Phenylpyrazole compound and plant disease control method

Abstract

Provided is an excellent control method for plant diseases. (In the formula, Z represents a C6-C10 aryl group or the like, R1 and R2 are the same or different from each other and represent a C1-C6 chain hydrocarbon group or the like, R3 represents a C1-C6 chain hydrocarbon group or the like, adjacent R1 and R3 may form a C4-C7 alicyclic hydrocarbon or the like together with the carbon atoms to which they are bonded, two adjacent R3 and R3 may form a C4-C7 alicyclic hydrocarbon or the like together with the carbon atoms to which they are bonded, p represents 0, 1, 2 or 3, and when p is 2 or 3, p represents 0, 1, 2 or 3. The two or three R3s may be the same as or different from each other. ) The compound, the N-oxide thereof, or a salt thereof can be used for controlling plant diseases. # imgabs0 #

Description

Technical Field

[0001] This application claims priority and the benefits of Japanese Patent Application No. 2022-158301 filed on September 30, 2022, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a phenylpyrazole compound and a method for controlling plant diseases. Background Art

[0003] Patent Documents 1 and 2 describe phenylpyrazole compounds.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 96 / 02138

[0007] Patent Document 2: European Patent Application Publication No. 538156 Summary of the invention

[0008] Problems to be solved by the invention

[0009] An object of the present invention is to provide an excellent control method for plant diseases.

[0010] Means for solving problems

[0011] The inventors of the present application have conducted studies to find an excellent control method for plant diseases, and as a result, have found that a compound represented by the following formula (I) has an excellent control effect on plant diseases.

[0012] That is, the present invention is as follows.

[0013] [1] A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with a compound represented by formula (I) (hereinafter referred to as the present compound N) or its N-oxide or salt thereof (hereinafter referred to as the compound represented by formula (I) or its N-oxide or salt thereof as the present compound).

[0014] [Chemical formula 1]

[0015]

[0016] 〔In the formula,

[0017] Z represents a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group D},

[0018] R 1 and R2 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a hydrogen atom, a halogen atom, a nitro group, a cyano group, NR 8 R 9 , OR 10 、S(O) k R 11 、C(O)R 12 、C(O)OR 13 、C(O)NR 4 R 5 or CR 6 =NOR 7 ,

[0019] R 3 represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a halogen atom, a nitro group, a cyano group, an NR 8 R 9 , OR 10 、S(O) k R 11 、C(O)R 12 、C(O)OR 13 、C(O)NR 4 R 5 or CR 6 =NOR 7 ,

[0020] Adjacent R 1 and R 3 Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}, a benzene ring or a 5-7-membered aromatic heterocycle {the benzene ring and the 5-7-membered aromatic heterocycle may be substituted with one or more substituents selected from Group E},

[0021] Two adjacent R 3 and R 3Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}, a benzene ring or a 5-7-membered aromatic heterocycle {the benzene ring and the 5-7-membered aromatic heterocycle may be substituted with one or more substituents selected from Group E},

[0022] R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C} or a hydrogen atom,

[0023] p represents 0, 1, 2 or 3,

[0024] When p is 2 or 3, 2 or 3 R 3 may be the same as or different from each other, and k represents 0, 1 or 2.

[0025] Group A: a group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from group C}, a halogen atom and a cyano group.

[0026] Group B: A group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0027] Group C: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0028] Group D: A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0029] Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group. 〕

[0030] [2] The method for controlling plant diseases as described in [1], wherein the compound represented by formula (I) or its N-oxide or its salt is the following compound or its N-oxide or its salt, wherein:

[0031] Z is a phenyl group or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D},

[0032] R 1 and R 2 is a hydrogen atom,

[0033] R 3 is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8 R 9 , OR 10 , SR 11 、C(O)OR 13 or C(O)NR 4 R 5 ,

[0034] Two adjacent R 3 and R 3 Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle, or a 5-7-membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7-membered non-aromatic heterocycle, and the 5-7-membered aromatic heterocycle may be substituted with one or more halogen atoms},

[0035] R 4 , R 5 , R 8 , R 9 , R 10 , R 11 and R 13 The same or different from each other are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, phenyl groups or hydrogen atoms.

[0036] [3] The method for controlling plant diseases as described in [1] or [2], wherein the compound represented by formula (I) or its N-oxide or salt thereof is a compound in which Z is a phenyl group or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group F}, R 1 and R 2 is a compound containing a hydrogen atom or its N-oxide or a salt thereof,

[0037] Group F: A group consisting of a C1-C6 chain hydrocarbon group and a halogen atom.

[0038] [4] A compound represented by formula (II) (excluding 4-{[3-(4-fluorophenyl)-1H-pyrazol-1-yl]sulfonyl}-1,3-dimethyl-1H-pyrazole and 3-(2,3-dihydrobenzofuran-5-yl)-1-(thiophen-2-ylsulfonyl)-1H-pyrazole) (hereinafter referred to as the compound of the present invention N) or its N-oxide or a salt thereof (hereinafter, the compound represented by formula (II) or its N-oxide or a salt thereof is referred to as the compound of the present invention).

[0039] [Chemical formula 2]

[0040]

[0041] 〔In the formula,

[0042] Z a Indicates that it can be selected from group D a A 5-10 membered aromatic heterocyclic group substituted with one or more substituents in

[0043] R 1a and R 2a The same or different from each other, indicating that they can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C asubstituted with one or more substituents in}, hydrogen atom, halogen atom, nitro group, cyano group, NR 8a R 9a , OR 10a 、S(O) m R 11a 、C(O)R 12a 、C(O)OR 13a 、C(O)NR 4a R 5a or CR 6a =NOR 7a ,

[0044] R 3a Indicates that it can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C a substituted with one or more substituents in}, halogen atoms, nitro, cyano, NR 8a R 9a , OR 10a 、S(O) m R 11a 、C(O)R 12a 、C(O)OR 13a 、C(O)NR 4a R 5a or CR 6a =NOR 7a ,

[0045] Adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they can form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a substituted with one or more substituents in},

[0046] Two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they can form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B asubstituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a substituted with one or more substituents in},

[0047] R 4a , R 5a , R 6a , R 7a , R 8a , R 9a , R 10a , R 11a , R 12a and R 13a The same or different from each other, indicating that they can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C a One or more substituents in {} or a hydrogen atom,

[0048] q means 1, 2 or 3,

[0049] When q is 2 or 3, 2 or 3 R 3a may be the same as or different from each other, and m represents 0, 1 or 2.

[0050] Group A a : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the 3-8 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be selected from the group C a The group consisting of one or more substituents in the formula (a) is substituted with a halogen atom and a cyano group.

[0051] Group B a : A group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0052] Group C a: A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0053] Group D a : A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

[0054] Group E a : A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group. 〕

[0055] [5] The compound or N-oxide thereof or a salt thereof as described in [4], wherein Z a can be selected from group F a A 5-6 membered aromatic heterocyclic group substituted with one or more substituents in

[0056] R 1a and R 2a is a hydrogen atom,

[0057] Group F a : A group consisting of a C1-C6 chain hydrocarbon group and a halogen atom.

[0058] [6] The compound described in [4] or [5], or its N-oxide or salt thereof, wherein R 3a is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8a R 9a , OR 10a or SR 11a ,

[0059] Two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle, or a 5-7-membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7-membered non-aromatic heterocycle, and the 5-7-membered aromatic heterocycle may be substituted with one or more halogen atoms},

[0060] R 8a , R 9a , R 10a and R 11a The same or different from each other are C1-C6 chain hydrocarbon groups.

[0061] [7] A composition comprising an inactive support and the compound or its N-oxide or salt thereof according to any one of [4] to [6].

[0062] [8] A composition comprising one or more components selected from the group consisting of Group (a), Group (b), Group (c) and Group (d), and the compound or its N-oxide or salt thereof described in any one of [4] to [6],

[0063] Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients;

[0064] Group (b): fungicidal active ingredients;

[0065] Group (c): plant growth regulating ingredients;

[0066] Group (d): repellent ingredients.

[0067] [9] A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with an effective amount of the compound or its N-oxide or salt thereof according to any one of [4] to [6] or an effective amount of the composition according to [8].

[0068]

[10] Use of the compound according to any one of [4] to [6], its N-oxide or salt thereof, or the composition according to [8] for controlling plant diseases.

[0069]

[11] Seeds or vegetative propagation organs, which contain an effective amount of the compound described in any one of [4] to [6] or its N-oxide or salt thereof, or an effective amount of the composition described in [8].

[0070]

[12] A compound represented by formula (III) (hereinafter referred to as intermediate A).

[0071] [Chemical formula 3]

[0072]

[0073] 〔In the formula,

[0074] Z b Indicates that it can be selected from group D b A 5-10 membered aromatic heterocyclic group substituted with one or more substituents in

[0075] Xb Represents chlorine atom, bromine atom, iodine atom, B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl.

[0076] Group D b : A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group. 〕

[0077] Effects of the Invention

[0078] The present invention can prevent and control plant diseases. DETAILED DESCRIPTION

[0079] The substituents in the present invention are explained.

[0080] The halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0081] When the substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0082] Regarding the term "may be substituted with one or more substituents selected from Group X" in this specification (X refers to A, B, C, D, E, F, A a , B a , C a , D a 、E a 、F a , D b 、F b 、B2 a 、D2 a 、D3 a , B2 and D2), when there are two or more substituents selected from group X, these substituents may be the same or different.

[0083] In the present specification, the expression "CX-CY" means that the number of carbon atoms is X to Y. For example, the expression "C1-C6" means that the number of carbon atoms is 1 to 6.

[0084] The chain hydrocarbon group refers to an alkyl group, an alkenyl group or an alkynyl group.

[0085] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0086] Examples of the alkenyl group include ethenyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl.

[0087] Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 2-butynyl group, a 4-pentynyl group, and a 5-hexynyl group.

[0088] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.

[0089] Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, an isopropylsulfanyl group, and a hexylsulfanyl group.

[0090] Examples of the alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, an isopropylsulfinyl group, and a hexylsulfinyl group.

[0091] Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an isopropylsulfonyl group, and a hexylsulfonyl group.

[0092] Examples of the alkylcarbonyl group include an acetyl group and a propionyl group.

[0093] Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an isopropoxycarbonyl group, and a hexyloxycarbonyl group.

[0094] Examples of the alicyclic hydrocarbon include a cyclobutene ring, a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, and a cycloheptene ring.

[0095] Examples of the alicyclic hydrocarbon group include a cycloalkyl group and a cycloalkenyl group.

[0096] Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0097] Examples of the cycloalkenyl group include a cyclopentenyl group and a cyclohexenyl group.

[0098] Examples of the aryl group include a phenyl group and a naphthyl group.

[0099] Examples of the non-aromatic heterocyclic ring include a dihydrofuran ring, a dihydrothiophene ring, a dihydropyrrole ring, a 1,3-dioxole ring, a pyran ring, and a dihydropyran ring.

[0100] Examples of the aromatic heterocyclic ring include a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring and a pyrazine ring.

[0101] Examples of the aromatic heterocyclic group include 5-membered aromatic heterocyclic groups such as pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl and thiadiazolyl; 6-membered aromatic heterocyclic groups such as pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl and tetrazinyl; and bicyclic aromatic heterocyclic groups such as benzofuranyl.

[0102] Examples of the non-aromatic heterocyclic group include aziridinyl, oxirane, thiirane, azetidinyl, oxetanyl, thietanyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, pyrazolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, thiazolinyl, oxazolidinyl, thiazolidinyl, isoxazolinyl, isoxazolidinyl, isothiazolinyl, isothiazolidinyl, dioxolanyl, dioxhexyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, azepanyl, oxepanyl and thiepanyl.

[0103] 4-{[3-(4-fluorophenyl)-1H-pyrazol-1-yl]sulfonyl}-1,3-dimethyl-1H-pyrazole is a compound represented by the following formula.

[0104] [Chemical formula 4]

[0105]

[0106] 3-(2,3-Dihydrobenzofuran-5-yl)-1-(thiophen-2-ylsulfonyl)-1H-pyrazole is a compound represented by the following formula.

[0107] [Chemical formula 5]

[0108]

[0109] The N-oxide of the compound represented by formula (I) or formula (II) refers to a structure in which at least one nitrogen atom contained in the compound represented by formula (I) or formula (II) is substituted with an oxo group.

[0110] The present compound or the compound of the present invention may exist in more than one stereoisomer. Examples of stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. The present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0111] The compound represented by formula (I) or formula (II) or its N-oxide may be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, benzoic acid, etc. to form an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate, benzoate, etc.

[0112] In this compound, adjacent R 1 and R 3 The compounds that form, together with the carbon atoms to which they are bonded, a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted with one or more substituents selected from group E} are specifically the following compounds:

[0113] [Chemical formula 6]

[0114]

[0115] In formula (IA-1),

[0116] R 2 and Z has the same meaning as in [1],

[0117] R 3B and R 3C The same or different from each other, indicating that the R 3 Same meaning or hydrogen atom,

[0118] R 1 and R 3A Compounds which, together with the carbon atoms to which they are bonded, form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted with one or more substituents selected from group E}.

[0119] In this compound, two adjacent R 3 and R 3 The compounds that form, together with the carbon atoms to which they are bonded, a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted with one or more substituents selected from group E} are specifically the following compounds:

[0120] 1) In formula (IA-1),

[0121] R 1 , R 2 and Z has the same meaning as in [1],

[0122] R 3C Represents R with [1] 3 Same meaning or hydrogen atom,

[0123] R 3A and R 3B A compound which, together with the carbon atoms to which they are bonded, forms a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted with one or more substituents selected from Group E}; or

[0124] 2) In formula (IA-1),

[0125] R 1 , R 2 and Z has the same meaning as in [1],

[0126] R 3A Represents R with [1] 3 Same meaning or hydrogen atom,

[0127] R 3B and R 3C Compounds which, together with the carbon atoms to which they are bonded, form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted with one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted with one or more substituents selected from group E}.

[0128] In the compounds of the present invention, adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a Specifically, the compound wherein the compound is substituted with one or more substituents in is the following compound:

[0129] [Chemical formula 7]

[0130]

[0131] In formula (IIA-1),

[0132] R 2a and Z a It has the same meaning as [4],

[0133] R 3aB and R 3aCThe same or different from each other, indicating that the R 3a Same meaning or hydrogen atom,

[0134] R 1a and R 3aA Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a The compound is substituted with one or more substituents in .

[0135] In the compounds of the present invention, two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a Specifically, the compound wherein the compound is substituted with one or more substituents in is the following compound:

[0136] 1) In formula (IIA-1),

[0137] R 1a , R 2a and Z a It has the same meaning as [4],

[0138] R 3aC Represents R with [4] 3a Same meaning or hydrogen atom,

[0139] R 3aA and R 3aB Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a A compound wherein the compound is substituted with one or more substituents in

[0140] 2) In formula (IIA-1),

[0141] R 1a , R 2a and Z a It has the same meaning as [4],

[0142] R 3aA Represents R with [4] 3a Same meaning or hydrogen atom,

[0143] R 3aB and R 3aC Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a The compound is substituted with one or more substituents in .

[0144] As an embodiment of the present compound N, the following compounds can be mentioned.

[0145] [Form 1] In the present compound N, R 3 The compound is a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group A, or a C3-C8 alicyclic hydrocarbon group which may be substituted by one or more halogen atoms.

[0146] [Form 2] In the present compound N, R 3 A compound containing halogen atoms.

[0147] [Form 3] In the present compound N, R 3 Nitro, NR 8 R 9 or C(O)NR 4 R 5 , R 4 , R 5 , R 8 and R 9 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0148] [Form 4] In the present compound N, R 3 is a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group A, a C3-C8 alicyclic hydrocarbon group which may be substituted by one or more halogen atoms, a halogen atom, a nitro group, NR 8 R 9 or C(O)NR 4 R 5 , R 4 , R 5 , R 8 and R 9 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0149] [Form 5] In the present compound N, adjacent R 1 and R 3 Together with the carbon atoms to which they are bonded, they form a compound of a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted by one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted by one or more substituents selected from group E}.

[0150] [Form 6] In the present compound N, adjacent R 1 and R 3 Compounds which, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B2}.

[0151] Group B2: A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, and a halogen atom.

[0152] [Form 7] In the present compound N, adjacent R 1 and R 3 A compound that forms a benzene ring or a 5- to 6-membered aromatic heterocyclic ring together with the carbon atoms to which they are bonded {the benzene ring and the 5- to 6-membered aromatic heterocyclic ring may be substituted with one or more substituents selected from Group B2}.

[0153] [Embodiment 8] In the present compound N, two adjacent R 3 and R 3 Together with the carbon atoms to which they are bonded, they form a compound of a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle may be substituted by one or more substituents selected from group B}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be substituted by one or more substituents selected from group E}.

[0154] [Form 9] In the present compound N, two adjacent R 3 and R 3 Compounds which, together with the carbon atoms to which they are bonded, form a C5-C6 alicyclic hydrocarbon or a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B2}.

[0155] [Embodiment 10] In the present compound N, two adjacent R 3 and R 3A compound that forms a benzene ring or a 5- to 6-membered aromatic heterocyclic ring together with the carbon atoms to which they are bonded {the benzene ring and the 5- to 6-membered aromatic heterocyclic ring may be substituted with one or more substituents selected from Group B2}.

[0156] [Embodiment 11] In the present compound N, two adjacent R 3 and R 3 A compound which, together with the carbon atoms to which they are bonded, forms a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle, a benzene ring or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle, the benzene ring and the 5-6-membered aromatic heterocycle may be substituted by one or more substituents selected from group B2}.

[0157] [Form 12] In the present compound N, R 3 is a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group A, a C1-C3 alkoxy group, a C3-C8 alicyclic hydrocarbon group {the C1-C3 alkoxy group and the C3-C8 alicyclic hydrocarbon group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group, NR 8 R 9 or C(O)NR 4 R 5 , R 4 , R 5 , R 8 and R 9 The compounds are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom.

[0158] [Form 13] In the present compound N, R 3 is a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms}, a cyclopropyl group, a halogen atom, a nitro group, a NR 8 R 9 or C(O)NR 4 R 5 , R 4 , R 5 , R 8 and R 9 The compounds are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom.

[0159] [Form 14] In the present compound N, R 3 is a C1-C6 chain hydrocarbon group which may be substituted by one or more substituents selected from Group A, a C1-C3 alkoxy group, a C3-C8 alicyclic hydrocarbon group {the C1-C3 alkoxy group and the C3-C8 alicyclic hydrocarbon group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group, NR 8 R 9 or C(O)NR4 R 5 , R 4 , R 5 , R 8 and R 9 are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom, or two adjacent R 3 and R 3 Compounds which can form, together with the carbon atoms to which they are bonded, a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle, a benzene ring or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle, the benzene ring and the 5-6-membered aromatic heterocycle can be substituted with one or more substituents selected from group B2}.

[0160] [Form 15] In the present compound N, R 3 is a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms}, a cyclopropyl group, a halogen atom, a nitro group, a NR 8 R 9 or C(O)NR 4 R 5 , R 4 , R 5 , R 8 and R 9 are the same or different from each other and are hydrogen atoms, cyclopropyl groups or C1-C3 alkyl groups, or two adjacent R 3 and R 3 Compounds which can form, together with the carbon atoms to which they are bonded, a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle and the 5-6-membered aromatic heterocycle can be substituted with one or more substituents selected from Group B2}.

[0161] [Form 16] In the present compound N, p is 0.

[0162] [Form 17] In the present compound N, p is 1.

[0163] [Form 18] In the present compound N, p is 2.

[0164] [Form 19] In the present compound N, p is 3.

[0165] [Form 20] In the present compound N, p is 1, 2 or 3.

[0166] [Form 21] The compound in Form 1, wherein p is 1.

[0167] [Form 22] The compound in Form 1, wherein p is 2.

[0168] [Form 23] The compound in Form 1, wherein p is 3.

[0169] [Form 24] The compound in Form 1, wherein p is 1, 2 or 3.

[0170] [Form 25] The compound in Form 2, wherein p is 1.

[0171] [Form 26] The compound in Form 2, wherein p is 2.

[0172] [Form 27] ​​The compound in Form 2, wherein p is 3.

[0173] [Form 28] The compound in Form 2, wherein p is 1, 2 or 3.

[0174] [Form 29] The compound in Form 3, wherein p is 1.

[0175] [Form 30] The compound in Form 3, wherein p is 2.

[0176] [Form 31] The compound in Form 3, wherein p is 3.

[0177] [Embodiment 32] The compound in Embodiment 3, wherein p is 1, 2 or 3. [Embodiment 33] The compound in Embodiment 4, wherein p is 1.

[0178] [Form 34] The compound in Form 4, wherein p is 2.

[0179] [Form 35] The compound in Form 4, wherein p is 3.

[0180] [Embodiment 36] The compound in Embodiment 4, wherein p is 1, 2 or 3. [Embodiment 37] The compound in Embodiment 5, wherein p is 1.

[0181] [Form 38] The compound in Form 5, wherein p is 2.

[0182] [Form 39] The compound in Form 5, wherein p is 3.

[0183] [Embodiment 40] The compound in Embodiment 5, wherein p is 1, 2 or 3. [Embodiment 41] The compound in Embodiment 6, wherein p is 1.

[0184] [Form 42] The compound in Form 6, wherein p is 2.

[0185] [Form 43] The compound in Form 6, wherein p is 3.

[0186] [Embodiment 44] The compound in Embodiment 6, wherein p is 1, 2 or 3. [Embodiment 45] The compound in Embodiment 7, wherein p is 1.

[0187] [Form 46] The compound in Form 7, wherein p is 2.

[0188] [Form 47] The compound in Form 7, wherein p is 3.

[0189] [Embodiment 48] The compound in Embodiment 7, wherein p is 1, 2 or 3. [Embodiment 49] The compound in Embodiment 8, wherein p is 2.

[0190] [Form 50] The compound in Form 8, wherein p is 3.

[0191] [Form 51] The compound in Form 8, wherein p is 2 or 3.

[0192] [Form 52] The compound in Form 9, wherein p is 2.

[0193] [Form 53] The compound in Form 9, wherein p is 3.

[0194] [Form 54] The compound in Form 9, wherein p is 2 or 3.

[0195] [Form 55] The compound in Form 10, wherein p is 2.

[0196] [Form 56] The compound in Form 10, wherein p is 3.

[0197] [Embodiment 57] The compound in Embodiment 10, wherein p is 2 or 3. [Embodiment 58] The compound in Embodiment 11, wherein p is 2.

[0198] [Form 59] The compound in Form 11, wherein p is 3.

[0199] [Form 60] The compound in Form 11, wherein p is 2 or 3.

[0200] [Form 61] The compound in Form 12, wherein p is 1.

[0201] [Form 62] The compound in Form 12, wherein p is 2.

[0202] [Form 63] The compound in Form 12, wherein p is 3.

[0203] [Form 64] The compound in Form 12, wherein p is 1, 2 or 3.

[0204] [Form 65] The compound in Form 13, wherein p is 1.

[0205] [Form 66] The compound in Form 13, wherein p is 2.

[0206] [Form 67] The compound in Form 13, wherein p is 3.

[0207] [Form 68] The compound in Form 13, wherein p is 1, 2 or 3.

[0208] [Form 69] The compound in Form 14, wherein p is 1.

[0209] [Form 70] The compound in Form 14, wherein p is 2.

[0210] [Form 71] The compound in Form 14, wherein p is 3.

