), 7.68 (s, 1H), 7.65-7.60 (m, 1H), 4.39 (q, J = 7.2 Hz, 2H), 1.70 (s, 9H), 1.36 (t, J = 7.2 Hz, 3H).

[0443] Step 4: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylic acid To a mixed solution of 4.94 g of ethyl 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylate and 26 ml of ethanol, a mixed solution of 1.61 g of sodium hydroxide and 13 ml of water was added, and the mixture was stirred at room temperature for 1 day. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 300 ml of water was added, and the aqueous layer was washed with chloroform (50 ml × 1 time) and then with n-hexane (20 ml × 1 time). To the obtained aqueous layer, 35% by mass hydrochloric acid was added until the pH reached 3. The precipitated solid was filtered and dried under reduced pressure to obtain 3.94 g of the target product as a white solid. Melting point: 154-156°C.

[0444] Step 5: Synthesis of 1-(tert-butyl)-N-(2,4-dichlorophenethyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxamide (Compound No. 2-001) To a mixed solution of 1 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylic acid and 9 ml of N,N-dimethylformamide, 1.68 g of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 0.38 g of diisopropylethylamine, and 0.67 g of 2-(2,4-dichlorophenyl)ethan-1-amine were added and stirred at room temperature for 1 day. After completion of the reaction, 30 ml of water was added at room temperature, and the mixture was extracted with ethyl acetate (30 ml x 1). The resulting organic layer was purified by silica gel column chromatography using ethyl acetate as an eluent. After distilling off the solvent, the resulting crude product was washed with diisopropyl ether to give 1.48 g of the target product as a pink solid. Melting point: 127-129°C.

[0445] Synthesis Example 2: Synthesis of 1-(tert-butyl)-4-(3-fluorobenzoyl)-N-(4-methylphenethyl)-1H-pyrazole-5-carboxamide (Compound No. 2-125) Step 1: Synthesis of 1-(tert-butyl)-4-iodo-N-(4-methylphenethyl)-1H-pyrazole-5-carboxamide To a mixed solution of 4.23 g of 1-(tert-butyl)-4-iodo-1H-pyrazole-5-carboxylic acid and 32 ml of N,N-dimethylformamide were added 8.21 g of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, 5.58 g of diisopropylethylamine, and 2.34 g of 2-(p-tolyl)ethan-1-amine, and the mixture was stirred at room temperature for 4 days. After the reaction was completed, 100 ml of water was added at room temperature, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate = 1:1 (volume ratio, the same applies hereinafter) (100 ml x 3 times). 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 98:2 to 80:20) as the eluent. The obtained crude product was purified by amino silica gel column chromatography using n-hexane:ethyl acetate (gradient from 95:5 to 0:100) as the eluent, yielding 3.8 g of the target product as a white solid. Melting point: 62-64°C.

[0446] Step 2: Synthesis of 1-(tert-butyl)-4-(3-fluorobenzoyl)-N-(4-methylphenethyl)-1H-pyrazole-5-carboxamide A mixed solution of 22 mg of potassium bicarbonate, 22 mg of palladium acetate (divalent), N-cyclohexylpicolinamide, and 2 ml of tert-amyl alcohol was stirred at room temperature for 3 minutes. 200 mg of 1-(tert-butyl)-4-iodo-N-(4-methylphenethyl)-1H-pyrazole-5-carboxamide and 181 mg of 3-fluorobenzaldehyde were added to the mixed solution, and the mixture was stirred at 145°C for 3 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and filtered. Water was added to the filtrate, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate = 1:5. The resulting organic layer was dehydrated and dried over 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 (gradient from 80:20 to 60:40) as an eluent to obtain 151 mg of the desired product as an oil.

[0447] Synthesis Example 3: Synthesis of N-(4-(2-(1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide)ethyl)phenyl)picolinamide (Compound No. 10-026) To a mixed solution of 100 mg of N-(4-aminophenethyl)-1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide and 1 ml of dichloromethane, 57 mg of pyridine and 51 mg of picolinoyl chloride hydrochloride were added at 0°C, and the mixture was stirred at room temperature for 1 day. After completion of the reaction, water was added at room temperature, and the mixture was extracted with dichloromethane. The resulting organic layer was dehydrated and dried over 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 (gradient from 100:0 to 55:45) as an eluent to obtain 44 mg of the target product as a solid. Melting point: 182-184°C.

[0448] Synthesis Example 4: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(2-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)ethyl)-1H-pyrazole-5-carboxamide (Compound No. 11-001) Step 1: Synthesis of 3-(1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide)propanoic acid To a mixed solution of 4.04 g of methyl 3-(1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide)propanoate, 41.2 ml of ethanol, and 10.3 ml of water, 824 mg of sodium hydroxide was added, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The residue was washed with isopropyl ether to obtain 2.86 g of the target product as a white solid. Melting point: 166-168°C.

[0449] Step 2: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(2-(5-(pyridin-2-yl)-1,3,4-oxadiazol-2-yl)ethyl)-1H-pyrazole-5-carboxamide To a mixed solution of 378 mg of 3-(1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide)propanoic acid and 2 ml of tetrahydrofuran, 324 mg of 1,1′-carbonyldiimidazole was added at 0° C., and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 959 mg of picolinohydrazide was added, and the mixture was stirred at 60° C. for 3 hours. After completion of the reaction, a saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with chloroform (10 ml×3 times). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To a mixed solution of the obtained residue and 2 ml of 1,2-dichloroethane, 476.6 mg of methyl N-(triethylammoniumsulfonyl)carbamate was added, and the mixture was stirred at 85°C for 1 hour. 1.43 g of methyl N-(triethylammoniumsulfonyl)carbamate was added to the reaction mixture, and the mixture was stirred at 85°C for 3 hours. After completion of the reaction, water was added at room temperature, and the mixture was extracted with chloroform. 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 100:0 to 20:80) as an eluent, and 280 mg of the target product was obtained as an oil. 1 H-NMR (CDCl3) δ: δ8.77-8.71 (m, 1H), 8.14-8.08 (m, 1H), 7.90-7.81 (m, 1H), 7.63-7.28 (m, 7H), 4.05-3.95 (m, 2H), 3.39-3.31 (m, 2H), 1.71 (s, 9H).

[0450] Synthesis Example 5: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(2-(3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)ethyl)-1H-pyrazole-5-carboxamide (Compound No. 12-001) To a mixed solution of 378 mg of 3-(1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxamide)propanoic acid and 2 ml of dichloromethane were added 288 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 165 mg of N'-hydroxypicolinimidamide, 152 mg of triethylamine, and 3 mg of 1-hydroxy-7-azabenzotriazole, successively, at room temperature, and the mixture was stirred at the same temperature for 1 day. After completion of the reaction, water was added at room temperature, and the mixture was extracted with chloroform (5 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. 1 ml of pyridine was added to the resulting residue, and the mixture was stirred at 80°C for 3 hours. After completion of the reaction, 1 mol / l hydrochloric acid was added to the reaction mixture until the pH reached 7, and the mixture was extracted with ethyl acetate. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 100:0 to 50:50) as the eluent, and 230 mg of the target product was obtained as an oil. 1H-NMR (CDCl) δ: 8.72-8.67 (br m, 1H), 8.00-7.94 (m, 1H), 7.82-7.74 (m, 1H), 7.65-7.35 (m, 6H), 7.32-7.24 (m, 1H), 4.03-3.94 (m, 2H), 3.41-3.32 (m, 2H), 1.71 (s, 9H). Synthesis Example 6: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-((5-chloropyridin-2-yl)methoxy)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 10-012) To a mixed solution of 128 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-hydroxyphenethyl)-1H-pyrazole-5-carboxamide and 1.5 mL of N,N-dimethylformamide, 77.6 mg of potassium carbonate, 5 mg of potassium iodide, and 58.3 mg of 5-chloro-2-(chloromethyl)pyridine were added sequentially at room temperature, and the mixture was stirred at 80°C for 2 hours. After completion of the reaction, 1 mL of water was added at room temperature, and the mixture was dehydrated and dried over diatomaceous earth, 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 100:0 to 65:35) as an eluent, to obtain 105 mg of the target product as an oil. 1 H-NMR (CDCl3) δ: 8.55-8.52 (m, 1H), 7.78 (br s, 1H), 7.70-7.64 (m, 2H), 7.59-7.52 (m, 2H), 7.49-7.37 (m, 2H), 7.16-7.09 (m, 2H), 6.92-6.78 (m, 3H), 5.11 (s, 2H), 3.70-3.59 (m, 2H), 2.91-2.81 (m, 2H), 1.68 (s, 9H).

[0451] Synthesis Example 7: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(3-methyl-1,2,4-oxadiazol-5-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 19-001) To a mixed solution of 767 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxylic acid and 5 ml of toluene, 390 mg of oxalyl chloride and 18 mg of N,N-dimethylformamide were added successively under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and 2 ml of toluene was added to the resulting residue. The reaction mixture was added to a mixed solution of 605 mg of 4-(2-aminoethyl)benzoic acid hydrochloride, 2.5 ml of a 3 mol / l aqueous sodium hydroxide solution, 3 ml of toluene, and 1.3 ml of water under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 35% by mass hydrochloric acid was added to the reaction mixture until the pH reached 7, and the mixture was extracted with ethyl acetate (5 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To a mixed solution of the resulting residue and 2 ml of dichloromethane, 719 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 222 mg of acetamide oxime, 380 mg of triethylamine, and 3 mg of 1-hydroxy-7-azabenzotriazole were added sequentially at room temperature, and the mixture was stirred at the same temperature for 1 day. After completion of the reaction, water was added at room temperature, and the mixture was extracted with chloroform (5 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. 1 ml of pyridine was added to the resulting residue, and the mixture was stirred at 80°C for 1 day. After completion of the reaction, 1 mol / l hydrochloric acid was added to the reaction mixture until the pH reached 7, and the mixture was extracted with ethyl acetate. The resulting organic layer was dehydrated and dried over 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 (gradient from 100:0 to 60:40) as an eluent to obtain 186 mg of the target product as a solid. Melting point: 134-136°C.

[0452] Synthesis Example 8: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-005) To a mixed solution of 767 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxylic acid and 5 ml of toluene, 390 mg of oxalyl chloride and 18 mg of N,N-dimethylformamide were added sequentially under ice-cooling, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and 5 ml of toluene was added to the resulting residue. The reaction mixture was added to a mixed solution of 502 mg of 4-(2-aminoethyl)benzonitrile hydrochloride, 2.5 ml of a 3 mol / l aqueous sodium hydroxide solution, 3 ml of toluene, and 1.3 ml of water under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, 35% by mass hydrochloric acid was added to the reaction mixture until the pH reached 7, and the mixture was extracted with ethyl acetate (5 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. 83 mg of 50% by mass aqueous hydroxylamine solution was added to a mixed solution of the resulting residue and 5 ml of methanol, and the mixture was stirred at room temperature for 1 day. After the reaction was completed, the solvent was distilled off from the reaction mixture under reduced pressure. 297 mg of pyridine and 243 mg of propionyl chloride were added sequentially to a mixed solution of the resulting residue and 5 ml of toluene, and the mixture was stirred at room temperature for 10 minutes, and then stirred at 90°C for 1 day. After the reaction was completed, 35% by mass hydrochloric acid was added to the reaction mixture until the pH reached 4, and the mixture was extracted with ethyl acetate (5 ml x 2). The resulting organic layer was dehydrated and dried over 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 (gradient from 100:0 to 70:30) as an eluent to give 690 mg of the desired product as a solid, melting point: 127-129°C.

[0453] Synthesis Example 9: Synthesis of 1-(tert-butyl)-4-(3-methylbenzoyl)-N-(4-(5-(N-methylmethylsulfonamido)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-110) Step 1: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-mercapto-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide To a mixed solution of 800 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(N'-hydroxycarbamimidoyl)phenethyl)-1H-pyrazole-5-carboxamide and 8.6 ml of 1,4-dioxane, 306 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene and 365 mg of 1,1'-thiocarbonyldiimidazole were added at room temperature, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 4 ml of 1 mol / l hydrochloric acid and 50 ml of water were added at room temperature, and the mixture was extracted with chloroform (50 ml x 3 times). The solvent was distilled off from the obtained organic layer under reduced pressure, and 800 mg of the target product was obtained as a solid. Melting point: 192-194°C.

