Enamide compound and pest control agent

Abstract

The present invention provides: an enamide compound represented by formula (1) or a salt thereof; and a novel bactericide, particularly a novel bactericide for agricultural and horticultural use, which contains the compound or the salt thereof as an active ingredient.　In formula (1), R1 represents A-1-a; R2 represents G-2-a or the like; R5 represents J-1-a or the like; Q represents an oxygen atom or the like; R1aa represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or the like; R1ab represents a hydrogen atom; Z1a represents a C1 to C6 alkyl group; R2ac represents a hydrogen atom, a halogen atom, a C1 to C6 alkyl group, or the like; R2ad represents a hydrogen atom; R2ae represents a hydrogen atom; R2af represents a hydrogen atom; R5aa represents a phenyl group which is substituted by (Z5c)m, or the like; R5ab represents a hydrogen atom; Z5c represents a halogen atom or the like; and m represents a structure represented by an integer of 1, 2 or 3.

Description

Enamide compounds and pesticides

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

[0002] Certain enamide compounds are known to have fungicidal activity (see, for example, Patent Document 1). Patent Documents 2 to 14 disclose that certain pyrazole compounds are useful as fungicides, but they do not disclose anything about the enamide compounds of the present invention, and their usefulness as pest control agents is not known.

[0003] International Publication No. WO 2022 / 058877, International Publication No. WO 2022 / 253645, International Publication No. WO 2023 / 012044, International Publication No. WO 2023 / 110869, International Publication No. WO 2023 / 110871, International Publication No. WO 2024 / 068950, International Publication No. WO 2024 / 068947, International Publication No. WO 2024 / 100115, International Publication No. WO 2024 / 105104, International Publication No. WO 2024 / 115509, International Publication No. WO 2024 / 115512, International Publication No. WO 2024 / 115546, International Publication No. WO 2024 / 156886, International Publication No. WO 2024 / 160801

[0004] However, long-term use of pesticides can lead to the development of drug resistance in pathogens, and therefore, there is a constant demand for the development of new pesticides with excellent control effects.

[0005] As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel enamide compound according to the present invention, represented by the following formula (1), exhibits excellent control activity as a fungicide, particularly as an agricultural and horticultural fungicide, and have completed the present invention.

[0006] The enamide compounds of the present invention are not disclosed in any literature, and their usefulness as pest control agents is not known.

[0007] That is, the present invention relates to the following [1].

[0008] [1] Formula (1):

[0009] [In formula (1), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula:

[0010] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy, R １ａｂ is a hydrogen atom, C １ ~C ６ Alkyl, halogen atom, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) alkyl; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula:

[0011] Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, Z ２ In the relationship, when p3 represents an integer of 2 or 3, each Z２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom or a halogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents an alkyl group, and Q represents an oxygen atom, a sulfur atom, or NOR ７ represents R ７ is a hydrogen atom or C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20, J-21, phenylcarbonyl, -CH ２ R ５ａ , -C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ, C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amino, —C(O)R ５ｄ , phenyl, (Z ５ｃ ) ｍ phenyl substituted by -C(=NOR ２ａ ) R ２ｂ , —C(O)NR ５ｃ R ５ｆ , C １ ~C ７ Alkyl or halo(C １ ~C ６ ) alkyl; J-1-a, J-2 to J-13, J-15 to J-18, J-20, and J-21 each represent a structure represented by the following structural formula:

[0012] Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) Alkyl, E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-13, E-15, E-19, E-22, E-25, E-26, E-27, E-28, E- 29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ５ may be the same as or different from each other, and E-1 to E-9, E-13, E-15, E-19, E-22, E-25 to E-44, and E-45 each represent a structure represented by the following structural formula:

[0013] Z ６ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl; Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６ may be the same as or different from each other, Z ６In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl, —CH ２ OH, C ３ ~C １０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ represents R ５ａｂ represents a hydrogen atom; ５ａ is (Z ５ａ ) ｍ１ Phenyl substituted by -NHC(O)OR ５ｆ represents R ５ｂ is (Z ５ｂ ) ｍ１ phenyl, phenyl, substituted by —C(O)R ５ｆ , C １ ~C ６ Alkoxycarbonyl, E-1, phenylcarbonyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C ３ ~C １０) cycloalkyl, E-1, E-3, E-5, E-7, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-24, (Z ５ｂ ) ｍ１ phenyl, phenyl, C １ ~C ６ Alkoxy, —OH, halo(C １ ~C ６ ) alkyl or —C(═NH)R ５ｅ E-10 to E-12, E-14, E-16 to E-18, E-20, E-21, E-23 and E-24 represent structures represented by the following structural formulas, respectively:

[0014] Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ａ is C １ ~C ６ Alkyl, E-14, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｄ represents L-1 or L-2, and L-1 and L-2 represent structures represented by the following structural formulas:

[0015] R ５ｅ is (Z ５ｄ ) ｍ１ represents phenyl substituted by R ５ｆ is C１ ~C ６ Alkyl or halo(C １ ~C ６ ) alkyl, R １０ is Halo (C １ ~C ６ ) represents an alkyl or halogen atom; R １１ is cyano, phenyl, (Z ５ｄ ) ｍ1 phenyl substituted by １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylthio, -OCOCH ３ , L-3, Di(C １ ~C ６ alkyl)amino, L-2, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, -NHCOCH ３ or C １ ~C ６ L-3 represents a structure represented by the following structural formula:

[0016] Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C１ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃ may be the same as or different from each other, Z ５ｄ represents a halogen atom, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｄ may be the same or different, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, p4 represents an integer of 0, 1, 2, 3 or 4, and p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, or a salt thereof.

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

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

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

[0020] The compound of the present invention exists as geometric isomers having two types of configurations due to the enamine structure, namely, compounds represented by formula (1A) and compounds represented by formula (1B). The present invention encompasses a mixture containing the compound represented by formula (1A), the compound represented by formula (1B), or the compound represented by formula (1A) and the compound represented by formula (1B) in any ratio.

[0021] The compounds of the present invention may exist as geometric isomers of E- and Z-forms depending on the types of substituents, and the compounds of the present invention include mixtures containing these E-, Z-, or E- and Z-forms in any ratio.

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

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

[0024] Furthermore, among the compounds of the present invention, those that can be converted into salts by a conventional method include salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; salts of amino acids such as glutamic acid and aspartic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium, barium, and magnesium; aluminum salts; and quaternary ammonium salts such as tetramethylammonium salt, tetrabutylammonium salt, and benzyltrimethylammonium salt.

[0025] Furthermore, the compound of the present invention may exist as one or more rotational isomers due to restricted bond rotation caused by steric hindrance between substituents, and the compound of the present invention encompasses all rotational isomers or a mixture of diastereomers containing all rotational isomers in any ratio.

[0026] Next, specific examples of each substituent shown in this specification are shown below, where n- means normal, i- means iso, s- means secondary, tert- means tertiary, and Ph means phenyl.

[0027] As used herein, the term "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the term "halo" used herein also represents these halogen atoms.

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

[0029] As used herein, "halo(C ａ ~C ｂ The expression "alkyl" refers to a straight-chain or branched-chain hydrocarbon having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and in this case, when two or more halogen atoms are substituted, the halogen atoms may be the same or different. Specific examples include fluoromethyl, chloromethyl, bromomethyl, iodomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, trichloromethyl, bromodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, and 2,2,2-trichloroethyl, and each alkyl group may be selected within the range of the number of carbon atoms specified.

[0030] In this specification, "C ａ ~C ｂ The term "alkoxy" represents alkyl-O- as defined above having a to b carbon atoms, and specific examples thereof include methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butyloxy, i-butyloxy, s-butyloxy, tert-butyloxy, 2-ethylhexyloxy, and the like, and each alkoxy group is selected within the range of the number of carbon atoms specified.

[0031] In this specification, "C ａ ~C ｂThe term "alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon having a to b carbon atoms and one or more double bonds in the molecule, and specific examples thereof include vinyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 2-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, and 1,1-dimethyl-2-propenyl, and the like are selected within the range of the number of carbon atoms specified for each group.

[0032] In this specification, "C ａ ~C ｂ The term "alkynyl" refers to a linear or branched unsaturated hydrocarbon having a to b carbon atoms and one or more triple bonds in the molecule, and specific examples thereof include ethynyl, propargyl, 2-butynyl, 3-butynyl, 1-pentynyl, 1-hexynyl, and 4,4,4-trifluoro-2-butynyl, and are selected within the range of the number of carbon atoms specified for each group.

[0033] In this specification, "C ａ ~C ｂ The term "cycloalkyl" refers to a cyclic hydrocarbon having a to b carbon atoms, and can form a single ring or multiple ring structures ranging from 3 to 10 members. Each ring may be optionally substituted with alkyl within the specified range of carbon atoms. Specific examples include cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl, each selected within the specified range of carbon atoms.

[0034] As used herein, "halo(C ａ ~C ｂThe term "cycloalkyl" refers to a cyclic hydrocarbon having a to b carbon atoms in which hydrogen atoms bonded to the carbon atoms are optionally substituted with halogen atoms, and can form a 3- to 10-membered single or multiple ring structure. Each ring may also be optionally substituted with alkyl within the specified range of carbon atoms. Specific examples include 1-chlorocyclopropyl, 1-methyl-2-chlorocyclopropyl, 2-methyl-2-fluorocyclopropyl, 1-fluoro-2,2-dimethylcyclopropyl, 1-chlorocyclobutyl, 1-fluorocyclopentyl, and 1-chlorocyclohexyl, each of which is selected within the specified range of carbon atoms.

[0035] In this specification, "C ａ ~C ｂ The expression "alkylthio" represents alkyl-S- as defined above having a to b carbon atoms, and specific examples thereof include methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, and tert-butylthio, and each is selected within the range of the specified number of carbon atoms.

[0036] In this specification, "C ａ ~C ｂ The expression "alkylsulfonyl" means alkyl-S(O) having the above meaning and containing a to b carbon atoms. ２ Specific examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, n-butylsulfonyl, i-butylsulfonyl, s-butylsulfonyl, tert-butylsulfonyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0037] In this specification, "C ａ ~C ｂThe term "alkoxycarbonyl" represents alkyl-O-C(O)- having a to b carbon atoms as defined above, and specific examples thereof include methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, i-propyloxycarbonyl, n-butoxycarbonyl, i-butoxycarbonyl, s-butoxycarbonyl, tert-butoxycarbonyl, and 2-ethylhexyloxycarbonyl, and each of these is selected within the range of the number of carbon atoms specified.

[0038] As used herein, "halo(C ａ ~C ｂ The notation "halo(C)alkoxy" represents haloalkyl-O- having the above-mentioned meaning and containing a to b carbon atoms. ａ ~C ｂ Specific examples of "C alkoxy" include difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, and 1,1,2,3,3,3-hexafluoropropyloxy. ａ ~C ｂ The "haloalkoxy" is selected from the range of carbon atoms specified.

[0039] In this specification, "C ａ ~C ｂ The expression "alkylcarbonyl" represents alkyl-C(O)- as defined above, having a to b carbon atoms. ａ ~C ｂ Specific examples of "alkylcarbonyl" include acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, 2-methylbutanoyl, pivaloyl, hexanoyl, and heptanoyl. ａ ~C ｂ The "alkylcarbonyl" is selected from the specified range of carbon atoms.

[0040] In this specification, "di(C ａ ~C ｂThe expression "alkyl(amino)" represents an amino group in which both hydrogen atoms are substituted with alkyl as defined above, which may be the same or different and have a to b carbon atoms, and specific examples include dimethylamino, ethyl(methyl)amino, diethylamino, n-propyl(methyl)amino, i-propyl(methyl)amino, di(n-propyl)amino, di(n-butyl)amino, etc., selected within the range of the number of carbon atoms specified for each group.

[0041] In this specification, "C ａ ~C ｂ The expression "alkoxymethyl" means an alkyl-O-CH group having the above-mentioned meaning and containing a to b carbon atoms. ２ Specific examples include methoxymethyl, ethoxymethyl, n-propyloxymethyl, i-propyloxymethyl, n-butoxymethyl, i-butoxymethyl, s-butoxymethyl, tert-butoxymethyl, 2-ethylhexyloxymethyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0042] In this specification, "C ａ ~C ｂ The expression "alkoxyethyl" means an alkyl-O-C group having the above-mentioned meaning and containing a to b carbon atoms. ２ H ４ Specific examples include methoxyethyl, ethoxyethyl, n-propyloxyethyl, i-propyloxyethyl, n-butoxyethyl, i-butoxyethyl, s-butoxyethyl, tert-butoxyethyl, 2-ethylhexyloxyethyl, and the like, and each is selected within the range of the number of carbon atoms specified.

[0043] In this specification, "C ａ ~C ｂ The notation of "cycloalkylmethyl" means a cycloalkyl-CH having the above-mentioned meaning and containing a to b carbon atoms. ２ - group, and specific examples include cyclopropylmethyl, cyclohexylmethyl, etc., each of which is selected within the range of the number of carbon atoms specified.

[0044] In this specification, "C ａ ~Cｂ The notation of "cycloalkylethyl" means the above-mentioned cycloalkyl-C having a to b carbon atoms. ２ H ４ - group, and specific examples include cyclopropylethyl, cyclohexylethyl, etc., each of which is selected within the range of the number of carbon atoms specified.

[0045] The term "phenylcarbonyl" used herein means -C(O)-C ６ H ５ Represents.

[0046] The term "benzyl" used herein means -CH ２ C ６ H ５ Represents.

[0047] In this specification, "R １０ C replaced by ａ ~C ｂ The notation "alkenyl" refers to any R １０ represents an alkenyl group having the above-mentioned meaning and having a to b carbon atoms, in which a hydrogen atom bonded to the carbon atom is optionally substituted, and the number of carbon atoms is selected within the range specified for each. ａ ~C ｂ Substituent R on the alkenyl group １０ When there are two or more R １０ may be the same as each other or different from each other.

[0048] In this specification, "(Z ５ｃ ) ｍ The notation "phenyl substituted by" refers to any Z ５ｃ represents a phenyl group in which m hydrogen atoms bonded to the carbon atom are substituted. ５ｃ ) ｍ In addition, the substituent Z on each phenyl group can be any integer depending on the ５ｃ When there are two or more Z ５ｃ may be the same as each other or different from each other.

[0049] In this specification, "R １１ C replaced byａ ~C ｂ The notation "alkyl" refers to any R １１ represents an alkyl group having the above-mentioned meaning and having a to b carbon atoms, in which a hydrogen atom bonded to the carbon atom is optionally substituted, and the number of carbon atoms is selected within the range of the specified number of carbon atoms. ａ ~C ｂ Substituent R on the alkyl group １１ When there are two or more R １１ may be the same as each other or different from each other.

[0050] In this specification, "(Z ５ｃ ) ｍ The notation "phenyl substituted by" refers to any Z ５ｃ represents a phenyl group in which m hydrogen atoms bonded to the carbon atom are substituted. ５ｃ ) ｍ In addition, the substituent Z on each phenyl group can be any integer depending on the ５ｃ When there are two or more Z ５ｃ may be the same as each other or different from each other.

[0051] In this specification, "(Z ５ａ ) ｍ１ "phenyl substituted by" (Z ５ｂ ) ｍ１ "phenyl substituted by" (Z ５ｄ ) ｍ１ The notation "phenyl substituted by" refers to any Z ５ａ , Z ５ｂ or Z ５ｄ represents a phenyl group in which m1 hydrogen atoms bonded to the carbon atom are substituted. ５ａ ) ｍ１ , (Z ５ｂ ) ｍ１ or (Z ５ｄ ) ｍ１ In addition, the substituent Z on each phenyl group can be any integer depending on the ５ａ , Z ５ｂ or Z ５ｄ When there are two or more Z ５ａ , Z５ｂ or Z ５ｄ may be the same as each other or different from each other.

[0052] Next, a method for producing the compound of the present invention represented by formula (1) will be described. The compound of the present invention represented by formula (1) can be produced, for example, by the following method. Note that the following explanation is merely illustrative, and the compound of the present invention represented by formula (1) may also be produced by other methods.

[0053] Hereinafter, "the compound of the present invention represented by formula (1)" will also be referred to as "compound (1)," and "the compound represented by formula (2)" will also be referred to as "compound (2)." Other compounds will also be similarly described.

[0054] Preparation Example 1 Among the compounds (1) of the present invention, a compound (1-1) in which Q is an oxygen atom can be prepared, for example, by reacting a compound (2) with a compound (3).

[0055] [In the formula, R １ , R ２ and R ５ has the same meaning as above.] Compound (1-1) can be produced by reacting compound (2) with compound (3) in a solvent or without a solvent, and optionally in the presence of a base, a condensing agent, and an additive.

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

[0057] Some of the compounds (3) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds as described in the literature.

[0058] When a solvent is used, any solvent may be used as long as it is inert to the reaction, and examples thereof include water, alcohol solvents such as methanol, ethanol, etc.; ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, etc.; aromatic hydrocarbon solvents such as benzene, xylene, toluene, etc.; aliphatic hydrocarbon solvents such as pentane, hexane, cyclohexane, etc.; halogenated hydrocarbon solvents such as dichloromethane, chloroform, 1,2-dichloroethane, etc.; nitrile solvents such as acetonitrile, propionitrile, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N'-dimethylimidazolidinone, etc.; dimethyl sulfoxide, and mixed solvents thereof.

[0059] The reaction can be carried out in the presence of a base. Examples of bases that can be used include organic bases such as pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), and 1,5-diazabicyclo[4.3.0]-5-nonene (DBN); inorganic bases such as sodium hydroxide, potassium hydroxide, sodium hydride, sodium bicarbonate, potassium carbonate, cesium carbonate, and potassium phosphate; and metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide. The amount (equivalent) of the base used is 0.1 to 100 equivalents per equivalent of compound (2).

[0060] The reaction can be carried out in the presence of a condensing agent. Usable condensing agents include 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N'-dicyclohexylcarbodiimide, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 2-chloro-1-methylpyridinium iodide, and propylphosphonic anhydride. The amount (equivalent) of the condensing agent used is 0.1 to 100 equivalents per equivalent of compound (2).

[0061] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol and 1-hydroxybenzotriazole. The amount (equivalent) of the additive used can be 0.005 to 20 equivalents per equivalent of compound (2).

[0062] The reaction temperature can be set at any temperature between −78° C. and the reflux temperature of the reaction mixture, and the reaction time varies depending on the concentration of the reactant and the reaction temperature, but can usually be set at any time within the range of 5 minutes to 100 hours.

[0063] Preparation Example 2 Compound (1-1) can be prepared, for example, by reacting compound (2) with compound (4).

[0064] [wherein X represents a leaving group such as a chlorine atom, a bromine atom, or an iodine atom; R １ , R ２ and R ５ has the same meaning as above.] Compound (1-1) can be produced by reacting compound (2) with compound (4) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0065] The amount of compound (4) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (2).

[0066] Some of the compounds (4) are known compounds, some of which are commercially available, and others can be prepared according to general methods for synthesizing known compounds as described in the literature.

[0067] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0068] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0069] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

[0070] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0071] (Production Example 3) In the compound (1-1), R ５ -C(O)NHNHR ５ｂ The compound (1-1-1) represented by the formula: can be produced, for example, by reacting the compound (2) with oxalyl chloride and the compound (5).

[0072] [In the formula, R １ , R ２ and R ５ｂ has the same meaning as above.] Compound (1-1-1) can be produced by reacting compound (2) with oxalyl chloride and compound (5) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0073] The amount of oxalyl chloride used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2). The amount of compound (5) used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).

[0074] Some of the compounds (5) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

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

[0076] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0077] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

[0078] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0079] (Production Example 4) In the compound (1-1), R ５ -C(O)NHR ５ｃ The compound (1-1-2) represented by the formula: can be produced, for example, by reacting the compound (2) with oxalyl chloride and the compound (6).

[0080] [In the formula, R １ , R ２ and R ５ｃ has the same meaning as above.] Compound (1-1-2) can be produced by reacting compound (2) with oxalyl chloride and compound (6) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0081] The amount of oxalyl chloride used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2). The amount of compound (6) used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).

[0082] Some of the compounds (6) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0083] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0084] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0085] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

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

[0087] Preparation Example 5 The compound (1-1) can be prepared by reacting the compound (1-1-3) with the compound (7-1) or the compound (7-2).

[0088] [In the formula, R １０２ is a hydrogen atom or C １ ~C ４ represents alkyl, and X and R １ , R ２ and R ５ has the same meaning as defined above.] Compound (1-1) can be produced by reacting compound (1-1-3) with compound (7-1) or compound (7-2) in a solvent or without a solvent, and optionally in the presence of a palladium catalyst and a base.

[0089] The amount of compound (7-1) and compound (7-2) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-1-3).

[0090] Some of the compounds (7-1) and (7-2) are known compounds, and some are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0091] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0092] The reaction can be carried out in the presence of a palladium catalyst. Examples of usable palladium catalysts include palladium acetate, tetrakis(triphenylphosphine)palladium (zerovalent), tris(dibenzylideneacetone)dipalladium (zerovalent), bis(triphenylphosphine)palladium (divalent) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium (divalent) dichloride, and the like. The amount (equivalent) of the palladium catalyst used is 0.005 to 20 equivalents per equivalent of compound (1-1-3).

[0093] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1-3).

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

[0095] Preparation Example 6 The compound (1-1) can be prepared, for example, by reacting the compound (1-1-4) with the compound (8-1).

[0096] [wherein, X, R １ , R ２ and R ５has the same meaning as defined above.] Compound (1-1) can be produced by reacting compound (1-1-4) with compound (8-1) in a solvent or without a solvent, and optionally in the presence of a palladium catalyst and a base.

[0097] The amount of compound (8-1) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-1-4).

[0098] Some of the compounds (8-1) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0099] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0100] The reaction can be carried out in the presence of a palladium catalyst. Examples of usable palladium catalysts include palladium acetate, tetrakis(triphenylphosphine)palladium (zerovalent), tris(dibenzylideneacetone)dipalladium (zerovalent), bis(triphenylphosphine)palladium (divalent) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium (divalent) dichloride, and the like. The amount (equivalent) of the palladium catalyst used is 0.005 to 20 equivalents per equivalent of compound (1-1-4).

[0101] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1-4).

[0102] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0103] Production Example 7 The compound (1-1) can be produced by reacting the compound (1-1-5) with the compound (7-3) or the compound (7-4).

[0104] [In the formula, R １０２ , X, R １ , R ２ and R ５ has the same meaning as defined above.] Compound (1-1) can be produced by reacting compound (1-1-5) with compound (7-3) or compound (7-4) in a solvent or without a solvent, and optionally in the presence of a palladium catalyst and a base.

[0105] The amount of compound (7-3) and compound (7-4) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-1-5).

[0106] Some of the compounds (7-3) and (7-4) are known compounds, and some are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0107] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0108] The reaction can be carried out in the presence of a palladium catalyst. Examples of usable palladium catalysts include palladium acetate, tetrakis(triphenylphosphine)palladium (zerovalent), tris(dibenzylideneacetone)dipalladium (zerovalent), bis(triphenylphosphine)palladium (divalent) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium (divalent) dichloride, and the like. The amount (equivalent) of the palladium catalyst used is 0.005 to 20 equivalents per equivalent of compound (1-5).

[0109] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1-5).

[0110] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0111] Preparation Example 8 Compound (1-1) can be prepared, for example, by reacting compound (1-1-6) with compound (8-2).

[0112] [wherein, X, R １ , R ２ and R ５ has the same meaning as defined above.] Compound (1-1) can be produced by reacting compound (1-1-6) with compound (8-2) in a solvent or without a solvent, and optionally in the presence of a palladium catalyst and a base.

[0113] The amount of compound (8-2) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-1-6).

[0114] Some of the compounds (8-2) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0115] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0116] The reaction can be carried out in the presence of a palladium catalyst. Examples of usable palladium catalysts include palladium acetate, tetrakis(triphenylphosphine)palladium (zerovalent), tris(dibenzylideneacetone)dipalladium (zerovalent), bis(triphenylphosphine)palladium (divalent) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium (divalent) dichloride dichloromethane adduct, [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium (divalent) dichloride, and the like. The amount (equivalent) of the palladium catalyst used is 0.005 to 20 equivalents per equivalent of compound (1-6).

[0117] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1-6).

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

[0119] (Production Example 9) In the compound (1-1), R ５ -C(O)OR ５ｂ Compound (1-1-7) represented by the formula: can be produced, for example, by reacting compound (2) with oxalyl chloride and compound (10).

[0120] [In the formula, R １ , R ２ and R ５ｂ has the same meaning as above.] Compound (1-1-7) can be produced by reacting compound (2) with oxalyl chloride and compound (10) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0121] The amount of oxalyl chloride used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).The amount of compound (10) used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).

[0122] Some of the compounds (10) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0123] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0124] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0125] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

[0126] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0127] (Production Example 10) In the compound (1-1), R ５ -C(O)SR ５ｂ The compound (1-1-8) represented by the formula: can be produced, for example, by reacting the compound (2) with oxalyl chloride and the compound (11).

[0128] [In the formula, R １ , R ２ and R ５ｂ has the same meaning as above.] Compound (1-1-8) can be produced by reacting compound (2) with oxalyl chloride and compound (11) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0129] The amount of oxalyl chloride used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).The amount of compound (11) used may be in the range of 0.5 to 50 equivalents relative to 1 equivalent of compound (2).

[0130] Some of the compounds (11) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0131] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

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

[0133] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

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

[0135] Preparation Example 11 Compound (1-1) can be prepared, for example, by reacting compound (2) with compound (12).

[0136] [In the formula, R １０３ is C １ ~C ６ represents alkyl or benzyl, R １ , R ２ and R ５has the same meaning as above.] Compound (1-1) can be produced by reacting compound (2) with compound (12) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0137] The amount of compound (12) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (2).

[0138] Some of the compounds (12) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0139] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0140] The reaction can be carried out in the presence of a base. Examples of bases that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (2).

[0141] The reaction can be carried out in the presence of an additive. Examples of the additive that can be used include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (2).

[0142] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0143] Preparation Example 12 Compound (1-1) can be prepared, for example, by reacting compound (1-9) with thionyl chloride.

[0144] [In the formula, R １ , R ２ and R ５has the same meaning as above.] Compound (1-1) can be produced by reacting compound (1-9) with thionyl chloride in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0145] The amount of thionyl chloride used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-9).

[0146] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0147] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-9).

[0148] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0149] Preparation Example 13 Of the compounds (1) of the present invention, compound (1-2) in which Q is a sulfur atom can be prepared, for example, by reacting compound (1-1) with Lawesson's reagent.

[0150] [In the formula, R １ , R ２ and R ５ has the same meaning as above.] Compound (1-2) can be produced by reacting compound (1-1) with Lawesson's reagent in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0151] The amount of the Lawesson's reagent used may be in the range of 0.5 to 50 equivalents per equivalent of the compound (1-1).

[0152] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0153] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1).

[0154] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0155] (Production Example 14) Compound (1) of the present invention, wherein Q is NOR ７ The compound (1-3) represented by the formula: can be produced, for example, by reacting the compound (1-2) with the compound (14-1) or the compound (14-2).

[0156] [In the formula, R １ , R ２ , R ５ and R ７ has the same meaning as above.] Compound (1-3) can be produced by reacting compound (1-2) with compound (14-1) or compound (14-2) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0157] The amount of compound (14-1) or compound (14-2) used may be in the range of 0.5 to 50 equivalents per equivalent of compound (1-2).

[0158] Some of the compounds (14-1) and (14-2) are known compounds, and some are commercially available. Others can be prepared according to general synthetic methods for known compounds described in the literature.

[0159] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0160] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-2).

[0161] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0162] Examples of compounds (3) and (12) that can be used in these methods include the compounds shown in Table 1. However, Table 1 is for illustrative purposes only, and compounds (3) and (12) are not limited to these.

[0163] In the tables, Me represents methyl, and Bn represents benzyl.

[0164] In the table, the notations T-01 to T-237 represent the following structures.

[0165] In addition, the "*" in the structural formulae T-01 to T-273 above indicates the bonding site.

[0166] R in the table ５ The column indicates that the above T-01 to T-273 are R of the compound represented by formula (X). ５ are bonded to each other.

[0167] [Table 1] ―――――――― ―――――――― ―――――――― R 5 R 104 R 5 R 104 R 5 R 104――――――― ――――――― ――――――― T-01 Me T-01 Bn T-01 H T-02 Me T-02 Bn T-02 H T-03 Me T-03 Bn T-03 H T-04 Me T-04 Bn T-04 H T-05 Me T-05 Bn T-05 H T-06 Me T-06 Bn T-06 H T-07 Me T-07 Bn T-07 H T-08 Me T-08 Bn T-08 H T-09 Me T-09 Bn T-09 H T-10 Me T-10 Bn T-10 H T-11 Me T-11 Bn T-11 H T-12 Me T-12 Bn T-12 H T-13 Me T-13 Bn T-13 H T-14 Me T-14 Bn T-14 H T-15 Me T-15 Bn T-15 H T-16 Me T-16 Bn T-16 H T-17 Me T-17 Bn T-17 H T-18 Me T-18 Bn T-18 H T-19 Me T-19 Bn T-19 H T-20 Me T-20 Bn T-20 H T-21 Me T-21 Bn T-21 H T-22 Me T-22 Bn T-22 H T-23 Me T-23 Bn T-23 H T-24 Me T-24 Bn T-24 H T-25 Me T-25 Bn T-25 H T-26Me T-26 Bn T-26 H T-27 Me T-27 Bn T-27 H T-28 Me T-28 Bn T-28 H T-29 Me T-29 Bn T-29 H T-30 Me T-30 Bn T-30 H T-31 Me T-31 Bn T-31 H T-32 Me T-32 Bn T-32 H T-33 Me T-33 Bn T-33 H T-34 Me T-34 Bn T-34 H T-35 Me T-35 Bn T-35 H T-36 Me T-36 Bn T-36 H T-37 Me T-37 Bn T-37 H T-38 Me T-38 Bn T-38 H T-39 Me T-39 Bn T-39 H T-40 Me T-40 Bn T-40 H T-41 Me T-41 Bn T-41 H T-42 Me T-42 Bn T-42 H T-43 Me T-43 Bn T-43 H T-44 Me T-44 Bn T-44 H T-45 Me T-45 Bn T-45 H T-46 Me T-46 Bn T-46 H T-47 Me T-47 Bn T-47 H T-48 Me T-48 Bn T-48 H T-49 Me T-49 Bn T-49 H T-50 Me T-50 Bn T-50 H T-51 Me T-51 Bn T-51 H T-52Me T-52 Bn T-52 H T-53 Me T-53 Bn T-53 H T-54 Me T-54 Bn T-54 H T-55 Me T-55 Bn T-55 H T-56 Me T-56 Bn T-56 H T-57 Me T-57 Bn T-57 H T-58 Me T-58 Bn T-58 H T-59 Me T-59 Bn T-59 H T-60 Me T-60 Bn T-60 H T-61 Me T-61 Bn T-61 H T-62 Me T-62 Bn T-62 H T-63 Me T-63 Bn T-63 H T-64 Me T-64 Bn T-64 H T-65 Me T-65 Bn T-65 H T-66 Me T-66 Bn T-66 H T-67 Me T-67 Bn T-67 H T-68 Me T-68 Bn T-68 H T-69 Me T-69 Bn T-69 H T-70 Me T-70 Bn T-70 H T-71 Me T-71 Bn T-71 H T-72 Me T-72 Bn T-72 H T-73 Me T-73 Bn T-73 H T-74 Me T-74 Bn T-74 H T-75 Me T-75 Bn T-75 H T-76 Me T-76 Bn T-76 H T-77 Me T-77 Bn T-77 H T-78Me T-78 Bn T-78 H T-79 Me T-79 Bn T-79 H T-80 Me T-80 Bn T-80 H T-81 Me T-81 Bn T-81 H T-82 Me T-82 Bn T-82 H T-83 Me T-83 Bn T-83 H T-84 Me T-84 Bn T-84 H T-85 Me T-85 Bn T-85 H T-86 Me T-86 Bn T-86 H T-87 Me T-87 Bn T-87 H T-88 Me T-88 Bn T-88 H T-89 Me T-89 Bn T-89 H T-90 Me T-90 Bn T-90 H T-91 Me T-91 Bn T-91 H T-92 Me T-92 Bn T-92 H T-93 Me T-93 Bn T-93 H T-94 Me T-94 Bn T-94 H T-95 Me T-95 Bn T-95 H T-96 Me T-96 Bn T-96 H T-97 Me T-97 Bn T-97 H T-98 Me T-98 Bn T-98 H T-99 Me T-99 Bn T-99 H T-100 Me T-100 Bn T-100 H T-101 Me T-101 Bn T-101 H T-102 Me T-102 Bn T-102 H T-103 Me T-103 Bn T-103 HT-104 Me T-104 Bn T-104 H T-105 Me T-105 Bn T-105 H T-106 Me T-106 Bn T-106 H T-107 Me T-107 Bn T-107 H T-108 Me T-108 Bn T-108 H T-109 Me T-109 Bn T-109 H T-110 Me T-110 Bn T-110 H T-111 Me T-111 Bn T-111 H T-112 Me T-112 Bn T-112 H T-113 Me T-113 Bn T-113 H T-114 Me T-114 Bn T-114 H T-115 Me T-115 Bn T-115 H T-116 Me T-116 Bn T-116 H T-117 Me T-117 Bn T-117 H T-118 Me T-118 Bn T-118 H T-119 Me T-119 Bn T-119 H T-120 Me T-120 Bn T-120 H T-121 Me T-121 Bn T-121 H T-122 Me T-122 Bn T-122 H T-123 Me T-123 Bn T-123 H T-124 Me T-124 Bn T-124 H T-125 Me T-125 Bn T-125 H T-126 Me T-126 Bn T-126 H T-127 Me T-127 Bn T-127 H T-128 Me T-128 Bn T-128 H T-129 Me T-129 Bn T-129 HT-130 Me T-130 Bn T-130 H T-131 Me T-131 Bn T-131 H T-132 Me T-132 Bn T-132 H T-133 Me T-133 Bn T-133 H T-134 Me T-134 Bn T-134 H T-135 Me T-135 Bn T-135 H T-136 Me T-136 Bn T-136 H T-137 Me T-137 Bn T-137 H T-138 Me T-138 Bn T-138 H T-139 Me T-139 Bn T-139 H T-140 Me T-140 Bn T-140 H T-141 Me T-141 Bn T-141 H T-142 Me T-142 Bn T-142 H T-143 Me T-143 Bn T-143 H T-144 Me T-144 Bn T-144 H T-145 Me T-145 Bn T-145 H T-146 Me T-146 Bn T-146 H T-147 Me T-147 Bn T-147 H T-148 Me T-148 Bn T-148 H T-149 Me T-149 Bn T-149 H T-150 Me T-150 Bn T-150 H T-151 Me T-151 Bn T-151 H T-152 Me T-152 Bn T-152 H T-153 Me T-153 Bn T-153 H T-154 Me T-154 Bn T-154 H T-155 Me T-155 Bn T-155 HT-156 Me T-156 Bn T-156 H T-157 Me T-157 Bn T-157 H T-158 Me T-158 Bn T-158 H T-159 Me T-159 Bn T-159 H T-160 Me T-160 Bn T-160 H T-161 Me T-161 Bn T-161 H T-162 Me T-162 Bn T-162 H T-163 Me T-163 Bn T-163 H T-164 Me T-164 Bn T-164 H T-165 Me T-165 Bn T-165 H T-166 Me T-166 Bn T-166 H T-167 Me T-167 Bn T-167 H T-168 Me T-168 Bn T-168 H T-169 Me T-169 Bn T-169 H T-170 Me T-170 Bn T-170 H T-171 Me T-171 Bn T-171 H T-172 Me T-172 Bn T-172 H T-173 Me T-173 Bn T-173 H T-174 Me T-174 Bn T-174 H T-175 Me T-175 Bn T-175 H T-176 Me T-176 Bn T-176 H T-177 Me T-177 Bn T-177 H T-178 Me T-178 Bn T-178 H T-179 Me T-179 Bn T-179 H T-180 Me T-180 Bn T-180 H T-181 Me T-181 Bn T-181 HT-182 Me T-182 Bn T-182 H T-183 Me T-183 Bn T-183 H T-184 Me T-184 Bn T-184 H T-185 Me T-185 Bn T-185 H T-186 Me T-186 Bn T-186 H T-187 Me T-187 Bn T-187 H T-188 Me T-188 Bn T-188 H T-189 Me T-189 Bn T-189 H T-190 Me T-190 Bn T-190 H T-191 Me T-191 Bn T-191 H T-192 Me T-192 Bn T-192 H T-193 Me T-193 Bn T-193 H T-194 Me T-194 Bn T-194 H T-195 Me T-195 Bn T-195 H T-196 Me T-196 Bn T-196 H T-197 Me T-197 Bn T-197 H T-198 Me T-198 Bn T-198 H T-199 Me T-199 Bn T-199 H T-200 Me T-200 Bn T-200 H T-201 Me T-201 Bn T-201 H T-202 Me T-202 Bn T-202 H T-203 Me T-203 Bn T-203 H T-204 Me T-204 Bn T-204 H T-205 Me T-205 Bn T-205 H T-206 Me T-206 Bn T-206 H T-207 Me T-207 Bn T-207 HT-208 Me T-208 Bn T-208 H T-209 Me T-209 Bn T-209 H T-210 Me T-210 Bn T-210 H T-211 Me T-211 Bn T-211 H T-212 Me T-212 Bn T-212 H T-213 Me T-213 Bn T-213 H T-214 Me T-214 Bn T-214 H T-215 Me T-215 Bn T-215 H T-216 Me T-216 Bn T-216 H T-217 Me T-217 Bn T-217 H T-218 Me T-218 Bn T-218 H T-219 Me T-219 Bn T-219 H T-220 Me T-220 Bn T-220 H T-221 Me T-221 Bn T-221 H T-222 Me T-222 Bn T-222 H T-223 Me T-223 Bn T-223 H T-224 Me T-224 Bn T-224 H T-225 Me T-225 Bn T-225 H T-226 Me T-226 Bn T-226 H T-227 Me T-227 Bn T-227 H T-228 Me T-228 Bn T-228 H T-229 Me T-229 Bn T-229 H T-230 Me T-230 Bn T-230 H T-231 Me T-231 Bn T-231 H T-232 Me T-232 Bn T-232 H T-233 Me T-233 Bn T-233 HT-234 Me T-234 Bn T-234 H T-235 Me T-235 Bn T-235 H T-236 Me T-236 Bn T-236 H T-237 Me T-237 Bn T-237 H T-238 Me T-238 Bn T-238 H T-239 Me T-239 Bn T-239 H T-240 Me T-240 Bn T-240 H T-241 Me T-241 Bn T-241 H T-242 Me T-242 Bn T-242 H T-243 Me T-243 Bn T-243 H T-244 Me T-244 Bn T-244 H T-245 Me T-245 Bn T-245 H T-246 Me T-246 Bn T-246 H T-247 Me T-247 Bn T-247 H T-248 Me T-248 Bn T-248 H T-249 Me T-249 Bn T-249 H T-250 Me T-250 Bn T-250 H T-251 Me T-251 Bn T-251 H T-252 Me T-252 Bn T-252 H T-253 Me T-253 Bn T-253 H T-254 Me T-254 Bn T-254 H T-255 Me T-255 Bn T-255 H T-256 Me T-256 Bn T-256 H T-257 Me T-257 Bn T-257 H T-258 Me T-258 Bn T-258 H T-259 Me T-259 Bn T-259 HT-260 Me T-260 Bn T-260 H T-261 Me T-261 Bn T-261 H T-262 Me T-262 Bn T-262 H T-263 Me T-263 Bn T-263 H T-264 Me T-264 Bn T-264 H T-265 Me T-265 Bn T-265 H T-266 Me T-266 Bn T-266 H T-267 Me T-267 Bn T-267 H T-268 Me T-268 Bn T-268 H T-269 Me T-269 Bn T-269 H T-270 Me T-270 Bn T-270 H T-271 Me T-271 Bn T-271 H T-272 Me T-272 Bn T-272 H T-273 Me T-273 Bn T-273 H ---------------------------------------------------------------- Compound (2) used in Production Example 1 can be produced, for example, according to the production route (reaction pathway) shown in the following Reaction Scheme 1.