[0211] [Form 72] The compound in Form 14, wherein p is 1, 2 or 3.

[0212] [Form 73] The compound in Form 15, wherein p is 1.

[0213] [Form 74] The compound in Form 15, wherein p is 2.

[0214] [Form 75] The compound in Form 15, wherein p is 3.

[0215] [Form 76] The compound in Form 15, wherein p is 1, 2 or 3.

[0216] [Embodiment 77] In the present compound N, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0217] [Method 78] In method 1, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0218] [Method 79] In method 2, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0219] [Method 80] In method 3, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0220] [Method 81] In method 4, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0221] [Method 82] In method 5, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0222] [Method 83] In method 6, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0223] [Method 84] In method 7, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0224] [Method 85] In method 8, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0225] [Method 86] In method 9, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0226] [Method 87] In method 10, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0227] [Method 88] In method 11, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0228] [Method 89] In method 12, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0229] [Method 90] In method 13, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0230] [Method 91] In method 14, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0231] [Method 92] In method 15, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0232] [Method 93] In method 16, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0233] [Method 94] In method 17, R 1 and R 2The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0234] [Method 95] In method 18, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0235] [Method 96] In method 19, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0236] [Method 97] In method 20, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0237] [Method 98] In method 21, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0238] [Method 99] In method 22, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0239] [Method 100] In method 23, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0240] [Method 101] In method 24, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0241] [Method 102] In method 25, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0242] [Method 103] In method 26, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0243] [Method 104] In method 27, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0244] [Method 105] In method 28, R1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0245] [Method 106] In method 29, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0246] [Method 107] In method 30, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0247] [Method 108] In method 31, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0248] [Method 109] In method 32, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0249] [Method 110] In method 33, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0250] [Method 111] In method 34, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0251] [Method 112] In method 35, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0252] [Method 113] In method 36, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0253] [Method 114] In method 37, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0254] [Method 115] In method 38, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0255] [Method 116] In method 39, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0256] [Method 117] In method 40, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0257] [Method 118] In method 41, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0258] [Method 119] In method 42, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0259] [Method 120] In method 43, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0260] [Method 121] In method 44, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0261] [Method 122] In method 45, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0262] [Method 123] In method 46, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0263] [Method 124] In method 47, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0264] [Method 125] In method 48, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0265] [Method 126] In method 49, R 1 and R2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0266] [Method 127] In method 50, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0267] [Method 128] In method 51, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0268] [Method 129] In method 52, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0269] [Method 130] In method 53, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0270] [Method 131] In method 54, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0271] [Method 132] In method 55, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0272] [Method 133] In method 56, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0273] [Method 134] In method 57, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0274] [Method 135] In method 58, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0275] [Method 136] In method 59, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0276] [Method 137] In method 60, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0277] [Method 138] In method 61, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0278] [Method 139] In method 62, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0279] [Method 140] In method 63, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0280] [Method 141] In method 64, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0281] [Method 142] In method 65, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0282] [Method 143] In method 66, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0283] [Method 144] In method 67, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0284] [Method 145] In method 68, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0285] [Method 146] In method 69, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0286] [Method 147] In method 70, R 1 and R 2The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0287] [Method 148] In method 71, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0288] [Method 149] In method 72, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0289] [Method 150] In method 73, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0290] [Method 151] In method 74, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0291] [Method 152] In method 75, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0292] [Method 153] In method 76, R 1 and R 2 The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0293] [Embodiment 154] In the present compound N, R 1 and R 2 A compound containing hydrogen atoms.

[0294] [Method 155] In method 1, R 1 and R 2 A compound containing hydrogen atoms.

[0295] [Method 156] In method 2, R 1 and R 2 A compound containing hydrogen atoms.

[0296] [Method 157] In method 3, R 1 and R 2 A compound containing hydrogen atoms.

[0297] [Method 158] In method 4, R 1 and R 2 A compound containing hydrogen atoms.

[0298] [Method 159] In method 5, R 1 and R 2 A compound containing hydrogen atoms.

[0299] [Method 160] In method 6, R 1 and R 2 A compound containing hydrogen atoms.

[0300] [Method 161] In method 7, R 1 and R 2 A compound containing hydrogen atoms.

[0301] [Method 162] In method 8, R 1 and R 2 A compound containing hydrogen atoms.

[0302] [Method 163] In method 9, R 1 and R 2 A compound containing hydrogen atoms.

[0303] [Method 164] In method 10, R 1 and R 2 A compound containing hydrogen atoms.

[0304] [Method 165] In method 11, R 1 and R 2 A compound containing hydrogen atoms.

[0305] [Method 166] In method 12, R 1 and R 2 A compound containing hydrogen atoms.

[0306] [Method 167] In method 13, R 1 and R 2 A compound containing hydrogen atoms.

[0307] [Method 168] In method 14, R 1 and R 2 A compound containing hydrogen atoms.

[0308] [Method 169] In method 15, R 1 and R 2 A compound containing hydrogen atoms.

[0309] [Method 170] In method 16, R 1 and R 2 A compound containing hydrogen atoms.

[0310] [Method 171] In method 17, R 1 and R 2 A compound containing hydrogen atoms.

[0311] [Method 172] In method 18, R 1 and R 2 A compound containing hydrogen atoms.

[0312] [Method 173] In method 19, R 1 and R 2 A compound containing hydrogen atoms.

[0313] [Method 174] In method 20, R 1 and R 2 A compound containing hydrogen atoms.

[0314] [Method 175] In method 21, R 1 and R 2 A compound containing hydrogen atoms.

[0315] [Method 176] In method 22, R 1 and R 2 A compound containing hydrogen atoms.

[0316] [Method 177] In method 23, R 1 and R 2 A compound containing hydrogen atoms.

[0317] [Method 178] In method 24, R 1 and R 2 A compound containing hydrogen atoms.

[0318] [Method 179] In method 25, R 1 and R 2 A compound containing hydrogen atoms.

[0319] [Method 180] In method 26, R 1 and R 2 A compound containing hydrogen atoms.

[0320] [Method 181] In method 27, R 1 and R 2 A compound containing hydrogen atoms.

[0321] [Method 182] In method 28, R 1 and R 2 A compound containing hydrogen atoms.

[0322] [Method 183] In method 29, R 1 and R 2 A compound containing hydrogen atoms.

[0323] [Method 184] In method 30, R 1 and R 2 A compound containing hydrogen atoms.

[0324] [Method 185] In method 31, R 1 and R 2 A compound containing hydrogen atoms.

[0325] [Method 186] In method 32, R 1 and R 2 A compound containing hydrogen atoms.

[0326] [Method 187] In method 33, R 1 and R 2 A compound containing hydrogen atoms.

[0327] [Method 188] In method 34, R 1 and R 2 A compound containing hydrogen atoms.

[0328] [Method 189] In method 35, R 1 and R 2 A compound containing hydrogen atoms.

[0329] [Method 190] In method 36, R 1 and R 2 A compound containing hydrogen atoms.

[0330] [Method 191] In method 37, R 1 and R 2 A compound containing hydrogen atoms.

[0331] [Method 192] In method 38, R 1 and R 2 A compound containing hydrogen atoms.

[0332] [Method 193] In method 39, R 1 and R 2 A compound containing hydrogen atoms.

[0333] [Method 194] In method 40, R 1 and R 2 A compound containing hydrogen atoms.

[0334] [Method 195] In method 41, R 1 and R 2 A compound containing hydrogen atoms.

[0335] [Method 196] In method 42, R 1 and R 2 A compound containing hydrogen atoms.

[0336] [Method 197] In method 43, R 1 and R 2 A compound containing hydrogen atoms.

[0337] [Method 198] In method 44, R 1 and R 2 A compound containing hydrogen atoms.

[0338] [Method 199] In method 45, R 1 and R 2 A compound containing hydrogen atoms.

[0339] [Method 200] In method 46, R 1 and R 2 A compound containing hydrogen atoms.

[0340] [Method 201] In method 47, R 1 and R 2 A compound containing hydrogen atoms.

[0341] [Method 202] In method 48, R 1 and R 2 A compound containing hydrogen atoms.

[0342] [Method 203] In method 49, R 1 and R 2 A compound containing hydrogen atoms.

[0343] [Method 204] In method 50, R 1 and R 2 A compound containing hydrogen atoms.

[0344] [Method 205] In method 51, R 1 and R 2 A compound containing hydrogen atoms.

[0345] [Method 206] In method 52, R 1 and R 2 A compound containing hydrogen atoms.

[0346] [Method 207] In method 53, R 1 and R 2 A compound containing hydrogen atoms.

[0347] [Method 208] In method 54, R 1 and R 2 A compound containing hydrogen atoms.

[0348] [Method 209] In method 55, R 1 and R 2 A compound containing hydrogen atoms.

[0349] [Method 210] In method 56, R 1 and R 2 A compound containing hydrogen atoms.

[0350] [Method 211] In method 57, R 1 and R 2 A compound containing hydrogen atoms.

[0351] [Method 212] In method 58, R 1 and R 2 A compound containing hydrogen atoms.

[0352] [Method 213] In method 59, R 1 and R 2 A compound containing hydrogen atoms.

[0353] [Method 214] In method 60, R 1 and R 2 A compound containing hydrogen atoms.

[0354] [Method 215] In method 61, R 1 and R 2 A compound containing hydrogen atoms.

[0355] [Method 216] In method 62, R 1 and R 2 A compound containing hydrogen atoms.

[0356] [Method 217] In method 63, R 1 and R 2 A compound containing hydrogen atoms.

[0357] [Method 218] In method 64, R 1 and R 2 A compound containing hydrogen atoms.

[0358] [Method 219] In method 65, R 1 and R 2 A compound containing hydrogen atoms.

[0359] [Method 220] In method 66, R 1 and R 2 A compound containing hydrogen atoms.

[0360] [Method 221] In method 67, R 1 and R 2 A compound containing hydrogen atoms.

[0361] [Method 222] In method 68, R 1 and R 2 A compound containing hydrogen atoms.

[0362] [Method 223] In method 69, R 1 and R 2 A compound containing hydrogen atoms.

[0363] [Method 224] In method 70, R 1 and R 2 A compound containing hydrogen atoms.

[0364] [Method 225] In method 71, R 1 and R 2 A compound containing hydrogen atoms.

[0365] [Method 226] In method 72, R 1 and R 2 A compound containing hydrogen atoms.

[0366] [Method 227] In method 73, R 1 and R 2 A compound containing hydrogen atoms.

[0367] [Method 228] In method 74, R 1 and R 2 A compound containing hydrogen atoms.

[0368] [Method 229] In method 75, R 1 and R 2 A compound containing hydrogen atoms.

[0369] [Method 230] In method 76, R 1 and R 2 A compound containing hydrogen atoms.

[0370] [Embodiment 231] In the present compound N, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0371] [Method 232] In method 1, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0372] [Method 233] In method 2, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0373] [Method 234] In method 3, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0374] [Method 235] In method 4, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0375] [Method 236] In method 5, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0376] [Method 237] In method 6, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0377] [Method 238] In method 7, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0378] [Method 239] In method 8, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0379] [Method 240] In method 9, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0380] [Method 241] In method 10, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0381] [Method 242] In method 11, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0382] [Method 243] In method 12, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0383] [Method 244] In method 13, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0384] [Method 245] In method 14, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0385] [Method 246] In method 15, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0386] [Method 247] In method 16, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0387] [Method 248] In method 17, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0388] [Method 249] In method 18, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0389] [Method 250] In method 19, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0390] [Method 251] In method 20, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0391] [Method 252] In method 21, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0392] [Method 253] In method 22, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0393] [Method 254] In method 23, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0394] [Method 255] In method 24, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0395] [Method 256] In method 25, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0396] [Method 257] In method 26, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0397] [Method 258] In method 27, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0398] [Method 259] In method 28, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0399] [Method 260] In method 29, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0400] [Method 261] In method 30, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0401] [Method 262] In method 31, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0402] [Method 263] In method 32, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0403] [Method 264] In method 33, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0404] [Method 265] In method 34, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0405] [Method 266] In method 35, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0406] [Method 267] In method 36, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0407] [Method 268] In method 37, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0408] [Method 269] In method 38, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0409] [Method 270] In method 39, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0410] [Method 271] In method 40, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0411] [Method 272] In method 41, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0412] [Method 273] In method 42, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0413] [Method 274] In method 43, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0414] [Method 275] In method 44, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0415] [Method 276] In method 45, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0416] [Method 277] In method 46, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0417] [Method 278] In method 47, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0418] [Method 279] In method 48, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0419] [Method 280] In method 49, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0420] [Method 281] In method 50, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0421] [Method 282] In method 51, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0422] [Method 283] In method 52, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0423] [Method 284] In method 53, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0424] [Method 285] In method 54, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0425] [Method 286] In method 55, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0426] [Method 287] In method 56, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0427] [Method 288] In method 57, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0428] [Method 289] In method 58, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0429] [Method 290] In method 59, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0430] [Method 291] In method 60, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0431] [Method 292] In method 61, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0432] [Method 293] In method 62, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0433] [Method 294] In method 63, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0434] [Method 295] In method 64, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0435] [Method 296] In method 65, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0436] [Method 297] In method 66, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0437] [Method 298] In method 67, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0438] [Method 299] In method 68, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0439] [Method 300] In method 69, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0440] [Method 301] In method 70, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0441] [Method 302] In method 71, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0442] [Method 303] In method 72, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0443] [Method 304] In method 73, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0444] [Method 305] In method 74, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0445] [Method 306] In method 75, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0446] [Method 307] In method 76, R 1 and R 2 A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0447] [Embodiment 308] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a phenyl group which may be substituted with one or more substituents selected from Group D.

[0448] [Embodiment 309] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a 5- to 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D.

[0449] [Embodiment 310] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a 5-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D.

[0450] [Embodiment 311] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D.

[0451] [Embodiment 312] The compound according to any one of the present compound N or Embodiments 1 to 307, wherein Z is a phenyl group which may be substituted with one or more substituents selected from Group D2.

[0452] Group D2: a group consisting of a C1-C3 alkyl group, a halogen atom and a cyano group.

[0453] [Embodiment 313] The compound according to any one of the present compound N or Embodiments 1 to 307, wherein Z is a 5- to 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D2.

[0454] [Embodiment 314] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a 5-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D2.

[0455] [Embodiment 315] In the present compound N or any one of Embodiments 1 to 307, the compound wherein Z is a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group D2.

[0456] [Embodiment 316] In the present compound N or any one of Embodiments 1 to 307, Z is a 5-6-membered aromatic heterocyclic group {wherein the atom in the 5-6-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D.}.

[0457] [Embodiment 317] The compound according to any one of the present compound N or Embodiments 1 to 307, wherein Z is a phenyl group or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}.

[0458] [Embodiment 318] The compound according to any one of the present compound N or Embodiments 1 to 307, wherein Z is a phenyl group or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D2}.

[0459] [Form 319] In the present compound N or any one of Forms 1 to 307, Z is a phenyl group which may be substituted with one or more substituents selected from Group D2, or a 5-6-membered aromatic heterocyclic group {wherein the atom in the 5-6-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D2}.

[0460] [Form 320] In the present compound N or any one of Forms 1 to 307, Z is a 5-membered aromatic heterocyclic group {wherein the atom in the 5-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 5-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D.}.

[0461] [Form 321] In the present compound N or any one of Forms 1 to 307, Z is a 6-membered aromatic heterocyclic group {wherein the atom in the 6-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D.}.

[0462] [Embodiment 322] In the present compound N or any one of Embodiments 1 to 307, Z is a 5-membered aromatic heterocyclic group {wherein the atom in the 5-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 5-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D2.}.

[0463] [Embodiment 323] In the present compound N or any one of Embodiments 1 to 307, Z is a 6-membered aromatic heterocyclic group {wherein the atom in the 6-membered aromatic heterocyclic group that is bonded to the sulfonyl group is a carbon atom. In addition, the 6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D2.}.

[0464] [Method 324] Seeds or vegetative propagation organs containing an effective amount of the present compound N or its N oxide or a salt thereof.

[0465] As an embodiment of the compound N of the present invention, the following compounds can be mentioned.

[0466] [Form C1] In the compound N of the present invention, R 3a can be selected from group A a A compound which is a C1-C6 chain hydrocarbon group substituted with one or more substituents, or a C3-C8 alicyclic hydrocarbon group which may be substituted with one or more halogen atoms.

[0467] [Form C2] In the compound N of the present invention, R 3a A compound containing halogen atoms.

[0468] [Form C3] In the compound N of the present invention, R 3a Nitro, NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0469] [Form C4] In the compound N of the present invention, R 3a can be selected from group A aC1-C6 chain hydrocarbon group substituted with one or more substituents, C3-C8 alicyclic hydrocarbon group substituted with one or more halogen atoms, halogen atoms, nitro group, NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0470] [Form C5] In the compound N of the present invention, adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a The compound is substituted with one or more substituents in .

[0471] [Form C6] In the compound N of the present invention, adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they form a C5-C6 alicyclic hydrocarbon or a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0472] Group B2 a : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, and a halogen atom.

[0473] [Form C7] In the compound N of the present invention, adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they form a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0474] [Form C8] In the compound N of the present invention, two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B asubstituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a The compound is substituted with one or more substituents in .

[0475] [Form C9] In the compound N of the present invention, two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they form a C5-C6 alicyclic hydrocarbon or a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0476] [Form C10] In the compound N of the present invention, two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they form a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0477] [Form C11] In the compound N of the present invention, two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle, a benzene ring or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle, the benzene ring and the 5-6-membered aromatic heterocycle can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0478] [Form C12] In the compound N of the present invention, R 3a can be selected from group A a C1-C6 chain hydrocarbon group, C1-C3 alkoxy group, C3-C8 alicyclic hydrocarbon group {the C1-C3 alkoxy group and the C3-C8 alicyclic hydrocarbon group may be substituted with one or more halogen atoms}, halogen atoms, nitro, NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a The compounds are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom.

[0479] [Form C13] In the compound N of the present invention, R 3ais a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms}, a cyclopropyl group, a halogen atom, a nitro group, a NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a The compounds are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom.

[0480] [Form C14] In the compound N of the present invention, R 3a can be selected from group A a C1-C6 chain hydrocarbon group, C1-C3 alkoxy group, C3-C8 alicyclic hydrocarbon group {the C1-C3 alkoxy group and the C3-C8 alicyclic hydrocarbon group may be substituted with one or more halogen atoms}, halogen atoms, nitro, NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a are the same or different from each other and are hydrogen atoms, cyclopropyl groups or C1-C3 alkyl groups, or two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle, a benzene ring or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle, the benzene ring and the 5-6-membered aromatic heterocycle can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0481] [Form C15] In the compound N of the present invention, R 3a is a C1-C3 chain hydrocarbon group, a C1-C3 alkoxy group {the C1-C3 chain hydrocarbon group and the C1-C3 alkoxy group may be substituted by one or more halogen atoms}, a cyclopropyl group, a halogen atom, a nitro group, a NR 8a R 9a or C(O)NR 4a R 5a , R 4a , R 5a , R 8a and R 9a are the same or different from each other and are C1-C3 alkyl, cyclopropyl or hydrogen atom, or two adjacent R 3a and R 3aTogether with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle or a 5-6-membered aromatic heterocycle {the C5-C6 alicyclic hydrocarbon, the 5-6-membered non-aromatic heterocycle and the 5-6-membered aromatic heterocycle can be selected from Group B2 a The compound is substituted with one or more substituents in .

[0482] [Form C16] The compound N of the present invention, wherein q is 1.

[0483] [Form C17] The compound N of the present invention, wherein q is 2.

[0484] [Form C18] The compound N of the present invention, wherein q is 3.

[0485] [Form C19] In the compound N of the present invention, q is 1 or 2.

[0486] [Form C20] The compound in Form C1, wherein q is 1.

[0487] [Form C21] The compound in Form C1, wherein q is 2.

[0488] [Form C22] The compound in Form C1, wherein q is 3.

[0489] [Form C23] The compound in Form C1, wherein q is 1 or 2.

[0490] [Form C24] The compound in Form C2, wherein q is 1.

[0491] [Form C25] The compound in Form C2, wherein q is 2.

[0492] [Form C26] The compound in Form C2, wherein q is 3.

[0493] [Form C27] The compound in Form C2, wherein q is 1 or 2.

[0494] [Form C28] The compound in Form C3, wherein q is 1.

[0495] [Form C29] The compound in Form C3, wherein q is 2.

[0496] [Form C30] The compound in Form C3, wherein q is 3.

[0497] [Form C31] The compound in Form C3, wherein q is 1 or 2.

[0498] [Form C32] The compound in Form C4, wherein q is 1.

[0499] [Form C33] The compound in Form C4, wherein q is 2.

[0500] [Form C34] The compound in Form C4, wherein q is 3.

[0501] [Form C35] The compound in Form C4, wherein q is 1 or 2.

[0502] [Form C36] The compound in Form C5, wherein q is 1.

[0503] [Form C37] The compound in Form C5, wherein q is 2.

[0504] [Form C38] The compound in Form C5, wherein q is 3.

[0505] [Form C39] The compound in Form C5, wherein q is 1 or 2.

[0506] [Form C40] The compound in Form C6, wherein q is 1.

[0507] [Form C41] The compound in Form C6, wherein q is 2.

[0508] [Form C42] The compound in Form C6, wherein q is 3.

[0509] [Form C43] The compound in Form C6, wherein q is 1 or 2.

[0510] [Form C44] The compound in Form C7, wherein q is 1.

[0511] [Form C45] The compound in Form C7, wherein q is 2.

[0512] [Form C46] The compound in Form C7, wherein q is 3.

[0513] [Form C47] The compound in Form C7, wherein q is 1 or 2.

[0514] [Form C48] The compound in Form C8, wherein q is 2.

[0515] [Form C49] The compound in Form C8, wherein q is 3.

[0516] [Form C50] The compound in Form C8, wherein q is 2 or 3.

[0517] [Form C51] The compound in Form C9, wherein q is 2.

[0518] [Form C52] The compound in Form C9, wherein q is 3.

[0519] [Form C53] The compound in Form C9, wherein q is 2 or 3. [Form C54] The compound in Form C10, wherein q is 2.

[0520] [Form C55] The compound in Form C10, wherein q is 3.

[0521] [Form C56] The compound in Form C10, wherein q is 2 or 3.

[0522] [Form C57] The compound in Form C11, wherein q is 2.

[0523] [Form C58] The compound in Form C11, wherein q is 3.

[0524] [Form C59] The compound in Form C11, wherein q is 2 or 3.

[0525] [Form C60] The compound in Form C12, wherein q is 1.

[0526] [Form C61] The compound in Form C12, wherein q is 2.

[0527] [Form C62] The compound in Form C12, wherein q is 3.

[0528] [Form C63] The compound in Form C12, wherein q is 1 or 2.

[0529] [Form C64] The compound in Form C13, wherein q is 1.

[0530] [Form C65] The compound in Form C13, wherein q is 2.

[0531] [Form C66] The compound in Form C13, wherein q is 3.

[0532] [Form C67] The compound in Form C13, wherein q is 1 or 2.

[0533] [Form C68] The compound in Form C14, wherein q is 1.

[0534] [Form C69] The compound in Form C14, wherein q is 2.

[0535] [Form C70] The compound in Form C14, wherein q is 3.

[0536] [Form C71] The compound in Form C14, wherein q is 1 or 2.

[0537] [Form C72] The compound in Form C15, wherein q is 1.

