Pyrazole compounds and pest control agents

Abstract

This invention provides pyrazole compounds of formula (1) or their salts, and novel fungicides containing them as active ingredients, particularly fungicides for agricultural and horticultural use. In the formula, G represents G-1, G... 1 Indicates C1-C6 alkyl groups, etc., R X Indicates C1-C6 alkyl groups, etc., R Y R represents hydrogen atoms, etc. 1 R represents hydrogen atoms, etc. 2 R represents hydrogen atoms, etc. 3 R represents hydrogen atoms, etc. 4 R represents hydrogen atoms, etc. 5 Z represents hydrogen atoms, etc. 1 Indicates E-1, etc., Z a Indicates C1-C6 alkyl groups, etc., Z 2 The symbols represent C1 to C6 alkyl groups, m5 represents the integer 0, 1, 2, 3, 4 or 5, n4 represents the integer 0, 1, 2, 3 or 4, p represents the integer 0 or 1, and v2 represents the integer 0, 1 or 2.

Description

Technical Field

[0001] This invention relates to novel pyrazole compounds and their salts, as well as pest control agents containing the compounds and their salts as active ingredients. Background Technology

[0002] Patent documents 1 and 2 disclose certain pyrazole compounds, but there is no disclosure regarding the pyrazole compounds involved in this invention.

[0003] In addition, Patent Documents 3 and 4 disclose that certain pyrazole compounds are useful as bactericides, but there is no disclosure regarding the pyrazole compounds involved in this invention.

[0004] Furthermore, Patent Documents 5-8 disclose the usefulness of certain heterocyclic compounds as bactericides, but there is no disclosure regarding the pyrazole compounds involved in this invention.

[0005] [Existing technical documents] (Patent Documents) Patent Document 1: International Publication No. 2002 / 085860 Patent Document 2: International Publication No. 2006 / 132197 Patent Document 3: International Publication No. 2009 / 028280 Patent Document 4: International Publication No. 1996 / 038419 Patent Document 5: International Publication No. 2020 / 109391 Patent Document 6: International Publication No. 2021 / 224220 Patent Document 7: International Publication No. 2021 / 228734 Patent document 8: International publication No. 2021 / 233861. Summary of the Invention

[0006] (The problem that the invention aims to solve) However, long-term use of pesticides can lead to pathogens developing resistance. Therefore, there is a long-standing expectation to develop new pesticides with excellent control effects.

[0007] (Technical means used to solve the problem) The inventors conducted in-depth research with the goal of solving the above-mentioned problems, and found that the novel pyrazole compound shown in the following formula (1) of the present invention exhibits excellent control activity as a fungicide, especially as an agricultural and horticultural fungicide, thus completing the present invention.

[0008] The pyrazole compounds involved in this invention are not disclosed in any literature, and their usefulness as pest control agents is unknown.

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

[0010] [1] A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 1]

[0011] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 2]

[0012] G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, Regarding G 1 The relationships between them, when m5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. R X Indicates C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1、R X -2, R X -3 or R X -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 3]

[0013] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5 Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-29 or E-30. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-30 each represent the structure shown in the following structural formulas. [Chemical Formula 4]

[0014] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: aThey are the same or different from each other. Regarding Z a The relationships between them, when v4 represents integers 2, 3, or 4, are as follows: a They are the same or different from each other. Z b Indicates C1 to C6 alkyl groups. R a This indicates hydroxyl, cyano, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino, phenylcarbonylamino, -ОR g -C(О)R g -NR h SO2R j Or Q-1, Q-1 represents the structure shown in the following structural formula. [Chemical Formula 5]

[0015] Q 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. Regarding Q 1 The relationships between them, when w5 represents integers 2, 3, 4, or 5, are as follows: 1 They are the same or different from each other. R b Indicates a hydrogen atom or a C1-C6 alkyl group. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R d Indicates amino, hydroxyamino, C1-C6 alkylamino, C3-C6 alkylamino, C4-C6 alkylamino. 10 Cycloalkylamino, di(C1-C6)amino, pyrrolid-1-yl, morpholin-1-yl, or piperidin-1-yl R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy R f This represents a hydrogen atom, hydroxyl group, C1-C6 alkyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, C1-C6 alkylamino carbonyl group, di(C1-C6 alkyl)amino carbonyl group, C1-C6 alkyl sulfonyl group, or C1-C6 haloalkyl sulfonyl group. R g Indicates Q-1, R h Indicates a hydrogen atom or a C1-C6 alkyl group. R j Indicates C1 to C6 alkyl groups. m5 represents the integers 0, 1, 2, 3, 4, or 5. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v4 represents the integer 0, 1, 2, 3, or 4. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1. w5 represents the integers 0, 1, 2, 3, 4, or 5.

[0016] (Invention effect) The compounds of the present invention shown in formula (1) exhibit excellent antimicrobial activity against many pathogens.

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

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

[0019] In the compounds of the present invention, depending on the type of substituent, there are sometimes geometric isomers of E-body and Z-body, and the compounds of the present invention include these E-body, Z-body, or mixtures containing E-body and Z-body in any proportion.

[0020] Furthermore, the compounds of the present invention sometimes contain optically active substances due to the presence of one or more asymmetric carbon atoms or asymmetric sulfur atoms, and the compounds of the present invention include all such optically active substances or racemates.

[0021] Furthermore, the compounds of the present invention sometimes contain tautomers depending on the type of substituent, and the compounds of the present invention include all of these tautomers or mixtures containing these tautomers in any proportion.

[0022] Furthermore, in the compounds of the present invention, due to the steric hindrance between the substituents, bond rotation may sometimes exist as one or more rotational isomers, and the compounds of the present invention include all of these rotational isomers or a mixture of diastereomers containing them in any proportion.

[0023] Specific examples of the substituents shown in this specification are given below. Here, n-, i-, s-, and tert- represent n-, iso-, secondary-, and tert-, respectively, and Ph represents phenyl.

[0024] In this specification, "halogen atom" includes fluorine, chlorine, bromine, and iodine atoms. Furthermore, the term "halogen" in this specification also refers to these halogen atoms.

[0025] The "C" in this instruction manual a ~C b The term "alkyl" indicates a straight-chain or branched saturated hydrocarbon group with a to b carbon atoms. As "C a ~C b Specific examples of "alkyl" include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, tert-butyl, n-pentyl, 1,1-dimethylpropyl, and n-hexyl. "C" a ~C b "alkyl" is selected from a specified range of carbon atoms.

[0026] The "C" in this instruction manual a ~C b The term "haloalkyl" refers to a straight-chain or branched saturated hydrocarbon group with a number of carbon atoms, where any hydrogen atom bonded to a carbon atom has been substituted with a halogen atom. When two or more halogen atoms are substituted, these halogen atoms can be the same or different from each other. As "C a ~C b Specific examples of "halogenated alkyl" include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, monochlorodifluoromethyl, trichloromethyl, monobromodifluoromethyl, 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, etc. "C" a ~C b "Halogenated alkyl" is selected from a specified range of carbon atoms.

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

[0028] The "C" in this instruction manual a ~Cb The term "alkynyl group" indicates a straight-chain or branched unsaturated hydrocarbon group with a to b carbon atoms and one or more triple bonds within the molecule. As "C a ~C b Specific examples of "alkynyl" include ethynyl, propynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and 1-hexynyl. "C" a ~C b "Alkyne group" is selected from a specified range of carbon atoms.

[0029] The "C" in this instruction manual a ~C b The expression "alkoxy group" indicates an alkyl group with a to b carbon atoms, as described above (-O-). As "C a ~C b Specific examples of "alkoxy" include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, tert-butoxy, and 2-ethylhexyloxy. "C" a ~C b "Alkoxy" is selected from a specified range of carbon atoms.

[0030] The "C" in this instruction manual a ~C b The expression "haloalkoxy" indicates a halogenated alkyl group with a to b carbon atoms, as described above. a ~C b Specific examples of "haloalkoxy" include difluoromethoxy, trifluoromethoxy, monochlorodifluoromethoxy, monobromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropoxy, etc. a ~C b "Haloalkoxy" is selected from a specified range of carbon atoms.

[0031] The "C" in this instruction manual a ~C b The expression "alkyl thio" indicates an alkyl group with a to b carbon atoms, as described above. a ~C b Specific examples of "alkyl thio" include methyl thio, ethyl thio, n-propyl thio, i-propyl thio, n-butyl thio, i-butyl thio, s-butyl thio, and tert-butyl thio. "C" a ~C b "alkylthio" is selected from a specified range of carbon atoms.

[0032] The "C" in this instruction manuala ~C b The expression "halogenated alkyl thioyl" indicates a halogenated alkyl group with a to b carbon atoms, as described above. As "C a ~C b Specific examples of "haloalkylthio" include difluoromethylthio, trifluoromethylthio, monochlorodifluoromethylthio, monobromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2,-tetrafluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, and 1,1,2,3,3,3-hexafluoropropylthio, etc. a ~C b "Halogenated alkyl thio" is selected from a specified range of carbon atoms.

[0033] The "C" in this instruction manual a ~C b The expression "alkyl sulfinyl" indicates an alkyl group with a carbon number of a to b, as described above. Here, -S(O)- can also be abbreviated as -SO-. As "C a ~C b Specific examples of "alkyl sulfinyl" include methyl sulfinyl, ethyl sulfinyl, n-propyl sulfinyl, i-propyl sulfinyl, n-butyl sulfinyl, i-butyl sulfinyl, S-butyl sulfinyl, and tert-butyl sulfinyl. "C" a ~C b "alkylsulfinyl" is selected from a specified range of carbon atoms.

[0034] The "C" in this instruction manual a ~C b The expression "alkylsulfonyl" indicates an alkyl group with a to b carbon atoms, as described above (-SO2-). As "C a ~C b Specific examples of "alkylsulfonyl" include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, and tert-butylsulfonyl. a ~C b "alkylsulfonyl" is selected from a specified range of carbon atoms.

[0035] The "C" in this instruction manual a ~C b The expression "halogenated alkyl sulfonyl" indicates a halogenated alkyl group with a to b carbon atoms, as described above. As "C a ~C bSpecific examples of "halogenated alkyl sulfonyl" include, for instance, difluoromethylsulfonyl, trifluoromethylsulfonyl, monochlorodifluoromethylsulfonyl, monobromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 1,1,2,2-tetrafluoroethylsulfonyl, 2-chloro-1,1,2-trifluoroethylsulfonyl, and 1,1,2,3,3,3-hexafluoropropylsulfonyl, etc. "C" a ~C b "Halogenated alkyl sulfonyl" is selected from a specified range of carbon atoms.

[0036] The "C" in this instruction manual a ~C b The term "cycloalkyl" indicates a cyclic hydrocarbon group with a to b carbon atoms. a ~C b Cycloalkyl groups can, for example, form monocyclic or complex cyclic structures ranging from 3-membered to 10-membered rings. Furthermore, the hydrogen atoms in each ring can be arbitrarily substituted by alkyl groups within a specified range of carbon atoms. As for "C..." a ~C b Specific examples of "cycloalkyl" include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. a ~C b "Cycloalkyl" is selected from a specified range of carbon atoms.

[0037] The "C" in this instruction manual a ~C b The term "halocycloalkyl" indicates a cyclic hydrocarbon group with a number of carbon atoms (a to b) resulting from the substitution of any hydrogen atom bonded to a carbon atom with a halogen atom. When two or more halogen atoms are substituted, these halogen atoms can be the same or different from each other. As "C a ~C b Specific examples of "halogenated cyclopropyl" include, for instance, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, 2,2-dibromocyclopropyl, 2,2-difluoro-1-methylcyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 2,2-dibromo-1-methylcyclopropyl, and 2,2,3,3-tetrafluorocyclobutyl. a ~C b "Halogenated cycloalkyl" is selected from a specified range of carbon atoms.

[0038] The "C" in this instruction manual a ~C b The expression "alkylamino" indicates an amino group in which one hydrogen atom is replaced by an alkyl group with a number of carbon atoms of the aforementioned meaning. As "C a ~C bSpecific examples of "alkylamino" include methylamino, ethylamino, n-propylamino, i-propylamino, n-butylamino, i-butylamino, and tert-butylamino. a ~C b "alkylamino" is selected from a specified range of carbon atoms.

[0039] The "C" in this instruction manual a ~C b The expression "cycloalkylamino" indicates an amino group in which one hydrogen atom is replaced by a cycloalkyl group with a number of carbon atoms of the aforementioned meaning. As "C a ~C b Specific examples of "cycloalkylamino" include cyclopropylamino, cyclobutylamino, cyclopentylamino, and cyclohexylamino. a ~C b "Cycloalkylamino" is selected from a specified range of carbon atoms.

[0040] The term "two (C)" in this instruction manual a ~C b The expression "alkyl)amino" indicates that two hydrogen atoms are replaced by an amino group with a number of carbon atoms (a to b) that can be the same or different from the aforementioned alkyl group. As "di(C)amino", this expression signifies an amino group in which two hydrogen atoms are replaced by an alkyl group (a to b) of the aforementioned meaning. a ~C b Specific examples of "alkyl)amino" include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, and di(n-butyl)amino. a ~C b The alkyl groups in "alkyl)amino" are selected from a specified range of carbon atoms.

[0041] The "C" in this instruction manual a ~C b The expression "alkyl carbonyl" indicates an alkyl group with a number of carbon atoms (a to b) as described above (-C(O)-). As "C a ~C b Specific examples of "alkyl carbonyl" include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutyryl, neovaleryl, hexanoyl, and heptanoyl. a ~C b "alkyl carbonyl" is selected from a specified range of carbon atoms.

[0042] The "C" in this instruction manual a ~C b The expression "alkoxycarbonyl" indicates an alkyl group with a number of carbon atoms (a to b) as described above (-OC(O)-). As "C a ~C bSpecific examples of "alkoxycarbonyl" include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, i-propoxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl. a ~C b "Alkoxycarbonyl" is selected from a specified range of carbon atoms.

[0043] The "C" in this instruction manual a ~C b The expression "alkylaminocarbonyl" indicates that one hydrogen atom is replaced by an alkyl group, which is an alkyl group with a number of carbon atoms as described above. As "C a ~C b Specific examples of "alkylaminocarbonyl" include methylcarbamoyl, ethylcarbamoyl, n-propylcarbamoyl, i-propylcarbamoyl, n-butylcarbamoyl, i-butylcarbamoyl, s-butylcarbamoyl, and tert-butylcarbamoyl. a ~C b "alkylaminocarbonyl" is selected from a specified range of carbon atoms.

[0044] The "C" in this instruction manual a ~C b The expression "cycloalkylaminocarbonyl" indicates that one hydrogen atom is replaced by a carbamoyl group with a number of carbon atoms of the aforementioned cycloalkyl group. As "C a ~C b Specific examples of "cycloalkylaminocarbonyl" include cyclopropylcarbamoyl, cyclobutylcarbamoyl, cyclopentylcarbamoyl, and cyclohexylcarbamoyl. a ~C b "Cycloalkylaminocarbonyl" is selected from a specified range of carbon atoms.

[0045] The term "two (C)" in this instruction manual a ~C b The expression "alkylaminocarbonyl" indicates that both hydrogen atoms are replaced by an alkyl group (which may be the same as or different from the aforementioned meaning) of the form, consisting of a to b carbon atoms. As "di(C... a ~C b Specific examples of "alkylaminocarbonyl" include N,N-dimethylcarbamoyl, N-ethyl-N-methylcarbamoyl, N,N-diethylcarbamoyl, N,N-di(n-propyl)carbamoyl, and N,N-di(n-butyl)carbamoyl. a ~C b In "alkylaminocarbonyl", each alkyl group is selected from a specified range of carbon atoms.

[0046] The "C" in this instruction manual a ~C b The expression "alkylcarbonyloxy" indicates an alkyl group with a to b carbon atoms, as described above (-C(O)O-). As "C a ~C b Specific examples of "alkyl carbonyloxy" include acetoxy, propionyloxy, butyryloxy, isobutyryloxy, valeryloxy, isovaleryloxy, 2-methylbutyryloxy, neovaleryloxy, hexanoyloxy, and heptanyloxy. a ~C b "alkylcarbonyloxy" is selected from a specified range of carbon atoms.

[0047] The "C" in this instruction manual a ~C b The expression "alkyl carbonyl amino" indicates an alkyl group with a to b carbon atoms, as described above: -C(O)NH-. As "C a ~C b Specific examples of "alkyl carbonyl amino" include acetamido, propionylamino, and butyrylamino. a ~C b "alkylcarbonylamino" is selected from a specified range of carbon atoms.

[0048] In this specification, "phenylcarbonylamino" is used to represent C6H5-C(O)NH-.

[0049] The term "halosulfonyloxy" in this specification refers to the halogen atom -SO2-O- as described above. Specific examples of "halosulfonyloxy" include fluorosulfonyloxy and chlorosulfonyloxy.

[0050] The "C" in this instruction manual a ~C b The expression "alkoxycarbonyloxy" indicates an alkoxy group with a to b carbon atoms, as described above: -C(O)O-. As "C a ~C b Specific examples of "alkoxycarbonyloxy" include methoxycarbonyloxy and ethoxycarbonyloxy. a ~C b "Alkoxycarbonyloxy" is selected from a specified range of carbon atoms.

[0051] The "C" in this instruction manual a ~C b The expression "alkylsulfonyloxy" indicates an alkyl group with a carbon number of a to b, as described above (-SO2-O-). As "C a ~C b Specific examples of "alkylsulfonyloxy" include methanesulfonyloxy and ethanesulfonyloxy.a ~C b "alkylsulfonyloxy" is selected from a specified range of carbon atoms.

[0052] The "C" in this instruction manual a ~C b The expression "halogenated alkyl sulfonyloxy" indicates a halogenated alkyl group with a to b carbon atoms, as described above (-SO2-O-). As "C a ~C b Specific examples of "halogenated alkyl sulfonyloxy" include, for example, trifluoromethanesulfonyloxy and chloromethylsulfonyloxy. "C" a ~C b "Halogenated alkyl sulfonyloxy" is selected from a specified range of carbon atoms.

[0053] In this specification, the term "aryl" refers to an aromatic cyclic group having 6 to 10 carbon atoms. Specific examples include phenyl, α-naphthyl, and β-naphthyl, with phenyl being preferred. The aforementioned aryl group may be substituted with 1 to 3 halogen atoms, alkyl, alkoxy, cyano, nitro, etc.

[0054] The term "arylsulfonyloxy" in this specification refers to the aryl group with the aforementioned meaning (-SO2-O-). Specific examples of "arylsulfonyloxy" include phenylsulfonyloxy and p-toluenesulfonyloxy.

[0055] In this specification, the term "hydroxyamino" refers to HO-NH-.

[0056] In this specification, the term "thiol" refers to HS-.

[0057] The term "via R" in this instruction manual a Replaced C a ~C b The term "alkyl" indicates that any hydrogen atom bonded to the carbon atom of an alkyl group is replaced by one or more substituents R. a Alkyl groups with a to b carbon atoms, partially or completely substituted, as defined above. Each is selected from the specified range of carbon number. When there are two or more substituents R... a At that time, these substituents R a They can be the same as each other, or they can be different from each other.

[0058] In this specification, the term "benzyl" indicates -CH2C6H5.

[0059] Next, the preparation method of the compound of the present invention shown in Formula (1) will be described. The compound of the present invention shown in Formula (1) can be prepared, for example, by the following method. Here, the following description is only illustrative, and the compound of the present invention shown in Formula (1) can also be prepared by other methods. Hereinafter, "the compound of the present invention shown in Formula (1)" will also be referred to as "compound (1)", and "the compound shown in Formula (2)" will also be referred to as "compound (2)". Other compounds will also be described in the same manner.

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

[0061] [Chemical Formula 6]

[0062] [In the formula, J] 1 Represents chlorine atom, bromine atom, C1-C4 alkyl carbonyloxy group, or C1-C4 alkoxy carbonyloxy group (e.g., methoxy carbonyloxy group), G, R X R Y R 1 R 2 R 3 R 4 R 5 Z 1 Z 2 The meanings of n4 and p are the same as described above. Compound (1) can be prepared by reacting compound (2), compound (3) or its salts (e.g. hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) with a dehydrating condensing agent in a solvent or in solvent-free conditions and, if applicable, in the presence of either or both of a base and an additive.

[0063] Alternatively, compound (1) can also be prepared by reacting compound (2-1) with compound (3) or its salts (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or in solvent-free conditions and, if applicable, in the presence of either or both of a base and an additive.

[0064] The amount of compound (3) or its salt and dehydrating condensing agent used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2) or compound (2-1).

[0065] Some of the compounds shown in compound (3) are known compounds and are available from commercially available products. In addition, the other compounds shown in compound (3) can also be prepared according to the general known synthetic methods described in the literature.

[0066] Examples of dehydrating condensing agents include 1H-benzotriazol-1-yl-oxotris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazol[4,5-b]pyridinium 3-oxohexafluorophosphate.

[0067] If a solvent is used, it need to be inactive to the reaction. Examples of such solvents include: water; alcohols such as methanol, ethanol, or tert-butanol; ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, or diethylene glycol dimethyl ether; aromatic hydrocarbons such as benzene, xylene, or toluene; aliphatic hydrocarbons such as n-pentane, n-hexane, or cyclohexane; halogenated hydrocarbons such as dichloromethane, chloroform, or 1,2-dichloroethane; nitrile solvents such as acetonitrile or propionitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or N,N'-dimethylimidazolium ketone; dimethyl sulfoxide; pyridine; or mixtures thereof; etc.

[0068] The reaction can be carried out in the presence of a base. Examples of bases that can be used include: organic bases such as pyridine, 2,6-dimethylpyridine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), or 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, or potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, or potassium tert-butoxide. The amount of base used relative to one equivalent of compound (2) or compound (2-1) can be 0.1 to 100 equivalents.

[0069] The reaction can be carried out in the presence of an additive. Examples of suitable additives include 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, or 4-(dimethylamino)pyridine. The amount of additive used relative to 1 equivalent of compound (2) or compound (2-1) can be 0.005 to 100 equivalents.

[0070] The reaction temperature can be set to any temperature from -78℃ to the reflux temperature of the mixture. Although the reaction time may vary depending on the concentration of the reaction matrix or the reaction temperature, it can usually be set arbitrarily within the range of 5 minutes to 100 hours.

[0071] (Preparation Example 2) The compound (1-1) of the present invention can be prepared, for example, by the preparation method described below.

[0072] [Chemical Formula 7]

[0073] [In the formula, Z] a1 Indicates C1-C6 alkyl, via R a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl or C1-C6 haloalkyl, G, R a R X R Y R 1 R 2 R 3 R 4 R 5 Z 2 The meanings of n4 and p are the same as described above. Compound (1-1) can be prepared by reacting compound (2-4) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0074] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0075] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-4).

[0076] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0077] (Preparation Example 3) The compounds (1-3) of the present invention can be prepared, for example, by the preparation methods described below.

[0078] [Chemical Formula 8]

[0079] [In the formula, G and J] 1 R X R Y R 1 R 2 R 3 R 4 R 5 Z 2 Z a1 The meanings of n4 and p are the same as described above. Compounds (1-3) can be prepared by reacting compounds (2-6) with compounds (D1) or compounds (E1) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0080] The amount of compound (D1) or compound (E1) used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-6).

[0081] Some of the compounds shown in compound (D1) are known compounds and are available from commercially available products. Other compounds shown in compound (D1) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0082] Some of the compounds shown in compound (E1) are known compounds and are available from commercially available products. Other compounds shown in compound (E1) can also be prepared using synthetic methods for generally known compounds as described in the literature.

[0083] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0084] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-6).

[0085] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0086] (Preparation Example 4) The compounds (1-4) of the present invention can be prepared, for example, by the preparation methods described below.

[0087] [Chemical Formula 9]

[0088] [In the formula, L represents a leaving group such as a chlorine atom, bromine atom, iodine atom, C1-C4 alkylsulfonyloxy (e.g., methanesulfonyloxy), halosulfonyloxy (e.g., fluorosulfonyloxy), C1-C4 haloalkylsulfonyloxy (e.g., trifluoromethanesulfonyloxy), or arylsulfonyloxy (e.g., p-toluenesulfonyloxy), Z] a2 Represents hydrogen atom, C1-C6 alkyl or C1-C6 haloalkyl, G, R X R Y R 1 R 2 R 3 R 4 R 5 Z 2 Z a1The meanings of n4 and p are the same as those mentioned above.

[0089] Compounds (1-4) can be prepared by reacting compounds (2-7) with compound (C) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0090] The amount of compound (C) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-7).

[0091] Some of the compounds shown in compound (C) are known compounds and are available from commercially available products. Other compounds shown in compound (C) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0092] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0093] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-7).

[0094] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0095] (Preparation Example 5) The compounds (1-5) of the present invention can be prepared, for example, by the following preparation method.

[0096] [Chemical Formula 10]

[0097] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 Z 2 Z a1 The meanings of n4 and p are the same as described above. Compounds (1-5) can be prepared by reacting compounds (2-8) with a dehydrating agent in a solvent or under solvent-free conditions.

[0098] The amount of dehydrating agent used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-8).

[0099] Examples of dehydrating agents include N-(triethylammonium sulfonyl)carbamate.

[0100] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0101] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0102] (Preparation Example 6) The compounds (1-6) of the present invention can be prepared, for example, by the preparation methods described below.

[0103] [Chemical Formula 11]

[0104] [In the formula, A represents an oxygen atom or a sulfur atom, G, R...] X R Y R 1 R 2 R 3 R 4 R 5 Z 2 The meanings of n4 and p are the same as described above. Compounds (1-6) can be prepared by reacting compounds (2-6) with 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0105] The amount of 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-6).

[0106] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0107] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-6).

[0108] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0109] (Preparation Example 7) The compounds (1-7) of the present invention can be prepared, for example, by the preparation methods described below.

[0110] [Chemical Formula 12]

[0111] [In the formula, R] 102 Indicates C1-C6 alkyl or C1-C6 haloalkyl, A, G, L, RX R Y R 1 R 2 R 3 R 4 R 5 Z 2 The meanings of n4 and p are the same as described above. Compounds (1-7) can be prepared by reacting compounds (1-6) of the present invention with compound (F) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0112] The amount of compound (F) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-6).

[0113] Some of the compounds shown in compound (F) are known compounds and are available from commercially available products. Other compounds shown in compound (F) can also be prepared using synthetic methods for generally known compounds as described in the literature.

[0114] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0115] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-6).

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

[0117] (Preparation Example 8) The compounds (1-9) of the present invention can be prepared, for example, by the preparation methods described below.

[0118] [Chemical Formula 13]

[0119] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 R d Z 2 The meanings of n4 and p are the same as described above. Compounds (1-9) can be prepared by reacting compounds (1-8) with compounds (K) or their salts (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or without solvent, and, if appropriate, in the presence of a base, according to well-known methods described in the literature, such as those described in Synthesis, 2019, Vol. 51, pp. 530-537.

[0120] The amount of compound (K) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (1-8).

[0121] Some of the compounds shown in compound (K) are known compounds and are available from commercially available products. Other compounds shown in compound (K) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0122] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0123] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (1-8).

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

[0125] The compounds (1-8) of the present invention can be synthesized according to the method of Preparation Example 3.

[0126] (Preparation Example 9) The compounds (1-11) of the present invention can be prepared, for example, by the preparation methods described below.

[0127] [Chemical Formula 14]

[0128] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 R 102 R e R f Z 2 The meanings of n4 and p are the same as described above. Compounds (1-11) can be prepared by reacting compounds (2-9) with compounds (L) or their salts (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate, p-toluenesulfonate, etc.) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base.

[0129] The amount of compound (L) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-9).

[0130] Some of the compounds shown in compound (L) are known compounds and are available from commercially available products. Other compounds shown in compound (L) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0131] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0132] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of compound (2-9).

[0133] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0134] The compound (2) used in Preparation Example 1 can be prepared, for example, according to the preparation route (reaction path) shown in the following reaction formula 1.

[0135] [Reaction Formula 1] [Chemical Formula 15]

[0136] [In the formula, X represents a halogen atom, G, R X and R Y The meaning is the same as described above. Compound (2) can be obtained by reacting compound (2-A) with compound (A) in a solvent or in solvent-free conditions in the presence of a base and, if necessary, in the presence of either or both of a copper catalyst and an additive. Alternatively, compound (2) can also be obtained by reacting compound (2-A) with compound (A) in the presence of a base and, if necessary, in the presence of a palladium catalyst and a ligand.

[0137] Some of the compounds shown in compound (2-A) are known compounds and are available from commercially available products. Other compounds shown in compound (2-A) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0138] The amount of compound (A) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-A).

[0139] Some of the compounds shown in compound (A) are known compounds and are available from commercially available products. Other compounds shown in compound (A) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0140] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0141] The reaction can be carried out in the presence of a base. One example of a base that can be used is the base illustrated in Preparation Example 1. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-A).

[0142] This reaction can be carried out in the presence of a copper-based catalyst. Examples of usable copper-based catalysts include copper iodide (monovalent), copper trifluoromethanesulfonate (monovalent) benzene complex, or copper trifluoromethanesulfonate (monovalent) toluene complex. The amount of copper-based catalyst used relative to one equivalent of the compound (2-A) can be 0.001 to 50 equivalents.