[0168] [Reaction Scheme 1]

[0169] [In the formula, R １ , R ２ has the same meaning as above.] Step 1: Compound (1-b) can be produced by reacting compound (1-c) with a reducing agent in accordance with a known method known in the literature, for example, the method described in WO 2012 / 102297.

[0170] Some of the compounds (1-c) are known compounds, and some are commercially available. Others can be produced by known methods, such as those described in Medicinal Chemistry Letters, Vol. 5, No. 7, pp. 748-753, 2014. Examples of compounds (1-c) that can be used in these methods include the compounds shown below. However, the following are merely examples, and compound (1-c) is not limited to these.

[0171] Step 2: Compound (1-a) can be produced by reacting compound (1-b) with a cyanating agent in accordance with a known method known in the literature, for example, the method described in Tetrahedron, 2019, Vol. 75, No. 2, pp. 308-315, etc.

[0172] Examples of the cyanating agent that can be used include trimethylsilyl cyanide, etc. The amount (equivalent) of the cyanating agent used can be 0.5 to 100 equivalents per equivalent of compound (1-b).

[0173] Some of the compounds (1-b) are known compounds, and some are commercially available. Others can be produced by known methods, such as those described in International Publication No. WO 2012 / 102297. Compounds (1-b) that can be used in these methods include, for example, the compounds shown below. However, the following are merely examples, and compound (1-b) is not limited to these.

[0174] Step 3: Compound (2) can be produced by reacting compound (1-a) with a reducing agent according to a known method known in the literature, for example, the method described in Organic Letters, 2016, Vol. 18, pp. 6388-6391.

[0175] Some of the compounds (1-a) are known compounds, and some are commercially available. Others can be produced according to known methods known in the literature, for example, methods described in International Publication No. 2022 / 253645. Compounds (1-a) that can be used in these methods include, for example, the compounds shown below. However, the following are merely examples, and compound (1-a) is not limited to these.

[0176] Examples of compound (2) used in Production Example 1 include the compounds shown below. However, the following are merely examples, and compound (2) is not limited to these.

[0177] The compound (1-1-3) used in Production Example 5 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 2.

[0178] [Reaction Scheme 2]

[0179] [wherein, X, R １ , R ２ and R ５ has the same meaning as defined above.] Step 1: Compound (1-1-3-2) can be produced by reacting compound (1-1-3-1) with compound (3) or compound (4) in a solvent or without a solvent, and optionally in the presence of a base or an additive.

[0180] The amount of compound (3) or compound (4) used is in the range of 0.5 to 50 equivalents per equivalent of compound (1-1-3-1).

[0181] When a solvent is used, the solvent to be used may be any solvent inert to the reaction, and examples thereof include the solvents exemplified in Production Example 1.

[0182] The reaction can be carried out in the presence of a base. Examples of the base that can be used include the bases exemplified in Production Example 1. The amount (equivalent) of the base used can be 0.1 to 100 equivalents per equivalent of compound (1-1-3-1).

[0183] The reaction can be carried out in the presence of an additive. Examples of usable additives include 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol, 1-hydroxybenzotriazole, N,N-dimethyl-4-aminopyridine, etc. The amount (equivalent) of the additive used can be 0.1 to 100 equivalents relative to compound (1-1-3-1).

[0184] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0185] Some of the compounds (1-1-3-1) are known compounds, and some are commercially available. Others can be produced by general known methods described in the literature, such as those described in WO 2015 / 179441.

[0186] Step 2: Compound (1-1-3-3) can be obtained by reacting compound (1-1-3-2) with a reducing agent in a solvent or without a solvent.

[0187] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

[0188] The reaction can be carried out in the presence of a reducing agent. Examples of the reducing agent that can be used include sodium borohydride and lithium borohydride. The amount of the reducing agent used can be 0.25 to 50 equivalents per equivalent of compound (1-1-3-2).

[0189] The reaction temperature and reaction time were within the temperature and time ranges described in Production Example 1.

[0190] Step 3: Compound (1-1-3-4) can be obtained by reacting compound (1-1-3-3) with thionyl chloride in a solvent or without a solvent.

[0191] When a solvent is used, it is not necessary that the solvent used is inert to the reaction. Examples of the solvent include the solvents exemplified in Production Example 1.

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

[0193] Step 4: Compound (1-1-3) can be produced by reacting compound (1-1-3-4) with a halogenating agent according to a known method known in the literature, for example, the method described in WO 2004 / 050613. Examples of halogenating agents that can be used include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, bromine, and iodine. The halogenating agent can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (1-1-3-4).

[0194] The compound (1-1-5) used in Production Example 7 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 3.

[0195] [Reaction Scheme 3]

[0196] [wherein, X, R １ , R ２ and R ５ has the same meaning as above.] Step 1: Compound (1-1-5-2) can be produced, for example, by reacting compound (1-1-5-1) with compound (3) or compound (4) in accordance with the method of Step 1 of Reaction Scheme 2. Some of the compounds (1-1-5-1) are known compounds, and some are commercially available. In addition, other compounds can be produced in accordance with general known methods described in the literature, for example, the method described in WO 2015 / 179441, etc.

[0197] Step 2: Compound (1-1-5-3) can be produced, for example, by reacting compound (1-1-5-2) with a reducing agent according to the method of Step 2 of Reaction Scheme 2.

[0198] Step 3: Compound (1-1-5-4) can be produced, for example, by reacting compound (1-1-5-3) with thionyl chloride according to the method of Step 3 in Reaction Scheme 2.

[0199] Step 4: Compound (1-1-5) can be produced by reacting compound (1-1-5-4) with a halogenating agent, for example, according to the method of Step 4 in Reaction Scheme 2 or a known method, such as the method described in WO 2004 / 050613. Examples of halogenating agents that can be used include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, bromine, and iodine. The halogenating agent can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (1-1-5-4).

[0200] The compound (1-1-4) used in Production Example 6 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 4.

[0201] [Reaction Scheme 4]

[0202] [wherein, X, R １ and R ５ has the same meaning as above.] Compound (1-1-4) can be produced by reacting compound (1-1-3) with compound (9) in accordance with a known method known in the literature, for example, the method described in Organic Letters, 2021, Vol. 23, pp. 9649-9653.

[0203] Compound (9) is a known compound, and some of it is commercially available.

[0204] The compound (1-1-6) used in Production Example 8 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 5.

[0205] [Reaction Scheme 5]

[0206] [wherein, X, R ２ and R ５has the same meaning as above.] Compound (1-1-6) can be produced by reacting compound (1-1-5) with compound (9) in accordance with a known method known in the literature, for example, the method described in Organic Letters, 2021, Vol. 23, pp. 9649-9653.

[0207] Compound (9) is a known compound, and some of it is commercially available.

[0208] The compound (1-9) used in Production Example 12 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 6.

[0209] [Reaction Scheme 6]

[0210] [wherein, X, R １ , R ２ and R ５ has the same meaning as defined above.] Compound (1-9) can be produced by reacting compound (1-3-2) with compound (8-1) according to a known method known in the literature, for example, the method described in WO 2015026792.

[0211] Compound (1-3-2) can be produced according to the method of Step 1 in Reaction Scheme 2.

[0212] Some of the compounds (8-1) are known compounds, some of which are commercially available, and others can be prepared according to general synthetic methods for known compounds described in the literature.

[0213] The compound (1-1-5) used in Production Example 7 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 7.

[0214] [Reaction Scheme 7]

[0215] [wherein, X, R ２ and R ５has the same meaning as above.] Step 1: Compound (1-5-5) can be produced by reacting compound (3) with N-vinylformamide according to a known method known in the literature, for example, the method described in ACS Catalysis, 2021, Vol. 11, No. 18, pp. 11762-11773. Some of compound (3) are known compounds, and some are commercially available.

[0216] Step 2: Compound (1-5-4) can be produced by reacting compound (1-5-5) with compound (8-1) according to a known method, for example, the method described in Tetrahedron Letters, Vol. 43, No. 29, pp. 5079-5081, 2002. Some of compound (8-1) are known compounds, and some are commercially available. Other compounds can also be produced according to general methods for synthesizing known compounds described in the literature.

[0217] Step 3: Compound (1-1-5) can be produced by reacting compound (1-5-4) with a halogenating agent, for example, according to the method of Step 4 in Reaction Scheme 2 or a known method, such as the method described in WO 2004 / 050613. Examples of halogenating agents that can be used include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, bromine, and iodine. The halogenating agent can be used in an amount of 0.5 to 50 equivalents per equivalent of compound (1-1-5-4).

[0218] The compound (1-9) used in Production Example 12 can be produced, for example, according to the production route (reaction pathway) shown in the following reaction scheme 8.

[0219] [Reaction Scheme 8]

[0220] [In the formula, R １ , R ２ and R ５has the same meaning as above.] Step 1: Compound (1-9-1) can be produced by reacting compound (1-c) with trimethylsulfoxonium iodide in accordance with a known method known in the literature, for example, the method described in Synthesis, 2023, Vol. 55, No. 22, pp. 3825-3832. Some of compound (1-c) are known compounds, and some are commercially available. In addition, other compounds can be produced in accordance with a known method known in the literature, for example, the method described in Medicinal Chemistry Letters, 2014, Vol. 5, No. 7, pp. 748-753.

[0221] Step 2: Compound (1-9-2) can be produced by reacting compound (1-9-1) with ammonia according to a known method known in the literature, for example, the method described in Synthesis, Vol. 55, No. 22, pp. 3825-3832, 2023. Examples of compound (1-9-1) that can be used in these methods include the compounds shown below. However, the following are merely examples, and compound (1-9-1) is not limited to these.

[0222] Step 3: Compound (1-9) can be produced by reacting compound (1-9-2) with compound (3) according to a known method known in the literature, for example, the method described in Heterocycles, Vol. 90, No. 2, pp. 1124-1134, 2015. Examples of compound (1-9-2) that can be used in these methods include the compounds shown below. However, the following are merely examples, and compound (1-9-2) is not limited to these.

[0223] The compounds of the present invention can generally be used as agricultural and horticultural bactericides and fungicides against various diseases caused by Phytophthora, Oomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Fungi Imperfecti, bacteria or viruses.

[0224] The term "pathogenic fungus" refers to a microorganism that causes a plant disease, and specific examples thereof include, but are not limited to, the following microorganisms:

[0225] Taphrina spp. (Taphrina deformans) T. Pneumocystis spp., Geotrichum spp., Candida spp. sorbosa, Pichia spp., Pichia kluyveri, Capnodium spp., Fumago spp., Hypocapnodium spp., Cercospora spp apii、C. asparagus、C. beticola、C. capsici、C. carotae、C. khaki、C. kikuchii、C. zonata, Cercosporidium spp., Cladosporium spp. cucumerinum、C. variabile agents) Davidiella spp., Didymosporium spp., Heterosporium spp. berkeley、M. cerasella、M. fijiensis、M. fragariae、M. graminicola、M. nawae、M. pinodes、M. pomi、M. zingiberis, Mycovellosiella spp. nattrassii, Paracercospora spp., Paracercospora egenula, Phaeoisariopsis spp., Phaeoramularia spp., Pseudocercospora spp abelmoschi、P. fuligena、P. vitis, Pseudocercosporella spp., Ramichloridium spp., Septogloeum spp., Septoria spp. (e.g., Septoria albopunctata, S. apiicola, S. chrysanthemella, S. helianthi, S. obesa, etc.), Sphaerulina spp., Aureobasidium spp., Kabatiella spp., Plowrightia spp., Stigmina spp., Elsinoe spp. (e.g., Elsinoe ampelina, E. araliae, E. fawcettii, etc.), Sphaceloma spp. (e.g., Sphaceloma caricae, etc.), Ascochyta spp. (e.g., Ascochyta pisi, etc.), Corynespora spp. (e.g., Corynespora cassiicola, etc.), Leptosphaeria spp. (e.g., Leptosphaeria coniothyrium, L. maculans, etc.), Saccharicola spp., Phaeosphaeria spp. (e.g., Phaeosphaeria nodorum, etc.), Ophiosphaerella spp., Setophoma spp., Helminthosporium spp., Alternaria spp. (e.g., Alternaria alternata, A. brassicae, A. brassicicola, A. citri, A. dauci, A. helianthi, A. japonica, A. kikuchiana, A. mali, A. panax, A. porri, A. radicina, A. solani, etc.), Bipolaris spp. (e.g., Bipolaris sorghicola, etc.), Cochliobolus spp. (e.g., Cochliobolus heterostrophus, C. lunatus, C. miyabeanus, etc.), Curvularia spp. (e.g., Curvularia geniculata, C. verruculosa, etc.), Drechslera spp., Pleospora spp. (e.g., Pleospora herbarum, etc.), Pyrenophora spp.(from Pyrenophora graminea, P. teres (Setosphaeria spp.) Setosphaeria turcica (Setosphaeria turcica) Stemphylium spp. lycopersici、S. solani、S. vesicarium spp., Venturia spp., Venturia carpophila, V. vesicarium spp. Inaequalis、V. nashicola、V. pyrin activity) and Didymella spp. fabae, Hendersonia spp., Phoma spp., Phoma erratica var. mikan、P. exigua var. exigua、P. wasabiae active) Pyrenochaeta spp spp. Botryosphaeria berengeriana f. sp. piricola、B. dothidea activity) Dothiorella spp. Fusicoccum spp. Guignardia spp. Lasiodiplodia spp spp. Phyllosticta spp.(also) Phyllosticta zingiberis spp.(also) Schizothyrium pomi spp.Acrospermum spp.Leptosphaerulina spp.Aspergillus spp., Penicillium spp., Penicillium digitatum, P. spp. italicum、P. sclerotigenum activity) (Microsporum spp.) Trichophyton spp.(from Trichophyton mentagrophytes, T.S. rubrum spp., Histoplasma spp., Blumeria spp., Blumeria graminis f. sp. hordei、B. gf sp. tritici), Erysiphe spp. cichoracearum、E. c. var. cichoracearum、E. heraclei、E. low activity) Golovinomyces spp. latisporus spp., Leveillula spp., Leveillula taurica spp., Microsphaera spp., Oidium spp., Oidium neolycopersici spp., Phyllactinia spp.(Phyllactinia kakicola)P. mali、P. moricola, Podosphaera spp., Podosphaera fusca, P. leucotricha、P. pannosa、P. tridactyla var. tridactyla、P. xanthii activity) and Sphaerotheca spp. aphanis、S. fuliginea agent) and Uncinula spp. n. var. necator agent) (Uncinuliella spp.) Uncinuliella simulans var. simulans、U.S. s. var. tandae spp., Blumeriella jaapii spp., Cylindrosporium spp., Diplocarpon spp. mespili、D. rosae spp., Gloeosporium spp., Gloeosporium minus spp., Marssonina spp., Tapesia spp.yallundae, Lachnum spp., Scleromitrula spp., Botryotinia spp. byssoidea、B. cinerea、B. elliptic、B. fabae、B. squamosa agent) Ciborinia spp. Grovesinia spp. Monilia mumecola Monilinia spp. fructigena、M. laxa、M. mali、M. vaccinii-corymbosiactivity), Sclerotinia spp. homoeocarp、S. minor、S. sclerotiorum spp., Valdensia heterodoxa spp., Claviceps spp. sorghicola agent) Epichloe spp. Ephelis japonica Villosiclava virens Hypomyces spp. sp. mori、H. sf sp. low activity) Trichoderma spp.(also) Trichoderma viride activity) Calonectria spp.(an activity) Candelospora spp spp., Cylindrocladium spp., Fusarium spp. crookwellense、F. culmorum、F. cuneirostrum、F. oxysporum、F. of sp. adzukicola、F. of sp. allii、F. of sp. asparagus、F. of sp. potatoes、F. o. s. sp. cepae、F. of sp.colocasiae, F. of sp. conglutinans, F. of sp. cubense, F. of sp. cucumerinum, F. of sp. fabae, F. of sp. fragariae, F. of sp. lactucae, F. of sp. lagenariae, F. of sp. lycopersici, F. of sp. melongenae, F. of sp. melonis, F. of sp. nelumbinicola, F. of sp. niveum, F. of sp. radicis-lycopersici, F. of sp. raphani, F. of sp. spinaciae, F. sporotrichioides, F. solani, F. sf sp. cucurbitae, F. sf sp. eumartii, F. sf sp. glycines, F. sf sp. pisi, F. sf sp. Radicicola, F. virguliforme, etc.), Gibberella spp. (e.g. Gibberella avenacea, G. baccata, G. fujikuroi, G. zeae etc.), Haematonectria spp.、Nectria spp.、Ophionectria spp.、Caldariomyces spp.、Myrothecium spp.、Trichothecium spp.、Verticillium spp. (eg、Verticillium albo-atrum、V. dahliae、V. longisporum etc.), Ceratocystis spp. (eg Ceratocystis ficicola, C. fimbriata etc.), Thielaviopsis spp.(from Pestalotiopsis funerea, P. longiseta、P. neglecta、P. theae, Physalospora spp., Nemania spp., Nodulisporium spp., Rosellinia spp nivalis spp., Ophiostoma spp., Cryphonectria spp., Cryphonectria parasitica spp., Diaporthe spp. kyushuensis、D. nomurai、D. tanakae, Diaporthopsis spp., Phomopsis spp. fukushii、P. obscurans、P. vexans , Cryptosporella spp , Discula spp , Discula theae-sinensis , Gnomonia spp , Coniella spp , Coryneum spp , Greeneria spp , Melanconis spp., Cytospora spp., Leucostoma spp., Valsa spp.(also, Valsa ceratosperma activity) Tubakia spp., Monosporascus spp., Clasterosporium spp., Gaeumannomyces spp.(such as Gaeumannomyces graminis) Magnaporthe spp.(such as Magnaporthe grisea) Pyricularia spp.(such as Pyricularia zingiberis activity), Monilochaetes infuscans, Colletotrichum spp. capsici、C. cereal、C. destructivum、C. fragariae、C. lindemuthianum、C. nigrum、C. orbiculare、C.spinaciae, etc.), Glomerella spp. (e.g., Glomerella cingulata, etc.), Khuskia oryzae, Phyllachora spp. (e.g., Phyllachora pomigena, etc.), Ellisembia spp., Briosia spp., Cephalosporium spp. (e.g., Cephalosporium gramineum, etc.), Epicoccum spp., Gloeocercospora sorghi, Mycocentrospora spp., Peltaster spp. (e.g., Peltaster fructicola, etc.), Phaeocytostroma spp., Phialophora spp. (e.g., Phialophora gregata, etc.), Pseudophloeosporella dioscoreae, Pseudoseptoria spp., Rhynchosporium spp. (e.g., Rhynchosporium secalis, etc.), Sarocladium Fungi of the Ascomycota phylum, such as Coleophoma spp., Helicoceras oryzae, etc. Septobasidium spp. (e.g., Septobasidium bogoriense, S. tanakae, etc.), Helicobasidium spp. (e.g., Helicobasidium longisporum, etc.), Coleosporium spp. (e.g., Coleosporium plectranthi, etc.), Cronartium spp., Phakopsora spp. (e.g., Phakopsora artemisiae, P. nishidana, P. pachyrhizi, etc.), Physopella spp. (e.g., Physopella ampelopsidis, etc.), Kuehneola spp. (e.g., Kuehneola japonica, etc.), Phragmidium spp. (e.g., Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae, etc.), Gymnosporangium spp.(e.g., Gymnosporangium asiaticum, G. yamadae, etc.), Puccinia spp. (e.g., Puccinia allii, P. brachypodii var. poae-nemoralis, P. coronata, P. c. var. coronata, P. cynodontis, P. graminis, P. g. subsp. graminicola, P. hordei, P. horiana, P. kuehnii, P. melanocephala, P. recondita, P. striiformis var. striiformis, P. tanaceti var. tanaceti, P. tokyensis, P. zoysiae, etc.), Uromyces spp. (e.g., Uromyces phaseoli var. azukicola, U. p. var. phaseoli, Uromyces viciae-fabae var. viciae-beans etc.), Naohidemyces vaccinii, Nyssopsora spp., Leucotelium spp., Tranzschelia spp. (eg Tranzschelia discolor, etc.), Aecidium spp., Blastospora spp. spp. (for example, Ustilago maydis, U. nuda etc.), Entyloma spp., Exobasidium spp. (eg, Exobasidium reticulatum, E. vexans etc.), Microstroma spp., Tilletia spp. (eg, Tilletia caries, T. controversial、T. laevis etc.), Itersonilia spp. (for example, Itersonilia perplexans etc.), Cryptococcus spp., Bovista spp.(e.g., Bovista dermoxantha, etc.), Lycoperdon spp. (e.g., Lycoperdon curtisii, L. perlatum, etc.), Conocybe spp. (e.g., Conocybe apala, etc.), Marasmius spp. (e.g., Marasmius oreades, etc.), Armillaria spp., Helotium spp., Lepista spp. (e.g., Lepista subnuda, etc.), Sclerotium spp. (e.g., Sclerotium cepivorum, etc.), Typhula spp. (e.g., Typhula incarnata, T. ishikariensis var. ishikariensis, etc.), Athelia spp. (e.g., Athelia rolfsii, etc.), Ceratobasidium spp. (e.g., Ceratobasidium cornigerum, etc.), Ceratorhiza spp., Rhizoctonia Fungi of the phylum Basidiomycota such as Rhizoctonia solani, Thanatephorus spp. (e.g., Thanatephorus cucumeris), Laetisaria spp., Waitea spp., Fomitiporia spp., Ganoderma spp., Chondrostereum purpureum, and Phanerochaete spp. Fungi of the phylum Chitridiomycota such as Olpidium spp. Fungi of the phylum Blastocladiomycota such as Physoderma spp. Fungi of the subphylum Mucoromycotina, such as Choanephora spp., Choanephoroidea cucurbitae, Mucor spp. (e.g., Mucor fragilis, etc.), and Rhizopus spp. (e.g., Rhizopus arrhizus, R. chinensis, R. oryzae, R. stolonifer var. stolonifer, etc.). Plasmodiophora spp.Protozoa of the phylum Cercozoa such as (for example, Plasmodiophora brassicae, etc.), Spongospora subterranea f. sp. Subterranea, etc. Aphanomyces spp. (for example, Aphanomyces cochlioides, A. raphani, etc.), Albugo spp. (for example, Albugo macrospora, A. wasabiae, etc.), Bremia spp. (for example, Bremia lactucae, etc.), Hyaloperonospora spp., Peronosclerospora spp., Peronospora spp. (for example, Peronospora alliariae - wasabi, P. chrysanthemi - coronarii, P. destructor, P. farinosa f. sp. spinaciae, P. manshurica, P. parasitica, P. sparsa, etc.), Plasmopara spp. (for example, Plasmopara halstedii, P. nivea, P. viticola, etc.), Pseudoperonospora spp. (for example, Pseudoperonospora cubensis, etc.), Sclerophthora spp., Phytophthora spp. (for example, Phytophthora cactorum, P. capsici, P. citricola, P. citrophthora, P. cryptogea, P. fragariae, P. infestans, P. melonis, P. nicotianae, P. palmivora, P. porri, P. sojae, P. syringae, P. vignae f. sp. adzukicola, etc.), Pythium spp. (for example, Pythium afertile, P. aphanidermatum, P. apleroticum, P. aristosporum, P. arrhenomanes, P. buismaniae, P. debaryanum, P. graminicola, P. horinouchiense, P. irregulare, P. iwayamai, P.myriotylum, P. okanoganense, P. paddicum, P. paroecandrum, P. periplocum, P. spinosum, P. sulcatum, P. sylvaticum, P. ultimum var. ultimum, P. vanterpoolii, P. vexans, P. Oomycetes of the phylum Heterokontophyta, such as volutum, etc. Gram-positive fungi of the phylum Actinobacteria, such as Clavibacter spp. (e.g., Clavibacter michiganensis subsp. michiganensis, etc.), Curtobacterium spp., Leifsonia spp. (e.g., Leifsonia xyli subsp. xyli, etc.), Streptomyces spp. (e.g., Streptomyces ipomoeae, etc.). Gram-positive bacteria of the Firmicutes phylum, such as Clostridium sp. Gram-positive bacteria of the Tenericutes phylum, such as Phytoplasma. Rhizobium spp. (e.g., Rhizobium radiobacter, etc.), Acetobacter spp., Burkholderia spp. (e.g., Burkholderia andropogonis, B. cepacia, B. gladioli, B. glumae, B. plantarii, etc.), Acidovorax spp. (e.g., Acidovorax avenae subsp. avenae, A. a. subsp. citrulli, A. konjaci, etc.), Herbaspirillum spp., Ralstonia spp. (e.g., Ralstonia solanacearum, etc.), Xanthomonas spp. (e.g., Xanthomonas albilineans, X. arboricola pv. pruni, X. axonopodis pv. vitians, X. campestris pv. campestris, X. c. pv. cucurbitae, X. c. pv. glycines, X. c. pv.mangiferaeindicae, X. c. pv. nigromaculans, X. c. pv. vesicatoria, X. citri subsp. citri, X. oryzae pv. pv. glycinea, P. syringae, P. s. pv. actinidiae, P. s. pv. eriobotryae, P. s. pv. helianthi, P. s. pv. lachrymans, P. s. pv. maculicola, P. s. pv. mori, P. s. pv. morsprunorum, P. s. spinaciae, P. s. Gram-negative bacteria of the Proteobacteria phylum, such as P. pv. syringae, P. s. pv. theae, P. viridiflava, etc.), Rhizobacter spp., Brenneria spp. (e.g., Brenneria nigrifluens, etc.), Dickeya spp. (e.g., Dickeya dianthicola, D. zeae, etc.), Erwinia spp. (e.g., Erwinia amylovora, E. rhapontici, etc.), Pantoea spp., and Pectobacterium spp. (e.g., Pectobacterium atrosepticum, P. carotovorum, P. wasabiae, etc.).

[0226] Specific examples of plant diseases caused by infection and proliferation of these pathogenic fungi include, but are not limited to, the following plant diseases:

[0227] Peach leaf curl (Taphrina deformans), plum pockets (Taphrina pruni), asparagus leaf spot (Cercospora asparagi), sugar beet leaf spot (Cercospora beticola), bell pepper leaf spot (Cercospora capsici), persimmon angular leaf spot (Cercospora kaki), soybean purple stain (Cercospora kikuchii), peanut brown leaf spot (Mycosphaerella arachidis), cherry brown hole (Cylindrosporium cerasella, Blumeriella jaapii), black sigatoka disease (Mycosphaerella fijiensis), yellow sigatoka disease (Mycosphaerella musicola), Speckled leaf blotch of wheat (Mycosphaerella graminicola), Circular leaf spot of persimmon (Mycosphaerella nawae), Mycosphaerella blight of pea (Mycosphaerella pinodes), Leaf spot of ginger (Mycosphaerella zingiberis), Leaf mold of tomato (Mycovellosiella fulva), Leaf mold of eggplant (Mycovellosiella nattrassii), Leaf mold of tomato (Cercospora fuligena), Isariopsis leaf spot of grapevine (Pseudocercospora vitis), Leaf spot of Chinese cabbage (Pseudocercosporella capsellae), Leaf spot of chrysanthemum (Septoriachrysanthemella), Chrysanthemum leaf blight (Septoria obesa), Grape anthracnose (Elsinoe ampelina), Araliae scab anthracnose (Elsinoe araliae), Citrus scab (Elsinoe fawcettii), Pea leaf spot (Ascochyta pisi), Cucumber leaf spot (Corynespora cassiicola), Rose stem canker (Leptosphaeria coniothyrium), Wheat glume blotch (Leptosphaeria nodorum), Rose leaf spot (Alternaria alternata), Cabbage leaf spot (Alternaria brassicae), Carrot leaf blight (Alternaria dauci), Pear black spot (Alternaria kikuchiana), Alternaria blotch (Alternaria mali) on apple, Alternaria leaf spot (Alternaria porri) on leek, Target spot (Bipolaris sorghicola) on sorghum, Southern leaf blight (Cochliobolus heterostrophus) on corn, Brown spot (Cochliobolus miyabeanus) on rice, Tip blight (Pleospora herbarum) on garlic, Stripe leaf blight (Pyrenophora graminea) on barley, Net blotch (Pyrenophora teres) on barley, Leaf blight (Setosphaeria turcica) on sorghum, Northern leaf blight (Setosphaeria turcica) on corn, Leaf spot (Stemphylium erythrorhizae) on asparagusbotryosum), Scab of Rosaceae (Prunus subfamily) (Venturia carpophila), Scab of apple (Venturia inaequalis), Scab of pear (Venturia nashicola), Gummy stem blight of Cucurbitaceae (Didymella bryoniae), Leaf spot of burdock (Phoma exigua var. exigua), Streak of wasabi (Phoma wasabiae), Ring rot of Rosaceae (Prunus subfamily) (Botryosphaeria berengeriana f. sp. piricola), Soft rot of kiwifruit (Botryosphaeria dothidea, Lasiodiplodia theobromae, Diaporthe sp.), Common green mold of citrus (Penicillium digitatum), Blue mold of citrus (Penicillium italicum), powdery mildew that occurs on various crops, barley powdery mildew (Blumeria graminis f. sp. hordei), wheat powdery mildew (Blumeria graminis f. sp. tritici), cucumber powdery mildew (Erysiphe betae, Leveillula taurica, Oidium sp., Podosphaera xanthii), eggplant powdery mildew (Erysiphe cichoracearum, Leveillula taurica, Sphaerotheca fuliginea), carrot and parsley powdery mildew (Erysiphe heraclei), pea powdery mildew (Erysiphe pisi), tomato powdery mildew (Leveillula taurica, Oidium neolycopersici, Oidium sp.), pepper powdery mildew (Leveillula taurica), pumpkin powdery mildew (Oidium sp., Podosphaera xanthii), bitter gourd powdery mildew (Oidium sp.), persimmon powdery mildew (Phyllactiniakakicola), burdock powdery mildew (Podosphaera fusca), apple powdery mildew (Podosphaera leucotricha), rose powdery mildew (Podosphaera pannosa, Uncinuliella simulans var. simulans, U. s. var. tandae), zucchini and melon powdery mildew (Podosphaera xanthii), strawberry powdery mildew (Sphaerotheca aphanis var. aphanis), watermelon and melon powdery mildew (Sphaerotheca fuliginea), grape powdery mildew (Uncinula necator, U. n. var. necator), apple blotch (Diplocarpon mali), rose black spot (Diplocarpon rosae), onion gray mold neck rot (Botrytis allii), gray mold, Botrytis Blight (Botrytis cinerea), leaf blight of Chinese chives (Botrytis cinerea, B. byssoidea, B. squamosa), chocolate spot of broad beans (Botrytis cinerea, B. elliptica, B. fabae), brown rot of Rosaceae (Monilinia fructicola, M. fructigena, M. laxa), blossom blight of apples (Monilinia mali), dollar spot of shiba (Sclerotinia homoeocarpa), cottony rot, stem rot (Sclerotinia sclerotiorum), false smut of rice (Villosiclava virens), root necrosis of soybeans (Calonectria ilicicola), Fusarium blight of wheat (Fusarium crookwellense, F. culmorum, Gibberella avenacea, G. zeae,Monographella nivalis), Fusarium blight of barley (Fusarium culmorum, Gibberella avenacea, G. zeae), Dry rot of taro (Fusarium oxysporum, F. solani f. sp. radicicola), Brown rot of yam (Fusarium oxysporum, F. solani f. sp. pisi, F. s. f. sp. radicicola), Fusarium wilt of adzuki bean (Fusarium oxysporum f. sp. adzukicola), Fusarium basal rot of Chinese chive (Fusarium oxysporum f. sp. allii, F. solani f. sp. radicicola), Stem rot of sweet potato (Fusarium oxysporum f. sp. batatas, F. solani), Dry rot of dasheen (Fusarium oxysporum f. sp. colocasiae), Yellows of cabbage and Komatsuna (Fusarium oxysporum f. sp. conglutinans), Panama disease of banana (Fusarium oxysporum f. sp. cubense), Fusarium wilt of strawberry (Fusarium oxysporum f. sp. fragariae), Root rot of lettuce (Fusarium oxysporum f. sp. lactucae), Fusarium wilt of watermelon (Fusarium oxysporum f. sp. lagenariae, F. o. f. sp. niveum), Fusarium wilt of tomato (Fusarium oxysporum f. sp. lycopersici), Fusarium wilt of melon (Fusarium oxysporum f. sp. melonis), Yellows of radish (Fusarium oxysporum f. sp.raphani), spinach wilt (Fusarium oxysporum f. sp. spinaciae), soybean sudden death syndrome (Fusarium solani f. sp. Glycines, Fusarium virguliforme), rice "Bakanae" disease (Gibberella fujikuroi), radish Verticillium black spot (Verticillium albo-atrum, V. dahliae), tomato, eggplant, and butterbur Verticillium wilt (Verticillium dahliae), fig root blight (Ceratocystis ficicola), sweet potato black rot (Ceratocystis fimbriata), tea gray blight (Pestalotiopsis longiseta, P. theae), Chestnut canker (Endothia parasitica), Citrus black spot (Melanose) (Diaporthe citri), Asparagus stem blight (Phomopsis asparagi), Pear canker (Phomopsis fukushii), Eggplant brown spot (Phomopsis vexans), Tea anthracnose (Discula theae-sinensis), Apple canker (Valsa ceratosperma), Rice blast (Magnaporthe grisea), Strawberry crown rot (Colletotrichum acutatum, C. fragariae, Glomerella cingulata), Apple bitter rot (Colletotrichum acutatum, Glomerella cingulata), Anthracnose (Colletotrichum acutatum, Glomerella)cingulata), plum anthracnose (Anthracnose, Colletotrichum acutatum), grape ripening rot (Colletotrichum acutatum, Glomerella cingulata), garland chrysanthemum anthracnose (Anthracnose, Colletotrichum acutatum), kidney bean anthracnose (Anthracnose, Colletotrichum lindemuthianum), cucurbit anthracnose (Anthracnose, Colletotrichum orbiculare), yam anthracnose (Anthracnose, Glomerella cingulata), chestnut anthracnose (Anthracnose, Glomerella cingulata), persimmon anthracnose (Anthracnose, Glomerella cingulata), adzuki bean brown stem rot (Phialophora gregata), Chinese yam leaf spot (Pseudophloeosporella dioscoreae), barley scald (Rhynchosporium secalis), wheat brown rust (Puccinia recondita), wheat stripe rust (Puccinia striiformis), rust that occurs on various crops, fig rust (Phakopsora nishidana), soybean rust (Phakopsora pachyrhizi), rose rust (Kuehneola japonica, Phragmidium fusiforme, P. mucronatum, P. rosae-multiflorae), pear red rust (Gymnosporangium asiaticum), apple red rust (Gymnosporangium yamadae), lecithin rust (Puccinia allii), chrysanthemum white rust (Puccinia horiana), chrysanthemum black rust (Puccinia tanaceti var. tanaceti), broad bean rust (Uromyces viciae-fabae var. viciae-fabae), sugarcane smut (Sporisoriumscitamineum), Corn smut (Ustilago maydis), Barley loose smut (Ustilago nuda), Tea net blister blight (Exobasidium reticulatum), Tea blister blight (Exobasidium vexans), Stem rot, Southern blight (Athelia rolfsii), Chrysanthemum root and stem rot (Ceratobasidium cornigerum, Rhizoctonia solani), Ginger sheath blight (Rhizoctonia solani), Cabbage seedling damping-off (Rhizoctonia solani), Mitsuba damping-off (Rhizoctonia solani), Lettuce bottom rot (Rhizoctonia solani), Turfgrass brown patch, large patch (Rhizoctonia solani), Rice sheath blight Beet blight (Thanatephorus cucumeris), sugar beet root rot (Thanatephorus cucumeris), sugar beet leaf blight (Thanatephorus cucumeris), fig black mold (Rhizopus stolonifer var. stolonifer), cruciferous vegetables clubroot (Plasmodiophora brassicae), sugar beet black root rot (Aphanomyces cochlioides), cruciferous vegetables white rust (Albugo macrospora), downy mildew that occurs on various crops, lettuce downy mildew (Bremia lactucae), garland chrysanthemum downy mildew (Peronospora chrysanthemi-coronarii), onion and leek downy mildew (Peronospora destructor), spinach downy mildew (Peronospora farinosa f. sp. spinaciae), soybean downy mildew (Peronosporamanshurica), Crucifer downy mildew (Peronospora parasitica), Rose downy mildew (Peronospora sparsa), Sunflower downy mildew (Plasmopara halstedii), Honeybee downy mildew (Plasmopara nivea), Grape downy mildew (Plasmopara viticola), Cucurbit downy mildew (Pseudoperonospora cubensis), Aralia root rot (Phytophthora cactorum), Watermelon brown rot (Phytophthora capsici), Pumpkin late blight (Phytophthora capsici), Bell pepper late blight (Phytophthora capsici), Watermelon late blight (Phytophthora cryptogea), Tomato and potato late blight (Phytophthora infestans), Fig white powdery mildew rot (Phytophthora palmivora), Leaf blight of onion (Phytophthora porri), Phytophthora root and stem rot of soybean (Phytophthora sojae), Phytophthora stem rot of adzuki beans (Phytophthora vignae f. sp. adzukicola), Damping-off of spinach (Pythium aphanidermatum, P. myriotylum, P. paroecandrum, P. ultimum var. ultimum), Root rot of konjac (Pythium aristosporum), Browning root rot of corn (Pythium arrhenomanes, P. graminicola), Damping-off of cabbage seedlings (Pythium buismaniae, P. myriotylum), Root rot of ginger (Pythium myriotylum), Ginger rhizome rot Rootrot (Pythium myriotylum, P. ultimum var. ultimum), carrot brown blotted root rot (Pythium sulcatum), tomato bacterial canker (Clavibacter michiganensis subsp. michiganensis), potato scab (Streptomyces spp.), rose crown gall (Rhizobium radiobacter), sorghum bacterial stripe (Burkholderia andropogonis), onion soft rot (Burkholderia cepacia, Pseudomonas marginalis pv. marginalis, Erwinia rhapontici), rice bacterial grain rot (Burkholderia gladioli, B. glumae), watermelon bacterial fruit blotch (Acidovorax avenae subsp. Bacterial leaf blight (Acidovorax konjaci), Bacterial leaf blight (Ralstonia solanacearum), Bacterial shot hole (Xanthomonas arboricola pv. pruni, Pseudomonas syringae pv. syringae, Brenneria) nigrifluens), Bacterial leaf spot (Xanthomonas arboricola pv. pruni), Bacterial leaf spot (Xanthomonas axonopodis pv. vitians), Black rot (Xanthomonas campestris pv. campestris), Bacterial pustule (Xanthomonas campestris pv. glycines), burdock black spot bacterial disease Bacterialspot (Xanthomonas campestris pv. nigromaculans), bacterial spot of pepper (Xanthomonas campestris pv. vesicatoria), citrus canker (Xanthomonas citri subsp. citri), garlic spring rot (Pseudomonas cichorii, P. marginalis pv. marginalis, Erwinia sp.), lettuce bacterial rot (Pseudomonas cichorii, P. marginalis pv. marginalis, P. viridiflava), kiwifruit bacterial blossom blight (Pseudomonas marginalis pv. marginalis, P. syringae pv. syringae, P. viridiflava), kiwifruit bacterial canker (Pseudomonas syringae pv. actinidiae), Loquat canker (Pseudomonas syringae pv. eriobotryae), Bacterial spot of Cucurbitaceae (Pseudomonas syringae pv. lachrymans), Bacterial black spot of Brassicaceae (Pseudomonas syringae pv. maculicola), Plum canker (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), Tea shoot blight (Pseudomonas syringae pv. theae), Onion soft rot (Dickeya sp., Pectobacterium carotovorum), Fire blight of Rosaceae (Poidomonaceae) (Erwinia amylovora), Konjac soft rot (Pectobacterium carotovorum), Bacterial softrot (Pectobacterium carotovorum).