[0538] [Form C73] The compound in Form C15, wherein q is 2.

[0539] [Form C74] The compound in Form C15, wherein q is 3.

[0540] [Form C75] The compound in Form C15, wherein q is 1 or 2.

[0541] [Embodiment C76] In the compound N of the present invention, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0542] [Method C77] In method C1, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0543] [Method C78] In method C2, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0544] [Method C79] In method C3, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0545] [Mode C80] In Mode C4, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0546] [Method C81] In method C5, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0547] [Method C82] In method C6, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0548] [Method C83] In method C7, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0549] [Mode C84] In Mode C8, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0550] [Method C85] In method C9, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0551] [Method C86] In method C10, R 1a and R2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0552] [Method C87] In method C11, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0553] [Method C88] In method C12, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0554] [Method C89] In method C13, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0555] [Method C90] In method C14, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0556] [Method C91] In method C15, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0557] [Method C92] In method C16, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0558] [Method C93] In method C17, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0559] [Method C94] In method C18, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0560] [Method C95] In method C19, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0561] [Method C96] In method C20, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0562] [Method C97] In method C21, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0563] [Method C98] In method C22, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0564] [Method C99] In method C23, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0565] [Method C100] In method C24, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0566] [Method C101] In method C25, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0567] [Method C102] In method C26, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0568] [Method C103] In method C27, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0569] [Method C104] In method C28, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0570] [Method C105] In method C29, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0571] [Method C106] In method C30, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0572] [Method C107] In method C31, R 1a and R2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0573] [Method C108] In method C32, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0574] [Method C109] In method C33, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0575] [Method C110] In method C34, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0576] [Method C111] In method C35, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0577] [Method C112] In method C36, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0578] [Method C113] In method C37, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0579] [Method C114] In method C38, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0580] [Method C115] In method C39, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0581] [Method C116] In method C40, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0582] [Method C117] In method C41, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0583] [Method C118] In method C42, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0584] [Method C119] In method C43, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0585] [Method C120] In method C44, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0586] [Method C121] In method C45, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0587] [Method C122] In method C46, ​​R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0588] [Method C123] In method C47, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0589] [Method C124] In method C48, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0590] [Method C125] In method C49, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0591] [Method C126] In method C50, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0592] [Method C127] In method C51, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0593] [Method C128] In method C52, R1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0594] [Method C129] In method C53, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0595] [Method C130] In method C54, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0596] [Method C131] In method C55, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0597] [Method C132] In method C56, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0598] [Method C133] In method C57, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0599] [Method C134] In method C58, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0600] [Method C135] In method C59, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0601] [Method C136] In method C60, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0602] [Method C137] In method C61, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0603] [Method C138] In method C62, R 1a and R 2aThe compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0604] [Method C139] In method C63, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0605] [Method C140] In method C64, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0606] [Method C141] In method C65, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0607] [Method C142] In method C66, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0608] [Method C143] In method C67, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0609] [Method C144] In method C68, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0610] [Method C145] In method C69, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0611] [Method C146] In method C70, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0612] [Method C147] In method C71, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0613] [Method C148] In method C72, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0614] [Method C149] In method C73, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0615] [Method C150] In method C74, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0616] [Method C151] In method C75, R 1a and R 2a The compounds are the same or different from each other and are C1-C3 alkyl or hydrogen atom.

[0617] [Form C152] In the compound N of the present invention, R 1a and R 2a A compound containing hydrogen atoms.

[0618] [Method C153] In method C1, R 1a and R 2a A compound containing hydrogen atoms.

[0619] [Method C154] In method C2, R 1a and R 2a A compound containing hydrogen atoms.

[0620] [Method C155] In method C3, R 1a and R 2a A compound containing hydrogen atoms.

[0621] [Method C156] In method C4, R 1a and R 2a A compound containing hydrogen atoms.

[0622] [Method C157] In method C5, R 1a and R 2a A compound containing hydrogen atoms.

[0623] [Method C158] In method C6, R 1a and R 2a A compound containing hydrogen atoms.

[0624] [Method C159] In method C7, R 1a and R 2a A compound containing hydrogen atoms.

[0625] [Method C160] In method C8, R 1a and R 2a A compound containing hydrogen atoms.

[0626] [Method C161] In method C9, R 1a and R 2a A compound containing hydrogen atoms.

[0627] [Method C162] In method C10, R 1a and R 2a A compound containing hydrogen atoms.

[0628] [Method C163] In method C11, R 1a and R 2a A compound containing hydrogen atoms.

[0629] [Method C164] In method C12, R 1a and R 2a A compound containing hydrogen atoms.

[0630] [Method C165] In method C13, R 1a and R 2a A compound containing hydrogen atoms.

[0631] [Method C166] In method C14, R 1a and R 2a A compound containing hydrogen atoms.

[0632] [Method C167] In method C15, R 1a and R 2a A compound containing hydrogen atoms.

[0633] [Method C168] In method C16, R 1a and R 2a A compound containing hydrogen atoms.

[0634] [Method C169] In method C17, R 1a and R 2a A compound containing hydrogen atoms.

[0635] [Method C170] In method C18, R 1a and R 2a A compound containing hydrogen atoms.

[0636] [Method C171] In method C19, R 1a and R 2a A compound containing hydrogen atoms.

[0637] [Method C172] In method C20, R 1a and R 2a A compound containing hydrogen atoms.

[0638] [Method C173] In method C21, R 1a and R 2aA compound containing hydrogen atoms.

[0639] [Method C174] In method C22, R 1a and R 2a A compound containing hydrogen atoms.

[0640] [Method C175] In method C23, R 1a and R 2a A compound containing hydrogen atoms.

[0641] [Method C176] In method C24, R 1a and R 2a A compound containing hydrogen atoms.

[0642] [Method C177] In method C25, R 1a and R 2a A compound containing hydrogen atoms.

[0643] [Method C178] In method C26, R 1a and R 2a A compound containing hydrogen atoms.

[0644] [Method C179] In method C27, R 1a and R 2a A compound containing hydrogen atoms.

[0645] [Method C180] In method C28, R 1a and R 2a A compound containing hydrogen atoms.

[0646] [Method C181] In method C29, R 1a and R 2a A compound containing hydrogen atoms.

[0647] [Method C182] In method C30, R 1a and R 2a A compound containing hydrogen atoms.

[0648] [Method C183] In method C31, R 1a and R 2a A compound containing hydrogen atoms.

[0649] [Method C184] In method C32, R 1a and R 2a A compound containing hydrogen atoms.

[0650] [Method C185] In method C33, R 1a and R 2a A compound containing hydrogen atoms.

[0651] [Method C186] In method C34, R1a and R 2a A compound containing hydrogen atoms.

[0652] [Method C187] In method C35, R 1a and R 2a A compound containing hydrogen atoms.

[0653] [Method C188] In method C36, R 1a and R 2a A compound containing hydrogen atoms.

[0654] [Method C189] In method C37, R 1a and R 2a A compound containing hydrogen atoms.

[0655] [Method C190] In method C38, R 1a and R 2a A compound containing hydrogen atoms.

[0656] [Method C191] In method C39, R 1a and R 2a A compound containing hydrogen atoms.

[0657] [Method C192] In method C40, R 1a and R 2a A compound containing hydrogen atoms.

[0658] [Method C193] In method C41, R 1a and R 2a A compound containing hydrogen atoms.

[0659] [Method C194] In method C42, R 1a and R 2a A compound containing hydrogen atoms.

[0660] [Method C195] In method C43, R 1a and R 2a A compound containing hydrogen atoms.

[0661] [Method C196] In method C44, R 1a and R 2a A compound containing hydrogen atoms.

[0662] [Method C197] In method C45, R 1a and R 2a A compound containing hydrogen atoms.

[0663] [Method C198] In method C46, ​​R 1a and R 2a A compound containing hydrogen atoms.

[0664] [Method C199] In method C47, R 1a and R 2a A compound containing hydrogen atoms.

[0665] [Mode C200] In Mode C48, R 1a and R 2a A compound containing hydrogen atoms.

[0666] [Method C201] In method C49, R 1a and R 2a A compound containing hydrogen atoms.

[0667] [Method C202] In method C50, R 1a and R 2a A compound containing hydrogen atoms.

[0668] [Method C203] In method C51, R 1a and R 2a A compound containing hydrogen atoms.

[0669] [Method C204] In method C52, R 1a and R 2a A compound containing hydrogen atoms.

[0670] [Method C205] In method C53, R 1a and R 2a A compound containing hydrogen atoms.

[0671] [Method C206] In method C54, R 1a and R 2a A compound containing hydrogen atoms.

[0672] [Method C207] In method C55, R 1a and R 2a A compound containing hydrogen atoms.

[0673] [Method C208] In method C56, R 1a and R 2a A compound containing hydrogen atoms.

[0674] [Method C209] In method C57, R 1a and R 2a A compound containing hydrogen atoms.

[0675] [Method C210] In method C58, R 1a and R 2a A compound containing hydrogen atoms.

[0676] [Method C211] In method C59, R 1a and R 2aA compound containing hydrogen atoms.

[0677] [Method C212] In method C60, R 1a and R 2a A compound containing hydrogen atoms.

[0678] [Method C213] In method C61, R 1a and R 2a A compound containing hydrogen atoms.

[0679] [Method C214] In method C62, R 1a and R 2a A compound containing hydrogen atoms.

[0680] [Method C215] In method C63, R 1a and R 2a A compound containing hydrogen atoms.

[0681] [Method C216] In method C64, R 1a and R 2a A compound containing hydrogen atoms.

[0682] [Method C217] In method C65, R 1a and R 2a A compound containing hydrogen atoms.

[0683] [Method C218] In method C66, R 1a and R 2a A compound containing hydrogen atoms.

[0684] [Method C219] In method C67, R 1a and R 2a A compound containing hydrogen atoms.

[0685] [Method C220] In method C68, R 1a and R 2a A compound containing hydrogen atoms.

[0686] [Method C221] In method C69, R 1a and R 2a A compound containing hydrogen atoms.

[0687] [Method C222] In method C70, R 1a and R 2a A compound containing hydrogen atoms.

[0688] [Method C223] In method C71, R 1a and R 2a A compound containing hydrogen atoms.

[0689] [Method C224] In method C72, R1a and R 2a A compound containing hydrogen atoms.

[0690] [Method C225] In method C73, R 1a and R 2a A compound containing hydrogen atoms.

[0691] [Method C226] In method C74, R 1a and R 2a A compound containing hydrogen atoms.

[0692] [Method C227] In method C75, R 1a and R 2a A compound containing hydrogen atoms.

[0693] [Form C228] In the compound N of the present invention, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0694] [Method C229] In method C1, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0695] [Method C230] In method C2, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0696] [Method C231] In method C3, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0697] [Method C232] In method C4, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0698] [Method C233] In method C5, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0699] [Method C234] In method C6, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0700] [Method C235] In method C7, R 1a and R 2aA compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0701] [Method C236] In method C8, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0702] [Method C237] In method C9, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0703] [Method C238] In method C10, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0704] [Method C239] In method C11, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0705] [Method C240] In method C12, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0706] [Method C241] In method C13, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0707] [Method C242] In method C14, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0708] [Method C243] In method C15, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0709] [Method C244] In method C16, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0710] [Method C245] In method C17, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0711] [Method C246] In method C18, R1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0712] [Method C247] In method C19, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0713] [Method C248] In method C20, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0714] [Method C249] In method C21, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0715] [Method C250] In method C22, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0716] [Method C251] In method C23, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0717] [Method C252] In method C24, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0718] [Method C253] In method C25, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0719] [Method C254] In method C26, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0720] [Mode C255] In Mode C27, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0721] [Method C256] In method C28, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0722] [Method C257] In method C29, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0723] [Method C258] In method C30, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0724] [Method C259] In method C31, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0725] [Method C260] In method C32, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0726] [Method C261] In method C33, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0727] [Method C262] In method C34, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0728] [Method C263] In method C35, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0729] [Method C264] In method C36, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0730] [Method C265] In method C37, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0731] [Method C266] In method C38, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0732] [Method C267] In method C39, R 1a and R 2aA compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0733] [Method C268] In method C40, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0734] [Method C269] In method C41, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0735] [Method C270] In method C42, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0736] [Method C271] In method C43, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0737] [Method C272] In method C44, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0738] [Method C273] In method C45, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0739] [Method C274] In method C46, ​​R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0740] [Method C275] In method C47, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0741] [Method C276] In method C48, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0742] [Method C277] In method C49, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0743] [Method C278] In method C50, R1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0744] [Method C279] In method C51, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0745] [Method C280] In method C52, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0746] [Method C281] In method C53, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0747] [Method C282] In method C54, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0748] [Method C283] In method C55, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0749] [Method C284] In method C56, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0750] [Method C285] In method C57, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0751] [Method C286] In method C58, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0752] [Method C287] In method C59, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0753] [Method C288] In method C60, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0754] [Method C289] In method C61, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0755] [Method C290] In method C62, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0756] [Method C291] In method C63, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0757] [Method C292] In method C64, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0758] [Method C293] In method C65, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0759] [Method C294] In method C66, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0760] [Method C295] In method C67, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0761] [Method C296] In method C68, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0762] [Method C297] In method C69, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0763] [Method C298] In method C70, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0764] [Method C299] In method C71, R 1a and R 2aA compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0765] [Mode C300] In Mode C72, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0766] [Method C301] In method C73, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0767] [Method C302] In method C74, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0768] [Method C303] In method C75, R 1a and R 2a A compound which is the same or different from each other and is a hydrogen atom or a halogen atom.

[0769] [Embodiment C304] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0770] [Embodiment C305] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D a A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0771] [Embodiment C306] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D a A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0772] [Embodiment C307] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0773] Group D2 a : A group consisting of a C1-C3 alkyl group, a halogen atom and a cyano group.

[0774] [Embodiment C308] In the compound N of the present invention or any one of Embodiments C1 to C303, Za can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0775] [Embodiment C309] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0776] [Embodiment C310] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a is a 5-6 membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 5-6 membered aromatic heterocyclic group is a carbon atom. In addition, the 5-6 membered aromatic heterocyclic group may be selected from group D a The compound is substituted with one or more substituents in .

[0777] [Embodiment C311] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl) substituted with one or more substituents.

[0778] [Embodiment C312] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl) substituted with one or more substituents in the formula (hereinafter referred to as "the compound").

[0779] [Embodiment C313] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 2-thienyl) substituted with one or more substituents.

[0780] [Embodiment C314] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 2-thienyl) substituted with one or more substituents.

[0781] [Embodiment C315] In any one of the compound N of the present invention or Embodiments C1 to C303, Z a can be selected from group D2 aA compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl and 2-thienyl) substituted with one or more substituents in the compound.

[0782] [Embodiment C316] In any one of the compound N of the present invention or Embodiments C1 to C303, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl and 2-thienyl) substituted with one or more substituents in the formula (hereinafter referred to as "the present invention").

[0783] [Embodiment C317] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a is furanyl, thienyl, imidazolyl, pyrazolyl or pyridinyl {the furanyl, thienyl, imidazolyl, pyrazolyl and pyridinyl can be selected from Group D3 a The compound is substituted with one or more substituents in .

[0784] Group D3 a : A group consisting of a C1-C3 alkyl group and a halogen atom.

[0785] [Embodiment C318] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a is furanyl, imidazolyl or pyridyl {the furanyl, the imidazolyl and the pyridyl can be selected from Group D3 a The compound is substituted with one or more substituents in .

[0786] [Embodiment C319] In any one of the compound N of the present invention or Embodiments C1 to C303, Z a is a 5-membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 5-membered aromatic heterocyclic group is a carbon atom. In addition, the 5-membered aromatic heterocyclic group may be selected from the group D a The compound is substituted with one or more substituents in .

[0787] [Embodiment C320] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a is a 6-membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 6-membered aromatic heterocyclic group is a carbon atom. In addition, the 6-membered aromatic heterocyclic group may be selected from the group D a The compound is substituted with one or more substituents in .

[0788] [Embodiment C321] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group F a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0789] [Embodiment C322] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group F a A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0790] [Embodiment C323] In the compound N of the present invention or any one of Embodiments C1 to C303, Z a can be selected from group F a A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0791] [Embodiment C324] In the compound N of the present invention, R 3a is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8a R 9a , OR 10a or SR 11a ,

[0792] Two adjacent R 3a and R 3a Compounds which can form, together with the carbon atoms to which they are bonded, a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle or a 5-7 membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7 membered non-aromatic heterocycle and the 5-7 membered aromatic heterocycle may be substituted with one or more halogen atoms}.

[0793] [Embodiment C325] In the compound N of the present invention, R 3a is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8a R 9a , OR 10a or SR 11a of compounds.

[0794] [Embodiment C326] In the compound N of the present invention, two adjacent R 3a and R 3a A compound which, together with the carbon atoms to which they are bonded, forms a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle or a 5-7 membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7 membered non-aromatic heterocycle and the 5-7 membered aromatic heterocycle may be substituted with one or more halogen atoms}.

[0795] [Form C327] The compound in Form C324, wherein q is 1.

[0796] [Form C328] The compound in Form C324, wherein q is 2.

[0797] [Form C329] The compound in Form C324, wherein q is 3.

[0798] [Form C330] The compound in Form C324, wherein q is 1 or 2.

[0799] [Form C331] The compound wherein q is 1 in Form C325.

[0800] [Form C332] The compound wherein q is 2 in Form C325.

[0801] [Form C333] The compound in Form C325, wherein q is 3.

[0802] [Form C334] The compound in Form C325, wherein q is 1 or 2.

[0803] [Form C335] The compound wherein q is 2 in Form C326.

[0804] [Form C336] The compound in Form C326, wherein q is 3.

[0805] [Method C337] In method C324, R 1a and R 2a A compound containing hydrogen atoms.

[0806] [Method C338] In method C325, R 1a and R 2a A compound containing hydrogen atoms.

[0807] [Method C339] In method C326, R 1a and R 2a A compound containing hydrogen atoms.

[0808] [Method C340] In method C327, R 1a and R 2a A compound containing hydrogen atoms.

[0809] [Method C341] In method C328, R 1a and R 2a A compound containing hydrogen atoms.

[0810] [Method C342] In method C329, R 1a and R 2a A compound containing hydrogen atoms.

[0811] [Method C343] In method C330, R 1a and R 2a A compound containing hydrogen atoms.

[0812] [Method C344] In method C331, R 1a and R 2a A compound containing hydrogen atoms.

[0813] [Method C345] In method C332, R 1a and R 2a A compound containing hydrogen atoms.

[0814] [Method C346] In method C333, R 1a and R 2a A compound containing hydrogen atoms.

[0815] [Method C347] In method C334, R 1a and R 2a A compound containing hydrogen atoms.

[0816] [Method C348] In method C335, R 1a and R 2a A compound containing hydrogen atoms.

[0817] [Method C349] In method C336, R 1a and R 2a A compound containing hydrogen atoms.

[0818] [Method C350] In any one of methods C324 to C349, Z a can be selected from group D a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0819] [Method C351] In any one of methods C324 to C349, Z a can be selected from group D a A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0820] [Method C352] In any one of methods C324 to C349, Z a can be selected from group D a A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0821] [Method C353] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0822] [Method C354] In any one of methods C324 to C349, Z a can be selected from group D2 aA compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0823] [Method C355] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0824] [Method C356] In any one of methods C324 to C349, Z a is a 5-6 membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 5-6 membered aromatic heterocyclic group is a carbon atom. In addition, the 5-6 membered aromatic heterocyclic group may be selected from group D a The compound is substituted with one or more substituents in .

[0825] [Method C357] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl) substituted with one or more substituents.

[0826] [Method C358] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl) substituted with one or more substituents in the formula (hereinafter referred to as "the compound").

[0827] [Method C359] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 2-thienyl) substituted with one or more substituents.

[0828] [Method C360] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 2-thienyl) substituted with one or more substituents.

[0829] [Method C361] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5- to 6-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl and 2-thienyl) substituted with one or more substituents in the compound.

[0830] [Method C362] In any one of methods C324 to C349, Z a can be selected from group D2 a A compound comprising a 5-membered aromatic heterocyclic group (excluding 1,3-dimethyl-1H-pyrazol-4-yl and 2-thienyl) substituted with one or more substituents in the formula (hereinafter referred to as "the present invention").

[0831] [Method C363] In any of methods C324 to C349, Z a is furanyl, thienyl, imidazolyl, pyrazolyl or pyridinyl {the furanyl, thienyl, imidazolyl, pyrazolyl and pyridinyl can be selected from Group D3 a The compound is substituted with one or more substituents in .

[0832] [Method C364] In any of methods C324 to C349, Z a is furanyl, imidazolyl or pyridyl {the furanyl, the imidazolyl and the pyridyl can be selected from Group D3 a The compound is substituted with one or more substituents in .

[0833] [Method C365] In any of methods C324 to C349, Z a is a 5-membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 5-membered aromatic heterocyclic group is a carbon atom. In addition, the 5-membered aromatic heterocyclic group may be selected from the group D a The compound is substituted with one or more substituents in .

[0834] [Method C366] In any one of methods C324 to C349, Z a is a 6-membered aromatic heterocyclic group {wherein the atom bonded to the sulfonyl group in the 6-membered aromatic heterocyclic group is a carbon atom. In addition, the 6-membered aromatic heterocyclic group may be selected from the group D a The compound is substituted with one or more substituents in .

[0835] [Method C367] In any of methods C324 to C349, Z a can be selected from group F a A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0836] [Method C368] In any one of methods C324 to C349, Z a can be selected from group F a A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0837] [Method C369] In any one of methods C324 to C349, Z a can be selected from group Fa A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0838] [Embodiment A1] A method for controlling soybean rust fungus, which is carried out by treating soybeans or soil for cultivating soybeans with the present compound.

[0839] [Form AC1] A method for controlling soybean rust fungus, which is carried out by treating soybeans or soil for cultivating soybeans with the compound of the present invention.

[0840] As an embodiment of the intermediate A, the following compounds can be mentioned.

[0841] [Form B1] In the intermediate A, X b A compound containing a chlorine atom, a bromine atom or an iodine atom.

[0842] [Form B2] In the intermediate A, X b A compound containing iodine atoms.

[0843] [Form B3] In the intermediate A, X b B(OH) 2 Or a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl compound.

[0844] [Form B4] In any one of Intermediate A or Forms B1 to B3, Z b can be selected from group F b A compound having a 5- to 10-membered aromatic heterocyclic group substituted with one or more substituents.

[0845] Group F b : A group consisting of a C1-C6 chain hydrocarbon group and a halogen atom.

[0846] [Form B5] In any one of Intermediate A or Forms B1 to B3, Z b can be selected from group F b A compound having a 5-6 membered aromatic heterocyclic group substituted with one or more substituents.

[0847] [Form B6] In any one of Intermediate A or Forms B1 to B3, Z b can be selected from group F b A compound comprising a 5-membered aromatic heterocyclic group substituted with one or more substituents.

[0848] [Form B7] In any one of Intermediate A or Forms B1 to B3, Z b can be selected from group F b A compound having a 6-membered aromatic heterocyclic group substituted with one or more substituents.

[0849] [Form B8] In any one of Intermediate A or Forms B1 to B3, Z b A compound having a 5-membered aromatic heterocyclic group.

[0850] [Form B9] In any one of Intermediate A or Forms B1 to B3, Z b A compound having a 6-membered aromatic heterocyclic group.

[0851] Next, the method for producing the present compound (including the compound of the present invention) is described.