[0143] The reaction can be carried out in the presence of an additive. Examples of suitable additives include N,N-dimethylglycine or 4-(dimethylamino)pyridine. The amount of additive used relative to one equivalent of the compound (2-A) can be 0.001 to 100 equivalents.

[0144] This reaction can be carried out in the presence of a palladium-based catalyst. Examples of suitable palladium-based catalysts include (π-cinnamyl)palladium chloride (2-valent) dimer or allylpalladium chloride (2-valent) dimer. The amount of palladium-based catalyst used relative to 1 equivalent of the compound (2-A) can be 0.001 to 50 equivalents.

[0145] The reaction can proceed in the presence of a ligand. Examples of usable ligands include 2-ditert-butylphospho-2',4',6'-triisopropylbiphenyl (i.e., tert-butyl-XPhos), tetramethyl-ditert-butylphospho-2',4',6'-triisopropylbiphenyl (i.e., tetramethyl-ditert-butyl-XPhos), 2-di(tert-butyl)phospho-2',4',6'-triisopropyl-3-methoxy-6-methylbiphenyl (i.e., RockPhos), or 2-(dicyclohexylphospho)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl (i.e., BrettPhos), etc. The amount of ligand used relative to one equivalent of the compound (2-A) can be 0.001 to 50 equivalents.

[0146] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0147] The compound (2-1) used in Preparation Example 1 can be prepared, for example, according to the preparation route (reaction path) shown in the following reaction formula 2.

[0148] [Reaction 2] [Chemical Formula 16]

[0149] [J 1 G, R X and R Y The meaning is the same as described 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 well-known methods described in the literature, such as those described in the Journal of Medicinal Chemistry [J.Med.Chem.] 1991, Vol. 34, p. 1630.

[0150] Alternatively, it can be obtained by reacting it with organic acid halides such as tervapotranole chloride or isobutyl chloroformate in the presence of a base as needed, according to the methods described in Tetrahedron Letters (2003, Vol. 44, p. 4819) and Journal of Medicinal Chemistry (1991, Vol. 34, p. 222).

[0151] Within the range of compound (2), R Y Compounds containing hydrogen atoms (2-2) can be prepared, for example, by following the reaction route (reaction path) shown below.

[0152] [Reaction 3] [Chemical Formula 17]

[0153] [In the formula, R] 101 Indicates C1 to C6 alkyl groups, G and R X The meaning is the same as described above. Step 1: Compound (2-B) is reacted with compound (B) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate, etc.) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base, to obtain compound (2-C).

[0154] Some of the compounds shown in compound (B) are known compounds and are available from commercially available products. Other compounds shown in compound (B) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0155] The amount of compound (B) or its salt used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-B).

[0156] Some of the compounds shown in compound (2-B) are known compounds described in Bioorganic & Medicinal Chemistry Letters, 2015, Vol. 25, p. 4481. In addition, the other compounds shown in compound (2-B) can also be synthesized in the same manner as the known compounds according to the methods described in the corresponding literature.

[0157] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0158] The reaction can be carried out in the presence of a base. One example of a base that can be used is the base illustrated in Preparation Example 1. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-B).

[0159] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0160] Step 2: React compound (2-C) with an oxidant in a solvent or under solvent-free conditions to obtain compound (2-2).

[0161] Potassium permanganate is an example of an oxidizing agent that can be used. The amount of oxidizing agent used relative to 1 equivalent of the compound (2-C) can be 0.1 to 100 equivalents.

[0162] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

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

[0164] Within the range of compound (2), R Y Compounds containing hydrogen atoms (2-2) can be prepared, for example, by following the reaction route (reaction path) shown below.

[0165] [Reaction 4] [Chemical Formula 18]

[0166] [In the formula, G and R] X The meaning is the same as described above. Step 1: Compound (2-D) and compound (B) are reacted under the same conditions as in step 1 of reaction formula 3 to obtain compound (2-E).

[0167] Some of the compounds shown in compound (2-D) are known compounds described in International Publication No. 2003 / 016275. In addition, other compounds shown in compound (2-D) can also be synthesized in the same manner as the known compounds according to the methods described in the corresponding documents.

[0168] Step 2: React compound (2-E) with carbon dioxide in a solvent or in the absence of a solvent, or in the presence of a base, to obtain compound (2-2).

[0169] Examples of usable bases include n-butyllithium. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-E).

[0170] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

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

[0172] The compounds (2-4) used in Preparation Example 2 can be prepared, for example, according to the preparation route (reaction path) shown in the following reaction formula 5.

[0173] [Reaction 5] [Chemical Formula 19]

[0174] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 R 101 Z 2 Z a1 The meanings of n4 and p are the same as described above. Step 1: Compound (2) or compound (2-1) is reacted with compound (3-1) under the same conditions as in Preparation Example 1 to obtain compound (2-12).

[0175] Some of the compounds shown in compound (3-1) are known compounds and are available from commercially available products. Other compounds shown in compound (3-1) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0176] Step 2: React compound (2-12) according to known methods in the literature, such as those described in The Journal of Organic Chemistry, 2006, Vol. 24, pp. 9045-9050, to obtain compound (2-3).

[0177] Step 3: React compound (2-3) with compound (H) according to a known method described in the literature, such as the method described in International Publication No. 2008 / 156721, to obtain compound (2-4).

[0178] Some of the compounds in the (H) range are known compounds, and some are available commercially. Other compounds can also be prepared using methods for synthesizing commonly known compounds as described in the literature.

[0179] The compounds (2-6) used in Preparation Example 3 can be prepared, for example, according to the preparation route (reaction path) shown in Reaction Formula 6 below.

[0180] [Reaction Formula 6] [Chemical Formula 20]

[0181] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 Z 2 The meanings of n4 and p are the same as described above. Step 1: Compound (2) or compound (2-1) is reacted with compound (3-2) under the same conditions as in Preparation Example 1 to obtain compound (2-5).

[0182] Some of the compounds shown in compound (3-2) are known compounds and are available from commercially available products. Other compounds shown in compound (3-2) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0183] Step 2: React compound (2-5) according to known methods in the literature, such as those described in International Publication No. 2009 / 082398, to obtain compound (2-6).

[0184] The compounds (2-7) used in Preparation Example 4 can be prepared, for example, according to the preparation route (reaction path) shown in Reaction Formula 7 below.

[0185] [Reaction Formula 7] [Chemical Formula 21]

[0186] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 Z 2 The meanings of n4 and p are the same as described above. Compounds (2-7) can be obtained by reacting compounds (2-5) according to well-known methods known in the literature, such as those described in International Publication No. 2011 / 109799.

[0187] The compounds (2-8) used in Preparation Example 5 can be prepared, for example, according to the preparation route (reaction path) shown in Reaction Formula 8 below.

[0188] [Reaction Equation 8] [Chemical Formula 22]

[0189] [In the formula, G and R] X R Y R 1 R 2 R 3 R 4 R 5 Z 2 Z a1 The meanings of n4 and p are the same as described above. Compounds (2-8) can be obtained by reacting compounds (2-3) with compound (J) according to well-known methods known in the literature, such as those described in International Publication No. 2008 / 016123.

[0190] Some of the compounds in the range (J) are known compounds, and some are available from commercially available products. Other compounds can also be prepared using synthetic methods for generally known compounds as described in the literature.

[0191] Compound (2-C) can be prepared, for example, according to the preparation route (reaction path) shown in the following reaction formula.

[0192] [Reaction Formula 9] [Chemical Formula 23]

[0193] [In the formula, G and R] X and R 101 The meaning is the same as described above. Step 1: Hydrolyze compound (2-B) in the presence of water and acid to obtain compound (2-F).

[0194] Examples of usable acids include hydrochloric acid and acetic acid. The amount of acid used relative to 1 equivalent of the compound (2-B) can be 0.1 to 100 equivalents.

[0195] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0196] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0197] Step 2: Compound (2-F) is reacted with compound (B) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate, etc.) under the same conditions as in step 1 of reaction formula 2 to obtain compound (2-C).

[0198] Compounds (2-9) can be prepared, for example, according to the preparation route (reaction path) shown in the following reaction formula.

[0199] [Reaction Formula 10] [Chemical Formula 24]

[0200] [G, R] X R Y R 1 R 2 R 3 R 4 R 5 R 102 Z 2 The meanings of n4 and p are the same as described above. Compounds (2-9) can be prepared by reacting compounds (1-10) of the present invention with an oxidant in a solvent or under solvent-free conditions.

[0201] Examples of usable oxidizing agents include hydrogen peroxide or m-chloroperbenzoic acid. The amount of oxidizing agent used relative to 1 equivalent of the compound (1-10) can be 0.1 to 100 equivalents.

[0202] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

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

[0204] The compounds (1-10) of the present invention can be synthesized according to the method of Preparation Example 7.

[0205] Compound (2-11) can be prepared, for example, according to the preparation route shown in reaction formula 11 below.

[0206] [Reaction Formula 11] [Chemical Formula 25]

[0207] [In the formula, R] 103 Indicates a hydrogen atom or a C1-C6 alkyl group, G 1a Indicates C1-C6 alkyl or C3-C6 cycloalkyl, L, X, R X R Y and R 101 The meaning is the same as described above. Step 1: React compound (2-10) with compound (F1) in a solvent or in the absence of a solvent, or in the presence of a base, to obtain compound (2-G).

[0208] Some of the compounds in the (F1) range are known compounds, and some are available from commercially available products. Other compounds can also be prepared using synthetic methods for generally known compounds as described in the literature.

[0209] The amount of compound (F1) used relative to 1 equivalent of compound (2-10) can be 0.5 to 50 equivalents.

[0210] If a solvent is used, the solvent only needs to be inactive to the reaction, for example, the solvent illustrated in Preparation Example 1.

[0211] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-10).

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

[0213] Compound (2-10) can be synthesized according to the method of reaction formula 1.

[0214] Step 2: Compound (2-G) is reacted with compound (G) in a solvent or in solvent-free conditions, in the presence of a base, and, if necessary, in the presence of a palladium catalyst and ligand, to obtain compound (2-H).

[0215] Some of the compounds in the (G) range are known compounds, and some are available commercially. Other compounds can also be prepared using methods for synthesizing commonly known compounds as described in the literature.

[0216] The amount of compound (G) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-G).

[0217] If a solvent is used, the solvent only needs to be inactive to the reaction, for example, the solvent illustrated in Preparation Example 1.

[0218] As a base that can be used in this reaction, for example, the base illustrated in Preparation Example 1 can be cited. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-G).

[0219] Palladium-based catalysts that can be used in this reaction include, for example, the palladium-based catalyst exemplified in reaction formula 1. The amount of palladium-based catalyst used relative to 1 equivalent of the compound (2-G) can be 0.001 to 50 equivalents.

[0220] As ligands that can be used in this reaction, examples include the ligands illustrated in reaction formula 1. The amount of ligand used relative to 1 equivalent of the compound (2-G) can be 0.001 to 50 equivalents.

[0221] The reaction temperature and reaction time are within the temperature and time ranges described in Preparation Example 1.

[0222] Step 3: React compound (2-H) in a solvent or in solvent-free conditions and, if appropriate, in the presence of a base to obtain compound (2-11).

[0223] As a base that can be used in this reaction, the base illustrated in Preparation Example 1 can be cited as an example. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-H).

[0224] The reaction temperature and reaction time are within the temperature and time ranges described in Preparation Example 1.

[0225] Compound (2-N) can be prepared, for example, according to the preparation route (reaction path) shown in reaction formula 12 below.

[0226] [Reaction 12] [Chemical Formula 26]

[0227] [In the formula, R] 104 It represents di(C1-C6 alkyl)amino, pyrrolid-1-yl, piperidin-1-yl, or morpholin-1-yl, G, J 1 R X and R 101 The meaning is the same as described above. Step 1: Hydrolyze compound (2-J) in a solvent or in solvent-free conditions, and in the presence of acid, to obtain compound (2-K).

[0228] Some of the compounds shown in compound (2-J) are known compounds and are available from commercially available products. Other compounds shown in compound (2-J) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0229] Examples of acids that can be used include hydrochloric acid, acetic acid, formic acid, and sulfuric acid. The amount of acid used relative to 1 equivalent of the compound (2-J) can be 0.1 to 100 equivalents.

[0230] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0231] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0232] Step 2: React compound (2-K) with compound (K1) in a solvent or under solvent-free conditions to obtain compound (2-L).

[0233] Some of the compounds shown in compound (K1) are known compounds and are available from commercially available products. Other compounds shown in compound (K1) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0234] The amount of compound (K1) used can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-K).

[0235] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0236] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0237] Step 3: React compound (2-L) with compound (M) in a solvent or in solvent-free conditions, or in the presence of a base, to obtain compound (2-M).

[0238] Some of the compounds shown in compound (M) are known compounds and are available from commercially available products. Other compounds shown in compound (M) can also be prepared using synthetic methods for commonly known compounds as described in the literature.

[0239] The amount of compound (M) can be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-L).

[0240] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0241] As a base that can be used in this reaction, the base illustrated in Preparation Example 1 can be cited as an example. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-L).

[0242] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0243] Step 4: React compound (2-M) with compound (B) or its salt (e.g., hydrochloride, hydrobromide, hydroiodide, sulfate, trifluoroacetate, oxalate or p-toluenesulfonate, etc.) in a solvent or in solvent-free conditions, and, if appropriate, in the presence of an acid, to obtain compound (2-N).

[0244] The amount of compound (B) or its salt used may be 0.5 to 50 equivalents relative to 1 equivalent of compound (2-M).

[0245] If a solvent is used, the solvent only needs to be inactive to the reaction. For example, the solvent exemplified in Preparation Example 1 can be used as such a solvent.

[0246] As an acid that can be used in this reaction, for example, the acid exemplified in step 1 of reaction formula 12 can be given. The amount of base used can be 0.1 to 100 equivalents relative to 1 equivalent of the compound (2-M).

[0247] The reaction temperature and reaction time can be arbitrarily set within the temperature and time range described in Preparation Example 1.

[0248] The compounds of this invention can generally be used as fungicides and mold killers in agriculture and horticulture to combat various diseases caused by fungi, oomycetes, mucor, ascomycetes, basidiomycetes, deuteromycetes, bacteria or viruses.

[0249] "Pathogens" refer to microorganisms that cause plant diseases. The following microorganisms can be cited as examples, but are not limited to them.

[0250] Taphrina spp. (e.g., Taphrina deformans, T. pruni, etc.), Pneumocystis spp., Geotrichum spp., Candida spp. (e.g., Candida albicans, C. sorbosa, etc.), Pichia spp. (e.g., Pichia kluyveri, etc.), Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp. (e.g., Cercospora apii, C. asparagi, C. beticola, C. capsici, C. carotae, C. kaki, C. kikuchii, C. zonata, etc.), Cercosporidium spp., Cladosporium spp. (e.g., Cladosporium colocasiae, C. cucumerinum, C. variabile, etc.), Davidiella spp., Didymosporium spp., Heterosporium spp. (e.g., Heterosporium allii), Mycosphaerella spp. (e.g., Mycosphaerella arachidis, M. berkeleyi, M. cerasella, M. fijiensis, M. fragariae, M. graminicola, M. nawae, M. pinodes, M. pomi, M. zingiberis), Mycovellosiella spp. (e.g., Mycovellosiella fulva, M. nattrassii), Paracercospora spp. (e.g., Paracercospora egenula), Phaeosariopsis spp., Phaeoramularia spp., Pseudocercospora spp. (e.g., Pseudocercospora abelmoschi, P. fuligena, P. vitis), Pseudocercosporella spp. (such as Pseudocercosporellacapsellae, etc.), Ramichloridium spp., Ramularia spp., Septogloeum spp., Septoriaspp.(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., Ascochytapisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria Nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp. (e.g., Pyrenophora graminea, P. teres, etc.), Setosphaeria spp.(e.g., Setosphaeria turcica, etc.), Stemphylium spp. (e.g., Stemphylium botryosum, S. lycopersici, S. solani, S. vesicarium, etc.), Fusicladium spp., Venturia spp. (e.g., Venturia carpophila, V. Inaequalis, V. nashicola, V. pirina, etc.), Didymella spp. (e.g., Didymella bryoniae, D. fabae, etc.), Hendersonia spp., Phona spp. (e.g., Phona erratica var. mikan, P. exigua var. exigua, P. wasabiae, etc.), Pyrenochaeta spp. (e.g., Pyrenochaeta lycopersici, etc.), Stagonospora spp. (e.g., Stagonospora sacchari, etc.), Botryosphaeria spp. (e.g., Botryosphaeria berengeriana f. sp. piricola, B. dothidea, etc.), Dothiorella spp., Fusicoccum spp., Guignardia spp., Lasiodiplodia spp. (such as Lasiodiplodiatheobromae, etc.), Macrophoma spp., Macrophomina spp., Neofusicoccum spp., Phyllosticta spp. (such as Phyllosticta zingiberis, etc.), Schizothyrium spp. (such as Schizothyrium pomi, etc.), Acrospermum spp., Leptosphaerulina spp., Aspergillusspp., Penicillium spp. (such as Penicillium digitatum, P. italicum, P. sclerotigenum, etc.), Microsporum spp., Trichophyton spp. (such as Trichophyton mentagrophytes, T. rubrum, etc.), Histoplasma spp., Blumeria spp. (such as Blumeria graminis f.*Erysiphe* spp. (e.g., *Erysiphe betae*, *E. cichoracearum*, *Ec. var. cichoracearum*, *E. heraclei*, *E. pisi*, etc.), *Golovinomyces* spp. (e.g., *Golovinomyces cichoracearum* var. *latisporus*, etc.), *Leveillula* spp. (e.g., *Leveillulataurica*, etc.), *Microsphaera* spp., *Oidium* spp. (e.g., *Oidium neolycopersici*, etc.), *Phyllactinia* spp. (e.g., *Phyllactinia kakicola*, *P. mali*, *P. moricola*, etc.), *Podosphaera* spp. (e.g., *Podosphaera fusca*, *P. leucotricha*, *P. pannosa*, *P. tridactyla* var. *tridactyla*, *P. xanthii*, etc.), *Sphaerotheca* spp. (such as Sphaerothecaaphanis var. aphanis, S. fuliginea, etc.), Uncinula spp. (such as Uncinula necator, U. n. var. necator, etc.), Uncinuliella spp. (such as Uncinuliella simulans var. simulans, Us var. tandae, etc.), Blumeriella spp. (such as Blumeriella jaapii, etc.), Cylindrosporium spp., Diplocarpon spp. (such as Diplocarpon mali, D. mespili, D. rosae, etc.), Gloeosporium spp. (such as Gloeosporium minus, etc.), Marssonina spp., Tapesia spp. (such as Tapesia acuformis, T. yallundae, etc.), Lachnum spp., Scleromitrula spp., Botryotinia spp. (such as Botryotinia fuckeliana, etc.), Botrytis spp. (e.g., Botrytis allii, B.byssoidea, B.).cinerea, B. elliptica, B. fabae, B. squamosa etc.), Ciborinia spp., Grovesinia spp., Monilia mumecola, Monilinia spp. heterodoxa etc.), Claviceps spp. spp.、Cylindrocladium spp.、Fusarium spp. (e.g. Fusarium arthrosporioides, F. crookwellense, F. culmorum, F. cuneirostrum, F. oxysporum, F. of sp. adzukicola, F. of sp. allii, F. of sp. asparagi, Fo f. sp. batatas, F. o. f. sp. cepae, F. of sp. colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp. lagenariae, Fof. sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. ofsp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sfsp. cucurbitae, F. sf sp. eumartii, F. sf sp. glycines, F. sf sp. pisi, F. sf sp. Radicicola, F. virguliforme, etc.), Gibberella spp. (e.g. Gibberellaavenacea, G. baccata, G. fujikuroi, G. zeae, etc.), Haematonectria spp., Nectria spp., Ophionectria spp., Caldariomyces spp., Myrothecium spp., Trichothecium spp., Verticillium spp. (e.g. Verticillium albo-atrum, V. dahliae, V. longisporum, etc.), Ceratocystis spp. (e.g. Ceratocystis ficicola, C. fimbriata, etc.), Thielaviopsis spp. (e.g. Thielaviopsis basicola, etc.), Adisciso spp., Monochaetia spp., Pestalotiaspp. (e.g. Pestalotia eriobotrifolia, etc.), Pestalotiopsis spp. (e.g. Pestalotiopsis funerea, P. longiseta, P. neglecta, P. theae, etc.), Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp. (e.g. Rosellinia necatrix etc.)、Monographellaspp.(eg Monographella nivalis etc.)、Ophiostoma spp.*Cryphonectria* spp. (e.g., *Cryphonectria parasitica*), *Diaporthe* spp. (e.g., *Diaporthe citri*, *D. kyushuensis*, *D. nomurai*, *D. tanakae*), *Diaporthopsis* spp., *Phomopsis* spp. (e.g., *Phomopsis asparagi*, *P. fukushii*, *P. obscurans*, *P. vexans*), *Cryptosporella* spp., *Discula* spp. (e.g., *Discula theae-sinensis*), *Gnomonia* spp., *Coniella* spp., *Coryneum* spp., *Greeneria* spp., *Melanconis* spp., *Cytospora* spp., *Leucostoma* spp., *Valsa* spp. (e.g., *Valsa ceratosperma*), *Tubakia* spp., *Monosporascus* spp., Clasterosporium spp., Gaeumannomyces spp. (e.g., Gaeumannomyces graminis), Magnaporthe spp. (e.g., Magnaporthe grisea), Pyricularia spp. (e.g., Pyriculariazingiberis), Monilochaetes infuscans, Colletotrichum spp. (e.g., Colletotrichumacutatum, C. capsici, C. cereale, C. destructivum, C. fragariae, C. lindemuthianum, C. nigrum, C. orbiculare, C. spinaciae), Glomerella spp. (e.g., Glomerella cingulata), Khuskia oryzae, Phylachora spp. (e.g., Phylchorapomigena), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum, etc.), Epicoccum spp.Fungi belonging to the phylum Ascomycota, including Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola), Phaeocytostroma spp., Phialophora spp. (e.g., Phialophora gregata), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis), Sarocladium spp., Coleophoma spp., and Helicoceras oryzae. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g., Helicobasidium longisporum, etc.), Coleosporium spp. (e.g., Coleosporium plectranthi, etc.), Cronartium spp., Phakopora spp. (e.g., Phakopora 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.), Pucciniaspp. (such as 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.), Uromycesspp. (such as Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromycesviciae-fabae var. viciae-fabae, etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (such as Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. (such as Blastospora smilacis, etc.), Uredo spp., Sphacelothecaspp., Urocystis spp., Sporisorium spp. (such as Sporisorium scitamineum, etc.), Ustilagospp. (such as Ustilago maydis, U. Nuda, etc.), Entyloma spp., Exobasidium spp. (e.g., Exobasidium reticulatum, E. vexans, etc.), Microstroma spp., Tilletia spp. (e.g., Tilletia caries, T. controversa, T. laevis, etc.), Itersonilia spp. (e.g., Itersonilia perplexans, etc.), Cryptocococcus 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 (e.g., *Cepivorum*, *Typhula* spp., *Typhula incarnata*, *T. ishikariensis* var.)Fungi belonging to the phylum Basidiomycota, including *Ishikariensis*, *Athelia* spp. (e.g., *Athelia rolfsii*), *Ceratobasidium* spp. (e.g., *Ceratobasidium cornigerum*), *Ceratorhiza* spp., *Rhizoctonia* spp. (e.g., *Rhizoctonia solani*), *Thanatephorus* spp. (e.g., *Thanatephorus cucumeris*), *Laetisaria* spp., *Waitea* spp., *Fomitiporia* spp., *Ganoderma* spp., *Chondrostereum purpureum*, and *Phanerochaete* spp.; fungi belonging to the phylum Chitridiomycota, including *Olpidium* spp.; and fungi belonging to the phylum Blastodactylomycota, including *Physoderma* spp. Fungi belonging to the subphylum Mucoromycotina, such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis), and Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer). Protist organisms belonging to the subphylum Cercozoa, such as Plasmodiophora spp. (e.g., Plasmodiophora brassicae) and Spongospora subterranea f. sp. Subterranea. Aphanomyces spp. (e.g., Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (e.g., Albugo macrospora, A. wasabiae, etc.), Bremia spp. (e.g., Bremia lactucae, etc.), Hyloperonospora spp., Peronosclerospora spp., Peronosporaspp. (e.g., Peronospora alliariae-wasabi, P. chrysanthemi-coronarii, P. destructor, P. farinosa f. sp.).spinach, P. manshurica, P. parasitica, P. spasra etc.), Plasmopara spp. (eg Plasmopara halstedii, P. nivea, P. viticola etc.), Pseudoperonospora spp. melonis、P. sojae、P. adzukicola、P. aphanideratum、P. buismaniae、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. volutum, etc.) are oomycetes of the Heterokontophyta. Clavibacter spp. (e.g. Clavibactermichiganensis subsp. michiganensis, etc.), Curtobacterium spp., Leifsonia spp. (e.g. Leifsonia xyli subsp. xyli, etc.), Streptomyces spp.Gram-positive bacteria of the phylum Actinobacteria (e.g., Streptomyces ipomoeae, etc.), Gram-positive bacteria of the phylum Firmicutes (e.g., Clostridium sp.), and Gram-positive bacteria of the phylum Tenericulates (e.g., Phytoplasma). Rhizobium spp. (such as Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderiaspp. (such as Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B.plantarii, etc.), Acidovorax spp. (such as Acidovorax avenae subsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (such as Ralstoniasolanacearum, etc.), Xanthomonas spp. (such as Xanthomonas albilineans, X. arboricolapv. pruni, X. axonopodis pv. vitians, glycines, X. c. pv. mangiferaeindicae, X. c. pv.nigromaculans, X. c. pv. vesicatoria, X. citri subsp. citri, savastanoi pv. glycinea, P. syringae, P. s.pv. actinidiae, P. s. pv. eriobotryae, P. s. pv. helianthi, P. s. pv.lachrymans, P. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s.pv. spinaciae, P. s.Gram-negative bacteria belonging to the phylum Proteobacteria, including *P. syringae*, *P. s. pv. theae*, *P. viridiflava*, *Rhizobacter spp.*, *Brenneria spp.* (e.g., *Brenneria nigrifluens*), *Dickeya spp.* (e.g., *Dickeya dianthicola*, *D. zeae*), *Erwinia spp.* (e.g., *Erwinia amylovora*, *E. rhapontici*), *Pantoea spp.*, and *Pectobacterium spp.* (e.g., *Pectobacterium atrosepticum*, *P. carotovorum*, *P. wasabiae*).

[0251] Specific examples of plant diseases caused by the infection and proliferation of these pathogens can be cited below, but are not limited to these.