[0454] Step 2: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(N-methylmethylsulfonamido)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-110) To a mixed solution of 770 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-mercapto-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide, 313 mg of potassium carbonate, and 7.6 ml of N,N-dimethylformamide, 321 mg of iodomethane was added at room temperature, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 10 ml of saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate=1:1. The solvent was evaporated under reduced pressure from the obtained organic layer. To a mixed solution of the obtained residue and 15 ml of dichloromethane, 447 mg of metachloroperbenzoic acid was added at 0°C, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, 20 ml of dichloromethane was added to the reaction mixture, followed by 10 ml of saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was extracted with dichloromethane (100 ml x 3). The solvent was evaporated from the obtained organic layer under reduced pressure. To a mixed solution of 18 mg of N-methylmethanesulfonamide and 1 ml of dichloromethane, 18 mg of potassium tert-butoxide and 40 mg of the obtained residue were added, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 5 ml of saturated aqueous ammonium chloride was added at room temperature, and the mixture was extracted with chloroform (15 ml x 3). The solvent was evaporated from the obtained organic layer under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 100:0 to 40:60) as an eluent to obtain 30 mg of the desired product as a solid. 1H-NMR (CDCl3) δ: 7.96-7.88 (m, 2H), 7.79-7.76 (m, 1H), 7.67-7.64 (m, 1H), 7.61-7.51 (m, 2H), 7.46-7.37 (m, 1H), 7.35-7.31 (m, 2H), 7.10-6.98 (m, 1H), 3.77-3.69 (m, 2H), 3.59 (s, 3H), 3.43 (s, 3H), 3.00 (t, J = 7.2 Hz, 2H), 1.66 (s, 9H). Synthesis Example 10: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-morpholino-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-102) and 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(morpholine-4-carbonyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-103) A mixed solution of 60 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(trichloromethyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide and 1 ml of morpholine was stirred at room temperature for 12 hours. After completion of the reaction, 2 ml of 1 mol / l hydrochloric acid was added at room temperature, and the mixture was extracted with chloroform (20 ml x 3 times). The solvent was distilled off from the obtained organic layer under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 100:0 to 50:50) as an eluent to give 13 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-morpholino-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide as a solid and 21 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(morpholino-4-carbonyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide as an oil.

[0455] 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-morpholino-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-102) Melting point: 174-175°C.

[0456] 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(morpholine-4-carbonyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-103) 1 H-NMR (CDCl3) δ: 8.00-7.97 (m, 2H), 7.79-7.78 (m, 1H), 7.70-7.66 (m, 1H), 7.61-7.54 (m, 2H), 7.45-7.37 (m, 3H), 7.10-7.06 (m, 1H), 3.92-3.67 (m, 10H), 3.02 (t, J = 7.2 Hz, 2H), 1.69 (s, 9H).

[0457] Synthesis Example 11: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-(N-ethylsulfamoyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide (Compound No. 18-124) To a mixed solution of 100 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-(4-(5-mercapto-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide and 1 ml of 1,2-dichloroethane was added 0.3 ml of a 2 mol / l ethylamine tetrahydrofuran solution at room temperature, and the mixture was stirred at room temperature for 10 minutes. 27 mg of N-chlorosuccinimide was added at room temperature, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was filtered, and the solvent was evaporated from the filtrate under reduced pressure. To a mixed solution of the obtained residue and 0.8 ml of ethanol, 60 mg of ammonium molybdate (tetravalent) tetrahydrate and 180 μl of 35% by mass aqueous hydrogen peroxide solution were added at 0°C, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added at 0°C, and the mixture was extracted with dichloromethane (20 ml x 3). The obtained organic layer was washed with saturated brine, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 100:0 to 50:50) as an eluent, and 35 mg of the target product was obtained as an oil. 1 H-NMR (CDCl3) δ: 8.00-7.92 (m, 2H), 7.78-7.77 (m, 1H), 7.71-7.64 (m, 1H), 7.59-7.52 (m, 2H), 7.45-7.36 (m, 3H), 7.15-7.09 (m, 1H), 5.66-5.52 (m, 1H), 3.76-3.71 (m, 2H), 3.46-3.40 (m, 2H), 3.00 (t, J = 7.2 Hz, 2H), 1.77-1.62 (m, 9H), 1.36-1.18 (m, 3H).

[0458] Synthesis Example 12: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxamide (Compound No. 21-003) Step 1: Synthesis of 3-(dimethylamino)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-one.

[0459] To a mixed solution of 2.66 g of 1-(3-(trifluoromethyl)phenyl)ethan-1-one and 14 ml of toluene, 2.01 g of N,N-dimethylformamide dimethyl acetal was added at room temperature, and the mixture was stirred at 110°C for 1 day. 0.5 g of N,N-dimethylformamide dimethyl acetal was added to the reaction mixture, and the mixture was stirred for 1 day. After completion of the reaction, the solvent was distilled off under reduced pressure, and 3.48 g of the target product was obtained as a brown oil. 1 H-NMR (CDCl3) δ: 8.13 (s, 1H), 8.09-8.05 (m, 1H), 7.85 (d, J = 12.3 Hz, 1H), 7.72-7.67 (m, 1H), 7.56-7.50 (m, 1H), 5.69 (d, J = 12.3 Hz, 1H), 3.18 (br s, 3H), 2.95 (br s, 3H).

[0460] Step 2: Synthesis of ethyl 4-(dimethylamino)-2-oxo-3-(3-(trifluoromethyl)benzoyl)but-3-enoate To a mixed solution of 3.48 g of 3-(dimethylamino)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-one and 28 ml of dichloromethane, 1.23 g of pyridine was added at room temperature. The reaction mixture was ice-cooled to 0°C, and then a mixed solution of 2.02 g of ethyl 2-chloro-2-oxoacetate and 28 ml of dichloromethane was added, followed by stirring at room temperature for 1 day. After completion of the reaction, 50 ml of water was added at room temperature, and the mixture was extracted with dichloromethane (20 ml × 1). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 5.42 g of the target product as a brown oil. 1H-NMR (CDCl3) δ: 7.99 (s, 1H), 7.95-7.84 (m, 2H), 7.77-7.72 (m, 1H), 7.59-7.50 (m, 1H), 3.90 (q, J = 7.2 Hz, 2H), 3.37 (s, 3H), 2.83 (s, 3H), 1.10 (t, J = 7.2 Hz, 3H).

[0461] Step 3: Synthesis of ethyl 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylate To a mixed solution of 5.42 g of ethyl 4-(dimethylamino)-2-oxo-3-(3-(trifluoromethyl)benzoyl)but-3-enoate and 140 ml of ethanol, 1.93 g of tert-butylhydrazine hydrochloride was added, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the residue, 33 ml of ethyl acetate and 67 ml of n-hexane were added, and the mixture was washed with a saturated aqueous solution of sodium bicarbonate. The mixture was then purified by silica gel column chromatography using n-hexane:ethyl acetate = 2:1 (volume ratio) as an eluent, and 4.99 g of the target product was obtained as an orange oil. 1 H -NMR (CDCl3) δ: 8.10 (s, 1H), 8.03-7.99 (m, 1H), 7.85-7.80 (m, 1H), 7.68 (s, 1H), 7.65-7.60 (m, 1H), 4.39 (q, J = 7.2 Hz, 2H), 1.70 (s, 9H), 1.36 (t, J = 7.2 Hz, 3H).

[0462] Step 4: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylic acid To a mixed solution of 4.94 g of ethyl 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylate and 26 ml of ethanol, a mixed solution of 1.61 g of sodium hydroxide and 13 ml of water was added, and the mixture was stirred at room temperature for 1 day. After completion of the reaction, the solvent was distilled off under reduced pressure. To the obtained residue, 300 ml of water was added, and the aqueous layer was washed with chloroform (50 ml × 1 time) and then with n-hexane (20 ml × 1 time). To the obtained aqueous layer, 35% by mass hydrochloric acid was added until the pH reached 3. The precipitated solid was filtered and dried under reduced pressure to obtain 3.94 g of the target product as a white solid. Melting point: 154-156°C.

[0463] Step 5: Synthesis of 1-(tert-butyl)-N-((2,4-dimethylbenzyl)oxy)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxamide (Compound No. 21-003) To a mixed solution of 100 mg of 1-(tert-butyl)-4-(3-(trifluoromethyl)benzoyl)-1H-pyrazole-5-carboxylic acid and 1 ml of N,N-dimethylformamide, 165 mg of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate was added and stirred at room temperature for 15 minutes. 37 mg of diisopropylethylamine was added to the reaction mixture, and the mixture was stirred at room temperature for 1 day. After completion of the reaction, 10 ml of water was added at room temperature, and the mixture was extracted with ethyl acetate. The obtained organic layer was dehydrated and dried over 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 (gradient from 95:5 to 55:45) as an eluent to give 67 mg of the desired product as a solid, melting point: 84-86°C.

[0464] Synthesis Example 13: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-((3,5-dichloropyridin-2-yl)methoxy)-1H-pyrazole-5-carboxamide (Compound No. 21-087) To a mixed solution of 160.9 mg of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-hydroxy-1H-pyrazole-5-carboxamide synthesized in Reference Example 1 described below and 0.25 ml of N,N-dimethylformamide, 74.9 mg of sodium iodide and 129.2 mg of diisopropylethylamine were added. The reaction mixture was ice-cooled to 0°C, and then 98.2 mg of 3,5-dichloro-2-(chloromethyl)pyridine was added. The mixture was warmed to room temperature and stirred for 6 hours. After completion of the reaction, water was added at room temperature, and the mixture was extracted with ethyl acetate. The resulting organic layer was dehydrated and dried over diatomaceous earth, 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 (gradient from 100:0 to 40:60) as an eluent to obtain 49 mg of the target product as an oil. 1 H-NMR (CDCl3, Me4Si, 300MHz) δ10.44 (s, 1H), 8.28 (s, 1H), 7.74-7.51 (m, 5H), 7.45-7.35 (m, 1H), 5.29 (s, 2H), 1.73 (s, 9H).

[0465] Synthesis Example 14: Synthesis of 1-(tert-butyl)-4-(3-cyclopropylbenzoyl)-N-((2,4-dichlorobenzyl)oxy)-1H-pyrazole-5-carboxamide (Compound No. 21-032) To a mixed solution of 200 mg of 4-(3-bromobenzoyl)-1-(tert-butyl)-N-((2,4-dichlorobenzyl)oxy)-1H-pyrazole-5-carboxamide, 49 mg of cyclopropylboronic acid, 243 mg of tripotassium phosphate, 16 mg of [1,1′-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride, and 3 ml of 1,4-dioxane, 1 ml of water was added, and the reaction mixture was stirred at 110° C. for 3 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature and stirred at room temperature for 1 day. To the reaction mixture, 73.5 mg of cyclopropylboronic acid, 364.5 mg of tripotassium phosphate, and 24 mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium(divalent) dichloride were added, and the mixture was stirred at 110°C for 3 hours. After completion of the reaction, water was added at room temperature, and the mixture was extracted with chloroform. The solvent was removed from the obtained organic layer under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 100:0 to 60:40) as an eluent, and 167 mg of the target product was obtained as an oil.

[0466] Reference Examples The following are reference examples of methods for producing intermediates for the compounds of the present invention.

[0467] Reference Example 1: Synthesis of 1-(tert-butyl)-4-(3-chlorobenzoyl)-N-hydroxy-1H-pyrazole-5-carboxamide (Compound No. ii-001) To a mixed solution of 9.6 g of 1-(tert-butyl)-4-(3-chlorobenzoyl)-1H-pyrazole-5-carboxylic acid, 150 g of dichloromethane, and 72 μL of N,N-dimethylformamide, 6.0 g of oxalyl chloride was added dropwise and stirred at room temperature for 2 hours. After completion of the reaction, 30 ml of toluene was added, and 160 g of the solvent was distilled off under reduced pressure. The reaction mixture was added to a mixed solution of 11.3 g of hydroxylamine hydrochloride, 33.2 g of sodium carbonate, 100 ml of water, and 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the mixture was extracted with ethyl acetate. To the resulting aqueous layer, 35% by mass hydrochloric acid was added under ice-cooling until the pH reached 1, and the mixture was extracted with dichloromethane. The resulting organic layer was washed with saturated brine, then dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. 60 ml of diisopropyl ether was added to the resulting residue, and the mixture was stirred at room temperature for 1 hour, after which the precipitated solid was collected by filtration. The resulting solid was washed with 10 ml of diisopropyl ether to obtain 7.7 g of the target product as a white solid. Melting point: 176-178°C.