[0852] Manufacturing Method A

[0853] The compound represented by formula (I) (ie, the present compound N) can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with a compound represented by formula (A2) (hereinafter referred to as compound (A2)) in the presence of a base.

[0854] [Chemical formula 8]

[0855]

[0856] 〔In the formula, X 1 Represents a chlorine atom, a bromine atom, or OS(O) 2 Z, other symbols have the same meanings as above. ]

[0857] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter referred to as hydrocarbons); ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and dimethoxyethane (hereinafter referred to as ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); water, and a mixture of two or more thereof.

[0858] Examples of the base used in the reaction include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate (hereinafter referred to as alkali metal hydrogen carbonates); alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and cesium hydroxide (hereinafter referred to as alkali metal hydroxides); alkali metal hydrides such as lithium hydride and sodium hydride (hereinafter referred to as alkali metal hydrides); alkali metal alkoxides such as sodium tert-butoxide and potassium tert-butoxide (hereinafter referred to as alkali metal alkoxides), and the like.

[0859] In the reaction, the compound (A2) is usually used in a ratio of 1 to 10 mol, and the base is usually used in a ratio of 1 to 10 mol, based on 1 mol of the compound (A1).

[0860] The reaction temperature is usually in the range of -20 to 150° C. The reaction time is usually in the range of 0.1 to 120 hours.

[0861] After the reaction is completed, the reaction mixture is mixed with water, and then extracted with an organic solvent. The organic layer is subjected to post-treatment operations such as drying and concentration, whereby the present compound N can be isolated.

[0862] The compound (A2) is a commercially available compound or can be produced by a known method.

[0863] Manufacturing method B

[0864] The present compound N can also be produced by reacting a compound represented by formula (B1) (hereinafter referred to as compound (B1)) with a compound represented by formula (B2) (hereinafter referred to as compound (B2)) in the presence of a palladium catalyst and a base.

[0865] [Chemical formula 9]

[0866]

[0867] 〔In the formula, X 2 represents a chlorine atom, a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group, M 1 Indicates B(OH) 2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl, and other symbols have the same meanings as above. ]

[0868] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; sulfoxides (hereinafter referred to as sulfoxides) such as dimethyl sulfoxide (hereinafter referred to as DMSO); ketones (hereinafter referred to as ketones) such as acetone and methyl isobutyl ketone; nitriles; alcohols (hereinafter referred to as alcohols) such as methanol and ethanol; water, and mixtures of two or more thereof.

[0869] Examples of the palladium catalyst used in the reaction include palladium (II) acetate, bis(triphenylphosphine)palladium (II) dichloride, tetrakis(triphenylphosphine)palladium (0), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride, and tris(dibenzylideneacetone)dipalladium.

[0870] Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrogen carbonates; alkali metal hydroxides; alkali metal fluorides such as sodium fluoride, potassium fluoride, and cesium fluoride (hereinafter referred to as alkali metal fluorides); alkali metal hydrides; alkali metal alkoxides and tripotassium phosphate.

[0871] In the reaction, the compound (B2) is usually used in a ratio of 1 to 10 mol, the base is usually used in a ratio of 1 to 10 mol, and the palladium catalyst is usually used in a ratio of 0.0001 to 1 mol, based on 1 mol of the compound (B1).

[0872] The reaction temperature is usually in the range of 0 to 150° C. The reaction time is usually in the range of 0.1 to 24 hours.

[0873] After the reaction is completed, the reaction mixture is mixed with water, and then extracted with an organic solvent. The organic layer is subjected to post-treatment operations such as drying and concentration, whereby the present compound can be isolated.

[0874] Compound (B2) is a commercially available compound, or can be produced according to the method described in, for example, Chem. Rev., 1995, 95, 2457.

[0875] Manufacturing method C

[0876] The present compound N can also be produced by reacting a compound represented by formula (C1) (hereinafter referred to as compound (C1)) with a compound represented by formula (C2) (hereinafter referred to as compound (C2)) in the presence of a palladium catalyst and a base.

[0877] [Chemical formula 10]

[0878]

[0879] [In the formula, the symbols have the same meanings as above.]

[0880] The reaction can be carried out according to Production Method B using Compound (C2) instead of Compound (B1) or using Compound (C1) instead of Compound (B2).

[0881] Compound (C2) is a commercially available compound, or can be produced according to the method described in, for example, Tetrahedron Letters, 2003, 8781.

[0882] Next, the method for producing the intermediate of the present compound (including the compound of the present invention) is described.

[0883] Reference Manufacturing Method A

[0884] The compound (A1) can be produced by reacting a compound represented by the formula (MA1) (hereinafter referred to as the compound (MA1)) with hydrazine.

[0885] [Chemical formula 11]

[0886]

[0887] 〔In the formula, R 21 represents hydroxyl, dimethylamino or diethylamino, and other symbols have the same meanings as above.

[0888] The reaction can be carried out according to the method described in, for example, Bioorganic and Medicinal Chemistry, 2014, 22, 4189 or J. Med. Chem., 2003, 46, 5416.

[0889] Reference Manufacturing Method B

[0890] The compound represented by formula (MA2) (hereinafter referred to as compound (MA2)) can be produced by reacting a compound represented by formula (MB1) (hereinafter referred to as compound (MB1)) with a compound represented by formula (MB2) (hereinafter referred to as compound (MB2)).

[0891] [Chemical formula 12]

[0892]

[0893] 〔In the formula, R 22 The same or different from each other, representing methyl or ethyl, R 23 The same or different from each other, represents C1-C6 alkyl or benzyl, and other symbols have the same meanings as above.

[0894] The reaction can be carried out according to the method described in, for example, European Journal of Medicinal Chemistry, 2011, 46, 5817.

[0895] Compound (MB2) is a commercially available compound or can be produced by a known method.

[0896] Reference Manufacturing Method C

[0897] The compound represented by formula (MA3) (hereinafter referred to as compound (MA3)) can be produced by reacting compound (MB1) with a compound represented by formula (MC1) (hereinafter referred to as compound (MC1)) in the presence of a base.

[0898] [Chemical formula 13]

[0899]

[0900] [In the formula, the symbols have the same meanings as above.]

[0901] The reaction can be carried out according to the method described in, for example, J.Am.Chem.Soc., 2017, 139, 2421.

[0902] Compound (MC1) is a commercially available compound or can be produced by a known method.

[0903] Reference Manufacturing Method D

[0904] Compound (MB1) can be produced by reacting a compound represented by formula (MD1) (hereinafter referred to as compound (MD1)) with a compound represented by formula (MD2) (hereinafter referred to as compound (MD2)).

[0905] [Chemical formula 14]

[0906]

[0907] 〔In the formula, R 24 represents a cyano group, a chlorocarbonyl group, a di(C1-C4 alkyl)carbamoyl group, an N-methoxy-N-methylcarbamoyl group, a morpholinocarbonyl group, a pyrrol-1-ylcarbonyl group, a pyrazol-1-ylcarbonyl group, an imidazol-1-ylcarbonyl group or a benzotriazol-1-ylcarbonyl group, and X 3 represents a chlorine atom, a bromine atom or an iodine atom, and other symbols have the same meanings as above.

[0908] The reaction can be carried out according to the method described in, for example, Synthesis, 2008, 28, 3707.

[0909] Compound (MD1) is a commercially available compound or can be produced according to the method described in Synthesis, 2008, 28, 3707. Compound (MD2) is a commercially available compound or can be produced by a known method.

[0910] Reference Manufacturing Method E

[0911] The compound represented by formula (MB3) (hereinafter referred to as compound (MB3)) can be produced according to the following synthesis route.

[0912] [Chemical formula 15]

[0913]

[0914] 〔In the formula, X 3 represents a bromine atom or an iodine atom, M 2 Indicates Li or MgX 3, R 1D and R 2D are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a hydrogen atom, a nitro group, a cyano group, a NR 8 R 9 , OR 10 、S(O) k R 11 or C(O)NR 4 R 5 , R 3D represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a nitro group, a cyano group, a NR 8 R 9 , OR 10 、S(O) k R 11 or C(O)NR 4 R 5 , R 25 represents a cyano group, a chlorocarbonyl group, a di(C1-C4 alkyl)carbamoyl group, an N-methoxy-N-methylcarbamoyl group, a morpholinocarbonyl group, a pyrrol-1-ylcarbonyl group, a pyrazol-1-ylcarbonyl group, an imidazol-1-ylcarbonyl group, a benzotriazol-1-ylcarbonyl group, a -C(O)OC(O)CH 3 or C2-C4 alkoxycarbonyl, and other symbols have the same meanings as above. ]

[0915] The compound represented by formula (MF2) (hereinafter referred to as compound (MF2)) can be produced by reacting the compound represented by formula (MF1) (hereinafter referred to as compound (MF1)) with a Grignard reagent such as butyllithium or isopropylmagnesium chloride.

[0916] Compound (MB3) can be produced by reacting compound (MF2) with a compound represented by formula (MF3) (hereinafter referred to as compound (MF3)).

[0917] These reactions can be carried out according to the method described in the specification of Chinese Patent Application Publication No. 105461538, for example.

[0918] Compound (MF1) is a commercially available compound, or can be produced according to the method described in, for example, J. Am. Chem. Soc., 2012, 134, 20597.

[0919] Compound (MF3) is a commercially available compound, or can be produced by a known method.

[0920] Reference Manufacturing Method F

[0921] The compound (B1) can be produced by reacting a compound represented by the formula (MG1) (hereinafter referred to as the compound (MG1)) with the compound (A2) in the presence of a base.

[0922] [Chemical formula 16]

[0923]

[0924] [In the formula, the symbols have the same meanings as above.]

[0925] The reaction can be carried out according to Production Method A using Compound (MG1) instead of Compound (A1).

[0926] Compound (MG1) is a commercially available compound, or can be produced according to the method described in, for example, Medicinal Chemistry Letters, 2007, 17, 6274.

[0927] Reference Manufacturing Method G

[0928] Compound (C1) can be produced by reacting a compound represented by formula (MG2) (hereinafter referred to as compound (MG2)) with compound (A2) in the presence of a base.

[0929] [Chemical formula 17]

[0930]

[0931] [In the formula, the symbols have the same meanings as above.]

[0932] The reaction can be carried out according to Reference Production Method F using Compound (MG2) instead of Compound (MG1).

[0933] Compound (MG2) is a commercially available compound, or can be produced according to the method described in, for example, Medicinal Chemistry Letters, 2007, 17, 6274.

[0934] The compound of the present invention may be mixed or used in combination with one or more components (hereinafter referred to as present components) selected from the group consisting of the following Group (a), Group (b), Group (c) and Group (d).

[0935] The aforementioned mixed use or combined use means that the compound of the present invention and the present component are used simultaneously, separately or with a time interval therebetween.

[0936] When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in the same preparation.

[0937] One aspect of the present invention is a composition (hereinafter referred to as composition A) comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d) (i.e., the present component) and the compound of the present invention.

[0938] Group (a) is composed of acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphorus insecticides), GABA-gated chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), pseudojuvenile hormones, multisite inhibitors, chord organ TRPV channel modulators, mite growth inhibitors, and microbial-derived insect midgut lining disruptors. The present invention relates to a group consisting of: inhibitors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ranolidine receptor modulators (e.g., diamide-based insecticides), chord organ modulators, microbial insecticides, and other insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients. These ingredients are described according to the classification of the mechanism of action based on IRAC.

[0939] Group (b) is a group consisting of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., triazole-based DMI fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-site contact active fungicides, microbial fungicides and other fungicidal active ingredients. These ingredients are described according to the classification of the mechanism of action based on FRAC.

[0940] Group (c) is a group of plant growth regulating ingredients including mycorrhizal fungi and rhizobia.

[0941] Group (d) is a group of repellent ingredients.

[0942] Examples of combinations of the present component and the compound of the present invention are described below. For example, alanycarb+SX means a combination of alanycarb and SX.

[0943] It should be noted that the abbreviation of SX refers to any one of the compounds of the present invention selected from the compound group SX1 to SX145. In addition, the components described below are all known components and can be obtained from commercially available preparations or manufactured by known methods. In the case where the component is a microorganism, it can also be obtained from a bacterial preservation institution. It should be noted that the numbers in brackets represent CAS RN (registered trademark).

[0944] Combination of the present component of the above group (a) with the compound of the present invention:

[0945] Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide ...taminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + SX, acetaminophen + phosphide + SX, amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, bark of Celastrus angulatus+SX, bendiocarb+SX, benfluthrin+SX, benfuracarb+SX, bensultap+SX, benzoximate+SX, benzpyrimoxan+SX, beta-cyfluthrin+SX, beta-cypermethrin+SX, bifenazate+SX, bifenthrin+SX, bioallethrin+SX, bioresmethrin+SX, bistrifluron+SX, borax+SX, boric acid acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphidephosphide)+SX, carbaryl+SX, carbofuran+SX, carbosulfan+SX, cartap hydrochloride hydrochloride + SX, cartap + SX, chinomethionat + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin AA) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyproflumilast + SX, flanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX, dimetho ... octaborate)+SX, disulfoton+SX, DNOC(2-methyl-4,6-dinitrophenol+SX, doramectin+SX, dried leaves of Dryopterisfilix-mas)+SX、emamectin-benzoate+SX、empenthrin+SX、endosulfan+SX、EPN(O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX、epsilon-metofluthrin+SX、epsilon-momfluorothrin+SX、esfenvalerate+SX、ethiofencarb+SX、ethion+SX、ethiprole+SX、ethoprophos+SX、etofenprox+SX、etoxazole+SX、extract of Artemisia absinthium+SX、extract of neem Azadirachta indica + SX, Cassia nigricans extract + SX, butterfly pea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tanacetum vulgare extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatinoxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, fluorine Flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX,

[0946] gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid acid)+SX、hydramethylnon+SX、hydroprene+SX、imicyafos+SX、imidacloprid+SX、imidaclothiz+SX、imiprothrin+SX、indazapyroxamet+SX、indoxacarb+SX、isocycloseram+SX、isofenphos+SX、isoprocarb+SX、isopropyl-O-(methoxyaminothiophosphoryl) salicylate SX, 3-thoxyaminothiophosphoryl)salicylate+SX, isoxathion+SX, ivermectin+SX, kadethrin+SX, kappa-tefluthrin+SX, kappa-bifenthrin+SX, kinoprene+SX, lambda-cyhalothrin+SX, ledprona+SX, lenoremycin+SX, lepimectin+SX, lime sulfur+SX, lotilaner+SX, lufenuron+SX, machine oiloil+SX、malathion+SX、mecarbam+SX、meperfluthrin+SX、metaflumizone+SX、metam+SX、methamidophos+SX、methidathion+SX、methiocarb+SX、methomyl+SX、methoprene+SX、methoxychlor+SX、methoxyfenozide+SX、methyl bromide+SX、metofluthrin+SX、metolcarb+SX、metoxadiazone+SX、mevinphos+SX、milbemectin+SX、milbemycin oxime+SX、mivorilaner+SX、modoflaner+SX、momfluorothrin+SX、monocrotophos+SX、moxidectin+SX、naled+SX、nicofluprole+SX、nicotine+SX、nicotine-sulfate+SX、nitenpyram+SX、novaluron+SX、noviflumuron+SX、oil of the seeds of Chenopodium anthelminticumanthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, et)+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginate glycolalginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyri minostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX,borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfurylfluoride + SX, tartar emetic emetic+SX, tau-fluvalinate+SX, tebufenozide+SX, tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX, temephos+SX, terbufos+SX, terpene constituents of the extract of chenopodium ambrosioides nearambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-disodium + SX, thiosultap-disodium ultap-monosodium+SX, tigolaner+SX, tiorantraniliprole+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, trifluenfuronate+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, umifoxolaner+SX, vamidothion+SX, wood extract of quassia extract of Quassia amara)+SX, XMC (3,5-dimethylphenyl N-methylcarbamate)+SX, xylylcarb+SX, zeta-cypermethrin+SX, zinc phosphide+SX,

[0947] 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietane-3-yl)benzamide (1241050-20-3)+SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5)+SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methylsulfonyl)-3 -(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)propionamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methylsulfonyl)propionamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-0 9-3) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-butene-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, N-({2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-Fluoro-N-[1-(methylsulfonyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide+SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7)+SX,

[0948] BT crop protein Cry1Ab(BT crop protein Cry1Ab)+SX、BT crop protein Cry1Ac(BT crop protein Cry1Ac)+SX、BT crop protein Cry1Fa(BT crop protein Cry1Fa)+SX、BT crop protein Cry1A.105(BT crop protein Cry1A.105)+SX、BT crop protein Cry2Ab(BTcrop protein Cry2Ab)+SX、BT crop protein Vip3A(BT crop protein Vip3A)+SX、BT crop protein mCry3A(BT crop protein mCry3A)+SX、BT crop protein Cry3Ab(BT cropprotein Cry3Ab)+SX、BT crop protein Cry3Bb(BT crop protein Cry3Bb)+SX、BT crop protein Cry34Ab1 / Cry35Ab1(BT crop protein Cry34Ab1 / Cry35Ab1)+SX, Adoxophyes orana granulosis virus strain BV-0001+SX, Anticarsia gemmatalis mNPV+SX, Autographa californica mNPV+SX, Cydia pomonella GV strain V15+SX, Cydia pomonella GV strain V22+SX, Cryptophlebia leucotreta GV+SX, Dendrolimus punctatus cypovirus+SX, Helicoverpa armigera nuclear polyhedrosis virus BV-0003+SX armigera NPV strain BV-0003)+SX, Helicoverpazea NPV+SX, Lymantria dispar NPV+SX, Mamestra brassicae NPV+SX, MamestraconfigurataNPV)+SX, Neodiprion abietis NPV+SX, Neodiprion lecontei NPV+SX, Neodiprionsertifer NPV+SX, Nosema locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodoptera exigua NPV+SX, Spodoptera littoralis NPV+SX, Spodoptera litura NPV+SX NPV)+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637+SX, Bacillus megaterium+SX, Bacillus sp. strain AQ175+SX, Bacillus sp. strain AQ177+SX, Bacillus sp. strain AQ178+SX, Bacillus sphaericus strain 2362 serotype H5a5b+SX 2362serotypeH5a5b)+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD#32+SXBD#32)+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawai serotype H-7+SX thuringiensissubsp.Aizawai Serotype strain H-7)+SX, Bacillus thuringiensis subsp.Kurstaki strain ABTS351+SX, Bacillus thuringiensis subsp.Kurstaki strain BMP123+SX, Bacillus thuringiensis subsp.Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp.Kurstaki strain EG2348+SX, Bacillus thuringiensis subsp.Kurstaki strain EG7841+SX, Bacillus thuringiensis subsp.Kurstaki strain EG7841)+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 (Bacillus thuringiensis subsp. Kurstaki strain EVB113-19)+SX, Bacillus thuringiensis subsp. Kurstaki strain F810 (Bacillus thuringiensis subsp. Kurstaki strainF810)+SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1+SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. thuringiensis MPPL002+SX subsp.Thuringiensis strain MPPL002)+SX, Bacillus thuringiensis subsp.morrisoni+SX, Bacillus thuringiensis var.colmeri+SX, Bacillus thuringiensis var.darmstadiensis strain 24-91+SX, Bacillus thuringiensis var.dendrolimus+SX, Bacillus thuringiensis var.galleriae+SX, Bacillus thuringiensis var.israelensis strain BMP144+SX, BMP144)+SX, Bacillus thuringiensis var. israelensis serotype strain H-14+SX, Bacillus thuringiensis var. japonensisstrainbuibui)+SX, Bacillus thuringiensis var.sandiego strain M-7+SX, Bacillus thuringiensis var.7216+SX, Bacillus thuringiensis var.aegypti+SX, Bacillus thuringiensis var.T36+SX, Beauveriabassiana strain ANT-03+SX, Beauveriabassiana ATCC74040+SX, Beauveriabassiana strain GHA+SX, Beauveria bassiana strain ... brongniartii)+SX, new heat-killed bacteria A396 strain (Burkholderia rinojensis strain A396)+SX, active purple bacteria PRAA4-1T strain (Chromobacterium subtsugae strain PRAA4-1T)+SX, spindle septum finger spore (Dactyllela ellipsospora)+SX, Dectylaria thaumasia+SX, Minnesota hairy spore (Hirsutella minnesotensis)+SX, Hirsutella rhossiliensis+SX, Hirsutella thompsonii+SX, Lagenidium giganteum+SX, Lecanicillium lecanii strain KV01+SX, Lecanicillium lecanii conidia of strain DAOM198499+SX DAOM198499)+SX, conidia of Lecanicillium lecanii strain DAOM216596+SX, Lecanicillium muscarium strain Ve6+SX, Metarhizium anisopliae strain F52F52)+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52+SX, Metarhizium flavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomyces fumosoroseus Apopka strain 97+SX, Paecilomyces lilacinus strain 251+SX, Paecilomyces tenuipes strain T1+SX, Paenibacillus popilliae+SX, Pasteuria Pn1+SX nishizawaestrain Pn1)+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticilliumchlamydosporium+SX, Verticilliumlecani strain NCIM1312+SX, Wolbachia pipientis+SX.