[0252] Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), beet brown spot (Cercospora beticola), bell pepper leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown spot (Mycosphaerella arachidis), cherry brown hole disease (Cylindrosporium leaf spot (Mycosphaerella cerasella, Blumeriella jaapii), black tobacco disease (Mycosphaerella fijiensis), yellow tobacco disease (Mycosphaerella musicola), wheat leaf blight (Mycosphaerella sp.). graminicola), persimmon circular leaf spot (Mycosphaerella nawae), pea brown spot (Mycosphaerella pinodes), mycohe leaf blight (Mycosphaerella zingiberis), tomato leaf mold (Mycovellosiella fulva), eggplant black mold (Mycovellosiella nattrassii), tomato black mold (Pseudocercospora fuligena), grape brown spot (Pseudocercospora vitis), cabbage white spot (Pseudocercosporella capsellae), chrysanthemum black spot (Septoria chrysanthemella), chrysanthemum brown spot (Leaf)blight (Septoriaobesa), grape black vine disease Anthracnose (Elsinoe ampelina), aralia elata anthracnose Spot (Elsinoe araliae), citrus anthracnose Scab (Elsinoe fawcettii), pea brown spot Leaf spot (Ascochyta pisi), cucumber brown spot Corynespora leaf spot (Corynespora cassiicola), rose twig blight Stem canker (Leptosphaeria coniothyrium), wheat hull blight Glume blotch (Leptosphaeria nodorum), rose black spot Leaf spot (Alternaria alternata), cabbage black spot Alternaria leaf spot (Alternaria brassicae), carrot black leaf blight (Alternaria dauci), pear black spot (Alternaria kikuchiana), apple blotch Alternaria mali, onion black spot Alternaria leaf Leaf spot (Alternaria porri), Target spot (Bipolaris sorghicola) of sorghum, Southern leaf blight (Cochliobolus heterostrophus) of maize, Brown spot (Cochliobolus miyabeanus) of rice, Tip blight (Pleospora herbarum) of garlic, Stripe (Pyrenophora graminea) of barley, Net blotch (Pyrenophora teres) of barley, Leaf blight (Setosphaeria turcica) of sorghum, Northern leaf blight (Setosphaeri aturcica) of maize, Leaf spot (Stemphylium botryosum) of asparagus, Scab (Venturia carpophila) of Rosaceae Chlorideae, Scab (Venturia inaequalis) of apple, Scab (Venturia carpophila) of pear.The following diseases are listed: * *Nashiicola* (a type of cucurbit), *Gummy stem blight* (Didymella bryoniae), *Leaf spot* (Phoma exigua var. exigua), *Streak* (Phoma wasabiae), *Ring rot* (Botryosphaeria berengeriana f. sp. piricola) (Rosaceae), *Soft rot* (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.) (Kiwifruit), *Common green mold* (Penicillium digitatum), *Blue mold* (Penicillium italicum) (Kiwifruit), *Powdery mildew* (various diseases), *Blumeria graminis f. sp. hordei* (barley), *Blumeria graminis f. sp. tritici* (wheat), and *Erysiphe betae* (Cucumber). Powdery mildew of various plants, including: *Erysiphe cichoracearum*, *Erysiphe taurica*, *Sphaerotheca fuliginea*, *Erysiphe heraclei*, *Erysiphe pisi*, *Erysiphe taurica*, *Erysiphe cichoracearum*, *Erysiphe taurica*, *Erysiphe heraclei*, *Erysiphe pisi*, *Erysiphe taurica ... Powdery mildew of papaya / melon (Podosphaera)Powdery mildew of various plants including: xanthii (a type of plant), strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), watermelon / melon powdery mildew (Sphaerotheca fuliginea), grape powdery mildew (Uncinula necator, U. n. var. necator), apple brown spot (Diplocarpon mali), rose black spot (Diplocarpon rosae), onion gray rot (Gray mold neck rot, Botrytis allii), gray mold, Botrytis blight (Botrytis cinerea), leek white spot and leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), broad bean red spot (Botrytis cinerea, B. elliptica, B. fabae), Rosaceae brown rot (Monilinia fructicola, M. fructigena, M. laxa), and apple blossom blight (Monilinia fructicola, M. fructigena, M. laxa). (The text lists various diseases and their diseases, including:) *Sclerotinia homoeocarpa* (dollar spot), *Sclerotinia rot* (Cottonyrot), *Sclerotinia rot* (Sclerotinia sclerotiorum), *Villosiclava virens* (false smut), *Calonectria ilicicola* (black root rot of soybean), *Fusarium crookwellense* (*Fusarium culmorum*, *Gibberella avenacea*, *G. zeae*, *Monographella nivalis* (red mold of wheat), *Fusarium culmorum* (red mold of barley), *Fusarium oxysporum* (*Fusarium culmorum*, *Gibberella avenacea*, *G. zeae* (red mold of barley), *Fusarium oxysporum* (dry rot of konjac) (*Fusarium oxysporum*, *F. solani* f. sp. pisi, *F. sf...* (brown rot of yam)). sp.Radicicola), Red bean wilt (Fusarium wilt f.sp. adzukicola), Shallot dry rot (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Sweet potato vine rot (Fusarium oxysporum f. sp. batatas, F. solani), Taro dry rot (Fusarium oxysporum f. sp. colocasiae), Cabbage / Komatsuna yellow wilt (Fusarium oxysporum f. sp. conglutinans), Rubber Panama disease (Fusarium oxysporum f. sp. cubense), Strawberry yellow wilt (Fusarium oxysporum f. sp. fragariae), Lettuce root rot (Fusarium oxysporum f. sp. fragariae). *Fusarium wilt* sp. *lacucae*, watermelon vine rot (*Fusarium oxysporum* f. sp. *lagenariae*, *F. of sp. *niveum*), tomato wilt (*Fusarium oxysporum* f. sp. *lycopersici*), melon vine rot (*Fusarium oxysporum* f. sp. *melonis*), radish yellow wilt (*Fusarium oxysporum* f. sp. *raphani*), spinach wilt (*Fusarium oxysporum* f. sp. *spinaciae*), soybean acute succumbing disease (*Fusarium solani* f. sp. *Glycines*, *Fusarium virguliforme*), rice seedling disease "Bakanae" (*Gibberella fujikuroi*), radish black spot (*Verticillium albo-atrum*, *V.*). dahliae), tomatoes, eggplants, and wilt of Verticillium (a type of wilt disease).Wilt (Verticillium dahliae), fig plant blight (Ceratocystis canker (Ceratocystis ficicola)), sweet potato black rot (Ceratocystis fimbriata), tea ring spot (Gray blight (Pestalotiopsis longiseta, P. theae)), chestnut stem blight (Endothia canker (Cryphonectria parasitica)), citrus black spot (Melanose (Diaporthe citri)), asparagus stem blight (Stemblight (Phomopsis asparagi)), pear stem blight (Phomopsis canker (Phomopsis fukushii)), eggplant brown spot (Phomopsis vexans), tea anthracnose (Discula theae-sinensis), apple rot (Valsa canker (Valsa ceratosperma)), rice blast (Blast (Magnaporthe grisea)), strawberry anthracnose (Crown) Anthracnose of various plants, including: apple (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), cherry (Colletotrichum acutatum, Glomerella cingulata), plum (Colletotrichum acutatum), grape (Colletotrichum acutatum, Glomerella cingulata), chrysanthemum (Colletotrichum acutatum), sword bean (Colletotrichum lindemuthianum), cucurbit (Colletotrichum orbiculare), yam (Glomerella cingulata), and chestnut (Glomerella cingulata). cingulata), persimmon anthracnose (Glomerella)(The text lists various rust diseases and their associated diseases, which are not directly related to the preceding sentence.) chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisorium scitamineum), corn smut (Ustilago maydis), barley naked head disease (Ustilago nuda), tea net blister blight (Exobasidium reticulatum), tea blister blight (Exobasidium vexans), white mold (Stem rot), southern blight (Athelia rolfsii), chrysanthemum stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), ginger rot (Rhizoctonia solani), cabbage seedling damping-off (Rhizoctonia solani), clover damping-off (Rhizoctonia solani). Lettuce leaf blight (Rhizoctonia solani), lettuce leaf rot (Bottom rot), lettuce leaf rot (Brown patch), LargePatch (Rhizoctonia solani), Sheath blight (Thanatephorus cucumeris) of rice, Root rot (Thanatephorus cucumeris) of beet, Leaf blight (Thanatephorus cucumeris) of beet, Black mold (Rhizopus rot (Rhizopus stolonifer var. stolonifer) of fig, Clubroot (Plasmodiophora brassicae) of rapeseed, Black root rot (Aphanomyces cochlioides) of beet, White rust (Albugo macrospora) of rapeseed, Downy mildew on various crops, Downy mildew (Bremia lactucae) of lettuce, Downy mildew (Peronosporachrysanthemi-coronarii) of chrysanthemum, Downy mildew (Peronospora destructor) of onion / Allium family, Downy mildew (Peronospora farinosa f. sp.) of spinach. Downy mildew of various plants including: spinaciae, soybean (Peronospora manshurica), rapeseed (Peronospora parasitica), rose (Peronospora sparsa), sunflower (Plasmopara halstedii), clover (Plasmopara nivea), grape (Plasmopara viticola), cucurbit (Pseudoperonospora cubensis), aralia root blight (Phytophthora cactorum), watermelon brown rot (Phytophthora capsici), pumpkin blight (Phytophthora capsici), green pepper blight (Phytophthora capsici), watermelon blight (Phytophthora cryptogea), and tomato / potato blight (Late blight). blight (Phytophthorainfestans), fig blight, white powderyPhytophthora palmivora, Leafblight (Phytophthora porri) of the Allium family, Phytophthora root and stem rot (Phytophthora sojae) of soybean, Phytophthora stem rot (Phytophthora vignae f.sp. adzukicola) of red bean, Damping-off (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum) of spinach, Root rot (Pythium aristosporum) of konjac, Browning root rot (Pythium arrhenomanes, P. graminicola) of corn, Damping-off (Pythium buismaniae, P. myriotylum) of cabbage seedlings, Root rot (Pythium myriotylum) of ginger, Root rot of ginger. rot (Pythium myriotylum, P. ultimum var. ultimum), carrot blotted root rot (Pythium sulcatum), tomato ulcer (Bacterial canker (Clavibacter michiganensis subsp. michiganensis)), potato anthracnose (Scab (Streptomyces spp.)), rose root gall (Rhizobium radiobacter)), sorghum stripe (Bacterial stripe (Burkholderia andropogonis)), onion rot (Soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici)), rice wilt (Bacterial grain rot (Burkholderia gladioli, B. glumae)), watermelon fruit blotch (Bacterial fruit blotch (Acidovorax avenae subsp.)). citrulli), Bacterial leaf blight of AmorphophallusBlight (Acidovorax konjaci), bacterial wilt (Ralstonia solanacearum), peach leaf spot (Xanthomonas arboricola pv. pruni, Pseudomonas syringa pv. syringae, Brenneria nigrifluens), plum leaf spot (Xanthomonas arboricola pv. pruni), lettuce leaf spot (Xanthomonas axonopodis pv. vitians), rapeseed black rot (Xanthomonas campestris pv. campestris), soybean yellow leaf disease (Xanthomonas campestris pv. glycines), burdock black spot (Xanthomonas campestris) The following fungi are associated with citrus diseases: * *xanthomonas campestris* pv. *nigromaculans*, *xanthomonas campestris* pv. *vesicatoria*, *xanthomonas citri* subsp. *citri*, *xanthomonas citri*, *xanthomonas cichorii*, *xanthomonas marginalis* pv. *marginalis*, *xanthomonas viridiflava*, *xanthomonas cichorii*, *xanthomonas marginalis* pv. *marginalis*, *xanthomonas viridiflava*, *xanthomonas syringae* pv. *syringae*, *xanthomonas viridiflava*, *xanthomonas syringae* pv. *actinidiae*, and *xanthomonas syringae* pv. *canker*. eriobotryae), Bacterial bacterial disease of CucurbitaceaeSpot (Pseudomonassyringae pv. lachrymans), black spot disease (Pseudomonassyringae pv. maculicola), canker disease (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), shoot blight disease (Pseudomonassyringae pv. theae), soft rot disease (Dickeya sp., Pectobacterium carotovorum), fire blight disease (Erwinia amylovora), soft rot disease (Pectobacterium carotovorum), and soft rot disease (Pectobacterium carotovorum).

[0253] The development of pesticides for controlling diseases in agricultural and horticultural crops has yielded significant progress, with a wide variety of agents available for practical use to date. However, due to the long-term use of these agents, in recent years there has been an increase in cases where pathogens have acquired resistance, making them difficult to control using existing fungicides. Furthermore, some existing pesticides are highly toxic, and the long-term environmental residues of certain pesticides, which disrupt the ecosystem, are also becoming increasingly apparent. In this context, the compounds of the present invention exhibit excellent control activity against many pathogens and are highly safe for target crops. In addition, the compounds of the present invention can also provide sufficient control against pathogens that have acquired resistance to existing fungicides. Moreover, the compounds of the present invention do not cause phytotoxicity to target crops, have virtually no adverse effects on mammals, fish, and beneficial insects, and exhibit low residue and low environmental impact.

[0254] In addition to being used as fungicides for agricultural and horticultural purposes, the compounds of the present invention can also be used as: medical antibacterial agents and animal antibacterial agents as antifungal agents or endoparasite control agents; antibacterial / antifungal agents for wood, paper pulp, adhesives, coatings, fibers and leather, etc.; and industrial fungicides for cooling water systems in manufacturing plants, etc.

[0255] Regarding the target pathogens of medical or veterinary antimicrobial agents, examples include dermatophytes such as *Trichophyton rubrum* and *Trichophyton mentagrophytes*, *Candida albicans*, *Aspergillus fumigatus*, *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*, but these are not limited to these.

[0256] Regarding the target strains of antibacterial and antifungal agents, examples include wood-decaying fungi such as Tyromyces palustris and Coriolus versicolor, and material-degrading microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopusoryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladiumvirens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria, but these are not limited to.

[0257] Regarding the target strains of industrial bactericides, examples include slime-forming fungi such as Sphaerotilis natans and Zoogloea ramigera, but these are not the only ones that can be mentioned.

[0258] In addition to being used as fungicides for agricultural and horticultural purposes, the compounds of this invention can also be used as agents to control internal parasites in livestock, poultry, or pets.

[0259] The following are specific examples of internal parasites that are the targets of control efforts, but they are not the only ones.

[0260] *Haemonchus*, *Trichostrongylus*, *Ostertagia*, *Nematodirus*, *Cooperia*, *Ascaris*, *Bunostomum*, *Oesophagostomum*, *Chabertia*, *Trichuris*, *Storongylus*, *Trichonema*, *Dictyocaulus*, *Capillaria*, *Heterak* Nematodes including *Ascaris*, *Toxocara*, *Ascaridia*, *Oxyuris*, *Ancylostoma*, *Uncinaria*, *Toxascaris*, and *Parascaris*; filariae nematodes including *Wuchereria*, *Brugia*, *Onchoceca*, *Dirofilaria*, and *Loa*; nematodes of the family Dracunculidae including *Deacunculus*; and *Dipylidium*. Tapeworms including *Taenia taeniaeformis*, *Taenia solium*, *Taenia saginata*, *Hymenolepis diminuta*, *Moniezia benedeni*, *Diphyllobothrium latum*, *Diphyllobothrium erinacei*, *Echinococcus granulosus*, and *Echinococcus multilocularis*; liver leeches (*Fasciola hepatica*, *F. gigantica*), lung flukes (*Paragonimus westermanii*), *Schistosoma bruski*, and *Eurytrema pancreaticum* (*E. pancreaticum*).Trematodes such as *Schistosoma coelomaticum*, *Clonorchis sinensis*, *Schistosoma japonicum*, *Schistosoma haematobium*, and *Schistosoma mansoni*; Eimeria spp. such as *Eimeria tenella*, *Eimeria acervulina*, *Eimeria brunetti*, *Eimeria maxima*, *Eimeria necatrix*, *Eimeria bovis*, and *Eimeria ovinoidalis*; and Trichomonas cruzi, Leishmania spp., *Plasmodium spp.*, and Babesia spp. This includes spp., Trichomonadidae spp., Histomanas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica, Theileria spp., etc.

[0261] In addition to being used as fungicides for agricultural and horticultural purposes, the compounds of this invention can also be used as antifungal agents.

[0262] The following are specific examples of the target pathogens of antifungal agents, but they are not the only ones.

[0263] Trichophyton rubrum and Trichophyton mentagrophytes, Candida albicans, Aspergillus fumigatus, Cryptococcus neoformas, etc.

[0264] When the compounds of this invention are applied as plant disease and pest control agents, they can generally be mixed with a suitable solid or liquid carrier, and surfactants, penetrants, spreading agents, thickeners, antifreeze agents, binders, anti-caking agents, disintegrants, or decomposition inhibitors can be added as needed to prepare any dosage form such as a liquid concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granule, water-soluble granule, suspension concentrate, concentrated emulsion, suspension emulsion, microemulsion, dustable powder, granule, or gel for practical use. Furthermore, from the viewpoint of labor-saving and improved safety, the above-mentioned dosage forms can also be packaged in water-soluble packaging.

[0265] Examples of solid carriers include: natural minerals such as quartz, kaolin, pyrophyllite, diatomite, talc, bentonite, acid clay, palygorskite, zeolite, or diatomite; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, or potassium chloride; synthetic silicic acid; or synthetic silicates.

[0266] Examples of liquid carriers include: alcohols such as ethylene glycol, propylene glycol, or isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, or alkylnaphthalene; ethers such as butyl glycol monoethyl ether (trademark name Cellosolve); ketones such as cyclohexanone; esters such as γ-butyrolactone; amides such as N-methylpyrrolidone or N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, or castor oil; or water; and so on. These solid and liquid carriers can be used alone or in combination of two or more.

[0267] Examples of surfactants include: nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene styrene phenyl ethers, polyoxyethylene polyoxypropylene block copolymers, fatty acid polyoxyethylene esters, fatty acid sorbitol esters, or fatty acid polyoxyethylene sorbitol esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonates, alkyl naphthalene sulfonates, salts of formaldehyde condensates of naphthalene sulfonic acid, salts of formaldehyde condensates of alkyl naphthalene sulfonic acid, sulfates or phosphates of polyoxyethylene alkyl aryl ethers, sulfates or phosphates of polyoxyethylene styrene phenyl ethers, polycarboxylate salts or polystyrene sulfonates; cationic surfactants such as alkylamine salts or alkyl quaternary ammonium salts; or amphoteric surfactants of amino acid type or amino intrasalt type; and so on.

[0268] The content of these surfactants is not particularly limited, but is generally preferred to be in the range of 0.05 to 20 parts by weight relative to 100 parts by weight of the formulation of the present invention. In addition, these surfactants can be used alone or in combination of two or more.

[0269] When the compounds of the present invention are used as pesticides, they can be mixed with other types of herbicides, insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers or soil conditioners as needed during formulation or dispensing.

[0270] In particular, by mixing with other pesticides or plant hormones, one can expect lower costs due to reduced dosage, synergistic effects of the mixed agents resulting in broad-spectrum fungicides and insecticides, or even greater pest control. When mixed, it can also be combined with multiple well-known pesticides simultaneously.

[0271] In one embodiment, the types of pesticides that may be mixed with the compounds of the present invention include, for example, those described in the 18th edition of The Pesticide Manual, 2018. Specific common names of these compounds may be exemplified below. However, the pesticides that may be mixed are not limited to these.

[0272] 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, bequinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, BENZAMACRIL, benzamorf, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture The following fungicides are listed: mixture, boscalid, bromoconazole, bupirimate, buthiobate, butylamine, calcium polysulfide, captafol, captan, carbamorph, carbendazim, carboxin, carpropamid, carvone, chesthunt mixture, chinomethionat, chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, and climbazole.Copper acetate, basic copper carbonate, copper hydroxide, copper naphthenate, copper oleate, basic copper chloride, copper sulfate, basic copper sulfate, copper zinc chromate Zincchromate, Coumoxystrobin, Cresol, Cufraneb, Cuprobam, Cyazofamid, Cycloafuramid, Cycycloheximide, Cyflufenamid, Cymoxanil, Cypendazole, Cyproconazole, Cyprodinil, Cyprofuram, Dazomet, Debacarb, Decafentin, Dehydroacetic acid acid, dichlobentiazox, dichlofluanid, dichloronaphthoquinone, dichlorophen, dichlozoline, diclobutrazol, diclomezine, dicloran, diethofencarb, difenoconazole, diflumetorim, dimethirimol Dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6, diocton, dinosulfon, dinoterbon, diphenylamine, dipymetitrone, dipyrithioneDisulfiram, ditalimfos, dithianon, DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyqu In), chlorpyrifos (etridiazole), famoxadone, fenamidone, fenaminosulf, fenaminstrobin, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, benzyl Fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, fludioxonil, flufenoxystrobin, fluindapyr, flumetover, flumorph, fluopicolide, and fipronil. luopimomide, fluopyram, fluoroimide, fluotrimazole, fluoxapiprolin, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutianil, flutriafol, fluxapyroxad, folpetAluminum fosetyl-aluminate, fthalide, furaidazole, furaxyl, furamepyr, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodin, griseofulvin, guazatine, halacrinate, six Chlorobenzene, hexaconazole, hexylthiofos, 8-hydroxyquinoline sulfate, hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarbamate b) Ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamid, Bayer isoflurane, isoprothiolane, isopyrazam, isovaledione, kasugamycin Kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamid, maneb, mebenil, mecarbinzid, mefentrifluconazole, mepanipyrim, mepronil, meptyldinocap, metalaxylMetalaxyl-M, metam, metazoxolon, metconazole, metasulfocarb, methfuroxam, metyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, mancozeb Sodium (nabam), naftifine, natamycin, organonitrogen compounds (bis(dimethyl dithiocarbamate) nickel; bis(dimethyl dithiocarbamate) nickel), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxine copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins, polyoxorim, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride, propiconazole, propinebProquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, piracarbolid, piraclostrobin, pirametostrobin, piraoxystrobin, pyrapropoyne, piraziflumid Pyridachlometyl, pyridinitril, pyriofenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, sedaxane, silthiofam, simeconazole, sodium bicarbonate Hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate, thiophanate-methyl, thiram, tiadinilThioxymid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide, trihlamide, trilopyricarb, tricyclazole, triridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate Naphthenate, zinc sulfate, zinc bromide, zinc thiram, zoxamide, shiitake mycelium extract, and shiitake fruiting body extract, etc.

[0273] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acynonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, bacillus thuringiensis thuringiensis), bendicarb, benfluthrin, benfuracarb, bensultap, benzoximate, BENZPYRIMOXAN, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, broflanilide, bromopropylate, buprofezin, but... ocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionat, chlorantraniliprole, CHLORETHXYFOS, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chlorobezilate, chloroprallethrin, chlorpyrifos, chlorpyrifos-methyl, chromafenozideClofentezine, Clothianidin, Cyanophos, Cyantraniliprole, Cycloaniliprole, Cycloprothrin, Cyenopyrafen, Cyetpyrafen, Cyflumetofen, Cyfluthrin, Cyhalodiamide, Cyhalothrin, Cyhexatine Cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diacloden, diafenthiuron, diazinon, dichlorvos, dicloomezotiazine, dicofol, dienochlor, diflovidazin, diflubenzur On, dimefluthrin, dimethoate, dimethylvinphos, dimpropyridaz, dinotefuran, diofenolan, disulfoton, DNOC, d-tetramethrin, emamectin-benzoate, empenthrin, endosulfan, EPN, epsil (List of insect names follows, which are not translated as they are not part of the main text.)Fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, fometoquin, flonicamid, fluacrypyrim, fluazuron, flubendiamide, fluchlorodiniliprole, flucyclo xuron), flucythrinate, flufenerim, flufenoxuron, flufenprox, flufiprole, fluhexafon, flumethrin, flupentiofenox, flupyradifurone, flupyrimin, fluralaner, fluvalinate, fluxametamide, and more. Fonophos, Formetate, Formothion, Furathiocarb, Gamma-Cyhalothrin, Halfenprox, Halofenozide, Heptafluthrin, Hexaflumuron, Hexythiazox, Hydamethylnon, Imidacloprid, Imiprothrin, Indazole azapyroxamet, imidacloprid, indoxacarb MP, isocycloseram, isofenphos, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, lepimectin, lufenuron, malathionMeperfluthrin, Metaflumizone, Metalcarb, Metaldehyde, Metacrifos, Methamidophos, Methidathion, Methotridium, Metoprene, Methoxychlor, Methoxyfenozide, Methyl bromide bromide, metofluthrin, milkemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone Phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos-methyl, PRAZIQUANTEL, profenofos, profluthrin, propaphos, propargite, prothiofos, protrifenbute, pyflubumide, pymetrozine, piraclofos, pirafluprole, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyrimidifen, pyriprole, pyriproxyfenResmethrin, rotenone, silafluofen, spidoxamat, spintoram, spinosad, spirodiclofen, spiromesifen, spiropidion, spirotetramat, spirromesifen, sulfotep, sulfoxaflor, sulprofos, tau-fluvalinate, tebfenozide, tebufenpyrad, teflubenzuron, tefluthorin, terbufos, tetrachlorantraniliprole, tetrachlor The following are listed as examples of insecticides: chlorvinphos, tetramethrin, tetramethylfluthrin, tetraliprole, thiacloprid, thiamethoxam, thiocyclam, thiodicarb, thiofanox, thiometon, tolfenpyrad, tralomethrin, transfluthrin, triazamate, triazuron, trichlorfon, triflumezopyrim, triflumuron, tyclopyrazoflor, vamidothion, and zeta-cypermethrin.

[0274] Parasite medications: esfenvalerate, fenpropathrin, fenvalerate, cypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin, zeta-cypermethrin, acetamiprid. amiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, dicifenophos diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos, ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenobucarb, carbofuran, and fenobucarb. Afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner, tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectinMaduramycin, Milbemycin, Milbemycin Oxime, Moxicillin, Selamectin, Indoxacarb, Amitraz, Bistrifluron, Spinosad, Albendazole, Atovaquone, Bithionol, Cambendazole, Carnidazole, Chloroquine, Clazuril, Clorsulon, Closantel, Coumaphos, Dichlorophen, Diethylcarbamazine, Diminazene, Dinitolmide, Dithiazanine iodide, emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mefloquine hydrochloride, melarsamine hydrochloride, metronidazole, metyridine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipic acid The following are listed: adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, and tetramisole hydrochloride.Thiabendazole and triclabendazole, etc.

[0275] Antifungal agents: ketoconazole and miconazole nitrate, etc.

[0276] Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid acid), danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate Phosphate), acetylisovaleryl tylosin, tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Trichoderma, and other fungi.

[0277] The dosage of the compound of the present invention varies depending on the application occasion, application period, application method or cultivated crop, but the average effective ingredient dosage per hectare (ha) is usually 0.005 to 50 kg, preferably 0.01 to 1 kg.

[0278] The following describes formulation examples using compounds of the present invention. However, the formulation examples of the present invention are not limited to these. Furthermore, in the following formulation examples, "parts" refers to parts by weight.

[0279] [Wettable powder] 0.1 to 80 parts of the compound of the present invention Solid carrier 5–98.9 parts 1 to 10 parts of surfactant Other 0-5 portions Other examples include anti-caking agents or anti-decomposition agents.

[0280] [Emulsion] 0.1 to 30 parts of the compound of the present invention 45-95 parts of liquid carrier Surfactant 4.9-15 parts Other 0-10 portions Other examples include spreading agents or anti-decomposition agents.

[0281] [Suspension agent] 0.1 to 70 parts of the compound of the present invention Liquid carrier 15–98.89 parts 1-12 parts of surfactant Others: 0.01 to 30 portions Other examples include antifreeze or thickeners.

[0282] [Water-dispersible granules] 0.1 to 90 parts of the compound of the present invention Solid carrier 0–98.9 parts 1-20 parts of surfactant Other 0-10 portions Other examples include adhesives or decomposition inhibitors.

[0283] [Liquid] 0.01 to 70 parts of the compound of the present invention Liquid carrier 20–99.99 parts Other 0-10 portions Other examples include antifreeze or spreading agents.

[0284] [Granules] 0.01 to 80 parts of the compound of the present invention Solid carrier 10–99.99 parts Other 0-10 portions Other examples include adhesives or decomposition inhibitors.

[0285] 〔powder〕 0.01 to 30 parts of the compound of the present invention Solid carrier 65–99.99 parts Other 0-5 portions Other examples include anti-drift agents or anti-decomposition agents.

[0286] When using, the above preparation is diluted with water by 1 to 10,000 times, preferably 100 to 10,000 times, or it can be dispersed without dilution.

[0287] The following are specific examples of formulations of fungicides for agricultural and horticultural use that use the compounds of the present invention as active ingredients; however, the formulations of the present invention are not limited to these examples, including the compounds of the present invention. Furthermore, in the following formulation examples, "parts" refers to parts by weight.

[0288] [Formulation Example 1] Emulsion Compound No. 1-001 of the present invention, 20 parts 55 parts of methylnaphthalene 20 parts of cyclohexanone SORPOL 26805 copies (A mixture of nonionic and anionic surfactants; trade name manufactured by Toho Chemical Industry Co., Ltd.) The above ingredients are mixed evenly to form an emulsion. When using, the emulsion is diluted with water 50 to 20,000 times and distributed at an average effective dose of 0.005 to 50 kg per hectare.

[0289] [Formulation Example 2] Wettable Powder Compound No. 1-001 of the present invention, 25 parts 66 portions of pyrophyllite SORPOL 50394 copies (Anionic surfactant; trade name manufactured by Toho Chemical Industry Co., Ltd.) Carplex #80D 3 servings (Silica; a product name manufactured by Shionogi Pharmaceutical Co., Ltd.) 2 parts of calcium lignosulfonate The above-mentioned ingredients are uniformly mixed and pulverized to prepare a wettable powder. When using, the wettable powder is diluted with water 50 to 20,000 times and distributed at an average effective dose of 0.005 to 50 kg per hectare.

[0290] [Formulation Example 3] Powder Compound No. 1-001 of the present invention, 3 parts Carplex #80D 0.5 pieces (Silica; a product name manufactured by Shionogi Pharmaceutical Co., Ltd.) 95 portions of kaolin 1.5 parts diisopropyl phosphate The above ingredients are uniformly mixed and pulverized to form a powder. When using, the powder is spread at an average dosage of 0.005–50 kg of active ingredient per hectare.

[0291] [Formulation Example 4] Granules Compound No. 1-0015 of the present invention 30 parts of bentonite 64 parts of talc 1 part calcium lignosulfonate The above ingredients are uniformly mixed and pulverized, a small amount of water is added and stirred, granulated using an extrusion granulator, and then dried to form granules. When using, the granules are distributed at an average dosage of 0.005–50 kg of active ingredient per hectare.

[0292] [Formulation Example 5] Suspension Concentrate Compound No. 1-001 of the present invention, 25 parts SORPOL 3353 (5 copies) (Nonionic surfactant; trade name manufactured by Toho Chemical Industry Co., Ltd.) RUNOX 1000C 0.5 servings (Anionic surfactant; trade name manufactured by Toho Chemical Industry Co., Ltd.) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts 10 parts of propylene glycol 58.9 parts water The above-mentioned components, except for the active ingredient (the compound of the present invention), are uniformly dissolved, and then the compound of the present invention is added and stirred thoroughly. The mixture is then wet-milled using a sand mill to obtain a flow agent. In use, the flow agent is diluted with water 50 to 20,000 times and distributed at an average effective ingredient dosage of 0.005 to 50 kg per hectare.