[0228] The development of control agents for diseases of agricultural and horticultural crops has progressed, and a wide variety of pesticides have been put to practical use to date. However, due to the long-term use of these pesticides, pathogens have recently acquired drug resistance, making it increasingly difficult to control them with conventionally used fungicides. In addition, some existing pesticides are highly toxic, and some persist in the environment for long periods of time, resulting in the emergence of problems of ecosystem disruption. Under these circumstances, the compounds of the present invention have excellent control activity against many pathogens and are highly safe for target crops. Furthermore, the compounds of the present invention can exert sufficient control effects even against pathogens that have acquired resistance to existing fungicides. Furthermore, the compounds of the present invention do not cause phytotoxicity to target crops, have little adverse effect on mammals, fish, and beneficial insects, and have low residual properties and a low environmental impact.

[0229] In addition to being used as an agricultural and horticultural fungicide, the compound of the present invention can also be used as a medical antibacterial agent and an antibacterial agent for animals, which are used as antifungal agents or agents for controlling internal parasites; an antibacterial and antifungal agent for wood, paper / pulp, adhesives / paints, fibers, leather, etc.; and an industrial fungicide, such as for cooling water channels in manufacturing plants.

[0230] Examples of pathogenic bacteria that can be used as medical antibacterial agents or veterinary antibacterial agents include, but are not limited to, tinea fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformans, Gram-negative bacteria such as Escherichia coli, Pseudomonas aeruginosa, and Haemophilus influenzae, and Gram-positive bacteria such as Staphylococcus aureus and Streptococcus pyogenes.

[0231] Examples of fungal strains that can be used as antibacterial and antifungal agents include, but are not limited to, wood-rotting fungi such as Tyromyces palustris and Coriolus versicolor, and material-deteriorating microorganisms such as Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, and Myrothecium verrucaria.

[0232] Examples of fungal strains that can be used as industrial fungicides include, but are not limited to, slime fungi such as Sphaerotilis natans and Zoogloea ramigera.

[0233] The compounds of the present invention can be used as agents for controlling internal parasites in livestock, poultry, pets, etc., in addition to being used as agricultural and horticultural fungicides.

[0234] Specific examples of target internal parasites include, but are not limited to, the following:

[0235] Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostomum, Oesophagostomum, Chabertia, Trichuris, Strongylus ylus), Trichonema, Dictyocaulus, Capillaria, Heterakis, Toxocara, Ascaridia, Oxyuris, Ancylostoma, Uncinaria, Toxascaris, Parascaris, and other nematodes; Filariidae nematodes such as Wuchereria, Brugia, Onchoceca, Dirofilaria, and Loa; Dracunculidae nematodes such as Deacunculus; Dipylidium caninum, Taenia taeniaeformis, Taenia solium, Taenia saginata, Hymenolepis diminuta, Moniezia benedeni, Diphyllobothrium latum, Diphyllobothrium erinacei, Echinococcus granulosus Tapeworms such as Echinococcus granulosus and Echinococcus multilocularis; Fasciola hepatica (F.trematodes such as Paragonimus gigantica, Paragonimus westermanii, Fasciolopsic bruski, Eurytrema pancreaticum, E. coelomaticum, Clonorchis sinensis, Schistosoma japonicum, Schistosoma haematobium, Schistosoma mansoni; ovinoidalis); Trypanosomsa cruzi, Leishmania, Plasmodium, Babesia, Trichomonadidae, Histomanas, Giardia, Toxoplasma, Entamoeba histolytica, Theileria, etc.

[0236] The compounds of the present invention can be used as antifungal agents in addition to being used as agricultural and horticultural fungicides.

[0237] Specific examples of pathogenic bacteria that can be targeted by antifungal agents include, but are not limited to, the following.

[0238] Trichophyton fungi such as Trichophyton rubrum and Trichophyton mentagrophytes, Candida fungi such as Candida albicans, Aspergillus fungi such as Aspergillus fumigatus, Cryptococcus fungi such as Cryptococcus neoformas, and the like.

[0239] When the compound of the present invention is applied as a plant disease and plant pest control agent, it is usually mixed with a suitable solid or liquid carrier, and if desired, surfactants, penetrants, spreaders, thickeners, antifreeze agents, binders, anticaking agents, disintegrants, or antidegradants are further added, and the compound can be used in any formulation, such as a soluble concentrate, emulsifiable concentrate, wettable powder, water-soluble powder, water-dispersible granules, water-soluble granules, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granules, or gel. Furthermore, from the viewpoint of labor saving and improved safety, the above-mentioned formulations of any formulation can be used sealed in a water-soluble package.

[0240] Examples of solid carriers include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride; synthetic silicic acid; and synthetic silicates.

[0241] Examples of liquid carriers include alcohols such as ethylene glycol, propylene glycol, and isopropanol; aromatic hydrocarbons such as xylene, alkylbenzene, and alkylnaphthalene; ethers such as butyl cellosolve; ketones such as cyclohexanone; esters such as γ-butyrolactone; acid amides such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil; and water. These solid and liquid carriers may be used alone or in combination of two or more.

[0242] Examples of surfactants include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formalin condensates of naphthalenesulfonic acid, salts of formalin condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfates or phosphates, polyoxyethylene styrylphenyl ether sulfates or phosphates, polycarboxylates, and polystyrenesulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; and amphoteric surfactants such as amino acid types and betaine types.

[0243] The content of these surfactants is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight per 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

[0244] When the compound of the present invention is used as a pesticide, it may be mixed with other herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. at the time of formulation or spraying, if necessary.

[0245] In particular, by applying it in combination with other pesticides or plant hormones, cost reductions can be achieved by reducing the amount of applied drug, and the synergistic action of the mixed drug can be expected to broaden the fungicidal and insecticidal spectrum or to achieve a higher pest control effect.In this case, it is also possible to combine it with multiple known pesticides at the same time.

[0246] In one embodiment, types of pesticides that can be mixed with the compound of the present invention include, for example, compounds described in The Pesticide Manual, 18th Edition, 2018. Specific examples of their common names are as follows: However, the pesticides that can be mixed are not necessarily limited to these.

[0247] Fungicides: acibenzolar-S-methyl, acypetacs, aldimorph, allyl alcohol, ametoctradin, aminopyrifen, amisulbrom, amobam, ampropylfos, anilazine, azaconazole, azithiram, azoxystrobin, barium polysulfide polysulfide), benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron, benthiavalicarb-isopropyl, benthiazole, benzamacril, benzamorph, benzovindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture mixture), boscalid (boscalid), bromoconazole (bromoconazole), bupirimate (bupirimate), buthiobate (buthiobate), butylamine (butylamine), lime sulfur mixture (calcium polysulfide), captafol (captafol), captan (captan), carbamorph (carbamorph), carbendazim (carbendazim), carboxin (carboxin), carpropamid (carpropamid), carvone (carvone), cheshunt mixture (cheshunt mixture), chinomethionate (chinomethionat),Chlobenthiazone, chloraniformethane, chloranil, chlorfenazole, chloroneb, chloroinconazide, chloropicrin, chlorothalonil, chlorquinox, chlozolinate, climbazole, copper acetate, copper carbonate, basic, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper sulfate, copper sulfate, basic, copper zinc chromate chromate), coumoxystrobin, cresol, cufraneb, cuprobam, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole, cyprodinil, cyprofuram, dazomet, debacarb, decafentin, dehydroacetate acid), dichlobentiazox, dichlofluanid, diclone, dichlorophen, dichlozoline, diclobutrazol,Diclocymet (diclocymet), diclomezine (diclomezine), dicloran (dicloran), diethofencarb (diethofencarb), difenoconazole (difenoconazole), diflumetorim (diflumetorim), dimethirimol (dimethirimol), dimethomorph (dimethomorph), dimoxystrobin (dimoxystrobin), diniconazole (diniconazole), diniconazole-M (diniconazole-M), dinobut Dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinosulfon, dinoterbone, diphenylamine, dipymetitrone, dipyrithione, disulfiram, ditalimfos, dithianon, DENON DNOC, dodemorph, dodine, drazoxolon, edifenphos, enestrobin, enoxastrobin, epoxiconazole, ethaboxam, etaconazole, etem, ethirimol, ethoxyquin, etridiazole azole), famoxadone, fenamidone, fenaminosulf, phenaminestrobin, fenapanil, fenarimol, fenbuconazole, feneptamidoquine, fenfuram, fenhexamid, fenitropan,Fenopyramid, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, florylpicoxamid, fluazinam, f lubeneteram (flubeneteram), fludioxonil (fludioxonil), flufenoxadiazam (flufenoxadiazam), flufenoxystrobin (flufenoxystrobin), fluindapyr (fluindapyr), flumethylsulforim (flumetylsulforim), flumetover (flumetover), flumorph (flumorph), fluopicolide (fluopicolide), fluopimomide (fluopyram), Fluorimide (fluoroimide), fluotrimazole (fluotrimazole), fluoxapiprolin (fluoxapiprolin), fluoxastrobin (fluoxastrobin), fluoxytioconazole (fluoxytioconazole), fluquinconazole (fluquinconazole), flusilazole (flusilazole), flusulfamide (flusulfamide), flutolanil (flutolanil), flutianil (flutianil), flutriafol (flutriafol), fluxapyroxad (fluxapyroxad), folpet (folpet), fosetyl - aluminum (fosetyl-aluminium), fthalide (fthalide), fuberidazole (fuberidazole), furalaxyl (furalaxyl), furametpyr (furametpyr), furcarbanil (furcarbanil), fluconazole (furconazole), fluconazole - cis (furconazole-cis),Flumecyclox, furophanate, galquin, glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene, hexaconazole, hexylthiofos, oxyquinoline sulfate (8-hydroxyquinoline sulfate), sulfate), hymexazol, imazalil, imibenconazole, iminoctadine-albesilate, iminoctadine-triacetate, inpyrfluxam, iodocarb, ipconazole, ipfentrifluconazole, ipflufenoquin, iprobenfos, iprodione, iprovalicarb, isofetamide, isofetamide, isofleucipram, Sotianil (isotianil), isoprothiolane (isoprothiolane), isopyrazam (isopyrazam), isovaledione (isovaledione), kasugamycin (kasugamycin), kresoxim-methyl (kresoxim-methyl), laminarin (laminarin), mancopper (mancopper), mancozeb (mancozeb), mandestrobin (mandestrobin), mandipropamid (mandipropamid), maneb (maneb), mebenil (mebenil), mecarbinzid (mecarbinzid), mefentrifluconazole (mefentrifluconazole), mepanipyrim (mepanipyrim), mepronil (mepronil), meptyldinocap (meptyldinocap),Metalaxyl, metalaxyl-M, metam, metarylpicoxamid, metazoxolone, metconazole, methasulfocarb, metofuroxam, methyltetraprole, metiram, metominostrobin, metrafenone, metsulfovax, milneb, myclobutanil, myclozolin, nabam, naftifine, natamycin, organic nickel (nickel bis (dimethyldithiocarbamate), nitrostyrene, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxathiapiprolin, oxyquinoline copper, oxpoconazole fumarate fumarate), oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad, orthophenylphenol (2-phenylphenol), phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxins,Polyoxin-D, potassium azide, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb hydrochloride hydrochloride), propiconazole, propineb, proquinazid, prothiocarb, pyrazophos, pyribencarb, pyrifenox, pyrimethanil, pyriminostrobin, pyroquilon, prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrapropion e), pyraziflumid, pyridaclomethyl, pyridinitril, pyriophenone, pyrisoxazole, pyroxychlor, pyroxyfur, quinacetol-sulfate, quinazamid, quinconazole, quinoxyfen, quinofumelin, quintozene, rabenzazole, salicylanilide, seboctylamine, sedaxane, silthiofam, simeconazole,Sodium hydrogen carbonate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, tefloctalam, tecnazene, tecoram, tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiophanate e), thiophanate-methyl, thiuram, tiadinil, tioximid, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltin oxide oxide), trichlamide, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, vinclozolin, zalilamid, zinc naphthenate, zinc sulfate, zineb, ziram,Zoxamide, shiitake mycelium extract, shiitake fruiting body extract, etc.

[0248] Insecticides: abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopyropen, afoxolaner, alanycarb, aldicarb, allethrin, alpha-cypermethrin, alpha-endosulfan, amidoflumet, amitraz, azamethiphos, azinphos-ethyl, azinphos-methyl, azocyclotin, Bacillus thuringiensis thuringiensis), bendiocarb, benfluthrin, benfuracarb, bensultap, benzoximate, benzpyrimoxan, beta-cyfluthrin, beta-cypermethrin, bifenazate, bifenthrin, bioallethrin, bioresmethrin smethrin), bistrifluron, bisulflufen, broflanilide, bromopropylate, buprofezin, butocarboxim, carbaryl, carbofuran, carbosulfan, cartap, chinomethionate, chlorantraniliprole,Chlorethoxyfos (chlorethxyfos), chlorfenapyr (chlorfenapyr), chlorfenvinphos (chlorfenvinphos), chlorfluazuron (chlorfluazuron), chlormephos (chlormephos), chlorobenzilate (chlorobezilate), chloroprallethrin (chloroprallethrin), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl (chlorpyrifos-methyl), chromafenozide (chromafenozide), clofentezine (clofentezine), clothianidin (clothianidin), cyanophos (cyanophos), cyantraniliprole (cyantraniliprole), cybenzoxasulfyl (cybenzoxasulfyl), cyclaniliprole (cyclaniliprole), cycloprothrin (cycloprothrin), cyenopyrafen (cyenopyrafen), cyetpyrafen (cyetpyrafen), cyflumetofen (cyflumet ofen), cyfluthrin, cyhalodiamide, cyhalothrin, cyhexatine, cypermethrin, cyphenothrin, cyproflanilide, cyromazine, deltamethrin, diaclor, diafenthiuron, diazinon diazinon), dichlorvos (dichlorvos), dichloromezotiaz (dicloromezotiaz), dicofol (dicofol), dienochlor (dienochlor), diflovidadin (diflovidazin), diflubenzuron (diflubenzuron), dimefluthrin (dimefluthrin), dimethoate (dimethoate), dimethylvinphos (dimethylvinphos), dipropylidaz (dimpropyridaz), dinotefuran (dinotefuran),Diofenolan, disulfoton, DNOC, d-T-80-phthalthrin, emamectin benzoate, empenthrin, endosulfan, EPN, epsilon-metofluthrin, epsilon-momfluorothrin, esfenvalerate, ethifencarb, ethiprole, etofenprox, etoxazole, etrimfos, Febantel, fenazaquin, fenbutatin oxide oxide), fenitrothion, fenmezoditiaz, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyroximate, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluacrylamide, Pyrim (fluacrypyrim), fluazuron (fluazuron), flubendiamide (flubendiamide), fluchlordiniliprole (fluchlorodiniliprole), flucycloxuron (flucycloxuron), flucythrinate (flucythrinate), flufenerim (flufenerim), flufenoxuron (flufenoxuron), flufenprox (flufenprox), flufiprole (flufiprole), fluhexafon (fluhexafon), flumethrin (flumethrin),Flupentiofenox, flupyradifurone, flupyrimin, flupyroxystrobin, fluralaner, fluvalinate, fluxametamide, fonophos, formetanate, formothion, furathiocarb b), gamma-cyhalothrin, halfenprox, halofenozide, heptafluthrin, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, imiprothrin, indazapyroxamet, indoxa indoxacarb, indoxacarb-MP, isocycloseram, isofenphos, isoflualanam, isoprocarb, isoxathion, kappa-bifenthrin, kappa-tefluthrin, lambda-cyhalothrin, ledpr ona (ledprona), lepimectin (lepimectin), lufenuron (lufenuron), malathion (malathion), meperfluthrin (meperfluthrin), metaflumizone (metaflumizone), metalcarb (metalcarb), metaldehyde (metaldehyde), methacrifos (methacrifos), methamidophos (methamidophos), methidathion (methidathion), methomyl (methomyl), methoprene (methoprene),Methoxychlor, methoxyfenozide, methyl bromide bromide), metofluthrin, milbemectin, momfluorothrin, monocrotophos, muscalure, nicofluprole, nitenpyram, novaluron, noviflumuron, omethoate, oxazosulfyl, oxydemeton-methyl, oxydeprofos, parathion, parathion-methyl, pentachlorophenol, permethrin, phenothrin, phenthoate, phorate, phosalone, phosmet To (phosmet), phosphamidon (phosphamidon), phoxim (phoxim), pioxaniliprole (pioxaniliprole), piperflanilide (piperflanilide), pirimicarb (pirimicarb), pirimiphos - methyl (pirimiphos-methyl), praziquantel (Praziquantel), profenofos (profenofos), profluthrin (profluthrin), propaphos (propaphos), propargite (propargite), prothiofos (prothiofos), protrifenbut (protrifenbute), piflubumide (pyflubumide), pymetrozine (pymetrozine), pyraclofos (pyraclofos), pyrafluprole (pyrafluprole), pyrethrins (pyrethrins), pyridaben (pyridaben), pyridalyl (pyridalyl), pyrifluquinazon (pyrifluquinazon),Pyrimidifen, pyriprole, pyriproxyfen, resmethrin, rotenone, silafluofen, spidoxamat, spinetoram, spinosad, spirobudifen, spirodiclofen, spiromesifen, Spiropidione (spiropidion), spirotetramate (spirotetramat), spiromesifen (spyromesifen), sulfiflumin (sulfiflumin), sulfotep (sulfotep), sulfoxaflor (sulfoxaflor), sulprofos (sulprofos), tau-fluvalinate (tau-fluvalinate), tebufenozide (tebfenozide), tebufenpyrad (tebufenpyrad), teflubenzuron (teflubenzuron), te Fluthorin (tefluthorin), terbufos (terbufos), tetrachlorantraniliprole (tetrachlorantraniliprole), tetrachlorvinphos (tetrachlorvinphos), tetramethrin (tetramethrin), tetramethylfluthrin (tetramethylfluthrin), tetraniliprole (tetraniliprole), thiacloprid (thiacloprid), thiamethoxam (thiamethoxam), thiocyclam (thiocyclam), thiodicarb (thiodicarb), thiofanox (thiofanox), thiometon (thiometon), thioantraniliprole (tiorantraniliprole), tolfenpyrad (tolfenpyrad), tralomethrin (tralomethrin), transfluthrin (transfluthrin), triazamate (triazamate), triazuron (triazuron), trichlorfon (trichlorfon), triflumezopyrim (triflumezopyrim),triflumuron, tyclopyrazoflor, vamidothion, and zeta-cypermethrin, etc.

[0249] Parasitic drugs: esfenvalerate, fenpropathrin, fenvalerate, alphacypermethrin, bifenthrin, cypermethrin, deltamethrin, etofenprox, lambda-cyhalothrin, permethrin, tefluthrin fluthrin), zeta-cypermethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiamethoxam, chromafenozide, fenoxycarb, lufenuron, methoprene, Pyriproxyfen, triflumuron, chlorpyrifos, chlorpyrifos-methyl, diazinon, dichlorvos, fenitrothion, fenthion, malathion, pirimiphos-methyl, tetrachlorvinphos , ethiprole, fipronil, propoxur, carbaryl, bendiocarb, metoxadiazone, fenocarb, carbofuran, afoxolaner, fluralaner, fluxametamide, sarolaner, lotilaner,Tigolaner, esafoxolaner, modoflaner, umifoxolaner, mivorilaner, avermectin, ivermectin, doramectin, eprinomectin, madeuramycin, milbemycin, milbemycin oxime oxime), moxidectin, selamectin, indoxacarb, amitraz, bistrifluron, spinosad, albendazole, atovaquone, bithionol, cambendazole, carnidazole, chloroquine, clazuril, clorsulon, closantel, coumaphos, dichlorophen, diethylcarbamazine, diminazene, dinitolmide, dithiazanine iodide iodide), emodepside, epsiprantel, febantel, fenbendazole, flubendazole, glycalpyramide, imidocarb, levamisole, mebendazole, mebendazole, mefloquine hydrochloride, melarsomine dihydrochloride,Metronidazole, methylidine, monepantel, morantel tartrate, niclosamide, oxantel pamoate, oxantel tartrate, oxibendazole, oxyclozanide, piperazine adipate, piperazine citrate, piperazine phosphate, praziquantel, pyrantel pamoate, rafoxanide, tetramisole hydrochloride, thiabendazole, and triclabendazole, etc.

[0250] Antifungal agents: ketoconazole and miconazole nitrate, etc.

[0251] Antibacterial agents: amoxicillin, ampicillin, bethoxazin, bithionol, bronopol, cefapirin, cefazolin, cefquinome, ceftiofur, chlortetracycline, clavulanic acid acid), danofloxacin, difloxacin, dinitolmide, enrofloxacin, florfenicol, lincomycin, lomefloxacin, marbofloxacin, miloxacin, mirosamycin, nitrapyrin, norfloxacin, octhilinone, ofloxacin, orbifloxacin, oxolinic acid acid), oxytetracycline, penicillin, streptomycin, thiamphenicol, tiamulin fumarate, tilmicosin phosphate, acetylisovaleryltylosin acetate, tylosin phosphate, tulathromycin, valnemulin, calcined shell calcium (calcium oxide), Talaromyces, Trichoderma, and Coniothyrium, etc.

[0252] The application amount of the compound of the present invention varies depending on the application site, application time, application method, cultivated crop, etc., but generally, an amount of the active ingredient is 0.005 to 50 kg per hectare (ha), and preferably 0.01 to 1 kg.

[0253] Next, formulation examples of formulations using the compounds of the present invention are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, "parts" means parts by weight.

[0254] [Wettable powder] Compound of the present invention 0.1-80 parts Solid carrier 5-98.9 parts Surfactant 1-10 parts Others 0-5 parts As the others, for example, an anti-caking agent or an anti-decomposition agent can be mentioned.

[0255] [Emulsifiable concentrate] Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts As the other, for example, a spreading agent or a decomposition inhibitor can be mentioned.

[0256] [Suspending agent] Compound of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts As the others, for example, an antifreeze agent or a thickener can be mentioned.

[0257] [Water Dispersible Granule] Compound of the present invention 0.1-90 parts Solid carrier 0-98.9 parts Surfactant 1-20 parts Others 0-10 parts As the others, for example, a binder or a decomposition inhibitor can be mentioned.

[0258] [Liquid Formulation] Compound of the present invention 0.01-70 parts Liquid carrier 20-99.99 parts Others 0-10 parts As the other ingredients, for example, an antifreeze agent or a spreading agent can be mentioned.

[0259] [Granules] Compound of the present invention 0.01-80 parts Solid carrier 10-99.99 parts Others 0-10 parts As the others, for example, a binder or a decomposition inhibitor can be mentioned.

[0260] [Dust] Compound of the present invention 0.01-30 parts Solid carrier 65-99.99 parts Others 0-5 parts As the other, for example, an anti-drift agent or anti-decomposition agent can be mentioned.

[0261] When used, the above formulation is diluted with water 1 to 10,000 times, preferably 100 to 10,000 times, or is sprayed without dilution.

[0262] Next, formulation examples of agricultural and horticultural fungicides containing the compound of the present invention as an active ingredient will be shown in more detail, but the formulations of the present invention, including the compound of the present invention, are not limited to these. In the following formulation examples, "parts" means parts by weight.

[0263] Formulation Example 1: Emulsifiable concentrate Compound No. 1-001 of the present invention 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Sorpol 2680 5 parts (a mixture of a nonionic surfactant and anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) The above ingredients are uniformly mixed to prepare an emulsifiable concentrate. When used, the emulsifiable concentrate is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient becomes 0.005 to 50 kg per hectare.

[0264] Formulation Example 2: Wettable Powder Compound No. 1-001 of the present invention 25 parts Pyrophyllite 66 parts Sorpol 5039 4 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Carplex #80D 3 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) Calcium lignosulfonate 2 parts The above ingredients are uniformly mixed and pulverized to prepare a wettable powder. When used, the wettable powder is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient becomes 0.005 to 50 kg per hectare.

[0265] Formulation Example 3: Dust Compound No. 1-001 of the present invention 3 parts Carplex #80D 0.5 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) Kaolinite 95 parts Diisopropyl phosphate 1.5 parts The above ingredients are uniformly mixed and pulverized to prepare a dust. When used, the dust is applied so that the amount of the active ingredient becomes 0.005 to 50 kg per hectare.

[0266] Formulation Example 4: Granules Compound No. 1-001 of the present invention 5 parts Bentonite 30 parts Talc 64 parts Calcium lignosulfonate 1 part The above ingredients are homogeneously mixed and pulverized, a small amount of water is added, the mixture is stirred and mixed, granulated in an extrusion granulator, and dried to give granules. When used, the granules are sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.

[0267] Formulation Example 5: Flowable Compound No. 1-001 of the present invention 25 parts Sorpol 3353 5 parts (nonionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Lunox 1000C 0.5 parts (anionic surfactant: trade name, manufactured by Toho Chemical Industry Co., Ltd.) Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts The above ingredients except for the active ingredient (compound of the present invention) are uniformly dissolved, and then the compound of the present invention is added and stirred well, followed by wet-pulverization in a sand mill to obtain a flowable formulation. When used, the flowable formulation is diluted 50 to 20,000 times with water and sprayed so that the amount of active ingredient is 0.005 to 50 kg per hectare.

[0268] Formulation Example 6: Dry flowable formulation Compound No. 1-001 of the present invention 75 parts Hitenol NE-15 5 parts (anionic surfactant: trade name, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) Vanilex N 10 parts (anionic surfactant: trade name, manufactured by Nippon Paper Industries Co., Ltd.) Carplex #80D 10 parts (white carbon: trade name, manufactured by Shionogi & Co., Ltd.) The above ingredients are uniformly mixed and finely pulverized, a small amount of water is added, the mixture is stirred and mixed, the mixture is granulated in an extrusion granulator, and the mixture is dried to prepare a dry flowable formulation. When used, the mixture is diluted 50 to 20,000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.

[0269] The compound of the present invention can be applied by foliage spray, soil treatment, seed disinfection, etc., but common methods commonly used by those skilled in the art are also effective.

[0270] [Summary] As described above, the present invention relates to the following [1] to

[108] .

[0271] [1] Formula (1):

[0272] [In formula (1), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula:

[0273] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy, R １ａｂ is a hydrogen atom, C １ ~C ６ Alkyl, halogen atom, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) alkyl; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula:

[0274] Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, Z ２ In the relationship, when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom or a halogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C１ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents an alkyl group, and Q represents an oxygen atom, a sulfur atom, or NOR ７ represents R ７ is a hydrogen atom or C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20, J-21, phenylcarbonyl, -CH ２ R ５ａ , -C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amino, —C(O)R ５ｄ , phenyl, (Z ５ｃ ) ｍ phenyl substituted by -C(=NOR ２ａ ) R ２ｂ , —C(O)NR ５ｃ R ５ｆ , C １ ~C ７ Alkyl or halo(C １ ~C ６ ) alkyl; J-1-a, J-2 to J-13, J-15 to J-18, J-20, and J-21 each represent a structure represented by the following structural formula:

[0275] Z５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) Alkyl, E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-13, E-15, E-19, E-22, E-25, E-26, E-27, E-28, E- 29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ５may be the same as or different from each other, and E-1 to E-9, E-13, E-15, E-19, E-22, E-25 to E-44, and E-45 each represent a structure represented by the following structural formula:

[0276] Z ６ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl; Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl, —CH ２ OH, C ３ ~C１０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ represents R ５ａｂ represents a hydrogen atom; ５ａ is (Z ５ａ ) ｍ１ Phenyl substituted by -NHC(O)OR ５ｆ represents R ５ｂ is (Z ５ｂ ) ｍ１ phenyl, phenyl, substituted by —C(O)R ５ｆ , C １ ~C ６ Alkoxycarbonyl, E-1, phenylcarbonyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C ３ ~C １０ ) cycloalkyl, E-1, E-3, E-5, E-7, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-24, (Z ５ｂ ) ｍ１ phenyl, phenyl, C １ ~C ６ Alkoxy, —OH, halo(C １ ~C ６ ) alkyl or —C(═NH)R ５ｅ E-10 to E-12, E-14, E-16 to E-18, E-20, E-21, E-23 and E-24 represent structures represented by the following structural formulas, respectively:

[0277] Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ａ is C １ ~C ６ Alkyl, E-14, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｄ represents L-1 or L-2, and L-1 and L-2 represent structures represented by the following structural formulas:

[0278] R ５ｅ is (Z ５ｄ ) ｍ１ represents phenyl substituted by R ５ｆ is C １ ~C ６ Alkyl or halo(C １ ~C ６ ) alkyl, R １０ is Halo (C １ ~C ６ ) represents an alkyl or halogen atom; R １１ is cyano, phenyl, (Z ５ｄ ) ｍ1 phenyl substituted by １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylthio, -OCOCH ３ , L-3, Di(C １ ~C ６ alkyl)amino, L-2, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, -NHCOCH ３ or C １ ~C ６L-3 represents a structure represented by the following structural formula:

[0279] Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃ may be the same as or different from each other, Z ５ｄ represents a halogen atom, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｄ may be the same or different, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, p4 represents an integer of 0, 1, 2, 3 or 4, and p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, or a salt thereof.

[0280] [2] R ５ are J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20, J-21, phenylcarbonyl, -CH２ R ５ａ , -C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amino, —C(O)R ５ｄ , phenyl, (Z ５ｃ ) ｍ phenyl substituted by -C(=NOR ２ａ ) R ２ｂ , —C(O)NR ５ｃ R ５ｆ , C １ ~C ７ Alkyl or halo(C １ ~C ６ p3 represents an integer of 0 or 1; p4 represents an integer of 0, 1 or 2; and p7 represents an integer of 0 or 1. The enamide compound or a salt thereof according to [1] above.

[0281] [3] R ２ represents G-2-a, and R ２ａｃ is a halogen atom or C １ ~C ６ represents alkyl, R ２ａｅ represents a hydrogen atom; Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl, halo (C １ ~C ６) Alkyl, E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-13, E-15, E-19, E-22, E-25, E-26, E-27, E-28, E- 29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ The enamide compound or salt thereof according to the above [2], which represents alkenyl.

[0282] [4] Q represents an oxygen atom, and R ５ is J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20 or -C(O)NHR ５ｃ The enamide compound or salt thereof according to [3] above, wherein

[0283] [5] R ５ represents J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-12, J-15 or J-20,

[0284] [6] R ５represents J-1-a, J-2, or J-10; p3 represents an integer of 0 or 1; p4 represents an integer of 0, 1, or 2; and p7 represents an integer of 0 or 1. The enamide compound or a salt thereof according to [1] above.

[0285] [7] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkylthio group; Q represents an oxygen atom; Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, E-1, E-2 or E-6; Z ６ is a halogen atom or C １ ~C ６ represents alkyl; Z ５ｃ is a halogen atom or C １ ~C ６ m represents an integer of 1 or 2; p1 represents an integer of 1; and p2 represents an integer of 0 or 1. The enamide compound or a salt thereof according to [6] above.

[0286] [8] R ２ represents G-2-a, and Z ５ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C １ ~C ６ ) alkyl, E-1, E-2 or E-6; R ５ａａ is C １ ~C ６ Alkyl, E-1, E-2, E-3, E-9, halo(C １ ~C６ ) alkyl, C ３ ~C １０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ The enamide compound or salt thereof according to [7] above, wherein

[0287] [9] Formula (1d):

[0288] [In formula (1d), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula:

[0289] R １ａａ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ａｂ represents a hydrogen atom; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula:

[0290] Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, and when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, phenylcarbonyl, —CH ２ R ５ａ , -C(O)NHNHR ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amine, —C(O)R ５ｄ , phenyl or —C(═NOR ２ａ ) R ２ｂ J-1-a, J-2 to J-9, and J-10 each represent a structure represented by the following structural formula:

[0291] Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １~C ６ ) alkyl, E-1, E-2a, E-3, E-4, E-5, E-6, E-7a, E-8, C ３ ~C ６ Cycloalkylmethyl, C １ ~C ６ Alkoxymethyl or R １０ C replaced by ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, and E-1, E-2a, E-3 to E-6, E-7a, and E-8 each represent a structure represented by the following structural formula:

[0292] Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2a, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl or —CH ２ represents OH, R ５ａｂ represents a hydrogen atom, E-9 represents a structure represented by the following structural formula:

[0293] Z ６is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl, R ５ａ is (Z ５ａ ) ｍ１ represents phenyl substituted by R ５ｂ is (Z ５ｂ ) ｍ１ represents phenyl substituted by R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C ６ cycloalkyl, E-1, E-3, E-5, E-10, E-11a, E-12b, E-13a, E-14a, E-15a or (Z ５ｂ ) ｍ１ E-10, E-11a, E-12b, E-13a, E-14a and E-15a each represent a structure represented by the following structural formula:

[0294] Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ｄ represents L-1, and L-1 represents a structure represented by the following structural formula:

[0295] R １０ is Halo (C １ ~C ６ ) alkyl; Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂis a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃ may be the same or different, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, and p4 represents an integer of 0, 1, 2, 3 or 4, or a salt thereof.

[0296]

[10] R １ａａ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ａｂ represents a hydrogen atom; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, and when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃrepresents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, phenylcarbonyl, —CH ２ R ５ａ , -C(O)NHNHR ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amine, —C(O)R ５ｄ , phenyl or —C(═NOR ２ａ ) R ２ｂ represents Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍphenyl substituted by ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, E-1, E-2a, E-3, E-4, E-5, E-6, E-7a, E-8, C ３ ~C ６ Cycloalkylmethyl, C １ ~C ６ Alkoxymethyl or R １０ C replaced by ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2a, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl or —CH ２ represents OH, R ５ａｂ represents a hydrogen atom; Z ６ is a halogen atom, C １ ~C ６ Alkyl, halo (C１ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl, R ５ａ is (Z ５ａ ) ｍ１ represents phenyl substituted by R ５ｂ is (Z ５ｂ ) ｍ１ represents phenyl substituted by R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C ６ cycloalkyl, E-1, E-3, E-5E-10, E-11a, E-12b, E-13a, E-14a, E-15a or (Z ５ｂ ) ｍ１ represents phenyl or phenyl substituted by ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ｄ represents L-1, and R １０ is Halo (C １ ~C ６ ) alkyl; Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂmay be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃ may be the same as or different from each other, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, and p4 represents an integer of 0, 1, 2, 3 or 4, an enamide compound or a salt thereof represented by [9] above.

[0297]

[11] R １ａａ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ａｂ represents a hydrogen atom; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, and when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, phenylcarbonyl, —CH ２ R ５ａ , -C(O)NHNHR ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amine, —C(O)R ５ｄ , phenyl or —C(═NOR ２ａ ) R ２ｂ represents Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, E-1, E-2a, E-3, E-4, E-5, E-6, E-7a, E-8, C ３ ~C ６ Cycloalkylmethyl, C １ ~C６ Alkoxymethyl or R １０ C replaced by ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2a, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl or —CH ２ represents OH, R ５ａｂ represents a hydrogen atom; Z ６ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl, R ５ａ is (Z ５ａ ) ｍ１represents phenyl substituted by R ５ｂ is (Z ５ｂ ) ｍ１ represents phenyl substituted by R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C ６ cycloalkyl, E-1, E-3, E-5E-10, E-11a, E-12b, E-13a, E-14a, E-15a or (Z ５ｂ ) ｍ１ represents phenyl or phenyl substituted by ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ｄ represents L-1, and R １０ is Halo (C １ ~C ６ ) alkyl; Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃmay be the same as or different from each other, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, and p4 represents an integer of 0, 1, 2, 3 or 4. The enamide compound or salt thereof according to [9] above.

[0298]

[12] R １ａａ is a hydrogen atom, a halogen atom or C １ ~C ６ represents alkyl, R １ａｂ represents a hydrogen atom; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3 or G-4, and Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl or -C(=NOR ２ａ ) R ２ｂ represents R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, phenylcarbonyl, —CH ２ R ５ａ, -C(O)NHNHR ５ｂ or -C(O)NHR ５ｃ represents Z ５ is C １ ~C ６ represents alkyl; Z ５ In the above relationship, when p2 represents an integer of 2 and p4 represents an integer of 2, 3 or 4, each Z ５ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted with E-1 or E-2a, ５ａｂ represents a hydrogen atom; Z ６ represents a halogen atom; Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same or different from each other, R ５ａ is (Z ５ａ ) ｍ１ represents phenyl substituted with R ５ｂ is (Z ５ｂ ) ｍ１ represents phenyl substituted with R ５ｃ is C １ ~C ６ Alkyl, E-1 or (Z ５ｂ ) ｍ１ represents phenyl substituted with ５ａ is C １ ~C ６ When m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ represents a halogen atom, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z５ｃ may be the same or different from each other, m and m1 represent an integer of 1 or 2, p2 represents an integer of 0, 1 or 2, and p4 represents an integer of 0, 1, 2, 3 or 4, an enamide compound or a salt thereof represented by the above [9].

[0299]

[13] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy; or a salt thereof.

[0300]

[14] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[12] , which represents alkylthio.

[0301]

[15] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６Alkoxy or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[12] , which represents alkylthio.

[0302]

[16] R １ａａ is a hydrogen atom, a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[12] above, wherein R represents alkyl.

[0303]

[17] R １ａａ is C １ ~C ６ Alkoxy or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[12] , which represents alkylthio.

[0304]

[18] R １ａａ represents a hydrogen atom, or a salt thereof.

[0305]

[19] R １ａａ is a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[12] above, wherein R represents alkyl.

[0306]

[20] R １ａａ is C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[12] above, wherein R represents alkyl.

[0307]

[21] R １ａａ is C １ ~C ６ Alkoxy or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[12] , which represents alkylthio.

[0308]

[22] R １ａｂ is a hydrogen atom, C １ ~C ６The enamide compound or salt thereof according to any one of [1] to

[21] above, wherein R represents an alkyl or halogen atom.

[0309]

[23] R １ａｂ represents a hydrogen atom, or a salt thereof.

[0310]

[24] R １ａｂ is C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[21] above, wherein R represents alkyl.

[0311]

[25] R １ａｂ represents a halogen atom, or a salt thereof.