[0949] Combination of the present component of the above group (b) with the compound of the present invention:

[0950] acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper sulfate sulfate+SX、benalaxyl+SX、benalaxyl-M+SX、benodanil+SX、benomyl+SX、benthiavalicarb+SX、benthiavalicarb-isopropyl+SX、benzovindiflupyr+SX、binapacryl+SX、biphenyl+SX、bitertanol+SX、bixafen+SX、blasticidin-S+SX、Bordeaux mixture mixture)+SX, boscalid+SX, bromothalonil+SX, bromuconazole+SX, bupirimate+SX, captafol+SX, captan+SX, carbendazim+SX, carboxin+SX, carpropamid+SX, chinomethionat+SX, chitin+SX, chloroinconazide+SX, chloroneb+SX, chlorothalonil+SX, chlozolinate+SX, colletochlorinB+SX、copper(II)acetate+SX、copper(II)hydroxide+SX、copperoxychloride+SX、copper(II)sulfate+SX、coumoxystrobin+SX、cyazofamid+SX、cyflufenamid+SX、cymoxanil+SX、cyproconazole+SX、cyprodinil+SX、dichlobentiazox+SX、dichlofluanid+SX、diclocymet+SX、diclomezine+SX、diclor an)+SX, diethofencarb+SX, difenoconazole+SX, diflumetorim+SX, dimethachlone+SX, dimethirimol+SX, dimethomorph+SX, dimoxystrobin+SX, diniconazole+SX, diniconazole-M+SX, dinocap+SX, dipotassium hydrogenphosphite+SX, dipymetitrone+SX, dithianon+SX, dodecylbenzenesulphonic acid bis(ethylenediamine)copper(II) complex salt acid bisethylenediamine copper(II)salt)+SX、dodemorph+SX、dodine+SX、edifenphos+SX、enoxastrobin+SX、epoxiconazole+SX、etaconazole+SX、ethaboxam+SX、ethirimol+SX、etridiazole+SX、extract of Melaleuca alternifolia+SX、extract of Reynoutriasachalinensis)+SX, extract of the cotyledons of lupine plantlets ("BLAD")+SX, extract of Allium sativum+SX, extract of Equisetum arvense+SX, extract of Nasturtium ofTropaeolummajus+SX, famoxadone+SX, fenamidone+SX, fenaminstrobin+SX, fenarimol+SX, fenbuconazole+SX, fenfuram+SX, fenhexamid+SX, fenoxanil+SX, fenpiclonil+SX, fenpicoxamid+SX, fenpropidin+SX, fenpropimorph+SX, fenpyrazamine+SX, fentin acetate+SX, fentin chloride+SX, fentin hydroxide+SX, fentin pyrazine+SX, fentin acetic acid+SX, fentin chloride+SX, fentin hydroxide+SX, fentin pyrazine+SX, fentin acetic acid+SX, fentin acetic acid+SX, fentin chloride+SX, fentin hydroxide+SX, fentin pyrazine ...hydroxide)+SX, ferbam+SX, ferimzone+SX, florylpicoxamid+SX, fluazinam+SX, flubeneteram+SX, fludioxonil+SX, flufenoxadiazam+SX, flufenoxystrobin+SX, fluindapyr+SX, flumetylsulforim+SX, flumorph+SX, fluopicolide+SX, fluopyram+SX, fluopimomide+SX, fluoroimide+SX, fluoxapiprolin+SX, fluoxastrobin +SX, fluoxytioconazole +SX, fluquinconazole +SX, flusilazole +SX, flusulfamide +SX, flutianil +SX, flutolanil +SX, flutriafol +SX, fluxapyroxad +SX, folpet +SX, fosetyl +SX, fosetyl-aluminium +SX, fuberidazole +SX, furaxyl +SX, furametpyr +SX, guazatine +SX, hexaconazole +SX, hymexazole +SX,

[0951] imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate triacetate+SX、inpyrfluxam+SX、iodocarb+SX、ipconazole+SX、ipfentrifluconazole+SX、ipflufenoquin+SX、iprobenfos+SX、iprodione+SX、iprovalicarb+SX、isofetamid+SX、isofluxcypram+SX、isoprothiolane+SX、isopyrazam+SX、isotianil+SX、kasugamycin+SX、kresoxim-methyl+SX、laminarin+SX、leaves and bark of oakQuercus+SX, mancozeb+SX, mandestrobin+SX, mandipropamid+SX, maneb+SX, mefentrifluconazole+SX, mepanipyrim+SX, mepronil+SX, meptyldinocap+SX, metalaxyl+SX, metalaxyl-M+SX, metaylpicoxamid+SX, metconazole+SX, methasulfocarb+SX X, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofurace + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic acid acid + SX, oxpoconazole + SX, oxpoconazole fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogen phosphite + SX,dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyramet ostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract)+SX, quinconazole+SX, quinofumelin+SX, quinoxyfen+SX, quintozene+SX, saponins of Chenopodiumquinoa+SX, seboctylamine+SX, sedaxane+SX, silthiofam+SX, simeconazole+SX, sodium bicarbonatehydrogencarbonate+SX、spiroxamine+SX、streptomycin+SX、sulfur+SX、tebuconazole+SX、tebufloquin+SX、teclofthalam+SX、tecnazene+SX、terbinafine+SX、tetraconazole+SX、thiabendazole+SX、thifluzamide+SX、thiophanate+SX、thiophanate-methyl+SX、thiram+SX、thymol+SX、tiadinil+SX、tolclofos-methyl+SX、 -methyl)+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX, triadimefon+SX, triadimenol+SX, triazoxide+SX, triclopyricarb+SX, tricyclazole+SX, tridemorph+SX, trifloxystrobin+SX, triflumizole+SX, triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX, vinclozolin+SX, yellow mustard powder mustard powder)+SX, zinc thiazole+SX, zineb+SX, ziram+SX, zoxamide+SX,

[0952] N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidine (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidine (2055589-28 -9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidine (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylformamidine (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidine (181782 8-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl 1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S,2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol(2019215-86-0)+SX、1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol(2019215-84-8)+SX、1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile(2018316-13-5 )+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2)+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1)+SX, ({2-methyl-5-[1-(4-methoxy-2-methylphenyl) -1H-pyrazol-3-yl]phenyl}methyl)carbamic acid methyl ester (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098 918-25-1)+SX、5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one(2098918-26-2)+SX、N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX、N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide+SX 、N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide+SX、N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX、N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX、N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX、4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-acetyl-2-(ethylsulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindol-1-yl)butan-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindol-1-yl)butan-2-yl ester + SX, 4-fluoroindol-1-yl) butyl-2-yl bromoester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(3,5-dichloropyridin-2-yl)butyl-2-yl ester + SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)butyl-2-yl ester + SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethy l N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1,

[0953] (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]eth ylN-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanina te) + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide + SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4 -[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N- Methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one+SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester + SX, N-methyl-1-({4-[5- 4-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide + SX, 2-[(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid ethyl ester + SX, 2-[(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid ethyl ester + SX, 2-[(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid ethyl ester + SX, 2-[(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionic acid 1-[(4-{[2-(trifluoromethyl)-1-(4-(2-(trifluoromethyl)-1-methyl)-2-[6-({[1-(1-methyl-1H-tetrazolyl-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide], 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile], 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl )-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-[(2-methylpropionyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 2-{[ 2-{[(oxacyclopentane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine+SX,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine+SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methyl oxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)- 6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine+SX 2-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide+SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N- ((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, Methyl [1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-2-propenoate + SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-propenoate + SX, (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxy-2-propenoate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl- 3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]-2-propenoic acid methyl ester + SX,

[0954] Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo (trademark) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB101)+SX, Bacillus amyloliquefaciens strain DB102+SX, Bacillus amyloliquefaciens strain GB03+SX, Bacillus amyloliquefaciens strain FZB24+SX, Bacillus amyloliquefaciens strain FZB42+SX, Bacillus amyloliquefaciens strain IN937a+SX, Bacillus amyloliquefaciens strain MBI600+SX, Bacillus amyloliquefaciens strain QST713+SX QST713)+SX, Bacillus amyloliquefaciens isolate strain B246+SX, Bacillus amyloliquefaciens F727 strainF727)+SX, Bacillus amyloliquefaciens subsp. plantarum strain D747+SX, Bacillus licheniformis strain HB-2+SX, Bacillus licheniformis strain SB3086+SX, Bacillus pumilus strain AQ717+SX, Bacillus pumilus strain BUF-33+SX, Bacillus pumilus strain GB34+SX, Bacillus pumilus strain QST2808+SX, Bacillus simplex CGF2856+SX. simplexstrain CGF2856)+SX, Bacillus subtilis AQ153 strain (Bacillus subtilis strain AQ153)+SX, Bacillus subtilis AQ743 strain (Bacillus subtilis strain AQ743)+SX, Bacillus subtilis BU1814 strain (Bacillus subtilis strain BU1814)+SX, Bacillus subtilis D747 strain (Bacillus subtilisstrain D747)+SX, Bacillus subtilis DB101 strain (Bacillus subtilis strain DB101)+SX, Bacillus subtilis FZB24 strain (Bacillus subtilis strain FZB24)+SX, Bacillus subtilis GB03 strain (Bacillus subtilis strain GB03)+SX, Bacillus subtilis HAI0404 strain (Bacillus subtilisstrain HAI0404)+SX, Bacillus subtilis strain IAB / BS03+SX, Bacillus subtilis strain MBI600+SX, Bacillus subtilis strain QST30002 / AQ30002+SXQST30002 / AQ30002)+SX, Bacillus subtilis QST30004 / AQ30004 strain (Bacillus subtilis strain QST30004 / AQ30004)+SX, Bacillus subtilis QST713 strain (Bacillus subtilis strain QST713)+SX, Bacillus subtilis QST714 strain (Bacillus subtilis strain QST714)+SX, Bacillus subtilis var.Amyloliquefaciens strain FZB24+SX, Bacillus subtilis strain Y1336+SX, Burkholderia cepacia+SX, Burkholderia cepacia type Wisconsin strain J82+SX J82)+SX, Burkholderia cepacia type Wisconsin strain M54+SX, Candida oleophila strain O+SX, Candida saitoana+SX, Chaetomium cupreum+SX, Clonostachys rosea+SX, Coniothyrium minitans strain CGMCC8325+SX, Coniothyrium minitans strain CON / M / 91-8+SX, Cryptococcus albidus+SX, Erwinia carotovora subsp. carotovora strain CGE234M403+SX CGE234M403)+SX, Fusarium oxysporum strain Fo47+SX, Gliocladium catenulatum strain J1446+SX, Paenibacillus polymyxastrain AC-1+SXAC-1)+SX, Paenibacillus polymyxa strain BS-0105+SX, Pantoea agglomerans strain E325+SX, Phlebiopsis gigantea strain VRA1992+SX, Pseudomonas aureofaciens strain TX-1+SX, Pseudomonas chlororaphis strain 63-28+SX, Pseudomonas chlororaphis strain AFS009+SX, Pseudomonas chlororaphis MA342+SX strain MA342)+SX, Pseudomonas fluorescens strain 1629RS+SX, Pseudomonas fluorescens strain A506+SX, Pseudomonas fluorescens strain CL145A+SX, Pseudomonas fluorescens strain G7090+SX, Pseudomonas sp. strain CAB-02+SX, Pseudomonas syringae strain 742RS+SX, Pseudomonas syringae strain MA-4+SX, Pseudomonas flocculatus PF-A22UL strain + SX, Pseudomonas rhodesia strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SXK61)+SX, Streptomyces lydicus strain WYCD108US+SX, Streptomyces lydicus strain WYCD108US+SX, Streptomyces lydicus strain WYEC108+SX, Talaromyces flavus strain SAY-Y-94-01+SX, Talaromyces flavus strain V117b+SX, Trichoderma asperellum strain ICC012+SX, Trichoderma asperellum SKT-1+SX, Trichoderma asperellum strain T25+SX, Trichoderma asperellum strain T34+SX T34)+SX, Trichoderma asperellum strain TV1+SX, Trichoderma atroviride strain CNCM 1-1237+SX, Trichoderma atroviridestrain LC52+SX, Trichoderma atroviride strain IMI 206040+SX, Trichoderma atroviride strain SC1+SX, Trichoderma atroviride strain SKT-1+SX, Trichoderma atroviride strain T11+SX, Trichoderma gamsii endophytic fungus ICC080+SX strain ICC080)+SX, Trichoderma harzianum strain 21+SX, Trichoderma harzianum strain DB104+SX, Trichoderma harzianum strain DSM 14944+SX14944)+SX, Trichoderma harzianum strain ESALQ-1303+SX, Trichoderma harzianum strain ESALQ-1306+SX, Trichoderma harzianum strain IIHR-Th-2+SX, Trichoderma harzianum strain ITEM908+SX, Trichoderma harzianum strain kd+SX, Trichoderma harzianum strain MO1+SX, Trichoderma harzianum strain SF+SX, Trichoderma harzianum strain T22+SX, T22)+SX, Trichoderma harzianum strain T39+SX, Trichoderma harzianum strain T78+SX, Trichoderma harzianum strain TH35+SX, Trichoderma polysporum strain IMI206039+SX, Trichoderma astromaticum+SX, Trichoderma virens strain G-41+SX, Trichoderma virens strain GL-21+SX, Trichoderma viride+SX, Variovorax paradoxus strain CGF4526+SX, Harpinprotein+SX.

[0955] Combination of the present component of the above group (c) with the compound of the present invention:

[0956] 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) acid)+SX、5-aminolevulinic acid hydrochloride+SX、6-benzylaminopurine+SX、abscisic acid+SX、AVG(aminoethoxyvinylglycine)+SX、anisiflupurin+SX、ancymidol+SX、butralin+SX、calcium carbonate+SX、calcium chloride+SX、calcium formate+SX、calcium peroxide+SX、calcium polysulfide+SX、calcium sulfate+SX、chlormequat-chloride+SX、chlorpropham+SX、choline chloridechloride + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, Gibberellin A A) + SX, Gibberellin A3 + SX, inabenfide + SX, Kinetin + SX, lipochitooligosaccharide SP104 + SX, maleic hydrazide + SX, mefluidide + SX, mepiquat-chloride + SX, oxidized glutathione + SX, paclobutrazol + SX, pendimethalin + SX, prohexadione-calcium + SX, prohydrojasmon + SX, pyraflufen-ethyl + SX, sintofen + SX, sodium 1-naphthaleneacetate + SX, sodium cyanate + SX, cyanate)+SX, thidiazuron+SX, triapenthenol+SX, tribufos+SX, trinexapac-ethyl+SX, uniconazole-P+SX, 2-(naphthalen-1-yl)acetamide+SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid+SX, 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylic acid methyl ester+SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propan-1-ol+SX, Claroideoglomusetunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomusmonosporum + SX, Paraglomus brasillianum + SX, Rhizophagusclarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 strain + SX, Azorhizobiumcaulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH strain + SX, Azospirillum brasilense Ab-V5 strain + SX, Azospirillum brasilense Ab-V6 strain + SX, Azospirillum caulinodans + SX, Azospirillumhalopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 strain + SX, Bradyrhizobium elkanii SEMIA 5019 strain + SX, Bradyrhizobium japonicum TA-11 strain + SX, Bradyrhizobium USDA 110 strain + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 strain + SX, Mesorhizobium ciceri + SX, Mesorhizobium huaguihuakii)+SX, Mesorhizobium loti+SX, Rhizobium etli+SX, Rhizobium galegae+SX, Rhizobium leguminosarum bv. Phaseoli+SX, Rhizobium leguminosarum bv. Trifolii+SX, Rhizobium leguminosarum bv. Viciae+SX, Rhizobium trifolii+SX, Rhizobium tropici+SX, Sinorhizobium fredii+SX, Sinorhizobium truncatula+SX meliloti)+SX, Zucchini Yellow MosaikVirus weak strain+SX.

[0957] Combination of the present component of the above group (d) with the compound of the present invention:

[0958] Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0959] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like in terms of weight ratio (compound of the present invention: present component).

[0960] This compound, the compound of the present invention or composition A can prevent plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, phytomyxea, and bacteria. As fungi, for example, Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota can be cited. Specifically, the following examples can be cited. The scientific names of the plant pathogenic microorganisms that cause each disease are shown in brackets.

[0961] Diseases of rice: blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), seedling blight (Gibberella fujikuroi), yellow wilt (Sclerophthora macrospora), rice blast and panicle blight (Epicoccum nigrum), seedling blight (Trichoderma viride, Rhizopus oryzae), pseudo-sheath blight (red sclerotinia (Waitea circinata), brown sclerotinia (Ceratobasidium setariae), brown sheath blight (Thanatephorus solani) cucumeris))), rice false smut (Ustilaginoidea virens), rice grain smut (Tilletia horrida, Tilletia barclayana);

[0962] Diseases of wheat: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red snow rot (Microdochium nivale, Microdochium majus), small snow rot (Typhula incarnata, Typhula ishikariensis), large snow rot (Sclerotinia borealis), brown snow rot (Pythium spp.), loose smut (Ustilagotritici), bunt (Tilletia caries, Tilletia contesta), eye spot (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), glumen blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), damping-off caused by Rhizoctonia (Rhizoctonia solani), damping-off (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici);

[0963] Diseases of barley: powdery mildew (Blumeria graminis), head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), stripe rust (Puccinia hordei), loose powdery mildew (Ustilago nuda), moire (Rhynchosporium secalis), web spot (Pyrenophora teres), leaf spot (Cochliobolus sativus), leaf stripe (Pyrenophora graminea), Ramularia collo-cygni, and Rhizoctonia solani;

[0964] Diseases of corn: Rust (Puccinia sorghi), Southern Rust (Puccinia polysora), Large Spot (Setosphaeria turcica), Tropical Rust (Physopella zeae), Flax Leaf Blight (Cochliobolus heterostrophus), Anthracnose (Colletotrichum graminicola), Gray Leaf Spot (Cercospora zeae-maydis), Brown Spot (Kabatiella zeae), Dark Leaf Spot (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpellamacrospora), Stem Rot (Fusarium graminicola), graminearum), Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), stalk rot (Physoderma maydis), black swell (Phyllachora maydis);

[0965] Cotton diseases: anthracnose (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria macrospora, Alternaria gossypii), black root rot (Thielaviopsis basicola);

[0966] Coffee diseases: rust (Hemileia vastatrix), leaf spot (Cercospora coffeicola);

[0967] Diseases of rapeseed: Sclerotinia sclerotiorum, black spot (Alternaria brassicae), root rot (Phoma lingam), pale leaf spot (Pyrenopeziza brassicae);

[0968] Sugarcane diseases: rust (Puccinia melanocephela, Pucciniakuehnii), smut (Ustilago scitaminea);

[0969] Diseases of sunflower: rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);

[0970] Diseases of citrus: melanosis (Diaporthe citri), scab (Elsinoe fawcetti), penicillium rot (Penicillium digitatum), penicillium (Penicillium italicum), blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus (Aspergillus niger);

[0971] Apple diseases: Blossom rot (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae), Gymnosporangium yamadae);

[0972] Pear diseases: black spot (Venturia nashicola, Venturia apirina), black spot (Alternaria alternata Japanese pearpathotype), red spot (Gymnosporangium haraeanum);

[0973] Peach diseases: gray spot disease (Monilinia fructicola), black spot disease (Cladosporium carpophilum), brown streak disease (Phomopsis rot) (Phomopsis sp.), leaf curl disease (Taphrina deformans), powdery mildew (Podosphaeraleucotricha);

[0974] Diseases of grapes: black pox (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola), brown spot (Pseudocercospora vitis), white rot (Coniella castaneicola);

[0975] Diseases of persimmon: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf blight (Cercospora kaki, Mycosphaerella nawae), powdery mildew (Phyllactinia kakicola);

[0976] Diseases of figs: rust (Phakopsora nishidana);

[0977] Diseases of cucurbits: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), blight (Phytophthora capsici), damping off (Pythium sp.), and Phomopsis sp. root rot;

[0978] Diseases of tomatoes: ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), sooty mold (Pseudocercospora fuligena), blight (Phytophthora infestans), powdery mildew (Leveillula taurica);

[0979] Eggplant diseases: brown streak (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum), black blight (Corynespora melongenae), leaf mold (Mycovellosiella nattrassii), brown spot (Thanatephorus cucumeris);

[0980] Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophorabrassicae), downy mildew (Peronospora parasitica), white rust (Albugocandida), black spot (Alternaria brassicicola);

[0981] Diseases of onion: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotial neck rot (Botrytis squamosa), leaf blight (Stemphylium vesicarium, Stemphylium botryosum), white rot (Sclerotium rolfsii), white spot leaf blight (Botrytis squamosa);

[0982] Diseases of soybean: purple spot (Cercospora kikuchii), black pox (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown ring rot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), damping-off (Rhizoctonia solani), brown streak (Septoria glycines), spot (Cercospora sojina), sclerotinia (Sclerotinia sclerotiorum), powdery mildew (Microsphaeradiffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death syndrome (Fusarium virguliforme), red crown rot (Calonectria ilicicola), the Diaporthe / Phomopsis complex (Diaporthe longicolla, Diaporthephaseolorum, Phomopsis longicolla);

[0983] Diseases of beans: sclerotinia (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani);

[0984] Diseases of peanut: black spot (Cercospora personata), brown spot (Cercospora arachidicola), white rot (Sclerotium rolfsii), red crown rot (Calonectria ilicicola);

[0985] Diseases of peas: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);

[0986] Potato diseases: early blight (Alternaria solani), blight (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f.sp.subterranea), verticillium wilt (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens), dry rot (Fusarium solani), cancer (Synchytrium endobioticum);

[0987] Strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum);

[0988] Tea diseases: web cake disease (Exobasidium reticulatum), white star disease (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis);

[0989] Diseases of tobacco: brown spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora nicotianae);

[0990] Diseases of sugar beet: brown spot (Cercospora beticola), leaf blight (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (aphanomyces root rot) (Aphanomyces cochlioides), rust (Uromyces betae);

[0991] Rose diseases: scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);

[0992] Diseases of chrysanthemum: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);

[0993] Onion diseases: botrytis leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), small sclerotinia neck rot (Botrytis squamosa);

[0994] Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia (Sclerotinia sclerotiorum), black rot (Sclerotium cepivorum), white rot (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum);

[0995] Radish diseases: black spot (Alternaria brassicicola);

[0996] Sweet potato diseases: Fusarium oxysporum f.sp.batatas, Diaporthedestruens, and Ceratocystis fimbriata.

[0997] Lawn grass diseases: Dollar spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), Pythium wilt (Pythium aphanidermatum), Anthracnose (Colletotrichum caudatum);

[0998] Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola);

[0999] Diseases of lentils: Ascochyta disease (Ascochyta lentis);

[1000] Chickpea diseases: Ascochyta rabiei;

[1001] Diseases of green peppers: anthracnose (Colletotrichum scovillei), powdery mildew (Leveillula taurica), white rot (Sclerotium rolfsii);

[1002] Diseases of mango: Anthracnose (Colletotrichum acutatum);

[1003] Diseases of sweet potatoes: Basal rot (Diaporthe destruens);

[1004] Fruit tree diseases: white feather disease (Rosellinia necatrix), purple feather disease (Helicobasidium mompa);

[1005] Diseases of apples, pears and other fruits after harvest: Mucor rot diseases (Mucorpiriformis);

[1006] Seed diseases or early growth diseases caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia and Diplodia;

[1007] Viral diseases: giant vein disease of lettuce mediated by Olpidium brassicae, viral diseases of various crops mediated by Polymyxa (e.g. Polymyxa betae and Polymyxa graminis);

[1008] Diseases caused by bacteria: bacterial damping off of rice (Burkholderia plantarii), browning of rice inner glume (Pantoea ananatis), bacterial leaf blight of rice (Xanthomonas oryzae pv.oryzae.), bacterial angular spot of cucumber (Pseudomonas syringae pv.lachrymans), bacterial wilt of eggplant (Ralstonia solanacearum), canker of citrus (Xanthomonas citri), soft rot of cabbage (Erwinia carotovora), scab of potato (Streptomyces scabii), black leg of potato (Pectobacterium carotovorum), Dickey asp.), bacterial punch of peach (Pseudomonas syringae, Erwinia igrifluens, Xanthomonas campestris), canker of greengage (Pseudomonas syringae pv. morsprunorum, Erwinia sp.), inner state wilt of corn (Clavibacter michiganensis), crown gall of grapes, olives, peaches, etc. (Xylella fastidiosa), root nodule of Rosaceae plants such as apples, peaches, cherries (Agrobacterium tumefaciens).

[1009] The soybean rust fungus having an amino acid substitution of F129L in the mitochondrial cytochrome b protein is the following soybean rust fungus (scientific name: Phakopsora pachyrhizi): having a mutation in the mitochondrial cytochrome b gene encoding the mitochondrial cytochrome protein, as a result of which the amino acid substitution of F129L occurs, thereby showing resistance to QoI fungicides.

[1010] One embodiment of the plant disease control method of the present invention is a method for controlling soybean rust fungus, which is carried out by treating soybeans or soil in which soybeans are cultivated with the present compound.

[1011] The plant disease control method of the present invention can be carried out by treating plants or soil for cultivating plants with an effective amount of the present compound, the present compound or composition A. Examples of the treatment method include stem and leaf treatment, soil treatment and seed treatment.