[0468] Reference Example 2: Synthesis of O-(4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)benzyl)hydroxylamine hydrochloride Step 1: Synthesis of ethyl N-((4-cyanobenzyl)oxy)acetimidate To a mixed solution of 52.9 g of 4-(bromomethyl)benzonitrile, 31.5 g of ethyl N-hydroxyacetimidate, 180 ml of N-methyl-2-pyrrolidone, and 21.6 ml of water, 24.8 ml of 48% by mass aqueous sodium hydroxide solution was added dropwise at 0°C, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, 200 ml of water was added at room temperature, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate = 1:1 (volume ratio) (100 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 57.8 g of the target product as a yellow solid. Melting point: 59-61°C.

[0469] Step 2: Synthesis of ethyl N-((4-(N'-hydroxycarbamimidoyl)benzyl)oxy)acetimidate To a mixed solution of 57.8 g of ethyl N-((4-cyanobenzyl)oxy)acetimidate and 265 ml of methanol, 17.5 ml of a 50% by mass aqueous hydroxylamine solution was added at room temperature, and the mixture was stirred at 40°C for 24 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. To the resulting residue, 250 ml of water was added, and the mixture was extracted with ethyl acetate (150 ml x 3 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 64 g of the target product as a white solid. Melting point: 69-71°C.

[0470] Step 3: Synthesis of ethyl N-((4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)benzyl)oxy)acetimidate To a mixed solution of 10.5 g of ethyl N-((4-cyanobenzyl)oxy)acetimidate and 30.8 ml of dichloromethane, 3.48 g of pyridine was added at 0°C. 4.6 g of cyclopropanecarbonyl chloride was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, 35% by mass hydrochloric acid was added at 0°C until the pH reached 7, and the mixture was extracted with chloroform (20 ml × 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To a mixed solution of the obtained residue and 40 ml of tetrahydrofuran, 2.08 g of 40% by mass tetrabutylammonium hydroxide was added at room temperature, and the mixture was stirred at room temperature for 1 day. To the reaction mixture was added 1.25 g of 40% by mass tetrabutylammonium hydroxide at room temperature, and the mixture was stirred at 50°C for 6 hours. After allowing the reaction mixture to cool to room temperature, water was added, and the mixture was extracted with a mixed solution of n-hexane:ethyl acetate = 1:3 (20 ml x 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To the obtained residue was added a mixed solution of n-hexane:diisopropyl ether = 1:4, and the mixture was stirred at room temperature for 2 hours. The mixed solution was filtered, and 5 g of the target product was obtained as a white solid. Melting point: 57-59°C.

[0471] Step 4: Synthesis of O-(4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)benzyl)hydroxylamine hydrochloride (Compound No. ii-001) To a mixed solution of 13.6 g of ethyl N-((4-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)benzyl)oxy)acetimidate and 56.5 ml of methanol was added 56.5 ml of a 4 mol / l solution of hydrogen chloride in 1,4-dioxane at room temperature, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was filtered to obtain 6.9 g of the target product as a white solid. Melting point: 211-213°C.

[0472] Reference Example 3: Synthesis of O-(1-(4-methoxyphenyl)ethyl)hydroxylamine hydrochloride Step 1: Synthesis of 2-(1-(4-methoxyphenyl)ethoxy)isoindoline-1,3-dione To a mixed solution of 5.5 g of 1-(4-methoxyphenyl)ethan-1-ol, 3.3 g of N-hydroxyphthalimide, 5.2 g of triphenylphosphine, and 60 ml of tetrahydrofuran, 9.1 ml of a 2.2 mol / l toluene solution of diethyl azodicarboxylate was added under ice-cooling, and the mixture was stirred at room temperature for 19 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The resulting residue was washed with 29 ml of ethanol, and 5.1 g of the target product was obtained as a white solid. 1 H-NMR (CDCl3, Me4Si, 400MHz) δ7.76-7.72 (m, 2H), 7.70-7.68 (m, 2H), 7.44-7.41 (m, 2H), 6.86-6.84 (m, 2H), 5.46 (q, J = 6.5 Hz, 1H), 3.78 (s, 3H), 1.71 (d, J = 6.6 Hz, 3H).

[0473] Step 2: Synthesis of O-(1-(4-methoxyphenyl)ethyl)hydroxylamine hydrochloride To a mixed solution of 1.5 g of 2-(1-(4-methoxyphenyl)ethoxy)isoindoline-1,3-dione and 10 ml of dichloromethane, 0.76 g of hydrazine monohydrate was added at room temperature, and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, the precipitated solid was filtered off, and the obtained filtrate was washed with 10 ml of water. The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. To a mixed solution of the obtained residue and 3 ml of diisopropyl ether, 2 ml of a 4 mol / l solution of hydrogen chloride in 1,4-dioxane was added under ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of stirring, the precipitated solid was filtered, and 800 mg of the target product was obtained as a white solid. Melting point: 118-120°C.

[0474] Reference Example 4: Synthesis of 2-((4-(5-ethyl-1,2,4-oxadiazol-3-yl)benzyl)oxy)isoindoline-1,3-dione Step 1: Synthesis of 3-(4-(bromomethyl)phenyl)-5-ethyl-1,2,4-oxadiazole To a mixed solution of 100 mg of (4-(5-ethyl-1,2,4-oxadiazol-3-yl)phenyl)methanol, 196 mg of carbon tetrabromide, and 2 ml of acetonitrile, 155 mg of triphenylphosphine was added under ice-cooling, and the mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure. 20 ml of diisopropyl ether was added to the obtained residue, and insoluble matter was filtered off. The solvent was distilled off from the obtained organic layer under reduced pressure. The obtained residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 90:10 to 10:90) as an eluent, to obtain 60 mg of the target product as a white solid. Melting point: 71-73°C.

[0475] Step 2: Synthesis of 2-((4-(5-ethyl-1,2,4-oxadiazol-3-yl)benzyl)oxy)isoindoline-1,3-dione To a mixed solution of 60 mg of 3-(4-(bromomethyl)phenyl)-5-ethyl-1,2,4-oxadiazole, 36 mg of N-hydroxyphthalimide, and 3 ml of N,N-dimethylformamide, 37 mg of 1,8-diazabicyclo[5.4.0]-7-undecene was added at room temperature, and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 9 ml of water was added to the reaction mixture, and the precipitated solid was collected by filtration and dried under reduced pressure to obtain 70 mg of the target product as a white solid. Melting point: 172-174°C.

[0476] The compounds of the present invention and their intermediates can be synthesized in accordance with the above-mentioned Synthesis Examples and Reference Examples, or according to the above-mentioned reaction schemes. Examples of the compounds of the present invention produced in the same manner as in Synthesis Examples 1 to 14 are shown in Tables 1 to 29, examples of intermediates produced in the same manner as in Steps 1 to 4 of Synthesis Example 1 are shown in Table 30, examples of intermediates produced in the same manner as in Reference Example 1 are shown in Table 31, and examples of intermediates produced according to Reaction Schemes 11 to 13 or 17 to 19 are shown in Tables 32 to 35, but the compounds of the present invention and their intermediates are not limited to these.

[0477] In the tables, the substituent marked "Me" represents "methyl," and similarly hereinafter, "Et" represents "ethyl," "nPr" represents "normal propyl," "nBu" represents "normal butyl," "tBu" represents "tertiary butyl," "iPr" represents "isopropyl," "cPr" represents "cyclopropyl," "cHx" represents "cyclohexyl," "Ph" represents "phenyl," and "Bn" represents "benzyl." The notation "*" indicates that the compound is an oily or resinous compound with no melting point, and "m.p." represents the melting point (unit: °C).

[0478] 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.

[0479] Also, G-2a, G-3a, G-4a, G-5a, G-6a, G-7a, G-8a, G-9a, G-10a, G-11a, E-2a, E-3a, E-4a, E-5a, E- 13a, E-14a, E-18a, E-20a, E-21a, E-22a, E-23a, E-28a, E-29a, E-30a, E-40a, E-41a, E-42a, E- 43a, E-44a, E-45a, E-48a, E-58a, E-62a, E-63a, Z-2a, Z-3a, Z-4a, Z-6a, Z-8a, Z-9a, Z-10a, Z -11a, Z-18a, Z-23a, Z-25a, Z-26a, Z-27a, Z-28a, Z-30a, Z-33a, Z-34a, Z-41a, Z-42a, Z-49a, R Ｘ -2a, R Ｘ -3a, R Ｘ -4a, R Ｘ The substituents represented by J-5a, J-1a, J-2a and J-3a each have the following structure.

[0480] In the above diagram, the numbers written in the structural formula indicate the substitution position, and for example, the description "6-OMe-(E-3a)" in the table represents the following structure. The absence of a substituent indicates that the compound is unsubstituted.

[0481] For example, the description "3-(E-2a)-(Z-41a)" in the table represents the following structure: In addition, those without a description of a substituent in the table represent that they are unsubstituted.