[0293] [Formulation Example 6] Granular wettable powder 75 parts of compound No. 1-001 of the present invention HITENOL NE-15 5 servings (Anionic surfactant; trade name manufactured by Daiichi Kogyo Pharmaceutical Co., Ltd.) VANILLEX N10 copies (Anionic surfactant; product name manufactured by Nippon Paper Corporation) Carplex #80D (10 servings) (Silica; a product name manufactured by Shionogi Pharmaceutical Co., Ltd.) The above ingredients are uniformly mixed and finely pulverized. A small amount of water is added and stirred. The mixture is then granulated using an extrusion granulator and dried to produce a dry flow agent. When using, it is diluted with water 50 to 20,000 times and distributed at an average effective dose of 0.005 to 50 kg per hectare.

[0294] Methods of applying the compounds of the present invention may include foliar dispersal, soil treatment, or seed disinfection, but general methods commonly used by those skilled in the art are also effective.

[0295] 〔Summarize〕 In view of the above, the embodiments of the present invention relate to the following [1] to

[78] .

[0296] [1] A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 27]

[0297] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 28]

[0298] G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, Regarding G 1 The relationships between them, when m5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. R X Indicates C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1、R X -2, R X -3 or RX -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 29]

[0299] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1 They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5 Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-29 or E-30. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-30 each represent the structure shown in the following structural formulas. [Chemical Formula 30]

[0300] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: a They are the same or different from each other. Regarding Z a The relationships between them, when v4 represents integers 2, 3, or 4, are as follows: a They are the same or different from each other. Z b Indicates C1 to C6 alkyl groups. R a This indicates hydroxyl, cyano, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino, phenylcarbonylamino, -ОR g -C(О)R g -NR h SO2R j Or Q-1, Q-1 represents the structure shown in the following structural formula. [Chemical Formula 31]

[0301] Q 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. Regarding Q 1 The relationships between them, when w5 represents integers 2, 3, 4, or 5, are as follows: 1 They are the same or different from each other. R b Indicates a hydrogen atom or a C1-C6 alkyl group. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R d Indicates amino, hydroxyamino, C1-C6 alkylamino, C3-C6 alkylamino, C4-C6 alkylamino.10 Cycloalkylamino, di(C1-C6)amino, pyrrolid-1-yl, morpholin-1-yl, or piperidin-1-yl R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy R f This represents a hydrogen atom, hydroxyl group, C1-C6 alkyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, C1-C6 alkylamino carbonyl group, di(C1-C6 alkyl)amino carbonyl group, C1-C6 alkyl sulfonyl group, or C1-C6 haloalkyl sulfonyl group. R g Indicates Q-1, R h Indicates a hydrogen atom or a C1-C6 alkyl group. R j Indicates C1 to C6 alkyl groups. m5 represents the integers 0, 1, 2, 3, 4, or 5. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v4 represents the integer 0, 1, 2, 3, or 4. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1. w5 represents the integers 0, 1, 2, 3, 4, or 5.

[0302] [2] According to the pyrazole compound or its salt described in [1] above, wherein, G 1 Indicates a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group. R X Indicates C1-C6 alkyl, R X -1 or R X -2, R Y Represents a hydrogen atom. R 1 Represents a hydrogen atom. R 2 Represents a hydrogen atom. R 3 Represents a hydrogen atom. R 4 Represents a hydrogen atom. R 5 Represents a hydrogen atom. Z1 Indicates E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z 2 Indicates C1 to C6 alkoxy groups. Z a This indicates hydroxyl, mercapto, halogen atom, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Q 1 Represents halogen atoms, R b Indicates C1 to C6 alkyl groups. R c Indicates C1 to C6 alkyl groups. R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl or C1-C6 alkoxy R h Indicates C1 to C6 alkyl groups. m5 represents the integer 0 or 1. n4 represents the integer 0 or 1. u5 represents the integer 0. u4 represents the integer 0. p represents the integer 1. v4 represents the integer 0. w5 represents the integer 0 or 1.

[0303] [3] According to the pyrazole compound or its salt described in [2] above, wherein, Z 1 Indicates E-3, E-4, E-5, E-6, E-8, E-9, E-12, E-13 or E-29.

[0304] [4] The pyrazole compound or its salt according to [3] above, wherein, Z a Indicates C1-C6 alkyl, via R aSubstituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, -C(=NOR) b )R c -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl R a It represents C1-C6 alkoxy or C1-C6 alkylthio.

[0305] [5] The pyrazole compound or its salt according to [3] or [4] above, wherein, Z 1 This indicates E-3, E-4, E-5, or E-29.

[0306] [6] The pyrazole compound or its salt according to [1] above, wherein, G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl.

[0307] [7] The pyrazole compound or its salt according to [1] above, wherein, G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy.

[0308] [8] The pyrazole compound or its salt according to [1] above, wherein, G 1 It represents hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy.

[0309] [9] The pyrazole compound or its salt according to [1] above, wherein, G 1 It represents nitro, cyano, halogen atom, C1-C6 alkyl or C1-C6 haloalkyl.

[0310]

[10] The pyrazole compound or its salt according to [1] above, wherein, G 1 Indicates a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group. m5 represents the integer 0 or 1.

[0311]

[11] A pyrazole compound or a salt thereof according to any one of [3] to

[10] above, wherein G 1 It indicates C1-C6 alkyl or C1-C6 haloalkyl.

[0312]

[12] According to the pyrazole compound or salt thereof described in

[11] above, wherein G 1 It represents C1 to C6 alkyl groups.

[0313]

[13] According to the pyrazole compound or salt thereof described in

[11] above, wherein G 1 It represents C1 to C6 haloalkyl groups.

[0314]

[14] According to the pyrazole compound or salt thereof described in

[11] above, wherein G 1 This represents a halogen atom.

[0315]

[15] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0316]

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

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

[0317]

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

[0318]

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

[17] above, wherein R X Indicates C1-C6 alkyl, R X -1 or R X -2.

[0319]

[19] A pyrazole compound or a salt thereof according to any one of [1] to

[17] above, wherein R X It represents C1 to C6 alkyl groups.

[0320]

[20] According to the pyrazole compound or its salt described in

[19] above, wherein R X It represents tert-butyl.

[0321]

[21] A pyrazole compound or a salt thereof according to any one of [1] to

[17] above, wherein, R X R represents X -1 or R X -2, u5 represents the integer 0. u4 represents the integer 0.

[0322] 〔twenty two〕 According to the pyrazole compound or its salt described in

[21] above, wherein R X R represents X -1.

[0323] 〔twenty three〕 According to the pyrazole compound or its salt described in

[21] above, wherein R X R represents X -2.

[0324]

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

[23] above, wherein R Y It represents a hydrogen atom, a halogen atom, or a C1 to C6 alkyl group.

[0325]

[25] A pyrazole compound or a salt thereof according to any one of [1] to

[23] above, wherein R Y It represents a hydrogen atom.

[0326]

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

[23] above, wherein R Y This represents a halogen atom.

[0327]

[27] A pyrazole compound or a salt thereof according to any one of [1] to

[23] above, wherein R Y It represents C1 to C6 alkyl groups.

[0328]

[28] The pyrazole compound or its salt according to [1] and [6] to

[27] above, wherein, R 1 Represents a hydrogen atom. R 2 Represents a hydrogen atom. R 3 Represents a hydrogen atom. R 4 Represents a hydrogen atom. R 5 Represents a hydrogen atom. p represents the integer 1.

[0329]

[29] The pyrazole compound or its salt according to any one of [1] and [6] to

[28] above, wherein, Z 1 Indicates E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z 2Indicates C1 to C6 alkoxy groups. n4 represents the integer 0 or 1.

[0330]

[30] A pyrazole compound or a salt thereof according to any one of [1] to

[28] above, wherein Z 1 Indicates E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-12, E-13, E-21 or E-29.

[0331]

[31] The pyrazole compound or its salt according to

[30] above, wherein Z 1 Indicates E-3, E-4, E-5, E-6, E-8, E-9, E-12, E-13 or E-29.

[0332]

[32] According to the pyrazole compound or its salt described in

[30] above, wherein Z 1 Indicates E-3, E-4, E-5, E-6, E-12 or E-29.

[0333]

[33] According to the pyrazole compound or its salt described in

[30] above, wherein Z 1 This indicates E-3, E-4, E-5, or E-29.

[0334]

[34] The pyrazole compound or its salt according to

[30] above, wherein Z 1 It indicates E-3, E-4, or E-5.

[0335]

[35] The pyrazole compound or its salt according to

[30] above, wherein Z 1 It indicates E-3.

[0336]

[36] The pyrazole compound or its salt according to

[30] above, wherein Z 1 It indicates E-4.

[0337]

[37] The pyrazole compound or its salt according to

[30] above, wherein Z 1 It indicates E-5.

[0338]

[38] The pyrazole compound or its salt according to

[30] above, wherein Z 1 It indicates E-29.

[0339]

[39] A pyrazole compound or a salt thereof according to any one of [1] to

[38] above, wherein, Z a Indicates C1-C6 alkyl, via R a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, -C(=NOR) b )Rc -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl R b Indicates C1 to C6 alkyl groups. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl or C1-C6 alkoxy R f It represents hydrogen atom, C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylamino carbonyl, and di(C1-C6 alkyl)amino carbonyl.

[0340]

[40] The pyrazole compound or its salt according to

[39] above, wherein R e Represents hydrogen atoms, C1-C6 alkyl groups, or C3-C6 alkyl groups. 10 cycloalkyl, R f It represents hydrogen atom, C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylamino carbonyl, and di(C1-C6 alkyl)amino carbonyl.

[0341]

[41] According to the pyrazole compound or its salt described in

[39] above, wherein, R e Indicates a hydrogen atom or a C1-C6 alkyl group. R f It represents a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 alkyl carbonyl group.

[0342]

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

[39] above, wherein, Z a Indicates C1-C6 alkyl, via R a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl or C1-C6 haloalkyl, R a It represents C1-C6 alkoxy or C1-C6 alkylthio.

[0343]

[43] A pyrazole compound or a salt thereof according to any one of [1] to

[42] above, wherein, Z a Indicates C1-C6 alkyl, via R a Substituted C1-C6 alkyl or C1-C6 haloalkyl, Ra It represents C1-C6 alkoxy or C1-C6 alkylthio.

[0344]

[44] The pyrazole compound or its salt according to

[43] above, wherein, Z a Indicates C1-C6 alkyl or via R a The C1-C6 alkyl groups have been replaced. R a It represents C1 to C6 alkoxy groups.

[0345]

[45] A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein Z a It indicates C1-C6 alkyl or C1-C6 haloalkyl.

[0346]

[46] A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein Z a It represents C1 to C6 alkyl groups.

[0347]

[47] A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein Z a It represents C1 to C6 haloalkyl groups.

[0348]

[48] ​​A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein, Z a Indicates via R a The C1-C6 alkyl groups have been replaced. R a It represents C1 to C6 alkoxy groups.

[0349]

[49] A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein, Z 1 Indicates E-3, Z a Indicates C1-C6 alkyl or via R a The C1-C6 alkyl groups have been replaced. R a It represents C1 to C6 alkoxy groups.

[0350]

[50] A pyrazole compound or a salt thereof according to any one of [1] to

[39] above, wherein Z a This indicates -C(=NOR) b )R c -NR e R f , phenyl, pyrrolidone-1-yl, morpholino-1-yl or piperidin-1-yl.

[0351]

[51] A pyrazole compound or a salt thereof according to any one of [1] to

[38] above, wherein, Z a This indicates -C(=NOR) b )R c or -C(O)R d , R b Indicates C1 to C6 alkyl groups. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R e Indicates a hydrogen atom or a C1-C6 alkyl group. R f It represents a hydrogen atom or a C1 to C6 alkyl group.

[0352]

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

[41] above, wherein R a This indicates C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino, phenylcarbonylamino, -ОR g -C(О)R g -NR h SO2R j Or Q-1.

[0353]

[53] A pyrazole compound or a salt thereof according to any one of [1] to

[41] above, wherein R a It represents C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino or phenylcarbonylamino.

[0354]

[54] A pyrazole compound or a salt thereof according to any one of [1] to

[41] above, wherein, R a Represents C1-C6 alkoxy, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino, -ОR g -C(О)R g or -NR h SO2R j , R g Indicates Q-1, Q 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. R h Indicates C1 to C6 alkyl groups. R jIndicates C1 to C6 alkyl groups. w5 represents the integer 0 or 1.

[0355]

[55] The pyrazole compound or its salt according to

[54] above, wherein, Q 1 Represents halogen atoms, w5 represents the integer 1.

[0356]

[56] The pyrazole compound or its salt as described in

[54] above, wherein w5 represents the integer 0.

[0357]

[57] According to the pyrazole compound or its salt described in [1] to

[41] above, wherein R a It represents C1-C6 alkoxy or C1-C6 alkylcarbonylamino.

[0358]

[58] According to the pyrazole compound or its salt described in [1] to

[41] above, wherein R a It represents C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl.

[0359]

[59] According to the pyrazole compound or its salt described in [1] to

[41] above, wherein R a It represents C1-C6 alkylthio, C1-C6 alkylsulfinyl, or C1-C6 alkylsulfonyl.

[0360]

[60] The pyrazole compound or its salt according to [1] to

[41] above, wherein, R a Indicate -ОR g -C(О)R g -NR h SO2R j Or Q-1, Q 1 Represents halogen atoms, w5 represents the integer 0 or 1.

[0361]

[61] A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 32]

[0362] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 33]

[0363] G 1This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, Regarding G 1 The relationships between them, when m5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. R X Indicates C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1、R X -2, R X -3 or R X -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 34]

[0364] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1 They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-4 or E-5. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-5 each represent the structure shown in the following structural formulas. [Chemical Formula 35]

[0365] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylcarbonyl or C1-C6 alkoxycarbonyl, Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: a They are the same or different from each other. R a Indicates cyano or C1-C6 alkoxy. m5 represents the integers 0, 1, 2, 3, 4, or 5 respectively. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1.

[0366]

[62] According to the pyrazole compound or its salt described in

[62] above, wherein, G 1 Indicates C1-C6 alkyl or C1-C6 haloalkyl. R XIndicates C1 to C6 alkyl groups. R Y Represents a hydrogen atom. R 1 Represents a hydrogen atom. R 2 Represents a hydrogen atom. R 3 Represents a hydrogen atom. R 4 Represents a hydrogen atom. R 5 Represents a hydrogen atom. Z 1 Indicates E-2 to E-4 or E-5. Z 2 Indicates C1 to C6 alkoxy groups. Z a Indicates hydroxyl, mercapto, C1-C6 alkyl, or R-terminated. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 alkylthio, R a Indicates C1 to C6 alkoxy groups. m5 represents the integer 1. n4 represents the integer 0. p represents the integer 1. v2 represents the integer 1. v1 represents the integer 1.

[0367]

[63] A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 36]

[0368] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 37]

[0369] G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, Regarding G 1 The relationships between them, when m5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. R X Indicates C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1、R X -2, R X -3 or R X -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 38]

[0370] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1 They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5 Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-4 or E-5. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-5 each represent the structure shown in the following structural formulas. [Chemical Formula 39]

[0371] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylcarbonyl or C1-C6 alkoxycarbonyl, Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: a They are the same or different from each other. R a Indicates cyano or C1-C6 alkoxy. m5 represents the integers 0, 1, 2, 3, 4, or 5 respectively. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1.

[0372]

[64] The pyrazole compound or its salt according to

[63] above, wherein, G 1 Indicates C1-C6 alkyl or C1-C6 haloalkyl. R X Indicates C1 to C6 alkyl groups. 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 4Represents a hydrogen atom. R 5 Represents a hydrogen atom. Z 1 Indicates E-2 to E-4 or E-5. Z 2 Indicates C1 to C6 alkoxy groups. Z a Indicates hydroxyl, mercapto, C1-C6 alkyl, or R-terminated. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy or C1-C6 alkylthio, R a Indicates C1 to C6 alkoxy groups. m5 represents the integer 1. n4 represents the integer 0. p represents the integer 1. v2 represents the integer 1.

[0373]

[65] A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 40]

[0374] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 41]

[0375] G 1 This indicates hydroxyl, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl group. 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, di(C1-C6 alkyl)amino, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, C3-C 10 Cycloalkylaminocarbonyl or di(C1-C6 alkyl)aminocarbonyl, Regarding G 1 The relationships between them, when m5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. R X Indicates C1-C6 alkyl, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, benzyl, R X -1、R X -2, R X -3 or RX -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 42]

[0376] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1 They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5 Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-26 or E-27. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-27 each represent the structure shown in the following structural formulas. [Chemical Formula 43]

[0377] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: a They are the same or different from each other. Regarding Z a The relationships between them, when v4 represents integers 2, 3, or 4, are as follows: a They are the same or different from each other. Z b Indicates C1 to C6 alkyl groups. R a This indicates hydroxyl, cyano, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, or C1-C6 alkylcarbonylamino. R b Indicates a hydrogen atom or a C1-C6 alkyl group. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R d Indicates amino, C1-C6 alkylamino, C3-C6 alkylamino, C4-C6 alkylamino. 10 Cycloalkylamino, di(C1-C6)amino, pyrrolid-1-yl, morpholin-1-yl, or piperidin-1-yl R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy R f This represents a hydrogen atom, C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkylamino carbonyl, di(C1-C6 alkyl)amino carbonyl, or C1-C6 alkyl sulfonyl. m5 represents the integers 0, 1, 2, 3, 4, or 5 respectively. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v4 represents the integer 0, 1, 2, 3, or 4. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1.

[0378]

[66] The pyrazole compound or its salt according to

[65] above, wherein, G 1 Indicates a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group. R X Indicates C1 to C6 alkyl groups. R Y Represents a hydrogen atom. R 1 Represents a hydrogen atom. R 2 Represents a hydrogen atom. R 3 Represents a hydrogen atom. R 4 Represents a hydrogen atom. R 5 Represents a hydrogen atom. Z 1 Indicates E-2~E-4, E-5, E-7, E-9~E-13, E-16~E-19, E-21, E-24~E-26 or E-27, Z 2 Indicates C1 to C6 alkoxy groups. Z a This indicates hydroxyl, mercapto, halogen atom, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, -C(=NOR) b )R c -C(O)R d -NR e R f pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl R a This indicates a hydroxyl group, a C1-C6 alkoxy group, or a C1-C6 alkyl carbonyl group. R b Indicates C1 to C6 alkyl groups. R c Indicates C1 to C6 alkyl groups. R eRepresents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl or C1-C6 alkoxy R f This represents a hydrogen atom, C1-C6 alkyl, C1-C6 alkyl carbonyl, C1-C6 alkoxy carbonyl, di(C1-C6 alkyl)amino carbonyl, or C1-C6 alkyl sulfonyl. m5 represents the integer 1. n4 represents the integer 0. p represents the integer 1. v4 represents the integer 0.

[0379]

[67] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0380]

[68] A pyrazole compound or a salt thereof according to any one of [1] to

[66] above, wherein n4 represents the integer 0.

[0381]

[69] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0382]

[70] A pyrazole compound or a salt thereof according to any one of [1] to

[66] above, wherein v2 represents the integer 0.

[0383]

[71] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0384]

[72] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0385]

[73] A pyrazole compound or a salt thereof according to any one of [1] to

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

[0386]

[74] A pesticide containing one or more of the pyrazole compounds and their salts selected from any one of [1] to

[73] above as active ingredients.

[0387]

[75] A bactericide containing one or more of the pyrazole compounds and their salts selected from any one of [1] to

[73] above as active ingredients.

[0388]

[76] An agricultural and horticultural fungicide containing one or more of the pyrazole compounds and their salts selected from any one of [1] to

[73] above as active ingredients.

[0389]

[77] An antifungal agent containing one or more of the pyrazole compounds and their salts selected from any one of [1] to

[73] above as active ingredients.

[0390]

[78] An endoparasite control agent containing one or more of the pyrazole compounds and their salts selected from any one of [1] to

[73] above as active ingredients.

[0391] [Example] Hereinafter, examples of the synthesis and experimental examples of the compounds of the present invention will be described as embodiments to provide a more detailed description of the present invention, but the present invention is not limited to these embodiments.

[0392] As the medium-pressure fractionating liquid chromatograph described in the synthesis example, the medium-pressure fractionating device YFLC-Wprep (flow rate 18 ml / min, 40 μm silica gel column) manufactured by Yamazen Corporation was used.

[0393] In addition, regarding the proton nuclear magnetic resonance spectrum described below (hereinafter referred to as...) 1 The chemical shift values ​​on the 1H-NMR spectrum were obtained using Me4Si (tetramethylsilane) as a standard and measured at 300 MHz (JNM-ECX300 or JNM-ECP300; manufactured by JEOL) or 400 MHz (JNM-ECZ400S; manufactured by JEOL). It should be noted that... 1 The relevant markings for the chemical shift values ​​in H-NMR represent the following meanings.

[0394] s: single peak; d: double peak; dd: double double peak; t: triple peak; dt: double triple peak; q: quadruple peak; sep: seven peaks; m: multiple peaks; br: broad single peak.

[0395] [Synthesis example] Synthetic Example 1: Synthesis of 1-(tert-butyl)-N-(4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-013) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(((2,2,2-trifluoroacetylimineamidinium)oxy)carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 150 mg of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoic acid and 3 ml of dichloromethane, 92 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 49 mg of 2,2,2-trifluoro-N'-hydroxyacetylimine amidine, 49 mg of triethylamine, and 4 mg of 1-hydroxy-7-azabenzotriazole were added sequentially at room temperature, and the mixture was stirred for 16 hours at this temperature. After the reaction was complete, 3 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (3 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure to obtain 220 mg of the target compound as an oil.

[0396] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide A mixture of 220 mg of 1-(tert-butyl)-N-(4-(((2,2,2-trifluoroacetylimineamidinium)oxy)carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide obtained in step 1 and 3 ml of pyridine was stirred at 80 °C for 6 hours. After the reaction was complete, 1 mol / L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate (3 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to obtain 108 mg of the target substance as a white solid with a melting point of 125-127 °C.

[0397] Synthetic Example 2: Synthesis of 1-(tert-butyl)-N-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-003) To a mixed solution of 150 mg 1-(tert-butyl)-N-(4-(N'-hydroxycarbamoylimino)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 3 ml N,N-dimethylformamide, 171 mg potassium carbonate and 63 mg acetic anhydride were added at room temperature, and the mixture was stirred at 50 °C for 3 hours. After the reaction was complete, 6 ml of water was added to the reaction mixture, and the mixture was extracted with a mixture of n-hexane and ethyl acetate in a ratio of 1:2 (v / v; hereinafter the same) (5 ml × 1). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using a gradient of n-hexane and ethyl acetate (v / v from 9:1 to 1:9) as the eluent to obtain 111 mg of the target substance as a white solid with a melting point of 119–121 °C.

[0398] Synthetic Example 3: Synthesis of 1-(tert-butyl)-N-(4-(4-methylthiazolyl-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-011) To a mixed solution of 100 mg 1-(tert-butyl)-N-(4-aminothioformylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml N,N-dimethylformamide, 19 mg 1-chloropropane-2-one was added at room temperature, and the mixture was stirred at 60 °C for 20 hours. After the reaction was complete, 6 ml of water was added to the reaction mixture, and the mixture was extracted with a 1:1 mixture of n-hexane and ethyl acetate (3 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 1:9) as the eluent to obtain 111 mg of the target analyte as an oil.

[0399] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.76(d,J=8.1Hz,2H),7.40-7.27(m,2H),7.25-7.13(m,4H),7.08-7.01(m, 1H),6.85(s,1H),6.50-6.40(m,1H),3.66(q,J=6.7Hz,2H),2.83(t,J=6.9Hz,2H),2.98(s,3H),1.72(s,9H).

[0400] Synthetic Example 4: 1-(tert-butyl)-N-(4-(5-propyl-1,3,4-oxadiazol-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Synthesis of Compound No. 1-027) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(2-butyrylhydrazide-1-carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 100 mg of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoic acid and 3 ml of tetrahydrofuran, 68 mg of 1,1'-carbonyldiimidazole and 107 mg of butyrylhydrazine were added under ice-cold conditions, and the mixture was stirred at room temperature for 4 hours. After stirring, the reaction mixture was stirred at 60 °C for 4 hours, and then stirred under reflux for 2 hours. After the reaction was completed, 5 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (5 ml × 1 time). The resulting organic layer was washed with 1 mol / L hydrochloric acid, then dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 138 mg of the target substance as an oil.

[0401] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(5-propyl-1,3,4-oxadiazol-2-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 138 mg of 1-(tert-butyl)-N-(4-(2-butyrylhydrazide-1-carbonyl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 4 mL of 1,2-dichloroethane, 100 mg of methyl N-(triethylammonium sulfonyl)carbamate was added at room temperature, and the mixture was stirred under reflux for 3 hours. After stirring, 20 mg of methyl N-(triethylammonium sulfonyl)carbamate was added to the reaction mixture under reflux for 1 hour. After the reaction was complete, 5 mL of water was added to the reaction mixture, and the mixture was extracted with chloroform (3 mL × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to give 42 mg of the target substance as a white solid with a melting point of 83-86 °C.

[0402] Synthetic Example 5: Synthesis of 1-(tert-butyl)-N-(4-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-002) To a mixed solution of 100 mg 1-(tert-butyl)-N-(4-(N'-hydroxycarbamoylimino)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 2 ml tetrahydrofuran, 65 mg 1,1'-carbonyldiimidazole was added at room temperature, and the mixture was stirred at 50 °C for 20 hours. After the reaction was complete, the solvent was distilled off under reduced pressure. 5 ml of 1 mol / L hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate (5 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The solid was washed with 2 ml of diisopropyl ether to obtain 90 mg of the target compound as a white solid with a melting point of 197–199 °C.

[0403] Synthetic Example 6: Synthesis of 1-(tert-butyl)-N-(4-(5-methoxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-009) To a mixed solution of 100 mg 1-(tert-butyl)-N-(4-(5-hydroxy-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide, 40 mg potassium carbonate, and 2 ml acetonitrile, 33 mg iodomethane was added at room temperature, and the mixture was stirred at 50 °C for 14 hours. After stirring, 73 mg iodomethane was added to the reaction mixture at the same temperature, and the mixture was stirred at 60 °C for 1 hour. After the reaction was complete, the solvent was distilled off under reduced pressure. 3 ml of water was added to the residue, and the mixture was extracted with ethyl acetate (3 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 1:9) as the eluent to obtain 83 mg of the target analyte as an oil.

[0404] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.44-7.40(m,3H),7.39-7.30(m,3H),7.26-7.22(m,1H),7.16(s,1H),7.1 4-7.07(m,1H),6.60-6.50(m,1H),3.67(q,J=6.8Hz,2H),2.88(t,J=7.1Hz,2H),3.27(s,3H),1.72(s,9H).

[0405] Synthetic Example 7: Synthesis of N-(4-(5-amino-1,2,4-oxadiazol-3-yl)phenethyl)-1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide (Compound No. 1-145) Step 1: Synthesis of 1-(tert-butyl)-N-(4-(5-(methylsulfinyl)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.19 g of 1-(tert-butyl)-N-(4-(5-(methylthio)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide and 30 ml of dichloromethane, 1.00 g of m-chloroperbenzoic acid (containing 30% by mass water) was added under ice-cold conditions, and the mixture was stirred at room temperature for 5 hours. After the reaction was complete, 30 ml of saturated sodium bicarbonate aqueous solution and 30 ml of saturated sodium thiosulfate aqueous solution were added at room temperature, and the mixture was extracted with dichloromethane (50 ml × 3 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure to obtain 1.20 g of the target compound as a resinous substance.

[0406] Step 2: Synthesis of N-(4-(5-amino-1,2,4-oxadiazol-3-yl)phenethyl)-1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide A mixture of 520 mg of 1-(tert-butyl)-N-(4-(5-(methylsulfinyl)-1,2,4-oxadiazol-3-yl)phenethyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide, 8 ml of 30% ammonia, and 4 ml of tetrahydrofuran was stirred at room temperature for 5 hours. After the reaction was complete, 50 ml of water was added at room temperature, and the mixture was extracted with ethyl acetate (50 ml × 3 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 0:10) as the eluent to obtain 380 mg of the target substance as a white solid with a melting point of 174-176 °C.

[0407] Synthetic Example 8: Synthesis of 3-(4-(2-(1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxamide)ethyl)phenyl)-N-isopropyl-1,2,4-oxadiazole-5-carboxamide (Compound No. 1-147) To a mixed solution of 50 mg 1-(tert-butyl)-4-(3-methylphenoxy)-N-(4-(5-(trichloromethyl)-1,2,4-oxadiazol-3-yl)phenethyl)-1H-pyrazole-5-carboxamide and 1 ml tetrahydrofuran, 90 μl of isopropylamine was added at room temperature and the mixture was stirred for 16 hours at the same temperature. After the reaction was complete, 10 ml of water was added at room temperature, and the mixture was extracted with chloroform (15 ml × 3 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 1:9) as the eluent to obtain 35 mg of the target substance as an oil.

[0408] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.94-7.90(m,1H),7.42-7.40(m,1H),7.29-7.12(m,3H),7.10(s,1H),7.00-6.87(m,2H),6.76-6.72(m,3 H),4.37-4.27(m,1H),3.71-3.63(m,2H),2.91-2.84(m,2H),2.35-2.25(m,3H),1.76-1.66(m,9H),1.35-1.30(m,3H),1.28-1.19(m,3H).