[0312]

[26] Z １ａ is C １ ~C ４ The enamide compound or salt thereof according to any one of the above [1] to

[25] , wherein R represents alkyl.

[0313]

[27] Z １ａ is C １ The enamide compound or salt thereof according to any one of the above [1] to

[25] , wherein R represents alkyl.

[0314]

[28] R ２ represents G-1-a, or a salt thereof according to any one of [1] to

[27] above.

[0315]

[29] R ２ represents G-2-a, or a salt thereof according to any one of [1] to

[27] above.

[0316]

[30] R ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, cyano or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkoxy.

[0317]

[31] R ２ａｃis a hydrogen atom, a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkyl.

[0318]

[32] R ２ａｃ is a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkyl.

[0319]

[33] R ２ａｃ represents a halogen atom, or a salt thereof.

[0320]

[34] R ２ａｃ is C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkyl.

[0321]

[35] R ２ａｃ is Halo (C １ ~C ６ ) alkyl or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkoxy.

[0322]

[36] R ２ａｃ is Halo (C １ ~C ６ ) alkyl; or a salt thereof according to any one of [1] to

[27] and

[29] above.

[0323]

[37] R ２ａｃ is C １ ~C ６ Alkoxy or C １ ~C ６ The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , which represents alkoxycarbonyl.

[0324]

[38] R ２ａｃ is C １ ~C ６The enamide compound or salt thereof according to any one of the above [1] to

[27] and

[29] , wherein R represents alkoxy.

[0325]

[39] R ２ａｅ represents a hydrogen atom, or a salt thereof.

[0326]

[40] R ２ａｅ represents a halogen atom, or a salt thereof.

[0327]

[41] R ２ represents G-3, G-4 or G-5, or a salt thereof according to any one of [1] to

[27] above.

[0328]

[42] R ２ represents G-5, or a salt thereof according to any one of [1] to

[27] above.

[0329]

[43] The enamide compound or a salt thereof according to any one of [1] to

[42] above, wherein Q represents an oxygen atom.

[0330]

[44] The enamide compound or salt thereof according to any one of [1] to

[42] above, wherein Q represents a sulfur atom.

[0331]

[45] Q is NOR ７ The enamide compound or salt thereof according to any one of [1] to

[42] above, wherein

[0332]

[46] R ５ is J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, J-11, J-12, J-17, J-18, J-20 or -C(O)NHR ５ｃ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0333]

[47] R ５ are J-3, J-4, J-5, J-6, J-7, J-8, J-9, phenylcarbonyl, -CH ２ R ５ａ, -C(O)NHNHR ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amine, —C(O)R ５ｄ , phenyl or —C(═NOR ２ａ ) R ２ｂ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0334]

[48] ​​R ５ is J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-11, J-12, J-17, J-18, J-20 or -C(O)NHR ５ｃ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0335]

[49] R ５ is phenylcarbonyl, -CH ２ R ５ａ , -C(O)NHNHR ５ｂ or -C(O)NHR ５ｃ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0336]

[50] R ５ is phenyl, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-12, J-15, J-20 or —C(O)NHR ５ｃ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0337]

[51] R ５ represents J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-12, J-15, or J-20, or a salt thereof.

[0338]

[52] R ５ represents J-3, J-4, J-5, J-6, J-7, J-8 or J-9, or a salt thereof according to any one of [1] to

[45] above.

[0339]

[53] R ５ represents J-1-a, J-3, J-4, J-5 or J-12, or a salt thereof according to any one of [1] to

[45] above.

[0340]

[54] R ５ represents J-3, J-4 or J-5, or a salt thereof according to any one of [1] to

[45] above.

[0341]

[55] R ５ represents J-12, J-15, or J-20, or a salt thereof according to any one of [1] to

[45] above.

[0342]

[56] R ５ represents J-7, J-8, J-9, J-15 or J-20, or a salt thereof according to any one of [1] to

[45] above.

[0343]

[57] R ５ represents J-7, J-8 or J-9, or a salt thereof according to any one of [1] to

[45] above.

[0344]

[58] R ５ represents J-9, J-15, or J-20, or a salt thereof according to any one of [1] to

[45] above.

[0345]

[59] R ５ is phenylcarbonyl, —C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ or -C(O)R５ｄ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0346]

[60] R ５ is phenylcarbonyl, —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ or -C(O)SR ５ｂ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0347]

[61] R ５ is -C(O)CH=CHR ５ｂ or -C(O)R ５ｄ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0348]

[62] R ５ is -C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl or —C(O)OR ５ｂ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0349]

[63] R ５ is -C(O)NHR ５ｃ or -C(O)R ５ｄ The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein

[0350]

[64] R ５ is -NHR ５ｂ Or Ji (C １ ~C ６

[46] The enamide compound or salt thereof according to any one of [1] to

[45] above, wherein R represents (alkyl)amino.

[0351]

[65] R ５ is phenyl or (Z ５ｃ ) ｍ

[0039] The enamide compound or a salt thereof according to any one of [1] to

[45] above, wherein R represents a phenyl substituted by

[0352]

[66] R ５ represents J-1-a, J-2, or J-10, or a salt thereof according to any one of [1] to

[45] above.

[0353]

[67] R ５ represents J-1-a, the enamide compound represented by

[66] above or a salt thereof.

[0354]

[68] R ５ａａ is C １ ~C ６ Alkyl, E-1, E-2, E-2a, E-3, E-9, halo(C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ The enamide compound or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] above,

[0355]

[69] R ５ａａ is C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl, E-1, E-2, E-2a, E-3, E-9 or halo(C １ ~C ６ ) represents alkyl, or a salt thereof.

[0356]

[70] R ５ａａ is phenyl, (Z ５ｃ ) ｍ

[0039] The enamide compound or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] , wherein E-1, E-2, E-2a or E-3 represents phenyl substituted by

[0357]

[71] R ５ａａ is C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl or C ３ ~C １０The enamide compound or salt thereof according to any one of the above [1] to

[45] and

[66] to

[67] , which represents cycloalkyl.

[0358]

[72] R ５ａａ is E-1, E-2, E-2a, E-3, E-9 or -C(=NOR ２ａ ) R ２ｂ The enamide compound or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] above,

[0359]

[73] R ５ａａ represents E-1, E-2, E-2a, E-3 or E-9, or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] above.

[0360]

[74] R ５ represents J-2, or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] above.

[0361]

[75] R ５ represents J-10, or a salt thereof according to any one of [1] to

[45] and

[66] to

[67] above.

[0362]

[76] R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C ３ ~C １０ ) Cycloalkyl, E-1, E-3, E-5, E-7, E-10, E-11, E-11a, E-12, E-12b, E-13, E-13a, E-1 4, E-14a, E-15, E-15a, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-24, (Z ５ｂ ) ｍ１ phenyl or halo(C １ ~C ６ ) alkyl. The enamide compound or salt thereof according to any one of [1] to

[65] above.

[0363]

[77] R ５ｃ is C １~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C ３ ~C １０ ) cycloalkyl or halo(C １ ~C ６ ) alkyl. The enamide compound or salt thereof according to any one of [1] to

[65] above.

[0364]

[78] R ５ｃ represents E-3, E-5, E-7, E-10, E-11, E-11a, E-12, E-12b, E-13, E-13a, E-14, E-14a, E-15, E-15a, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, or E-24, the enamide compound or salt thereof according to any one of [1] to

[65] above.

[0365]

[79] R ５ｃ represents E-1, E-10, E-14, E-14a, E-15 or E-15a, or a salt thereof according to any one of [1] to

[65] above.

[0366]

[80] R ５ｃ is (Z ５ｂ ) ｍ１

[0023] The enamide compound or salt thereof according to any one of [1] to

[65] above, wherein R represents a phenyl substituted by

[0367]

[81] Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl, halo (C １ ~C ６ ) Alkyl, E-1, E-2, E-2a, E-3, E-4, E-5, E-6, E-7, E-7a, E-8, E-9, E-13, E-13a, E-15, E-15a, E-19, E-22, E-25, E-26, E -27, E-28, E-29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[80] above, wherein R represents alkenyl.

[0368]

[82] Z ５ is C １ ~C ６ Alkyl, halogen atom, halo(C １ ~C ６ ) alkyl, E-1, E-15, E-15a, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ alkenyl or R １１ C replaced by １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[80] above, wherein R represents alkyl.

[0369]

[83] Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) represents alkyl, or a salt thereof.

[0370]

[84] Z ５ represents a halogen atom, halo(C １ ~C ６ ) alkyl, E-1, E-15 or E-15a.

[0371]

[85] Z ５ is C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[80] above, wherein R represents alkoxy.

[0372]

[86] Z ５ is C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[80] above, which represents alkoxyethyl.

[0373]

[87] Z ５ is R １０ C replaced by ２ ~C ６ Alkenyl, R １１ C replaced by １ ~C ６ Alkyl or C ２~C ６ The enamide compound or salt thereof according to any one of [1] to

[80] above, wherein R represents alkenyl.

[0374]

[88] Z ５ｂ is a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[87] above, wherein R represents alkyl.

[0375]

[89] Z ５ｃ is C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[88] above, wherein R represents an alkyl or halogen atom.

[0376]

[90] Z ６ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[89] above, wherein the enamide compound or salt thereof represents alkoxy or cyano.

[0377]

[91] Z ６ is a halogen atom or C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[89] above, wherein R represents alkyl.

[0378]

[92] Z ６ is C １ ~C ６ The enamide compound or salt thereof according to any one of [1] to

[89] above, wherein the enamide compound or salt thereof represents alkoxy or cyano.

[0379]

[93] R １０ represents a halogen atom, or a salt thereof.

[0380]

[94] R １１ is C １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylthio or -OCOCH ３The enamide compound or salt thereof according to any one of [1] to

[93] above, wherein

[0381]

[95] R １１ L-3 or di(C １ ~C ６

[94] The enamide compound or salt thereof according to any one of [1] to

[93] above, wherein R represents (alkyl)amino.

[0382]

[96] The enamide compound or a salt thereof according to any one of the above [1] to

[95] , wherein p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1 or 2, p4 represents an integer of 0, 1 or 2, and p7 represents an integer of 0, 1 or 2.

[0383]

[97] The enamide compound or salt thereof according to any one of [1] to

[96] above, wherein p1 represents an integer of 1.

[0384]

[98] The enamide compound or salt thereof according to any one of [1] to

[97] above, wherein p2 represents an integer of 0 or 1.

[0385]

[99] The enamide compound or salt thereof according to any one of the above [1] to

[98] , wherein p3 represents an integer of 0 or 1, p4 represents an integer of 0, 1 or 2, and p7 represents an integer of 0, 1 or 2.

[0386]

[100] The enamide compound or salt thereof according to any one of the above [1] to

[99] , wherein p3 represents an integer of 1, p4 represents an integer of 1 or 2, and p7 represents an integer of 0 or 1.

[0387]

[101] Formula (1-1a):

[0388] [In formula (1-1a), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula:

[0389] R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy, R １ａｂ is a hydrogen atom, C １ ~C ６ Alkyl, halogen atom, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) alkyl; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula:

[0390] Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, Z ２ In the relationship, when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom or a halogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ p2 represents an integer of 0 or 1, and p3 represents an integer of 0 or 1.

[0391]

[102] R ２ represents G-2-a or G-5,

[0392]

[103] R １ａａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, di(C １ ~C ６ alkyl)amino or halo(C １ ~C ６ ) represents alkoxy, R ２ represents G-2-a, and R ２ａｃ is a halogen atom or C １ ~C ６ represents alkyl, R ２ａｅ represents a hydrogen atom.

[0393]

[104] A pesticide containing, as an active ingredient, one or more selected from the enamide compounds and salts thereof according to any one of [1] to

[100] above.

[0394]

[105] A fungicide containing, as an active ingredient, one or more selected from the enamide compounds and salts thereof according to any one of [1] to

[100] above.

[0395]

[106] An agricultural and horticultural fungicide containing, as an active ingredient, one or more selected from the enamide compounds and salts thereof according to any one of [1] to

[100] above.

[0396]

[107] An antifungal agent containing, as an active ingredient, one or more selected from the enamide compounds and salts thereof according to any one of [1] to

[100] above.

[0397]

[108] An internal parasite control agent containing, as an active ingredient, one or more selected from the enamide compounds and salts thereof according to any one of [1] to

[100] above.

[0398] The present invention will be explained in more detail below by describing examples of synthesis and testing of the compounds of the present invention, but the present invention is not limited thereto.

[0399] For the medium pressure preparative liquid chromatography described in the synthesis examples, a medium pressure preparative apparatus manufactured by Yamazen Corporation; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column) was used.

[0400] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter, １ The chemical shift values ​​of H-NMR are expressed as Me as a standard substance. ４ Using Si (tetramethylsilane), measurements were made at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL) or 400 MHz (model: JNM-ECZ400S, manufactured by JEOL). １ The symbols in the H-NMR chemical shift values ​​have the following meanings: s: singlet, d: doublet, t: triplet, m: multiplet, br: broad singlet.

[0401] Synthesis Examples Synthesis Example 1 Synthesis of (Z)—N-(2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (Compound No. 1-001) 3 ml of methylene chloride was added to 80 mg of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)ethen-1-amine, and 80 mg of 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid, 478 mg of a 50% by mass solution of propylphosphonic anhydride in N,N-dimethylformamide, and 114 mg of triethylamine were added at room temperature, followed by stirring at room temperature for 12 hours. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (10 ml × 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate [gradient from 9:1 to 1:9 (volume ratio, the same applies hereinafter)] as an eluent to obtain 17 mg of the target product as a white solid. Melting point: 214-216°C.

[0402] Synthesis example 2: N １ -(2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)vinyl)-N ２ Synthesis of 4-(2,4-difluorophenyl)isoxazole-3-oxalamide (Compound No. 4-004)

[0403] To 2 ml of a methylene chloride solution (0.15 mol / l) of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)ethen-1-amine was added 2 ml of methylene chloride, and 30 mg of 2-((2,4-difluorophenyl)amino)-2-oxoacetic acid, 121 mg of triethylamine, and 191 mg of a 50% by mass solution of propylphosphonic anhydride in N,N-dimethylformamide were added at room temperature, followed by stirring at room temperature for 12 hours. After completion of the reaction, 3 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with chloroform (3 ml × 1). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, to obtain 15 mg of the target product as a white solid. Melting point: 169-171°C.

[0404] Synthesis Example 3: Synthesis of (Z)—N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (Compound No. 2-001) 3 ml of methylene chloride was added to 74 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine, and 101 mg of 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid, 382 mg of a 50% by mass solution of propylphosphonic anhydride in N,N-dimethylformamide, and 121 mg of triethylamine were added at room temperature, followed by stirring at room temperature for 12 hours. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with chloroform (5 ml × 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 76 mg of the target product as a white solid. Melting point: 214-216°C.

[0405] Synthesis Example 4: Synthesis of (Z)—N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-3-(3,5-difluoropyridin-2-yl)-1,2,4-oxadiazole-5-carboxamide (Compound No. 6-053) To 1000 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine, 40 ml of tetrahydrofuran was added, and 1458 mg of methyl 3-(3,5-difluoropyridin-2-yl)-1,2,4-oxadiazole-5-carboxylate was added, followed by cooling to −78° C. A mixed solution of 902 mg of potassium tert-butoxide and 10 ml of tetrahydrofuran was added dropwise thereto, and the mixture was stirred at -78°C for 5 minutes, and then at room temperature for a further 20 minutes. After completion of the reaction, 40 ml of saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (50 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 10 ml of diisopropyl ether, yielding 300 mg of the target product as a yellow solid. Melting point: 222-224°C.

[0406] Synthesis example 5: N １ -(4-bromo-2-fluorophenyl)-N ２Synthesis of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)oxalamide (Compound No. 5-056) To 75 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine, 5 ml of methylene chloride was added, and 171 mg of 4-bromo-2-fluoroaniline and 61 mg of triethylamine were added at room temperature, followed by cooling to 0°C. 75 mg of oxalyl chloride was added dropwise thereto, and the mixture was stirred at 0°C for 1 minute and then at room temperature for a further 30 minutes. After completion of the reaction, 10 ml of saturated aqueous sodium hydrogen carbonate solution was added dropwise to the reaction mixture at room temperature, followed by extraction with chloroform (10 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to give 11 mg of the desired product as a white solid, melting point 201-203°C.

[0407] Synthesis Example 6: Synthesis of 2,4-difluorophenyl(Z)-2-((2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)amino)-2-oxoacetate (Compound No. 5-031) To 74 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine, 3 ml of methylene chloride was added, and 78 mg of 2,4-difluorophenol and 122 mg of triethylamine were added at room temperature, followed by cooling to 0°C. To this was added dropwise 76 mg of oxalyl chloride, and the mixture was stirred at 0°C for 1 minute and then at room temperature for a further 60 minutes. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with chloroform (10 ml x 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 33 mg of the target product as a yellow solid. Melting point: 177-179°C.

[0408] Synthesis Example 7: Synthesis of S-(2,4-difluorophenyl)(Z)-2-((2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)amino)-2-oxoethanethioate (Compound No. 5-005) 3 ml of methylene chloride was added to 74 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine, and 131 mg of 2,4-difluorobenzenethiol and 182 mg of triethylamine were added at room temperature, followed by cooling to 0°C. 75 mg of oxalyl chloride was added dropwise thereto, and the mixture was stirred at 0°C for 1 minute and then at room temperature for a further 60 minutes. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with chloroform (10 ml × 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 33 mg of the target product as a yellow solid. Melting point: 202-204°C.

[0409] Synthesis Example 8: Synthesis of (Z)—N-(2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (Compound No. 1-001) Under a nitrogen atmosphere, 3 ml of 1,4-dioxane was added to 52 mg of N-(2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide, and 51 mg of 2-chloro-6-iodopyridine, 44 mg of potassium carbonate, and 17 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (divalent) were added at room temperature, and the mixture was heated to 100°C and stirred for 3 hours. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (10 ml x 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to give 12 mg of the desired product as a yellow solid, melting point 214-216°C.

[0410] Synthesis Example 9: Synthesis of tert-butyl (Z)-2-(2-((2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)amino)-2-oxoacetyl)hydrazine-1-carboxylate (Compound No. 5-132)

[0411] To 10 ml of methylene chloride, 610 mg of oxalyl chloride was added, and 10 ml of a methylene chloride solution (4.0 mol / L) of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine was added at room temperature. 10 ml of a methylene chloride solution (6.0 mol / L) of tert-butylhydrazine carboxylate was added at room temperature, and the mixture was stirred at room temperature for 60 minutes. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure, 10 ml of water was added dropwise at room temperature, and the mixture was extracted with methylene chloride (10 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent. The solvent was distilled off under reduced pressure, and 10 ml of diisopropyl ether was added to the resulting oil, and the precipitated solid was collected by filtration. The resulting solid was washed with 25 ml of methylene chloride, and the resulting filtrate was dried under reduced pressure to obtain 160 mg of the target product as a pale yellow solid, melting point 216-218°C.

[0412] Synthesis Example 10: Synthesis of (Z)-N-(2-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)vinyl)-5-propylisoxazole-3-carboxamide (Compound No. 6-103) 10 ml of methylene chloride was added to 150 mg of 5-propylisoxazole-3-carboxylic acid, and the mixture was cooled to 0°C. 254 mg of oxalyl chloride and 2 drops of N,N-dimethylformamide were added thereto, and the mixture was stirred at 0°C for 1 minute and then at room temperature for 60 minutes. The solvent was distilled off from the obtained filtrate under reduced pressure, and then 3 ml of methylene chloride was added thereto to prepare a methylene chloride solution of 5-propylisoxazole-3-carbonyl chloride. To 150 mg of 2-(5-bromo-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)ethen-1-amine were added 3 ml of methylene chloride and 568 mg of triethylamine, and a methylene chloride solution of 5-propylisoxazole-3-carbonyl chloride was added at room temperature and stirred for 16 hours. After completion of the reaction, 10 ml of water was added dropwise at room temperature, and the mixture was extracted with chloroform (10 ml x 2). The resulting organic layer was purified by silica gel column chromatography using ethyl acetate as an eluent. The solvent was distilled off under reduced pressure, and the precipitated solid was collected by filtration. The resulting solid was washed with 3 ml of acetone and dried under reduced pressure to obtain 46 mg of the target product as a pale yellow solid. Melting point: 151-153°C.

[0413] Synthesis Example 11: Synthesis of (Z)—N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide (Compound No. 2-001) To 30 mg of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-hydroxyethyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide, 2 ml of toluene was added, and 8.3 mg of thionyl chloride was added, followed by heating to 90° C. and stirring for 2 hours. After completion of the reaction, the solvent was distilled off from the reaction solution under reduced pressure, and the resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 10 mg of the target product as a pale yellow solid. Melting point: 214-216°C.

[0414] Synthesis Example 12: Synthesis of (Z)-N-(2-(6-chloropyridin-2-yl)-2-(1-methyl-1H-pyrazol-4-yl)vinyl)-5-methylisoxazole-3-carboxamide (Compound No. 3-009) To 100 mg of (E)-N-(2-(6-chloropyridin-2-yl)-2-iodovinyl)-5-methylisoxazole-3-carboxamide were added 62 mg of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxoboran-2-yl)-1H-pyrazole, 83 mg of sodium carbonate, and 33 mg of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (divalent), and then 3 mL of 1,4-dioxane and 2 drops of water were added under a nitrogen atmosphere, followed by stirring at 80° C. for 4 hours. After the reaction was completed, 5 ml of water was added dropwise at room temperature, and the mixture was extracted with chloroform (5 ml x 2). The obtained organic layer was purified by silica gel column chromatography using ethyl acetate as an eluent to obtain 15 mg of the target product as a pale yellow oily substance. 1 H-NMR (CDCl3, Me4Si, 300MHz): δ 13.00-12.72 (m, 1H), 8.15-6.32 (m, 7H), 3.88 (s, 3H), 3.49 (s, 3H).

[0415] Synthesis Example 13: Synthesis of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-3-(3,5-difluoropyridin-2-yl)-1,2,4-oxadiazole-5-carbothioamide (Compound No. 10-001) To 400 mg of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-3-(3,5-difluoropyridin-2-yl)-1,2,4-oxadiazole-5-carbothioamide was added 16 ml of toluene, and then 320 mg of Lawesson's reagent and 160 mg of sodium carbonate were added, followed by stirring at 120° C. for 1 hour. After completion of the reaction, 10 ml of a 5% by mass aqueous sodium carbonate solution was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (20 ml × 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 5 ml of diisopropyl ether to obtain 300 mg of the target product as a yellow solid. Melting point: 234-236°C.

[0416] Synthesis Example 14: Synthesis of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-3-(3,5-difluoropyridin-2-yl)-N'-methoxy-1,2,4-oxadiazole-5-carboximidamide (Compound No. 10-002) To 50 mg of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-3-(3,5-difluoropyridin-2-yl)-1,2,4-oxadiazole-5-carbothioamide were added 5 ml of ethanol and 2 ml of N,N-dimethylformamide, and then 20 mg of sodium acetate and 1 ml of triethylamine were added, followed by stirring at 80°C for 1 hour. After completion of the reaction, 10 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (10 ml x 3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 12 mg of the target product as a yellow solid. Melting point: 204-206°C.

[0417] Reference Examples The following are reference examples of methods for producing intermediates for the compounds of the present invention.

[0418] Reference Example 1: Synthesis of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)ethen-1-amine Reference Example 1, Step 1: Synthesis of (5-chloro-1-methyl-1H-pyrazol-4-yl)(6-chloropyridin-2-yl)methanol To a mixed solution of 717 mg of 2-chloro-6-iodopyridine and 15 mL of tetrahydrofuran, 3.5 mL of a tetrahydrofuran solution of isopropylmagnesium chloride lithium chloride complex (1.3 mol / L) was added at 0°C and stirred for 30 minutes. Thereafter, a mixed solution of 288 mg of 5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde and 5 mL of tetrahydrofuran was added dropwise at 0°C and stirred at room temperature for 12 hours. After completion of the reaction, 10 mL of 3 mol / L hydrochloric acid and 10 mL of water were added dropwise to the reaction mixture at room temperature, followed by extraction with ethyl acetate (10 mL x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 150 mg of a yellow oil, which was used in the next step without further purification. 1 H-NMR (CDCl3, Me4Si, 300MHz):δ 7.68-7.59 (m, 1H), 7.37 (s, 1H), 7.29-7.23 (m, 1H), 7.17-7.11 (m, 1H), 5.76-5.70 (m, 1H), 4.25-4.19 (m, 1H), 3.83 (s, 3H).

[0419] Reference Example 1, Step 2: Synthesis of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)acetonitrile To a mixed solution of 150 mg of (5-chloro-1-methyl-1H-pyrazol-4-yl)(6-chloropyridin-2-yl)methanol obtained in Reference Example 1, Step 1, and 10 ml of methylene chloride, 8.5 mg of lithium carbonate, 258 mg of trimethylsilyl cyanide, and 132 mg of iodine were added at room temperature, and the mixture was stirred at 35°C for 6 hours. After completion of the reaction, 10 ml of a 10% by mass aqueous sodium thiosulfate solution was added, and the mixture was extracted with chloroform (10 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent, and 86 mg of the target product was obtained as a yellow resin. 1 H-NMR (CDCl3, Me4Si, 300MHz): δ 7.75-7.64 (m, 1H), 7.54 (s, 1H), 7.41-7.25 (m, 2H), 5.17 (s, 1H), 3.85 (s, 3H).

[0420] Reference Example 1, Step 3: Synthesis of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)ethen-1-amine To a mixed solution of 100 mg of 2-(5-chloro-1-methyl-1H-pyrazol-4-yl)-2-(6-chloropyridin-2-yl)acetonitrile obtained in Reference Example 1, Step 2, and 3 mL of tetrahydrofuran, 42 mg of triethylamine was added at room temperature. The mixture was then cooled to 0°C, and 0.86 mL of a hexane solution of diisobutylaluminum hydride (1.0 mol / L) was added, followed by stirring at the same temperature for 2 hours. After completion of the reaction, 10 mL of water was added, and the mixture was extracted with chloroform (10 mL x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 80 mg of a yellow oily substance. 1 H-NMR (CDCl3, Me4Si, 400MHz): δ 8.10-6.20 (m, 7H), 3.95-3.80 (m, 3H).

[0421] Reference Example 2: Synthesis of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine Reference Example 2, Step 1: Synthesis of (6-chloropyridin-2-yl)(1,5-dimethyl-1H-pyrazol-4-yl)methanol To a mixed solution of 12.95 g of 2-chloro-6-iodopyridine and 300 ml of tetrahydrofuran, 45.4 ml of a tetrahydrofuran solution (1.3 mol / l) of isopropylmagnesium chloride lithium chloride complex was added at 0°C and stirred for 10 minutes. Thereafter, 6.10 g of 1,5-dimethyl-1H-pyrazole-4-carbaldehyde was added dropwise at 0°C and stirred at room temperature for 30 minutes. After completion of the reaction, 100 ml of saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (150 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 9.66 g of white crystals, which were used in the next step without further purification. 1 H-NMR (CDCl3, Me4Si, 400MHz):δ 7.80-7.56 (m, 1H), 7.45-7.05 (m, 3H), 5.80-5.65 (m, 1H), 4.18-4.01 (m, 1H), 3.79 (s, 3H), 2.25 (s, 3H).

[0422] Reference Example 2, Step 2: Synthesis of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)acetonitrile To a mixed solution of 9.66 g of (6-chloropyridin-2-yl)(1,5-dimethyl-1H-pyrazol-4-yl)methanol obtained in Reference Example 2, Step 1, and 480 ml of methylene chloride, 1.02 g of lithium carbonate, 25.2 ml of trimethylsilyl cyanide, and 10.1 g of iodine were added at room temperature, and the mixture was stirred at 35°C for 3 hours. After completion of the reaction, 300 ml of a 10% by mass aqueous sodium thiosulfate solution was added, and the mixture was extracted with chloroform (200 ml x 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 1:1 to 1:9) as an eluent to obtain 7.0 g of the desired product as a yellow resin. 1 H-NMR (CDCl3, Me4Si, 400MHz): δ 7.83-7.60 (m, 1H), 7.45-7.20 (m, 3H), 5.14 (s, 1H), 3.76 (s, 3H), 2.30 (s, 3H).

[0423] Reference Example 2, Step 3: Synthesis of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)ethen-1-amine To a mixed solution of 400 mg of 2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)acetonitrile obtained in Reference Example 2, Step 2, and 10 mL of tetrahydrofuran, 146 mg of triethylamine was added at room temperature. The mixture was then cooled to 0°C, and 4.86 mL of a toluene solution of diisobutylaluminum hydride (1.0 mol / L) was added, followed by stirring at the same temperature for 1 hour. After completion of the reaction, 10 mL of a 10% by mass aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate (30 mL x 3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure to obtain 400 mg of a yellow oily substance. 1H-NMR (CDCl3, Me4Si, 400MHz): δ 8.00-6.20 (m, 7H), 4.00-3.70 (m, 3H), 2.20-2.00 (m, 3H).

[0424] Reference Example 3: Synthesis of N-(2-bromo-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide Reference Example 3, Step 1: Synthesis of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-oxoethyl)isoxazole-3-carboxamide To 1.0 g of 2-amino-1-(1,5-dimethyl-1H-pyrazol-4-yl)ethan-1-one hydrochloride was added 30 ml of methylene chloride, and then 1.2 g of 5-(2,4-difluorophenyl)isoxazole-3-carboxylic acid, 4.2 g of a 50% by mass solution of propylphosphonic anhydride in N,N-dimethylformamide, and 1.8 g of triethylamine were added at room temperature, followed by stirring at room temperature for 12 hours. After the reaction was completed, 50 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with 50 ml of methylene chloride. The resulting organic layer was washed with 30 ml of saturated aqueous sodium bicarbonate solution, and then washed with saturated saline (30 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 10 ml of diisopropyl ether, yielding 1.0 g of the target product as a yellow solid. Melting point: 197-199°C.

[0425] Reference Example 3, Step 2: Synthesis of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-hydroxyethyl)isoxazole-3-carboxamide To 1.85 g of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-oxoethyl)isoxazole-3-carboxamide were added 40 ml of tetrahydrofuran and 4 ml of water, and 0.19 g of sodium tetrahydroborate was added at room temperature, followed by stirring at room temperature for 12 hours. After completion of the reaction, 100 ml of water was added dropwise to the reaction mixture at room temperature. The precipitated solid was collected by filtration, 50 ml of toluene was added to the resulting solid, and the solvent was distilled off under reduced pressure to obtain 1.70 g of the target product as a yellow solid. Melting point: 201-203°C.

[0426] Reference Example 3, Step 3: Synthesis of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)isoxazole-3-carboxamide To 16.7 g of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-hydroxyethyl)isoxazole-3-carboxamide, 500 ml of toluene was added, and 6.0 g of thionyl chloride was added at room temperature, followed by stirring at 110°C for 3 hours. After completion of the reaction, the reaction mixture was cooled to 0°C, and the precipitated solid was collected by filtration. To the obtained solid, 100 ml of toluene was added, and the solvent was distilled off under reduced pressure to obtain 8.2 g of the target product as a yellow solid. Melting point: 224-226°C.

[0427] Reference Example 3, Step 4: Synthesis of N-(2-bromo-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide To 12.7 g of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)isoxazole-3-carboxamide, 400 ml of tetrahydrofuran was added, and 7.1 g of bromine was added at 0°C, followed by stirring at 0°C for 3 hours. Thereafter, 22.4 g of triethylamine was added, and the mixture was stirred at 0°C for 30 minutes. After completion of the reaction, 300 ml of saturated aqueous ammonium chloride solution was added dropwise to the reaction mixture at room temperature, followed by extraction with ethyl acetate (300 ml x 2). The obtained organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting solid was washed with 100 ml of diisopropyl ether to give 8.8 g of the target product as a yellow solid, melting point 139-141°C.

[0428] Reference Example 4: Synthesis of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)isoxazole-3-carboxamide Under a nitrogen atmosphere, 3 ml of 1,4-dioxane was added to 198 mg of N-(2-bromo-2-(1,5-dimethyl-1H-pyrazol-4-yl)vinyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide, and 344 mg of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 262 mg of potassium acetate, and 22 mg of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (divalent) were added at room temperature, and the mixture was heated to 100°C and stirred. After completion of the reaction, 5 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (10 ml x 2). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to give 50 mg of the desired product as a yellow solid, melting point 146-148°C.

[0429] Reference Example 5 Synthesis of N-(2-(6-chloropyridin-2-yl)-2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-hydroxyethyl)-5-(2,4-difluorophenyl)isoxazole-3-carboxamide To a mixed solution of 6.0 g of 2-chloro-6-iodopyridine and 15 ml of tetrahydrofuran was added 12.3 ml of a tetrahydrofuran solution of isopropylmagnesium chloride lithium chloride complex (1.3 mol / l) at 0°C, and the mixture was stirred for 30 minutes. Thereafter, the mixture was added dropwise to a mixed solution of 1.0 g of 5-(2,4-difluorophenyl)-N-(2-(1,5-dimethyl-1H-pyrazol-4-yl)-2-oxoethyl)isoxazole-3-carboxamide and 15 ml of tetrahydrofuran at 0°C, and the mixture was stirred at 0°C for 1 hour. After the reaction was completed, 10 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (10 ml x 3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent, to obtain 30 mg of the target product as a yellow oil. 1 H-NMR (CDCl3, Me4Si, 400MHz): δ 8.20-6.81 (m, 9H), 5.32 (s, 1H), 4.26-4.02 (m, 2H), 3.73 (s, 3H), 2.14 (s, 3H).

[0430] Reference Example 6: Synthesis of N-(2-(6-chloropyridin-2-yl)-2-iodovinyl)-5-methylisoxazole-3-carboxamide Reference Example 6, Step 1: Synthesis of 5-methyl-N-vinylisoxazole-3-carboxamide To 5.0 g of 5-methylisoxazole-3-carboxylic acid, 50 ml of methylene chloride was added, and then 5.6 g of N-vinylformamide, 11.9 g of triethylamine, and 45 ml of a 50% by mass solution of propylphosphonic anhydride in ethyl acetate were added at room temperature, followed by stirring for 5 minutes. Thereafter, 1.0 g of N,N-dimethylamine-4-amine was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, 100 ml of 5% by mass hydrochloric acid was added dropwise to the reaction mixture at room temperature, followed by extraction with ethyl acetate (30 ml x 3 times). The obtained organic layer was washed with 30 ml of water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was used in the next step without purification.

[0431] Reference Example 6, Step 2: Synthesis of N-(2-(6-chloropyridin-2-yl)vinyl)-5-methylisoxazole-3-carboxamide To 2.7 g of 5-methyl-N-vinylisoxazole-3-carboxamide were added 2.1 g of 2-chloro-6-iodopyridine, 3.8 g of sodium carbonate, and 2.4 g of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(divalent) dichloride, and 30 ml of 1,4-dioxane was added under a nitrogen atmosphere and the mixture was stirred at 100°C for 5 days. After completion of the reaction, 30 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (30 ml x 3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent to obtain 1.8 g of the target product as a pale yellow oily substance. 1 H-NMR (CDCl3, Me4Si, 300MHz): δ 12.90-8.36 (m, 1H), 8.19-5.60 (m, 6H), 2.70-2.32 (m, 3H).

[0432] Reference Example 6, Step 3: Synthesis of N-(2-(6-chloropyridin-2-yl)-2-iodovinyl)-5-methylisoxazole-3-carboxamide To 190 mg of N-(2-(6-chloropyridin-2-yl)vinyl)-5-methylisoxazole-3-carboxamide were added 10 ml of tetrahydrofuran and 2 ml of N,N-dimethylformamide, and 441 mg of N-iodosuccinimide was added at room temperature, followed by stirring at 50°C for 3 hours. After completion of the reaction, 10 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (20 ml x 3 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate as an eluent to obtain 220 mg of the target product as a brown solid. Melting point: 135-137°C.

[0433] Reference Example 7: Synthesis of 2-(6-chloropyridin-2-yl)-2-(5-ethoxy-1-methyl-1H-pyrazol-4-yl)ethen-1-amine Reference Example 7, Step 1: Synthesis of (6-chloropyridin-2-yl)(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone To 1.38 g of 6-chloropicolinic acid, 20 ml of methylene chloride was added, and 1.33 g of oxalyl chloride and 1 drop of N,N-dimethylformamide were added at room temperature, followed by stirring for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure, and 5 ml of 1,4-dioxane was added to prepare an acid chloride solution of 6-chloropicolinic acid. To 0.86 g of 1-methyl-1H-pyrazol-5-ol, 10 ml of 1,4-dioxane and 1.30 g of calcium hydroxide were added, and the mixture was cooled to 0°C. To this was added an acid chloride solution of 6-chloropicolinic acid, and the mixture was stirred at 0°C for 1 hour. The temperature was then raised to room temperature, and the mixture was stirred for an additional 1 hour. After completion of the reaction, 10 ml of 10% by mass hydrochloric acid was added dropwise to the reaction mixture at room temperature, and the precipitated solid was filtered and washed with 20 ml of water. The resulting solid was dissolved in 30 ml of chloroform, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.67 g of the target product as a yellow solid. Melting point: 197-199°C.

[0434] Reference Example 7, Step 2: Synthesis of (6-chloropyridin-2-yl)(5-ethoxy-1-methyl-1H-pyrazol-4-yl)methanone 15 ml of N,N-dimethylformamide, 4.01 g of cesium carbonate, and 1.42 g of diethyl sulfate were added to 1.46 g of (6-chloropyridin-2-yl)(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, 30 ml of water was added dropwise to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate (30 ml x 2). The resulting organic layer was washed with 30 ml of water, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.49 g of the target product as a yellow solid. Melting point: 59-61°C.

[0435] Reference Example 7, Step 3: Synthesis of (6-chloropyridin-2-yl)(5-ethoxy-1-methyl-1H-pyrazol-4-yl)methanol 5 ml of methanol and 0.014 g of sodium tetrahydroborate were added to 0.10 g of (6-chloropyridin-2-yl)(5-ethoxy-1-methyl-1H-pyrazol-4-yl)methanone, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, the solvent was evaporated from the reaction mixture under reduced pressure, 10 ml of water was added dropwise at room temperature, and the mixture was extracted with dichloromethane (10 ml × 2 times). The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.081 g of the target product as a white solid. 1 H-NMR (CDCl3, Me4Si, 400MHz):δ 7.70-7.55 (m, 1H), 7.32-7.04 (m, 3H), 5.78-5.65 (m, 1H), 4.32-4.10 (m, 3H), 3.63 (s, 3H), 1.40-1.21 (m, 3H).

[0436] Reference Example 7, Step 4: Synthesis of 2-(6-chloropyridin-2-yl)-2-(5-ethoxy-1-methyl-1H-pyrazol-4-yl)acetonitrile 50 ml of 1,2-dichloroethane, 0.42 g of lithium carbonate, 10.0 ml of trimethylsilyl cyanide, and 1.43 g of iodine were added to 4.31 g of 6-chloropyridin-2-yl)(5-ethoxy-1-methyl-1H-pyrazol-4-yl)methanol, and the mixture was stirred at 50°C for 1 hour. After completion of the reaction, the reaction mixture was cooled to 0°C, 20 ml of a 10% by mass aqueous sodium thiosulfate solution was added, and the mixture was stirred for 10 minutes. The mixture was then extracted with dichloromethane (30 ml x 2) at room temperature. The resulting organic layer was dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography using n-hexane:ethyl acetate (gradient from 9:1 to 1:9) as an eluent to obtain 1.44 g of the desired product as a brown oil. 1 H-NMR (CDCl3, Me4Si, 400MHz): δ 7.90-7.19 (m, 4H), 5.14 (s, 1H), 4.30-4.00 (m, 2H), 3.69 (s, 3H), 1.50-1.30 (m, 3H).