[0482] [Table 1] ―――――――――――――――――――――――――――――――― No. G Z R X R a R 2m.p.(℃) ―――――――――――――――――――――――――――――――――― 1-001 3-CF3-Ph 4-Me-Ph tBu Me H 137-139 1-002 3-Cl-Ph 4-Me-Ph tBu Me Me 57-59 1-003 3-Me-Ph 4-Me-Ph tBu Me Me 154-156 1-004 3-OMe-Ph 4-Me-Ph tBu Me Me 121-123 1-005 Ph 4-Me-Ph tBu Me Me 122-124 1-006 Ph 4-Me-Ph Ph Me Me 119-121 1-007 Ph 4-Me-Ph tBu Me H 169-171 1-008 3-Br-Ph 4-Me-Ph tBu Me Me 69-71 1-009 3-Cl-Ph 3-OH-Ph tBu H H 192-194 1-010 3-Cl-Ph 3-C≡N-Ph tBu H H * 1-011 3-Cl-Ph 4-OH-Ph tBu H H 211-213 1-012 3-Cl-Ph 4-C≡N-Ph tBu H H 120-122 1-013 3-Cl-Ph 3-C(O)OMe-Ph tBu H H 112-114 1-014 3-Cl-Ph 4-C(O)OMe-Ph tBu H H 160-162 1-015 3-Cl-Ph 3-(E-2a)-(Z-41a) tBu Me H * 1-016 3-Cl-Ph 3-(OCH2(5-Cl-(E-2a)))-Ph tBu H H * 1-017 3-Cl-Ph 4-(OCH2(5-Cl-(E-2a)))-Ph tBu H H 168-170 1-018 3-Cl-Ph 3-(3-Me-(E-41a))-Ph tBu H H 163-165 1-019 3-Cl-Ph 4-(3-Me-(E-41a))-Ph tBu H H *―――――――――――――――――――――――――――――――――――――――― [Table 2] ―――――――――――――――――――――――――――――――――――― No. G Z R X R 3 R 4m.p.(℃) ―――――――――――――――――――――――――――――――――― 2-001 3-CF3-Ph 2,4-Cl2-Ph tBu H H 127-129 2-002 3-CF3-Ph 2,4-Me2-Ph tBu H H 112-114 2-003 3-CF3-Ph 2,4-Me2-Ph tBu F F * 2-004 3-CF3-Ph 4-Me-Ph tBu H H 137-139 2-005 3-CF3-Ph 4-Cl-Ph tBu H H 167-169 2-006 3-CF3-Ph 2,4-Me2-Ph Ph H H * 2-007 3-CF3-Ph 2,4-Cl2-Ph Ph H H 132-134 2-008 3-CF3-Ph 4-Cl-Ph Ph OH H 132-134 2-009 3-CF3-Ph 4-Me-Ph Ph H H 146-148 2-010 3-CF3-Ph 4-Cl-Ph Ph H H 189-191 2-011 3-Cl-Ph 4-Me-Ph tBu H H 107-109 2-012 3-Cl-Ph 4-Cl-Ph tBu H H 137-139 2-013 3-Cl-Ph 4-OMe-Ph tBu H H * 2-014 3-Cl-Ph 2,4-Me2-Ph tBu H H 101-104 2-015 3-Cl-Ph 2,4-Cl2-Ph tBu H H 112-114 2-016 3-Me-Ph 4-Me-Ph tBu H H 121-123 2-017 3-Me-Ph 4-Cl-Ph tBu H H 152-154 2-018 3-Me-Ph 4-OMe-Ph tBu H H 91-93 2-019 3-Me-Ph 2,4-Me2-Ph tBu H H 116-118 2-020 3-Me-Ph 2,4-Cl2-Ph tBu H H 111-113 2-021 3-OMe-Ph 4-Me-Ph tBu H H 102-104 2-022 3-OMe-Ph 4-Cl-Ph tBu H H 146-148 2-023 3-OMe-Ph 4-OMe-Ph tBu H H 89-91 2-024 3-OMe-Ph 2,4-Me2-Ph tBu H H 71-73 2-025 3-OMe-Ph 2,4-Cl2-Ph tBu H H 99-101 2-026 Ph 2,4-Me2-Ph tBu H H 124-126 2-027 Ph 2,4-Me2-Ph tBu F F 74-76 2-028 Ph 2,4-Me2-Ph Ph H H * 2-029 Ph 2,4-Me2-Ph Ph F F 124-126 2-030 Ph 4-Me-Ph tBu H H 136-138 2-031 Ph 4-Cl-Ph tBu H H 144-146 2-032 Ph 4-Me-Ph Ph H H 119-121 2-033 Ph 4-Cl-Ph Ph H H 146-149 2-034 Ph 2,4-Cl2-Ph Ph H H 114-116 2-035 Ph 4-Cl-Ph Ph OH H 122-124 2-036 3-CF3-Ph 2,4-Me2-Ph iPr H H * 2-037 3-CF3-Ph 2,4-Me2-Ph cHx H H * 2-038 3-CF3-Ph 2,4-Me2-Ph Bn H H * 2-039 3-CF3-Ph 4-Cl-Ph tBu OH H * 2-040 Ph 4-Cl-Ph tBu OH H 147-149 2-041 3-Cl-Ph 4-Cl-Ph tBu OH H * 2-042 4-Cl-Ph 4-Me-Ph tBu H H 115-117 2-043 4-Cl-Ph 4-Cl-Ph tBu H H 142-144 2-044 4-Cl-Ph 2,4-Cl2-Ph tBu H H 152-154 2-045 3,4-Cl2-Ph 4-Me-Ph tBu H H 161-163 2-046 3,4-Cl2-Ph 4-Cl-Ph tBu H H 154-156 2-047 3,4-Cl2-Ph 2,4-Cl2-Ph tBu H H 147-149 2-048 2,3-Cl2-Ph 4-Me-Ph tBu H H 151-153 2-049 2,3-Cl2-Ph 4-Cl-Ph tBu H H 159-161 2-050 2,3-Cl2-Ph 2,4-Cl2-Ph tBu H H 139-141 2-051 2,4-Cl2-Ph 4-Me-Ph tBu H H 149-151 2-052 2,4-Cl2-Ph 4-Cl-Ph tBu H H 146-148 2-053 2,4-Cl2-Ph 2,4-Cl2-Ph tBu H H 142-144 2-054 2-Cl-Ph 4-Me-Ph tBu H H 147-149 2-055 2-Cl-Ph 4-Cl-Ph tBu H H 182-184 2-056 2-Cl-Ph 2,4-Cl2-Ph tBu H H 154-156 2-057 3-Cl-Ph 4-Me-Ph iPr H H 84-86 2-058 3-Cl-Ph 4-Cl-Ph iPr H H 104-106 2-059 3-Cl-Ph 2,4-Cl2-Ph iPr H H * 2-060 3-Cl-Ph 4-Me-Ph R, X -2a H H 119-121 2-061 3-Cl-Ph 4-Cl-Ph R X -2a H H 137-139 2-062 3-Cl-Ph 2,4-Cl2-Ph R X -2a H H 124-126 2-063 3-Cl-Ph 4-Me-Ph R X -3a H H 114-116 2-064 3-Cl-Ph 4-Cl-Ph R X -3a H H 139-141 2-065 3-Cl-Ph 2,4-Cl2-Ph R X -3a H H 130-132 2-066 3-Cl-Ph 4-Me-Ph R X -4a H H 139-141 2-067 3-Cl-Ph 4-Cl-Ph R X -4a H H 154-156 2-068 3-Cl-Ph 2,4-Cl2-Ph R X-4a H H 149-151 2-069 6-CF3-(G-2a) 2,4-Cl2-Ph tBu H H 182-184 2-070 6-Br-(G-2a) 2,4-Cl2-Ph tBu H H 172-174 2-071 5-CF3-(G-3a) 2,4-Cl2-Ph tBu H H 161-163 2-072 6-CF3-(G-2a) 4-Cl-Ph tBu H H 124-126 2-073 6-CF3-(G-2a) 4-Me-Ph tBu H H 156-158 2-074 6-Br-(G-2a) 4-Cl-Ph tBu H H 202-204 2-075 6-Br-(G-2a) 4-Me-Ph tBu H H 177-179 2-076 5-CF3-(G-3a) 4-Cl-Ph tBu H H 159-161 2-077 5-CF3-(G-3a) 4-Me-Ph tBu H H 151-153 2-078 3-Cl-Ph 4-F-Ph tBu H H 149-151 2-079 3-Cl-Ph 3-Me-Ph tBu H H 139-141 2-080 3-Cl-Ph 2-Me-Ph tBu H H 149-151 2-081 3-Cl-Ph 4-Et-Ph tBu H H 109-111 2-082 3-Cl-Ph 3-OMe-Ph tBu H H 97-99 2-083 3-Cl-Ph 2-OMe-Ph tBu H H 119-121 2-084 3-Cl-Ph 4-OEt-Ph tBu H H * 2-085 3-Cl-Ph 3-Cl-Ph tBu H H 129-131 2-086 3-Cl-Ph 2-Cl-Ph tBu H H 146-148 2-087 3-Cl-Ph 3,4-Cl2-Ph tBu H H 162-164 2-088 3-Cl-Ph 2,6-Cl2-Ph tBu H H 156-158 2-089 3-Cl-Ph 4-C≡N-Ph tBu H H 159-161 2-090 3-Br-Ph 4-Me-Ph tBu H H * 2-091 3-Br-Ph 4-Cl-Ph tBu H H 151-152 2-092 3-Br-Ph 4-OMe-Ph tBu H H * 2-093 3-Cl-Ph 3,4-(OMe)2-Ph tBu H H 137-139 2-094 3-Cl-Ph 4-CF3-Ph tBu H H 186-188 2-095 3-Cl-Ph 3,4-Me2-Ph tBu H H 129-131 2-096 3-Cl-Ph Z-4a tBu H H 107-109 2-097 3-Cl-Ph 4-Br-Ph tBu H H 134-136 2-098 3-Cl-Ph 3-Cl-4-OMe-Ph tBu H H 91-93 2-099 3-Cl-Ph 2-Me-4-Br-Ph tBu H H 123-125 2-100 3-Cl-Ph 2-Cl-4-Me-Ph tBu H H * 2-101 3-Cl-Ph 2,4,6-Me3-Ph tBu H H 149-151 2-102 3-Cl-Ph 2-F-4-Me-Ph tBu H H 109-111 2-103 3-Cl-Ph 2-F-4-Cl-Ph tBu H H 119-121 2-104 3-Cl-Ph 2-Br-4-Cl-Ph tBu H H 123-125 2-105 3-Cl-Ph 5-Me-(Z-11a) tBu H H 106-108 2-106 3-Br-Ph 2,4-Me2-Ph tBu H H 124-125 2-107 3-Br-Ph 2,4-Cl2-Ph tBu H H * 2-108 2-F-5-Cl-Ph 4-Me-Ph tBu H H 154-156 2-109 3-Cl-Ph 2-Cl-4-Br-Ph tBu H H 100-103 2-110 3-Cl-Ph 2-Cl-4-OMe-Ph tBu H H * 2-111 3-Cl-Ph 2-Cl-3,4-(OMe)2-Ph tBu H H * 2-112 3-Cl-Ph 2-Me-4-OMe-Ph tBu H H * 2-113 3-Cl-Ph 2-F-4-Br-Ph tBu H H 116-118 2-114 3-Cl-Ph 2-F-4-OMe-Ph tBu H H 87-89 2-115 3-Cl-Ph 2-Br-4-Me-Ph tBu H H * 2-116 3-Cl-Ph 2-OMe-4-F-Ph tBu H H * 2-117 3-Cl-Ph 2-Me-4-F-Ph tBu H H 141-143 2-118 3-Cl-Ph 2-Br-4-F-Ph tBu H H 109-111 2-119 3-Cl-Ph Z-3a tBu H H 131-133 2-120 3-I-Ph 2,4-Cl2-Ph tBu H H 131-133 2-121 4-CF3-Ph 4-Me-Ph tBu H H * 2-122 2-Me-Ph 4-Me-Ph tBu H H 162-164 2-123 4-Me-Ph 4-Me-Ph tBu H H 121-123 2-124 2-F-Ph 4-Me-Ph tBu H H 136-138 2-125 3-F-Ph 4-Me-Ph tBu H H * 2-126 G-5a 4-Me-Ph tBu H H 148-150 2-127 G-6a 4-Me-Ph tBu H H * 2-128 G-7a 4-Me-Ph tBu H H * 2-129 4-F-Ph 4-Me-Ph tBu H H 118-120 2-130 3-F-Ph 2,4-Cl2-Ph tBu H H * 2-131 3-OEt-Ph 2,4-Cl2-Ph tBu H H 107-109 2-132 3-OnPr-Ph 2,4-Cl2-Ph tBu H H 109-111 2-133 3-OiPr-Ph 2,4-Cl2-Ph tBu H H 94-96 2-134 3-OCH2CH2OMe-Ph 2,4-Cl2-Ph tBu H H 96-98 2-135 3-OCH2CF3-Ph 2,4-Cl2-Ph tBu H H 109-111 2-136 3-OCH2CH=CH2-Ph 2,4-Cl2-Ph tBu H H 96-98 2-137 3-OCH2C≡CH-Ph 2,4-Cl2-Ph tBu H H * 2-138 3-OCH2C≡N-Ph 2,4-Cl2-Ph tBu H H 81-83 2-139 3-OCH(Me)C≡N-Ph 