[0409] Synthetic Example 9: Synthesis of 1-(tert-butyl)-N-(4-(2-methyl-2H-tetrazol-5-yl)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyridine (Compound No. 1-322) To a mixed solution of 38 mg 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 1 ml N,N-dimethylformamide, 44 mg 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxafluorophosphate, 40 mg diisopropylethylamine, and 25 mg 2-(4-(2-methyl-2H-tetrazol-5-yl)phenyl)ethane-1-amine hydrochloride were added at room temperature, and the mixture was stirred for 2 hours. After the reaction was complete, 2 ml of saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was extracted with a 1:1 mixture of n-hexane and ethyl acetate (2 ml × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (from a gradient of 9:1 to 1:9) as the eluent, yielding 28 mg of the target substance as an oil.

[0410] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.96-7.93(m,2H),7.39-7.03(m,8H),4.38(s,3H),3.70-3.63(m,2H),2.84(t,J=6.8Hz,2H),1.66(s,9H).

[0411] [Reference Example] Hereinafter, by way of reference, a method for manufacturing intermediates of the compounds of the present invention is shown.

[0412] Reference Example 1: Synthesis of 4-iodo-1-phenyl-1H-pyrazole-5-carboxylic acid To a mixed solution of 2.0 g of 1-phenyl-1H-pyrazole-5-carboxylic acid and 10 ml of acetic acid, 2.5 g of N-iodosuccinimide was added at room temperature, and the mixture was stirred at 80 °C for 30 minutes. After the reaction was complete, 50 ml of water was added at room temperature, and the precipitated solid was filtered off. The obtained solid was dried under reduced pressure to obtain 2.69 g of the target compound, which was a pink solid with a melting point of 191-193 °C.

[0413] Reference Example 2: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one A mixed solution of 4.7 g of 1-(3-(trifluoromethyl)phenoxy)propane-2-one and 2.9 g of N,N-dimethylformamide dimethyl acetal was stirred at 80 °C for 16 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as the eluent. 10 ml of diisopropyl ether and 10 ml of n-hexane were added to the resulting oil, and the precipitated solid was filtered off. The solid was dried under reduced pressure to give 2.36 g of the target substance as a light brown solid with a melting point of 112-114 °C.

[0414] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.4 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one, 1.64 g of tert-butylhydrazine hydrochloride, and 25 ml of 1,4-dioxane was stirred at 100 °C for 3 hours. After the reaction was complete, the solvent was distilled off under reduced pressure. 20 ml of water was added to the residue, and the mixture was extracted with n-hexane (20 ml × 2 times). The resulting organic layer was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (5:1) as the eluent to obtain 2.51 g of the target compound as a pale yellow oil.

[0415] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.42-7.32(m,1H),7.28(s,1H),7.28-7.22(m,1H),7.21-7.14(m,1H),7.12-7.04(m,1H),2.29(s,3H),1.66(s,9H).

[0416] Step 3: Synthesis of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid To a mixed solution of 930 mg 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole, 8.5 ml tert-butanol, and 4.3 ml water, 1.48 g of potassium permanganate was added at room temperature, and the mixture was stirred at 100 °C for 2 hours. After stirring, 1.48 g of potassium permanganate was added to the reaction mixture at the same temperature, and the mixture was stirred for another 2 hours. After the reaction was complete, the reaction mixture was filtered through diatomaceous earth, and the diatomaceous earth was washed with 20 ml of water. The aqueous layer of the resulting filtrate was washed with chloroform (20 ml × 2 times), and then 1 mol / L hydrochloric acid was added until the pH reached 1, followed by extraction with chloroform (20 ml × 2 times). The resulting organic layer was washed with water, then dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 ml of n-hexane and then dried under reduced pressure to obtain 209 mg of the target substance as a white solid. Its melting point is 120-124℃.

[0417] Reference Example 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)propenal To 15 ml of N,N-dimethylformamide, 5.6 ml of phosphorus oxychloride was added under ice-cold conditions, and the mixture was stirred at this temperature for 15 minutes. After stirring, to the reaction mixture, 5 ml of a solution of 1-(2,2-dimethoxyethoxy)-3-(trifluoromethyl)benzene (5.0 g) in N,N-dimethylformamide was added under ice-cold conditions, and the mixture was stirred at 70°C for 30 minutes. After the reaction was complete, the reaction mixture was added to a mixed solution of 28 g of potassium carbonate, 50 ml of water, and 5 ml of ethanol, and stirred at room temperature for 1 hour. After stirring, the reaction mixture was extracted with toluene (40 ml × 2 times). The resulting organic layer was washed with water, then dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 4.40 g of the target substance as a brown oil.

[0418] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ8.82 (s, 1H), 7.52-7.03 (m, 3H), 7.03-6.95 (m, 1H), 6.62 (s, 1H), 3.12 (br, 6H).

[0419] Step 2: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 2.0 g of 3-(dimethylamino)-2-(3-(trifluoromethyl)phenoxy)propenal, 2.4 g of benzylhydrazine hydrochloride, 2.1 ml of triethylamine, and 25 ml of 1,4-dioxane was stirred at 100 °C for 3 hours. After the reaction was complete, 20 ml of 1 mol / L hydrochloric acid was added to the reaction mixture at room temperature, and the mixture was extracted with chloroform (30 ml × 2 times). The resulting organic layer was washed with water, then dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 1:9) as the eluent to obtain 400 mg of the target substance as a red oil.

[0420] 1 H-NMR (CDCl3, Me4Si, 400MHz): δ7.46-7.20(m,7H),7.20-7.14(m,2H),7.10-7.06(m,1H),7.03-6.96(m,1H),5.29(s,2H) Step 3: Synthesis of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid Under a nitrogen atmosphere, 0.85 ml of a 1.6 mol / L n-butyllithium n-hexane solution was added dropwise to a 10 ml tetrahydrofuran solution containing 360 mg of 1-benzyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole at -78 °C, and the mixture was stirred for 10 minutes at this temperature. After stirring, 1.0 g of dry ice was added to the reaction mixture at -78 °C, and the mixture was stirred for 5 minutes at this temperature. After the reaction was complete, 10 ml of 1 mol / L hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 2 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate:acetic acid (in a gradient from 74:25:1 to 39:60:1) as the eluent to obtain 45 mg of the target substance as a colorless solid with a melting point of 124-126 °C.

[0421] Reference Example 4: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (compound No. i-036) Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate (compound No. ii-004) To a mixed solution of 1.00 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid and 10 ml of acetone, 0.49 g of potassium carbonate and dimethyl sulfate were added sequentially at room temperature, and the mixture was stirred for 3 hours at the same temperature. After the reaction was complete, the solvent was distilled off under reduced pressure. 20 ml of water was added to the residue, and the mixture was extracted with ethyl acetate (20 ml × 2 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target compound as a yellow solid with a melting point of 69-71 °C.

[0422] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (compound No. ii-005) Under a nitrogen atmosphere, 0.10 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium (2-valent) dichloride was added to a mixed solution of 0.50 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylborooxane, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane at room temperature, and the mixture was stirred at 100 °C for 16 hours. After the reaction was complete, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 3 times). The mixture was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 10:0 to 9:1) as the eluent to obtain 0.30 g of the target substance as a yellow oil.

[0423] 1 H-NMR (CDCl3, Me4Si, 400MHz) δ7.24(s,1H),7.20-7.13(m,1H),6.90-6.85(m,1H),6.84-6.76(m,2H),3.77(s,3H),2.33(s,3H),1.72(s,3H).

[0424] Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid (compound No. i-036) A mixture of 39.0 g of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol was added to a mixture of 27.1 g of sodium hydroxide and 100 ml of water at room temperature, and the mixture was stirred at 45 °C for 16 hours. After the reaction was complete, the solvent was distilled off under reduced pressure. 50 ml of water was added to the residue, followed by the addition of 35% hydrochloric acid until the pH reached 2. The precipitated solid was then filtered off. The solid was dried under reduced pressure and washed with 100 ml of n-hexane to obtain 37.0 g of the target compound as a white solid with a melting point of 116-118 °C.

[0425] Reference Example 5: Synthesis of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoic acid Step 1: Synthesis of methyl 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoate To a mixed solution of 3.25 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 20 ml of dichloromethane, 7 mg of N,N-dimethylformamide and 1.3 ml of oxaloyl chloride were added sequentially at room temperature, and the mixture was stirred for 1 hour at this temperature. After the reaction was complete, the solvent was distilled off under reduced pressure, and then 25 ml of dichloromethane was added to the residue. This reaction mixture was then added to a mixed solution of 2.35 g of methyl 4-(2-aminoethyl)benzoate hydrochloride, 4.1 ml of triethylamine, and 20 ml of dichloromethane under ice-cold conditions, and stirred for 1 hour at room temperature. After the reaction was complete, 30 ml of water was added to the reaction mixture, and the mixture was extracted with chloroform (10 ml × 1 time). The resulting organic layer was washed with 1 mol / L hydrochloric acid, dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 9:1 to 8:2) as the eluent. The resulting solid was washed with 10 ml of n-hexane to give 3.19 g of the target substance as a white solid.

[0426] 1 H-NMR (CDCl3, Me4Si, 300MHz): δ7.88-7.81(m,2H),7.45-7.30(m,2H),7.23-7.16(m,3H),7.13(s,1H),7 .10-7.00(m,1H),6.52-6.39(m,1H),3.89(s,3H),3.73-3.61(m,2H),2.86(t,J=6.8Hz,2H),1.72(s,9H).

[0427] Step 2: Synthesis of 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoic acid To a mixed solution of 1.20 g of methyl 4-(2-(1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide)ethyl)benzoate and 8 mL of ethanol, 8 mL of 1 mol / L sodium hydroxide aqueous solution was added at room temperature, and the mixture was stirred for 1 hour at this temperature. After the reaction was complete, the solvent was distilled off under reduced pressure. 10 mL of 1 mol / L hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate (20 mL × 1 time). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 mL of diisopropyl ether to obtain 0.84 g of the target compound as a white solid.

[0428] Reference Example 6: Synthesis of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamoylimino)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide Step 1: Synthesis of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.63 g of 1-(tert-butyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxylic acid and 10 mL of dichloromethane, 0.95 g of oxaloyl chloride and 4 mg of N,N-dimethylformamide were added sequentially at room temperature, and the mixture was stirred for 1 hour at this temperature. After the reaction was complete, the solvent was distilled off under reduced pressure, and 10 mL of ethyl acetate was added to the residue. This reaction mixture was then added under ice-cold conditions to a mixed solution of 1.00 g of 4-(2-aminoethyl)benzonitrile hydrochloride, 1.71 g of potassium carbonate, and 10 mL of water, and stirred at room temperature for 15 hours. After the reaction was complete, the organic layer of the reaction mixture was washed with 1 mol / L hydrochloric acid, dehydrated with anhydrous sodium sulfate, dried, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as the eluent to obtain 2.26 g of the target substance as an orange solid. Melting point: 124-125℃.

[0429] Step 2: Synthesis of 1-(tert-butyl)-N-(4-(N'-hydroxycarbamoylimino)phenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 1.26 g of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 10 ml of ethanol, 0.23 g of hydroxylamine hydrochloride and 0.46 g of potassium carbonate were added sequentially at room temperature, followed by stirring at 80 °C for 1 hour. After stirring, 0.36 g of a 50% (w / w) aqueous solution of hydroxylamine was added at the same temperature, and the mixture was stirred for another 3 hours. After the reaction was complete, 30 ml of water was added to the reaction mixture, and the precipitated solid was filtered off. The obtained solid was dried under reduced pressure and washed with 20 ml of diisopropyl ether to obtain 1.00 g of the target compound, a pale pink solid with a melting point of 126-128 °C.

[0430] Reference Example 7: Synthesis of 1-(tert-butyl)-N-(4-aminothioformylphenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide To a mixed solution of 0.50 g of 1-(tert-butyl)-N-(4-cyanophenethyl)-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole-5-carboxamide and 5 ml of N,N-dimethylformamide, 0.11 g of magnesium chloride and 176 mg of sodium hydrosulfide hydrate (purity: 70% by mass) were added sequentially at room temperature, and the mixture was stirred for 3 hours at this temperature. After the reaction was complete, the solvent was distilled off under reduced pressure, and 10 ml of ethyl acetate was added to the residue. This reaction mixture was then added under ice-cold conditions to a mixed solution of 1.00 g of 4-(2-aminoethyl)benzonitrile hydrochloride, 1.71 g of potassium carbonate, and 10 ml of water, and stirred for 15 hours at room temperature. After the reaction was complete, 10 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (10 ml × 1 time). The resulting organic layer was washed with water, then dehydrated and dried with anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain 530 mg of the target substance as a pale yellow solid. Its melting point was 164-166 °C.

[0431] Reference Example 8: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole Step 1: Synthesis of 3-oxo-2-(3-(trifluoromethyl)phenoxy)butyraldehyde To a mixed solution of 3.00 g of 4-(dimethylamino)-3-(3-(trifluoromethyl)phenoxy)but-3-en-2-one and 30 mL of toluene, 1 mol / L hydrochloric acid was added at room temperature, and the mixture was stirred at 50 °C for 7 hours. After the reaction was complete, the reaction mixture was extracted with toluene (30 mL × 1 time). The resulting organic layer was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 10 mL of diisopropyl ether to obtain 2.34 g of the target compound as a light brown solid. Melting point: 115-117 °C.

[0432] Step 2: Synthesis of 1-(tert-butyl)-5-methyl-4-(3-(trifluoromethyl)phenoxy)-1H-pyrazole A mixed solution of 830 mg of 3-oxo-2-(3-(trifluoromethyl)phenoxy)butanal, 500 mg of tert-butylhydrazine hydrochloride, and 8 ml of toluene was stirred at 50 °C for 4 hours. After the reaction was completed, the reaction mixture was washed successively with 10 ml of water and 10 ml of 1 mol / L sodium hydroxide aqueous solution. The resulting organic layer was dehydrated with anhydrous sodium sulfate, dried, and then the solvent was removed by distillation under reduced pressure to obtain 970 mg of the target compound as a pale yellow oil.

[0433] 1H-NMR (CDCl3, Me4Si, 300MHz): δ7.42-7.32(m,1H),7.28(s,1H),7.28-7.22(m,1H),7.21-7.14(m,1H),7.12-7.04(m,1H),2.29(s,3H),1.66(s,9H).

[0434] Reference Example 9: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid Step 1: Synthesis of methyl 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate To a mixed solution of 1.00 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylic acid and 10 ml of acetone, 0.49 g of potassium carbonate and 0.67 g of dimethyl sulfate were added sequentially at room temperature, and the mixture was stirred for 3 hours at the same temperature. After the reaction was complete, the solvent was distilled off under reduced pressure. 20 ml of water was added to the residue, and the mixture was extracted with ethyl acetate (20 ml × 2 times). The resulting organic layer was dehydrated and dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.90 g of the target compound as a yellow solid. The melting point was 69-71 °C.

[0435] Step 2: Synthesis of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate (compound No. ii-005) Under a nitrogen atmosphere, 0.10 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium (2-valent) dichloride was added to a mixed solution of 0.50 g of 4-(3-bromophenoxy)-1-(tert-butyl)-1H-pyrazole-5-carboxylate, 0.89 g of trimethylborooxane, 0.92 g of cesium carbonate, and 10 ml of 1,4-dioxane at room temperature, and the mixture was stirred at 100 °C for 16 hours. After the reaction was complete, 20 ml of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (20 ml × 3 times). The mixture was then dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (in a gradient from 10:0 to 9:1) as the eluent to obtain 0.30 g of the target compound as a yellow oil.

[0436] 1H-NMR(CDCl3,Me4Si,400MHz)δ7.24(s,1H),7.20-7.13(m,1H),6.90-6.85(m,1H),6.84-6.76(m,2H),3.77(s,3H),2.33(s,3H),1.72(s,3H) Step 3: Synthesis of 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylic acid A mixture of 39.0 g of methyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate and 100 ml of methanol was added at room temperature, followed by stirring at 45 °C for 16 hours. After the reaction was complete, the solvent was distilled off under reduced pressure. 50 ml of water was added to the residue, followed by the addition of 35% hydrochloric acid until the pH reached 2. The precipitated solid was then filtered off. The solid was dried under reduced pressure and washed with 100 ml of n-hexane to obtain 37.0 g of the target compound as a white solid with a melting point of 116-118 °C.

[0437] Reference Example 10: Synthesis of ethyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate Step 1: Synthesis of 2-(3-methylphenoxy)acetaldehyde 20 g of 1-(2,2-dimethoxyethoxy)-3-methylbenzene was added dropwise to a mixture of 102 ml of 20% hydrochloric acid and 60 ml of acetone at room temperature over a period of 2.5 hours, and the mixture was stirred at the same temperature for 1 hour. After stirring, 34 ml of 20% hydrochloric acid was added at room temperature, and the mixture was stirred at the same temperature for 30 minutes. After the reaction was complete, 6.6 ml of toluene and 13.4 ml of heptane were added to the reaction mixture, and the aqueous layer was separated by liquid-liquid extraction. 40 ml of water was added to the resulting organic layer, and the aqueous layer was extracted. The aqueous layers were combined, 12 g of sodium chloride was added, and the mixture was extracted with chloroform (120 ml × 3 times). The resulting organic layer was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and then approximately 200 ml of solvent was distilled off under reduced pressure. Then, 200 ml of toluene was added, and the solvent was distilled off again under reduced pressure, yielding 45 g of a toluene solution containing 14.5 g of the target compound.

[0438] 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 9.88-9.86 (m, 1H), 7.20-7.14 (m, 1H), 6.87-6.67 (m, 3H), 4.56 (s, 2H), 2.33 (s, 3H).

[0439] Step 2: Synthesis of ethyl 4-morpholino-2-oxo-3-(3-methylphenoxy)but-3-enoate To a mixed solution of 12.7 g morpholine and 300 ml toluene, 42 g of a toluene solution containing 13.8 g of 2-(3-methylphenyl)acetaldehyde, obtained in step 1, was added dropwise over 2 hours at reflux at 20 kPa and 58 °C. During the addition, the toluene-water mixture was distilled off. After the addition was complete, the mixture was stirred for 1 hour under the same conditions. After stirring, a total of 92 g of the toluene-water mixture, including the initial distillate, was distilled off. The mixture was cooled to 10 °C under reduced pressure and then the pressure was released. To this reaction mixture, 19.6 g of triethylamine and 26.4 g of ethyl chloroglyoxylate were added dropwise sequentially under ice-cold conditions, and the mixture was stirred at this temperature for 1 hour. After stirring, the mixture was stirred overnight at room temperature. After the reaction was complete, 60 ml of water was added to the reaction mixture, and the organic layer was extracted by separation. The obtained organic layer was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradients from 1:1 to 1:4) as the eluent, yielding 19 g of the target substance as an oil.

[0440] 1 H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.53-7.51(m,1H), 7.17-7.11(m,1H), 6.83-6.70(m,3H), 4.38-4.25(m,2H), 3.75-3.40(m,8H), 1.42-1.22(m,6H).

[0441] Step 3: Synthesis of ethyl 1-(tert-butyl)-4-(3-methylphenoxy)-1H-pyrazole-5-carboxylate 1 ml of acetic acid was added to a mixed solution of 5.1 g of ethyl 4-morpholino-2-oxo-3-(3-methylphenoxy)but-3-enoate, 2.2 g of tert-butylhydrazine hydrochloride, and 30 ml of toluene, and the mixture was stirred at 80 °C for 3 hours. After stirring, 30 ml of ethanol was added to the reaction mixture, followed by dropwise addition of 36 g of 10% sodium hydroxide aqueous solution under ice-cold conditions. After the addition was complete, the mixture was stirred at 40 °C for 3 hours. After the reaction was complete, 20 ml of toluene was added to the reaction mixture, and the organic layer was extracted by separation. The obtained organic layer was dehydrated and dried successively with saturated brine and anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure to obtain 1.1 g of the target compound as an oil.

[0442] 1H-NMR (CDCl3, Me4Si, 300MHz) δ: 7.20-7.09 (m, 2H), 6.87-6.61 (m, 3H), 4.24-4.16 (m, 2H), 2.31 (s, 3H), 1.71 (s, 9H), 1.15-1.10 (m, 3H).

[0443] The compounds of the present invention can be synthesized with reference to the above-described synthesis examples and reference examples. Examples of the compounds of the present invention obtained according to synthesis examples 1 to 9 are shown in Tables 1 to 2. In addition, examples of preparation intermediates obtained according to reference examples 1 to 10 are shown in Tables 3 to 5, but the compounds and preparation intermediates of the present invention are not limited to these examples.

[0444] In the table, the substituent "Me" indicates "methyl". Similarly, "Et" indicates "ethyl", "nPr" indicates "n-propyl", "tBu" indicates "tert-butyl", "iPr" indicates "isopropyl", "cPr" indicates "cyclopropyl", "cHex" indicates "cyclohexyl", "nBu" indicates "n-butyl", "iBu" indicates "isobutyl", "Ac" indicates "acetyl", "Ph" indicates "phenyl", and "Bn" indicates "benzyl". Additionally, the symbol "*" indicates that the compound is an oily or resinous compound without a melting point, and "mp" indicates the melting point (in °C).

[0445] Additionally, in the table, for example, "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.

[0446] [Chemical Formula 44]

[0447] Additionally, the substituents designated as D-1a, D-2a, D-3a, E-2a, E-3a, E-4a, E-5a, E-6a, E-7a, E-8a, E-9a, E-10a, E-11a, E-12a, E-13a, E-16a, E-17a, E-18a, E-19a, E-20a, E-21a, E-24a, E-25a, E-26a, E-27a, E-29a, E-30a, F-2a, F-3a, F-4a, L-1, L-2, L-3, L-4, L-5, L-6, L-7, L-8, and L-9 represent the following structures, respectively.

[0448] [Chemical Formula 45]

[0449] [Chemical Formula 46]

[0450] [Chemical Formula 47]

[0451] [Chemical Formula 48]

[0452] It should be noted that the numbers marked in the above structural formulas indicate the substitution positions. For example, "4-Me-(E-2a)" in the table represents the following structure. If no substituent is listed in the table, it means that there is no substitution.

[0453] [Chemical Formula 49]

[0454] [Table 1] [Chemical Formula 50]

[0455] ―――――――――――――――――――――――――――――――

[0456] ――――――――――――――――――――――――――――――

[0457] ―――――――――――――――――――――――――――――― [Table 2] [Chemical Formula 51]

[0458] ――――――――――――――――――――――――――――――

[0459] ――――――――――――――――――――――――――――――

[0460] ――――――――――――――――――――――――――――― [Table 3] [Chemical Formula 52]

[0461] ―――――――――――――――――――――――――――――

[0462] ―――――――――――――――――――――――――――――

[0463] ――――――――――――――――――――――――――――― [Table 4] [Chemical Formula 53]

[0464] ―――――――――――――――――――――――――――――

[0465] ―――――――――――――――――――――――――――――

[0466] ――――――――――――――――――――――――――――― [Table 5] [Chemical Formula 54]

[0467] ――――――――――――――――――――――――――――――

[0468] ――――――――――――――――――――――――――――――

[0469] ――――――――――――――――――――――――――――― Table 6 shows the compounds of the present invention whose melting points were not indicated in Tables 1 and 2. 1 H-NMR data. Here, the data below are measured in deuterated chloroform. The notation "#1" indicates that it was measured at 300 MHz (model JNM-ECX300 or JNM-ECP300; manufactured by JEOL). Similarly, the notation "#2" indicates that it was measured at 400 MHz (model JNM-ECZ400S; manufactured by JEOL).

[0470] [Table 6] ――――――――――――――――――――――――――――――

[0471] ―――――――――――――――――――――――――――――― 1-009(#1):δ7.44-7.40 (m, 3H), 7.39-7.30 (m, 3H), 7.26-7.22 (m, 1H), 7.16 (s, 1H), 7.14-7.07 (m, 1H), 6.60-6.50 (m, 1H), 3.67 (q, J = 6.8 Hz, 2H), 2.88 (t, J = 7.1 Hz, 2H), 3.27 (s, 3H), 1.72 (s, 9H).

[0472] 1-010(#1):δ7.48-7.30 (m, 6H), 7.26-7.23 (m, 1H), 7.16 (s, 1H), 7.13-7.07 (m, 1H), 6.55-6.45 (m, 1H), 3.74-3.62 (m, 4H), 2.88 (t, J = 7.1 Hz, 2H), 1.72 (s, 9H), 1.24 (t, J = 7.2 Hz, 3H).

[0473] 1-011(#1):δ7.76 (d, J = 8.1 Hz, 2H), 7.40-7.27 (m, 2H), 7.25-7.13 (m,4H), 7.08-7.01 (m, 1H), 6.85 (s, 1H), 6.50-6.40 (m, 1H), 3.66 (q, J = 6.7 Hz,2H), 2.83 (t, J = 6.9 Hz, 2H), 2.98 (s, 3H), 1.72 (s, 9H)。

[0474] 1-012(#1):δ7.73 (d, J = 8.7 Hz, 2H), 7.40-7.28 (m, 2H), 7.24-7.20 (m,1H), 7.19-7.12 (m, 3H), 7.07-7.01 (m, 1H), 6.80 (s, 1H), 6.48-6.38 (m, 1H),3.65 (q, J = 6.5 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 2.14-1.95 (m, 1H), 1.72(s, 9H), 0.99-0.93 (m, 4H)。

[0475] 1-018(#1):δ7.89 (d, J = 8.4 Hz, 2H), 7.24 (d, J = 8.1 Hz, 2H), 7.19-7.10 (m, 2H), 6.92-6.85 (m, 1H), 6.77-6.68 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H),2.86 (t, J = 7.1 Hz, 2H), 2.64 (s, 3H), 2.29 (s, 3H), 1.72 (s, 9H)。

[0476] 1-019(#1):δ7.90 (d, J = 8.4 Hz, 2H), 7.28 (d, J = 8.1 Hz, 2H), 7.19-7.11 (m, 1H), 7.09 (s, 1H), 6.90-6.84 (m, 1H), 6.78-6.68 (m, 3H), 3.69 (q, J= 6.5 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。

[0477] 1-020(#1):δ7.91 (d, J = 8.1 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 7.19-7.09 (m, 2H), 6.90-6.84 (m, 1H), 6.86 (t, J = 52.5 Hz, 1H), 6.78-6.68 (m,3H), 3.68 (q, J = 6.6 Hz, 2H), 2.88 (t, J = 6.9 Hz, 2H), 2.28 (s, 3H), 1.73(s, 9H)。

[0478] 1-021(#2):δ7.91 (d, J = 6.0 Hz, 2H), 7.24 (d, J = 6.3 Hz, 2H), 7.19-7.15 (m, 1H), 7.12 (s, 1H), 6.91-6.86 (m, 1H), 6.78-6.69 (m, 3H), 3.67 (q, J= 4.9 Hz, 2H), 2.98 (q, J = 6.0 Hz, 2H), 2.86 (t, J = 5.3 Hz, 2H), 2.29 (s,3H), 1.72 (s, 9H), 1.46 (t, J = 5.6 Hz, 3H)。

[0479] 1-022(#1):δ7.90 (d, J = 8.1 Hz, 2H), 7.23 (d, J = 8.1 Hz, 2H), 7.20-7.09 (m, 2H), 6.91-6.84 (m, 1H), 6.78-6.68 (m, 3H), 3.66 (q, J = 6.3 Hz, 2H),2.96-2.82 (m, 4H), 2.29 (s, 3H), 2.00-1.84 (m, 2H), 1.73 (s, 9H), 1.07 (t, J= 7.5 Hz, 3H)。

[0480] 1-023(#1):δ7.90 (d, J = 8.4 Hz, 2H), 7.23 (d, J = 8.7 Hz, 2H), 7.19-7.09 (m, 2H), 6.91-6.85 (m, 1H), 6.78-6.67 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H),3.28 (sep, J = 7.1 Hz, 1H), 2.86 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.73 (s,9H), 1.46 (d, J = 7.2 Hz, 6H)。

[0481] 1-024(#1):δ7.86 (d, J = 8.1 Hz, 2H), 7.22 (d, J = 8.1 Hz, 2H), 7.19-7.09 (m, 2H), 6.92-6.85 (m, 1H), 6.80-6.66 (m, 3H), 3.66 (q, J = 6.5 Hz, 2H),2.85 (t, J = 6.9 Hz, 2H), 2.30-2.20 (m, 4H), 1.72 (s, 9H), 1.35-1.20 (m, 4H)。

[0482] 1-025(#1):δ7.93 (d, J = 7.8 Hz, 2H), 7.26 (d, J = 8.1 Hz, 2H), 7.19-7.09 (m, 2H), 6.91-6.85 (m, 1H), 6.78-6.68 (m, 3H), 4.74 (s, 2H), 3.67 (q, J= 6.6 Hz, 2H), 3.56 (s, 3H), 2.86 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.73 (s,9H)。