[0437] Reference Example 7, Step 5: Synthesis of 2-(6-chloropyridin-2-yl)-2-(5-ethoxy-1-methyl-1H-pyrazol-4-yl)ethen-1-amine To 1.45 g of 2-(6-chloropyridin-2-yl)-2-(5-ethoxy-1-methyl-1H-pyrazol-4-yl)acetonitrile, 30 ml of tetrahydrofuran and 0.73 ml of triethylamine were added, and 15.7 ml of an n-hexane solution of diisobutylaluminum hydride (1.0 mol / L) was added at 0°C and stirred for 4 hours. After completion of the reaction, 50 ml of a 20% by mass aqueous solution of potassium sodium tartrate was added to the reaction mixture, and the mixture was stirred for 1 hour. The mixture was then extracted with ethyl acetate (50 ml x 2). The resulting organic layer was washed with 30 ml of saturated brine, dehydrated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. To the resulting residue was added 3 ml of diisopropyl ether, and the precipitated crystals were collected by filtration to give 0.72 g of the target product as a yellow solid, melting point 101-103°C.

[0438] The compounds and intermediates of the present invention can be synthesized in accordance with the above Synthesis Examples and Reference Examples. Examples of the compounds and intermediates of the present invention that were produced in the same manner as in the Synthesis Examples are shown in Tables 2 to 13, but the compounds and intermediates of the present invention are not limited to these.

[0439] In the table, the substituent marked "Me" represents "methyl", and similarly, "Et" represents "ethyl", "iBu" represents "isobutyl", "tBu" represents "tertiary butyl", "nPr" represents "normal propyl", "iPr" represents "isopropyl", "cPr" represents "cyclopropyl", "nPen" represents "normal pentyl", "cPen" represents "cyclopentyl", "nHex" represents "normal hexyl", "cHex" represents "cyclohexyl", "nHep" represents "normal heptyl", and "Ph" represents "phenyl". In addition, the notation "*" indicates that the compound is an oily or resinous compound with no melting point, and "m.p." represents the melting point (unit: °C).

[0440] In the table, for example, the "4-" in "Ph-4-Me" indicates the substitution position on the phenyl group as described below. For example, "Ph-4-Me" represents 4-methylphenyl, "Ph-2,6-F2" represents 2,6-difluorophenyl, and "Ph-2-Me-4-F" represents 2-methyl-4-fluorophenyl. The absence of a substituent designation indicates unsubstituted.

[0441] Further, the substituents represented by G-1a to G-4a, G-8a, G-10a, G-13a, G-15a to G-23a, G-29a to G-31a, G-34a to G-36a, G-39a, G-39b, G-39c, G-50a, G-50b, G-51a, G-51b, G-51c, G-52a to G-60a, G-65a, G-66a, L-1a, F-1a, E-6a, E-7a, E-12a, E-38a, E-45a, E-61a, E-87a to E-90a, D-41a to D-49a and D-50a respectively represent the following structures.

[0442] In the table, for example, the description "6-" in "(G-52a)-6-Cl" indicates the substitution position on the substituent represented by G-52a as described below. For example, "(G-52a)-6-Cl" represents 6-chloropyridine, "(G-52a)-4,6-Cl2" represents 4,6-dichloropyridine, and "(G-52a)-3-F-5-Cl" represents 3-fluoro-5-chloropyridine.

[0443] "(G-31a)-3-((G-52a)-3,5-F2)" represents the following structure. Note that the absence of a substituent designation indicates unsubstituted.

[0444] The compound (1) of the present invention has the following two geometric isomers due to the enamine structure.

[0445] Of the above geometric isomers, the compound with the slowest retention time in the following LCMS analysis (condition a or condition b) was estimated to be the configuration of "compound (1A)," and the compound with the fastest retention time was estimated to be the configuration of "compound (1B)." The proportion of compound (1A) is shown in the table as "A ratio" (unit: %, the numerical value is the area percentage of compound (1A) relative to the sum of the peak area percentages of compound (1A) and compound (1B) in the LCMS analysis). For example, an A ratio of 100 indicates that compound (1A) is contained in 100% and compound (1B) is contained in 0%; 50 indicates that compound (1A) is contained in 50% and compound (1B) is contained in 50%; and 0 indicates that compound (1A) is contained in 0% and compound (1B) is contained in 100%.

[0446] In addition, in the table, when measurements were made under condition b, "*1" is entered in the "A rate" column.

[0447] R １ and R ２ When the structures are the same, no geometric isomers resulting from the enamine structure exist, and in such cases, "-" is entered in the "A ratio" column in the table.

[0448] [Condition a] LCMS apparatus: NexeraX2 LC-30 (Shimadzu Corporation) and PDA detector and LCMS-2020 (ESI / APCI mode, Shimadzu Corporation) Flow rate: 0.3 ml / min Oven temperature: 40°C Mobile phase: Mobile phase (A) water containing 0.1% by mass of formic acid, mobile phase (B) acetonitrile containing 0.1% by mass of formic acid. The concentration of mobile phase (B) was increased from 40% by mass to 95% by mass using a linear gradient over 5 minutes and maintained at 95% by mass for 0.3 minutes. Column: ODS-4 column (GL Sciences, 2.1 x 30 mm, 2 µm) Measurement wavelength: 254 nm [Condition b] LCMS apparatus: NexeraX2 LC-30 (Shimadzu Corporation) and PDA detector and LCMS-2020 (ESI / APCI mode, Shimadzu Corporation) Flow rate: 0.3 ml / min Oven temperature: 40°C Mobile phase: Mobile phase (A) water containing 0.1% by mass formic acid, mobile phase (B) acetonitrile containing 0.1% by mass formic acid. The concentration of the mobile phase (B) was increased from 40% by mass to 95% by mass in a linear gradient over 5 minutes and maintained at 95% by mass for 0.3 minutes. Column: InertSustain Phenyl column (manufactured by GL Sciences, 2.1 x 30 mm, 2 µm). Measurement wavelength: 254 nm.

[0449] In addition, in the table, geometric isomers resulting from other than the enamine structure may exist. For example, the "(E)" in "(G-34a)-5-C(CH3)=CHCH3 (E)" indicates that the geometric isomer resulting from the double bond is the E-form, as shown in the formula shown in "E-form" below. Similarly, the "(Z)" in "(G-34a)-5-CH=CHCl (Z)" indicates that the geometric isomer resulting from the double bond is the Z-form, as shown in the formula shown in "Z-form" below. Note that compounds without the notation "(E)" or "(Z)" represent a mixture of these geometric isomers.

[0450] [Table 2] ―――――――――――――――――――――――――――――――― No. R 2 R 5aam.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 1-001 (G-52a)-6-Cl Ph-2,4-F2 214 - 216 100 1-002 (G-16a)-5-Cl Ph-2,4-F2 224 - 226 ‐ 1-003 (G-52a)-6-Me Ph-2,4-F2 198 - 200 100 1-004 (G-52a)-6-Me Ph-2,4-F2 * 0 1-005 (G-52a)-6-C(O)Me Ph-2,4-F2 221 - 223 65 1-006 (G-52a)-6-C(=NOMe)Me Ph-2,4-F2 199 - 201 75 1-007 (G-52a)-6-Cl Ph * 100 1-008 (G-52a)-6-Cl Ph 203 - 205 0 1-009 (G-52a)-6-Cl Me 150 - 170 70 1-010 (G-52a)-6-Cl Ph-4-Me 210 - 212 100 1-011 (G-52a)-6-Cl Ph-4-Me * 0 1-012 (G-52a)-6-Cl Ph-4-Cl 191 - 193 100 1-013 (G-52a)-6-Cl Ph-4-Cl * 0 1-014 (G-15a) Ph-2,4-F2 368 - 370 100 *1 1-015 (G-52a) Ph-2,4-F2 190 - 192 100 *1 1-016 (G-22a)-2-Br Ph-2,4-F2 209 - 211 100 *1 1-017 (G-52a)-6-Cl G-52a 167 - 169 100 *1 1-018 (G-52a)-6-Cl G-1a 191 - 193 100 *11-019 (G-52a)-6-Cl H 169-171 100 *1 1-020 (G-55a)-4-Cl Ph-2,4-F2 239-241 100 *1 1-021 (G-52a)-6-Cl CH2iPr 117-119 100 *1 1-022 (G-52a)-6-Me Me 172-174 100 *1 1-023 (G-52a)-6-Me Me 144-146 0 *1 1-024 (G-52a)-6-Me G-1a 186-188 100 *1 1-025 (G-52a)-6-Me G-1a 149-151 0 *1 1-026 (G-52a)-6-Me nPr 84-94 100 *1 1-027 (G-52a)-6-Me (G-52a)-5-F 214-215 100 1-028 (G-52a)-6-Me (G-52a)-5-F 184-185 0 1-029 (G-52a)-6-Cl CH2OMe 97-99 100 *1 1-030 (G-52a)-6-Cl (G-52a)-3,5-F2 249-251 100 ―――――――――――――――――――――――――――――――――― [Table 3] ―――――――――――――――――――――――――――――――――― No. R 2 R 5aam.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 2-001 (G-52a)-6-Cl Ph-2,4-F2 214-216 100 2-002 (G-52a)-6-Cl Ph-2,4-F2 209-211 0 2-003 (G-52a)-6-Cl Me 179-181 100 *1 2-004 (G-52a)-6-Cl Ph 179-185 90 *1 2-005 (G-52a)-6-Cl G-1a 172-174 100 *1 2-006 (G-52a)-6-Cl Et 152-154 100 *1 2-007 (G-52a)-6-Cl G-3a 216-218 100 *1 2-008 (G-52a)-6-Cl C(O)Me 254-256 0 *1 2-009 (G-52a)-6-CF3 Me 126-128 0 2-010 (G-52a)-6-F Me 170-172 0 2-011 (G-52a)-6-C(O)Me Me 196-198 0 2-012 (G-52a)-6-C(O)Me Me 146-148 100 2-013 (G-52a)-6-Cl CH2iPr 87-89 0 *1 2-014 (G-52a)-6-Cl nPr 122-124 100 *1 2-015 (G-52a)-6-Cl G-21a 236-238 0 *1 2-016 (G-52a)-6-CN Me 129-131 0 2-017 (G-52a)-6-Cl G-21a 192-194 100 *12-018 (G-52a)-6-Br Me 137-139 100 2-019 (G-52a)-6-CN Me 69-71 100 2-020 (G-52a)-6-OMe Me 157-159 100 2-021 (G-52a)-6-C(O)OMe Me 129-131 50 2-022 (G-52a)-6-Cl (G-52a)-5-F 192-194 100 *1 2-023 (G-52a)-6-Me (G-52a)-5-F 207-209 100 2-024 (G-52a)-6-Me (G-52a)-5-F 214-216 65 2-025 (G-52a)-6-Me CH2iPr 96-98 100 *1 2-026 (G-52a)-6-Cl CH2Cl 195-197 100 *1 2-027 (G-52a)-6-Cl CH2OH 198-200 70 *1 2-028 (G-52a)-6-Cl tBu * 100 *1 2-029 (G-52a)-6-Cl cPr * 100 *1 2-030 (G-52a)-6-Cl H * 100 *1 2-031 (G-52a)-6-Cl C(O)Me * 100 *12-032 (G-52a)-6-Me Me * 1002-033 (G-52a)-6-CF3 Me * 652-034 (G-52a)-6-Cl C(=NOMe)Me * 1002-035 (G-52a)-6-C(=NOMe)Me Me * 02-036 (G-52a)-6-C(=NOMe)Me Me * 802-037 (G-52a)-6-Cl nPr * 0 *1 2-038 (G-52a)-6-Cl iPr * 0 *1 2-039 (G-52a)-6-Cl iBu * 100 *1 2-040 (G-52a)-6-Cl iPr * 100 *1 2-041 (G-52a)-4,6-Cl2 Me * 652-042 (G-52a)-6-Me nPr * 100 *1 2-043 (G-52a)-​​​m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 3-001 (G-52a)-6-Me Ph-2,4-F2 167-168 30 3-002 (G-52a)-6-Cl Ph-2,4-F2 202-204 100 3-003 (G-52a)-6-Cl Ph-2,4-F2 192-194 0 3-004 (G-52a)-6-Cl G-1a 194-196 95 *1 3-005 (G-52a)-6-Cl nPr 89-91 100 *1 3-006 (G-52a)-6-Cl G-1a 197-199 0 *1 3-007 (G-52a)-6-Cl nPr 94-96 0 *1 3-008 (G-52a)-6-Cl (G-52a)-3,5-F2 224-226 100 3-009 (G-52a)-6-Cl Me * 100 ―――――――――――――――――――――――――――――――――― [Table 5] ―――――――――――――――――――――――――――――――――― No. R 5 m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 4-001 C(O)Ph * 60 *1 4-002 CH2(Ph-4-OCF3) 101-103 100 *1 4-003 C(O)NHNH(Ph-2,4-F2) 92-94 100 *1 4-004 C(O)NH(Ph-2,4-F2) 169-171 90 *14-005 C(O)NH((G-52a)-3-F-5-Cl) 251-253 100 4-006 C(O)NH((G-52a)-3-F-5-Me) 227-229 100 4-007 C(O)NH((G-52a)-5-F) 218-220 100 *1 4-008 C(O)NH((G-52a)-3,5-F2) 117-119 100 4-009 C(O)NH((G-55a)-5-F) 237-239 100 ―――――――――――――――――――――――――――――――――― [Table 6] ―――――――――――――――――――――――――――――――――― No. R 5 m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 5-001 C(O)NHtBu 147-149 95 *1 5-002 C(O)NH((G-52a)-5-F) 216-218 100 *1 5-003 C(O)NH(Ph-2,4-F2) 212-214 100 *1 5-004 C(O)OEt 142-144 80 *1 5-005 C(O)S(Ph-2,4-F2) 202-204 100 *1 5-006 C(O)(L-1a) 109-111 100 *1 5-007 C(O)CH=CH(Ph-2,4-F2) (E) 182-184 95 *1 5-008 C(O)NHPh 219-221 100 *1 5-009 C(O)NH(Ph-2-F) 122-124 70 *1 5-010 C(O)NH(Ph-3-F) 244-246 100 *15-011 C(O)NH(Ph-4-F) 244-246 100 *1 5-012 C(O)NH(Ph-2,4,6-F3) 229-231 100 *1 5-013 C(O)NH(Ph-2,3-F2) 189-191 70 *1 5-014 C(O)NH(Ph-4-Cl) 191-193 100 *1 5-015 C(O)NH(Ph-4-Br) 231-233 100 *1 5-016 C(O)NH(Ph-4-Me) 187-189 100 *1 5-017 C(O)NH(Ph-4-OMe) 184-186 100 *1 5-018 C(O)NH(Ph-4-Et) 194-196 100 *1 5-019 C(O)NH(Ph-4-CN) 265-267 0 *1 5-020 C(O)NH(Ph-4-CF3) 217-219 0 *1 5-021 C(O)NH(Ph-4-CN) 222-224 100 *1 5-022 C(O)NH(Ph-4-SMe) 231-233 100 *1 5-023 C(O)NH(Ph-4-CF3) 227-229 100 *1 5-024 C(O)NH(G-52a) 176-178 100 *1 5-025 C(O)NH(G-54a) 232-234 0 *1 5-026 C(O)NH(G-59a) 212-214 70 *1 5-027 C(O)NHMe 151-153 70 *1 5-028 C(O)NHEt 154-156 100*1 5-029 C(O)NHiPr 92-94 80 *1 5-030 C(O)NHcPen 171-173 80 *1 5-031 C(O)O(Ph-2,4-F2) 177-179 100 *1 5-032 C(O)NH(G-8a) 217-219 70 *1 5-033 C(O)NH((G-8a)-5-Me) 202-204 80 *1 5-034 C(O)NH(G-15a) 197-199 100 *1 5-035 C(O)NH(G-21a) 239-241 100 *1 5-036 C(O)NH(G-18a) 214-216 100 *1 5-037 C(O)NH((G-54a)-3-F) 219-222 100 *1 5-038 C(O)NH((G-52a)-5-F) 131-133 70 *1 5-039 C(O)NH((G-52a)-6-F) 197-199 80 *1 5-040 C(O)NH((G-52a)-3-F-5-Cl) 231-233 100 *1 5-041 C(O)NH(Ph-3-Me) 177-179 0 *1 5-042 C(O)NH(Ph-3-OMe) 146-148 30 *1 5-043 C(O)NH(Ph-3-Me) 201-203 100 *1 5-044 C(O)NH(Ph-3-OH) 214-216 100 *1 5-045 C(O)NH(Ph-3-OMe) 179-181 100 *5-046 C(O)NH(Ph-2-CN) 242-254 100 *1 5-047 C(O)NHcPr 144-146 100 *1 5-048 C(O)NH(Ph-2-Me) 124-126 60 *1 5-049 C(O)NH(Ph-2-OMe) 186-188 10 *1 5-050 C(O)NH(Ph-3-Cl) 159-161 50 *1 5-051 C(O)NH(Ph-2-Cl) 172-174 80 *1 5-052 C(O)NH(Ph-2-Me) 159-161 100 *1 5-053 C(O)NH(Ph-2-OH) 232-234 80 *1 5-054 C(O)NH(Ph-2-OMe) 186-188 100 *1 5-055 C(O)NH(Ph-3-Cl) 229-231 100 *15-056 C(O)NH(Ph-2-F-4-Br) 201-203 80 5-057 C(O)NH(Ph-4-I) 206-208 90 5-058 C(O)NH(G-53a) 262-264 80 5-059 C(=NOMe)Me 138-140 50 5-060 C(O)NH((G-52a)-5-Me) 201-203 100 5-061 C(O)NH((G-52a)-5-Cl) 209-211 100 5-062 C(O)NH((G-52a)-5-Br) 216-218 100 5-063 C(O)NH((G-52a)-5-OMe) 177-179 85 5-064 C(O)NH((G-52a)-5-CF3) 176-178 100 5-065 C(O)NH((G-52a)-5-NO2) 269-271 100 5-066 C(O)NH((G-52a)-3-F) 230-232 100 5-067 C(O)NH((G-52a)-3-F-5-Br) 262-264 100 5-068 C(O)NH((G-52a)-5-F) 120-122 0 5-069 C(O)NH((G-55a)-5-Cl) 237-239 100 5-070 C(O)NH((G-55a)-5-F) 241-243 100 5-071 NH(Ph-4-F) 212-214 0 *1 5-072 NMe2 194-196 100 *15-073 C(O)NH((G-52a)-3-NO2) 227-229 100 5-074 C(O)NH((G-52a)-3-CN) 256-258 100 5-075 C(O)NH((G-52a)-3-Cl) 189-191 100 5-076 C(O)NH((G-52a)-3-Br) 197-199 100 5-077 C(O)NH((G-52a)-3,5-F2) 219-221 90 5-078 C(O)NH(G-55a) 209-211 100 5-079 C(O)NH((G-52a)-3-OMe) 211-213 100 5-080 C(O)NH((G-52a)-3-C(O)Me) 112-114 100 5-081 C(O)NH((G-52a)-3-C(O)OEt) 209-211 100 5-082 C(O)NMePh * 100 *1 5-083 C(O)NH(OMe) * 70 *1 5-084 C(O)NMe(OH) * 100 *1 5-085 C(O)NH(Ph-3,4-F2) * 100 *1 5-086 C(O)NMe(Ph-2,4-F2) * 0 *1 5-087 C(O)NHNHPh * 100 *1 5-088 C(O)NH(Ph-2,6-F2) * 100 *1 5-089 C(O)NMe(Ph-2,4-F2) * 100 *1 5-090 C(O)NH(Ph-2,6-F2) * 0 *1 5-091 C(O)NMe(Ph-4-F) * 100 *1 5-092 C(O)NHNHC(O)CF3 * 100*1 5-093 C(O)NH((G-52a)-3,5-F2) * 80 *1 5-094 C(O)NH((G-52a)-3-Cl-5-F) * 100 *1 5-095 C(O)NH((G-53a)-2,6-F2) * 100 *1 5-096 C(O)NH((G-52a)-3-Br-5-F) * 100 5-097 C(O)NH((G-52a)-3-F-5-Me) * 100 5-098 C(O)NH((G-52a)-5-CF3) * 0 5-099 NH(Ph-4-F) * 100 *1 5-100 C(O)NH((G-52a)-3-Me-5-F) * 100 *15-101 C(O)NH((G-52a)-5-CN) 273-275 90 5-102 C(O)NH((G-55a)-5-Me) 237-239 100 5-103 C(O)NHC(=NH)(Ph-4-Cl) * 100 5-104 C(O)NH((G-52a)-5-Et) * 90 5-105 C(O)NH((G-52a)-5-C(O)Me) 244-246 70 5-106 C(O)NH((G-52a)-5-C(O)OMe) 218-220 100 5-107 C(O)NH(G-60a) * 100 5-108 C(O)NH(G-58a) 242-244 85 5-109 C(O)NH((G-53a)-6-F) * 100 5-110 C(O)NH((G-18a)-4,5-Me2) * 80 5-111 C(O)NH((G-59a)-3-Cl) 238-240 90 5-112 C(O)NH((G-58a)-5-Cl) 237-239 0 5-113 C(O)NH((G-58a)-5-Cl) 252-254 90 5-114 C(O)NH((G-10a)-5-Me) 248-250 100 5-115 C(O)NH((G-52a)-4-F) 234-236 100 5-116 C(O)NH((G-58a)-6-Cl) 216-218 90 5-117 C(O)NHCH2CH2CH2CF3 133-135 100 5-118 C(O)NH(G-15a) * 0 5-119 C(O)NH((G-15a)-5-Me) * 0 5-120 C(O)NHC(=NH)(Ph-3-F) * 100 5-121 C(O)NH(G-29a) 249-251 100 5-122 C(O)NH(G-15a) 221-223 80 5-123 C(O)NH((G-15a)-5-Me) 229-231 100 5-124 C(O)NH(G-16a) * 100 5-125 C(O)NH((G-16a)-5-Me) 99-101 100 5-126 C(O)NH((G-30a)-5-Me) 227-229 100 5-127 C(O)NH((G-36a)-3-Me) 207-209 0 5-128 C(O)NH((G-17a)-3-Me) * 85 5-129 C(O)NH(G-17a) 99-101 85 5-130 CH2NHC(O)OMe 154-156 100, *15-131 C(O)NH(E-87a) * 100 5-132 C(O)NHNHC(O)OtBu 216-218 100 5-133 C(O)NHNH((G-52a)-3,5-F2) * 100 5-134 C(O)NH((G-57a) * 90 5-135 C(O)NHNHC(O)((G-52a)-3,5-F2) 211-213 100 5-136 C(O)(E-12a) 157-159 100 5-137 C(O)NHcHex 176-178 85 5-138 C(O)NH(E-88a) 267-269 100 ―――――――――――――――――――――――――――――――――― [Table 7] ―――――――――――――――――――――――――――――――――― No. R 1aa R 2ac R 5 m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 6-001 Me Cl (G-10a)-5-Me 147-149 70 *1 6-002 Me Cl G-10a 122-124 100 *1 6-003 Me Cl (G-10a)-5-Br 182-184 100 *1 6-004 Me Cl (G-10a)-5-Ph 167-169 0 *1 6-005 Me Cl (G-13a)-3-Ph 164-166 80 *1 6-006 Br Cl (G-8a)-5-Me 192-194 100 6-007 Cl Cl C≡CMe 119-121 100 *16-008 Et Cl (G-8a)-5-Me 173-175 100 6-009 Me Cl (G-31a)-3-Et 161-163 100 6-010 Me Cl (G-30a)-5-Me 206-208 100 *1 6-011 Me Cl (G-31a)-3-(Ph-2-Me-4-F) 203-205 100 6-012 Me Cl (G-31a)-3-(Ph-2-OMe-4-F) 167-170 100 6-013 Me Cl (G-31a)-3-Me 184-186 100 6-014 Me Cl (G-21a) 219-221 0 *1 6-015 Me Cl Ph 125-127 80 *1 6-016 Me Cl (G-21a) 140-142 100 *1 6-017 Me Cl (G-10a)-5-cHex 179-181 0 *1 6-018 Me Cl (G-10a)-5-Cl 179-181 0 *1 6-019 Me Cl (G-10a)-5-OMe 144-146 70 *1 6-020 Me Cl (G-10a)-5-CHF2 257-259 90 *1 6-021 Me Cl (G-10a)-5-cHex 154-156 100 *1 6-022 Me Cl (G-10a)-4-Me 137-139 70 *1 6-023 Me Cl (G-10a)-5-Cl 201-203 100 *1 6-024 Br Cl (G-8a)-5-(G-1a) 179-181 100 *16-025 Me Cl (G-31a)-3-((G-52a)-5-F) 274-276 100 *1 6-026 Me Cl G-3a 154-156 100 6-027 Me Me (G-31a)-3-Me 181-183 100 6-028 Me Cl (G-30a)-5-Me 202-204 0 *1 6-029 Me Cl (G-18a)-5-Me 174-176 0 *1 6-030 Me Cl (G-31a)-3-(G-21a) 249-251 100 6-031 Me Me (G-31a)-3-Et 138-139 100 6-032 Me Cl (G-31a)-3-(G-1a) 222-224 100 6-033 Me Cl (G-31a)-3-((G-22a)-2-CF3) 234-236 100 6-034 Me Cl (G-35a)-5-(Ph-2,4-F2) 219-221 90 *1 6-035 Me Cl (G-34a)-5-Me 205-207 0 *1 6-036 Me Me (G-30a)-5-Me 115-117 50 *1 6-037 Cl Cl (G-10a)-5-Me 206-208 100 *1 6-038 Me Me (G-10a)-5-Me 191-193 100 *1 6-039 Me Cl (G-31a)-3-((G-22a)-2-CF3) 170-172 0 6-040 Me Cl (G-34a)-5-Me 187-189 100 *1 6-041 Cl Cl (G-30a)-5-Me 177-179 100 *16-042 Me Cl (G-35a)-5-Me 181-183 100 *1 6-043 Cl Cl (G-31a)-3-Me 188-190 100 6-044 Cl Cl (G-31a)-3-((G-52a)-3,5-F2) 205-207 100 6-045 Cl Cl (G-31a)-3-Et 161-163 100 6-046 Me Cl (G-31a)-3-(G-8a) 241-243 100 6-047 Me Cl (G-31a)-3-(G-8a) 234-236 65 6-048 Me Cl (G-31a)-3-nPr 167-169 65 6-049 Me Cl (G-31a)-3-nBu 152-154 100 6-050 Me Cl (G-31a)-3-CH2cPr 178-180 100 6-051 Me Cl (G-31a)-3-CH2OMe 173-175 100 6-052 Me Cl (G-31a)-3-CH2CH2CF3 165-167 100 6-053 Me Cl (G-31a)-3-((G-52a)-3,5-F2) 222-224 100 6-054 Cl Me (G-10a)-5-Me 197-199 100 *1 6-055 Cl Me (G-10a)-5-Me 147-149 0 *16-056 Cl Cl (G-31a)-3-Me 213-215 50 6-057 Me Cl (G-31a)-3-nPr 159-161 0 6-058 Me Cl (G-31a)-3-CH2cPr 180-182 0 6-059 Me Cl (G-31a)-3-CH2CH2CF3 145-147 0 6-060 Cl Cl (G-30a)-5-(G-1a) 197-199 100 *1 6-061 Me Cl (G-10a)-5-(G-52a) 199-201 40 *1 6-062 Me Cl (G-10a)-5-((G-23a)-2,4-Me2) 214-216 0 *1 6-063 Me Me (G-31a)-3-((G-52a)-5-F) 241-243 100 6-064 Me Cl (G-31a)-3-CH=CHCF3 (E) 230-231 100 6-065 Me Cl (G-31a)-3-(G-22a) 245-247 100 6-066 Cl Me (G-31a)-3-(G-1a) 198-200 100 6-067 Cl Me (G-31a)-3-((G-52a)-3,5-F2) 202-204 100 6-068 Cl Me (G-31a)-3-nPr 137-138 100 6-069 Br Cl (G-31a)-3-((G-52a)-3,5-F2) 197-199 100 6-070 Me Cl (G-10a)-5-((G-23a)-2,4-Me2) 194-196 60 *16-071 Me Cl (G-31a)-3-CH=CHCF3 (E) 217-219 0 6-072 Cl Me (G-31a)-3-(G-1a) 164-166 0 6-073 Me Cl (G-10a)-5-((G-23a)-2-Cl) 261-263 100 6-074 Cl Me (G-31a)-3-((G-52a)-5-F) 220-222 100 6-075 Me Cl (G-31a)-3-((G-52a)-3,5-F2) 197-199 35 6-076 Me Cl (G-10a)-5-((G-52a)-5-F) 186-188 70 *1 6-077 Me Cl (G-10a)-5-((G-52a)-3,5-F2) 251-253 60 *1 6-078 Me Cl (G-31a)-3-(G-58a) 254-256 100 6-079 Me Cl (G-31a)-3-(G-56a) 216-218 100 6-080 Me Cl (G-31a)-3-((G-52a)-6-F) 271-273 100 6-081 Me Cl (G-31a)-3-((G-52a)-4-F) 191-193 100 6-082 Me Cl (G-19a)-2-Me * 100 *1 6-083 Me Cl F-1a * 80 *1 6-084 Cl Cl Ph-3-Me * 100 *16-085 Br Cl (G-8a)-5-Me * 0 6-086 Et Cl (G-8a)-5-Me * 0 6-087 Me Cl (G-31a)-3-(Ph-4-F) * 100 6-088 Me Cl (G-31a)-3-(Ph-2,4-F2) * 100 6-089 Me Cl (G-21a)-5-Me * 100 *1 6-090 Me Cl G-1a * 100 6-091 Me Cl (G-35a)-5-(Ph-2,4-F2) * 0 *1 6-092 Me Cl (G-18a)-5-Me * 100 *1 6-093 Me Cl nHep * 70 *1 6-094 Me Cl nHex * 100 *1 6-095 Cl Cl (G-31a)-5-Me * 0 6-096 Cl Cl (G-31a)-3-((G-52a)-3,5-F2) * 0 6-097 Cl Cl (G-31a)-3-(G-1a) * 100 6-098 Me Me (G-31a)-3-((G-52a)-3,5-F2) * 100 6-099 Me Me (G-31a)-3-(G-1a) * 100 6-100 Me Cl (G-31a)-3-CH2OMe * 0 6-101 Cl Me (G-31a)-3-nPr * 0 6-102 Me Cl G-39a 206-208 70 *1 6-103 Br Cl (G-8a)-5-nPr 151-153 100 *16-104 Me Cl (G-31a)-3-(G-52a) 221-223 100 6-105 Me Cl (G-31a)-3-((G-52a)-5-Me) 234-276 100 6-106 Me Cl (G-31a)-3-((G-52a)-5-CF3) 229-231 100 6-107 Me Cl (G-31a)-3-((G-55a)-5-Cl) 244-246 100 6-108 Me Cl (G-31a)-3-((G-55a)-5-Cl) 212-214 70 6-109 Me Cl (G-31a)-3-((G-52a)-3-CF3) 81-83 0 6-110 Me Cl (G-10a)-5-((G-1a)-5-Cl) 129-131 20 *1 6-111 Me Cl (G-31a)-3-((G-52a)-5-Me) 207-209 25 6-112 Me Cl (G-31a)-3-(G-16a) 252-254 100 6-113 Me Cl (G-31a)-3-((G-52a)-3-F) 227-229 100 6-114 Me Cl (G-31a)-3-((G-52a)-3-Cl) 186-188 100 6-115 Me Cl (G-31a)-3-((G-52a)-3-Me) 186-188 100 6-116 Me Cl (G-31a)-3-((G-52a)-3-CF3) 192-194 100 6-117 Me Cl (G-31a)-3-CH2S(O)2Me 209-211 100 6-118 Me Cl (G-10a)-5-((G-1a)-5-Cl) 181-183 100 *1 6-119 Me Cl (G-30a)-5-(G-1a) 192-194 70 *16-120 Me Cl (G-31a)-3-((G-52a)-5-Cl) 261-263 100 6-121 H Cl (G-31a)-3-((G-52a)-3,5-F2) 209-211 100 6-122 Me Cl (G-10a)-5-((G-52a)-3,5-F2) 251-253 90 *1 6-123 OMe Cl (G-31a)-3-((G-52a)-3,5-F2) * 0 6-124 OMe Cl (G-31a)-3-((G-52a)-3,5-F2) 202-204 100 6-125 Et Cl (G-31a)-3-((G-52a)-3,5-F2) 186-187 100 6-126 Me Cl (G-31a)-3-CH2CH2OMe 169-171 100 6-127 Me Cl (G-31a)-3-CH2iPr 184-186 100 6-128 Me Cl (G-31a)-3-CH2SMe 158-161 85 6-129 Me Cl (G-31a)-3-CH2CF3 144-146 100 6-130 Me Cl (G-31a)-3-CH2CH=CH 2　 171-173 100 6-131 Me Cl (G-31a)-3-(G-17a) 197-199 100 6-132 Me Cl (G-31a)-3-((G-52a)-5-OMe) 156-158 100 6-133 Me Cl (G-31a)-3-((G-52a)-3-OMe) 251-253 100 6-134 Cl Cl (G-30a)-5-(G-1a) 192-194 20 *16-135 Me Cl (G-31a)-3-nPr 182-184 0 6-136 Me Cl (G-31a)-3-CH2iPr 151-153 35 6-137 Me Cl (G-31a)-3-CH2CF3 159-161 15 6-138 Me Cl (G-31a)-3-((G-52a)-5-OMe) 92-94 0 6-139 Et Cl (G-31a)-3-((G-52a)-3,5-F2) 192-194 0 6-140 Me Cl (G-35a)-5-((G-52a)-3,5-F2) 241-243 70 *1 6-141 Cl Cl (G-35a)-5-((G-52a)-3,5-F2) 209-211 50 *1 6-142 Me Cl (G-30a)-5-((G-52a)-3,5-F2) 176-178 80 *1 6-143 Me Cl (G-31a)-3-((G-55a)-5-Cl) 244-246 100 6-144 Me Cl (G-31a)-3-CH2CH2CH=CH 2　158-160 100 6-145 Me Cl (G-31a)-3-(G-23a) 236-238 100 6-146 Me Cl (G-31a)-3-(G-18a) 242-244 100 6-147 Me Cl (G-31a)-3-(G-20a) 244-246 100 6-148 Me Cl (G-31a)-3-(G-19a) 226-228 100 6-149 Me Cl (G-31a)-3-CH2Ph 174-176 100 6-150 Me Cl (G-31a)-3-CH2(Ph-4-F) 139-141 100 6-151 Me Cl (G-31a)-3-(G-2a) 201-203 100 6-152 Me Cl (G-31a)-3-(G-55a) 234-236 100 6-153 Et Cl (G-31a)-3-((G-52a)-5-F) 202-204 90 6-154 Me Cl (G-34a)-5-((G-52a)-3,5-F2) 222-224 100 *16-155 H Cl (G-31a)-3-CH2CH2CF3 * 100 6-156 Br Cl (G-31a)-3-CH2CH2CF3 192-194 100 6-157 Me Cl (G-31a)-3-((G-58a)-6-Cl) 226-228 100 6-158 Me Cl (G-31a)-3-((G-58a)-3-Cl) 217-219 100 6-159 Me Cl (G-31a)-3-(G-3a) 251-253 100 6-160 Me Cl (G-31a)-3-((G-58a)-5-Cl) 261-263 100 6-161 Me Cl nPen 144-146 80 6-162 Cl Cl (G-31a)-3-CH2CH2CF3 167-169 100 6-163 Me Cl (G-30a)-5-CH2CH2CF3 117-119 0 6-164 Me Cl (G-30a)-5-CH2CH2CF3 142-144 85 6-165 Br Cl (G-31a)-3-((G-52a)-5-F) 233-235 100 6-166 Br Cl (G-31a)-3-((G-55a)-5-Cl) 257-259 100 6-167 Br Cl (G-31a)-3-(G-58a) 203-205 100 6-168 Br Cl (G-31a)-3-((G-55a)-5-F) 252-254 100 6-169 Me Cl (G-31a)-3-((G-52a)-3,5-Cl2) 221-223 100 6-170 Br Cl (G-31a)-3-((G-52a)-5-Cl) 248-250 100 6-171 Me Cl (G-31a)-3-(G-4a) 204-206 100 6-172 Me Cl (G-31a)-3-(G-15a) 252-254 100 6-173 Me Cl (G-31a)-3-nPen 136-138 100 6-174 Me Cl (G-52a)-3,5-F2) 232-234 100 6-175 Me Cl CH2CH2CH2CF, 3　 * 100 *1 6-176 Et Cl (G-31a)-3-CH2CH2CF3 138-140 100 6-177 Et Cl (G-8a)-5-(Ph-2,4-F2) 183-185 100 6-178 Me Cl (G-34a)-5-((G-52a)-3-OMe-5-F) 236-238 100 6-179 Me Cl G-50a * 100 6-180 Et Cl (G-34a)-5-((G-52a)-3,5-F2) 202-204 100 6-181 Et Cl (G-31a)-3-CH2CH2CH=CH 2　105-107 100 6-182 Me Cl G-51a * 70 6-183 Me Cl G-66a 232-234 100 6-184 Et Cl (G-34a)-5-((G-52a)-3,5-F2) 172-174 0 6-185 Et Cl (G-8a)-5-((G-52a)-3,5-F2) 212-214 90 6-186 Br Cl (G-8a)-5-((G-52a)-3,5-F2) 252-254 100 6-187 Me Cl G-51b 172-174 100 6-188 Me Cl G-51b 133-135 10 6-189 Et Cl (G-31a)-3-(Ph-2,4-F2) 217-219 100 6-190 Me Cl (G-31a)-3-(E-7a) 199-201 100 6-191 Et Cl (G-31a)-3-((G-52a)-5-F) 199-201 100 6-192 Et Cl (G-31a)-3-((G-52a)-5-Cl) 195-197 75 6-193 Et Cl (G-31a)-3-((G-55a)-5-Cl) 227-229 100 6-194 Et Cl (G-31a)-3-((G-55a)-5-Cl) 220-222 85 6-195 Et Cl (G-31a)-3-(G-58a) 217-219 100 6-196 Et Cl (G-31a)-3-(G-55a) 217-219 100 6-197 Et Cl (G-31a)-3-(Ph-2,4-F2) 217-219 100 6-198 Et Cl (G-31a)-3-((G-52a)-3-F) 177-179 100 6-199 Me Cl (G-31a)-3-CCl3 174-176 100 6-200 Me Cl (G-31a)-3-(E-38a) 202-204 100 6-201 Me Cl (G-31a)-3-(D-41a) 166-167 20 6-202 Me Cl (G-31a)-3-(D-41a) 167-169 100 6-203 Me Cl (G-31a)-3-CH2CH=CHCH3 (E) 157-159 15 6-204 Me Cl (G-31a)-3-CH2CH=CHCH3 (E) 169-171 100 6-205 Me Cl (G-31a)-3-CH(CH3)(CH=CH2) 129-131 20 6-206 Me Cl (G-31a)-3-CH(CH3)(CH=CH2) 154-156 100 6-207 CF3 Cl (G-31a)-3-((G-52a)-3,5-F2) 174-176 100 6-208 Me Cl (G-31a)-3-CH2CH2CH2CH=CH2 128-130 100 6-209 Me Cl (G-31a)-3-CH2CH2C≡CH 149-151 90 6-210 Me Cl (G-31a)-3-CH2CH2C≡N 209-211 100 6-211 Cl Cl (G-34a)-5-((G-52a)-3,5-F2) 252-254 100 6-212 Br Cl (G-34a)-5-((G-52a)-3,5-F2) 246-248 100 6-213 Me Cl G-39b * 100 6-214 Me Cl G-65a 216-218 100 6-215 Et Cl G-39b * 95 6-216 Et Cl G-39b * 5 6-217 OEt Cl (G-31a)-3-((G-52a)-3,5-F2) 180-182 100 6-218 OEt Cl (G-31a)-3-CH2CH2CF3 125-127 100 6-219 Me Cl (G-34a)-5-CH2CH2CF3 * 50 6-220 Me Cl (G-30a)-5-CCl3 181-183 100 6-221 CF3 Cl (G-31a)-3-CH2CH2CF3 199-201 100 6-222 CF3 Cl (G-31a)-3-CH2CH2CH=CH2 161-163 100 6-223 Cl Cl (G-30a)-5-CH2CH2CF3 161-163 100 6-224 Cl Cl (G-30a)-5-CH2CH2CF3 136-138 25 6-225 Br Cl (G-30a)-5-CH2CH2CF3 164-166 100 6-226 Br Cl (G-30a)-5-CH2CH2CF3 114-116 10 6-227 Et Cl (G-30a)-5-CH2CH2CF3 117-119 80 6-228 OMe Cl (G-30a)-5-CH2CH2CF3 * 80 6-229 Br Cl (G-10a)-5-((G-52a)-3,5-F2) 241-243 100 6-230 OMe Cl (G-10a)-5-((G-52a)-3,5-F2) 202-204 100 6-231 Cl Cl (G-10a)-5-((G-52a)-3,5-F2) 259-261 100 6-232 OMe Cl (G-30a)-5-((G-52a)-3-OMe-5-F) * 100 6-233 OMe Cl (G-30a)-5-((G-52a)-3-OMe-5-F) * 60 6-234 cPr Cl (G-31a)-3-((G-52a)-3,5-F2) 182-184 65 6-235 cPr Cl (G-31a)-3-CH2CH2CF3 173-175 65 6-236 Et Cl (G-8a)-5-(G-1a) 149-151 100 6-237 OMe Cl (G-31a)-3-CH2CH2CF3 126-128 80 6-238 OMe Cl (G-31a)-3-CH2CH2CH=CH, 2　 159-161 80 6-239 Me Cl (G-31a)-3-(E-6a) 149-151 100 6-240 Me Cl (G-30a)-5-CH2CH2CH=CH 2　 144-146 100 6-241 Br Cl (G-30a)-5-CH2CH2CH=CH 2　 151-153 100 6-242 OMe Cl (G-30a)-5-CH2CH2CH=CH 2　 117-119 75 6-243 Et Cl (G-30a)-5-CH2CH2CH=CH 2　* 90 6-244 Me Cl (G-34a)-5-(D-42a) * 100 6-245 Me Cl (G-34a)-5-(D-43a) 197-199 100 6-246 Me Cl (G-34a)-5-(D-44a) 179-181 100 6-247 Me Cl (G-34a)-5-(D-45a) 186-188 100 6-248 Me Cl G-39c 119-121 70 6-249 OMe Cl G-39c 116-118 60 6-250 Br Cl G-39c 154-156 100 6-251 Br Cl G-39c 146-148 20 6-252 Me Cl (G-34a)-5-(D-46a) * 100 6-253 Me Cl (G-34a)-5-(D-47a) 194-196 100 6-254 OMe Cl (G-8a)-5-(G-1a) 200-202 100 6-255 Br Cl (G-31a)-3-((G-52a)-3,5-F2) * 0 6-256 Cl Cl (G-30a)-5-CH2CH2CH=CH2 * 50 6-257 Br Cl (G-30a)-5-CH2CH2CH=CH2 * 20 6-258 Me Cl (G-34a)-5-(D-48a) 179-181 100 6-259 Me Cl (G-34a)-5-(E-61a) 209-211 100 6-260 Me Cl (G-34a)-5-(D-49a) 186-188 100 6-261 Me Cl (G-30a)-5-CH(CH3)(nPr) 117-119 100 6-262 Me Cl (G-30a)-5-iPen 146-148 100 6-263 OMe Cl (G-30a)-5-((G-52a)-3,5-F2) 192-194 100 6-264 Cl Cl (G-31a)-3-CH2CH2CH=CH2 156-158 90 6-265 Br Cl (G-31a)-3-CH2CH2CH=CH2 141-143 85 6-266 OMe Cl G-50b * 100 6-267 OMe Cl G-51c * 100 6-268 Me Cl G-50b * 100 6-269 Me Cl G-51c 159-161 100 6-270 OMe Cl (G-30a)-5-(G-1a) 196-198 100 6-271 Me Cl (G-34a)-5-CH(CH3)(CH2CH=CH2) 154-156 100 6-272 Me Cl (G-34a)-5-CH2CH(CH3)(CH=CH2) 161-163 100 6-273 Me Cl (G-34a)-5-CH(CH3)(CH2CH3) 164-166 100 6-274 Me Cl (G-34a)-5-CH=CHCH=CH2 (E) 186-184 100 6-275 Me Cl (G-34a)-5-CH(CH3)(CH2CF3) 174-176 100 6-276 Me Cl (G-34a)-5-CH2CH=CH2 146-148 80 6-277 Me Cl (G-34a)-5-CH(CH3)(CH=CH2) 124-126 100 6-278 Me Cl (G-34a)-5-CH2CH2CH, 3　152-154 100 6-279 Me Cl (G-34a)-5-CH(CH3)(nPr) 152-154 100 6-280 Me Cl (G-34a)-5-CH2CH(CH3)(CH2CH3) 167-169 100 6-281 Me Cl (G-34a)-5-iPen 152-154 100 6-282 SEt Cl (G-8a)-5-((G-52a)-3,5-F2) * 60 6-283 Me Cl (G-34a)-5-CH2CH2CH2CH3 127-129 100 6-284 Me Cl (G-34a)-5-CH2CH2CH2CF3 154-156 100 6-285 Me Cl (G-34a)-5-CH2CH2CHF2 149-151 100 6-286 Me Cl (G-34a)-5-CH2CH(CF3)(CF3) 159-161 100 6-287 Me Cl (G-34a)-5-CH2CF3 177-179 100 6-288 Me Cl (G-34a)-5-CH(CH3)(OMe) 176-178 100 6-289 Me Cl (G-34a)-5-(E-38a) 209-211 100 6-290 Me Cl (G-34a)-5-CH=CHCH3 (E) * 100 6-291 Me Cl (G-34a)-5-C(CH3)=CHCH3 (E) 187-189 100 6-292 OEt Cl (G-31a)-3-CH2CH2CH=CH 2　111-113 90 6-293 OEt Cl (G-31a)-3-((G-55a)-5-F) 227-229 100 6-294 OEt Cl (G-31a)-3-nPr 97-99 80 6-295 OEt Cl (G-31a)-3-(E-38a) 174-176 100 6-296 Me Cl (G-34a)-5-CH2CH2CF3 159-161 100 6-297 iPr Cl (G-31a)-3-((G-52a)-3,5-F2) 187-189 100 6-298 OEt Cl (G-31a)-3-((G-52a)-5-Cl) 211-213 100 6-299 OEt Cl (G-31a)-3-((G-52a)-3-F) 174-176 100 6-300 OEt Cl (G-31a)-3-((G-52a)-5-F) 202-204 85 6-301 OEt Cl (G-31a)-3-((G-52a)-3,5-Cl2) 184-186 95 6-302 OEt Cl (G-31a)-3-((G-55a)-5-Cl) 236-238 100 6-303 OEt Cl (G-31a)-3-(G-55a) 207-209 100 6-304 OEt Cl (G-31a)-3-(G-58a) 186-188 100 6-305 OEt Cl (G-31a)-3-(Ph-2,4-F2) 199-201 100 6-306 CH=CH2 Cl (G-31a)-3-((G-52a)-3,5-F2) 196-198 100 6-307 Me Cl (G-34a)-5-CH(CH2CH3)(CH2CH3) 130-132 100 6-308 Me Cl (G-34a)-5-C(CH3)(CH3)(CH2CH3) 152-154 100 6-309 Me Cl (G-34a)-5-CH2CH2tBu 166-168 100 6-310 OiPr Cl (G-31a)-3-((G-52a)-3,5-F2) 137-139 100 6-311 OnPr Cl (G-31a)-3-((G-52a)-3,5-F2) 122-124 100 6-312 Me Cl (G-34a)-5-CH=CHCl (Z) 196-198 100 6-313 Me Cl (G-34a)-5-((D-50a)-2-Br) 167-169 100 6-314 Me Cl (G-34a)-5-(D-50a) 206-208 100 6-315 Me Cl (G-34a)-5-CH2CH2CF=CF2 129-131 100 6-316 Me Cl (G-34a)-5-CH(CH3)(OCOCH3) 197-199 100 6-317 Me Me (G-31a)-3-CH(CH3)(CH=CH2) 133-135 95 6-318 iPr Cl (G-31a)-3-CH(CH3)(CH=CH2) 148-150 100 6-319 iPr Cl (G-31a)-3-CH(CH3)(CH2CH3) 159-161 100 6-320 CH=CH2 Cl (G-31a)-3-CH(CH3)(CH2CH3) 132-134 100 6-321 OEt Me (G-31a)-3-((G-52a)-3,5-F2) 159-161 100 6-322 OEt Me (G-31a)-3-CH(CH3)(CH2CH3) 110-112 100 6-323 Me Me (G-31a)-3-CH(CH3)(CH2CH3) 168-170 100 6-324 CH=CH2 Cl (G-31a)-3-CH(CH3)(CH=CH2) 102-104 90 6-325 Me Cl (G-34a)-5-CH2CH=CHCH3 (E) 171-173 100 6-326 Me Cl (G-34a)-5-CH2N(CH3)(CH2CH3) 176-178 100 6-327 Me Cl (G-34a)-5-CH2CH2N(CH3)(CH3) 134-136 100 6-328 Me Cl (G-34a)-5-CH2(E-45a) 214-216 100 6-329 Me Cl (G-34a)-5-CH2(E-12a) 182-184 100 6-330 Me Cl (G-34a)-5-CH2CH2C(O)CH3 157-159 70 6-331 Me Cl (G-34a)-5-C(O)CH3 191-193 100 6-332 Me Cl (G-34a)-5-C(O)nPr, 　74-76 100 6-333 Me Cl (G-34a)-5-C(CH3)=CHCH2CH3 (E) 157-159 100 6-334 Me Cl (G-34a)-5-CH(CH3)NHC(O)CH3 222-224 100 6-335 Me Cl (G-34a)-5-CH2C(O)OCH3 186-188 100 6-336 Me Cl (G-34a)-5-(E-89a) 159-161 100 6-337 Me Cl (G-34a)-5-(E-90a) 181-193 100 6-338 OiPr Cl (G-31a)-3-CH(CH3)(CH2CH3) 134-136 100 6-339 OnPr Cl (G-31a)-3-CH(CH3)(CH2CH3) 105-107 90 6-340 Me Cl (G-34a)-5-CH2CH2CH=CH 2　 146-147 100 6-341 Me Cl (G-34a)-5-CH=CHCH2CH3 (E) 160-161 100 6-342 Me Cl (G-34a)-5-CH2OCH2CH 3　 180-181 100 6-343 Me Cl (G-34a)-5-CH2CH2OCH3 161-162 100 6-344 Me Cl (G-34a)-5-CH(CH3)(CF3) 154-155 100 6-345 Me Cl (G-34a)-5-CH2CH2cPr 153-154 100 6-346 iPr Cl (G-34a)-5-CH2CH=CH 2　165-167 100 6-347 iPr Cl (G-34a)-5-CH=CHCH3 (E) 170-172 100 6-348 nPr Cl (G-31a)-3-((G-52a)-3,5-F2) 144-146 80 6-349 CH2OCH3 Cl (G-31a)-3-((G-52a)-3,5-F2) 206-208 80 6-350 nPr Cl (G-31a)-3-CH(CH3)(CH2CH3) 111-113 100 6-351 nPr Cl (G-31a)-3-CH(CH3)(CH=CH2) 110-112 80 6-352 CH2OCH3 Cl (G-31a)-3-CH(CH3)(CH2CH3) 135-137 100 6-353 CH2OCH3 Cl (G-31a)-3-CH(CH3)(CH=CH2) 140-142 90 6-354 OnPr Cl (G-31a)-3-CH(CH3)(nPr) 80-82 100 6-355 NMe2 Cl (G-31a)-3-((G-52a)-3,5-F2) 164-166 100 6-356 SEt Cl (G-31a)-3-((G-52a)-3,5-F2) 149-151 100 6-357 OCH2CF3 Cl (G-31a)-3-((G-52a)-3,5-F2) 156-158 80 6-358 S(O)2Et Cl (G-31a)-3-((G-52a)-3,5-F2) 256-258 100 6-359 OnPr Cl (G-31a)-3-((G-52a)-5-Cl) 182-184 100 6-360 CH=CH2 Cl (G-31a)-3-CH(CH3)(nPr) 110-112 100 6-361 iPr Cl (G-31a)-3-CH(CH3)(nPr) 162-164 100 6-362 nPr Cl (G-31a)-3-CH(CH3)(nPr) 95-97 100 6-363 CH2OCH3 Cl (G-31a)-3-CH(CH3)(nPr) 104-106 100 6-364 Cl Cl (G-31a)-3-CH(CH3)(CH2CH3) 160-162 100 6-365 Cl Cl (G-31a)-3-CH(CH3)(CH=CH2) 184-186 100 6-366 Cl Cl (G-31a)-3-CH(CH3)(nPr) 158-160 100 6-367 OEt Cl(G-34a)-5-CH=CHCH2CH3(E) * 100 6-368 OEt Cl(G-34a)-5-CH(CH3)NHC(O)CH, 3　202-204 100 6-369 OEt Cl (G-34a)-5-(D-44a) * 100 6-370 OEt Cl (G-34a)-5-(D-42a) 122-124 100 6-371 OEt Cl (G-34a)-5-(D-46a) 166-168 100 6-372 OEt Cl (G-34a)-5-C(CH3)=CHCH3 (E) * 100 6-373 OEt Cl (G-34a)-5-(D-46a) 127-129 80 6-374 OEt Cl (G-31a)-3-(D-50a) 164-166 90 6-375 OEt Cl (G-31a)-3-cPen 131-133 80 6-376 OEt Cl (G-31a)-3-(D-47a) 159-161 100 6-377 OEt Cl (G-31a)-3-CH(CH3)(nPr) 84-86 0 6-378 OEt Cl (G-31a)-3-CH(CH3)(nPr) 106-108 95 6-379 Me Cl (G-34a)-5-C(CH3)=CH2 191-192 100 6-380 Me Cl (G-34a)-5-CH2CH2C(CH3)=CH2 130-131 100 6-381 Me Cl (G-34a)-5-CH(CH3)iPr 170-171 100 6-382 Me Cl (G-34a)-5-CH2CH2C≡CH 173-174 100 6-383 OEt Cl (G-31a)-3-CH(CH3)(CH2CH=CH2) 94-96 100 6-384 OiPr Cl (G-31a)-3-CH(CH3)(nPr) 109-111 100 6-385 NMe2 Cl (G-31a)-3-CH(CH3)(CH2CH3) 157-159 80 6-386 SEt Cl (G-31a)-3-CH(CH3)(CH2CH3) 117-119 80 6-387 OnPr Cl(G-31a)-3-(Ph-2,4-F2) 164-166 100 6-388 OnPr Cl (G-31a)-3-((G-52a)-5-F) 171-173 100 6-389 OnPr Cl (G-31a)-3-((G-52a)-3-F) * 100 6-390 NMe2 Cl (G-31a)-3-CH(CH3)(CH=CH2) 137-139 70 6-391 SEt Cl (G-31a)-3-CH(CH3)(CH=CH2) 122-124 100 6-392 NMe2 Cl (G-31a)-3-CH(CH3)(nPr) 161-163 100 6-393 SEt Cl (G-31a)-3-CH(CH3)(nPr) 94-96 80 6-394 OCH2CF3 Cl (G-31a)-3-CH(CH3)(nPr) 124-126 100 6-395 OCH2CF3 Cl (G-31a)-3-CH(CH3)(nPr) 142-144 100 6-396 OCH2CF3 Cl (G-31a)-3-CH(CH3)(CH=CH2) 144-146 100 6-397 OCH2CF3 Cl (G-31a)-3-CH2CH2CH=CH 2　120-122 100 6-398 OiPr Cl (G-31a)-3-CH(CH3)(CH=CH2) 125-127 100 6-399 OnPr Cl (G-31a)-3-CH(CH3)(CH=CH2) 102-104 70 6-400 OEt Cl (G-34a)-5-CH(CH3)(nPr) * 100 6-401 OEt Cl (G-34a)-5-CH(CH3)(CH2CH3) * 100 6-402 OEt Cl (G-34a)-5-CH(CH3)(CH2CH=CH2) * 100 6-403 OEt Cl (G-34a)-5-CH(CH3)(CH=CH2) * 100 6-404 OEt Cl (G-34a)-5-C(CH3)=CH2 146-148 100 6-405 Me Cl (G-31a)-3-CH(CH3)(CH2CH3) 177-179 100 6-406 OEt Cl (G-31a)-3-CH(CH3)(CH2CH3) 121-123 90 6-407 OMe Cl (G-31a)-3-CH(CH3)(CH2CH3) 151-153 100 6-408 OEt Cl (G-31a)-3-CH(CH3)(CH=CH2) 131-133 100 6-409 OMe Cl (G-31a)-3-CH(CH3)(CH=CH2) 112-114 90 6-410 Me Cl (G-31a)-3-C(CH3)=CH2 169-171 80 6-411 OEt Cl (G-31a)-3-C(CH3)=CH2 141-143 75 6-412 OMe Cl (G-31a)-3-C(CH3)=CH2 149-151 85 6-413 OEt Cl (G-34a)-5-CH(CH3)(CH2CF3) * 100 6-414 OEt OMe (G-31a)-3-((G-52a)-3,5-F2) 172 - 174 100 6-415 OMe Cl (G-31a)-3-((G-52a)-3-F) * 90 6-416 OMe Cl (G-31a)-3-((G-52a)-5-F) 227 - 229 100 6-417 OMe Cl (G-31a)-3-((G-52a)-5-Cl) 198 - 200 80 6-418 Cl Cl (G-31a)-3-((G-52a)-5-F) 243 - 245 70 6-419 OEt Cl (G-31a)-3-CH(CH3)(nPr) * 100 6-420 OEt Cl (G-31a)-3-CH(CH3)(CH=CH2) 109 - 111 100 6-421 Me Cl (G-31a)-3-CH(CH3)(nPr) 142 - 144 100 ――――――――――――――――――――――――――――――――― [Table 8], ―――――――――――――――――――――――――――――――――― No. R 5 m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 7-001 C(O)NH((G-52a)-5-F) 209 - 211 100 ―――――――――――――――――――――――――――――――――― [Table 9] ―――――――――――――――――――――――――――――――――― No. Z 1a R 1aa R 1ab R 5m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 8-001 Me H Et C(O)NH((G-52a)-5-F) 139-141 80 8-002 tBu Me H C(O)NH((G-52a)-5-F) * 70 8-003 Me Et H C(O)NH((G-52a)-5-Cl) 192-194 100 8-004 Me Et H C(O)NH((G-55a)-5-F) 201-203 100 8-005 Me Et H C(O)NH((G-55a)-5-Cl) 221-223 100 8-006 Me Et H C(O)NH((G-58a)-5-Cl) 242-244 100 8-007 Me Me Me C(O)NH((G-52a)-5-F) 247-249 100 8-008 Me OMe H C(O)NH((G-55a)-5-F) 231-233 100 8-009 Me Br H C(O)NH((G-55a)-5-F) 252-254 100 8-010 Me Br H C(O)NH((G-52a)-5-F) 234-236 85 8-011 Me OMe H C(O)NH((G-52a)-5-F) * 100 8-012 Me H H C(O)NH((G-52a)-5-F) 198-200 100 8-013 Me OEt Cl C(O)NH((G-55a)-5-F) 206-208 100 8-014 Me Me Me C(O)NH((G-55a)-5-F) * 100 8-015 Me OEt Cl C(O)NH((G-52a)-5-F) 167-169 80 ―――――――――――――――――――――――――――――――――― [Table 10] ―――――――――――――――――――――――――――――――――― No. Z 1a R 1aa R 1ab R 5m.p. (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 9-001 Me H Et (G-8a)-5-((G-52a)-3,5-F2) 222-224 100 9-002 Me H Et (G-31a)-3-((G-52a)-3,5-F2) 196-198 0 9-003 Me H Et (G-31a)-3-((G-52a)-3,5-F2) 244-246 100 9-004 tBu Me H (G-31a)-3-((G-52a)-3,5-F2) 224-225 100 9-005 Me OMe H (G-8a)-5-((G-52a)-3,5-F2) 171-173 50 9-006 Me H Me (G-31a)-3-((G-52a)-3,5-F2) 191-193 100 9-007 Me Me Me (G-31a)-3-((G-52a)-3,5-F2) 192-194 100 9-008 Me Me Me (G-31a)-3-CH2CH2CF3 147-149 100 9-009 Me Me Me (G-31a)-3-CH2CH2CH=CH2 129-131 100 9-010 Me Me Me (G-8a)-5-((G-52a)-3,5-F2) 192-193 100 9-011 Me Me Me (G-8a)-5-((G-52a)-3,5-F2) * 30 9-012 Me Me Me (G-30a)-5-CH2CH2CF3 156-158 85 9-013 Me H Et (G-31a)-3-CH9-017 Me Me Me (G-10a)-5-((G-52a)-3,5-F2) 221-223 100 9-018 Me Me Me G-50b * 100 9-019 Me Me Me G-51c * 100 9-020 Me H OMe (G-31a)-3-((G-52a)-3,5-F2) 198-200 60 9-021 Me OEt Me (G-31a)-3-((G-52a)-3,5-F2) 204-206 100 9-022 Me Et Et (G-31a)-3-((G-52a)-3,5-F2) 172-174 100 9-023 Me OEt Me (G-31a)-3-CH(CH3)(CH2CH3) * 100 9-024 Me Et Et (G-31a)-3-CH(CH3)(nPr) * 100 9-025 Me H OMe (G-31a)-3-CH(CH3)(CH2CH3) 137-139 100 9-026 Me Me Me (G-34a)-5-C(CH3)=CHCH2CH3 (E) * 100 9-027 Me Me Me (G-34a)-5-CH(CH3)NHC(O)CH3 174-176 100 9-028 Me Me Me (G-34a)-5-CH2C(O)OCH3 * 100 9-029 Me Me Me (G-34a)-5-(D-44a) 86-88 100 9-030 Me Me Me (G-34a)-5-(D-42a) * 100 9-031 Me Me Me (G-34a)-5-(D-46a) * 100 9-032 Me Me Me (G-34a)-5-C(CH3)=CHCH3 (E) 151-153 100 9-033 Me Me Me (G-31a)-3-CH(CH3)(CH2CH=CH2) * 100 9-034 Me Me Me(G-31a)-3-(D-44a) 209-211 100 9-035 Me Et Et (G-31a)-3-CH(CH3)(nPr) * 100 9-036 Me OEt Me (G-31a)-3-CH(CH3)(nPr) * 100 9-037 Me OnPr Me (G-31a)-3-((G-52a)-3,5-F2) 134-136 100 9-038 Me Et Et (G-31a)-3-CH(CH3)(CH=CH2) * 100 9-039 Me OEt Me (G-31a)-3-CH(CH3)(CH=CH2) * 100 9-040 Me Me Me (G-31a)-3-(D-46a) 137-139 100 9-041 Me Me Me (G-31a)-3-(D-50a) 186-188 100 9-042 Me Me Me (G-31a)-3-cPen 154-156 100 9-043 Me Me Me (G-31a)-3-(D-47a) 147-149 100 9-044 Me Me Me (G-31a)-3-CH(CH3)(nPr) 131-133 100 9-045 Me Me Me (G-34a)-5-CH(CH3)(nPr) * 100 9-046 Me Me Me (G-34a)-5-CH(CH3)(CH2CH3) * 100 9-047 Me Me Me (G-34a)-5-CH(CH3)(CH2CH=CH2) * 100 9-048 Me Me Me (G-34a)-5-C(CH3)=CH2 * 100 9-049 Me Me Me (G-34a)-5-C(CH3)=CH2 * 100 9-050 Me Me Me (G-31a)-3-CH(CH3)(CH2CH3) 146-148 100 9-051 Me Me Me (G-31a)-3-CH(CH3)(CH=CH2) 146-148100 9-052 Me Me Me (G-31a)-3-C(CH3)=CH2 176-178 100 9-053 Me Me Me (G-34a)-5-CH(CH3)(CH2CF3) * 100 9-054 Me Me Me (G-31a)-3-((G-52a)-3-F) * 100 9-055 Me Me Me (G-31a)-3-((G-52a)-5-F) 230-232 100 9-056 Me Me Me (G-31a)-3-((G-52a)-5-Cl) 240-242 100 9-057 Me H CF3 (G-31a)-3-((G-52a)-3,5-F2) 254-256 100 9-058 Me H OMe (G-31a)-3-CH(CH3)(CH=CH2) 139-141 100 9-059 Me H OMe (G-31a)-3-CH(CH3)(nPr) 109-111 100 ―――――――――――――――――――――――――――――――――― [Table 11] ―――――――――――――――――――――――――――――――――― No. Q R 5Melting point (°C) A rate (%) ―――――――――――――――――――――――――――――――――― 10-001 S (G-31a)-3-((G-52a)-3,5-F2) 234-236 85 10-002 NOMe (G-31a)-3-((G-52a)-3,5-F2) 204-206 95 10-003 NOH (G-31a)-3-((G-52a)-3,5-F2) 211-213 95 10-004 S NHCH2Ph 179-181 0 10-005 S NHCH2CH2CH2SMe 182-184 0 10-006 S NHC(O)Ph 111-113 100 ―――――――――――――――――――――――――――――――――― [Table 12] ――――――――――――――――――――――――――― No. R 1aa R 1ab R 2acmp (℃) ―――――――――――――――――――――――― 11-001 Cl H Cl * 11-002 Me H Cl 121-123 11-003 Et H Cl * 11-004 OMe H Cl 100-102 11-005 OEt H Cl 101-103 11-006 Me Me Cl 141-143 11-007 Br H Cl * 11-008 SEt H Cl 119-121 11-009 NMe2 H Cl 139-141 11-010 OiPr H Cl 86-88 11-011 OnPr H Cl * 11-012 OCH2CF3 H Cl * 11-013 OEt Me Cl 124-126 11-014 OnPr Me Cl * 11-015 Et Et Cl 127-129 11-016 Me H Me 100-102 ---------------------------------------------------------------- Among the compounds and production intermediates of the present invention shown in Tables 2 to 12, those compounds for which no melting point is given are １ The H-NMR data are shown in Table 13. The following data were measured in deuterated chloroform, with "#1" indicating that the measurement was performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL), and similarly, "#2" indicating that the measurement was performed at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).