2,4-Cl2-Ph tBu H H * 2-140 3-SMe-Ph 2,4-Cl2-Ph tBu H H 94-96 2-141 3-SEt-Ph 2,4-Cl2-Ph tBu H H 94-96 2-142 3-S(iPr)-Ph 2,4-Cl2-Ph tBu H H * 2-143 3-Et-Ph 2,4-Cl2-Ph tBu H H * 2-144 3-cPr-Ph 2,4-Cl2-Ph tBu H H * 2-145 3-CH=CH2-Ph 2,4-Cl2-Ph tBu H H * 2-146 3-Cl-Ph 4-OnPr-Ph tBu H H * 2-147 3-Cl-Ph 4-OiPr-Ph tBu H H 137-139 2-148 3-Cl-Ph 4-OCH2CH2OMe-Ph tBu H H 101-103 2-149 3-Cl-Ph 4-OCH2CF3-Ph tBu H H 111-113 2-150 3-Cl-Ph 4-OCH2CH=CH2-Ph tBu H H 84-86 2-151 3-Cl-Ph 4-OCH2C≡CH-Ph tBu H H * 2-152 3-Cl-Ph 4-OCH2C≡N-Ph tBu H H * 2-153 3-SO2Me-Ph 2,4-Cl2-Ph tBu H H * 2-154 3-S(O)Me-Ph 2,4-Cl2-Ph tBu H H * 2-155 3-SO2iPr-Ph 2,4-Cl2-Ph tBu H H * 2-156 3-S(O)iPr-Ph 2,4-Cl2-Ph tBu H H * 2-157 3-SO2Et-Ph 2,4-Cl2-Ph tBu H H * 2-158 3-S(O)Et-Ph 2,4-Cl2-Ph tBu H H * 2-159 3-nPr-Ph 2,4-Cl2-Ph tBu H H * 2-160 2-F-Ph 2,4-Cl2-Ph tBu H H * 2-161 4-C≡N-Ph 2,4-Cl2-Ph tBu H H 75-77 2-162 2-OMe-Ph 2,4-Cl2-Ph tBu H H * 2-163 3-C≡N-Ph 2,4-Cl2-Ph tBu H H * 2-164 6-Cl-(G-2a) 4-Me-Ph tBu H H 164-166 2-165 6-Cl-(G-2a) 4-Cl-Ph tBu H H 194-196 2-166 6-Cl-(G-2a) 2,4-Cl2-Ph tBu H H 152-154 2-167 2-Cl-(G-4a) 4-Me-Ph tBu H H 149-151 2-168 2-Cl-(G-4a) 4-Cl-Ph tBu H H 166-168 2-169 2-Cl-(G-4a) 2,4-Cl2-Ph tBu H H 164-166 2-170 5-Cl-(G-3a) 4-Me-Ph tBu H H 142-144 2-171 5-Cl-(G-3a) 4-Cl-Ph tBu H H 172-174 2-172 5-Cl-(G-3a) 2,4-Cl2-Ph tBu H H 186-188 2-173 4-Cl-(G-2a) 4-Me-Ph tBu H H 2-174 4-Cl-(G-2a) 4-Cl-Ph tBu H H 2-175 4-Cl-(G-2a) 2,4-Cl2-Ph tBu H H 2-176 2-Br-Ph 4-Me-Ph tBu H H 151-153 2-177 2-Br-Ph 4-Cl-Ph tBu H H 177-179 2-178 2-Br-Ph 2,4-Cl2-Ph tBu H H 144-146 2-179 2-OH-Ph 4-Me-Ph tBu H H 186-188 2-180 2-OH-Ph 4-Cl-Ph tBu H H 159-161 2-181 2-OH-Ph 2,4-Cl2-Ph tBu H H 159-161 2-182 2-Cl-(G-3a) 4-Me-Ph tBu H H 2-183 2-Cl-(G-3a) 4-Cl-Ph tBu H H 2-184 2-Cl-(G-3a) 2,4-Cl2-Ph tBu H H 2-185 2-Cl-(G-8a) 4-Me-Ph tBu H H 2-186 2-Cl-(G-8a) 4-Cl-Ph tBu H H 2-187 2-Cl-(G-8a) 2,4-Cl2-Ph tBu H H ―――――――――――――――――――――――――――――――――― [Table 3], ―――――――――――――――――――――――――――――――――― No. G Z 1 R X R 3 R 4 m.p.(℃) ―――――――――――――――――――――――――――――――――― 3-001 3-Cl-Ph OCH2(2-F-Ph) tBu H H 86-88 3-002 3-Cl-Ph OCH2(6-Me-(E-2a)) tBu H H * 3-003 3-Cl-Ph OCH2(3-Me-Ph) tBu H H * ―――――――――――――――――――――――――――――――――― [Table 4], ―――――――――――――――――――――――――――――――――― No. G Z R Xm.p.(℃) ―――――――――――――――――――――――――――――――――― 4-001 3-Cl-Ph 3-Cl-5-Br-(Z-8a) tBu 177-179 4-002 3-Cl-Ph 4-Cl-Ph tBu 137-139 4-003 3-Cl-Ph 4-Br-Ph tBu 139-141 4-004 3-Cl-Ph 2,4-Cl2-Ph tBu * 4-005 3-Cl-Ph 4-OMe-Ph tBu * 4-006 3-Cl-Ph 2-OMe-Ph tBu 111-113 4-007 3-Cl-Ph 3,4-(OMe)2-Ph tBu * 4-008 3-Cl-Ph 3,5-Cl2-(Z-8a) tBu * 4-009 3-Cl-Ph 3-Br-5-Me-(Z-8a) tBu 167-168 4-010 3-Cl-Ph 3-Me-5-Br-(Z-8a) tBu 181-183 4-011 3-F-Ph 4-Br-Ph tBu 134-136 4-012 3-Cl-Ph 4-(3-Me-(E-41a))-Ph tBu * 4-013 3-Cl-Ph 4-(3-Et-(E-41a))-Ph tBu * 4-014 3-Cl-Ph 4-(3-cPr-(E-41a))-Ph tBu * 4-015 3-Cl-Ph 4-(5-Et-(E-40a))-Ph tBu 134-136 4-016 3-Cl-Ph 4-(5-CF2H-(E-40a))-Ph tBu 132-134 4-017 3-Cl-Ph 4-(5-iPr-(E-40a))-Ph tBu * 4-018 3-Cl-Ph 4-(5-cPr-(E-40a))-Ph tBu * 4-019 3-Cl-Ph 4-(5-CH(OMe)Me-(E-40a))-Ph tBu * 4-020 3-CF3-Ph 4-(3-Et-(E-41a))-Ph tBu * 4-021 3-CF3-Ph 4-(3-cPr-(E-41a))-Ph tBu * 4-022 3-Cl-Ph 4-(3-NMe2-(E-41a))-Ph tBu * 4-023 Ph 4-(3-cPr-(E-41a))-Ph tBu 134-136 4-024 Ph 4-C(O)OMe-Ph tBu 117-118 4-025 3-Cl-Ph 4-C≡N-Ph tBu * ―――――――――――――――――――――――――――――――――― [Table 5], ―――――――――――――――――――――――――――――――――― No. G Z R Xm.p.(℃) ―――――――――――――――――――――――――――――――――― 5-001 3-Cl-Ph 4-Me-Ph CH(Me)iPr * 5-002 3-Cl-Ph 4-Cl-Ph CH(Me)iPr 74-76 5-003 3-Cl-Ph 2,4-Cl2-Ph CH(Me)iPr * 5-004 3-Cl-Ph 4-Me-Ph CH(Me)tBu * 5-005 3-Cl-Ph 4-Cl-Ph CH(Me)tBu * 5-006 3-Cl-Ph 2,4-Cl2-Ph CH(Me)tBu * 5-007 3-Cl-Ph 4-Me-Ph CH(Me)CH2iPr 59-61 5-008 3-Cl-Ph 4-Cl-Ph CH(Me)CH2iPr * 5-009 3-Cl-Ph 2,4-Cl2-Ph CH(Me)CH2iPr * 5-010 3-Cl-Ph 4-Me-Ph 3-F-5-Cl-(R X -2a) * 5-011 3-Cl-Ph 4-Cl-Ph 3-F-5-Cl-(R X -2a) * 5-012 3-Cl-Ph 2,4-Cl2-Ph 3-F-5-Cl-(R X -2a) * 5-013 3-Cl-Ph 4-Me-Ph 3-Cl-5-CF3-(R X -2a) * 5-014 3-Cl-Ph 4-Cl-Ph 3-Cl-5-CF3-(R X -2a) * 5-015 3-Cl-Ph 2,4-Cl2-Ph 3-Cl-5-CF3-(R X-2a) * 5-016 3-Cl-Ph 4-Me-Ph 2-F-4-C≡N-Ph * 5-017 3-Cl-Ph 4-Cl-Ph 2-F-4-C≡N-Ph * 5-018 3-Cl-Ph 2,4-Cl2-Ph 2-F-4-C≡N-Ph * 5-019 3-Cl-Ph 4-Me-Ph 2,4-Cl2-Ph * 5-020 3-Cl-Ph 4-Cl-Ph 2,4-Cl2-Ph * 5-021 3-Cl-Ph 2,4-Cl2-Ph 2,4-Cl2-Ph * 5-022 3-Cl-Ph 4-Me-Ph 6-Cl-(R X -5a) * 5-023 3-Cl-Ph 4-Cl-Ph 6-Cl-(R X -5a) * 5-024 3-Cl-Ph 2,4-Cl2-Ph 6-Cl-(R X -5a) * 5-025 3-Cl-Ph 2,4-Cl2-Ph CH(Me)CH(Me)2 * 5-026 3-Cl-Ph 4-Cl-Ph CH(Me)CH2CH(Me)2 * 5-027 3-Cl-Ph 6-OMe-(Z-9a) tBu * 5-028 3-Me-Ph 4-C(O)OMe-Ph tBu 119 - 121 ―――――――――――――――――――――――――――――――――― [Table 6] ―――――――――――――――――――――――――――――――――― No. G Z R X m.p.(°C) ―――――――――――――――――――――――――――――――――― 6-001 3-Cl-Ph 4-Cl-Ph tBu 134 - 136 ―――――――――――――――――――――――――――――――――― [Table 7] ―――――――――――――――――――――――――――――――――― No. G Z R 3 R4m.p.(℃) ―――――――――――――――――――――――――――――――――― 7-001 3-Cl-Ph 4-Me-Ph Me H * 7-002 3-Cl-Ph 4-Me-Ph F H * 7-003 3-Cl-Ph 4-Me-Ph OH Me * 7-004 3-Cl-Ph 4-Cl-Ph OH Me * 7-005 3-Cl-Ph 2,4-Cl2-Ph OH Me 104-106 7-006 3-Cl-Ph 2,4-Me2-Ph OH Me 104-106 7-007 3-Cl-Ph 4-Me-Ph Me Me * 7-008 3-Cl-Ph 4-OH-Ph Me H 150-152 7-009 3-Cl-Ph 2,4-Me2-Ph OH H * 7-010 3-Cl-Ph 4-OH-Ph OH H * 7-011 3-Cl-Ph 2,4-Cl2-Ph OH H * 7-012 3-Cl-Ph 4-Br-Ph OH Me * 7-013 3-Cl-Ph 4-OMe-Ph OH Me * 7-014 3-Cl-Ph 2,4-Cl2-Ph Me H * 7-015 3-Cl-Ph 2,4-Cl2-Ph Me Me * 7-016 3-Cl-Ph 2,4-Cl2-Ph Et H * 7-017 3-Cl-Ph 2,4-Cl2-Ph Et Me * 7-018 3-Cl-Ph 2,4-Cl2-Ph Et Et * 7-019 3-Cl-Ph 3,5-Cl2-(Z-8a) Me H * 7-020 3-Cl-Ph 3-Cl-5-Br-(Z-8a) Me H * 7-021 3-Cl-Ph 5-Br-(Z-8a) Me H * 7-022 3-F-Ph 2,4-Me2-Ph F F 69-71 7-023 3-Br-Ph 2,4 - Di - Me - Ph F F * 7 - 024 3 - Me - Ph 2,4 - Di - Me - Ph F F * 7 - 025 2 - Cl - Ph 2,4 - Di - Me - Ph F F 141 - 143 7 - 026 3 - Cl - Ph 3,5 - Di - Me -(Z - 8a) Me Me * 7 - 027 3 - Cl - Ph 3 - Cl - 5 - Br -(Z - 8a) Me Me * 7 - 028 3 - Cl - Ph 2,4 - Di - Me - Ph F F * 7 - 029 3 - Cl - Ph 2 - Cl - 4 - OMe - Ph OH H * 7 - 030 3 - Cl - Ph 4-(5 - Et -(E - 40a))-Ph OH Me * 7 - 031 3 - Cl - Ph 4 - C≡N - Ph OH Me * ―――――――――――――――――――――――――――――――――― [Table 8], ―――――――――――――――――――――――――――――――――― No. G Z R a m.p.(°C) ―――――――――――――――――――――――――――――――――― 8 - 001 3 - Cl - Ph 2,4 - Di - Me - Ph CH2OMe 148 - 150 ―――――――――――――――――――――――――――――――――― [Table 9], ―――――――――――――――――――――――――――――――――― No. G Z m.p.