[1012] For this compound, the compound of the present invention or composition A, inactive carriers such as solid carriers and liquid carriers and surfactants are usually mixed, and preparation adjuvants such as binders, dispersants, stabilizers, etc. are added as needed, and the preparations are aqueous suspension preparations, oily suspension preparations, oil preparations, emulsions, emulsion preparations, microemulsion preparations, microcapsule preparations, wettable powders, water-dispersible granules, powders, granules, etc. are used. It is not limited to these preparations, and can be prepared as Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271~276, prepared by the FAO / WHOJoint Meeting on Pesticide Specifications (Manual on the Development and Use of Pesticide Standards of the Food and Agriculture Organization of the United Nations and the World Health Organization, Plant Production and Protection Documents of the United Nations Food and Agriculture Organization-271~276, compiled by the Joint Meeting on Pesticide Standards of the Food and Agriculture Organization of the United Nations and the World Health Organization), 2016, ISSN: 0259-2517. The dosage form is used.

[1013] These preparations usually contain the present compound, the compound of the present invention or composition A in an amount of 0.0001 to 99% by weight.

[1014] Examples of the solid support include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powders and granules of chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[1015] Examples of the liquid carrier include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[1016] Examples of the surfactant include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, etc.).

[1017] Other formulation auxiliary agents include binders, dispersants, colorants and stabilizers, and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate and butylated hydroxytoluene.

[1018] In addition, adjuvants can be used as components that enhance or assist the efficacy of the present compound, the compound of the present invention, or composition A. Specifically, adjuvants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[1019] In the present invention, the plant includes the whole plant and specific parts of the plant. Examples of specific parts of the plant include stems and leaves, flowers, ears, fruits, trunks, branches, crowns, seeds, vegetative propagation organs, and seedlings.

[1020] Vegetative propagation organs refer to: among the roots, stems, leaves, etc. of a plant, the parts that have the ability to grow when the parts are cut off from the main body and placed in the soil. As vegetative propagation organs, for example, tuberous roots, creeping roots, bulbs, corms (corm or solid bulb), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings can be cited. It should be noted that stolons are sometimes also called runners, and propagules are also called bulbils, which are divided into broad buds and bulbils. Vine cuttings refer to the slenders (general term for leaves and stems, rootless seedlings (shoots)) of sweet potatoes, Japanese yam, etc. The bulb, corm, tuber, rhizome, stem cutting, root stock or tuber is also collectively called a bulb. The cultivation of tubers is started by planting the tubers in the soil, but the tubers used are usually called seed potatoes.

[1021] Seedlings include seedlings and saplings.

[1022] As a method for controlling plant diseases by applying an effective amount of the present compound, the present compound or composition A to the soil, for example, a method of applying an effective amount of the present compound, the present compound or composition A to the soil before or after transplanting plants. More specifically, for example, hole treatment (hole spreading, hole treatment soil mixing), root treatment (root spreading, root soil mixing, root irrigation, root treatment in the late seedling stage), planting furrow treatment (planting furrow spreading, planting furrow soil mixing), ridge furrow treatment (ridge furrow spreading, ridge furrow soil mixing, growing furrow spreading), sowing furrow treatment (sowing furrow spreading, sowing furrow soil mixing), full treatment (full soil spreading, full soil mixing), ridge side treatment, water surface treatment (water surface application, water surface application after water storage), other soil spreading treatments (leaf surface spreading of granules during the growing period, spreading under the canopy or around the trunk, soil surface spreading, soil surface mixing, hole spreading, ridge ground surface scattering, inter-plant scattering), other irrigation treatments (soil irrigation, irrigation during the seedling period, drug injection treatment, plant base irrigation, drug drip irrigation, chemical solution irrigation), seedling box treatment (seedling box scattering, seedling box irrigation, seedling box drug accumulation), seedling tray treatment (seedling tray scattering, seedling tray irrigation, seedling tray drug accumulation), seedling bed treatment (seedling bed scattering, seedling bed irrigation, nursery bed scattering, seedling immersion), bed soil mixing treatment (bed soil mixing, bed soil mixing before sowing, scattering before covering soil at sowing, scattering after covering soil at sowing, covering soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, rainwater drip soil mixing, planting position treatment, granular calyx scattering, paste fertilizer mixing).

[1023] As seed treatment, for example, the treatment of seeds or vegetative propagation organs by the present compound, the present compound or the composition A can be cited. Specifically, for example, the following can be cited: spraying treatment in which the suspension of the present compound, the present compound or the composition A is made into mist and sprayed on the surface of seeds or the surface of vegetative propagation organs; foaming treatment in which the present compound, the present compound or the composition A is applied to seeds or vegetative propagation organs; immersion treatment in which seeds or vegetative propagation organs are immersed in the liquid of the present compound, the present compound or the composition A for a certain period of time; a method of coating seeds or vegetative propagation organs with a carrier containing the present compound, the present compound or the composition A (coating treatment, pellet coating treatment, etc.). As the above-mentioned vegetative propagation organs, seed potatoes can be cited in particular.

[1024] The seeds or vegetative propagation organs retaining the present compound, the present compound or the composition A in the present invention refer to seeds or vegetative propagation organs in a state where the present compound, the present compound or the composition A is attached to the surface of the seeds or vegetative propagation organs. For the seeds or vegetative propagation organs retaining the present compound, the present compound or the composition A, materials other than the present compound, the present compound or the composition A may be attached before or after the present compound, the present compound or the composition A is attached to the seeds or vegetative propagation organs.

[1025] In addition, when composition A forms a layer on the surface of a seed or a vegetative propagation organ and adheres, the layer is formed by one layer or multiple layers. In addition, when formed by multiple layers, each layer is a layer comprising more than one active ingredient, or is formed by a layer comprising more than one active ingredient and a layer that does not comprise an active ingredient.

[1026] Seeds or vegetative propagation organs containing the present compound, the present compound or composition A can be obtained, for example, by applying a formulation containing the present compound, the present compound or composition A to seeds or vegetative propagation organs using the aforementioned seed treatment method.

[1027] The application amount of the present compound, the present compound or the composition A varies depending on the meteorological conditions, the formulation form, the application period, the application method, the application site, the target disease, the target crop, etc., but in the case of stem and leaf treatment or soil treatment, the application amount of the present compound, the present compound or the composition A is 1000 m 2 Usually 1 to 500 g. In the case of seed treatment, the amount of the present compound, the present compound or composition A is usually 0.001 to 100 g relative to 1 kg of seeds. When the present compound, the present compound or composition A is formulated into an emulsion, a wettable powder, an aqueous suspension, etc., it is usually diluted with water to a concentration of 0.01 to 10000 ppm of the active ingredient and applied. Powders, granules, etc. are usually applied directly.

[1028] The present compound, the present compound or the composition A can be used as a plant disease control agent in agricultural land such as dry fields, paddy fields, lawns, orchards, etc. Examples of the plants include the following plants.

[1029] Corn (dent, hard, soft, popping, glutinous, sweet, non-sweet), rice (long-grain, short-grain, medium-grain, japonica, tropical japonica, indica, Java, upland rice, floating rice, direct-seeded, transplanted, glutinous rice), wheat (bread wheat (hard, soft, medium, red, white), durum, spelt, dense-eared wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, sticky barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland species, Pima species), soybeans (mature seed harvest varieties, branch bean varieties, cut green varieties, each indeterminate growth type, determinate growth type, semi-determinate growth type), peanuts, buckwheat, sugar beets (for sugar production, feed, root vegetables, leafy vegetables, fuel), rapeseed (winter rapeseed type, spring rapeseed type), Canadian rapeseed (winter Canadian rapeseed type, spring Canadian rapeseed type), sunflower (for oil extraction, food , ornamental), sugarcane, tobacco, tea tree, mulberry, Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, potato, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, chamomile, artichoke, lettuce, etc.), Liliaceae vegetables (scallion, onion, garlic, asparagus, etc.), Umbelliferae vegetables (carrot, parsley, celery, parsnip, etc.), Chenopodiaceae vegetables (spinach, thick skin vegetable, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, Japanese yam, taro, pome fruit (apple, pear, Japanese pear, white pear, papaya crabapple, quince, etc.), stone fruit (peach, plum, nectarine, greengage, cherry, apricot, prune, etc.), citrus (Wenzhou mandarin orange, orange, lemon, lime, grapefruit, etc.), nuts (chestnut, walnut, hazelnut, almond, pistachio, cashew, macadamia, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, persimmon, fig, olive, loquat, banana, coffee, date, coconut, ornamental plants, forest plants, lawn grass, forage grass, etc.

[1030] The above-mentioned plants are not particularly limited as long as they are commonly cultivated varieties. The above-mentioned plants also include plants that can be made by natural mating, plants that can be produced by mutation, F1 hybrid plants and genetically modified crops. As genetically modified crops, for example, plants that are endowed with resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase) inhibitors such as isoxathiapiprolin, ALS (acetolactate synthase) inhibitors such as imidacloprid and thifensulfuron, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that can synthesize selective toxins known in Bacillus genus such as Bacillus thuringiensis; plants that can be endowed with specific insecticidal activity by synthesizing gene fragments that are consistent with endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insects.

[1031] Example

[1032] The present invention will be described in more detail below with reference to production examples, reference production examples, formulation examples, and test examples, but the present invention is not limited to these examples.

[1033] In the present specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, c-Pr represents a cyclopropyl group, Bu represents a butyl group, i-Bu represents an isobutyl group, s-Bu represents a sec-butyl group, Ph represents a phenyl group, Bn represents a benzyl group, 2-Thie represents a 2-thienyl group, 2-Fura represents a 2-furyl group, 3-Fura represents a 3-furyl group, 3-Pyraz represents a pyrazol-3-yl group, 4-Pyraz represents a pyrazol-4-yl group, 5-Pyraz represents a pyrazol-5-yl group, 2-Imidaz represents an imidazol-2-yl group, 4-Imidaz represents an imidazol-4-yl group, 3-Py represents a 3-pyridyl group, and 1-Bnfura-2-yl represents a 1-benzofuran-2-yl group. When Ph, 2-Thie, 2-Fura, 3-Pyraz, 4-Pyraz, 5-Pyraz, 2-Imidaz, and 3-Py are substituted with a substituent, the substitution position is also described before the substituent symbol. For example, 2-Me-Ph represents 2-methylphenyl, 2,6-Cl 2 -Ph represents 2,6-dichlorophenyl, 1-Me-4-Imidaz represents 1-methyl-imidazol-4-yl, and 5-Cl-2-Thie represents 5-chloro-2-thienyl.

[1034] When the physical property values ​​of the compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] is recorded. +or [MH] - The conditions of liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[1035] [LC conditions]

[1036] Column: L-column2 ODS, inner diameter 4.6mm, length 30mm, particle size 3μm (National Institute for the Evaluation of Chemical Substances)

[1037] UV measurement wavelength: 254nm

[1038] Mobile phase: Liquid A: 0.1% formic acid in water, Liquid B: 0.1% formic acid in acetonitrile

[1039] Flow rate: 2.0 mL / min

[1040] Pump: LC-20AD (Shimadzu Corporation) 2 units (high pressure gradient)

[1041] Gradient conditions: The solution was delivered with the concentration gradient described in [Table LC1].

[1042] [Table 1]

[1043] [Table LC1]

[1044] time (minute) A liquid (%) B liquid (%) 0.01 90 10 2.00 0 100 4.00 0 100 4.01 90 10

[1045] [MS conditions]

[1046] Detector: LCMS-2020 (manufactured by Shimadzu Corporation)

[1047] Ionization method: DUIS

[1048] First, production examples of the present compounds (including the compounds of the present invention) are shown.

[1049] Production Example 1

[1050] To a mixture of 0.30 g of 3-(4-chlorophenyl)-1H-pyrazole, 0.62 mL of triethylamine and 5 mL of THF was added 0.84 g of p-toluenesulfonyl chloride, and the mixture was stirred at 60° C. for 5 hours. The resulting mixture was subjected to silica gel column chromatography (hexane:ethyl acetate=7:3) to obtain 0.37 g of the present compound 1 represented by the following formula.

[1051] [Chemical formula 18]

[1052]

[1053] This compound 1: 1 H-NMR (CDCl 3)δ: 8.13 (1H, d), 7.95-7.92 (2H, m), 7.76-7.72 (2H, m), 7.38-7.32 (4H, m), 6.66 (1H, d), 2.42 (3H.s).

[1054] Production Example 2

[1055] To a mixture of 0.30 g of 3-phenyl-1H-pyrazole, 0.10 g of sodium hydride (oiliness 60%) and 3 mL of THF was added 0.44 g of pyridine-3-sulfonyl chloride and stirred at room temperature for 3 hours. Water was added to the resulting mixture and extracted with ethyl acetate. The resulting organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 7: 3) to obtain 0.53 g of the present compound 55 shown in the following formula.

[1056] [Chemical formula 19]

[1057]

[1058] Compound 55: 1 H-NMR (CDCl 3 )δ:9.26(1H,d),8.85(1H,dd),8.37-8.34(1H,m),8.15(1H,d),7.82-7.80(2H,m),7.49(1H,ddd),7.43-7.38(3H,m),6.75(1H,d).

[1059] Production Example 1-1

[1060] The compounds produced according to Production Example 1 or Production Example 2 and their physical property values ​​are shown below.

[1061] In the compound represented by formula (IA-1) (hereinafter referred to as compound (IA-1)), R 1 , R 2 , R 3A , R 3B , R 3C The combination of and Z is any combination of compounds listed in [Table A-1], [Table A-2], [Table A-3], and [Table A-4].

[1062] [Chemical formula 20]

[1063]

[1064] [Table 2]

[1065] [Table A-1]

[1066] This compound <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3A ]]> <![CDATA[R 3B ]]> <![CDATA[R 3C ]]> Z 2 H H Cl Br H 2-Me-Ph 3 H H H Cl H 3-Me-Ph 4 H H H Cl H Ph 5 H H H Cl H 2-Me-Ph 6 H H C(O)NH(c-Pr) H H 4-Me-Ph 7 H H C(O)NH(c-Pr) H H Ph 8 H H C(O)NH(Ph) H H Ph 9 H H F Br F Ph 10 H H F Br F 3-Py 11 H H F Br F 2-Cl-Ph 12 H H F Br F 4-Cl-Ph 13 H H F Br F 2-F-Ph 14 H H F Br F 4-F-Ph 15 H H F Br F <![CDATA[2,6-Cl 2 -Ph]]> 16 H H F Br F <![CDATA[3,5-Cl 2 -Ph]]> 17 H H F Br F 3-F-Ph 18 H H F Br F 3-Cl-Ph 19 H H F Br F 2-Me-Ph 20 H H F Br F 3-Me-Ph 21 H H F Br F 4-Me-Ph 22 H H F Br F 4-OMe-Ph 23 H H F Br F 3-OMe-Ph 24 H H F Br F 2-OMe-Ph 25 H H F Br F 2-CN-Ph 26 H H F Br F 3-CN-Ph 27 H H F Br F 4-CN-Ph 28 H H F H H 4-Me-Ph 29 H H H F H 4-Me-Ph 30 H H F Br F 1-Bnfura-2-yl

[1067] [Table 3]

[1068] [Table A-2]

[1069] This compound <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3A ]]> <![CDATA[R 3B ]]> <![CDATA[R 3C ]]> Z 31 H H CONH(c-Pr) H H 1-Me-4-Imidaz 32 H H F Br F 1-Me-4-Imidaz 33 H H F Br F 2-Thie 34 H H F Br F 1-Me-3-Pyraz 35 H H F Br F 1-Me-4-Pyraz 36 H H F Br F 3-Fura 37 H H F Br F 2-Fura 38 H H F Br F 1-Me-2-Imidaz 39 H H F <![CDATA[CF 3 ]]> H 2-Thie 40 H H F Br H 2-Thie 41 H H H SMe H 2-Thie 42 H H H c-Pr H 2-Thie 43 H H H Me H 2-Thie 44 H H H <![CDATA[NO 2 ]]> H 2-Thie 45 H H H C(O)OMe H 2-Thie 46 H H H <![CDATA[NMe 2 ]]> H 2-Thie 47 H H F Br F 5-Cl-2-Thie 48 H H F Br F 1-Me-5-Pyraz 49 H H H Br H 2-Fura 50 H H F Br H 2-Fura 51 H H H Br H 3-Fura 52 H H F Br H 3-Fura 53 H H F Br H 3-Py 54 H H F Br F 2-Cl-3-Py 56 H H F H H 3-Py 57 H H H F H 3-Py 58 H H H OMe H 3-Py

[1070] [Table 4]

[1071] [Table A-3]

[1072]

[1073] [Table 5]

[1074] [Table A-4]

[1075] This compound <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3A ]]> <![CDATA[R 3B ]]> <![CDATA[R 3c ]]> Z 69 H H F Me H 2-Fura 70 H H F Me H 3-Fura 71 H H F Me H 2-Thie 72 H H F Br F 5-Me-2-Fura 73 H H F H F 2-Fura 74 H H F H F 3-Fura 75 H H F H F 2-Thie 76 H H H Me H 2-Fura 77 H H H Me H 3-Fura 78 H H H Me H 2-Thie 79 H H H Cl H 2-Fura 80 H H H Cl H 3-Fura 81 H H H Cl H 2-Thie 82 H H H I H 2-Fura 83 H H H I H 3-Fura 84 H H H I H 2-Thie 85 H H H H H 2-Fura 86 H H H H H 3-Fura 87 H H H H H 2-Thie 88 H H H F H 2-Fura 89 H H H F H 3-Fura 90 H H H F H 2-Thie 91 H H F F H 2-Fura 92 H H F F H 3-Fura 93 H H F F H 2-Thie 94 H H F H H 2-Fura 95 H H F H H 3-Fura 96 H H F H H 2-Thie 97 H H F Me H 3-Py 98 H H F H F 3-Py 99 H H H Me H 3-Py 100 H H F Br F 5-F-3-Py 101 H H F F H 3-Py 102 H H F H H 3-Py

[1076] This compound 2: 1 H-NMR (CDCl 3 )δ:8.21(1H,d),8.13(1H,dd),7.88(1H,d),7.62(1H,d),7.57-7.51(2H,m),7.41(1H,t),7.32(1H,d),6.70(1H,d),2.67(3H,s).

[1077] This compound 3: 1 H-NMR (CDCl 3 )δ:8.14(1H,d),7.86-7.83(2H,m),7.76-7.73(2H,m),7.45-7.42(2H,m),7.38-7.35(2H,m),6.68(1H,d),2.43(3H,s).

[1078] This compound 4: 1 H-NMR (CDCl 3 )δ:8.15(1H,d),8.08-8.05(2H,m),7.83-7.82(1H,m),7.69-7.63(2H,m),7.59-7.54(2H,m),7.34-7.32(2H,m),6.70(1H,d).

[1079] Compound 5: LCMS [M+H] + =333,RT=2.26min

[1080] This compound 6: 1 H-NMR (CDCl 3)δ:8.15-8.14(2H,m),7.93(2H,dt),7.90(1H,dt),7.76(1H,dt),7.45(1H,t),7.34(2H,d),6. 75(1H,d),6.33(1H,s),2.96-2.89(1H,m),2.42(3H,s),0.92-0.88(2H,m),0.68-0.64(2H,m).

[1081] This compound 7: 1 H-NMR (CDCl 3 )δ:8.17-8.15(2H,m),8.08-8.05(2H,m),7.91(1H,dq),7.76(1H,dq),7.66(1H,tt),7.58-7.52(2H, m),7.46(1H,t),6.77(1H,d),6.32(1H,s),2.96-2.90(1H,m),0.92-0.88(2H,m),0.68-0.64(2H,m).

[1082] This compound 8: 1 H-NMR (CDCl 3 )δ:8.31(1H,t),8.19(1H,d),8.09-8.06(2H,m),7.97(1H,dt),7.89(2H,dt),7.69- 7.64(3H,m),7.59-7.52(3H,m),7.43-7.38(2H,m),7.20-7.16(1H,m),6.80(1H,d).

[1083] This compound 9: 1 H-NMR (CDCl 3 )δ:8.17(1H,d),8.09-8.06(2H,m),7.70-7.66(1H,m),7.60-7.55(2H,m),7.43-7.39(2H,m),6.67(1H,d).

[1084] This compound 10: 1 H-NMR (CDCl 3 )δ:9.27(1H,s),8.91(1H,d),8.39-8.36(1H,m),8.19(1H,d),7.54(1H,dd),7.42-7.38(2H,m),6.71(1H,d).

[1085] This compound 11: 1 H-NMR (CDCl 3)δ:8.41-8.35(2H,m),7.63(1H,td),7.55(1H,td),7.51(1H,dd),7.37(2H,d),6.70(1H,d).

[1086] This compound 12: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),8.01(2H,d),7.54(2H,d),7.40(2H,d),6.68(1H,d).

[1087] This compound 13: 1 H-NMR (CDCl 3 )δ:8.30(1H,dd),8.18(1H,m),7.73-7.66(1H,m),7.43-7.37(3H,m),7.20(1H,m),6.71(1H,d).

[1088] This compound 14: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),8.14-8.07(2H,m),7.40(2H,d),7.27-7.21(2H,m),6.68(1H,d).

[1089] This compound 15: 1 H-NMR (CDCl 3 )δ:8.28(1H,d),7.68-7.60(1H,m),7.42(2H,d),7.07(2H,t),6.73(1H,d).

[1090] This compound 16: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.63-7.59(2H,m),7.42(2H,d),7.12(1H,tt),6.72(1H,d).

[1091] This compound 17: 1 H-NMR (CDCl 3 )δ:8.17(1H,d),7.88(1H,d),7.76(1H,dt),7.57(1H,td),7.44-7.35(3H,m),6.70(1H,d).

[1092] This compound 18: 1 H-NMR (CDCl 3)δ:8.17(1H,d),8.03(1H,t),7.97(1H,dq),7.64(1H,dq),7.52(1H,t),7.41(2H,d),6.70(1H,d).

[1093] Compound 19: 1 H-NMR (CDCl 3 )δ:8.23(1H,d),8.15(1H,dd),7.56(1H,td),7.42(1H,t),7.38(2H,d),7.33(1H,d),6.69(1H,d),2.68(3H,s).

[1094] This compound 20: 1 H-NMR (CDCl 3 )δ:8.17(1H,d),7.86(2H,d),7.48-7.44(2H,d),7.41(2H,d),6.67(1H,d),2.44(3H,s).

[1095] This compound 21: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.94(2H,d),7.40(2H,d),7.36(2H,d),6.65(1H,d),2.43(3H,s).

[1096] This compound 22: 1 H-NMR (CDCl 3 )δ:8.15(1H,d),8.00(2H,d),7.40(2H,d),7.01(2H,d),6.64(1H,d),3.87(3H,s).

[1097] This compound 23: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.63(1H,d),7.55(1H,m),7.46(1H,t),7.41(2H,d),7.18(1H,dd),6.67(1H,d),3.87(3H,s).

[1098] This compound 24: 1 H-NMR (CDCl 3 )δ:8.30(1H,d),8.18(1H,dd),7.64(1H,m),7.39(2H,d),7.16(1H,td),6.96(1H,d),6.66(1H,d),3.81(3H,s).

[1099] This compound 25: 1 H-NMR (CDCl 3 )δ:8.47-8.43(2H,m),7.92-7.79(3H,m),7.38(2H,d),6.75(1H,d).

[1100] Compound 26: 1 H-NMR (CDCl 3 )δ:8.34-8.30(2H,m),8.19(1H,d),7.95(1H,dt),7.75(1H,dd),7.40(2H,d),6.72(1H,d).

[1101] This compound 27: 1 H-NMR (CDCl 3 )δ:8.22-8.16(3H,m),7.87(2H,d),7.39(2H,d),6.71(1H,d).