[0451] [Table 13] ------------------------------------------------------------------ No. 1H-NMR (CDCl3, Me4Si) ―――――――――――――――――――――――――――――――――― 1-004(#1): δ8.56-8.38 (m, 2H), 7.98-7.87 (m, 1H), 7.58 (s, 1H), 7.44 (t, 1H, J=8.2Hz), 7.16 (d, 1H, J=3.7Hz), 7.09-6.94 (m, 3H), 6.77 (d, 1H, J=7.8Hz), 3.98 (s, 3H), 2.59 (s, 3H)。 1-007(#2): δ13.12 (d, 1H, J=10.8Hz), 8.00-6.50 (m, 11H), 3.93 (s, 3H)。 1-011(#2): δ8.60-6.50 (m, 11H), 4.00-3.80 (m, 3H), 2.42 (s, 3H)。 1-013(#2): δ8.60-6.40 (m, 11H), 4.00-3.90 (m, 3H)。 2-028(#1): δ12.95 (d, 1H, J=12.3Hz), 7.70-6.90 (m, 5H), 6.50 (s, 1H), 3.90-3.70 (m, 3H), 2.20-2.10 (m, 3H), 1.35 (s, 9H)。 2-029(#1): δ13.10-12.80 (m, 1H), 7.75-6.30 (m, 6H), 3.92-3.70 (m, 3H), 2.35-1.96 (m, 4H), 1.40-0.93 (m, 4H)。 2-030(#1): δ13.20-12.94 (m, 3H), 8.60-6.66 (m, 7H), 3.98-3.79 (m, 3H), 2.20-2.00 (m, 3H)。 2-031(#1): δ13.23 (d, 1H, J=11.1Hz), 8.00-6.50 (m, 6H), 3.90-3.80 (m, 3H), 2.69 (s, 3H), 2.20-2.00 (m, 3H)。2-032(#1): δ14.35-14.08 (m, 1H), 7.49 (t, 1H, J=7.7Hz), 7.40 (s, 1H), 7.31 (d, 1H, J=10.6Hz), 6.98 (d, 1H, J=7.4Hz), 6.87 (d, 1H, J=7.7Hz), 6.50(s, 1H), 3.85 (s, 3H), 2.76 (s, 3H), 2.51 (s, 3H), 2.16 (s, 3H)。 2-033(#1): δ12.96-12.69 (m, 1H), 7.77 (t, 1H, J=7.7Hz), 7.54-7.38 (m, 3H), 7.29-7.23 (m, 1H), 6.51-6.47 (m, 1H), 3.86 (s, 3H), 2.52 (s, 3H), 2.16 (s, 3H)。 2-034(#1): δ13.20-13.00 (m, 1H), 7.70-6.60 (m, 6H), 4.31 (s, 3H), 3.85 (s, 3H), 2.40-2.00 (m, 6H)。 2-035(#1): δ8.53-8.32 (m, 2H), 7.45 (t, 1H, J=7.7Hz), 7.38 (s, 1H), 7.10 (d, 1H, J=8.2Hz), 6.80 (d, 1H, J=7.7Hz), 6.48 (s, 1H), 3.93 (s, 3H), 2.56-2.44 (m, 5H), 1.04 (t, 3H, J=7.4Hz)。 2-036(#1): δ12.69-12.53 (m, 1H), 7.73-7.68 (m, 1H), 7.58 (t, 1H, J=7.4Hz), 7.41 (s, 1H), 7.34 (d, 1H, J=11.0Hz), 7.06-7.01 (m, 1H), 6.51-6.46 (m, 1H), 4.05 (s, 3H), 3.85 (s, 3H), 2.54-2.46 (m, 6H) 2.16 (s, 3H)。 2-037(#1): δ8.43(s, 1H), 7.60-6.40 (m, 5H), 3.90 (s, 3H), 3.90-3.70 (m, 2H), 3.35 (s, 3H), 1.90-1.50 (m, 5H), 1.00 (t, 3H, J=7.5Hz)。2-038(#2): δ8.64-6.38 (m, 7H), 4.15-2.95 (m, 4H), 2.38-2.00 (m, 3H), 1.42-1.11 (m, 6H)。 2-039(#1): δ13.01(d, 1H, J=10.8Hz), 7.70-6.90 (m, 5H), 6.54 (s, 1H), 3.86 (s, 3H), 2.72 (d, 2H, J=6.8Hz), 2.20-1.50 (m, 4H), 0.99 (d, 6H, J=4.8Hz)。 2-040(#2): δ13.22-12.91 (m, 1H), 8.59-6.30 (m, 6H), 4.00-3.00 (m, 4H), 2.38-2.00 (m, 3H), 1.42-1.05 (m, 6H)。 2-041(#1): δ13.00-6.36 (m, 6H), 3.97-3.75 (m, 3H), 2.61-2.41 (m, 3H), 2.29-2.02 (m, 3H)。 2-042(#1): δ14.30-14.08 (m, 1H), 8.60-6.32 (m, 6H), 4.00-3.69 (m, 3H), 3.11-0.70 (m, 13H)。 2-043(#2): δ8.60-8.32 (m, 1H), 7.70-6.70 (m, 6H), 4.65 (s, 2H), 4.19-3.67 (m, 3H), 2.30-1.87 (m, 3H)。 2-044(#2): δ13.35-6.40 (m, 7H), 4.82-4.44 (m, 2H), 4.02-3.30 (m, 6H), 2.25-1.91 (m, 3H)。 3-009(#1): δ13.01-12.70 (m, 1H), 8.02-6.31 (m, 7H), 4.05-3.72 (m, 3H), 2.62-2.31 (m, 3H)。 4-001(#1): δ13.20-6.80 (m, 11H), 4.00-3.90 (m, 3H)。 5-082(#2): δ12.93 (d, 1H, J=11.6Hz), 7.70-6.90 (m, 10H), 3.79 (s, 3H), 3.44 (s, 3H), 2.10-2.00 (m, 3H)。5-083(#1): δ13.40-6.80 (m, 7H), 4.00-3.70 (m, 6H), 2.20-2.00 (m, 3H)。 5-084(#1): δ13.50-6.90 (m, 7H), 4.00-1.00 (m, 9H)。 5-085(#2): δ13.50-6.90 (m, 10H), 3.98-3.75 (m, 3H), 2.21-1.95 (m, 3H)。 5-086(#1): δ9.00-6.50 (m, 9H), 4.00-1.50 (m, 9H)。 5-087(#1): δ13.22 (d, 1H, J=11.0Hz), 9.10-6.00 (m, 12H), 3.85 (s, 3H), 2.20-2.00 (m, 3H)。 5-088(#1): δ13.40-6.50 (m, 10H), 4.00-3.70 (m, 3H), 2.30-2.00 (m, 3H)。 5-089(#1): δ13.06 (d, 1H, J=11.0Hz), 7.60-6.80 (m, 8H), 3.80 (s, 3H), 3.39 (s, 3H), 2.08 (s, 3H)。 5-090(#1): δ9.10-6.80 (m, 10H), 3.87 (s, 3H), 2.10 (s, 3H)。 5-091(#1): δ12.94(d, 1H, J=11.4Hz), 7.60-6.90 (m, 9H), 3.80 (s, 3H), 3.41 (s, 3H), 2.07 (s, 3H)。 5-092(#1): δ13.27(d, 1H, J=11.7Hz), 7.70-6.90 (m, 7H), 3.85 (s, 3H), 2.20-2.00 (m, 3H)。 5-093(#1): δ13.40-6.90(m, 9H), 4.00-3.80 (m, 3H), 2.20-2.00 (m, 3H)。 5-094(#1): δ13.32(d, 1H, J=12.0Hz), 10.00-6.90 (m, 8H), 3.86 (s, 3H), 2.17 (s, 3H)。 5-095(#1): δ13.61-13.20 (m, 1H), 9.54-8.73 (m, 2H), 7.72-6.78 (m, 6H), 3.85 (s, 3H), 2.15 (s, 3H)。5-096(#2): δ13.33 (m, 1H), 9.92-6.74 (m, 8H), 3.89 (s, 3H), 2.23 (s, 3H)。 5-097(#2): δ13.27 (m, 1H), 9.45-6.99 (m, 8H), 3.87 (s, 3H), 2.37 (s, 3H), 2.17 (s, 3H)。 5-098(#1): δ13.39 (m, 1H), 10.00-6.93 (m, 9H), 3.84 (s, 3H), 2.16 (s, 3H)。 5-099(#1): δ11.58-11.32 (m, 1H), 7.65-6.32 (m, 10H), 3.96-3.66 (m, 3H), 2.26-2.00 (m, 3H)。 5-100(#2): δ13.28 (d, 1H, J=11.2 Hz), 9.23 (s, 1H), 8.33-6.87 (m, 7H), 3.84 (s, 3H), 2.34 (s, 3H), 2.16 (s, 3H)。 5-103(#2): δ13.60 (m, 1H), 10.64-10.49 (m, 1H), 8.46-6.73 (m, 10H), 3.85 (m, 3H), 2.15 (m, 3H)。 5-104(#1): δ13.30 (m, 1H), 9.65 (s, 1H), 8.51-6.44 (m, 8H), 3.84 (s, 3H), 2.73-2.47 (m, 5H), 2.16 (s, 3H)。 5-107(#1): δ13.45 (m, 1H), 9.42-6.86 (m, 9H), 3.84 (s, 3H), 2.14 (s, 3H)。 5-109(#2): δ13.38 (m, 1H), 9.27 (s, 1H), 8.42-6.89 (m, 8H), 3.85 (s, 3H), 2.16 (s, 3H)。 5-110(#1): δ13.50-6.79(m, 7H), 4.03-3.61 (m, 3H), 2.32-2.00 (m, 9H)。 5-118(#1): δ9.61-6.62 (m, 9H), 3.91-3.78 (m, 6H), 2.10 (s, 3H)。5-119(#1): δ9.45-6.41 (m, 8H), 3.88 (s, 3H), 3.68 (s, 3H), 2.24 (s, 3H), 2.10 (s, 3H)。 5-120(#1): δ13.46 (d, J = 11.1 Hz, 1H), 10.50 (s, 1H), 8.22-6.91 (m, 10H), 3.86 (s, 3H), 2.15 (s, 3H)。 5-124(#1): δ13.26 (m, 1H), 9.20-6.86 (m, 8H), 3.85 (s, 3H), 2.83 (s, 3H), 2.01 (s, 3H)。 5-128(#1): δ13.50-6.05 (m, 8H), 3.82-3.70 (m, 3H), 2.90-2.80 (m, 3H), 2.32-2.22 (m, 3H), 2.21-2.08 (m, 3H)。 5-131(#1): δ13.18 (d, J = 10.6 Hz, 1H), 7.69-6.91 (m, 6H), 4.15-4.07 (m, 1H), 3.83 (s, 3H), 3.34-3.23 (m, 1H), 2.13 (s, 3H), 1.94-1.80 (m, 1H), 1.52-1.18 (m, 1H)。 5-133(#2): δ13.25 (d, J = 28.6 Hz, 1H), 9.60 (d, J = 9.4 Hz, 1H), 7.93-6.86 (m, 8H), 3.85 (s, 3H), 2.15 (s, 3H)。 5-134(#2): δ13.34 (m, 1H), 9.19-6.87 (m, 9H), 3.47 (s, 3H), 2.14 (s, 3H)。 6-082(#1): δ13.27 (d, 1H, J=12.0Hz), 7.60-6.50 (m, 6H), 3.90-3.70 (m, 3H), 2.20-2.00 (m, 6H)。 6-083(#1): δ10.90-6.60 (m, 12H), 4.00-3.68 (m, 3H), 2.35-2.02 (m, 3H)。 6-084(#1): δ14.20-6.80 (m, 10H), 4.00-3.70 (m, 3H), 2.70-1.00 (m, 3H)。6-085(#1): δ8.54-8.32 (m, 2H), 7.55 (s, 1H), 7.48 (t, 1H, J=7.7Hz), 7.12 (d, 1H, J=7.7Hz), 6.81 (d, 1H, J=7.7Hz), 6.50 (m, 1H), 4.00 (s, 3H), 2.48 (s, 3H)。 6-086(#1): δ8.53-8.32 (m, 2H), 7.45 (t, 1H, J=7.7Hz), 7.38 (s, 1H), 7.10 (d, 1H, J=8.2Hz), 6.80 (d, 1H, J=7.7Hz), 6.48 (s, 1H), 3.93 (s, 3H), 2.56-2.44 (m, 5H), 1.04 (t, 3H, J=7.4Hz)。 6-087(#2): δ13.63-13.35 (m, 1H), 8.39-6.62 (m, 9H), 4.02-3.62 (m, 3H), 2.26-1.99 (m, 3H)。 6-088(#2): δ13.60-13.39 (m, 1H), 8.41-6.82 (m, 8H), 3.93-3.76 (m, 3H), 2.25-2.09 (m, 3H)。 6-089(#2): δ13.40-13.21 (m, 1H), 8.85-6.65 (m, 6H), 3.39-3.69 (m, 3H), 2.95-2.80 (m, 3H), 2.35-1.98 (m, 3H)。 6-090(#2): δ13.15-12.74 (m, 1H), 7.72-6.42 (m, 8H), 4.00-3.68 (m, 3H), 2.39-1.89 (m, 3H)。 6-091(#1): δ9.13-8.89 (m, 1H), 8.62-8.35 (m, 2H), 7.70-6.71 (m, 6H), 4.03-3.78 (m, 3H), 2.32-1.96 (m, 3H)。 6-092(#1): δ13.28-12.92 (m, 1H), 8.79-6.56 (m, 6H), 3.98-3.57 (m, 3H), 2.80-1.85 (m, 6H)。 6-093(#1): δ12.20-6.60 (m, 6H),4.01-3.52 (m, 3H), 2.75-0.70 (m, 19H)。6-094(#1): δ12.15-11.86 (m, 1H),7.70-6.82 (m, 5H), 3.94-3.64 (m, 3H), 2.72-0.70 (m, 16H)。 6-095(#1): δ8.71-8.57 (m, 1H), 8.43-6.87 (m, 5H), 4.00 (s, 3H), 2.48 (s, 3H)。 6-096(#1): δ8.86-8.76 (m, 1H), 8.62-6.88 (m, 7H), 3.99 (s, 3H)。 6-097(#1): δ13.66-13.50 (m, 1H), 7.69-7.61 (m, 2H), 7.54 (s, 1H), 7.43 (d, 1H, J=10.2Hz), 7.32-7.23 (m, 2H), 7.04 (d, 1H, J=7.7Hz), 6.64-6.59 (m, 1H), 3.92 (s, 3H)。 6-098(#1): δ15.10-14.94 (m, 1H), 8.60-8.56 (m, 1H), 7.56 (t, 1H, J=8.3Hz), 7.51-7.44 (m, 1H), 7.42 (s, 1H), 7.32 (d, 1H, J=9.7Hz), 7.05 (d, 1H, J=7.4Hz), 6.95 (d, 1H, J=7.88Hz), 3.87 (s, 3H), 2.81 (s, 3H), 2.18 (s, 3H)。 6-099(#2): δ15.05-14.90 (m, 1H), 7.68-7.66 (m, 1H), 7.57 (t, 1H, J=7.9Hz), 7.42 (s, 1H), 7.33 (d, 1H, J=9.7Hz), 7.25-7.22 (m, 1H), 7.07 (d, 1H, J=7.4Hz), 6.96 (d, 1H, J=7.88Hz), 6.64-6.61 (m, 1H), 3.87 (s, 3H), 2.86 (s, 3H), 2.18 (s, 3H)。6-100(#1): δ8.71-8.59 (m, 1H), 8.37 (d, 1H, J=12.3Hz), 7.54-7.38 (m, 2H), 7.19-7.13 (m, 1H), 6.90-6.83 (m, 1H), 4.60 (s, 2H), 3.91 (s, 3H), 3.48 (s, 3H), 2.08 (s, 3H)。 6-101(#1): δ8.69-8.57 (m, 1H), 8.35 (d, 1H, J=12.6Hz), 7.59 (s, 1H), 7.46 (t, 1H, J=7.7Hz), 7.02 (d, 1H, J=7.7Hz), 6.78 (d, 1H, J=7.7Hz), 3.97 (s, 3H), 2.76 (t, 2H, J=7.7Hz), 2.59 (s, 3H), 1.87-1.71 (m, 2H), 1.00 (t, 3H, J=7.4Hz)。 6-123(#1): δ9.10-8.99 (m, 1H), 8.57-8.53 (m, 1H), 8.35 (d, 1H, J=12.3Hz), 7.56 (t, 1H, J=7.4Hz), 7.50-7.40 (m, 1H), 7.32 (s, 1H), 7.20 (d, 1H, J=7.4Hz), 7.06 (d, 1H, J=7.4Hz), 3.77 (s, 3H), 3.75 (s, 3H)。 6-155(#1): δ13.47-13.32 (m, 1H), 7.65 (t, 1H, J=7.7Hz), 7.52 (s, 1H), 7.45 (s, 1H), 7.40 (d, 1H, J=10.6 Hz), 7.31 (d, 1H, J=7.4Hz), 7.27-7.22 (m, 1H), 3.97 (s, 3H), 3.19-3.11 (m, 2H), 2.81-2.62 (m, 2H)。 6-175(#2): δ12.43-12.02 (m, 1H), 8.15-6.85 (m, 5H), 4.00-3.58 (m, 3H), 2.82-1.62 (m, 9H)。6-179(#1): δ13.75-13.40 (m, 1H), 7.75-6.81 (m, 5H), 5.95-5.62 (m, 1H), 5.22-4.80 (m, 4H), 4.01-3.72 (m, 3H), 2.90-2.60 (m, 2H), 2.30-2.01 (m, 3H)。 6-182(#1): δ13.80-6.73 (m, 9H), 6.33-5.70 (m, 2H),4.33-3.62 (m, 3H), 2.55-2.00 (m, 3H)。 6-213(#1): δ12.93 (d, 1H, J=11.0Hz), 8.15 (s, 1H), 7.70-6.90 (m, 5H), 5.90-5.70 (m, 1H), 5.20-5.00 (m, 2H), 4.59 (t, 2H, J=6.9Hz), 3.95 (s, 3H), 2.83 (d, 2H, J=7.2Hz), 2.16 (s, 3H)。 6-215(#1): δ13.07-6.72 (m, 7H), 5.95-5.63 (m, 1H), 5.29-4.95 (m, 2H), 4.70-4.39 (m, 2H), 4.02-3.86 (m, 3H), 2.99-2.40 (m, 4H), 1.25-0.98 (m, 3H)。 6-216(#1): δ8.58-6.70 (m, 7H), 5.88-5.60 (m, 1H), 5.18-4.98 (m, 2H), 4.55-4.35 (m, 2H), 4.03-3.81 (m, 3H), 2.88-2.40 (m, 4H), 1.20-0.99 (m, 3H)。 6-219(#2): δ13.51 (m, 1H), 8.65-6.54 (m, 5H), 4.13-1.95 (m, 10H)。 6-228(#1): δ13.15 (d, 1H, J=11.1Hz), 8.82-6.87 (m, 5H), 3.92-2.65 (m, 10H)。 6-232(#1): δ13.45-13.09 (m, 1H), 8.65-6.82 (m, 7H), 4.60-3.53 (m, 8H), 1.72-1.35 (m, 3H)。6-233(#1): δ13.45-6.82 (m, 8H), 4.60-3.53 (m, 8H), 1.72-1.35 (m, 3H)。 6-243(#1): δ13.17 (d, 1H, J=10.6Hz), 7.90-6.82 (m, 5H), 5.94-5.05 (m, 3H), 3.85 (s, 3H), 3.14-1.02 (m, 9H)。 6-244(#1): δ13.45-13.00 (m, 1H), 8.10-6.82 (m, 6H), 4.31-3.71 (m, 5H), 2.73-1.95 (m, 7H)。δ8.72-6.70 (m, 6H), 5.99-5.62 (m, 1H), 5.25-4.92 (m, 2H), 4.29-3.72 (m, 3H), 3.21-2.89 (m, 2H), 2.76-2.43 (m, 2H)。 6-252(#1): δ13.53-12.88 (m, 1H), 7.75-6.82 (m, 6H), 4.02-3.70 (m, 3H), 2.75-1.40 (m, 11H)。 6-255(#1): δ9.00-6.80 (m, 8H), 4.32-3.72 (m, 3H)。 6-256(#1): δ13.48-6.45 (m, 6H), 6.02-3.61 (m, 6H), 3.22-2.50 (m, 4H)。 6-257(#1): δ8.72-6.70 (m, 6H), 5.99-5.62 (m, 1H), 5.25-4.92 (m, 2H), 4.29-3.72 (m, 3H), 3.21-2.89 (m, 2H), 2.76-2.43 (m, 2H)。 6-266(#1): δ13.78-13.30 (m, 1H), 7.86-7.02 (m, 5H), 5.22-4.95 (m, 2H), 3.87-3.60 (m, 6H), 3.12-2.72 (m, 2H)。 6-267(#1): δ13.78-13.25 (m, 1H), 7.80-7.11 (m, 5H), 5.20-4.89 (m, 2H), 3.90-3.61 (m, 6H), 3.15-2.79 (m, 2H)。6-268(#1): δ13.80-13.52 (m, 1H), 7.72-6.44 (m, 5H), 5.22-4.95 (m, 2H), 3.99-3.75 (m, 3H), 3.04-2.72 (m, 2H), 2.30-1.98 (m, 3H)。 6-282(#2): δ11.10-6.53 (m, 8H), 4.24-0.94 (m, 9H)。 6-290(#2): δ13.52-13.31 (m, 1H), 7.68-6.39 (m, 7H), 3.86 (s, 3H), 2.28-1.85 (m, 6H)。 6-367(#1): δ13.42-13.00 (m, 1H), 8.00-6.65 (m, 6H), 4.05-3.80 (m, 2H), 3.66 (s, 3H), 2.50-2.02 (m, 5H), 1.30-0.90 (m, 6H)。 6-369(#1): δ13.61-13.30 (m, 1H), 8.05-7.05 (m, 5H), 6.28-6.04 (m, 1H), 4.41-3.62 (m, 7H), 2.41-1.08 (m, 7H)。 6-372(#1): δ13.49-13.03 (m, 1H), 8.08-7.80 (m, 6H), 4.02-3.82 (m, 2H), 3.71 (s, 3H), 2.30-1.70 (m, 6H), 1.41-1.04 (m, 3H)。 6-389(#1): δ13.70-13.51 (m, 1H), 8.74-7.03 (m, 8H), 3.92-3.65 (m, 5H), 1.68-1.40 (m, 2H), 0.93-0.72 (m, 3H)。 6-400(#1): δ13.48-13.02 (m, 1H), 7.71-7.01 (m, 5H), 4.04-3.82 (m, 2H), 3.72 (s, 3H), 3.38-3.10 (m, 1H), 2.02-0.75 (m, 13H)。 6-401(#1): δ13.51-13.02 (m, 1H), 7.71-7.03 (m, 5H), 4.06-3.85 (m, 2H), 3.72 (s, 3H), 3.30-3.02 (m, 1H), 2.15-0.78 (m, 11H)。6-402(#1): δ13.49-13.03 (m, 1H), 7.73-7.04 (m, 5H), 5.89- 5.60 (m, 1H), 5.20-4.92 (m, 2H), 4.08-2.05 (m, 8H), 1.52-1.10 (m, 6H)。 6-403(#1): δ13.51-13.14 (m, 1H), 7.72-7.03 (m, 5H), 6.15-5.92 (m, 1H), 5.34-5.11 (m, 2H), 4.05-3.79 (m, 3H), 3.71 (s, 3H), 2.26-1.08 (m, 6H)。 6-413(#1): δ13.59-13.10 (m, 1H), 7.86-7.04 (m, 5H), 4.08-0.98 (m, 14H)。 6-415(#1): δ13.80-13.20 (m, 1H), 8.80-8.59 (m, 1H), 7.95-7.00 (m, 7H), 3.89-3.63 (m, 6H)。 6-419(#1): δ14,75-14.47 (m, 1H), 8.50-6.90 (m, 5H), 4.58-2.52 (m, 9H), 1.95-0.75 (m, 13H)。 8-002(#1): δ9.80-6.35 (m, 10H), 2.08-2.00 (m, 3H), 1.79-1.60 (m, 9H)。 8-011(#1): δ13.31 (d, 1H, J=10.6 Hz), 9.71 (s, 1H), 8.51-6.84 (m, 8H), 4.01-3.48 (m, 6H)。 8-014(#1): δ13.45-6.50 (m, 8H), 3.82-1.65 (m, 9H)。 9-011(#1): δ13.45-6.32 (m, 8H), 4.01-3.62 (m, 3H), 2.25-1.85 (m, 6H)。 9-015(#1): δ13.52-6.38 (m, 7H), 4.40-3.70 (m, 5H), 2.22-1.99 (m, 6H), 1.76-1.38 (m, 3H)。9-018(#1): δ13.82-13.58 (m, 1H), 7.70-6.35 (m, 4H), 5.28-5.05 (m, 2H), 3.90-3.69 (m, 3H), 3.08-2.72 (m, 2H), 2.22-1.95 (m, 6H)。 9-019(#1): δ13.59-13.30 (m, 1H), 7.70-6.75 (m, 4H), 5.10-4.85 (m, 2H), 3.79 (s, 3H), 3.18-2.72 (m, 2H), 2.22-1.91 (m, 6H)。 9-023(#2): δ13.85-13.29 (m, 1H), 7.95-6.35 (m, 4H), 4.26-3.48 (m, 5H), 3.10-2.78 (m, 1H), 2.05-0.60 (m, 14H)。 9-024(#1): δ13.58-13.28 (m, 1H), 7.61-6.75 (m, 4H), 3.76 (s, 3H), 3.09-2.88 (m, 1H), 2.55-2.22 (m, 4H), 1.98-0.69 (m, 14H)。 9-026(#1): δ13.52-13.28 (m, 1H), 7.68-6.76 (m, 5H), 3.78 (s, 3H), 2.48-1.95 (m, 11H), 1.20-1.00 (m, 3H)。 9-028(#1): δ13.70-13.45 (m, 1H), 7.71-6.72 (m, 4H), 4.25-3.38 (m, 8H), 2.22-1.90 (m, 6H)。 9-030(#1): δ13.51-13.18 (m, 1H), 8.05-6.72 (m, 5H), 4.31-3.70 (m, 5H), 2.76-1.93 (m, 10H)。 9-031(#1): δ13.57-13.28 (m, 1H), 7.66-6.75 (m, 5H), 3.78 (s, 3H), 2.72-1.39 (m, 14H)。 9-033(#1): δ13.55-13.18 (m, 1H), 7.64-6.70 (m, 4H), 5.83-5.48 (m, 1H), 5.20-4.90 (m, 2H), 3.72 (s, 3H), 3.30-0.98 (m, 12H)。9-035(#1): δ13.54-13.22 (m, 1H), 7.61-6.72 (m, 4H), 3.76 (s, 3H), 3.21-2.95 (m, 1H), 2.55-2.20 (m, 4H), 1.94-0.69 (m, 16H)。 9-036(#1): δ13.62-13.30 (m, 1H), 7.75-6.92 (m, 4H), 4.13-3.85 (m, 2H), 3.65 (s, 3H), 3.22-2.96 (m, 1H), 2.09-0.79 (m, 16H)。 9-038(#2): δ13.75-13.39 (m, 1H), 7.70-6.77 (m, 4H), 6.22-5.95 (m, 1H), 5.35-5.10 (m, 2H), 3.95-3.70 (m, 4H), 2.68-0.80 (m, 13H)。 9-039(#2): δ13.67-13.25 (m, 1H), 7.74-6.83 (m, 4H), 6.19-5.85 (m, 1H), 5.28-5.05 (m, 2H), 4.15-3.32 (m, 6H), 2.21-0.89 (m, 9H)。 9-045(#1): δ13.56-13.15 (m, 1H), 7.71-6.69 (m, 4H), 3.73 (s, 3H), 3.39-0.79 (m, 17H)。 9-046(#1): δ13.60-13.13 (m, 1H), 7.68-6.75 (m, 4H), 3.78 (s, 3H), 3.25-0.75 (m, 15H)。 9-047(#1): δ13.61-13.19 (m, 1H), 7.69-6.73 (m, 4H), 5.90-5.61 (m, 1H), 5.20-4.92 (m, 2H), 3.78 (s, 3H), 3.52-1.10 (m, 12H)。 9-048(#1): δ13.58-13.28 (m, 1H), 7.65-6.77 (m, 4H), 6.15-5.90 (m, 1H), 5.33-5.11 (m, 2H), 4.00-1.12 (m, 13H)。 9-049(#1): δ13.60-13.35 (m, 1H), 7.70-5.38 (m, 6H), 3.85-3.65 (m, 3H), 2.48-1.85 (m, 9H)。9-053(#1): δ13.62-13.20 (m, 1H), 7.80-6.71 (m, 4H), 3.85-1.20 (m, 16H). 9-054(#1): δ13.89-13.25 (m, 1H), 8.81-6.61 (m, 7H), 3.95-3.70 (m, 3H), 2.30-1.97 (m, 6H). 11-001(#2): δ 8.10-6.20 (m, 7H), 3.95-3.80 (m, 3H). 11-003(#2): δ 8.01-6.42 (m, 5H), 3.98-3.72 (m, 3H), 2.78-2.41 (m, 2H), 1.31-0.99 (m, 3H), NH2 2H not detected. 11-007(#2): δ 8.83-6.01 (m, 5H), 4.21-3.52 (m, 3H), NH2 2H not detected. 11-011(#2): δ 7.90-6.08 (m, 7H), 4.01-3.60 (m, 5H), 1.70-1.44 (m, 2H), 1.00-0.79 (m, 3H). 11-012(#2): δ 7.92-6.60 (m, 5H), 4.43-3.55 (m, 5H), 2H of NH2 not detected. 11-014(#2): δ 7.58-6.52 (m, 4H), 4.95-3.82 (m, 2H), 3.70-3.60 (m, 3H), 2.05-1.94 (m, 3H), 1.65-1.50 (m, 2H), 1.93-1.81 (m, 3H), 2H of NH2 not detected. ---------------------------------------------------------------- Among the compounds of the present invention shown in Tables 2 to 11, the configuration of the geometric isomers Compound (1A) or Compound (1B) is estimated as follows.