[0483] 1-033(#1):δ7.93-7.87 (m, 2H), 7.82-7.18 (m, 4H), 7.12 (s, 1H), 7.09-7.03 (m, 1H), 6.95-6.87 (m, 2H), 6.88-6.56 (m, 1H), 3.70-3.62 (m, 2H), 3.34-3.21 (m, 1H), 2.84 (t, J = 7.0 Hz, 2H), 1.73 (s, 9H), 1.47 (d, J = 6.8 Hz,6H)。

[0484] 1-074(#1):δ8.47 (s, 1H), 8.00-7.94 (m, 2H), 7.43-7.36 (m, 1H), 7.35-7.28 (m, 3H), 7.19 (s, 1H), 7.14 (s, 1H), 7.10-7.05 (m, 1H), 6.56-6.48 (m,1H), 3.753.64 (m, 2H), 2.94-2.86 (m, 2H), 1.72 (s, 9H)。

[0485] 1-076(#2):δ7.93 (d, J = 8.4 Hz, 2H), 7.25 (d, J = 8.1 Hz, 2H), 7.16(t, J = 7.9 Hz, 1H), 7.12 (s, 1H), 6.89 (d, J = 7.7 Hz, 1H), 6.75-6.71 (m,3H), 4.79 (s, 2H), 3.72-3.67 (m, 4H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H),1.74 (d, J = 11.7 Hz, 9H), 1.31 (t, J = 7.0 Hz, 3H)。

[0486] 1-077(#1):δ7.96-7.86 (m, 2H), 7.32-7.21 (m, 2H), 7.19-7.07 (m, 2H),6.91-6.66 (m, 4H), 3.76-3.62 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.77 (t, J =7.5 Hz, 2H), 2.28 (s, 3H), 1.93-1.79 (m, 2H), 1.73 (s, 9H), 1.04 (t, J = 7.3Hz, 3H)。

[0487] 1-078(#1):δ7.94-7.78 (m, 2H), 7.32-7.19 (m, 2H), 7.19-7.05 (m, 2H),6.94-6.82 (m, 1H), 6.81-6.61 (m, 3H), 3.76-3.59 (m, 2H), 2.88 (t, J = 6.8 Hz,2H), 2.28 (s, 3H), 2.22-2.08 (m, 1H), 1.73 (s, 9H), 1.18-1.02 (m, 4H)。

[0488] 1-079(#1):δ7.73-7.68 (m, 2H), 7.23-7.11 (m, 5H), 6.91-6.86 (m, 1H),6.78-6.64 (m, 3H), 3.69-3.60 (m, 2H), 2.86-2.79 (m, 2H), 2.77 (s, 3H), 2.27(s, 3H), 1.73 (s, 9H)。

[0489] 1-082(#1):δ8.68 (s, 1H), 8.61 (s, 1H), 7.41-7.35 (m, 2H), 7.23-7.07(m, 4H), 6.93-6.86 (m, 1H), 6.77-6.68 (m, 3H), 3.71-3.61 (m, 2H), 2.90-2.77(m, 2H), 2.27 (s, 3H), 1.72 (s, 9H)。

[0490] 1-083(#1):δ8.34 (s, 1H), 7.19-7.07 (m, 6H), 6.96-6.89 (m, 1H), 6.81-6.67 (m, 3H), 3.70-3.57 (m, 2H), 2.88-2.78 (m, 2H), 2.38 (s, 3H), 2.28 (s,3H), 1.75 (s, 9H)。

[0491] 1-085(#1):δ8.74 (s, 1H), 8.00 (s, 1H), 7.40-7.35 (m, 2H), 7.21-7.09(m, 4H), 6.93-6.88 (m, 1H), 6.78-6.68 (m, 3H), 3.70-3.62 (m, 2H), 2.87-2.80(m, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。

[0492] 1-087(#1):δ 7.25-7.07 (m, 6H), 6.94-6.89 (m, 1H), 6.82-6.70 (m, 3H),3.70-3.62 (m, 2H), 2.87-2.80 (m, 2H), 2.37 (s, 3H), 2.30 (s, 3H), 2.23 (s,3H), 1.74 (s, 9H)。

[0493] 1-088(#1):δ8.47-8.44 (m, 1H), 7.43-7.37 (m, 2H), 7.34-7.31 (m, 1H),7.23-7.09 (m, 4H), 6.93-6.88 (m, 1H), 6.78-6.69 (m, 3H), 3.71-3.62 (m, 2H),2.89-2.81 (m, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。

[0494] 1-090(#1):δ7.74-7.68 (m, 2H), 7.30-7.24 (m, 2H), 7.19-7.07 (m, 2H),6.92-6.87 (m, 1H), 6.78-6.69 (m, 3H), 3.73-3.64 (m, 2H), 2.93-2.86 (m, 2H),2.29 (s, 3H), 1.73 (s, 9H)。

[0495] 1-091(#1):δ7.96 (s, 1H), 7.45-7.40 (m, 2H), 7.32-7.27 (m, 2H), 7.23-7.11 (m, 2H), 6.95-6.88 (m, 1H), 6.82-6.68 (m, 3H), 4.70-4.60 (m, 1H), 3.71-3.62 (m, 2H), 2.91-2.83 (m, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.51 (d, J = 6.5Hz, 6H)。

[0496] 1-092(#1):δ7.39-7.34 (m, 2H), 7.19-7.05 (m, 5H), 6.92-6.87 (m, 1H),6.75-6.67 (m, 3H), 3.69-3.61 (m, 2H), 2.86-2.78 (m, 2H), 2.28 (s, 3H), 2.17-2.06 (m, 1H), 1.73 (s, 9H), 1.18-1.02 (m, 4H)。

[0497] 1-093(#1):δ7.22-7.15 (m, 5H), 7.12 (s, 1H), 6.94-6.89 (m, 2H), 6.81-6.69 (m, 3H), 3.70-3.62 (m, 2H), 3.47 (s, 3H), 2.87-2.80 (m, 2H), 2.44 (s, 3H), 2.30 (s, 3H), 1.73 (s, 9H).

[0498] 1-094(#1):δ7.78-7.66 (m, 2H), 7.44-7.00 (m, 8H), 6.51-6.35 (m, 1H),3.72-3.60 (m, 2H), 2.82 (t, J = 7.0 Hz, 2H), 2.77 (s, 3H), 1.72 (s, 9H)。

[0499] 1-095(#1):δ7.98-7.92 (m, 2H), 7.28-7.21 (m, 2H), 7.19-7.10 (m, 2H), 6.90-6.84 (m, 1H), 6.76-6.68 (m, 3H), 4.20-4.15 (m, 3H), 3.74-3.60 (m, 2H), 2.92-2.81 (m, 2H), 2.39 (s, 3H), 2.30 (s, 3H), 1.73 (s, 9H).

[0500] 1-096(#1): δ7.99-7.90 (m, 2H), 7.44-7.29 (m, 2H), 7.28-7.17 (m, 3H), 7.16-7.00 (m, 2H), 6.52-6.43 (m, 1H), 4.17 (s, 3H), 3.74-3.61 (m, 2H), 2.91-2.80 (m, 2H), 2.38 (s, 3H), 1.72 (s, 9H).

[0501] 1-098(#1):δ7.97-7.89 (m, 2H), 7.44-7.16 (m, 5H), 7.16-7.03 (m, 2H),6.58-6.44 (m, 1H), 4.77-4.64 (m, 1H), 3.71-3.61 (m, 2H), 3.47 (s, 3H), 2.91-2.79 (m, 2H), 1.72 (s, 9H), 1.69-1.62 (m, 3H)。

[0502] 1-099(#1):δ7.79-7.65 (m, 2H), 7.48-6.94 (m, 8H), 6.54-6.33 (m, 1H),3.72-3.57 (m, 2H), 3.09 (q, J = 7.6 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 1.72(s, 9H), 1.44 (t, J = 7.6 Hz, 3H)。

[0503] 1-100(#1):δ7.79-7.67 (m, 2H), 7.53-6.94 (m, 8H), 6.53-6.33 (m, 1H),3.74-3.56 (m, 2H), 3.44-3.31 (m, 1H), 2.88-2.69 (m, 2H), 1.72 (s, 9H), 1.45(d, J = 6.8 Hz, 6H)。

[0504] 1-101(#1):δ7.77-7.65 (m, 2H), 7.51-6.94 (m, 8H), 6.52-6.35 (m, 1H),3.72-3.55 (m, 2H), 2.90-2.71 (m, 2H), 2.45-2.29 (m, 1H), 1.72 (s, 9H), 1.22-1.05 (m, 4H)。

[0505] 1-102(#1):δ7.77-7.65 (m, 2H), 7.47-6.99 (m, 8H), 6.55-6.36 (m, 1H),4.79 (s, 2H), 4.27 (s, 3H), 3.74-3.60 (m, 2H), 2.82 (t, J = 6.8 Hz, 2H), 1.72(s, 9H)。

[0506] 1-103(#1):δ7.80-7.63 (m, 2H), 7.33-7.02 (m, 5H), 6.95-6.56 (m, 4H),3.70-3.58 (m, 2H), 3.09 (q, J = 7.7 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H), 2.27(s, 3H), 1.73 (s, 9H), 1.44 (t, J = 7.7 Hz, 3H)。

[0507] 1-104(#1):δ7.78-7.66 (m, 2H), 7.33-7.05 (m, 5H), 6.94-6.58 (m, 4H),3.70-3.59 (m, 2H), 3.44-3.31 (m, 1H), 2.82 (t, J = 6.8 Hz, 2H), 2.26 (s, 3H),1.73 (s, 9H), 1.45 (d, J = 6.8 Hz, 6H)。

[0508] 1-105(#1):δ7.75-7.64 (m, 2H), 7.22-7.06 (m, 5H), 6.92-6.83 (m, 1H),6.80-6.55 (m, 3H), 3.70-3.57 (m, 2H), 2.81 (t, J = 6.8 Hz, 2H), 2.42-2.30 (m,1H), 2.27 (s, 3H), 1.73 (s, 9H), 1.21-1.05 (m, 4H)。

[0509] 1-106(#1):δ7.77-7.65 (m, 2H), 7.38 (s, 1H), 7.24-7.05 (m, 4H), 6.93-6.83 (m, 1H), 6.80-6.62 (m, 3H), 4.79 (s, 2H), 3.72-3.59 (m, 2H), 3.53 (s,3H), 2.82 (t, J = 7.0 Hz, 2H), 2.27 (s, 3H), 1.73 (s, 9H)。

[0510] 1-108(#1):δ8.72-8.69 (m, 1H), 7.83-7.78 (m, 2H), 7.57-7.53 (m, 1H),7.25-7.20 (m, 2H), 7.17-7.10 (m, 2H), 6.90-6.85 (m, 1H), 6.78-6.68 (m, 3H),3.70-3.64 (m, 2H), 2.89-2.82 (m, 2H), 2.26 (s, 3H), 1.73 (s, 9H)。

[0511] 1-109(#1):δ7.69-7.60 (m, 2H), 7.25-7.08 (m, 4H), 6.95-6.60 (m, 5H),6.49-6.43 (m, 1H), 4.21 (q, J = 7.3 Hz, 2H), 3.73-3.58 (m, 2H), 2.90-2.75 (m,2H), 2.27 (s, 3H), 1.73 (s, 9H), 1.54 (t, J = 7.3 Hz, 3H)。

[0512] 1-110(#1):δ7.73-7.63 (m, 2H), 7.60-7.56 (m, 1H), 7.24-7.08 (m, 4H),6.93-6.84 (m, 1H), 6.80-6.54 (m, 4H), 5.42 (s, 2H), 3.69-3.58 (m, 2H), 3.37(s, 3H), 2.81 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 1.73 (s, 9H)。

[0513] 1-111(#1):δ7.69-7.59 (m, 2H), 7.53-6.97 (m, 6H), 6.56-6.37 (m, 3H),6.28-6.21 (m, 1H), 3.94 (s, 3H), 3.73-3.59 (m, 2H), 2.87-2.75 (m, 2H), 1.72(s, 9H)。

[0514] 1-112(#1):δ7.74-7.62 (m, 2H), 7.61-7.56 (m, 1H), 7.45-7.00 (m, 7H),6.62-6.54 (m, 1H), 6.53-6.36 (m, 1H), 5.42 (s, 2H), 3.73-3.59 (m, 2H), 3.37(s, 3H), 2.81 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。

[0515] 1-113(#1):δ7.69-7.59 (m, 2H), 7.44-7.00 (m, 8H), 6.52-6.35 (m, 2H),4.21 (q, J = 7.4 Hz, 2H), 3.72-3.58 (m, 2H), 2.80 (t, J = 7.0 Hz, 2H), 1.72(s, 9H), 1.53 (t, J = 7.4 Hz, 3H)。

[0516] 1-114(#1):δ7.99-7.89 (m, 2H), 7.76-7.66 (m, 1H), 7.57-7.50 (m, 1H),7.43-7.17 (m, 3H), 7.14 (s, 1H), 7.11-7.02 (m, 1H), 6.53-6.40 (m, 1H), 4.75(s, 2H), 4.18-4.07 (m, 2H), 3.57 (s, 3H), 2.87 (t, J = 7.0 Hz, 2H), 1.72 (s,9H)。

[0517] 1-115(#2):δ7.62-7.60 (m, 2H), 7.45-7.41 (m, 1H), 7.37-7.35 (m, 1H),7.31-7.29 (m, 2H), 7.21 (m, 2H), 7.15 (s, 1H), 7.11-7.08 (m, 1H), 6.54-6.51(m, 1H), 3.71-3.66 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 1.71 (s, 9H)。

[0518] 1-116(#2):δ7.89-7.87 (m, 2H), 7.47-7.32 (m, 2H), 7.27-7.21 (m, 3H),7.14 (s, 1H), 7.08-7.04 (m, 1H), 6.48-6.45 (m, 1H), 3.70-3.65 (m, 2H), 2.88-2.84 (m, 2H) 2.79 (s, 3H), 1.72 (s, 9H)。

[0519] 1-118(#2):δ7.81-7.78 (m, 2H), 7.40-7.29 (m, 2H), 7.25-7.23 (m, 2H),7.19 (m, 1H), 7.13 (s, 1H), 7.07-7.04 (m, 1H), 6.50-6.47 (m, 1H), 3.71-3.61(m, 2H), 2.87 (t, J = 6.8, 2H), 2.24-2.19 (m, 1H), 1.72 (s, 9H), 1.22-1.18(m, 4H)。

[0520] 1-119(#1):δ7.89-7.86 (m, 2H), 7.40-7.28 (m, 4H), 7.18 (m, 1H), 7.13(s, 1H), 7.07-7.02 (m, 1H), 6.51(m, 1H), 4.70 (s, 2H), 3.72-3.65 (m, 2H),3.50 (s, 3H), 2.90-2.86 (m, 2H), 1.71 (s, 9H)。

[0521] 1-120(#2):δ8.13-8.03 (m, 2H), 7.80-7.73 (m, 1H), 7.64-7.55 (m, 1H),7.39-7.35 (m, 4H), 7.33-7.27 (m, 3H), 7.14 (s, 1H), 7.09-7.03 (m, 1H), 6.53-6.46 (m, 1H), 3.75-3.65 (m, 2H), 2.93-2.84 (m, 2H), 1.72 (s, 9H)。

[0522] 1-121(#2):δ7.80-7.73 (m, 2H), 7.45-7.32 (m, 3H), 7.31-7.21 (m, 2H),7.14 (s, 1H), 7.12-7.03 (m, 1H), 6.54-6.43 (m, 1H), 3.74-3.61 (m, 2H), 2.93-2.81 (m, 2H), 2.71 (s, 3H), 1.71 (s, 9H)。

[0523] 1-123(#2):δ7.85-7.83 (m, 2H), 7.27-7.25 (m, 2H), 7.17-7.13 (m, 1H),7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.71 (m, 3H), 3.73-3.61 (m, 2H), 2.96(dd, J = 8.0, 14.4 Hz, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s,9H) 1.45 (t, J = 6.8 Hz, 3H)。

[0524] 1-124(#2):δ7.80-7.77 (m, 2H), 7.27-7.23 (m, 2H), 7.17-7.13 (m, 1H),7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.67 (m, 3H), 3.70-3.65 (m, 2H), 2.88-2.84 (m, 2H), 2.29 (s, 3H), 2.26-2.19 (m, 1H), 1.72 (s, 9H), 1.22-1.18 (m,4H)。

[0525] 1-126(#2):δ7.85-7.82 (m, 2H), 7.27-7.25 (m, 2H), 7.17-7.13 (m, 1H),7.10 (s, 1H), 6.88-6.87 (m, 1H), 6.73-6.67 (m, 3H), 3.70-3.65 (m, 2H), 2.94-2.86 (m, 4H), 2.29 (s, 3H), 1.92-1.86 (m, 2H), 1.72 (s, 9H), 1.07 (t, J = 7.2Hz, 3H)。

[0526] 1-128(#2):δ7.83-7.81 (m, 2H), 7.41-7.31 (m, 2H), 7.22-7.19 (m, 3H),7.14 (s, 1H), 7.06-7.03 (m, 1H), 6.47(m, 1H),5.17-5.13 (m, 1H) 3.73-3.63 (m,3H), 2.84 (t, J = 7.2 Hz, 2H), 2.12-2.08 (m, 2H),1.80-1.75 (m, 2H) 1.71 (s,9H), 1.50-1.19 (m, 6H)。

[0527] 1-129(#2):δ7.86-7.81 (m, 2H), 7.44-7.29 (m, 2H), 7.22-7.18 (m, 3H),7.15 (s, 1H), 7.06-7.00 (m, 1H), 6.49-6.38 (m, 1H), 3.72-3.63 (m, 6H), 2.99-2.82 (t, J = 6.8 Hz, 2H), 1.79-1.69 (m, 15H)。

[0528] 1-130(#2):δ7.95-7.92 (m, 2H), 7.41-7.37 (m, 1H), 7.33-7.30 (m, 1H),7.29-7.25 (m, 2H), 7.19 (s, 1H), 7.15-7.13 (s, 1H), 7.08-7.05 (m, 1H), 6.50-6.48 (m, 1H), 3.83-3.76 (m, 2H), 3.68 (dd, J = 12.8, 6.8 Hz, 2H), 3.63-3.60(m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.79-1.66 (m, 15H)。

[0529] 1-131(#2):δ7.70-7.62 (m, 2H), 7.49-7.09 (m, 7H), 7.08-7.01 (m, 1H),6.54-6.37 (m, 2H), 4.60-4.49 (m, 1H), 3.71-3.60 (m, 2H), 2.80 (t, J = 6.8 Hz,2H), 1.72 (s, 9H), 1.54 (d, J = 7.0 Hz, 6H)。

[0530] 1-132(#2):δ7.69-7.62 (m, 2H), 7.45-7.40 (m, 1H), 7.26-7.10 (m, 4H),6.99-6.62 (m, 4H), 6.50-6.44 (m, 1H), 4.60-4.49 (m, 1H), 3.68-3.59 (m, 2H),2.80 (t, J = 6.8 Hz, 2H), 2.27 (s, 3H), 1.73 (s, 9H), 1.54 (d, J = 7.0 Hz,6H)。

[0531] 1-135(#2):δ7.98-7.68 (m, 2H), 7.50-7.29 (m, 2H), 7.26-7.22 (m, 2H),7.20-7.12 (m, 2H), 7.11 (s, 1H), 7.06-6.87 (m, 1H), 6.51-6.39 (m, 1H), 3.73-3.46 (m, 2H), 3.13-3.02 (m, 3H), 3.00-2.80 (m, 2H), 1.67 (s, 9H)。

[0532] 1-136(#1):δ7.95-7.92 (m, 2H), 7.29-7.25 (m, 2H), 7.14-7.11 (m, 2H),6.80-6.97 (1H), 6.74 (s, 3H), 3.78-3.63 (m, 6H), 2.90-2.88 (m, 2H), 2.32-2.29(m, 3H), 1.75-1.73 (m, 15H)。

[0533] 1-137(#2):δ8.09-7.90 (m, 2H), 7.37-7.20 (m, 2H), 7.18-7.14 (m, 1H),7.10 (s, 1H), 7.00-6.84 (m, 1H), 6.74-6.72 (m, 3H), 3.80-3.74 (m, 2H), 3.72-3.60 (m, 4H), 2.88 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.70 (s, 15H)。

[0534] 1-138(#2):δ7.47-7.37 (m, 2H), 7.34-7.17 (m, 2H), 7.15-7.11 (s, 1H),6.97-6.88 (m, 1H), 6.74-6.60 (m, 3H), 3.67 (m, 3H), 2.90-2.81 (m, 2H), 2.35(m, 3H), 1.75(s, 12H)。

[0535] 1-139(#2): δ7.95-7.82 (m, 2H), 7.33-7.27 (m, 2H), 7.22-7.05 (m, 2H), 6.94-6.87 (m, 1H), 6.82-6.72 (m, 3H), 4.78-4.67 (s, 2H), 3.78-3.61 (m, 2H), 3.58-3.47 (s, 3H), 2.98-2.81 (m, 2H), 2.33-2.24 (s, 3H), 1.89-1.68 (s, 9H).

[0536] 1-140(#1):δ7.96-7.82 (m, 2H), 7.44-7.28 (m, 3H), 7.22-7.19 (m, 2H), 7.15-7.06 (m, 2H), 6.51-6.44 (m, 1H), 5.16-5.12 (m, 1H), 3.73-3.63(m, 2H),3.50(m, 2H), 2.91-2.82(m, 2H), 1.83-1.58(m, 9H), 1.52-1.24(m, 4H), 1.01-0.95(m, 3H)。

[0537] 1-143(#2):δ7.95-7.93 (m, 1H), 7.45-7.43 (m, 1H), 7.32-7.28 (m, 2H), 7.25-7.22 (m, 1H), 7.20-7.11 (m, 2H), 7.02-6.90 (m, 1H), 6.76-6.70 (m, 3H),3.73-3.65 (m, 2H), 3.13 (d, J = 4.8 Hz, 3H), 2.94-2.85 (m, 2H), 2.37-2.29 (m,3H), 1.79-1.68 (m, 9H)。

[0538] 1-144(#2):δ7.95-7.93 (m, 1H), 7.43-7.41 (m, 1H), 7.30-7.27 (m, 2H),7.25-7.21 (m, 1H), 7.19-7.12 (m, 2H), 7.01-6.89 (m, 1H), 6.75-6.73 (m, 3H),3.71-3.62 (m, 2H), 3.60-3.55 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.36-2.28 (m,3H), 1.74 (m, 9H), 1.36-1.22 (m, 3H)。

[0539] 1-146(#2):δ7.85-7.81 (m, 1H), 7.41-7.33 (m, 1H), 7.30-7.07 (m, 4H),6.99-6.87 (m, 1H), 6.73-6.65 (m, 3H), 5.16-5.15 (m, 1H), 3.69-3.62 (m, 2H),3.55-3.36 (m, 2H), 2.88-2.81 (m, 2H), 2.45-2.16 (m, 3H), 1.71 (s, 9H), 1.35-1.15 (m, 3H)。

[0540] 1-147(#2):δ7.94-7.90 (m, 1H), 7.42-7.40 (m, 1H), 7.29-7.12 (m, 3H),7.10 (s, 1H), 7.00-6.87 (m, 2H), 6.76-6.72 (m, 3H), 4.37-4.27 (m, 1H), 3.71-3.63 (m, 2H), 2.91-2.84 (m, 2H), 2.35-2.25 (m, 3H), 1.76-1.66 (m, 9H), 1.35-1.30 (m, 3H), 1.28-1.19 (m, 3H)。

[0541] 1-149(#1):δ7.74-7.66 (m, 2H), 7.24-7.08 (m, 4H), 6.92-6.84 (m, 1H),6.78-6.66 (m, 3H), 3.73-3.60 (m, 2H), 2.85 (t, J = 6.8 Hz, 2H), 2.48-2.37 (m,1H), 2.28 (s, 3H), 1.72 (s, 9H), 1.32-1.13 (m, 4H)。

[0542] 1-150(#2):δ7.94-7.91 (m, 2H), 7.35-7.26 (m, 2H), 7.23-7.10 (m, 2H),7.07-7.03 (m, 1H), 6.94-6.87 (m, 2H), 6.81-6.72 (m, 3H), 3.76-3.63 (dd, J =12.8, 6.8 Hz, 2H), 2.90-2.83 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.75 (s, 9H)。

[0543] 1-151(#2):δ7.86-7.81 (m, 2H), 7.20-7.12 (m, 4H), 6.98-6.89 (m, 1H),6.76-6.69 (m, 3H), 5.23 (br, 1H), 4.08-3.97 (m, 1H), 3.70-3.64 (m, 2H), 2.92-2.79 (m, 2H), 2.30 (s, 3H), 1.73 (s, 9H), 1.36-1.32 (m, 6H)。

[0544] 1-152(#2):δ7.84-7.79 (m, 2H), 7.38-7.19 (m, 3H), 7.17-7.02 (m, 2H),6.96-6.84 (m, 1H), 6.74-6.67 (m, 3H), 3.65 (dd, J = 12.8, 6.8 Hz, 2H), 2.89(t, J = 6.8 Hz, 2H), 2.59-2.36 (m, 3H), 2.30 (s, 3H), 1.71 (s, 9H)。

[0545] 1-153(#1):δ7.94-7.81 (m, 2H), 7.32-7.26 (m, 2H), 7.22-7.11 (m, 2H),6.99-6.87 (m, 2H), 6.74-6.72 (m, 3H), 4.16-3.99 (m, 1H), 3.71-3.62 (m, 2H),2.90-2.82 (t, J = 6.6 Hz, 2H), 2.35-2.30 (m, 3H), 2.09 (m, 1H), 1.73 (m,12H), 1.51-1.22 (m, 6H)。

[0546] 1-154(#1):δ7.94-7.91 (m, 1H), 7.43-7.40 (m, 1H), 7.29-7.19 (m, 4H),7.11 (s, 1H), 6.97-6.88 (m, 1H), 6.74-6.71 (m, 3H), 3.71-3.63 (m, 2H), 2.87(t, J = 6.6 Hz, 2H), 2.35-2.30 (m, 3H), 1.73 (s, 9H), 1.63-1.53 (m, 9H)。

[0547] 1-155(#1):δ7.84-7.81 (m, 2H), 7.23-7.11 (m, 4H), 6.91-6.88 (m, 1H),6.74-6.66 (m, 3H), 5.07-5.05 (m, 1H), 3.76-3.62 (m, 3H), 2.86 (t, J = 6.9 Hz,2H), 2.33 (s, 3H), 2.13-2.09 (m, 1H), 1.73 (m, 12H), 1.51-1.22 (m, 6H)。

[0548] 1-156(#1):δ7.85-7.82 (m, 2H), 7.22-7.12 (m, 4H), 6.91-6.88 (m, 1H),6.75-6.66 (m, 3H), 5.14 (s, 1H), 3.65 (dd, J = 12.8, 7.0 Hz, 2H), 3.15 (s,3H), 2.84 (t, J = 7.0 Hz, 2H), 2.31 (s, 3H), 1.76 (s, 9H)。

[0549] 1-157(#2):δ7.86-7.84 (m, 1H), 7.42-7.40 (m, 1H), 7.30-7.11 (m, 3H),7.00-6.89 (m, 2H), 6.75-6.67 (m, 3H), 3.69-3.62 (m, 6H), 3.02 (m, 1H), 2.89-2.82 (m, 2H), 2.33 (m, 3H), 1.66 (s, 12H)。

[0550] 1-158(#2):δ7.97-7.95 (m, 2H), 7.33-7.27 (m, 2H), 7.19-7.12 (m, 2H),6.90-6.89 (m, 1H), 6.75-6.73 (m, 3H), 4.00-3.97 (m, 2H), 3.77-3.66 (m, 4H),2.97-2.87 (m, 2H), 2.30 (s, 3H), 2.10-2.00 (m, 4H), 1.75 (s, 9H)。

[0551] 1-159(#2):δ7.91-7.89 (m, 2H), 7.42-7.11 (m, 4H), 6.90-6.88 (m, 1H),6.74-6.72 (m, 3H), 3.67 (dd, J = 12.8, 6.8 Hz, 2H), 2.87 (t, J = 6.8 Hz, 2H),2.35-2.05 (m, 8H), 1.57 (s, 9H)。

[0552] 1-161(#1):δ8.06-7.90 (m, 1H), 7.83-7.77 (m, 2H), 7.22-7.04 (m, 4H),6.92-6.84 (m, 1H), 6.79-6.70 (m, 3H), 3.68-3.61 (m, 2H), 3.48-3.36 (m, 4H),2.88-2.72 (m, 2H), 2.28 (s, 3H), 1.70 (s, 9H), 1.33-1.18 (m, 6H)。

[0553] 1-162(#1):δ7.97-7.93 (m, 2H), 7.29-7.27 (m, 2H), 7.20-7.12 (m, 2H),6.95-6.89 (m, 1H), 6.75-6.73 (m, 3H), 3.72-3.56 (m, 4H), 3.27-3.18 (m, 3H),2.90 (t, J = 6.6 Hz, 2H), 2.34 (s, 3H), 1.74 (s, 9H), 1.36-1.25 (m, 3H)。

[0554] 1-163(#1):δ7.93-7.81 (m, 2H), 7.35-7.07 (m, 4H), 6.96-6.87 (m, 1H),6.79-6.61 (m, 3H), 3.91-3.76 (m, 4H), 3.73-3.55 (m, 6H), 2.83 (t, J = 7.0 Hz,2H), 2.35 (s, 3H), 1.77 (s, 9H)。

[0555] 1-164(#1):δ7.86-7.79 (m, 2H), 7.43-7.08 (m, 5H), 6.93-6.87 (m, 1H),6.79-6.71 (m, 3H), 3.89 (s, 3H), 3.76-3.57 (m, 2H), 2.87 (t, J = 6.9 Hz, 2H),2.27 (s, 3H), 1.77 (s, 9H)。

[0556] 1-165(#1):δ7.92-7.90 (m, 2H), 7.28-7.25 (m, 2H), 7.21-7.06 (m, 2H),6.93-6.86 (m, 1H), 6.73-6.70 (m, 3H), 3.91-3.76 (m, 8H), 3.66 (dd, J = 12.8,6.9 Hz, 2H), 2.85 (t, J = 6.9 Hz, 2H), 2.29 (s, 3H), 1.70 (s, 9H)。

[0557] 1-166(#2):δ7.84-7.81 (m, 2H), 7.21-7.07 (m, 4H), 6.93-6.87 (m, 1H),6.73-6.64 (m, 3H), 3.67-3.54 (m, 4H), 3.16 (s, 3H), 2.87-2.79 (t, J = 6.8 Hz,2H), 2.23 (s, 3H), 1.77 (s, 9H), 1.31-1.23 (m, 3H)。

[0558] 1-167(#1):δ7.62-7.60 (m, 2H), 7.20-6.99 (m, 4H), 6.91-6.68 (m, 5H), 3.61-3.46 (m, 2H), 3.07 (s, 3H), 2.63-2.63 (m, 2H), 2.31-2.18 (m, 3H), 1.73-1.65 (m, 9H).