(℃) ―――――――――――――――――――――――――――――――――― 9-001 3-(OCH2(3-CF3-Ph))-Ph 2,4-Cl2-Ph 91-93 9-002 3,5-F2-Ph 2,4-Cl2-Ph 114-116 9-003 G-9a 2,4-Cl2-Ph * 9-004 3-OCF3-Ph 2,4-Cl2-Ph 133-135 9-005 2-CF3-Ph 2,4-Cl2-Ph * 9-006 Ph 2,4-Cl2-Ph 110-112 9-007 5-Cl-(G-3a) 2,4-Cl2-Ph 186-188 9-008 2-OH-Ph 2,4-Cl2-Ph 159-161 9-009 5-Cl-(G-6a) 2,4-Cl2-Ph * 9-010 1-Me-(G-10a) 2,4-Cl2-Ph * 9-011 1-Me-(G-11a) 2,4-Cl2-Ph * 9-012 3,5-Cl2-Ph 2,4-Cl2-Ph * 9-013 2,3-F2-Ph 2,4-Cl2-Ph * 9-014 2-F-3-Cl-Ph 2,4-Cl2-Ph * 9-015 3-Cl-Ph 2,4-(OMe)2-Ph * 9-016 3-F-Ph 2,4-Me2-Ph * 9-017 3-Cl-Ph 2-Br-Ph * 9-018 3-Cl-Ph 2,4-F2-Ph * 9-019 3-Cl-Ph 2-Br-4-OMe-Ph * 9-0202-Cl-(G-4a) 2,4-Cl2-Ph 164-166 9-021 3-Cl-Ph 2-OMe-4-Me-Ph 115-117 9-022 Ph 2-F-4-OMe-Ph 114-116 9-023 3-F-Ph 2-F-4-OMe-Ph * 9-024 3-Br-Ph 2-F-4-OMe-Ph * 9-025 3-Me-Ph 2-F-4-OMe-Ph * 9-026 3-CF3-Ph 2-F-4-OMe-Ph * 9-027 2-Cl-Ph 2-F-4-OMe-Ph * 9-028 Ph 2-Me-4-OEt-Ph * 9-029 3-Me-Ph 2-Me-4-OEt-Ph * 9-030 3-Cl-Ph 2-Me-4-OEt-Ph * 9-031 Ph 2-OMe-4-Me-Ph 149-151 9-032 3-Me-Ph 2-OMe-4-Me-Ph * 9-033 3-F-Ph 2-OMe-4-Me-Ph * 9-034 Ph 2-Cl-4-Me-Ph * 9-035 3-F-Ph 2-Cl-4-Me-Ph * 9-036 3-Br-Ph 2-Cl-4-Me-Ph 129-131 9-037 3-Me-Ph 2-Cl-4-Me-Ph 129-131 9-038 3-CF3-Ph 2-Cl-4-Me-Ph * 9-039 Ph 2-F-4-Br-Ph 107-109 9-040 3-F-Ph 2-F-4-Br-Ph 79-81 9-041 3-Me-Ph 2-F-4-Br-Ph 102-104 9-042Ph 2-Me-4-OMe-Ph * 9-043 3-F-Ph 2-Me-4-OMe-Ph * 9-044 3-Me-Ph 2-Me-4-OMe-Ph * 9-045 Ph 2-F-4-Me-Ph 144-146 9-046 3-F-Ph 2-F-4-Me-Ph * 9-047 3-Me-Ph 2-F-4-Me-Ph 124-126 9-048 Ph 3,4-Me2-Ph 146-148 9-049 3-F-Ph 3,4-Me2-Ph * 9-050 3-Me-Ph 3,4-Me2-Ph 154-156 9-051 3-Br-Ph 2-OMe-4-Me-Ph * 9-052 3-CF3-Ph 2-OMe-4-Me-Ph 128-130 9-053 2-Cl-Ph 2-OMe-4-Me-Ph * 9-054 Ph 2-Cl-4-OEt-Ph * 9-055 3-Me-Ph 2-Cl-4-OEt-Ph * 9-056 3-Cl-Ph 2-Cl-4-OEt-Ph * 9-057 6-Cl-(G-2a) 2,4-Cl2-Ph 152-154 9-058 Ph 2-Br-4-Me-Ph 99-101 9-059 3-Me-Ph 2-Br-4-Me-Ph 104-106 9-060 3-F-Ph 2-Br-4-Me-Ph * 9-061 Ph 2-Me-4-Br-Ph 122-124 9-062 3-Me-Ph 2-Me-4-Br-Ph 86-88 9-063 3-F-Ph 2-Me-4-Br-Ph * 9-064 Ph2,4-Br2-Ph 152-154 9-065 3-Cl-Ph 2,4-Br2-Ph 132-134 9-066 Ph 2-Br-4-OMe-Ph * 9-067 3-Me-Ph 2-Br-4-OMe-Ph * 9-068 3-F-Ph 2-Br-4-OMe-Ph * 9-069 3-Br-Ph 2-Br-4-OMe-Ph * 9-070 3-CF3-Ph 2-Br-4-OMe-Ph * 9-071 3-Cl-Ph 2-OMe-4-Cl-Ph * 9-072 3-Cl-Ph 2-OMe-4-Br-Ph 139-141 9-073 3-F-Ph 2-Cl-4-Br-Ph 121-123 9-074 3-F-Ph 2-F-4-Cl-Ph 89-91 9-075 3-F-Ph 2-Cl-4-OMe-Ph * 9-076 Ph 2-Br-4-Cl-Ph 140-142 9-077 3-F-Ph 2-Br-4-Cl-Ph 149-151 9-078 3-Br-Ph 2-Br-4-Cl-Ph * 9-079 3-Me-Ph 2-Br-4-Cl-Ph * 9-080 3-CF3-Ph 2-Br-4-Cl-Ph 142-144 9-081 2-Cl-Ph 2-Br-4-Cl-Ph * 9-082 3-Cl-Ph 3,5-Cl2-(Z-8a) * 9-083 3-Cl-Ph 3-Br-5-Me-(Z-8a) 131-133 9-084 3-Cl-Ph 3-Me-5-Br-(Z-8a) * 9-085 3-CF3-Ph 2-Me-4-OMe-Ph 142-144 9-0863-CF3-Ph 2,4-F2-Ph * 9-087 3-CF3-Ph 2,4-Br2-Ph 136-138 9-088 3-Cl-Ph 2-Ph-(Z-33a) * 9-089 3-F-Ph 2-Ph-(Z-33a) * 9-090 Ph 2-Ph-(Z-33a) * 9-091 3-CF3-Ph 2-Ph-(Z-33a) * 9-092 3-Cl-Ph 1-Ph-(Z-26a) * 9-093 3-F-Ph 1-Ph-(Z-26a) * 9-094 Ph 1-Ph-(Z-26a) * 9-095 3-CF3-Ph 1-Ph-(Z-26a) * 9-096 3-Cl-Ph 3-Ph-(Z-25a) 146-147 9-097 3-F-Ph 3-Ph-(Z-25a) 148-149 9-098 Ph 3-Ph-(Z-25a) 156-157 9-099 3-CF3-Ph 3-Ph-(Z-25a) 111-112 9-100 3-Cl-Ph 2-Ph-(Z-34a) * 9-101 3-F-Ph 2-Ph-(Z-34a) 156-157 9-102 Ph 2-Ph-(Z-34a) 157-158 9-103 3-CF3-Ph 2-Ph-(Z-34a) * ―――――――――――――――――――――――――――――――――― [Table 10] ―――――――――――――――――――――――――――――――――― No. G Z 1m.p.(℃) ―――――――――――――――――――――――――――――――――― 10-001 3-Cl-Ph OH * 10-002 3-Cl-Ph NO2 166-168 10-003 3-Cl-Ph OCH2(6-Cl-(E-3a)) * 10-004 3-Cl-Ph OCH2(2-Cl-(E-30a)) * 10-005 3-Cl-Ph OCH2cPr * 10-006 3-Cl-Ph OCH2(6-Cl-(E-2a)) * 10-007 3-Cl-Ph OCH2(4-Cl-(E-2a)) * 10-008 3-Cl-Ph OCH2(5-Me-(E-18a)) 131-133 10-009 3-F-Ph Cl 132-134 10-010 3-Cl-Ph NH2 * 10-011 3-Cl-Ph OCH2(6-Br-(E-2a)) 166-168 10-012 3-Cl-Ph OCH2(5-Cl-(E-2a)) * 10-013 3-Cl-Ph OCH2(5-Me-(E-2a)) * 10-014 3-Cl-Ph OCH2(5-OMe-(E-2a)) * 10-015 3-Cl-Ph OCH2(3-Cl-(E-2a)) 125-127 10-016 3-Cl-Ph E-2a * 10-017 3-Cl-Ph 6-Cl-(E-3a) 169-171 10-018 3-Cl-Ph 6-OEt-(E-3a) 123-125 10-019 3-Cl-Ph 6-CF3-(E-3a) 188-190 10-020 3-Cl-Ph 4-C≡N-Ph 152-154 10-021 3-Cl-Ph cPr * 10-022 3-Cl-Ph CH=CH2 127-129 10-023 3-Cl-Ph CMe=CH2 112-114 10-024 3-Cl-Ph OCH2CH(OH)CF3* 10-025 3-Cl-Ph NHC(O)OMe 172-174 10-026 3-Cl-Ph NHC(O)(E-2a) 182-184 10-027 3-Cl-Ph OCH2CF2H * 10-028 3-Cl-Ph O(4-CF3-(E-2a)) 127-129 10-029 3-Cl-Ph O(6-CF3-(E-2a)) 101-103 10-030 2-OH-Ph Me 186-188 10-031 2-OH-Ph Cl 159-161 10-032 3-Cl-Ph C(O)OMe * 10-033 Ph Br 156-158 10-034 3-Me-Ph Br 146-148 10-035 3-F-Ph Br 152-154 10-036 3-CF3-Ph Br 176-178 10-037 3-Br-Ph Br 151-153 10-038 3-Cl-Ph OCH2CF2CF2H 131-132 10-039 3-Cl-Ph O(2-CF3-(E-4a)) 165-166 10-040 3-Cl-Ph O(5-CF3-(E-2a)) 73-75 10-041 3-Cl-Ph 3,5-Me2-(E-58a) * 10-042 3-Cl-Ph OCH2C(OH)2CF3 * 10-043 3-Cl-Ph 3-Me-(E-58a) * 10-044 3-Cl-Ph OCF2H * 10-045 3-Cl-Ph 2-Me-(E-29a) 135-137 10-046 3-Cl-Ph 2-Et-(E-29a) 141-143 10-047 3-Cl-Ph 2-cPr-(E-29a) 145-147 10-048 3-Cl-Ph 2-iPr-(E-29a) 127-129 10-0493-Cl-Ph 2-CH2OMe-(E-29a) * 10-050 3-Cl-Ph 2-Me-(E-30a) 147-149 10-051 3-Cl-Ph 5-Me-(E-28a) 158-160 10-052 3-Cl-Ph 1-Me-(E-23a) 79-81 10-053 3-Cl-Ph 1-Et-(E-23a) 117-119 10-054 3-Cl-Ph 1-Me-(E-22a) 167-169 10-055 3-Cl-Ph E-62a 171-173 10-056 3-Cl-Ph 3-Me-(E-43a) 133-135 10-057 3-Cl-Ph 1-H-(E-22a) * 10-058 3-Me-Ph 1-H-(E-22a) 131-133 10-059 3-Cl-Ph 1-Et-(E-22a) * 10-060 3-Me-Ph 1-Me-(E-22a) * 10-061 3-Me-Ph 1-Et-(E-22a) * 10-062 3-Cl-Ph 5-cPr-(E-45a) 145-147 10-063 3-F-Ph 5-cPr-(E-45a) 176-178 10-064 Ph 5-cPr-(E-45a) 176-178 10-065 Ph C≡N 142-144 10-066 3-F-Ph C≡N 146-148 10-067 Ph C(=NOH)NH2 214-216 10-068 3-F-Ph C(=NOH)NH2 184-186 10-069 3-Cl-Ph C(=NOH)NH2 181-183 10-070 3-Cl-Ph 1-SO2CF3-(E-22a) 144-146 10-071 3-Cl-Ph 1-SO2Me-(E-22a) 185-187 10-072 3-Cl-Ph 3-Me-(E-20a) 177-179 10-0733-Me-Ph 3-Me-(E-20a) 159-161 10-074 3-Cl-Ph 5-Me-(E-18a) 158-160 10-075 3-Me-Ph 5-Me-(E-18a) 139-141 10-076 Ph 5-Me-(E-18a) 170-172 10-077 3-Cl-Ph 1-Me-(E-63a) 170-171 10-078 Ph 1-Me-(E-63a) 180-181 10-079 3-F-Ph 1-Me-(E-63a) 176-177 10-080 3-Cl-Ph 1-Et-(E-63a) * 10-081 Ph 1-Et-(E-63a) * 10-082 3-F-Ph 1-Et-(E-63a) * 10-083 3-Cl-Ph 4-Me-(E-48a) 207-209 10-084 Ph 4-Me-(E-48a) 177-179 10-085 3-F-Ph 4-Me-(E-48a) 181-183 10-086 3-Cl-Ph 5-NMe2-(E-42a) * 10-087 Ph 5-NMe2-(E-42a) * 10-088 3-F-Ph 5-NMe2-(E-42a) * 10-089 3-Cl-Ph 5-Me-(E-45a) * 10-090 3-Cl-Ph 5-Et-(E-45a) * 10-091 3-Cl-Ph 1-nPr-(E-63a) * 10-092 Ph 1-nPr-(E-63a) 133-135 10-093 3-F-Ph 1-nPr-(E-63a) * 10-094 3-CF3-Ph 1-nPr-(E-63a) 138-140 10-095 3-Cl-Ph 1-iPr-(E-63a) * 10-096 Ph 1-iPr-(E-63a) 121-123 10-097 3-F-Ph 1-iPr-(E-63a) * 10-0983-CF3-Ph 1-iPr-(E-63a) 140-142 10-099 3-Cl-Ph 1-CH2OMe-(E-63a) * 10-100 Ph 1-CH2OMe-(E-63a) * 10-101 3-F-Ph 1-CH2OMe-(E-63a) * ―――――――――――――――――――――――――――――――――― [Table 11] ――――――――――――――――――――― No. G Z 1 m.p.(℃) ――――――――――――――――――――――― 11-001 3-Cl-...