[0452] It was presumed that some of the compounds of the present invention shown in Tables 2 to 11 form intramolecular hydrogen bonds and others do not, depending on the configuration of geometric isomers. For example, compounds No. 1-003 and No. 1-004 (R ２ "(G-52a)-6-Me)" are geometric isomers, and No. 1-003 is a compound in which the hydrogen atom on the nitrogen atom in the enamide structure is bonded to the R ２forms an intramolecular hydrogen bond with the nitrogen atom in the pyridine ring of No. 1-004, but does not form an intramolecular hydrogen bond.

[0453] The hydrogen atoms that form hydrogen bonds are １ Since a characteristic low-field peak is observed in H-NMR, R ２ In the compound of the present invention, １ The configuration of the geometric isomer was estimated based on whether or not there was a peak in the low field of H-NMR.

[0454] The compound whose configuration was estimated by the above method １ The H-NMR data are shown in Table 14. The following data were measured in deuterated chloroform, with "#1" indicating that the measurement was performed at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL), and similarly, "#2" indicating that the measurement was performed at 400 MHz (model: JNM-ECZ400S, manufactured by JEOL).

[0455] [Forms hydrogen bonds within the molecule. Corresponding to compound (1A)] Compounds: Nos. 1-003, 1-010, 1-012, 1-015, 1-017, 1-018, 2-001, 3-002, 4-002, 4-003.

[0456] [Does not form intramolecular hydrogen bonds. Corresponding to compound (1B)] Compounds: Nos. 1-004, 1-011, 1-013, 2-002, and 3-003.

[0457] [Table 14] ------------------------------------------------------------------ No. 1H-NMR (CDCl3, Me4Si) ―――――――――――――――――――――――――――――――――― 1-003(#1): δ14.40-14.27 (m, 1H), 8.07-7.96 (m, 1H), 7.59-7.42 (m, 3H), 7.18 (d, 1H, J=3.7Hz), 7.10-6.94 (m, 3H), 6.88 (d, 1H, J=7.8Hz), 3.92 (s, 3H), 2.80 (s, 3H)。 1-004(#1): δ8.56-8.38 (m, 2H), 7.98-7.87 (m, 1H), 7.58 (s, 1H), 7.44 (t, 1H, J=8.2Hz), 7.16 (d, 1H, J=3.7Hz), 7.09-6.94 (m, 3H), 6.77 (d, 1H, J=7.8Hz), 3.98 (s, 3H), 2.59 (s, 3H)。 1-010(#2): δ13.10 (d, 1H, J=10.8Hz), 7.80-6.70 (m, 10H), 3.93 (s, 3H), 2.43 (s, 3H)。 1-011(#2): δ8.60-6.50 (m, 11H), 4.00-3.80 (m, 3H), 2.42 (s, 3H)。 1-012(#2): δ13.13 (d, 1H, J=11.2Hz), 7.80-6.80 (m, 10H), 3.93 (s, 3H)。 1-013(#2): δ8.60-6.40 (m, 11H), 4.00-3.90 (m, 3H)。 2-001(#1): δ13.10 (d, 1H, J=11.1Hz), 8.10-7.98 (m, 1H), 7.58 (t, 1H, J=7.8Hz), 7.50-6.90 (m, 7H), 3.86 (s, 3H), 2.17 (s, 3H)。 2-002(#1): δ8.60-6.70 (m, 10H), 3.92 (s, 3H), 3.12 (s, 3H)。 3-002(#1): δ13.03-12.91 (m, 1H), 8.10-6.91 (m, 10H), 3.96 (s, 3H)。3-003(#1): δ8.78-8.68 (m, 1H), 8.28 (d, 1H, J=12.3Hz), 8.05-6.92 (m, 9H), 4.03(s, 3H). 1-015(#1): δ14.00-13.80 (m, 1H), 8.83-8.70 (m, 1H), 8.12-6.88 (m, 9H), 3.93(s, 3H). 1-017(#1): δ13.90-13.69 (m, 1H), 8.85-8.70 (m, 1H), 8.35-8.18 (m, 1H), 7.95-7.80 (m, 1H), 7.70-6.88 (m, 6H), 3.92(s, 3H). 1-018(#1): δ13.20-13.00 (m, 1H), 7.99-6.42 (m, 9H), 3.90(s, 3H). 4-002(#1): δ12.18-11.85 (m, 1H), 7.75-6.81 (m, 9H), 3.99-3.62 (m, 5H). 4-003(#1): δ 11.10-10.89 (m, 1H), 8.01-7.82 (m, 1H), 7.68-6.55 (m, 9H), 4.01-3.75 (m, 3H). ---------------------------------------------------------------- The configuration of the compound of the present invention was estimated as follows from the retention time of LCMS analysis.

[0458] １ ​The configuration of the compounds of the present invention was estimated by H-NMR based on the presence or absence of hydrogen bonds. LCMS analysis was performed on a compound estimated to have the configuration of compound (1A) and a compound estimated to have the configuration of compound (1B). Examples of retention times under analytical conditions for the compounds of the present invention are shown below. 1-003 [Intramolecular hydrogen bond formed. Corresponding to compound (1A)] Retention time: 4.02 minutes (Condition a) 1-004 [Geometric isomer of 1-003, corresponding to compound (1B)] Retention time: 2.02 minutes (Condition a) 1-010 [Intramolecular hydrogen bond formed. Corresponding to compound (1A)] Retention time: 4.18 minutes (Condition a) 1-011 [Geometric isomer of 1-010, corresponding to compound (1B)] Retention time: 3.72 minutes (Condition a) 1-012 [Intramolecular hydrogen bond formed. Corresponding to compound (1A)] Retention time: 4.24 minutes (condition a) 1-013 [Geometric isomer of 1-012, corresponding to compound (1B)] Retention time: 3.75 minutes (condition a) 2-001 [Intramolecular hydrogen bond formed. Corresponding to compound (1A)] Retention time: 3.44 minutes (condition a) 2-002 [Geometric isomer of 2-001, corresponding to compound (1B)] Retention time: 3.19 minutes (condition a) 3-002 [Intramolecular hydrogen bond formed. Corresponding to compound (1A)] Retention time: 3.34 minutes (condition a) 3-003 [Geometric isomer of 3-002, corresponding to compound (1B)] Retention time: 3.06 minutes (condition a).

[0459] The retention times of the mixture of geometric isomers under condition b and the product after purification are also shown below. The mixture of geometric isomers was measured in the reaction solution after completion of the reaction when the compound of the present invention was synthesized according to the above synthesis example. 1-015 (mixture of geometric isomers after completion of reaction) Retention times: 1.37 minutes & 2.48 minutes (condition b) 1-015 [Intramolecular hydrogen bonds formed. Corresponding to compound (1A)] Retention time: 2.48 minutes (condition b) 1-017 (mixture of geometric isomers after completion of reaction) Retention times: 1.85 minutes & 1.96 minutes (condition b) 1-017 [Intramolecular hydrogen bonds formed. Corresponding to compound (1A)] Retention time: 1.96 min (condition b) 1-018 (Mixture of geometric isomers after completion of reaction) Retention times: 2.22 min & 2.42 min (condition b) 1-018 [Hydrogen bonds formed within the molecule. Corresponding to compound (1A)] Retention time: 2.42 min (condition b) 4-002 (Mixture of geometric isomers after completion of reaction) Retention times: 2.28 min & 2.44 min (condition b) 4-002 [Hydrogen bonds formed within the molecule. Corresponding to compound (1A)] Retention time: 2.44 min (condition b) 4-003 (Mixture of geometric isomers after completion of reaction) Retention times: 2.66 min & 2.81 min (condition b) 4-003 [Hydrogen bonds formed within the molecule. Corresponding to compound (1A)] Retention time: 2.81 minutes (condition b) In both conditions a and b, the order of retention times in LCMS analysis was slower for compound (1A) and faster for compound (1B). Therefore, the configuration of the geometric isomers of compound (1) of the present invention was estimated based on the order of retention times in LCMS analysis.

[0460] [Test Examples] Next, the usefulness of the compound of the present invention as a pest control agent will be specifically explained in the following test examples, but the present invention is not limited to these. In the test examples, "RH" represents relative humidity, and for example, the description "humidity 100% RH" means that the relative humidity is 100%.

[0461] Preparation of test drug solutions Emulsions containing the compound of the present invention at concentrations of 1% by mass, 5% by mass, or 20% by mass were prepared according to the above-mentioned formulation examples of emulsions. These emulsions were used as test drug solutions in the following Test Examples 1 to 7.

[0462] Test Example 1: Wheat blight control effect test 90 cm ３ Wheat (variety: Haruyutaka) was planted in plastic pots of 1.0 mm diameter, and at the 1.3-leaf stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the plants. One day after spraying, the wheat plants were inoculated by spraying with a conidial suspension of Septoria nodorum, and then placed in an inoculation box at 20°C and 100% RH for 2 days. The plants were then placed in an air-conditioned greenhouse (temperature 20°C, humidity 80% RH) and maintained there for 8 days. The proportion of lesions formed relative to the inoculated leaves was measured, and the control value was calculated according to the following formula:

[0463] Control titer = [1 - (lesion area rate in treated plot / lesion area rate in untreated plot)] x 100 As a result, of the compounds tested, the following compounds showed a control titer of 70% or more.

[0464] Compounds: No. 1-001, 1-006, 1-007, 1-008, 1-009, 1-012, 1-013, 1-016, 1-018, 1-020, 1-021, 1-022, 1-024, 1-025, 1-026, 1-027, 1-028, 1-029, 1-030, 2-001, 2-0 02, 2-003, 2-004, 2-005, 2-006, 2-013, 2-014, 2-016, 2-017, 2-018, 2-019, 2-020, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-029, 2-030, 2-031, 2 -033, 2-034, 2-037, 2-038, 2-039, 2-042, 2-043, 2-044, 2-045, 2-046, 3-005, 3-007, 3-008, 4-004, 4-005, 4-007, 4-008, 4-009, 5-003, 5-011, 5-012 , 5-016, 5-052, 5-056, 5-060, 5-061, 5-062, 5-064, 5-067, 5-068, 5-069, 5-070, 5-072, 5-073, 5-076, 5-077, 5-078, 5-088, 5-097, 5-100, 5-101, 5-1 02, 5-103, 5-104, 5-108, 5-111, 5-112, 5-113, 5-115, 5-116, 5-117, 5-122, 5-126, 5-129, 5-131, 5-133, 5-134, 5-137, 5-138, 6-001, 6-002, 6-003, 6-006, 6-010, 6-011, 6-012, 6-013, 6-016, 6-017, 6-018, 6-019, 6-020, 6-021, 6-023, 6-024, 6-025, 6-027, 6-029, 6-032, 6-033, 6-034, 6-035, 6-03 8, 6-039, 6-040, 6-041, 6-042, 6-044, 6-045, 6-046, 6-047, 6-048, 6-049, 6-050, 6-051, 6-052, 6-053, 6-056, 6-057, 6-058, 6-059, 6-060, 6-061, 6- 063, 6-064, 6-065, 6-066, 6-067, 6-068, 6-069, 6-071, 6-072, 6-074, 6-075, 6-076, 6-077, 6-078, 6-079, 6-080, 6-081, 6-085, 6-086, 6-087, 6-088,６－０９１、６－０９２、６－０９４、６－０９６、６－０９７、６－０９８、６－０９９、６－１００、６－１０１、６－１０２、６－１０３、６－１０４、６－１０５、６－１０６、６－１０７、６－１０８、６－１１０、６－１１１、６－１１３、６－１１４、６－１１５、６－１１８、６－１１９、６－１２０、６－１２１、６－１２２、６－１２３、６－１２４、６－１２５、６－１２６、６－１２７、６－１２８、６－１２９、６－１３０、６－１３１、６－１３２、６－１３４、６－１３５、６－１３６、６－１３７、６－１３８、６－１３９、６－１４０、６－１４１、６－１４２、６－１４３、６－１４４、６－１４５、６－１４６、６－１４７、６－１４８、６－１４９、６－１５０、６－１５１、６－１５２、６－１５３、６－１５４、６－１５５、６－１５６、６－１５７、６－１５８、６－１５９、６－１６０、６－１６２、６－１６３、６－１６４、６－１６５、６－１６６、６－１６７、６－１６８、６－１６９、６－１７０、６－１７１、６－１７３、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８２、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１９９、６－１７０、６－１７１、６－１７２、６－１７３、６－１７４、６－１７５、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８２、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１９９、６－２００、６－２０１、６－２０２、６－２０３、６－２０４、６－２０５、６－２０６、６－２０７、６－２０８、６－２０９、６－２１０、６－２１１、６－２１２、６－２１３、６－２１４、６－２１５、６－２１６、６－２１７、６－２１８、６－２１９、６－２２０、６－２２１、６－２２２、６－２２３、６－２２４、６－２２５、６－２２６、６－２２７、６－２２８、６－２２９、６－２３０、６－２３１、６－２３２、６－２３３、６－２３４、６－２３５、６－２３６、６－２３７、６－２３８、６－２３９、６－２４０、６－２４１、６－２４２、６－２４３、６－２４４、６－２４５、６－２４６、６－２４７、６－２４８、６－２４９、６－２５０、６－２５１、６－２５２、６－２５３、６－２５４、６－２５５、６－２５６、６－２５７、６－２５８、６－２５９、６－２６０、６－２６１、６－２６２、６－２６３、６－２６４、６－２６５、６－２６６、６－２６７、６－２６８、６－２６９、６－２７０、６－２７１、６－２７２、６－２７３、６－２７４、６－２７５、６－２７６、６－２７７、６－２７８、６－２７９、６－２８０、６－２８１、６－２８２、６－２８３、６－２８４、６－２８５、６－２８６、６－２８７、６－２８８、６－２８９、６－２９０、６－２９１、６－２９２、６－２９３、６－２９４、６－２９５、６－２９６、６－２９７、６－２９８、６－２９９、６－３００、６－３０１、６－３０２、６－３０３、６－３０４、６－３０５、６－３０６、６－３０７、６－３０８、６－３０９、６－３１０、６－３１１、６－３１２、６－３１３、６－３１４、６－３１５、６－３１６、６－３１７、６－３１８、６－３１９、６－３２０、６－３２１、６－３２２、６－３２３、６－３２４、６－３２５、６－３２６、６－３２７、６－３２８、６－３２９、６－３３０、６－３３１、６－３３２、６－３３３、６－３３５、６－３３６、６－３３７、６－３３８、６－３３９、６－３４０、６－３４１、６－３４２、６－３４３、６－３４４、６－３４５、６－３４６、６－３４７、６－３４８、６－３４９、６－３５０、６－３５１、６－３５２、６－３５３、６－３５４、６－３５５、６－３５６、６－３５７、６－３５８、６－３５９、６－３６０、６－３６１、６－３６２、６－３６３、６－３６４、６－３６５、６－３６６、６－３６７、６－３６９、６－３７０、６－３７１、６－３７２、６－３７３、６－３７４、６－３７５、６－３７６、６－３７７、６－３７８、６－３７９、６－３８０、６－３８１、６－３８２、６－３８３、６－３８４、６－３８５、６－３８６、６－３８７、６－３８８、６－３８９、６－３９０、６－３９１、６－３９２、６－３９３、６－３９４、６－３９５、６－３９６、６－３９７、６－３９８、６－３９９、６－４００、６－４０１、６－４０２、６－４０３、６－４０４、６－４０５、6-406, 6-407, 6-408, 6-409, 6-410, 6-411, 6-412, 6-413, 6-414, 6-415, 6-416, 6-417, 6-418, 6-419, 6-420, 6-421, 7-001, 8-001, 8-003, 8-004, 8-005, 8-006, 8-00 7, 8-008, 8-009, 8-010, 8-011, 8-012, 8-013, 8-014, 8-015, 9-001, 9-002, 9-003, 9-005, 9-006, 9-007, 9-008, 9-009, 9-010, 9-011, 9-012, 9-013, 9-014, 9-015, 9- 016, 9-017, 9-018, 9-019, 9-020, 9-021, 9-022, 9-023, 9-024, 9-025, 9-026, 9-029, 9-030, 9-031, 9-032, 9-033, 9-034, 9-035, 9-036, 9-037, 9-038, 9-039, 9-040, 9-041, 9-042, 9-043, 9-044, 9-045, 9-046, 9-047, 9-048, 9-049, 9-050, 9-051, 9-052, 9-053, 9-054, 9-055, 9-056, 9-057, 10-001, 10-002, 10-003, 10-005, 10-006.

[0465] Test Example 2: Tomato powdery mildew control effect test 90 cm ３ Tomatoes (variety: Momotaro) were planted in plastic pots of 100 mm diameter, and at the two-leaf stage, 5 ml of a test solution diluted with water to a concentration of 500 ppm was sprayed onto the plants. After air-drying, the tomatoes were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated with a conidial suspension of tomato powdery mildew (Leveillula taurica) by spray inoculation. After leaving the plants for 14 days, the proportion of lesions formed on the inoculated leaves was measured, and the control titer was calculated using the same formula as in Test Example 1.

[0466] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0467] Compounds: No. 1-001, 1-003, 1-008, 1-009, 1-011, 1-012, 1-016, 1-020, 1-021, 1-022, 1-023, 1-026, 1-027, 1-030, 2-001, 2-002, 2-005, 2-006, 2-012, 2-013, 2-0 14, 2-018, 2-022, 2-024, 2-025, 2-029, 2-030, 2-036, 2-037, 2-039, 2-041, 2-042, 2-046, 3-005, 3-007, 3-008, 4-004, 4-005, 4-007, 4-008, 4-009, 5 -001, 5-002, 5-003, 5-015, 5-038, 5-039, 5-040, 5-060, 5-061, 5-062, 5-063, 5-066, 5-067, 5-068, 5-069, 5-070, 5-074, 5-077, 5-078, 5-093, 5-104 , 5-105, 5-106, 5-107, 5-111, 5-112, 5-113, 5-114, 5-118, 5-126, 5-137, 5-138, 6-001, 6-003, 6-009, 6-013, 6-016, 6-018, 6-020, 6-022, 6-023, 6-0 25, 6-026, 6-027, 6-029, 6-031, 6-032, 6-033, 6-034, 6-038, 6-039, 6-041, 6-042, 6-044, 6-045, 6-046, 6-047, 6-048, 6-049, 6-050, 6-052, 6-053, 6-054, 6-055, 6-059, 6-060, 6-063, 6-067, 6-068, 6-069, 6-071, 6-074, 6-075, 6-076, 6-077, 6-078, 6-087, 6-088, 6-090, 6-095, 6-096, 6-097, 6-09 8, 6-099, 6-100, 6-107, 6-108, 6-111, 6-112, 6-113, 6-114, 6-115, 6-117, 6-119, 6-120, 6-121, 6-122, 6-123, 6-124, 6-125, 6-127, 6-129, 6-130, 6- 132, 6-134, 6-136, 6-137, 6-138, 6-139, 6-140, 6-141, 6-142, 6-144, 6-145, 6-151, 6-152, 6-153, 6-154, 6-156, 6-157, 6-158, 6-159, 6-160, 6-162,６－１６３、６－１６４、６－１６５、６－１６６、６－１６９、６－１７１、６－１７２、６－１７３、６－１７４、６－１７６、６－１７７、６－１７８、６－１８０、６－１８１、６－１８３、６－１８５、６－１８６、６－１８８、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９７、６－１９９、６－１７０、６－１７１、６－１７２、６－１７３、６－１７４、６－１７５、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８２、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１９９、６－２００、６－２０１、６－２０２、６－２０３、６－２０４、６－２０５、６－２０６、６－２０７、６－２０８、６－２１０、６－２１１、６－２１２、６－２１３、６－２１５、６－２１６、６－２１７、６－２１８、６－２１９、６－２２３、６－２２４、６－２２５、６－２２６、６－２２７、６－２２８、６－２２９、６－２３０、６－２３１、６－２３４、６－２３５、６－２３７、６－２３８、６－２４０、６－２４２、６－２４３、６－２４４、６－２４５、６－２４６、６－２４７、６－２４９、６－２５１、６－２５２、６－２５３、６－２５５、６－２５８、６－２５９、６－２６０、６－２６１、６－２６３、６－２６４、６－２６５、６－２６６、６－２６７、６－２６９、６－２７０、６－２７１、６－２７２、６－２７３、６－２７５、６－２７６、６－２７７、６－２７８、６－２７９、６－２８０、６－２８２、６－２８３、６－２８５、６－２８６、６－２８７、６－２８８、６－２８９、６－２９０、６－２９１、６－２９２、６－２９４、６－２９５、６－２９６、６－２９７、６－２９８、６－２９９、６－３００、６－３０２、６－３０４、６－３０５、６－３０６、６－３０７、６－３０８、６－３１１、６－３１４、６－３１５、６－３１８、６－３１９、６－３２１、６－３２２、６－３２５、６－３３２、６－３３３、６－３３６、６－３３９、６－３４０、６－３４３、６－３４４、６－３４５、６－３４８、６－３４９、６－３５０、６－３５１、６－３５３、６－３５４、６－３５９、６－３６４、6-366, 6-369, 6-370, 6-371, 6-373, 6-374, 6-380, 6-381, 6-382, 6-383, 6-385, 6-386, 6-387, 6-388, 6-389, 6-390, 6-391, 6-393, 6-399, 6-400, 6-401, 6-402, 6-403, 6-404, 6-405, 6-406, 6-407, 6-408, 6-409, 6-410, 6-411, 6-412, 6-413, 6-414, 6-415, 6-416, 6-417, 6-418, 7-001, 8-001, 8-003, 8-004, 8-006, 8-007, 8-008, 8-009, 8-010, 8-011, 8-012, 8-013, 8-014, 8-015, 9-001, 9-002, 9-003, 9-005, 9-006, 9-007, 9-008, 9-009, 9-010, 9-011, 9-012, 9-013, 9-014, 9-016, 9-017, 9-019, 9-020, 9-021, 9-022, 9-023, 9-024, 9-026, 9-031, 9-032, 9-033, 9-034, 9-035, 9-036, 9-037, 9-038, 9-039, 9-040, 9-041, 9-042, 9-043, 9-045, 9-046, 9-047, 9-048, 9-050, 9-051, 9-052, 9-053, 9-054, 9-055, 9-056, 9-057, 10-001.