[0559] 1-169(#2): δ7.87-7.85 (m, 1H), 7.44-7.12 (m, 6H), 6.96-6.90 (m, 1H), 6.80-6.64 (m, 2H), 3.91 (s, 3H), 3.77-3.64 (m, 2H), 3.39 (s, 3H), 2.97-2.80 (m, 2H), 2.32 (s, 3H), 1.79 (s, 9H).

[0560] 1-170(#2): δ8.04-7.81 (m, 2H), 7.22-7.10 (m, 5H), 6.90-6.88 (m, 1H), 6.74-6.72 (m, 3H), 3.68-3.63 (m, 2H), 3.06 (s, 6H), 2.85 (t, J = 6.7 Hz, 2H), 2.31 (s, 3H), 1.75 (s, 9H).

[0561] 1-171(#1): δ7.98-7.88 (m, 2H), 7.31-7.23 (m, 2H), 7.21-7.08 (m, 2H), 6.95-6.84 (m, 1H), 6.81-6.67 (m, 3H), 3.75-3.61 (m, 2H), 3.31 (s, 3H), 3.20 (s, 3H), 2.94-2.82 (m, 2H), 2.30 (s, 3H), 1.74 (s, 9H).

[0562] 1-173(#2):δ7.94-7.91 (m, 2H), 7.30-7.24 (m, 4H), 7.13 (s, 1H), 7.12-7.05 (m, 1H), 6.95-6.92 (m, 2H), 6.68-6.65 (m, 1H), 4.16 (q, J = 7.6 Hz, 1H),3.70-3.64 (m, 2H), 2.86 (t, J = 7.2 Hz, 2H), 2.23 (s, 3H), 1.79 (d, J = 7.6Hz, 3H), 1.74 (s, 9H)。

[0563] 1-180(#2):δ7.94-7.91 (m, 2H), 7.41-7.20 (m, 5H), 7.15 (s, 1H), 7.09-7.05 (m, 1H), 6.50-6.6.45 (m, 1H), 3.90 (s, 2H), 3.72-3.65 (m, 2H), 2.87 (t,J = 7.2 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H)。

[0564] 1-185(#2):δ7.94-7.91 (m, 2H), 7.32-7.23 (m, 4H), 7.13 (s, 1H), 7.12-7.05 (m, 1H), 6.95-6.92 (m, 2H), 6.69-6.65 (m, 1H), 4.25 (q, J = 7.2 Hz, 1H),3.70-3.64 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 2.72-2.66 (m, 2H), 1.79 (d, J =7.2 Hz, 3H), 1.73 (s, 9H), 1.28 (t, J = 7.6 Hz, 3H)。

[0565] 1-187(#2):δ7.94-7.89 (m, 2H), 7.32-7.24 (m, 4H), 7.13 (s, 1H), 7.12-7.07 (m, 1H), 6.95-6.92 (m, 2H), 6.70-6.65 (m, 1H), 4.35-4.26 (m, 1H), 3.69-3.63 (m, 2H), 2.88-2.69 (m, 4H), 1.90 (t, J = 7.4 Hz, 3H), 1.73 (s, 9H),1.43-1.35 (m, 3H)。

[0566] 1-189(#2):δ7.93-7.89 (m, 2H), 7.32-7.25 (m, 4H), 7.13 (s, 1H), 7.12-7.08 (m, 1H), 6.95-6.92 (m, 2H), 6.72-6.66 (m, 1H), 4.67-4.62 (q, J = 7.2 Hz,1H), 3.71-3.64 (m, 2H), 3.34-3.22 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 1.99 (d,J = 7.6 Hz, 3H), 1.74 (s, 9H), 1.49 (t, J = 7.6 Hz, 3H)。

[0567] 1-193(#2):δ7.94-7.90 (m, 2H), 7.32-7.24 (m, 4H), 7.13 (s, 1H), 7.14-7.95 (m, 1H), 6.95-6.6.91 (m, 2H), 6.70-6.66 (m, 1H), 4.38-4.26 (m, 2H),3.71-3.64 (m, 2H), 3.03-2.84 (m, 4H),1.73 (s, 9H), 1.45 (t, J = 7.6 Hz, 3H)。

[0568] 1-194(#2):δ7.94-7.91 (m, 2H), 7.43-7.34 (m, 2H), 7.28-7.06 (m, 5H),6.51-6.47 (m, 1H), 4.40-4.27 (m, 2H), 3.74-3.68 (m, 2H), 3.03-2.87 (m, 4H),1.74 (s, 9H), 1.47 (t, J = 7.6 Hz, 3H)。

[0569] 1-197(#2):δ7.95-7.91 (m, 2H), 7.30-7.24 (m, 4H), 7.13 (s, 1H), 7.10-7.06 (m, 1H), 6.95-6.91 (m, 2H), 6.69-6.64 (m, 1H), 3.93 (t, J = 7.6 Hz, 1H),3.71-3.64 (m, 2H), 2.86 (t, J = 7.2 Hz, 2H), 2.24-2.07 (m, 5H), 1.74 (s, 9H),1.10 (t, J = 7.6 Hz, 3H)。

[0570] 1-198(#2):δ7.97-7.93 (m, 2H), 7.42-7.33 (m, 2H), 7.29-7.22 (m, 3H),7.17 (s, 1H), 7.11-7.07 (m, 1H), 6.50-6.46 (m, 1H), 3.96-3.91 (m, 1H), 3.73-3.67 (m, 2H), 2.89 (t, J = 6.8 Hz, 2H), 2.25-2.06 (m, 5H), 1.75 (s, 9H),1.14-1.08 (m, 3H)。

[0571] 1-199(#2):δ7.95-7.90 (m, 2H), 7.32-7.25 (m, 4H), 7.14 (s, 1H), 7.11-7.07 (m, 1H), 6.96-6.6.93 (m, 2H), 6.70-6.66 (m, 1H), 4.20-4.15 (m, 1H),3.70-3.64 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.63 (s, 3H), 2.46-2.20 (m, 2H),1.74 (s, 9H), 1.22-1.07 (m, 3H)。

[0572] 1-200(#2):δ7.87-7.83 (m, 2H), 7.34-6.99 (m, 7H), 6.43-6.39 (m, 1H),4.12-3.95 (m, 1H), 3.640-3.58 (m, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.56-2.54(m, 3H), 2.42-2.12 (m, 2H), 1.67 (s, 9H), 1.13-1.02 (m, 3H)。

[0573] 1-206(#2):δ7.88-7.83 (m, 2H), 7.34-6.99 (m, 7H), 6.43-6.39 (m, 1H),4.10-3.95 (m, 1H), 3.64-3.58 (m, 2H), 2.82-2.52 (m, 4H), 2.40-2.15 (m, 2H),1.66 (s, 9H), 1.35-1.25 (m, 3H), 1.13-0.97 (m, 3H)。

[0574] 1-207(#2):δ7.95-7.89 (m, 2H), 7.32-7.25 (m, 4H), 7.13 (s, 1H), 7.11-7.06 (m, 1H), 6.95-6.6.92 (m, 2H), 6.71-6.66 (m, 1H), 4.48-4.41 (m, 1H),3.72-3.63 (m, 2H), 3.31-3.09 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.61-2.36 (m,2H), 1.74 (s, 9H), 1.50-1.43 (m, 3H), 1.15-1.06 (m, 3H)。

[0575] 1-208(#2):δ7.86-7.83 (m, 2H), 7.33-6.98 (m, 7H), 6.44-6.39 (m, 1H),4.40-4.35 (m, 1H), 3.65-3.55 (m, 2H), 3.23-3.01 (m, 2H), 2.81 (t, J = 6.8 Hz,2H), 2.53-2.30 (m, 2H), 1.66 (s, 9H), 1.43-1.32 (m, 3H), 1.07-0.96 (m, 3H)。

[0576] 1-209(#2):δ7.94-7.91 (m, 2H), 7.35-7.22 (m, 5H), 7.13 (s, 1H), 7.10-7.07 (m, 1H), 6.95-6.92 (m, 1H), 6.68-6.65 (m, 1H), 3.70-3.62 (m, 2H), 2.88-2.82 (m, 4H), 1.73 (s, 9H), 1.11 (s, 9H)。

[0577] 1-210(#2):δ7.95-7.91 (m, 2H), 7.40-7.34 (m, 2H), 7.28-7.21 (m, 3H),7.16 (s, 1H), 7.09-7.05 (m, 1H), 6.48-6.45 (m, 1H), 3.72-3.65 (m, 2H), 2.89-2.84 (m, 4H), 1.73 (s, 9H), 1.22 (s, 9H)。

[0578] 1-211(#2):δ7.93-7.89 (m, 2H), 7.31-7.22 (m, 4H), 7.13 (s, 1H), 7.10-7.07 (m, 1H), 6.94-6.91 (m, 2H), 6.69-6.64 (m, 1H), 3.70-3.63 (m, 2H), 3.05-3.01 (m, 1H), 2.88-2.82 (t, J = 6.8 Hz, 2H), 2.14-2.12 (m, 2H), 1.91-1.85 (m,2H), 1.78-1.67 (m, 11H), 1.61-1.26 (m, 4H)。

[0579] 1-212(#2):δ7.95-7.91 (m, 2H), 7.42-7.27 (m, 2H), 7.27-7.21 (m, 3H),7.17 (s, 1H), 7.10-7.06 (m, 1H), 6.49-6.46 (m, 1H), 3.73-3.68 (m, 2H), 3.07-3.01 (m, 1H), 2.88 (t, J = 6.8 Hz, 2H), 2.16-2.13 (m, 2H), 1.91-1.87 (m, 2H),1.79-1.26 (m, 15H)。

[0580] 1-216(#2):δ7.91-7.87 (m, 2H), 7.40-7.33 (m, 2H), 7.28-7.19 (m, 3H),7.14 (s, 1H), 7.09-7.05 (m, 1H), 6.51-6.47 (m, 1H), 6.20-6.16 (m, 1H), 5.52-5.45 (m, 1H), 3.72-3.65 (m, 2H), 2.87 (t, J = 7.2 Hz, 2H), 2.11 (s, 3H), 1.73(s, 9H), 1.67-1.61 (m, 3H)。

[0581] 1-224(#2):δ7.82-7.74 (m, 2H), 7.25-7.18 (m, 2H), 7.14-7.11 (m, 2H),7.07 (s, 1H), 7.02-6.6.97 (m, 1H), 6.87-6.84 (m, 2H), 6.57-6.53 (m, 1H),3.60-3.54 (m, 2H), 3.14 (s, 6H), 2.75 (t, J = 7.2 Hz, 2H),1.65 (s, 9H)。

[0582] 1-226(#2):δ7.88-7.85 (m, 2H), 7.33-7.20 (m, 4H), 7.14 (s, 1H), 7.11-7.07 (m, 1H), 6.95-6.6.92 (m, 1H), 6.66-6.63 (m, 1H), 6.57-6.53 (m, 1H), 3.92(s, 3H), 3.69-3.63 (m, 2H), 3.41 (s, 3H), 2.84 (t, J = 7.2 Hz, 2H), 1.73 (s,9H)。

[0583] 1-259(#1):δ7.92 (d, J = 8.2 Hz, 2H), 7.35-7.20 (m, 4H), 7.12 (s, 1H),7.11-7.02 (m, 1H), 6.98-6.88 (m, 2H), 6.75-6.58 (m, 1H), 4.86-4.74 (m, 1H),3.74-3.54 (m, 4H), 2.85 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H), 1.67 (d, J = 6.8Hz, 3H), 1.27 (t, J = 7.0 Hz, 3H)。

[0584] 1-260(#2):δ7.52-6.75 (m, 11H), 3.59 (s, 2H), 2.74 (s, 2H), 2.32-2.26(m, 3H), 1.90-1.66 (m, 9H)。

[0585] 1-261(#2):δ7.93 (d, J = 7.7 Hz, 2H), 7.33-7.10 (m, 4H), 6.94-6.85 (m,1H), 6.80-6.67 (m, 3H), 4.80 (q, J = 6.6 Hz, 1H), 3.75-3.55 (m, 4H), 2.92-2.82 (m, 2H), 2.29 (s, 3H), 1.77-1.64 (m, 12H), 1.27 (t, J = 7.0 Hz, 3H)。

[0586] 1-262(#2):δ7.94 (d, J = 8.4 Hz, 2H), 7.31-7.10 (m, 3H), 6.96-6.84 (m,2H), 6.78-6.68 (m, 3H), 4.58 (t, J = 6.8 Hz, 1H), 3.72-3.51 (m, 4H), 2.87 (t,J = 7.0 Hz, 2H), 2.29 (s, 3H), 2.08-1.97 (m, 2H), 1.73 (s, 9H), 1.26 (t, J =7.0 Hz, 3H), 1.02 (t, J = 7.3 Hz, 3H)。

[0587] 1-264(#2):δ7.89-7.87(m, 2H), 7.26-7.08(m, 4H), 6.94-6.89(m, 1H),6.75-6.69(m, 3H), 3.98(s, 3H), 3.75-3.66(m, 2H), 3.59(s, 3H), 2.88-2.83(m, 2H), 2.33(s, 3H), 1.56(s, 9H)。

[0588] 1-265(#2):δ8.02-7.79 (m, 2H), 7.38-7.09 (m, 7H), 6.95-6.89 (m, 1H), 6.78-6.70 (m, 2H), 3.70-3.64 (m, 2H), 3.05-3.00 (m, 2H), 2.90-2.83 (m, 3H), 2.33-2.20 (m, 3H), 1.75 (s, 9H).

[0589] 1-266(#2):δ7.94-7.87 (m, 2H), 7.31-7.10 (m, 6H), 7.00-6.73 (m, 4H), 3.71-3.63 (m, 2H), 2.91-2.82 (m, 2H), 2.35-2.18 (m, 3H), 1.71 (s, 9H).

[0590] 1-267(#1): δ7.96-7.84 (m, 2H), 7.36-7.21 (m, 2H), 7.21-7.05 (m, 2H), 6.97-6.83 (m, 1H), 6.82-6.61 (m, 3H), 4.70-4.54 (m, 1H), 3.74-3.62 (m, 2H), 3.13 (s, 3H), 2.88 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.98 (d, J = 7.2 Hz, 3H), 1.73 (s, 9H).

[0591] 1-268(#1):δ7.95-7.86 (m, 2H), 7.31-7.22 (m, 2H), 7.21-7.10 (m, 2H),6.93-6.85 (m, 1H), 6.79-6.66 (m, 3H), 4.64 (q, J = 7.4 Hz, 1H), 3.74-3.61 (m,2H), 3.39-3.16 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.98 (d, J =7.4 Hz, 3H), 1.73 (s, 9H), 1.48 (t, J = 7.5 Hz, 3H)。

[0592] 1-271(#2):δ7.89-7.86 (m, 1H), 7.52-7.40 (m, 1H), 7.30-7.11 (m, 5H),7.00-6.89 (m, 1H), 6.76-6.69 (m, 2H), 3.71-3.64 (m, 2H), 3.53 (s, 3H), 2.87(t, J = 6.7 Hz, 2H), 2.71 (s, 3H), 2.32 (s, 3H), 1.57 (s, 9H)。

[0593] 1-272(#2):δ7.91-7.77 (m, 2H), 7.53-7.07 (m, 6H), 6.93-6.70 (m, 4H),3.69-3.62 (m, 2H), 2.90-2.81 (m, 2H), 2.25 (s, 3H), 1.77-1.67 (m, 9H)。

[0594] 1-273(#1):δ7.97-7.86 (m, 2H), 7.30-7.09 (m, 4H), 6.93-6.84 (m, 1H),6.80-6.66 (m, 3H), 4.14 (q, J = 7.2 Hz, 1H), 3.74-3.60 (m, 2H), 2.86 (t, J =6.8 Hz, 2H), 2.29 (s, 3H), 2.21 (s, 3H), 1.78 (d, J = 7.2 Hz, 3H), 1.73 (s,9H)。

[0595] 1-274(#1):δ7.97-7.88 (m, 2H), 7.30-7.09 (m, 4H), 6.92-6.84 (m, 1H),6.78-6.65 (m, 3H), 4.23 (q, J = 7.4 Hz, 1H), 3.72-3.61 (m, 2H), 2.86 (t, J =7.0 Hz, 2H), 2.76-2.60 (m, 2H), 2.29 (s, 3H), 1.77 (d, J = 7.5 Hz, 3H), 1.73(s, 9H), 1.27 (t, J = 7.4 Hz, 3H)。

[0596] 1-275(#2):δ7.97-7.94 (m, 2H), 7.26-7.11 (m, 4H), 6.94-6.70 (m, 4H),4.19 (s, 3H), 3.71-3.64 (m, 2H), 2.93-2.76 (m, 4H), 2.32 (s, 3H), 1.71 (s,9H), 1.31-1.16 (m, 3H)。

[0597] 1-276(#2):δ7.97-7.87 (m, 2H), 7.30-7.22 (m, 2H), 7.21-7.09 (m, 2H),6.93-6.86 (m, 1H), 6.79-6.67 (m, 3H), 3.89 (s, 2H), 3.73-3.62 (m, 2H), 2.87(t, J = 7.0 Hz, 2H), 2.29 (s, 6H), 1.73 (s, 9H)。

[0598] 1-277(#2):δ7.97-7.88 (m, 2H), 7.30-7.22 (m, 2H), 7.21-7.09 (m, 2H),6.93-6.86 (m, 1H), 6.80-6.68 (m, 3H), 3.93 (s, 2H), 3.71-3.63 (m, 2H), 2.87(t, J = 7.0 Hz, 2H), 2.73 (q, J = 7.3 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H),1.33 (t, J = 7.3 Hz, 3H)。

[0599] 1-278(#1):δ7.97-7.87 (m, 2H), 7.31-7.10 (m, 4H), 6.95-6.85 (m, 1H),6.82-6.65 (m, 3H), 4.45-4.27 (m, 2H), 3.79-3.60 (m, 2H), 2.96-2.81 (m, 5H),2.31 (s, 3H), 1.74 (s, 9H)。

[0600] 1-279(#1):δ7.96-7.87 (m, 2H), 7.31-7.08 (m, 4H), 6.94-6.85 (m, 1H),6.80-6.65 (m, 3H), 4.41-4.22 (m, 2H), 3.73-3.59 (m, 2H), 3.06-2.80 (m, 4H),2.30 (s, 3H), 1.73 (s, 9H), 1.44 (t, J = 7.5 Hz, 3H)。

[0601] 1-280(#1):δ7.95-7.86 (m, 2H), 7.34-7.08 (m, 4H), 6.91-6.84 (m, 1H),6.78-6.66 (m, 3H), 4.64 (s, 2H), 3.74-3.59 (m, 2H), 3.24 (s, 3H), 2.93-2.82(m, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。

[0602] 1-281(#1):δ7.93-7.85 (m, 2H), 7.30-7.21 (m, 2H), 7.21-7.08 (m, 2H),6.93-6.84 (m, 1H), 6.82-6.68 (m, 3H), 4.61 (s, 2H), 3.76-3.60 (m, 2H), 3.34(q, J = 7.5 Hz, 2H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H),1.52 (t, J = 7.5 Hz, 3H)。

[0603] 1-282(#2):δ7.94-7.92 (m, 1H), 7.84-7.82 (m, 1H), 7.33-7.08 (m, 5H), 6.98-6.86 (m, 1H), 6.80-6.67 (m, 3H), 3.95-3.88 (m, 3H), 3.64 (s, 2H), 2.89-2.78 (m, 2H), 2.26 (s, 3H), 1.71 (s, 9H)。

[0604] 1-283(#2):δ7.96-7.88 (m, 2H), 7.29-7.08 (m, 4H), 6.93-6.86 (m, 1H), 6.80-6.67 (m, 3H), 4.20-4.08 (m, 1H), 3.72-3.62 (m, 2H), 2.91-2.82(m, 2H),2.30(s, 3H), 1.73(s, 9H), 1.36-1.20(m, 3H)。

[0605] 1-285(#2): δ7.95-7.85 (m, 2H), 7.31-7.23 (m, 2H), 7.21-7.08 (m, 2H), 6.94-6.87 (m, 1H), 6.79-6.68 (m, 3H), 4.13 (s, 2H), 3.75-3.62 (m, 2H), 2.88 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H), 1.73 (s, 9H).

[0606] 1-288(#1): δ7.95-7.86 (m, 2H), 7.31-7.08 (m, 3H), 6.94-6.84 (m, 2H), 6.80-6.65 (m, 3H), 3.74-3.60 (m, 2H), 2.86 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H), 1.49 (s, 9H).

[0607] 1-289(#1):δ7.95-7.85 (m, 2H), 7.36-7.17 (m, 4H), 7.15-7.01 (m, 2H),6.99-6.86 (m, 2H), 6.73-6.59 (m, 1H), 3.73-3.59 (m, 2H), 2.84 (t, J = 7.0 Hz,2H), 1.72 (s, 9H), 1.50 (s, 9H)。

[0608] 1-291(#1):δ7.97-7.86 (m, 2H), 7.30-7.22 (m, 2H), 7.19-7.07 (m, 2H),6.94-6.83 (m, 1H), 6.80-6.65 (m, 3H), 3.77-3.60 (m, 2H), 2.89 (t, J = 6.8 Hz,2H), 2.28 (s, 3H), 1.73 (s, 9H), 1.44 (s, 9H)。

[0609] 1-292(#1):δ7.96-7.86 (m, 2H), 7.32-7.21 (m, 4H), 7.14-6.99 (m, 2H),6.96-6.86 (m, 2H), 6.75-6.60 (m, 1H), 3.79-3.59 (m, 2H), 2.87 (t, J = 6.8 Hz,2H), 1.73 (s, 9H), 1.44 (s, 9H)。

[0610] 1-293(#1):δ7.99-7.90 (m, 2H), 7.50-7.25 (m, 5H), 7.24-7.18 (m, 1H),7.15 (s, 1H), 7.12-7.03 (m, 1H), 3.78-3.63 (m, 2H), 2.90 (t, J = 6.8 Hz, 2H),2.68 (d, J = 7.2 Hz, 2H), 2.31-2.15 (m, 1H), 1.73 (s, 9H), 1.04 (d, J = 6.5Hz, 6H)。

[0611] 1-294(#1):δ7.96-7.86 (m, 2H), 7.33-7.22 (m, 2H), 7.21-7.06 (m, 2H),6.94-6.83 (m, 1H), 6.82-6.65 (m, 3H), 3.75-3.63 (m, 2H), 2.89 (t, J = 6.6 Hz,2H), 2.67 (d, J = 7.2 Hz, 2H), 2.35-2.14 (m, 4H), 1.73 (s, 9H), 1.03 (d, J =6.5 Hz, 6H)。

[0612] 1-295(#1):δ7.97-7.87 (m, 2H), 7.32-7.21 (m, 4H), 7.14-7.01 (m, 2H),6.96-6.86 (m, 2H), 6.76-6.62 (m, 1H), 3.75-3.61 (m, 2H), 2.88 (t, J = 6.8 Hz,2H), 2.67 (d, J = 7.2 Hz, 2H), 2.30-2.15 (m, 1H), 1.72 (s, 9H), 1.03 (d, J =6.8 Hz, 6H)。

[0613] 1-296(#1):δ7.93-7.82 (m, 2H), 7.50-7.00 (m, 7H), 6.93-6.76 (m, 1H),5.83-5.67 (m, 1H), 3.78-3.66 (m, 2H), 3.05-2.85 (m, 4H), 1.57-1.41 (m, 9H)。

[0614] 1-297(#1):δ7.95-7.82 (m, 2H), 7.37-6.84 (m, 9H), 5.85-5.67 (m, 1H),3.79-3.63 (m, 2H), 2.98 (q, J = 7.6 Hz, 2H), 2.89 (t, J = 6.8 Hz, 2H), 1.55-1.43 (m, 9H)。

[0615] 1-298(#1):δ8.49-8.39 (m, 1H), 7.96-7.79 (m, 3H), 7.72-7.61 (m, 1H),7.51-7.12 (m, 8H), 6.96-6.77 (m, 1H), 3.76-3.63 (m, 2H), 2.97 (q, J = 7.6 Hz,2H), 2.89 (t, J = 6.8 Hz, 2H), 1.46 (t, J = 7.7 Hz, 3H)。

[0616] 1-301(#2):δ8.00-7.91 (m, 2H), 7.44-7.18 (m, 5H), 7.15 (s, 1H), 7.11-7.04 (m, 1H), 6.59-6.44 (m, 1H), 4.50 (t, J = 6.6 Hz, 1H), 3.73-3.63 (m, 2H),3.46 (s, 3H), 2.87 (t, J = 6.8 Hz, 2H), 2.11-1.97 (m, 2H), 1.72 (s, 9H), 1.02(t, J = 7.5 Hz, 3H)。

[0617] 1-302(#2):δ7.96-7.87 (m, 2H), 7.49-7.28 (m, 2H), 7.27-7.18 (m, 3H),7.15 (s, 1H), 7.11-7.03 (m, 1H), 6.54-6.43 (m, 1H), 3.98-3.88 (m, 1H), 3.72-3.64 (m, 2H), 3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.09-3.00 (m, 1H), 2.86 (t, J= 7.0 Hz, 2H), 1.72 (s, 9H), 1.31 (d, J = 6.2 Hz, 3H)。

[0618] 1-303(#2):δ7.98-7.91 (m, 2H), 7.30-7.21 (m, 2H), 7.20-7.10 (m, 2H),6.92-6.86 (m, 1H), 6.78-6.68 (m, 3H), 4.50 (t, J = 6.6 Hz, 1H), 3.71-3.63 (m,2H), 3.46 (s, 3H), 2.87 (t, J = 7.0 Hz, 2H), 2.29 (s, 3H), 2.10-1.97 (m, 2H),1.73 (s, 9H), 1.02 (t, J = 7.5 Hz, 3H)。

[0619] 1-304(#2):δ7.96-7.88 (m, 2H), 7.30-7.09 (m, 4H), 6.94-6.86 (m, 1H),6.78-6.66 (m, 3H), 3.98-3.89 (m, 1H), 3.73-3.62 (m, 2H), 3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.08-3.00 (m, 1H), 2.86 (t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73(s, 9H), 1.31 (d, J = 6.2 Hz, 3H)。

[0620] 1-305(#2):δ7.99-7.90 (m, 2H), 7.35-7.22 (m, 4H), 7.13 (s, 1H), 7.12-7.03 (m, 1H), 6.97-6.89 (m, 2H), 6.73-6.63 (m, 1H), 4.50 (t, J = 6.6 Hz, 1H),3.72-3.62 (m, 2H), 3.46 (s, 3H), 2.85 (t, J = 7.0 Hz, 2H), 2.11-1.98 (m, 2H),1.73 (s, 9H), 1.02 (t, J = 7.5 Hz, 3H)。

[0621] 1-306(#2):δ7.95-7.87 (m, 2H), 7.34-7.20 (m, 4H), 7.15-7.03 (m, 2H),6.97-6.87 (m, 2H), 6.75-6.61 (m, 1H), 3.98-3.88 (m, 1H), 3.71-3.61 (m, 2H),3.37 (s, 3H), 3.24-3.15 (m, 1H), 3.08-2.99 (m, 1H), 2.85 (t, J = 6.8 Hz, 2H),1.72 (s, 9H), 1.32 (d, J = 6.2 Hz, 3H)。

[0622] 1-307(#1):δ8.16 (s, 1H), 7.96-7.93 (m, 2H), 7.28-7.11 (m, 4H), 6.97-6.87 (m, 1H), 6.74-6.72 (m, 3H), 4.26 (s, 3H), 3.71-3.64 (m, 2H), 2.96-2.85(m, 2H), 2.32 (s, 3H), 1.72 (s, 9H)。

[0623] 1-308(#1):δ8.73 (s, 1H), 7.99-7.89 (m, 2H), 7.46-7.00 (m, 7H), 6.58-6.40 (m, 1H), 3.74-3.62 (m, 2H), 2.87 (t, J = 7.0 Hz, 2H), 1.72 (s, 9H)。

[0624] 1-309(#1):δ8.73 (s, 1H), 7.99-7.89 (m, 2H), 7.32-7.21 (m, 2H), 7.20-7.06 (m, 2H), 6.94-6.83 (m, 1H), 6.81-6.63 (m, 3H), 3.74-3.62 (m, 2H), 2.87(t, J = 6.8 Hz, 2H), 2.29 (s, 3H), 1.73 (s, 9H)。

[0625] 1-313(#2):δ8.00-7.89 (m, 2H), 7.41-7.06 (m, 4H), 6.94-6.82 (m, 1H),6.80-6.73 (m, 3H), 6.29 (s, 1H), 5.52-5.45 (m, 1H), 3.74-3.62 (m, 2H), 2.93-2.83 (m, 2H), 2.31 (s, 3H), 2.20-2.02 (m, 3H), 1.85-1.74 (m, 9H), 1.33-1.11(m, 3H)。

[0626] 1-314(#1):δ7.93-7.80 (m, 2H), 7.49-7.03 (m, 7H), 6.88-6.69 (m, 1H),4.22 (s, 3H), 3.79-3.65 (m, 2H), 2.98 (q, J = 7.6 Hz, 2H), 2.90 (t, J = 6.8Hz, 2H), 1.46 (t, J = 7.7 Hz, 3H)。

[0627] 1-320(#1):δ7.99-7.96 (m, 2H), 7.27-7.24 (m, 2H), 7.18-7.11 (m, 2H),6.91-6.86 (m, 1H), 6.74-6.72 (m, 3H), 4.40 (s, 3H), 3.67 (dd, J = 12.8, 7.0Hz, 2H), 2.86 (t, J = 7.0 Hz, 2H), 2.25 (s, 3H), 1.68 (d, J = 26.2 Hz, 9H)。

[0628] 1-321(#1):δ7.99-7.96 (m, 2H), 7.30-7.24 (m, 4H), 7.13-7.00 (m, 2H),6.94-6.91 (m, 2H), 6.65 (s, 1H), 4.40 (s, 3H), 3.70-3.63 (m, 2H), 2.85 (t, J= 6.8 Hz, 2H), 1.72 (s, 9H)。

[0629] 1-322(#1): δ7.96-7.93 (m, 2H), 7.39-7.03 (m, 8H), 4.38 (s, 3H), 3.70-3.63 (m, 2H), 2.84 (t, J = 6.8 Hz, 2H), 1.66 (s, 9H).