Claims

1. Formula (1): [In the formula, G represents G-1 to G-10 or G-11, and G-1 to G-11 each represent 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 ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl, di(C １ ~C ６ represents -C(=NOR)R', １ In the relationship, when m2 is an integer of 2, each G １ may be the same or different from each other, G １ In the relationship, when m3 represents an integer of 2 or 3, each G １ may be the same or different from each other, G １ In the relationship, when m4 represents an integer of 2, 3 or 4, each G １ may be the same or different from each other, G 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, G １ In the above relationship, when m7 represents an integer of 2, 3, 4, 5, 6 or 7, each G １ may be the same or different from each other, G ２ is a hydrogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R ｂ Cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or C(alkyl)aminocarbonyl, phenyl, -C(=NOR)R', E-1 to E-62 or E-63. １ ~C ６ R' represents alkyl, １ ~C ６ represents alkyl, R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R ｃ C substituted with １ ~C ６ Alkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ -5, R Ｘ -1 to R Ｘ -5 represents a structure represented by the following structural formula, X １ is a halogen atom, cyano, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; 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, 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, R ｃ Cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents -C(=NOR)R', Ｙ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R １ is a hydrogen atom or C １ ~C ６ alkyl; W is -O- or -C(R ａ ) (R ２ )-, R ２ is a hydrogen atom or C １ ~C ６ represents alkyl, R ３ is a hydrogen atom, a hydroxyl, a halogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached; ａ is a hydrogen atom, C １ ~C ６ Alkyl, R ａ -1 to R ａ -5 or R ａ -6, R ａ -1 to R ａ -6 represents a structure represented by the following structural formula, R ５ is a hydrogen atom or C １ ~C ６ represents alkyl, R ６ is a hydrogen atom or C １ ~C ６ represents alkyl; １ When R represents an integer of 2, two R ５ and two R ６ may be the same or different from each other, R ７ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ haloalkyl or phenyl; R ８ is a hydrogen atom or C １ ~C ６ represents alkyl, R ９ is a hydrogen atom or C １ ~C ６ Z represents Z-1 to Z-62 or Z-63, each of which is a structure represented by the following structural formula: In addition, Z-4 to Z-7 and Z-49 to Z-52 １ represents a substitution on an aromatic ring; Z １ is a hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R １２ C substituted with １ ~C ６ Alkyl, -OR ｄ , -NHC(O)R ｅ , -C(O)NHR ｕ , -NHSO ２ R ｆ , -C≡CR ｇ , -SO ２ N.H. ２ , -C(=NOH)NH ２ , E-1 to E-62 or E-63; Z １ In the relationship, when n2 is an integer of 2, each Z １ may be the same or different from each other, Z １ In the case where n3 is an integer of 2 or 3, each Z １ may be the same or different from each other, Z １ In the relationship, when n4 represents an integer of 2, 3 or 4, each Z １ may be the same or different from each other, Z １ In the above relationship, when n5 is an integer of 2, 3, 4 or 5, each Z １ may be the same or different from each other, Z １ In the relationship, when n6 is an integer of 2, 3, 4, 5 or 6, each Z １ may be the same or different from each other, Z １ In the above relationship, when n7 is an integer of 2, 3, 4, 5, 6 or 7, each Z １ may be the same or different from each other, Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-62 or E-63; R ｄ is C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ alkylaminocarbonyl, E-1 to E-62 or E-63; R ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkylaminocarbonyl, C １ ~C ６ Alkoxycarbonyl, di(C １ ~C ６ R represents an alkyl)aminocarbonyl, —C(═NOR)R′, E-1 to E-62, or E-63; ｅ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, R １１ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyloxy, C １ ~C ６ Alkylamino, di(C １ ~C ６ R represents an alkyl)amino group, a benzyloxy group, E-1 to E-62, or E-63; ｕ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ alkoxy, benzyl, E-1 to E-62 or E-63; R １１ Cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R １２ Cyano, C １ ~C ６ alkoxy, E-1 to E-62 or E-63; R ｆ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, di(C １ ~C ６ alkyl)amino, E-1 to E-62 or E-63; R ｇ is a hydrogen atom or a tri(C １ ~C ４ E-1 to E-63 each represent a structure represented by the following structural formula: Z ａ is cyano, halogen atom, thiol, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; 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 v3 represents an integer of 2 or 3, 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 ａ In the relationship, when v5 represents an integer of 2, 3, 4 or 5, each Z ａ may be the same or different from each other, Z ｂ is a hydrogen atom, C １ ~C ６ Alkyl, -SO ２ R ｓ Or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ Cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) S.O. ２ R ｑ ', J-1 to J-4 or J-5; R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, J-1 to J-4 or J-5; R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino or R ｔ C substituted with １ ~C ６ represents alkylamino, R ｒ Benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 to J-4 or J-5; R ｔ is C １ ~C ６ Alkoxy, C １ ~C ６ haloalkyl, J-1 to J-4, or J-5, each of which represents a structure represented by the following structural formula: Z ｃ is C １ ~C ６ represents an alkyl or halogen atom; ｃ In the relationship, when w5 is an integer of 2, 3, 4 or 5, each Z ｃ may be the same or different from each other, Z ｃ In the relationship, when w7 is an integer of 2, 3, 4, 5, 6 or 7, each Z ｃ may be the same or different from each other, Z ｃ In the relationship, when w8 is an integer of 2, 3, 4, 5, 6, 7 or 8, each Z ｃ may be the same or different from each other, Z ｃ In the above relationship, when w10 is an integer of 2, 3, 4, 5, 6, 7, 8, 9, or 10, each Z ｃ may be the same as or different from each other, m2 represents an integer of 0, 1 or 2, m3 represents an integer of 0, 1, 2 or 3, m4 represents an integer of 0, 1, 2, 3 or 4, m5 represents an integer of 0, 1, 2, 3, 4 or 5, m7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, u4 represents an integer of 0, 1, 2, 3 or 4, u5 represents an integer of 0, 1, 2, 3, 4 or 5, n7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, n6 represents an integer of 0, 1, 2, 3, 4, 5 or 6, n5 represents an integer of 0, 1, 2, 3, 4 or 5, n4 represents an integer of 0, 1, 2, 3, or 4; n3 represents an integer of 0, 1, 2, or 3; n2 represents an integer of 0, 1, or 2; n1 represents an integer of 0 or 1; p represents an integer of 0, 1, or 2; r １ represents an integer of 1 or 2; ２ represents an integer of 0 or 1, t represents an integer of 0, 1 or 2, v1 represents an integer of 0 or 1, v2 represents an integer of 0, 1 or 2, v3 represents an integer of 0, 1, 2 or 3, v4 represents an integer of 0, 1, 2, 3 or 4, v5 represents an integer of 0, 1, 2, 3, 4 or 5, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

2. G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents an alkylsulfonyl group; ２ is C １ ~C ６ represents alkyl, R ｂ Cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ R represents alkoxy or E-1; Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano or C １ ~C ６ represents haloalkyl; R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, R ５ represents a hydrogen atom; ６ represents a hydrogen atom; R ７ is C １ ~C ６ represents alkyl, Z is Z-1, Z-3, Z-4, Z-6, Z-8, Z-9, Z-10, Z-11, Z-18, Z-23, Z-25, Z-26, Z -27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42, Z-49, Z-53, Z-58 or Z-60, Z １ is a carboxy, hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -C(=NOH)NH ２ , represents E-1 to E-3, E-5, E-18, E-20, E-21, E-22, E-23, E-28 to E-30, E-40, E-41, E-42, E-43 to E-45, E-48, E-58, E-62 or E-63, Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5; R ｄ represents E-2 or E-4; ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; ａ is a halogen atom, hydroxy, thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-4 or J-5; Z ｂ is a hydrogen atom, C １ ~C ６ Alkyl, -SO ２ R ｓ Or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ Cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, -C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) S.O. ２ R ｑ ' or J-5; R ｋ is C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino, J-2 or J-5; R ｎ ' is C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy or J-5; R ｑ ' is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R ｒ Benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔ represents J-5, m2 represents an integer of 0 or 1, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0 or 2, u5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 0, 1, 2 or 3, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0, 1 or 2, n1 represents an integer of 1, r １ represents an integer of 1, v2 represents an integer of 0 or 1, v3 represents an integer of 0 or 1, v4 represents an integer of 0, 1 or 2, v5 represents an integer of 0 or 1, w5 represents an integer of 0, w7 represents an integer of 0, w8 represents an integer of 0 or 1, and w10 represents an integer of 0. The pyrazole compound or a salt thereof according to claim 1 .