[0468] Test Example 3: Cucumber gray mold control effect test 90 cm ３ Cucumbers (variety: Sagamihanjiro) were planted in plastic pots. At the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed on the plants and air-dried. The treated leaves were then cut off and placed in a plastic container. A conidial suspension of Botrytis cinerea and dissolved PDA medium were mixed at a 1:1 (volume ratio), and 30 μl of the mixture was dropwise inoculated onto the treated leaves. After inoculation, the plants were left at 20°C and humid (100% RH) for 3 days. The proportion of lesions formed on the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0469] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0470] Compounds: Nos. 1-001, 1-002, 1-007, 1-008, 1-009, 1-012, 1-013, 1-016, 1-018, 1-019, 1-020, 1-021, 1-022, 1-023, 1-024, 1-026, 1-027, 1-028, 1-029, 1-030, 2-001, 2-002 , 2-003, 2-004, 2-005, 2-006, 2-009, 2-010, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-021, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-039, 2-040, 2-0 41, 2-042, 2-043, 2-044, 2-045, 2-046, 3-001, 3-005, 3-006, 3-007, 3-008, 3-009, 4-004, 4-005, 4-007, 4-008, 4-009, 5-001, 5-002, 5-003, 5-004, 5-008, 5-010, 5-011, 5-012, 5-013, 5-015, 5-022, 5-024, 5-025, 5-030, 5-031, 5-036, 5-037, 5-038, 5-039, 5- 040, 5-041, 5-046, 5-048, 5-049, 5-050, 5-053, 5-055, 5-056, 5-057, 5-058, 5-060, 5-061, 5-062, 5-063, 5-064, 5-065, 5-066, 5-067, 5-068, 5-069, 5-070, 5-071, 5-073, 5-074, 5-077, 5-078, 5-079, 5-080, 5-081, 5-084, 5-088, 5-093, 5-094, 5-095, 5-100, 5 -101, 5-102, 5-104, 5-105, 5-106, 5-107, 5-108, 5-111, 5-112, 5-113, 5-114, 5-116, 5-117, 5-126, 5-131, 5-137, 5-138, 6-001, 6-002, 6-003, 6-006, 6-008, 6-009, 6-010, 6-012, 6-013, 6-016, 6-018, 6-019, 6-020, 6-021, 6-023, 6-024, 6-025, 6-027, 6-028,６－０３１、６－０３２、６－０３３、６－０３４、６－０３５、６－０３６、６－０３７、６－０３８、６－０３９、６－０４０、６－０４１、６－０４２、６－０４３、６－０４４、６－０４５、６－０４６、６－０４７、６－０４８、６－０４９、６－０５０、６－０５１、６－０５２、６－０５３、６－０５４、６－０５５、６－０５６、６－０５７、６－０５８、６－０５９、６－０６０、６－０６１、６－０６２、６－０６３、６－０６４、６－０６５、６－０６６、６－０６７、６－０６８、６－０６９、６－０７０、６－０７１、６－０７２、６－０７４、６－０７５、６－０７６、６－０７７、６－０７８、６－０７９、６－０８０、６－０８１、６－０８５、６－０８６、６－０８７、６－０８８、６－０９１、６－０９２、６－０９３、６－０９４、６－０９６、６－０９７、６－０９８、６－０９９、６－１００、６－１０１、６－１０２、６－１０３、６－１０４、６－１０５、６－１０６、６－１０７、６－１０８、６－１１１、６－１１２、６－１１３、６－１１４、６－１１５、６－１１７、６－１１８、６－１１９、６－１２０、６－１２１、６－１２２、６－１２３、６－１２４、６－１２５、６－１２６、６－１２７、６－１２８、６－１２９、６－１３０、６－１３１、６－１３２、６－１３３、６－１３４、６－１３５、６－１３６、６－１３７、６－１３８、６－１３９、６－１４０、６－１４１、６－１４２、６－１４３、６－１４４、６－１４５、６－１４６、６－１４７、６－１４８、６－１５１、６－１５２、６－１５３、６－１５４、６－１５５、６－１５６、６－１５８、６－１５９、６－１６２、６－１６３、６－１６４、６－１６５、６－１６６、６－１６７、６－１６８、６－１６９、６－１７０、６－１７１、６－１７３、６－１７６、６－１７７、６－１７８、６－１８０、６－１８１、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－２００、６－２０１、６－２０２、６－２０４、６－２０５、６－２０６、６－２０７、６－２０８、６－２０９、６－２１０、６－２１１、６－２１２、６－２１３、６－２１４、６－２１７、６－２１８、６－２１９、６－２２０、６－２２１、６－２２２、６－２２３、６－２２４、６－２２５、６－２２６、６－２２７、６－２２８、６－２２９、６－２３０、６－２３１、６－２３２、６－２３３、６－２３４、６－２３５、６－２３６、６－２３７、６－２３８、６－２３９、６－２４０、６－２４１、６－２４２、６－２４３、６－２４４、６－２４５、６－２４６、６－２４７、６－２４８、６－２４９、６－２５２、６－２５３、６－２５４、６－２５５、６－２５６、６－２５７、６－２５８、６－２５９、６－２６０、６－２６１、６－２６２、６－２６３、６－２６４、６－２６５、６－２６６、６－２６７、６－２６８、６－２６９、６－２７０、６－２７１、６－２７２、６－２７３、６－２７４、６－２７５、６－２７６、６－２７７、６－２７８、６－２７９、６－２８０、６－２８１、６－２８２、６－２８３、６－２８４、６－２８５、６－２８６、６－２８７、６－２８８、６－２８９、６－２９０、６－２９１、６－２９２、６－２９３、６－２９４、６－２９５、６－２９６、６－２９７、６－２９８、６－２９９、６－３００、６－３０１、６－３０２、６－３０３、６－３０４、６－３０５、６－３０６、６－３０７、６－３０８、６－３０９、６－３１０、６－３１１、６－３１２、６－３１３、６－３１４、６－３１５、６－３１６、６－３１７、６－３１８、６－３１９、６－３２０、６－３２１、６－３２２、６－３２３、６－３２４、６－３２５、６－３２６、６－３２７、６－３２８、６－３２９、６－３３０、６－３３２、６－３３３、６－３３４、６－３３５、６－３３６、６－３３７、６－３３８、６－３３９、６－３４０、６－３４１、６－３４２、６－３４３、６－３４４、６－３４５、６－３４６、６－３４７、６－３４８、６－３４９、６－３５０、６－３５１、６－３５２、６－３５３、６－３５４、６－３５５、６－３５６、６－３５７、６－３５８、６－３５９、６－３６０、６－３６４、６－３６５、６－３６７、６－３６９、６－３７０、６－３７１、６－３７２、６－３７３、６－３７４、６－３７５、６－３７６、６－３７８、６－３７９、６－３８０、６－３８１、６－３８２、６－３８３、６－３８５、６－３８６、６－３８７、６－３８８、６－３８９、６－３９０、６－３９１、６－３９２、６－３９３、６－３９４、６－３９６、６－３９７、６－３９８、6-399, 6-400, 6-401, 6-402, 6-403, 6-404, 6-405, 6-406, 6-407, 6-408, 6-409, 6-410, 6-411, 6-412, 6-413, 6-414, 6-415, 6-416, 6-417, 6-418, 6-419, 6-420, 6-421, 7- 001, 8-003, 8-004, 8-005, 8-006, 8-007, 8-008, 8-009, 8-010, 8-011, 8-012, 8-013, 8-014, 8-015, 9-001, 9-002, 9-003, 9-005, 9-006, 9-007, 9-008, 9-009, 9-010, 9-01 1, 9-012, 9-013, 9-014, 9-015, 9-016, 9-017, 9-019, 9-020, 9-021, 9-022, 9-023, 9-024, 9-025, 9-026, 9-029, 9-030, 9-031, 9-032, 9-033, 9-034, 9-035, 9-036, 9-037, 9-038, 9-039, 9-040, 9-041, 9-042, 9-043, 9-044, 9-045, 9-046, 9-047, 9-048, 9-049, 9-050, 9-051, 9-052, 9-053, 9-054, 9-055, 9-056, 9-057, 10-001, 10-002, 10-003.

[0471] Test Example 4: Cucumber stem rot control effect test 90 cm ３ Cucumbers (variety: Sagamihanjiro) were planted in plastic pots. At the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the plants and air-dried. The treated leaves were then placed in a plastic container. Agar pieces (5 mm in diameter) containing cucumber stem rot (Sclerotinia sclerotiorum) that had been previously cultured on PDA medium were inoculated onto the treated cucumber cotyledons. After inoculation, the plastic container was covered with vinyl, humidified (100% RH), and left at 20°C for 2 days. The proportion of lesions formed relative to the inoculated leaves was then measured, and the control value was calculated using the same formula as in Test Example 1.

[0472] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0473] Compounds: No. 1-001, 1-008, 1-009, 1-014, 1-018, 1-019, 1-021, 1-022, 1-023, 1-024, 1-026, 1-027, 1-028, 1-029, 1-030, 2-001, 2-003, 2-005, 2-006, 2-009, 2-0 10, 2-011, 2-012, 2-013, 2-014, 2-015, 2-016, 2-017, 2-018, 2-019, 2-020, 2-022, 2-023, 2-024, 2-025, 2-026, 2-027, 2-028, 2-029, 2-030, 2-031, 2 -032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-039, 2-040, 2-041, 2-042, 2-044, 2-045, 2-046, 3-001, 3-002, 3-005, 3-006, 3-007, 3-008, 3-009, 4-004 , 4-005, 4-007, 4-008, 4-009, 5-001, 5-002, 5-003, 5-009, 5-010, 5-012, 5-015, 5-024, 5-030, 5-038, 5-040, 5-057, 5-060, 5-061, 5-062, 5-063, 5-0 66, 5-067, 5-068, 5-069, 5-070, 5-073, 5-074, 5-077, 5-078, 5-084, 5-085, 5-088, 5-093, 5-094, 5-097, 5-101, 5-102, 5-107, 5-112, 5-113, 5-117, 5-126, 5-130, 5-137, 5-138, 6-001, 6-002, 6-003, 6-006, 6-008, 6-009, 6-010, 6-013, 6-016, 6-018, 6-019, 6-020, 6-021, 6-022, 6-023, 6-024, 6-02 5, 6-027, 6-031, 6-032, 6-033, 6-034, 6-035, 6-036, 6-037, 6-038, 6-039, 6-040, 6-041, 6-042, 6-043, 6-044, 6-045, 6-047, 6-048, 6-049, 6-050, 6- 051, 6-052, 6-053, 6-054, 6-055, 6-056, 6-058, 6-059, 6-060, 6-061, 6-063, 6-064, 6-065, 6-067, 6-068, 6-069, 6-071, 6-072, 6-074, 6-075, 6-076,６－０７７、６－０７８、６－０７９、６－０８１、６－０８５、６－０８６、６－０８８、６－０９０、６－０９２、６－０９３、６－０９４、６－０９５、６－０９６、６－０９７、６－０９８、６－０９９、６－１００、６－１０１、６－１０２、６－１０３、６－１０４、６－１０５、６－１０７、６－１０８、６－１１０、６－１１１、６－１１３、６－１１４、６－１１５、６－１１９、６－１２１、６－１２２、６－１２３、６－１２４、６－１２５、６－１２６、６－１２７、６－１２９、６－１３０、６－１３１、６－１３２、６－１３４、６－１３６、６－１３７、６－１３９、６－１４０、６－１４１、６－１４２、６－１４３、６－１４４、６－１４６、６－１４７、６－１４８、６－１５１、６－１５２、６－１５３、６－１５４、６－１５５、６－１５６、６－１５７、６－１５８、６－１５９、６－１６０、６－１６１、６－１６２、６－１６３、６－１６４、６－１６５、６－１６６、６－１６７、６－１６８、６－１６９、６－１７０、６－１７１、６－１７３、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８３、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１７０、６－１７１、６－１７２、６－１７３、６－１７４、６－１７５、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８１、６－１８２、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１９９、６－２００、６－２０１、６－２０２、６－２０３、６－２０４、６－２０５、６－２０６、６－２０７、６－２０８、６－２０９、６－２１０、６－２１１、６－２１２、６－２１３、６－２１４、６－２１７、６－２１８、６－２１９、６－２２０、６－２２２、６－２２３、６－２２４、６－２２５、６－２２６、６－２２７、６－２２８、６－２２９、６－２３０、６－２３１、６－２３２、６－２３３、６－２３４、６－２３５、６－２３６、６－２３７、６－２３８、６－２３９、６－２４０、６－２４１、６－２４２、６－２４３、６－２４４、６－２４５、６－２４６、６－２４７、６－２４８、６－２４９、６－２５２、６－２５３、６－２５４、６－２５５、６－２５６、６－２５７、６－２５８、６－２５９、６－２６０、６－２６１、６－２６２、６－２６３、６－２６４、６－２６５、６－２６６、６－２６７、６－２６８、６－２６９、６－２７０、６－２７１、６－２７２、６－２７３、６－２７４、６－２７５、６－２７６、６－２７７、６－２７８、６－２７９、６－２８０、６－２８１、６－２８２、６－２８３、６－２８４、６－２８５、６－２８６、６－２８７、６－２８８、６－２８９、６－２９０、６－２９１、６－２９２、６－２９３、６－２９４、６－２９５、６－２９６、６－２９７、６－２９８、６－２９９、６－３００、６－３０２、６－３０３、６－３０４、６－３０５、６－３０６、６－３０７、６－３０８、６－３０９、６－３１０、６－３１１、６－３１２、６－３１３、６－３１４、６－３１５、６－３１６、６－３１７、６－３１８、６－３２０、６－３２１、６－３２２、６－３２３、６－３２４、６－３２５、６－３２７、６－３３０、６－３３１、６－３３２、６－３３３、６－３３６、６－３３７、６－３３９、６－３４０、６－３４１、６－３４２、６－３４３、６－３４４、６－３４５、６－３４８、６－３４９、６－３５０、６－３５２、６－３５３、６－３５５、６－３５６、６－３５７、６－３５８、６－３５９、６－３６０、６－３６４、６－３６５、６－３６７、６－３６９、６－３７０、６－３７１、６－３７２、６－３７３、６－３７４、６－３７５、６－３７６、６－３７８、６－３８０、６－３８１、６－３８２、６－３８３、６－３８８、６－３８９、６－４００、６－４０１、６－４０２、６－４０３、６－４０４、６－４０５、６－４０６、６－４０７、６－４０８、６－４０９、６－４１０、６－４１１、６－４１２、６－４１３、６－４１４、６－４１５、６－４１６、６－４１７、６－４１８、６－４１９、６－４２０、７－００１、８－００３、８－００４、８－００５、８－００６、８－００７、８－００８、８－００９、８－０１０、８－０１１、８－０１２、８－０１３、８－０１４、８－０１５、９－００１、９－００２、９－００３、９－００５、９－００６、９－００７、９－００８、９－００９、9-010, 9-011, 9-012, 9-014, 9-016, 9-017, 9-019, 9-020, 9-021, 9-022, 9-023, 9-024, 9-025, 9-026, 9-029, 9-030, 9-031, 9-032, 9-033, 9-034, 9-037, 9 -039, 9-040, 9-041, 9-042, 9-043, 9-045, 9-046, 9-047, 9-048, 9-049, 9-050, 9-051, 9-052, 9-053, 9-054, 9-055, 9-056, 9-057, 10-001, 10-002, 10-003.

[0474] Test Example 5 Cucumber powdery mildew control effect test 90 cm ３ Cucumbers (variety: Sagami Hanpaku) were planted in plastic pots of 100 mm diameter, and at the cotyledon stage, 5 ml of a test solution diluted with water to a concentration of 500 ppm was sprayed onto the plants. After air-drying, the cucumbers were placed in an air-conditioned greenhouse (temperature 20°C, humidity 70% RH) and inoculated by spraying with a conidial suspension of cucumber powdery mildew (Erysiphe polygoni). After leaving the plants for 9 days, the proportion of formed lesions on the inoculated leaves was measured, and the control titer was calculated using the same formula as in Test Example 1.

[0475] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0476] Compounds: Nos. 1-001, 1-006, 1-007, 1-008, 1-009, 1-014, 1-018, 1-021, 1-024, 1-026, 1-027, 1-028, 1-029, 1-030, 2-001, 2-002 , 2-003, 2-004, 2-005, 2-006, 2-007, 2-009, 2-010, 2-013, 2-014, 2-015, 2-016, 2-018, 2-019, 2-020, 2-022, 2-023, 2-024, 2-025, 2-029, 2-030, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038, 2-039, 2-041, 2-042, 2-044, 2-045, 2-046, 3-005, 3-008, 4-004, 4-005, 4-007, 4-008, 4-009, 5-001, 5-002, 5-007, 5-010, 5-011, 5-013, 5-025, 5-030, 5-036, 5-038, 5-040, 5-058, 5-060, 5-061, 5-062, 5-063, 5-066, 5-067, 5-068, 5-069, 5-070, 5-077, 5-078, 5-079, 5-081, 5-093, 5-094, 5-102, 5-104, 5-106, 5-107, 5-112, 5-113, 5-118, 5- 138, 6-001, 6-003, 6-004, 6-006, 6-008, 6-009, 6-010, 6-013, 6-017, 6-018, 6-019, 6-020, 6-021, 6-023, 6-024, 6-025, 6-027, 6-029, 6-031, 6-032, 6-034, 6-035, 6-036, 6-037, 6-038, 6-039, 6-040, 6-042, 6-044, 6-045, 6-048, 6-049, 6-050, 6-052, 6-053, 6-054, 6-05 5, 6-056, 6-057, 6-058, 6-059, 6-060, 6-061, 6-063, 6-064, 6-065, 6-067, 6-068, 6-069, 6-071, 6-072, 6-074, 6-075, 6-076, 6-077, 6-078, 6-081, 6-083, 6-085, 6-086, 6-087, 6-088, 6-092, 6-093, 6-094, 6-096, 6-097, 6-098, 6-100, 6-101, 6-102, 6-103, 6-104, 6-105,６－１０７、６－１０８、６－１１０、６－１１１、６－１１２、６－１１３、６－１１４、６－１１５、６－１１７、６－１１８、６－１１９、６－１２０、６－１２１、６－１２２、６－１２３、６－１２４、６－１２５、６－１２６、６－１２７、６－１２９、６－１３０、６－１３４、６－１３５、６－１３６、６－１３７、６－１３９、６－１４１、６－１４２、６－１４３、６－１４４、６－１４６、６－１４７、６－１４８、６－１５１、６－１５２、６－１５３、６－１５４、６－１５６、６－１５８、６－１５９、６－１６２、６－１６３、６－１６４、６－１６５、６－１６６、６－１６７、６－１６８、６－１６９、６－１７０、６－１７１、６－１７３、６－１７４、６－１７６、６－１７７、６－１７８、６－１７９、６－１８０、６－１８１、６－１８３、６－１８４、６－１８５、６－１８６、６－１８７、６－１８８、６－１８９、６－１９０、６－１９１、６－１９２、６－１９３、６－１９４、６－１９５、６－１９６、６－１９７、６－１９８、６－１９９、６－２００、６－２０１、６－２０２、６－２０３、６－２０４、６－２０５、６－２０６、６－２０７、６－２０８、６－２０９、６－２１０、６－２１１、６－２１２、６－２１３、６－２１５、６－２１６、６－２１７、６－２１８、６－２１９、６－２２１、６－２２２、６－２２３、６－２２４、６－２２５、６－２２６、６－２２７、６－２２８、６－２２９、６－２３０、６－２３１、６－２３２、６－２３３、６－２３４、６－２３５、６－２３６、６－２３７、６－２３８、６－２３９、６－２４０、６－２４１、６－２４２、６－２４３、６－２４４、６－２４５、６－２４６、６－２４７、６－２４８、６－２４９、６－２５０、６－２５１、６－２５２、６－２５３、６－２５４、６－２５５、６－２５６、６－２５７、６－２５８、６－２５９、６－２６０、６－２６１、６－２６２、６－２６３、６－２６４、６－２６５、６－２６６、６－２６７、６－２６８、６－２６９、６－２７０、６－２７１、６－２７２、６－２７３、６－２７５、６－２７６、６－２７７、６－２７８、６－２７９、６－２８０、６－２８１、６－２８２、６－２８３、６－２８４、６－２８５、６－２８６、６－２８７、６－２８８、６－２８９、６－２９０、６－２９１、６－２９２、６－２９３、６－２９４、６－２９５、６－２９６、６－２９７、６－２９８、６－２９９、６－３００、６－３０１、６－３０２、６－３０３、６－３０４、６－３０５、６－３０６、６－３０７、６－３０８、６－３０９、６－３１０、６－３１１、６－３１４、６－３１５、６－３１６、６－３１７、６－３１８、６－３１９、６－３２０、６－３２１、６－３２２、６－３２３、６－３２４、６－３２５、６－３２９、６－３３０、６－３３２、６－３３３、６－３３６、６－３３７、６－３３９、６－３４０、６－３４１、６－３４２、６－３４３、６－３４４、６－３４５、６－３４６、６－３４７、６－３４８、６－３４９、６－３５０、６－３５１、６－３５２、６－３５３、６－３５４、６－３５５、６－３５６、６－３５７、６－３５８、６－３５９、６－３６０、６－３６４、６－３６５、６－３６６、６－３６７、６－３６９、６－３７０、６－３７１、６－３７２、６－３７３、６－３７４、６－３７５、６－３７６、６－３７８、６－３８０、６－３８１、６－３８２、６－３８３、６－３８５、６－３８６、６－３８７、６－３８８、６－３８９、６－３９０、６－３９１、６－３９２、６－３９３、６－３９４、６－３９５、６－３９９、６－４００、６－４０１、６－４０２、６－４０３、６－４０５、６－４０６、６－４０７、６－４０８、６－４０９、６－４１０、６－４１１、６－４１２、６－４１３、６－４１４、６－４１５、６－４１６、６－４１７、６－４１８、６－４１９、７－００１、８－００３、８－００４、８－００５、８－００６、８－００７、８－００８、８－００９、８－０１０、８－０１１、８－０１３、８－０１４、８－０１５、９－００１、９－００２、９－００３、９－００５、９－００６、９－００７、９－００８、９－００９、９－０１０、９－０１１、９－０１２、９－０１３、９－０１６、９－０１７、９－０１８、９－０１９、９－０２０、９－０２１、９－０２２、９－０２３、９－０２４、９－０２５、９－０２６、９－０２９、９－０３０、９－０３１、９－０３２、９－０３３、９－０３４、９－０３５、９－０３６、９－０３７、９－０３８、９－０３９、９－０４０、９－０４１、９－０４２、９－０４３、９－０４４、９－０４５、９－０４６、９－０４７、９－０４８、９－０４９、９－０５０、９－０５１、９－０５２、9-053, 9-054, 9-055, 9-056, 9-057, 9-058, 10-001, 10-002, 10-003.

[0477] Test Example 6 Cucumber anthracnose control effect test 90 cm ３ Cucumbers (variety: Sagamihanjiro) were planted in plastic pots of 100 mm diameter, and at the cotyledon stage, 5 ml of a test solution diluted with water to 500 ppm was sprayed onto the cucumbers. One day after spraying, a conidial suspension of cucumber anthracnose fungus (Colletotrichum lagenarium) was sprayed onto the cucumbers, which were then placed in an inoculation box at 25°C and 100% RH for 2 days. The cucumbers were then placed in an air-conditioned greenhouse (temperature: 23°C, humidity: 60% RH) and maintained there for 7 days. The proportion of lesions formed on the inoculated leaves was measured, and the control value was calculated using the same formula as in Test Example 1.

[0478] As a result, of the compounds tested, the following compounds showed a control value of 70% or more.

[0479] Compounds: No. 1-001, 1-002, 1-003, 1-004, 1-006, 1-007, 1-008, 1-009, 1-010, 1-011, 1-012, 1-013, 1-014, 1-015, 1-016, 1-017, 1-018, 1-019, 1-020, 1-021, 1-0 22, 1-023, 1-024, 1-025, 1-026, 1-027, 1-028, 1-029, 1-030, 2-001, 2-002, 2-003, 2-004, 2-005, 2-006, 2-007, 2-009, 2-010, 2-013, 2-014, 2-015, 2 -016, 2-017, 2-018, 2-019, 2-020, 2-022, 2-023, 2-024, 2-025, 2-027, 2-028, 2-029, 2-030, 2-031, 2-032, 2-033, 2-034, 2-035, 2-036, 2-037, 2-038 , 2-039, 2-040, 2-041, 2-042, 2-043, 2-044, 2-045, 2-046, 3-001, 3-002, 3-003, 3-004, 3-005, 3-006, 3-007, 3-008, 4-004, 4-005, 4-006, 4-007, 4-0 08, 4-009, 5-001, 5-002, 5-003, 5-005, 5-008, 5-009, 5-011, 5-012, 5-014, 5-015, 5-016, 5-017, 5-018, 5-023, 5-024, 5-034, 5-038, 5-040, 5-041, 5-045, 5-056, 5-057, 5-060, 5-061, 5-062, 5-063, 5-064, 5-065, 5-066, 5-067, 5-068, 5-069, 5-070, 5-072, 5-074, 5-077, 5-078, 5-084, 5-085, 5-08 8, 5-089, 5-093, 5-094, 5-097, 5-098, 5-101, 5-102, 5-104, 5-105, 5-108, 5-111, 5-112, 5-113, 5-115, 5-116, 5-117, 5-122, 5-123, 5-126, 5-131, 5- 136, 5-137, 5-138, 6-001, 6-002, 6-003, 6-004, 6-005, 6-006, 6-007, 6-008, 6-009, 6-010, 6-011, 6-013, 6-015, 6-016, 6-017, 6-018, 6-019, 6-020,６－０２１、６－０２３、６－０２４、６－０２５、６－０２６、６－０２７、６－０２８、６－０２９、６－０３０、６－０３１、６－０３２、６－０３３、６－０３４、６－０３５、６－０３６、６－０３７、６－０３８、６－０３９、６－０４０、６－０４１、６－０４２、６－０４３、６－０４４、６－０４５、６－０４６、６－０４７、６－０４８、６－０４９、６－０５０、６－０５１、６－０５２、６－０５３、６－０５４、６－０５５、６－０５６、６－０５７、６－０５８、６－０５９、６－０６０、６－０...

Claims

1. Formula (1): [In formula (1), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula: R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy, R １ａｂ is a hydrogen atom, C １ ~C ６ Alkyl, halogen atom, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) alkyl; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula: Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, Z ２ In the relationship, when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom or a halogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ represents an alkyl group, and Q represents an oxygen atom, a sulfur atom, or NOR ７ represents R ７ is a hydrogen atom or C １ ~C ６ represents alkyl, R ５ are J-1-a, J-2, J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-10, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20, J-21, phenylcarbonyl, -CH ２ R ５ａ , -C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amino, —C(O)R ５ｄ , phenyl, (Z ５ｃ ) ｍ phenyl substituted by -C(=NOR ２ａ ) R ２ｂ , —C(O)NR ５ｃ R ５ｆ , C １ ~C ７ Alkyl or halo(C １ ~C ６ ) alkyl; J-1-a, J-2 to J-13, J-15 to J-18, J-20, and J-21 each represent a structure represented by the following structural formula: Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) Alkyl, E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-13, E-15, E-19, E-22, E-25, E-26, E-27, E-28, E- 29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ represents alkenyl; Z ５ In the relationship, when p2 represents an integer of 2, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p3 represents an integer of 2 or 3, each Z ５ may be the same as or different from each other, Z ５ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ５ may be the same as or different from each other, and E-1 to E-9, E-13, E-15, E-19, E-22, E-25 to E-44, and E-45 each represent a structure represented by the following structural formula: Z ６ is a halogen atom, C １ ~C ６ Alkyl, halo (C １ ~C ６ ) alkyl, C １ ~C ６ Alkoxy, nitro, cyano, C １ ~C ６ Alkoxycarbonyl or C １ ~C ６ represents alkylcarbonyl; Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p7 represents an integer of 2, 3, 4, 5, 6 or 7, each Z ６ may be the same or different from each other, R ５ａａ is a hydrogen atom, C １ ~C ６ Alkyl, phenyl, (Z ５ｃ ) ｍ phenyl substituted by E-1, E-2, E-3, E-9, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkylcarbonyl, halo(C １ ~C ６ ) alkyl, —CH ２ OH, C ３ ~C １０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ represents R ５ａｂ represents a hydrogen atom; ５ａ is (Z ５ａ ) ｍ１ or —NHC(O)OR ５ｆ represents R ５ｂ is (Z ５ｂ ) ｍ１ phenyl, phenyl, substituted by —C(O)R ５ｆ , C １ ~C ６ Alkoxycarbonyl, E-1, phenylcarbonyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｃ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C ３ ~C １０ ) cycloalkyl, E-1, E-3, E-5, E-7, E-10, E-11, E-12, E-13, E-14, E-15, E-16, E-17, E-18, E-19, E-20, E-21, E-22, E-23, E-24, (Z ５ｂ ) ｍ１ phenyl, phenyl, C １ ~C ６ Alkoxy, —OH, halo(C １ ~C ６ ) alkyl or —C(═NH)R ５ｅ E-10 to E-12, E-14, E-16 to E-18, E-20, E-21, E-23 and E-24 represent structures represented by the following structural formulas, respectively: Z ６ In the relationship, when p2 represents an integer of 2, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p3 represents an integer of 2 or 3, each Z ６ may be the same as or different from each other, Z ６ In the relationship, when p4 represents an integer of 2, 3 or 4, each Z ６ may be the same as or different from each other, Z ａ is C １ ~C ６ Alkyl, E-14, C ２ ~C ６ Alkenyl, halo(C １ ~C ６ ) alkyl or R １１ C replaced by １ ~C ６ represents alkyl, R ５ｄ represents L-1 or L-2, and L-1 and L-2 represent structures represented by the following structural formulas: R ５ｅ is (Z ５ｄ ) ｍ１ represents phenyl substituted by R ５ｆ is C １ ~C ６ Alkyl or halo(C １ ~C ６ ) alkyl, R １０ is Halo (C １ ~C ６ ) represents an alkyl or halogen atom; R １１ is cyano, phenyl, (Z ５ｄ ) ｍ1 phenyl substituted by １ ~C ６ Alkylsulfonyl, C １ ~C ６ Alkylthio, -OCOCH ３ , L-3, Di(C １ ~C ６ alkyl)amino, L-2, C １ ~C ６ Alkylcarbonyl, C １ ~C ６ Alkoxycarbonyl, -NHCOCH ３ or C １ ~C ６ L-3 represents a structure represented by the following structural formula: Z ５ａ is Halo (C １ ~C ６ ) alkoxy; when m1 is an integer of 2, 3, 4 or 5, each Z ５ａ may be the same as or different from each other, Z ５ｂ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C １ ~C ６ represents alkylthio, cyano or —OH, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｂ may be the same as or different from each other, Z ５ｃ is a halogen atom, C １ ~C ６ Alkyl or C １ ~C ６ When m is an integer of 2, 3, 4 or 5, each Z ５ｃ may be the same as or different from each other, Z ５ｄ represents a halogen atom, and when m1 represents an integer of 2, 3, 4 or 5, each Z ５ｄ may be the same or different, m and m1 represent an integer of 1, 2 or 3, p1 represents an integer of 0 or 1, p2 represents an integer of 0, 1 or 2, p3 represents an integer of 0, 1, 2 or 3, p4 represents an integer of 0, 1, 2, 3 or 4, and p7 represents an integer of 0, 1, 2, 3, 4, 5, 6 or 7, or a salt thereof.

2. R ５ are J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20, J-21, phenylcarbonyl, -CH ２ R ５ａ , -C(O)NHNHR ５ｂ , -C(O)NHNHC(O)R ５ｂ , —C(O)NHR ５ｃ , C １ ~C ６ Alkoxycarbonyl, —C(O)OR ５ｂ , -C(O)SR ５ｂ , C ２ ~C ６ Alkynyl, —C(O)CH═CHR ５ｂ , -NHR ５ｂ , Ji (C １ ~C ６ alkyl)amino, —C(O)R ５ｄ , phenyl, (Z ５ｃ ) ｍ phenyl substituted by -C(=NOR ２ａ ) R ２ｂ , —C(O)NR ５ｃ R ５ｆ , C １ ~C ７ Alkyl or halo(C １ ~C ６ ) alkyl; p3 represents an integer of 0 or 1; p4 represents an integer of 0, 1 or 2; and p7 represents an integer of 0 or 1. The enamide compound or a salt thereof according to claim 1 .

3. R ２ represents G-2-a, and R ２ａｃ is a halogen atom or C １ ~C ６ represents alkyl, R ２ａｅ represents a hydrogen atom; Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl, halo (C １ ~C ６ ) Alkyl, E-1, E-2, E-3, E-4, E-5, E-6, E-7, E-8, E-9, E-13, E-15, E-19, E-22, E-25, E-26, E-27, E-28, E- 29, E-30, E-31, E-32, E-33, E-34, E-35, E-36, E-37, E-38, E-39, E-40, E-41, E-42, E-43, E-44, E-45, C １ ~C ６ Alkylcarbonyl, C ３ ~C １０ Cycloalkylmethyl, C ３ ~C １０ Cycloalkylethyl, C １ ~C ６ Alkoxymethyl, C １ ~C ６ Alkoxyethyl, R １０ C replaced by ２ ~C ６ Alkenyl, C ２ ~C ６ Alkynyl, R １１ C replaced by １ ~C ６ Alkyl or C ２ ~C ６ The enamide compound or salt thereof according to claim 2, wherein the enamide compound or salt thereof represents alkenyl.

4. Q represents an oxygen atom, and R ５ is J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-11, J-12, J-13, J-15, J-16, J-17, J-18, J-20 or -C(O)NHR ５ｃ The enamide compound or a salt thereof according to claim 3, wherein 5. R ５ represents J-3, J-4, J-5, J-6, J-7, J-8, J-9, J-12, J-15, or J-20, or a salt thereof.

6. R ５ represents J-1-a, J-2, or J-10; p3 represents an integer of 0 or 1; p4 represents an integer of 0, 1, or 2; and p7 represents an integer of 0 or 1. The enamide compound or a salt thereof according to claim 1, 7. R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkylthio group; Q represents an oxygen atom; Z ５ is C １ ~C ６ Alkyl, halogen atom, phenyl, (Z ５ｃ ) ｍ phenyl substituted by ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, E-1, E-2 or E-6; Z ６ is a halogen atom or C １ ~C ６ represents alkyl; Z ５ｃ is a halogen atom or C １ ~C ６ The enamide compound or a salt thereof according to claim 6 , wherein: m represents an alkyl; p1 represents an integer of 1 or 2; p2 represents an integer of 0 or 1; 8. R ２ represents G-2-a, and Z ５ is C １ ~C ６ Alkyl, C ３ ~C １０ Cycloalkyl, halo(C １ ~C ６ ) alkyl, E-1, E-2 or E-6; R ５ａａ is C １ ~C ６ Alkyl, E-1, E-2, E-3, E-9, halo(C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl or -C(=NOR ２ａ ) R ２ｂ The enamide compound or a salt thereof according to claim 7, wherein 9. Formula (1-1a): [In formula (1-1a), R １ represents A-1-a, and A-1-a represents a structure represented by the following structural formula: R １ａａ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, halo (C １ ~C ６ ) alkyl, C ３ ~C １０ Cycloalkyl, C １ ~C ６ Alkylthio, C １ ~C ６ Alkyl sulfonyl, di(C １ ~C ６ alkyl)amino, C ２ ~C ６ Alkenyl, C １ ~C ６ Alkoxymethyl or halo(C １ ~C ６ ) represents alkoxy, R １ａｂ is a hydrogen atom, C １ ~C ６ Alkyl, halogen atom, C １ ~C ６ Alkoxy or halo(C １ ~C ６ ) alkyl; Z １ａ is C １ ~C ６ represents alkyl, R ２ represents G-1-a, G-2-a, G-3, G-4 or G-5, and G-1-a, G-2-a, G-3, G-4 and G-5 each represent a structure represented by the following structural formula: Z ２ represents a halogen atom; Z ２ In the relationship, when p2 represents an integer of 2, each Z ２ may be the same as or different from each other, Z ２ In the relationship, when p3 represents an integer of 2 or 3, each Z ２ may be the same or different from each other, R ２ａａ represents a halogen atom; ２ａｂ represents a hydrogen atom; ２ａｃ represents a hydrogen atom, a halogen atom, or C １ ~C ６ Alkyl, C １ ~C ６ Alkylcarbonyl, —C(═NOR ２ａ ) R ２ｂ , Halo (C １ ~C ６ ) alkyl, cyano, C １ ~C ６ Alkoxy or C １ ~C ６ represents an alkoxycarbonyl; R ２ａｄ represents a hydrogen atom; ２ａｅ represents a hydrogen atom or a halogen atom; ２ａｆ represents a hydrogen atom; ２ａ is C １ ~C ６ represents alkyl, R ２ｂ is C １ ~C ６ represents alkyl; Z ２ａ is C １ ~C ６ p2 represents an integer of 0 or 1, and p3 represents an integer of 0 or 1.

10. R ２ represents G-2-a or G-5.

11. R １ａａ is a halogen atom, C １ ~C ６ Alkyl, C １ ~C ６ Alkoxy, C １ ~C ６ Alkylthio, di(C １ ~C ６ alkyl)amino or halo(C １ ~C ６ ) represents alkoxy, R ２ represents G-2-a, and R ２ａｃ is a halogen atom or C １ ~C ６ represents alkyl, R ２ａｅ The amine compound according to claim 10, wherein represents a hydrogen atom.

12. A pesticide containing, as an active ingredient, one or more enamide compounds and salts thereof according to any one of claims 1 to 8.

13. A fungicide containing, as an active ingredient, one or more enamide compounds and salts thereof according to any one of claims 1 to 8.

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

15. An antifungal agent containing, as an active ingredient, one or more enamide compounds and salts thereof according to any one of claims 1 to 8.

16. An internal parasite control agent containing, as an active ingredient, one or more enamide compounds and salts thereof according to any one of claims 1 to 8.

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