[0630] 1-323(#1): δ7.99-7.97 (m, 2H), 7.33-6.98 (m, 5H), 6.95-6.83 (m, 1H), 6.79-6.72 (m, 2H), 4.74-4.67 (m, 2H), 3.71-3.64 (m, 2H), 2.93-2.80 (m, 2H), 2.27 (s, 3H), 1.79-1.54 (m, 12H).

[0631] 1-324(#1):δ8.04-7.96 (m, 2H), 7.49-6.91 (m, 8H), 6.75-6.65 (m, 1H),4.74-4.67 (m, 2H), 3.72-3.63 (m, 2H), 2.91-2.82 (m, 2H), 1.69-1.77(m, 12H)。

[0632] 1-325(#1):δ8.12-7.96(m, 2H), 7.52-7.05(m, 7H), 6.48(s, 1H), 4.74-4.66(m, 2H), 3.76-3.65(m, 2H), 2.94-2.80(m, 2H), 1.91-1.54(m, 12H)。

[0633] 1-330(#1): δ7.93-7.91 (m, 2H), 7.27-7.11 (m, 3H), 7.03-6.87 (m, 2H), 6.79-6.72 (m, 3H), 3.71-3.64 (m, 2H), 2.90-2.80 (m, 2H), 2.35-2.33 (m, 1H), 2.29 (s, 3H), 1.94-1.80 (m, 3H), 1.74 (s, 9H).

[0634] 1-331(#1): δ7.98-7.91 (m, 2H), 7.46-7.01 (m, 6H), 6.94-6.91 (m, 2H), 6.67-6.65 (m, 1H), 5.97-5.75 (m, 1H), 3.70-3.63 (m, 2H), 2.88-2.80 (m, 2H), 1.94-1.84 (m, 3H), 1.76 (s, 9H).

[0635] 1-336(#1): δ7.95-7.82 (m, 2H), 7.42-7.00 (m, 6H), 6.97-6.85 (m, 2H), 6.83-6.66 (m, 1H), 4.10 (s, 3H), 3.78-3.59 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H).

[0636] 1-337(#1):δ7.92-7.81 (m, 2H), 7.33-6.66 (m, 8H), 4.10 (s, 3H), 3.76-3.60 (m, 2H), 2.89 (t, J = 6.6 Hz, 2H), 2.29 (s, 3H), 1.72 (s, 9H).

[0637] 1-338(#1): δ7.97-7.86 (m, 2H), 7.32-7.08 (m, 5H), 7.07-6.66 (m, 7H), 5.31 (s, 2H), 3.77-3.58 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.28 (s, 3H), 1.72 (s, 9H).

[0638] 1-339(#1):δ7.95-7.84 (m, 2H), 7.36-7.05 (m, 7H), 7.04-6.92 (m, 2H),6.88-6.60 (m, 4H), 5.63 (q, J = 6.6 Hz, 1H), 3.75-3.56 (m, 2H), 2.86 (t, J =6.6 Hz, 2H), 2.26 (s, 3H), 1.86 (d, J =6.6 Hz, 3H), 1.72 (s, 9H)。

[0639] 1-341(#1):δ8.00-7.97 (m, 2H), 7.33-7.12 (m, 5H), 6.95-6.86 (m, 1H),6.79-6.72 (m, 2H), 3.71-3.64 (m, 2H), 2.93-2.84 (m, 2H), 2.28 (s, 3H), 2.20-1.99 (m, 2H), 1.76 (s, 9H), 1.58-1.51 (m, 3H), 1.04-0.91 (m, 2H)。

[0640] 1-342(#1):δ7.98 (d, J = 8.2 Hz, 2H), 7.48-7.20 (m, 5H), 7.15-6.91 (m,4H), 4.64-4.60 (m, 2H), 3.70-3.63 (m, 2H), 2.91-2.83 (m, 2H), 2.17-2.05 (m,2H), 1.69 (s, 9H), 1.06-0.88 (m, 3H)。

[0641] 1-343(#1):δ8.09-7.96 (m, 2H), 7.54-7.05 (m, 7H), 6.47-6.45 (m, 1H),4.64-4.59 (m, 2H), 3.73-3.63 (m, 2H), 2.91-2.84 (m, 2H), 2.16-2.05 (m, 2H),1.67 (s, 9H), 1.06-0.94 (m, 3H)。

[0642] 1-344(#1):δ8.00-7.97 (m, 2H), 7.46-7.12 (m, 4H), 6.98-6.81 (m, 1H),6.74-6.72 (m, 3H), 5.16-5.07 (m, 1H), 3.71-3.64 (m, 2H), 3.02-2.84 (m, 2H),2.31 (s, 3H), 1.82-1.50 (m, 15H)。

[0643] 1-345(#2):δ7.99-7.97 (m, 2H), 7.46-7.20 (m, 4H), 7.17-7.03 (m, 2H),6.98-6.91 (m, 2H), 6.66 (s, 1H), 5.16-5.07 (m, 1H), 3.70-3.63 (m, 2H), 2.91-2.82 (m, 2H), 1.83-1.55 (m, 15H)。

[0644] 1-346(#1):δ8.13-7.96 (m, 2H), 7.49-7.05 (m, 7H), 6.47 (s, 1H), 5.16-5.06 (m, 1H), 3.72-3.63 (m, 2H), 3.01-2.81 (m, 2H), 1.77-1.51 (m, 15H)。

[0645] 1-347(#2):δ7.81-7.72 (m, 2H), 7.25-7.18 (m, 4H), 7.13 (s, 1H), 7.07-7.00 (m, 1H), 6.87-6.84 (m, 2H), 6.56-6.52 (m, 1H), 3.62-3.53 (m, 6H), 2.75(t, J = 6.8 Hz, 2H),1.67-1.60 (m, 15H)。

[0646] 1-348(#1):δ7.89 (d, J = 7.8 Hz, 2H), 7.37-7.23 (m, 7H), 7.14 (s, 1H),7.07-7.04 (m, 1H), 6.97-6.87 (m, 3H), 6.48-6.45 (m, 1H), 4.14-4.10 (m, 2H),3.70-3.63 (m, 2H), 3.17 (t, J = 7.5 Hz, 2H), 2.92-2.78 (m, 2H), 2.46-2.30 (m,2H), 1.72 (s, 9H)。

[0647] 1-349(#1):δ7.89 (d, J = 17.7 Hz, 2H), 7.38-7.31 (m, 2H), 7.25-7.19(m, 5H), 7.14 (s, 1H), 7.08-7.02 (m, 3H), 6.48-6.45 (m, 1H), 3.71-3.64 (m,2H), 3.27-3.23 (m, 4H), 2.90-2.82 (m, 2H), 1.72 (s, 9H)。

[0648] 2-001(#2):δ7.93 (s, 1H), 7.42-7.31 (m, 2H), 7.27-7.15 (m, 4H), 7.13-7.06 (m, 1H), 7.03-6.98 (m, 1H), 6.59-6.49 (m, 1H), 3.97 (s, 3H), 3.86 (s,3H), 3.67-3.58 (m, 2H), 2.87 (t, J = 6.8 Hz, 2H), 1.72 (s, 9H)。

[0649] 2-002(#2):δ8.05 (s, 1H), 7.58-7.52 (m, 2H), 7.41-7.27 (m, 2H), 7.23-7.02 (m, 4H), 6.62-6.51 (m, 1H), 3.98 (s, 3H), 3.88 (s, 3H), 3.66-3.56 (m,2H), 2.85 (t, J = 6.6 Hz, 2H), 1.71 (s, 9H)。

[0650] 2-003(#1):δ7.56-7.45 (m, 2H), 7.31-7.22 (m, 3H), 7.20-7.07 (m, 3H),6.95-6.83 (m, 1H), 3.89 (s, 3H), 3.71-3.60 (m, 2H), 2.91-2.85 (m, 2H), 2.46(s, 3H), 2.26 (s, 3H), 1.74 (s, 9H)。

[0651] 2-004(#2):δ7.56-7.37 (m, 2H), 7.34-7.22 (m, 3H), 7.21-7.08 (m, 3H), 6.96-6.85 (m, 1H), 3.86 (s, 3H), 3.70-3.54 (m, 2H), 3.01-2.83 (m, 2H), 2.29 (s, 3H), 2.21-2.08 (m, 1H), 1.70 (s, 9H), 1.18-0.98 (m, 4H).

[0652] ―――――――――――――――――――――――――――――― [Experimental Example] Next, the usefulness of the compounds of the present invention as pest control agents will be specifically illustrated in the following test examples, but the present invention is not limited thereto. Here, "RH" in the test examples refers to relative humidity, for example, "100%RH" means a relative humidity of 100%.

[0653] (Preparation of the test drug solution) The compound of the present invention was dissolved in a mixture of an emulsified white sample (Solpol 3005XL (manufactured by Toho Chemical Co., Ltd.), N-methylpyrrolidone, and Solvesso 200 (manufactured by Exon Mobil) [1:5:28 (weight ratio)] to prepare emulsions with concentrations of 1%, 5%, and 20% by mass. These emulsions were used as test solutions in the following test examples 1 to 7.

[0654] Experimental Example 1. Effect of wheat hull blight control on wheat control At 90cm 3 Wheat (variety: HARAYUTAKA) was planted in plastic containers. At the 1.3-leaf stage, the test pesticide solution was diluted with water to prepare a 500ppm solution, and 5ml was sprayed on each container. One day after spraying, a suspension of conidial spores of *Septorianodorum*, the wheat scab pathogen, was sprayed onto the wheat and placed in an inoculation chamber at 20°C and 100% RH for 2 days. Afterward, it was placed in an air-conditioned greenhouse (20°C, 80% RH) for 8 days. The proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the following formula.

[0655] Control value = [1 - (lesion area ratio in treated area / lesion area ratio in untreated area)] × 100 As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0656] Compound No.: 1-001, 1-003, 1-004, 1-005, 1-006, 1-008, 1-009, 1-010, 1-011, 1-012, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-022, 1-023, 1-024, 1-0 25, 1-026, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1-044, 1-045, 1-046, 1-047, 1- 048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-071, 1-073, 1-075, 1-076, 1-077, 1-078, 1-079, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086, 1-088, 1-089, 1-090, 1-092, 1-094, 1-095, 1-096, 1-097 , 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-124, 1-125, 1-126, 1-1 27, 1-129, 1-132, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-145, 1-146, 1-148, 1-149, 1-150, 1-154, 1-155, 1-156, 1-157, 1- 158, 1-159, 1-160, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1 -185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205,1-206, 1-207, 1-208, 1-210, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-300, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311, 1-312, 1-313, 1-314, 1-315, 1-316, 1-317, 1-318, 1-319 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0657] Experimental Example 2. Effect of Powdery Mildew Control on Tomatoes At 90cm 3 Tomatoes (variety: Momotaro) were planted in plastic containers. At the two-leaf stage, the experimental pesticide solution was diluted with water to prepare a 500ppm solution, and 5ml of the solution was sprayed on the plants. After air drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20℃, humidity 70%RH) and sprayed with a suspension of conidial spores of tomato powdery mildew fungus (Leveillula taurica). After 14 days, the proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Experiment 1.

[0658] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0659] Compound No.: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-0 20, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1- 043, 1-044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-059, 1-060, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-071, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086, 1-088, 1-089, 1-090, 1-091, 1-094 , 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-1 15, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-134, 1-135, 1-136, 1- 137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1 -159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-179, 1-180, 1-181,1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-208, 1-209, 1-210, 1-211, 1 -212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-2 76, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-298, 1-301, 1-302, 1-303, 1-304, 1-307, 1-308, 1-30 9, 1-310, 1-313, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-348, 1-349.

[0660] Experimental Example 3. Experiment on the control effect of gray mold in cucumber At 90cm 3 Cucumbers (variety: Sagami Hanshiro) were planted in plastic containers. During the cotyledon stage, 5 ml of a 500 ppm solution of the experimental pesticide was diluted with water and sprayed onto the affected leaves, which were then air-dried. Afterward, the treated leaves were cut off and placed in plastic containers. A suspension of conidia of *Botrytis cinerea* (the causal agent of cucumber gray mold) was mixed with dissolved PDA medium at a 1:1 (volume ratio), and 30 μl was applied to each treated leaf for inoculation. After inoculation, the plants were placed at 20°C and humid (100% RH) for 3 days. The proportion of lesions on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Experiment 1.

[0661] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0662] Compound No.: 1-001, 1-002, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-0 20, 1-021, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1- 042, 1-043, 1-044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083 , 1-084, 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-1 04, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1- 125, 1-126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1 -146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-152, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166,1-167, 1-168, 1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311 1-312, 1-313, 1-314, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0663] Experiment Example 4. Effect of Cucumber Sclerotinia stem rot control test At 90cm 3Cucumbers (variety: Sagami Hanshiro) were planted in plastic containers. During the cotyledon stage, 5 ml of a 500 ppm solution of the test pesticide was diluted with water and sprayed onto the cotyledons, which were then air-dried. The treated leaves were then placed in plastic containers. Agar plates (5 mm in diameter) containing Sclerotinia sclerotiorum, pre-cultured on PDA medium, were inoculated onto the pesticide-treated cotyledons. After inoculation, the plastic containers were covered with ethylene plastic film for humidification (100% RH) and placed at 20°C for 2 days. The proportion of lesions on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Experiment 1.

[0664] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0665] Compound No.: 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1- 043, 1-044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084 , 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-1 05, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1- 126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1 -147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-167, 1-168,1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-217, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-260, 1-261, 1-262, 1-263, 1-264, 1-265, 1-266, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276, 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-297, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-311 1-312, 1-313, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0666] Experimental Example 5. Experiment on the control effect of cucumber powdery mildew. At 90cm 3Cucumbers (variety: Sagami Hanshiro) were planted in plastic containers. During the cotyledon stage, the experimental pesticide solution was diluted with water to prepare a 500 ppm solution, and 5 ml of the solution was sprayed on the cucumbers. After air drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20℃, humidity 70%RH) and sprayed with a suspension of conidial spores of cucumber powdery mildew fungus (Erysiphe polygoni). After 9 days, the proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Experiment 1.

[0667] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0668] Compound No.: 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-0 22, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1-043, 1- 044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084, 1-085, 1-086 , 1-088, 1-089, 1-090, 1-091, 1-092, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-1 09, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-129, 1- 130, 1-131, 1-132, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-144, 1-145, 1-146, 1-147, 1-148, 1-149, 1-150, 1-151, 1-153, 1 -154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176,1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-224, 1-226, 1-230, 1-232, 1-233, 1-242, 1-249, 1-259, 1-261, 1-262, 1-264, 1-267, 1-268, 1-269, 1-270, 1-271, 1-273, 1-274, 1-275, 1-276 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-306, 1-307, 1-308, 1-309, 1-310, 1-313 1-315, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-327, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-341, 1-342, 1-343, 1-344, 1-345, 1-346, 1-347, 1-348, 1-349.

[0669] Experimental Example 6. Experiment on the control effect of cucumber anthracnose At 90cm 3Cucumbers (variety: Sagami Hanshiro) were planted in plastic containers. During the cotyledon stage, the experimental pesticide solution was diluted with water to prepare a 500 ppm solution, and 5 ml of the solution was sprayed on the cucumbers. One day after spraying, a suspension of conidial spores of *Colletotrichum lagenarium* was sprayed onto the cucumbers, and the inoculation chamber was placed in an inoculation chamber at 25°C and 100% RH for 2 days. Afterward, it was placed in an air-conditioned greenhouse (23°C and 60% RH) for 7 days. The proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Experiment 1.

[0670] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0671] Compound No.: 1-001, 1-003, 1-004, 1-005, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-0 21, 1-022, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-030, 1-031, 1-032, 1-033, 1-034, 1-035, 1-036, 1-037, 1-038, 1-039, 1-040, 1-041, 1-042, 1- 043, 1-044, 1-045, 1-046, 1-047, 1-048, 1-049, 1-050, 1-051, 1-052, 1-053, 1-054, 1-055, 1-056, 1-057, 1-058, 1-059, 1-060, 1-061, 1-062, 1-063, 1-064, 1-065, 1-066, 1-067, 1-068, 1-069, 1-070, 1-071, 1-072, 1-073, 1-074, 1-075, 1-076, 1-077, 1-078, 1-079, 1-080, 1-081, 1-082, 1-083, 1-084 , 1-085, 1-086, 1-087, 1-088, 1-089, 1-090, 1-091, 1-092, 1-093, 1-094, 1-095, 1-096, 1-097, 1-098, 1-099, 1-100, 1-101, 1-102, 1-103, 1-104, 1-1 05, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1- 126, 1-127, 1-128, 1-129, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-141, 1-142, 1-143, 1-144, 1-145, 1-146, 1 -147, 1-148, 1-149, 1-150, 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-158, 1-159, 1-160, 1-161, 1-162, 1-163, 1-164, 1-165, 1-166, 1-168, 1-169,1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-184, 1-186, 1-187, 1-188, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-204, 1-2 05, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-212, 1-213, 1-214, 1-215, 1-216, 1-218, 1-219, 1-220, 1-221, 1-259, 1-261, 1-262, 1-264, 1-265, 1-267, 1-268, 1-269, 1-270, 1-271, 1-272, 1-273, 1-274, 1-275, 1-276 1-277, 1-278, 1-279, 1-280, 1-281, 1-282, 1-283, 1-284, 1-285, 1-286, 1-287, 1-288, 1-289, 1-290, 1-291, 1-292, 1-293, 1-294, 1-295, 1-296, 1-298, 1-299, 1-301, 1-302, 1-303, 1-304, 1-305, 1-307, 1-308, 1-309, 1-3 10, 1-311, 1-312, 1-313, 1-315, 1-316, 1-317, 1-318, 1-319, 1-320, 1-321, 1-322, 1-323, 1-324, 1-325, 1-326, 1-328, 1-329, 1-330, 1-331, 1-332, 1-333, 1-334, 1-335, 1-336, 1-337, 1-338, 1-339, 1-340, 1-348, 1-349.

[0672] Experimental Example 7. Test on the control effect of soybean rust At 90cm 3Soybeans (variety: ENREI) were planted in plastic containers. At the single-leaf stage, the test pesticide solution was diluted with water to a 500ppm solution, and 5ml of each solution was sprayed onto the soybeans. One day after spraying, a suspension of conidial spores of soybean rust fungus (Phakopsorapachyrhizi) was sprayed onto the soybeans, and the inoculation chamber was placed in an inoculation chamber at 20℃ and 100%RH for 2 days. Afterwards, it was placed in an air-conditioned greenhouse (20℃, 60%RH) for 10 days. The proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Experiment 1.

[0673] As a result, among the compounds supplied for testing, the following compounds showed a control value of over 70%.

[0674] Compound No.: 1-003, 1-012, 1-015, 1-016, 1-022, 1-023, 1-025, 1-026, 1-027, 1-028, 1-032, 1-036, 1-038, 1-040, 1-041, 1-042, 1-043, 1-044, 1-045, 1-046, 1-048, 1-049, 1-050, 1- 051, 1-074, 1-080, 1-082, 1-083, 1-085, 1-087, 1-088, 1-114, 1-175, 1-176, 1-178, 1-180, 1-182, 1-183, 1-184, 1-186, 1-215, 1-268, 1-270, 1-272, 1-273, 1-284, 1-314, 1-340.

[0675] (Industry availability) The pyrazole compounds of the present invention exhibit excellent pest control activity, especially bactericidal activity, and have almost no adverse effects on non-target organisms such as mammals, fish and beneficial insects, making them extremely useful compounds.

Claims

1. A pyrazole compound or a salt thereof, as shown in formula (1), [Chemical Formula 1] In the formula, G represents G-1, G-1 represents the structure shown in the following structural formula. [Chemical Formula 2] G 1 represents a hydroxy group, a nitro group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6 alkyl)amino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a C3-C6 cycloalkylaminocarbonyl group or a di(C1-C6 alkyl)aminocarbonyl group, 10 represents a hydroxy group, a nitro group, a cyano group, a halogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a di(C1-C6 alkyl)amino group, a C1-C6 alkylcarbonyl group, a C1-C6 alkoxycarbonyl group, a C1-C6 alkylaminocarbonyl group, a C3-C6 cycloalkylaminocarbonyl group or a di(C1-C6 alkyl)aminocarbonyl group, 10 represents a hydroxy group, a nitro group, a cyano group, a halogen atom, a C1-C6 with respect to G 1 each G 1 are identical to or different from each other, R X represents C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, benzyl, R 10 represents C1-C6alkyl, C3-C6cycloalkyl, C1-C6haloalkyl, benzyl, R X -1, R X -2, R X -3 or R X -4, R X -1~R X -4 represents the structure shown in the following structural formulas. [Chemical Formula 3] X 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. About X 1 The relationships between them, when u5 represents integers 2, 3, 4 or 5, are as follows: 1 They are the same or different from each other. About X 1 The relationships between them, when u4 represents integers 2, 3, or 4, are as follows: 1 They are the same or different from each other. R Y Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. R 1 Indicates a hydrogen atom or a C1-C6 alkyl group. R 2 Indicates a hydrogen atom or a C1-C6 alkyl group. R 3 Indicates a hydrogen atom or a C1-C6 alkyl group. R 4 Represents hydrogen atom, halogen atom, C1-C6 alkyl or C1-C6 alkoxy group, R 5 Indicates hydrogen atom, halogen atom, or C1-C6 alkyl group. Z 1 Indicates E-1 to E-29 or E-30. Z 2 This indicates hydroxyl, carboxyl, amino, nitro, cyano, halogen atom, C1-C6 alkyl, C3-C6 alkyl, C6 ... 10 Cycloalkyl, C1-C6 haloalkyl, C3-C 10 Halogenated cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl or C1-C6 alkylsulfonyl Regarding Z 2 The relationships between them, when n4 represents an integer 2, 3 or 4, are as follows: 1 They are the same or different from each other. E-1 to E-30 each represent the structure shown in the following structural formulas. [Chemical Formula 4] Z a This indicates hydroxyl, mercapto, halogen, cyano, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkoxy, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Regarding Z a The relationships between them, when v2 represents the integer 2, are as follows: a They are the same or different from each other. Regarding Z a The relationships between them, when v4 represents integers 2, 3, or 4, are as follows: a They are the same or different from each other. Z b Indicates C1 to C6 alkyl groups. R a This indicates hydroxyl, cyano, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyloxy, C1-C6 alkylcarbonylamino, phenylcarbonylamino, -ОR g -C(О)R g -NR h SO2R j Or Q-1, Q-1 represents the structure shown in the following structural formula. [Chemical Formula 5] Q 1 This indicates a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxy group. Regarding Q 1 The relationships between them, when w5 represents integers 2, 3, 4, or 5, are as follows: 1 They are the same or different from each other. R b Indicates a hydrogen atom or a C1-C6 alkyl group. R c Indicates a hydrogen atom or a C1-C6 alkyl group. R d Indicates amino, hydroxyamino, C1-C6 alkylamino, C3-C6 alkylamino, C4-C6 alkylamino. 10 Cycloalkylamino, di(C1-C6)amino, pyrrolid-1-yl, morpholin-1-yl, or piperidin-1-yl R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy R f This represents a hydrogen atom, hydroxyl group, C1-C6 alkyl group, C1-C6 alkyl carbonyl group, C1-C6 alkoxy carbonyl group, C1-C6 alkylamino carbonyl group, di(C1-C6 alkyl)amino carbonyl group, C1-C6 alkyl sulfonyl group, or C1-C6 haloalkyl sulfonyl group. R g Indicates Q-1, R h Indicates a hydrogen atom or a C1-C6 alkyl group. R j Indicates C1 to C6 alkyl groups. m5 represents the integers 0, 1, 2, 3, 4, or 5. n4 represents the integer 0, 1, 2, 3, or 4. u5 represents the integers 0, 1, 2, 3, 4, or 5. u4 represents the integer 0, 1, 2, 3, or 4. p represents the integer 0 or 1. v4 represents the integer 0, 1, 2, 3, or 4. v2 represents the integer 0, 1, or 2. v1 represents the integer 0 or 1. w5 represents the integers 0, 1, 2, 3, 4, or 5.

2. The pyrazole compound or a salt thereof according to claim 1, wherein, G 1 Indicates a halogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group. R X Indicates C1-C6 alkyl, R X -1 or R X -2, R Y Represents a hydrogen atom. R 1 Represents a hydrogen atom. R 2 Represents a hydrogen atom. R 3 Represents a hydrogen atom. R 4 Represents a hydrogen atom. R 5 Represents a hydrogen atom. Z 1 represents E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-10, E-11, E-12, E-13, E-16, E-17, E-18, E-19, E-20, E-21, E-24, E-25, E-26, E-27, E-29 or E-30, Z 2 Indicates C1 to C6 alkoxy groups. Z a This indicates hydroxyl, mercapto, halogen atom, C1-C6 alkyl, and R-terminated groups. a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 alkylthio, -C(=NOR) b )R c -C(O)R d -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl Q 1 Represents halogen atoms, R b Indicates C1 to C6 alkyl groups. R c Indicates C1 to C6 alkyl groups. R e Represents hydrogen atoms, C1-C6 alkyl groups, C3-C6 alkyl groups. 10 Cycloalkyl or C1-C6 alkoxy R h Indicates C1 to C6 alkyl groups. m5 represents the integer 0 or 1. n4 represents the integer 0 or 1. u5 represents the integer 0. u4 represents the integer 0. p represents the integer 1. v4 represents the integer 0. w5 represents the integer 0 or 1.

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

4. The pyrazole compound or a salt thereof according to claim 3, wherein, Z a Indicates C1-C6 alkyl, via R a Substituted C1-C6 alkyl groups, C3-C 10 Cycloalkyl, C1-C6 haloalkyl, -C(=NOR) b )R c -NR e R f phenyl, pyrrolidone-1-yl, morpholino-1-yl, or piperidin-1-yl R a It represents C1-C6 alkoxy or C1-C6 alkylthio.

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

6. A pesticide containing one or more pyrazole compounds and their salts selected from any one of claims 1 to 5 as active ingredients.

7. A bactericide containing one or more pyrazole compounds and their salts selected from any one of claims 1 to 5 as active ingredients.

8. An agricultural and horticultural fungicide, comprising one or more pyrazole compounds and their salts selected from any one of claims 1 to 5 as active ingredients.

9. An antifungal agent comprising one or more pyrazole compounds and their salts selected from any one of claims 1 to 5 as active ingredients.

10. An endoparasite control agent, comprising one or more pyrazole compounds and their salts selected from any one of claims 1 to 5 as active ingredients.

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