[1102] This compound 28: 1 H-NMR (CDCl 3 )δ:8.14(1H,d),7.96-7.93(2H,m),7.58-7.51(2H,m),7.38-7.33(3H,m),7.05(1H,tdd),6.68(1H,d),2.42(3H,s).

[1103] This compound 29: 1 H-NMR (CDCl 3 )δ:8.12(1H,d),7.95-7.91(2H,m),7.81-7.75(2H,m),7.33(2H,d),7.10-7.04(2H,m),6.64(1H,d),2.41(3H,s).

[1104] This compound 30: 1 H-NMR (CDCl 3 )δ:8.29(1H,d),7.81(1H,d),7.76-7.73(1H,m),7.56-7.49(2H,m),7.44-7.40(2H,m),7.40-7.36(1H,m),6.75(1H,d).

[1105] This compound 31: 1 H-NMR (CDCl 3)δ:8.28(1H,d),8.17(1H,t),7.90-7.87(1H,m),7.80(1H,d),7.79-7.76(1H,m),7.47-7.43(2H,m ),6.77(1H,d),6.35(1H,s),3.77(3H,s),2.95-2.89(1H,m),0.92-0.87(2H,m),0.68-0.64(2H,m).

[1106] This compound 32: 1 H-NMR (CDCl 3 )δ:8.29(1H,d),7.83(1H,d),7.49(1H,d),7.42(2H,d),6.69(1H,d),3.79(3H,s).

[1107] This compound 33: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.91(1H,dd),7.77(1H,dd),7.43(2H,d),7.15(1H,dd),6.68(1H,d).

[1108] This compound 34: 1 H-NMR (CDCl 3 )δ:8.24(1H,d),7.47-7.41(3H,m),6.98(1H,d),6.70(1H,d),3.98(3H,s).

[1109] Compound 35: 1 H-NMR (CDCl 3 )δ:8.14(1H,d),8.04(1H,s),7.91(1H,d),7.42(2H,d),6.66(1H,d),3.97(3H,s).

[1110] This compound 36: 1 H-NMR (CDCl 3 )δ:8.20(1H,s),8.15(1H,d),7.51(1H,t),7.44(2H,d),6.77(1H,dd),6.70(1H,d).

[1111] Compound 37: 1 H-NMR (CDCl 3 )δ:8.22(1H,d),7.63(1H,dd),7.46(1H,dd),7.43(2H,d),6.72(1H,d),6.60(1H,dd).

[1112] This compound 38: 1 H-NMR (CDCl 3 )δ:8.26(1H,d),7.39(2H,d),7.19(1H,d),7.10(1H,s),6.73(1H,d),4.21(3H,s).

[1113] Compound 39: 1 H-NMR (CDCl 3 )δ:8.18(1H,d),7.92(1H,dd),7.77(1H,dd),7.71-7.62(3H,m),7.15(1H,dd),6.74(1H,d).

[1114] This compound 40: 1 H-NMR (CDCl 3 )δ:8.15(1H,d),7.90(1H,dd),7.75(1H,dd),7.63-7.56(2H,m),7.48(1H,dq),7.14(1H,dd),6.69(1H,d).

[1115] This compound 41: 1 H-NMR (CDCl 3 )δ:8.11(1H,d),7.87(1H,dd),7.77-7.74(2H,m),7.72(1H,dd),7.28-7.25(2H,m),7.11(1H,dd),6.69(1H,d),2.51(3H,s).

[1116] This compound 42: 1 H-NMR (CDCl 3 )δ:8.10(1H,d),7.86(1H,dd),7.74-7.69(3H,m),7.11-7.08(3H,m),6.68(1H,d),1.94-1.88(1H,m),1.02-0.97(2H,m),0.74-0.70(2H,m).

[1117] This compound 43: 1 H-NMR (CDCl 3 )δ:8.11(1H,d),7.87(1H,dd),7.74-7.69(3H,m),7.22-7.20(2H,m),7.10(1H,dd),6.69(1H,d),2.37(3H,s).

[1118] This compound 44:1 H-NMR (CDCl 3 )δ:8.29-8.26(2H,m),8.20(1H,d),8.03-7.99(2H,m),7.93(1H,dd),7.78(1H,dd),7.16(1H,dd),6.81(1H,d).

[1119] This compound 45: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),8.09-8.06(2H,m),7.92-7.90(3H,m),7.75(1H,dd),7.13(1H,dd),6.78(1H,d),3.94(3H,s).

[1120] This compound 46: 1 H-NMR (CDCl 3 )δ:8.06(1H,d),7.84(1H,dd),7.74-7.70(2H,m),7.67(1H,dd),7.08(1H,dd),6.71(2H,d),6.64(1H,d),2.99(6H,s).

[1121] This compound 47: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.71(1H,d),7.46-7.42(2H,m),6.98(1H,d),6.70(1H,d).

[1122] This compound 48: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.53(1H,d),7.43-7.38(2H,m),7.00(1H,d),6.7

[1123] 4(1H,d),4.30(3H,s).

[1124] This compound 49: 1 H-NMR (CDCl 3 )δ:8.19(1H,d),7.72-7.69(2H,m),7.61(1H,dd),7.55-7.52(2H,m),7.43(1H,dd),6.74(1H,d),6.58(1H,dd).

[1125] This compound 50: 1 H-NMR (CDCl 3)δ:8.20(1H,d),7.63-7.56(3H,m),7.48(1H,ddd),7.45(1H,dd),6.73(1H,d),6.59(1H,dd).

[1126] This compound 51: 1 H-NMR (CDCl 3 )δ:8.18(1H,dd),8.12(1H,d),7.73-7.70(2H,m),7.56-7.53(2H,m),7.48(1H,t),6.75(1H,dd),6.71(1H,d).

[1127] This compound 52: 1 H-NMR (CDCl 3 )δ:8.19(1H,dd),8.14(1H,d),7.64-7.57(2H,m),7.50-7.47(2H,m),6.76(1H,dd),6.71(1H,d).

[1128] This compound 53: 1 H-NMR (CDCl 3 )δ:9.25(1H,dd),8.88(1H,dd),8.37(1H,ddd),8.18(1H,d),7.60-7.57(2H,m),7.52(1H,ddd),7.46(1H,ddd),6.72(1H,d).

[1129] This compound 54: 1 H-NMR (CDCl 3 )δ:8.72-8.66(2H,m),8.40(1H,d),7.57(1H,dd),7.38-7.34(2H,m),6.74(1H,d).

[1130] This compound 56: 1 H-NMR (CDCl 3 )δ:9.26(1H,dd),8.87(1H,dd),8.37(1H,ddd),8.17(1H,d),7.58-7.50(3H,m),7.40-7.35(1H,m),7.08(1H,m),6.73(1H,d).

[1131] Compound 57: 1 H-NMR (CDCl 3)δ:9.25(1H,dd),8.86(1H,dd),8.35(1H,ddd),8.15(1H,d),7.81-7.76(2H,m),7.52-7.49(1H,m),7.13-7.07(2H,m),6.70(1H,d).

[1132] This compound 58: 1 H-NMR (CDCl 3 )δ:9.24(1H,dd),8.84(1H,dd),8.34(1H,ddd),8.12(1H,d),7.76-7.73(2H,m),7.49(1H,ddd),6.92(2H,dd),6.69(1H,d),3.84(3H,s).

[1133] This compound 61: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.95-7.92(2H,m),7.57(1H,d),7.49(1H,dd),7.34(2H,d),7.06(1H,d),6.63(1H,d),2.42(3H,s).

[1134] This compound 62: 1 H-NMR (CDCl 3 )δ:8.10(1H,d),7.86(1H,dd),7.73(1H,s),7.70(1H,dd),7.59(1H,dd),7. 27-7.24(1H,m),7.10(1H,dd),6.69(1H,d),2.93(4H,q),2.13-2.06(2H,m).

[1135] This compound 63: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.89(1H,dd),7.74(1H,dd),7.60(1H,d),7.53(1H,dd),7.13(1H,dd),7.08(1H,d),6.66(1H,d).

[1136] This compound 64: 1 H-NMR (CDCl 3 )δ:8.22(1H,d),8.16(1H,t),8.11(1H,dd),7.94(1H,dd),7.89(1H,dd),7.79(1H,dd),7.16(1H,dd),6.86(1H,d).

[1137] Compound 65: 1 H-NMR (CDCl 3 )δ:9.03(1H,s),8.49(1H,dd),8.18(1H,d),8.16(1H,dd),7.98(1H,dd),7.92(1H,dd),7.74(1H,dd),7.14(1H,dd),6.81(1H,d).

[1138] Compound 69: 1 H-NMR (CDCl 3 )δ:8.18(1H,d),7.60(1H,dd),7.51-7.47(2H,m),7.43(1H,dd),7.23-7.19(1H,m),6.72(1H,d),6.58(1H,dd),2.29(3H,d).

[1139] This compound 70: 1 H-NMR (CDCl 3 )δ:8.18(1H,dd),8.11(1H,d),7.52-7.47(3H,m),7.24-7.20(1H,m),6.76(1H,dd),6.69(1H,d),2.30(3H,d).

[1140] This compound 71: 1 H-NMR (CDCl 3 )δ:8.12(1H,d),7.88(1H,dd),7.73(1H,dd),7.52-7.47(2H,m),7.23-7.19(1H,m),7.12(1H,dd),6.67(1H,d),2.29(3H,d).

[1141] This compound 72: 1 H-NMR (CDCl 3 )δ:8.20(1H,d),7.46-7.42(2H,m),7.38-7.37(1H,m),6.71(1H,d),6.22-6.21(1H,m),2.37(3H,s).

[1142] This compound 73: 1 H-NMR (CDCl 3 )δ:8.21(1H,d),7.62(1H,dd),7.46(1H,dd),7.38-7.32(2H,m),6.82(1H,tt),6.73(1H,d),6.60(1H,dd).

[1143] This compound 74: 1 H-NMR (CDCl 3 )δ:8.20(1H,dd),8.15(1H,d),7.50(1H,dd),7.39-7.34(2H,m),6.83(1H,tt),6.77(1H,dd),6.70(1H,d).

[1144] Compound 75: 1 H-NMR (CDCl 3 )δ:8.16(1H,d),7.91(1H,dd),7.76(1H,dd),7.39-7.33(2H,m),7.14(1H,dd),6.82(1H,tt),6.68(1H,d).

[1145] This compound 76: 1 H-NMR (CDCl 3 )δ:8.17(1H,d),7.72(2H,dd),7.59(1H,dd),7.41(1H,dd),7.21(2H,dd),6.74(1H,d),6.56(1H,dd),2.37(3H,s).

[1146] Compound 77: 1 H-NMR (CDCl 3 )δ:8.16(1H,dd),8.10(1H,d),7.73(2H,d),7.46(1H,t),7.22(2H,t),6.75(1H,dd),6.71(1H,d),2.38(3H,s).

[1147] Compound 78: 1 H-NMR (CDCl 3 )δ:8.11(1H,d),7.87(1H,dd),7.73(2H,dd),7.70(1H,dd),7.21(2H,t),7.10(1H,dd),6.70(1H,d),2.37(3H,s).

[1148] Compound 79: 1 H-NMR (CDCl 3 )δ:8.19(1H,d),7.77(2H,dt),7.61(1H,dd),7.43(1H,dd),7.38(2H,dt),6.74(1H,d),6.58(1H,dd).

[1149] This compound 80: 1H-NMR (CDCl 3 )δ:8.18(1H,dd),8.12(1H,d),7.78(2H,dt),7.48(1H,t),7.39(2H,dt),6.75(1H,dd),6.71(1H,d).

[1150] This compound 81: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.89(1H,dd),7.77(2H,dt),7.73(1H,dd),7.38(2H,dd),7.12(1H,dd),6.69(1H,d).

[1151] This compound 82: 1 H-NMR (CDCl 3 )δ:8.19(1H,d),7.74(2H,dt),7.61(1H,dd),7.57(2H,dt),7.43(1H,dd),6.74(1H,d),6.58(1H,dd).

[1152] This compound 83: 1 H-NMR (CDCl 3 )δ:8.18(1H,dd),8.12(1H,d),7.76(2H,dt),7.58(2H,dt),7.48(1H,t),6.75(1H,dd),6.71(1H,d).

[1153] This compound 84: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.88(1H,dd),7.76-7.73(3H,m),7.57(2H,dt),7.12(1H,dd),6.70(1H,d).

[1154] This compound 85: 1 H-NMR (CDCl 3 )δ:8.19(1H,d),7.85-7.82(2H,m),7.60(1H,dd),7.44-7.38(4H,m),6.77(1H,d),6.57(1H,dd).

[1155] This compound 86: 1 H-NMR (CDCl 3)δ:8.17(1H,dd),8.12(1H,d),7.86-7.83(2H,m),7.47(1H,t),7.45-7.38(3H,m),6.76(1H,dd),6.75(1H,d).

[1156] This compound 87: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.88(1H,dd),7.86-7.82(2H,m),7.72(1H,dd),7.44-7.36(3H,m),7.11(1H,dd),6.73(1H,d).

[1157] This compound 88: 1 H-NMR (CDCl 3 )δ:8.18(1H,d),7.84-7.79(2H,m),7.60(1H,dd),7.43(1H,dd),7.13-7.07(2H,m),6.72(1H,d),6.58(1H,dd).

[1158] This compound 89: 1 H-NMR (CDCl 3 )δ:8.17(1H,dd),8.12(1H,d),7.85-7.80(2H,m),7.48(1H,t),7.14-7.08(2H,m),6.75(1H,dd),6.70(1H,d).

[1159] This compound 90: 1 H-NMR (CDCl 3 )δ:8.13(1H,d),7.88(1H,dd),7.84-7.80(2H,m),7.73(1H,dd),7.13-7.07(3H,m),6.68(1H,d).

[1160] This compound 91: 1 H-NMR (CDCl 3 )δ:8.19(1H,d),7.70-7.65(1H,m),7.62-7.61(1H,m),7.56-7.52(1H,m),7.44(1H,dd),7.23-7.16(1H,m),6.70(1H,d),6.59(1H,dd).

[1161] This compound 92: 1 H-NMR (CDCl 3)δ:8.19(1H,dd),8.13(1H,d),7.68(1H,ddd),7.57-7.52(1H,m),7.49(1H,t),7.24-7.17(1H,m),6.76(1H,dd),6.68(1H,d).

[1162] This compound 93: 1 H-NMR (CDCl 3 )δ:8.14(1H,d),7.89(1H,dd),7.75(1H,dd),7.71-7.66(1H,m),7.56-7.52(1H,m),7.19(1H,dd),7.14(1H,dd),6.66(1H,d).

[1163] This compound 94: 1 H-NMR (CDCl 3 )δ:8.20(1H,d),7.61-7.54(3H,m),7.44(1H,dd),7.40-7.35(1H,m),7.07(1H,tdd),6.75(1H,d),6.58(1H,dd).

[1164] This compound 95: 1 H-NMR (CDCl 3 )δ:8.19(1H,dd),8.13(1H,d),7.61-7.55(2H,m),7.49(1H,t),7.38(1H,td),7.08(1H,tdd),6.77(1H,dd),6.72(1H,d).

[1165] This compound 96: 1 H-NMR (CDCl 3 )δ:8.14(1H,d),7.90(1H,dd),7.74(1H,dd),7.61-7.54(2H,m),7.37(1H,td),7.13(1H,dd),7.07(1H,tdd),6.71(1H,d).

[1166] This compound 97: 1 H-NMR (CDCl 3 )δ:9.25(1H,dd),8.86(1H,dd),8.36(1H,ddd),8.15(1H,d),7.53-7.47(2H,m),7.45(1H,t),7.21(1H,t),6.70(1H,d),2.29(3H,d).

[1167] This compound 98:1 H-NMR (CDCl 3 )δ:9.26(1H,dd),8.88(1H,dd),8.38(1H,dq),8.19(1H,d),7.53(1H,ddd),7.36-7.30(2H,m),6.85-6.80(1H,m),6.71(1H,d).

[1168] This compound 99: 1 H-NMR (CDCl 3 )δ:9.24(1H,dd),8.84(1H,dd),8.35(1H,ddd),8.13(1H,d),7.71-7.68(2H,m),7.51-7.47(1H,m),7.21(2H,d),6.72(1H,d),2.37(3H,s).

[1169] This compound 100: 1 H-NMR (CDCl 3 )δ:9.08-9.08(1H,m),8.75(1H,d),8.19(1H,d),8.08(1H,ddd),7.43-7.39(2H,m),6.74(1H,d).

[1170] This compound 101: 1 H-NMR (CDCl 3 )δ:9.25(1H,d),8.88(1H,dd),8.36(1H,dt),8.17(1H,d),7.65(1H,ddd),7.54-7.50(2H,m),7.23-7.16(1H,m),6.69(1H,d).

[1171] This compound 102: 1 H-NMR (CDCl 3 )δ:9.26(1H,dd),8.87(1H,dd),8.37(1H,ddd),8.17(1H,d),7.58-7.50(3H,m),7.40-7.35(1H,m),7.08(1H,tdd),6.73(1H,d).

[1172] Production Example 3

[1173] Under reflux, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole 0.29g, 0.40g of intermediate 1, {1,1'-bis(diphenylphosphino)ferrocene}dichloropalladium(II) 0.22g, tripotassium phosphate 0.50g, 1,2-dimethoxyethane 6mL and water 0.1mL were stirred for 13 hours. Water was added to the obtained mixture and extracted with ethyl acetate. The obtained organic layer was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 7: 3) to obtain 0.07g of the present compound 66 shown in the following formula.

[1174] [Chemical formula 21]

[1175]

[1176] This compound 66: 1 H-NMR (CDCl 3 )δ:8.21(1H,d),8.16(1H,d),8.13(1H,s),7.96(1H,dd),7.91(1H,dd),7.74(1H,dd),7.62(1H,dd),7.13(1H,dd),6.77(1H,d).

[1177] Production Example 3-1

[1178] The compounds produced according to Production Example 3 and their physical property values ​​are shown below.

[1179] In compound (IA-1), R 1 , R 2 , R 3A , R 3B , R 3C The combination of and Z is any combination of compounds listed in [Table A-5].

[1180] [Table 6]

[1181] [Table A-5]

[1182]

[1183] Compound 67: LCMS [M+H] + =332,RT=1.75min

[1184] Compound 68: 1 H-NMR (CDCl 3)δ:8.37(1H,dd),8.25(1H,dd),8.21(1H,d),8.04(1H,dd),7.94(1H,dd),7.77(1H,dd),7.15(1H,dd),6.88(1H,d).

[1185] Reference Production Example 1

[1186] 9.38 g of 2-thiophenesulfonyl chloride was added to a mixture of 8.30 g of 3-iodo-1H-pyrazole, 2.05 g of sodium hydride (oil 60%) and 83 mL of THF, and the mixture was stirred at room temperature for 5 hours. Water was added to the obtained mixture, and extraction was performed with ethyl acetate. The obtained organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 7:3) to obtain 13.5 g of intermediate 1 represented by the following formula.

[1187] [Chemical formula 22]

[1188]

[1189] Intermediate 1: 1 H-NMR (CDCl 3 )δ:7.91(1H,d),7.89(1H,dd),7.78(1H,dd),7.15(1H,dd),6.56(1H,d).

[1190] Reference Production Example 1-1

[1191] The intermediate compounds produced according to Reference Production Example 1 and their physical property values ​​are shown below.

[1192] In the compound represented by formula (IIIA-1), X b and Z b The combination is any combination of compounds listed in [Table A-6].

[1193] [Chemical formula 23]

[1194]

[1195] [Table 7]

[1196] [Table A-6]

[1197] intermediate body <![CDATA[X b ]]> <![CDATA[Z b ]]> 2 Br 2-Thie 3 Cl 2-Thie 4 I 3-Py

[1198] Intermediate 2: LCMS [M+H] + =293, RT = 1.75min

[1199] Intermediate 3: LCMS [M+H] +=249, RT = 1.73min

[1200] Intermediate 4: LCMS [M+H] + =336, RT = 1.55min

[1201] Examples of the present compound and the compound of the present invention produced according to the above-mentioned production methods and production examples are shown below.

[1202] [Chemical formula 24]

[1203]

[1204] In the compound represented by formula (A-1) (hereinafter referred to as compound (A-1)), R X1 , R X2 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX1).

[1205] Combination A consists of substituent numbers A1 to A300. Substituent numbers A1 to A300 refer to R in the compound represented by formula (A-1), the compound represented by formula (A-2), the compound represented by formula (A-3), the compound represented by formula (A-4), the compound represented by formula (A-5), the compound represented by formula (A-6), the compound represented by formula (A-7), the compound represented by formula (A-8), the compound represented by formula (A-9), the compound represented by formula (A-10), the compound represented by formula (A-11), and the compound represented by formula (A-12). 1 , R 2 , R 3A , R 3B and R 3C The combination of , hereinafter, is referred to as [substituent number; R 1 ,R 2 ,R 3A ,R 3B ,R 3C ].

[1206] For example, substituent number A3 means: R 3A Ethyl, R 1 , R 2 , R 3B and R 3C Each is a combination of hydrogen atoms.