3. W is -C(R ａ ) (R ２ )-, G １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl or C １ ~C ６ represents an alkylsulfonyl group; ２ is C １ ~C ６ represents alkyl, R ｂ Cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ R represents alkoxy or E-1; Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 to R Ｘ -4 or R Ｘ represents -5, and X １ is a halogen atom, cyano or C １ ~C ６ represents haloalkyl; R Ｙ represents a hydrogen atom; １ represents a hydrogen atom; ａ is a hydrogen atom, C １ ~C ６ Alkyl or R ａ represents −1, R ５ represents a hydrogen atom; R ６ represents a hydrogen atom; R ７ is C １ ~C ６ represents alkyl, Z represents Z-1, Z-3, Z-4, Z-8, Z-9, Z-11, Z-25, Z-26, Z-33, Z-34, Z-41, Z-42, Z-53, Z-58 or Z-60, Z １ is a hydroxyl, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, R ｈ C substituted with １ ~C ６ Haloalkoxy, C １ ~C ６ Alkoxycarbonyl, -OR ｄ , -NHC(O)R ｅ , -C(=NOH)NH ２ , represents E-1 to E-3, E-18, E-20, E-21, E-22, E-23, E-28 to E-30, E-40 to E-45, E-48, E-58, E-62 or E-63, Z ２ represents E-2; R ｄ represents E-2 or E-4; ｈ is hydroxy, cyano, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, C ２ ~C ６ Alkenyl, C ２ ~C ６ alkynyl, E-1 to E-3, E-18 or E-30; R ｅ is C １ ~C ６ represents alkoxy or E-2; ａ is a halogen atom, a thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylsulfinyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , -SO ２ R ｓ , J-1 to J-3 or J-5; Z ｂ is a hydrogen atom, C １ ~C ６ Alkyl, -SO ２ R ｓ Or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ Cyano, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylamino, -C(O)R ｍ , -N(R ｐ ) C(O)R ｐ ', -N(R ｑ ) S.O. ２ R ｑ ' or J-5; R ｋ is C １ ~C ６ represents alkyl, R ｍ Is Ji (C １ ~C ６ alkyl)amino, J-2 or J-5; R ｎ ' is C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ Alkyl, C １ ~C ６ alkoxy or J-5; R ｑ ' is C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R ｒ Benzyl, C １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｓ is C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkylamino, R ｔ C substituted with １ ~C ６ alkylamino, J-1 or J-2; R ｔ represents J-5, m2 represents an integer of 0 or 1, m3 represents an integer of 0 or 1, m4 represents an integer of 1, m5 represents an integer of 0, 1 or 2, m7 represents an integer of 0, u4 represents an integer of 0 or 2, u5 represents an integer of 0, 1 or 2, n7 represents an integer of 0, n5 represents an integer of 1, 2 or 3, n4 represents an integer of 1 or 2, n3 represents an integer of 0, 1 or 2, n2 represents an integer of 1, n1 represents an integer of 1, p represents an integer of 0 or 1, r １ represents an integer of 1; v2 represents an integer of 0 or 1; v4 represents an integer of 0, 1 or 2; v5 represents an integer of 1; w5 represents an integer of 0; w7 represents an integer of 0; and w8 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to claim 1 .

4. W represents -O-; G １ is a halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; R Ｘ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, benzyl, R Ｘ -1 or R Ｘ -2, R Ｙ represents a hydrogen atom; R １ represents a hydrogen atom; R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ represents a hydrogen atom, Z is Z-1, Z-6, Z-8, Z-9, Z-10, Z-11, Z-18, Z-23, Z-26, Represents Z-27, Z-28, Z-30, Z-33, Z-34, Z-41, Z-42 or Z-49, Z １ is a carboxy, cyano, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, R ｈ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkylthio, C １ ~C ６ alkoxycarbonyl, E-2, E-3, E-5, E-18, E-20, E-21, E-23, E-28, E-29, E-30, E-40, E-41, E-42 or E-63; Z ２ is a hydrogen atom, C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ alkyl, E-1 to E-3 or E-5; R ｈ is C ３ ~C １０ Cycloalkyl, C １ ~C ６ alkoxy, E-2 or E-3; Z ａ is a halogen atom, hydroxy, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; ｂ is C １ ~C ６ Alkyl or R ｈ C substituted with １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', R ｋ is C １ ~C ６ represents alkyl, R ｋ R ′ represents a hydrogen atom; ｍ Is Ji (C １ ~C ６ R represents an alkyl)amino group or J-2; ｎ is C １ ~C ６ represents alkyl, R ｎ ' is C １ ~C ６ represents alkyl, R ｐ represents a hydrogen atom; ｐ ' represents J-5; ｑ is C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ represents alkyl, R ｒ is C １ ~C ６ m5 represents an integer of 0 or 1, n5 represents an integer of 0, 1 or 2, n4 represents an integer of 0, 1 or 2, n3 represents an integer of 0 or 1, n1 represents an integer of 1, u5 represents an integer of 0, u4 represents an integer of 0, v5 represents an integer of 0, v4 represents an integer of 0 or 1, v3 represents an integer of 0 or 1, v2 represents an integer of 0 or 1, v1 represents an integer of 1, w8 represents an integer of 0, and w10 represents an integer of 0.

5. G represents G-1, G-2, G-3 or G-4; １ is a hydroxyl, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents haloalkoxy; R Ｘ is C １ ~C ６ Alkyl or C ３ ~C １０ represents cycloalkyl, R Ｙ represents a hydrogen atom; R １ represents a hydrogen atom; R ２ represents a hydrogen atom; R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that R forms a 3- to 6-membered ring together with the carbon atom to which it is attached; ａ is a hydrogen atom or C １ ~C ６ Z represents Z-1, Z-8, Z-9, Z-10, Z-11, Z-25, Z-26, Z-33, Z-34 or Z-49; １ is a carboxy, hydroxy, amino, nitro, cyano, halogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, C ２ ~C ５ Alkenyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C １ ~C ６ haloalkoxy, E-40, E-41 or E-63; Z ２ is a hydrogen atom, C １ ~C ６ represents alkyl or E-1; Z ａ is a halogen atom, hydroxy, thiol, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, R ｊ C substituted with ２ ~C ６ Alkenyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', R ｊ is C １ ~C ６ represents alkoxy; R ｋ is C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl; Z ｂ is a hydrogen atom or C １ ~C ６ m5 represents an integer of 0 or 1; n6 represents an integer of 0, 1 or 2; n7 represents an integer of 0 or 1; n8 represents an integer of 0 or 1; n9 represents an integer of 0, 1 or 2; n1 represents an integer of 0 or 1; n2 represents an integer of 1; v3 represents an integer of 0; and v4 represents an integer of 0 or 1. The pyrazole compound or a salt thereof according to claim 1 or 2, 6. G represents G-1, 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 ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ By forming an alkylene chain, R ３ and R ４ represents that R forms a three-membered ring together with the carbon atom to which it is bonded; ａ represents a hydrogen atom, Z represents Z-1, Z １ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ alkoxy, E-40, E-41 or E-63; Z ａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino or -C(=NOR ｋ ) R ｋ ', Z ｂ is C １ ~C ６ m5 represents an integer of 1; and n5 represents an integer of 1 or 2, or a salt thereof. The pyrazole compound or a salt thereof according to claim 5 .

7. Formula (1-1a): [In the formula, R ｚ is R ｚ -1, R ｚ -2 or R ｚ -3, R ｚ -1, R ｚ -2 and R ｚ -3 represents a structure represented by the following structural formula, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that the ring is formed of 3 to 6 members together with the carbon atom to which it is bonded; １ represents E-40 or E-41, and E-40 and E-41 each represent a structure represented by the following structural formula: Z ａ is hydroxy, C １ ~C ６ Alkyl, difluoromethyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ J-1 to J-5 each represent a structure represented by the following structural formula: R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｒ is C １ ~C ６ represents alkyl, R ｖ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl; R ｗ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ v1 represents an integer of 1, w5 represents an integer of 0, 1, 2, 3, 4, or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6, or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

8. Formula (1-1a): [In the formula, R ｚ is R ｚ -1, R ｚ -2 or R ｚ -3, R ｚ -1, R ｚ -2 and R ｚ -3 represents a structure represented by the following structural formula, R ３ is a hydrogen atom or C １ ~C ６ represents alkyl, R ４ is a hydrogen atom or C １ ~C ６ represents alkyl, or R ３ and R ４ Together, C ２ ~C ６ By forming an alkylene chain, R ３ and R ４ represents that the ring is formed of 3 to 6 members together with the carbon atom to which it is bonded; １ represents E-18, E-20, E-22, E-23, E-24, E-28, E-29, E-30, E-42 or E-63, and E-18, E-20, E-22, E-23, E-24, E-28, E-29, E-30, E-42 and E-63 each represent a structure represented by the following structural formula: Z ａ is C ２ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylamino, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , -N(R ｎ ) OR ｎ ', -N(R ｑ ) S.O. ２ R ｑ ', -SR ｒ , J-1, J-2 or J-4; ａ In the relationship, when v2 represents an integer of 2, each Z ａ may be the same or different from each other, Z ｂ is C １ ~C ６ Alkyl, R ｈ C substituted with １ ~C ６ Alkyl or -SO ２ R ｓ represents ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', R ｋ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｋ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｍ is C １ ~C ６ Alkyl, di(C １ ~C ６ J-1 to J-5 each represent a structure represented by the following structural formula: R ｎ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｎ ' is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｐ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｑ is a hydrogen atom or C １ ~C ６ represents alkyl, R ｑ ' is C １ ~C ６ alkyl, J-1 to J-4 or J-5; R ｒ is C １ ~C ６ represents alkyl, R ｖ is a hydrogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl or C １ ~C ６ represents haloalkyl; R ｗ is a hydrogen atom, C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ haloalkyl, v1 represents an integer of 1, v2 represents an integer of 1 or 2, w5 represents an integer of 0, 1, 2, 3, 4 or 5, w7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, w8 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7 or 8, and w10 represents an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

9. R ４ represents a hydrogen atom; Z ａ is C １ ~C ６ Alkyl, difluoromethyl, C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, di(C １ ~C ６ alkyl)amino, -C(=NOR ｋ ) R ｋ ', -C(O)R ｍ , J-1 or J-2; R ｊ is C １ ~C ６ Alkoxy or -N(R ｐ ) C(O)R ｐ ', R ｋ is C １ ~C ６ represents alkyl, R ｋ R ′ represents a hydrogen atom; ｍ Is Ji (C １ ~C ６ R represents an alkyl)amino group or J-2; ｐ represents a hydrogen atom; R ｐ ' represents J-5; ｖ is C １ ~C ６ Alkyl or C １ ~C ６ represents alkoxy; R ｗ is C １ ~C ６ The intermediate or a salt thereof according to claim 7 , wherein w5 represents an integer of 0, w8 represents an integer of 0, and w10 represents an integer of 0.

10. R ３ represents a hydrogen atom; ４ represents a hydrogen atom; Z ａ is C ３ ~C １０ Cycloalkyl, R ｊ C substituted with １ ~C ６ Alkyl, C １ ~C ６ Alkylamino or di(C １ ~C ６ (alkyl)amino; Z ｂ is C １ ~C ６ represents alkyl, R ｊ is C １ ~C ６ represents alkoxy; R ｖ is C １ ~C ６ represents alkoxy; R ｗ is C １ ~C ６ The intermediate according to claim 8, or a salt thereof, wherein R represents an alkyl group.

11. Formula (1-2a): W １ is -OR １３ Or -N(R １ ) OH; 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 ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxy, R ｂ C substituted with １ ~C ６ Alkoxy, C １ ~C ６ Haloalkoxy, C １ ~C ６ Alkylthio, C １ ~C ６ Alkylsulfinyl, C １ ~C ６ Alkylsulfonyl, di(C １ ~C ６ alkyl)amino, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, C ３ ~C １０ Cycloalkylaminocarbonyl, di(C １ ~C ６ R represents -C(=NOR)R', ｂ Cyano, C ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, C １ ~C ６ Alkoxy, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxycarbonyl, C １ ~C ６ Alkylaminocarbonyl, di(C １ ~C ６ R represents a hydrogen atom or a C(=NOR)aminocarbonyl, a phenyl, or a C(=NOR)R' １ ~C ６ R' represents alkyl, １ ~C ６ represents alkyl, R Ｙ is a hydrogen atom, a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ represents haloalkyl; R １ is a hydrogen atom or C １ ~C ６ represents alkyl, R １３ is a hydrogen atom or C １ ~C ６ 7. The pyrazole compound according to claim 1 , wherein R represents an alkyl group.

12. W １ is -OR １３ represents １ is a hydroxyl, halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or C １ ~C ６ represents alkoxy; R Ｙ represents a hydrogen atom; １３ The intermediate or a salt thereof according to claim 11, wherein represents a hydrogen atom.

13. W １ is -N(R １ ) OH; G １ represents a halogen atom; Ｙ represents a hydrogen atom; １ The intermediate or a salt thereof according to claim 11, wherein represents a hydrogen atom.

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

15. A fungicide comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 6.

16. An agricultural or horticultural fungicide comprising, as an active ingredient, one or more pyrazole compounds or salts thereof according to any one of claims 1 to 6.

17. An antifungal agent comprising, as an active ingredient, one or more pyrazole compounds and salts thereof according to any one of claims 1 to 6.

18. An internal parasite control agent comprising, as an active ingredient, one or more selected from the pyrazole compounds and salts thereof according to any one of claims 1 to 6.

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