[1207] Combination A

[1208] [A1;H,H,H,H,H]、[A2;H,H,Me,H,H]、[A3;H,H,Et,H,H]、[A4;H,H,CF 3 ,H,H]、[A5;H,H,c-Pr,H,H]、[A6;H,H,F,H,H]、[A7;H,H,Cl,H,H]、[A8;H,H,Br,H,H]、[A9;H,H,I,H,H]、[A10;H,H,OMe,H,H]、[A11;H,H,SMe,H,H]、[A12;H,H,S(O)Me,H,H]、[A13;H,H,S(O) 2 Me,H,H]、[A14;H,H,C(O)OMe,H,H]、[A15;H,H,C(O)Me,H,H]、[A16;H,H,C(O)NH 2 ,H,H]、[A17;H,H,NMe 2 ,H,H]、[A18;H,H,CN,H,H]、[A19;H,H,NO 2 ,H,H]、[A20;H,H,Ph,H,H]、[A21;H,H,OPh,H,H]、[A22;H,H,OCH 2 Ph,H,H]、[A23;H,H,H,Me,H]、[A24;H,H,H,Et,H]、[A25;H,H,H,CF 3 ,H]、[A26;H,H,H,c-Pr,H]、[A27;H,H,H,F,H]、[A28;H,H,H,Cl,H]、[A29;H,H,H,Br,H]、[A30;H,H,H,I,H]、[A31;H,H,H,OMe,H]、[A32;H,H,H,SMe,H]、[A33;H,H,H,S(O)Me,H]、[A34;H,H,H,S(O) 2 Me,H]、[A35;H,H,H,C(O)OMe,H]、[A36;H,H,H,C(O)Me,H]、[A37;H,H,H,C(O)NH 2 ,H]、[A38;H,H,H,NMe 2 ,H]、[A39;H,H,H,CN,H]、[A40;H,H,H,NO 2 ,H]、[A41;H,H,H,Ph,H]、[A42;H,H,H,OPh,H]、[A43;H,H,H,OCH 2Ph,H]、[A44;Me,H,H,H,H]、[A45;F,H,H,H,H]、[A46;Cl,H,H,H,H]、[A47;Br,H,H,H,H]、[A48;OMe,H,H,H,H]、[A49;H,H,Me,Me,H]、[A50;H,H,Et,Me,H]、[A51;H,H,CF 3 ,Me,H]、[A52;H,H,c-Pr,Me,H]、[A53;H,H,F,Me,H]、[A54;H,H,Cl,Me,H]、[A55;H,H,Br,Me,H]、[A56;H,H,I,Me,H]、[A57;H,H,OMe,Me,H]、[A58;H,H,SMe,Me,H]、[A59;H,H,S(O)Me,Me,H]、[A60;H,H,S(O) 2 Me,Me,H]、[A61;H,H,C(O)OMe,Me,H]、[A62;H,H,C(O)Me,Me,H]、[A63;H,H,C(O)NH 2 ,Me,H]、[A64;H,H,NMe 2 ,Me,H]、[A65;H,H,CN,Me,H]、[A66;H,H,NO 2 ,Me,H]、[A67;H,H,Ph,Me,H]、[A68;H,H,OPh,Me,H]、[A69;H,H,OCH 2 Ph,Me,H]、[A70;H,H,Me,CF 3 ,H]、[A71;H,H,Et,CF 3 ,H]、[A72;H,H,CF 3 ,CF 3 ,H]、[A73;H,H,c-Pr,CF 3 ,H]、[A74;H,H,F,CF 3 ,H]、[A75;H,H,Cl,CF 3 ,H]、[A76;H,H,Br,CF 3 ,H]、[A77;H,H,I,CF 3 ,H]、[A78;H,H,OMe,CF 3 ,H]、[A79;H,H,SMe,CF 3 ,H]、[A80;H,H,S(O)Me,CF 3 ,H]、[A81;H,H,S(O) 2 Me,CF 3,H]、[A82;H,H,C(O)OMe,CF 3 ,H]、[A83;H,H,C(O)Me,CF 3 ,H]、[A84;H,H,C(O)NH 2 ,CF 3 ,H]、[A85;H,H,NMe 2 ,CF 3 ,H]、[A86;H,H,CN,CF 3 ,H]、[A87;H,H,NO 2 ,CF 3 ,H]、[A88;H,H,Ph,CF 3 ,H]、[A89;H,H,OPh,CF 3 ,H]、[A90;H,H,OCH 2 Ph,CF 3 ,H]、[A91;H,H,Me,F,H]、[A92;H,H,Et,F,H]、[A93;H,H,CF 3 ,F,H]、[A94;H,H,c-Pr,F,H]、[A95;H,H,F,F,H]、[A96;H,H,Cl,F,H]、[A97;H,H,Br,F,H]、[A98;H,H,I,F,H]、[A99;H,H,OMe,F,H]、[A100;H,H,SMe,F,H]、[A101;H,H,S(O)Me,F,H]、[A102;H,H,S(O) 2 Me,F,H]、[A103;H,H,C(O)OMe,F,H]、[A104;H,H,C(O)Me,F,H]、[A105;H,H,C(O)NH 2 ,F,H]、[A106;H,H,NMe 2 ,F,H]、[A107;H,H,CN,F,H]、[A108;H,H,NO 2 ,F,H]、[A109;H,H,Ph,F,H]、[A110;H,H,OPh,F,H]、[A111;H,H,OCH 2 Ph,F,H]、[A112;H,H,Me,Cl,H]、[A113;H,H,Et,Cl,H]、[A114;H,H,CF 3,Cl,H]、[A115;H,H,c-Pr,Cl,H]、[A116;H,H,F,Cl,H]、[A117;H,H,Cl,Cl,H]、[A118;H,H,Br,Cl,H]、[A119;H,H,I,Cl,H]、[A120;H,H,OMe,Cl,H]、[A121;H,H,SMe,Cl,H]、[A122;H,H,S(O)Me,Cl,H]、[A123;H,H,S(O) 2 Me,Cl,H]、[A124;H,H,C(O)OMe,Cl,H]、[A125;H,H,C(O)Me,Cl,H]、[A126;H,H,C(O)NH 2 ,Cl,H]、[A127;H,H,NMe 2 ,Cl,H]、[A128;H,H,CN,Cl,H]、[A129;H,H,NO 2 ,Cl,H]、[A130;H,H,Ph,Cl,H]、[A131;H,H,OPh,Cl,H]、[A132;H,H,OCH 2 Ph,Cl,H]、[A133;H,H,Me,Br,H]、[A134;H,H,Et,Br,H]、[A135;H,H,CF 3 ,Br,H]、[A136;H,H,c-Pr,Br,H]、[A137;H,H,F,Br,H]、[A138;H,H,Cl,Br,H]、[A139;H,H,Br,Br,H]、[A140;H,H,I,Br,H]、[A141;H,H,OMe,Br,H]、[A142;H,H,SMe,Br,H]、[A143;H,H,S(O)Me,Br,H]、[A144;H,H,S(O) 2 Me,Br,H]、[A145;H,H,C(O)OMe,Br,H]、[A146;H,H,C(O)Me,Br,H]、[A147;H,H,C(O)NH 2 ,Br,H]、[A148;H,H,NMe 2 ,Br,H]、[A149;H,H,CN,Br,H]、[A150;H,H,NO 2 ,Br,H]、[A151;H,H,Ph,Br,H]、[A152;H,H,OPh,Br,H]、[A153;H,H,OCH 2 Ph,Br,H]、[A154;H,H,Me,I,H]、[A155;H,H,Et,I,H]、[A156;H,H,CF3 ,I,H]、[A157;H,H,c-Pr,I,H]、[A158;H,H,F,I,H]、[A159;H,H,Cl,I,H]、[A160;H,H,Br,I,H]、[A161;H,H,I,I,H]、[A162;H,H,OMe,I,H]、[A163;H,H,SMe,I,H]、[A164;H,H,S(O)Me,I,H]、[A165;H,H,S(O) 2 Me,I,H]、[A166;H,H,C(O)OMe,I,H]、[A167;H,H,C(O)Me,I,H]、[A168;H,H,C(O)NH 2 ,I,H]、[A169;H,H,NMe 2 ,I,H]、[A170;H,H,CN,I,H]、[A171;H,H,NO 2 ,I,H]、[A172;H,H,Ph,I,H]、[A173;H,H,OPh,I,H]、[A174;H,H,OCH 2 Ph,I,H]、[A175;H,H,Me,OMe,H]、[A176;H,H,Et,OMe,H]、[A177;H,H,CF 3 ,OMe,H]、[A178;H,H,c-Pr,OMe,H]、[A179;H,H,F,OMe,H]、[A180;H,H,Cl,OMe,H]、[A181;H,H,Br,OMe,H]、[A182;H,H,I,OMe,H]、[A183;H,H,OMe,OMe,H]、[A184;H,H,SMe,OMe,H]、[A185;H,H,S(O)Me,OMe,H]、[A186;H,H,S(O) 2 Me,OMe,H]、[A187;H,H,C(O)OMe,OMe,H]、[A188;H,H,C(O)Me,OMe,H]、[A189;H,H,C(O)NH 2 ,OMe,H]、[A190;H,H,NMe 2 ,OMe,H]、[A191;H,H,CN,OMe,H]、[A192;H,H,NO 2 ,OMe,H]、[A193;H,H,Ph,OMe,H]、[A194;H,H,OPh,OMe,H]、[A195;H,H,OCH 2Ph,OMe,H] [A196;H,H,Me,OPh,H] [A197;H,H,Et,OPh,H] [A198;H,H,CF 3 ,OPh,H] [A199;H,H,c-Pr,OPh,H] [A200;H,H,F,OPh,H] [A201;H,H,Cl,OPh,H] [A202;H,H,Br,OPh,H] [A203 ;H,H,I,OPh,H] [A204;H,H,OMe,OPh,H] [A205;H,H,SMe,OPh,H] [A206;H,H,S(O)Me,OPh,H] [A207;H,H,S(O) 2 Me,OPh,H] [A208;H,H,C(O)OMe,OPh,H] [A209;H,H,C(O)Me,OPh,H] [A210;H,H,C(O)NH 2 ,OPh,H],[A211;H,H,NMe 2 ,OPh,H],[A212;H,H,CN,OPh,H],[A213;H,H,NO 2 ,OPh,H] [A214;H,H,Ph,OPh,H] [A215;H,H,OPh,OPh,H] [A216;H,H,OCH 2 Ph,OPh,H],[A217;H,H,Me,Et,H],[A218;H,H,Et,Et,H],[A219;H,H,CF 3 ,Et,H] [A220;H,H,c-Pr,Et,H] [A221;H,H,F,Et,H] [A222;H,H,Cl,Et,H] [A223;H,H,Br,Et,H] [A224 ;H,H,I,Et,H] [A225;H,H,OMe,Et,H] [A226;H,H,SMe,Et,H] [A227;H,H,S(O)Me,Et,H] [A228;H,H,S(O) 2 Me,Et,H] [A229;H,H,C(O)OMe,Et,H] [A230;H,H,C(O)Me,Et,H] [A231;H,H,C(O)NH 2 ,Et,H],[A232;H,H,NMe 2 ,Et,H],[A233;H,H,CN,Et,H],[A234;H,H,NO 2,Et,H]、[A235;H,H,Ph,Et,H]、[A236;H,H,OPh,Et,H]、[A237;H,H,OCH 2 Ph,Et,H]、[A238;H,H,Me,Me,Me]、[A239;H,H,Me,Et,Me]、[A240;H,H,Me,CF 3 ,Me]、[A241;H,H,Me,c-Pr,Me]、[A242;H,H,Me,F,Me]、[A243;H,H,Me,Cl,Me]、[A244;H,H,Me,Br,Me]、[A245;H,H,Me,I,Me]、[A246;H,H,Me,OMe,Me]、[A247;H,H,Me,SMe,Me]、[A248;H,H,Me,S(O)Me,Me]、[A249;H,H,Me,S(O) 2 Me,Me]、[A250;H,H,Me,C(O)OMe,Me]、[A251;H,H,Me,C(O)Me,Me]、[A252;H,H,Me,C(O)NH 2 ,Me]、[A253;H,H,Me,NMe 2 ,Me]、[A254;H,H,Me,CN,Me]、[A255;H,H,Me,NO 2 ,Me]、[A256;H,H,Me,Ph,Me]、[A257;H,H,Me,OPh,Me]、[A258;H,H,Me,OCH 2 Ph,Me]、[A259;H,H,F,Me,F]、[A260;H,H,F,Et,F]、[A261;H,H,F,CF 3 ,F]、[A262;H,H,F,c-Pr,F]、[A263;H,H,F,F,F]、[A264;H,H,F,Cl,F]、[A265;H,H,F,Br,F]、[A266;H,H,F,I,F]、[A267;H,H,F,OMe,F]、[A268;H,H,F,SMe,F]、[A269;H,H,F,S(O)Me,F]、[A270;H,H,F,S(O) 2 Me,F]、[A271;H,H,F,C(O)OMe,F]、[A272;H,H,F,C(O)Me,F]、[A273;H,H,F,C(O)NH 2 ,F]、[A274;H,H,F,NMe 2,F],[A275;H,H,F,CN,F],[A276;H,H,F,NO 2 ,F],[A277;H,H,F,Ph,F],[A278;H,H,F,OPh,F],[A279;H,H,F,OCH 2 Ph,F], [A280;H,H,Cl,Me,Cl], [A281;H,H,Cl,Et,Cl], [A282;H,H,Cl,CF 3 ,Cl],[A283;H,H,Cl,c-Pr,Cl],[A284;H,H,Cl,F,Cl],[A285;H,H,Cl,Cl,Cl],[A286;H,H,Cl,Br,Cl],[A287;H, H,Cl,I,Cl], [A288;H,H,Cl,OMe,Cl],[A289;H,H,Cl,SMe,Cl],[A290;H,H,Cl,S(O)Me,Cl],[A291;H,H,Cl,S(O) 2 Me,Cl], [A292; H,H,Cl,C(O)OMe,Cl], [A293; H,H,Cl,C(O)Me,Cl], [A294; H,H,Cl,C(O)NH 2 ,Cl]、[A295;H,H,Cl,NMe 2 ,Cl],[A296;H,H,Cl,CN,Cl],[A297;H,H,Cl,NO 2 ,Cl],[A298;H,H,Cl,Ph,Cl],[A299;H,H,Cl,OPh,Cl],[A300;H,H,Cl,OCH 2 Ph,Cl]

[1209] In compound (A-1), R X1 is methyl, R X2 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX2).

[1210] In compound (A-1), R X1 is a fluorine atom, R X2 , R X3 , R X4 and R X5 Each is a hydrogen atom, R1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX3).

[1211] In compound (A-1), R X1 is a chlorine atom, R X2 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX4).

[1212] In compound (A-1), R X2 is methyl, R X1 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX5).

[1213] In compound (A-1), R X2 is a fluorine atom, R X1 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX6).

[1214] In compound (A-1), R X2 is a chlorine atom, R X1 , R X3 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX7).

[1215] In compound (A-1), R X3 is methyl, R X1 , R X2 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX8).

[1216] In compound (A-1), R X3 is a fluorine atom, R X1 , R X2 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX9).

[1217] In compound (A-1), R X3 is a chlorine atom, R X1 , R X2 , R X4 and R X5 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX10).

[1218] [Chemical formula 25]

[1219]

[1220] In the compound represented by formula (A-2) (hereinafter referred to as compound (A-2)), R X1 , R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX11).

[1221] In compound (A-2), R X1 is methyl, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX12).

[1222] In compound (A-2), R X1 is a fluorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX13).

[1223] In compound (A-2), R X1 is a chlorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX14).

[1224] In compound (A-2), R X2 is methyl, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX15).

[1225] In compound (A-2), R X2 is a fluorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX16).

[1226] In compound (A-2), R X2 is a chlorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX17).

[1227] In compound (A-2), R X3 is methyl, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX18).

[1228] In compound (A-2), R X3 is a fluorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX19).

[1229] In compound (A-2), R X3 is a chlorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX20).

[1230] In compound (A-2), RX4 is methyl, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX21).

[1231] In compound (A-2), R X4 is a fluorine atom, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX22).

[1232] In compound (A-2), R X4 is a chlorine atom, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX23).

[1233] [Chemical formula 26]

[1234]

[1235] In the compound represented by formula (A-3) (hereinafter referred to as compound (A-3)), R X1 , R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX24).

[1236] In compound (A-3), R X1 is methyl, R X2 , R X3 and R X4Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX25).

[1237] In compound (A-3), R X1 is a fluorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX26).

[1238] In compound (A-3), R X1 is a chlorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX27).

[1239] In compound (A-3), R X2 is methyl, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX28).

[1240] In compound (A-3), R X2 is a fluorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX29).

[1241] In compound (A-3), R X2 is a chlorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX30).

[1242] In compound (A-3), R X3 is methyl, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX31).

[1243] In compound (A-3), R X3 is a fluorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX32).

[1244] In compound (A-3), R X3 is a chlorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX33).

[1245] In compound (A-3), R X4 is methyl, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX34).

[1246] In compound (A-3), R X4 is a fluorine atom, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX35).

[1247] In compound (A-3), R X4 is a chlorine atom, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX36).

[1248] [Chemical formula 27]

[1249]

[1250] In the compound represented by formula (A-4) (hereinafter referred to as compound (A-4)), R X1 , R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX37).

[1251] In compound (A-4), R X1 is methyl, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX38).

[1252] In compound (A-4), R X1 is a fluorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX39).

[1253] In compound (A-4), R X1 is a chlorine atom, R X2 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX40).

[1254] In compound (A-4), R X2 is methyl, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX41).

[1255] In compound (A-4), R X2 is a fluorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX42).

[1256] In compound (A-4), R X2 is a chlorine atom, R X1 , R X3 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX43).

[1257] In compound (A-4), R X3 is methyl, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX44).

[1258] In compound (A-4), R X3 is a fluorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX45).

[1259] In compound (A-4), R X3 is a chlorine atom, R X1 , R X2 and R X4 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX46).

[1260] In compound (A-4), R X4 is methyl, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX47).

[1261] In compound (A-4), R X4 is a fluorine atom, R X1 , R X2 and RX3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX48).

[1262] In compound (A-4), R X4 is a chlorine atom, R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX49).

[1263] [Chemical formula 28]

[1264]

[1265] In the compound represented by formula (A-5) (hereinafter referred to as compound (A-5)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX50).

[1266] In compound (A-5), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX51).

[1267] In compound (A-5), R X1 is a fluorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX52).

[1268] In compound (A-5), R X1 is a chlorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX53).

[1269] In compound (A-5), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX54).

[1270] In compound (A-5), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX55).

[1271] In compound (A-5), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX56).

[1272] In compound (A-5), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX57).

[1273] In compound (A-5), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX58).

[1274] In compound (A-5), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX59).

[1275] [Chemical formula 29]

[1276]

[1277] In the compound represented by formula (A-6) (hereinafter referred to as compound (A-6)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX60).

[1278] In compound (A-6), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX61).

[1279] In compound (A-6), R X1 is a fluorine atom, R X2 and R X3Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX62).

[1280] In compound (A-6), R X1 is a chlorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX63).

[1281] In compound (A-6), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX64).

[1282] In compound (A-6), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX65).

[1283] In compound (A-6), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX66).

[1284] In compound (A-6), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX67).

[1285] In compound (A-6), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX68).

[1286] In compound (A-6), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX69).

[1287] [Chemical formula 30]

[1288]

[1289] In the compound represented by formula (A-7) (hereinafter referred to as compound (A-7)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX70).

[1290] In compound (A-7), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX71).

[1291] In compound (A-7), R X1 is a fluorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX72).

[1292] In compound (A-7), R X1 is a chlorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX73).

[1293] In compound (A-7), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX74).

[1294] In compound (A-7), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX75).

[1295] In compound (A-7), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX76).

[1296] In compound (A-7), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX77).

[1297] In compound (A-7), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX78).

[1298] In compound (A-7), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX79).

[1299] [Chemical formula 31]

[1300]

[1301] In the compound represented by formula (A-8) (hereinafter referred to as compound (A-8)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX80).

[1302] In compound (A-8), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A, R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX81).

[1303] In compound (A-8), R X1 is a fluorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX82).

[1304] In compound (A-8), R X1 is a chlorine atom, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX83).

[1305] In compound (A-8), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX84).

[1306] In compound (A-8), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX85).

[1307] In compound (A-8), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX86).

[1308] In compound (A-8), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX87).

[1309] In compound (A-8), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX88).

[1310] In compound (A-8), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX89).

[1311] [Chemical formula 32]

[1312]

[1313] In the compound represented by formula (A-9) (hereinafter referred to as compound (A-9)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX90).

[1314] In compound (A-9), R X1 is methyl, RX2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX91).

[1315] In compound (A-9), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX92).

[1316] In compound (A-9), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX93).

[1317] In compound (A-9), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX94).

[1318] In compound (A-9), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX95).

[1319] In compound (A-9), R X3 is a fluorine atom, RX1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX96).

[1320] In compound (A-9), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX97).

[1321] In compound (A-9), R X1 and R X2 Each is a methyl group, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX98).

[1322] In compound (A-9), R X1 is methyl, R X2 is a fluorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX99).

[1323] In compound (A-9), R X1 is methyl, R X2 is a chlorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX100).

[1324] In compound (A-9), R X1 and RX3 Each is a methyl group, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX101).

[1325] In compound (A-9), R X1 is methyl, R X3 is a fluorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX102).

[1326] In compound (A-9), R X1 is methyl, R X3 is a chlorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX103).

[1327] [Chemical formula 33]

[1328]

[1329] In the compound represented by formula (A-10) (hereinafter referred to as compound (A-10)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX104).

[1330] In compound (A-10), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX105).

[1331] In compound (A-10), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX106).

[1332] In compound (A-10), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX107).

[1333] In compound (A-10), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX108).

[1334] In compound (A-10), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX109).

[1335] In compound (A-10), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3CThe combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX110).

[1336] In compound (A-10), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX111).

[1337] In compound (A-10), R X1 and R X2 Each is a methyl group, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX112).

[1338] In compound (A-10), R X1 is methyl, R X2 is a fluorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX113).

[1339] In compound (A-10), R X1 is methyl, R X2 is a chlorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX114).

[1340] In compound (A-10), R X1 and R X3 Each is a methyl group, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX115).

[1341] In compound (A-10), R X1 is methyl, R X3 is a fluorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX116).

[1342] In compound (A-10), R X1 is methyl, R X3 is a chlorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX117).

[1343] [Chemical formula 34]

[1344]

[1345] In the compound represented by formula (A-11) (hereinafter referred to as compound (A-11)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX118).

[1346] In compound (A-11), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX119).

[1347] In compound (A-11), R X2 is methyl, RX1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX120).

[1348] In compound (A-11), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX121).

[1349] In compound (A-11), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX122).

[1350] In compound (A-11), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX123).

[1351] In compound (A-11), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX124).

[1352] In compound (A-11), R X3is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX125).

[1353] In compound (A-11), R X1 and R X2 Each is a methyl group, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX126).

[1354] In compound (A-11), R X1 is methyl, R X2 is a fluorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX127).

[1355] In compound (A-11), R X1 is methyl, R X2 is a chlorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX128).

[1356] In compound (A-11), R X1 and R X3 Each is a methyl group, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX129).

[1357] In compound (A-11), RX1 is methyl, R X3 is a fluorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX130).

[1358] In compound (A-11), R X1 is methyl, R X3 is a chlorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX131).

[1359] [Chemical formula 35]

[1360]

[1361] In the compound represented by formula (A-12) (hereinafter referred to as compound (A-12)), R X1 , R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX132).

[1362] In compound (A-12), R X1 is methyl, R X2 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX133).

[1363] In compound (A-12), R X2 is methyl, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3Band R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX134).

[1364] In compound (A-12), R X2 is a fluorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX135).

[1365] In compound (A-12), R X2 is a chlorine atom, R X1 and R X3 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX136).

[1366] In compound (A-12), R X3 is methyl, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX137).

[1367] In compound (A-12), R X3 is a fluorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX138).

[1368] In compound (A-12), R X3 is a chlorine atom, R X1 and R X2 Each is a hydrogen atom, R 1 , R 2 , R 3A , R3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX139).

[1369] In compound (A-12), R X1 and R X2 Each is a methyl group, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX140).

[1370] In compound (A-12), R X1 is methyl, R X2 is a fluorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX141).

[1371] In compound (A-12), R X1 is methyl, R X2 is a chlorine atom, R X3 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX142).

[1372] In compound (A-12), R X1 and R X3 Each is a methyl group, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX143).

[1373] In compound (A-12), R X1 is methyl, R X3 is a fluorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A, R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX144).

[1374] In compound (A-12), R X1 is methyl, R X3 is a chlorine atom, R X2 is a hydrogen atom, R 1 , R 2 , R 3A , R 3B and R 3C The combination is any combination of compounds described in combination A (hereinafter referred to as compound group SX145).

[1375] Next, a preparation example is shown. It should be noted that "part" means part by weight. In addition, the present compound S means a compound described in compound groups SX1 to SX145.

[1376] Preparation Example 1

[1377] 35 parts of a mixture of ammonium polyoxyethylene alkyl ether sulfate and silicon dioxide (weight ratio of 1:1), 10 parts of any one of the present compounds S, and 55 parts of water were mixed and finely pulverized by a wet pulverization method to obtain a preparation.

[1378] Preparation Example 2

[1379] 50 parts of any one of the present compounds S, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silicon dioxide were ground and mixed to obtain a preparation.

[1380] Preparation Example 3

[1381] A preparation is obtained by mixing 5 parts of any one of the present compounds S, 9 parts of polyoxyethylene styrylphenyl ether, 5 parts of polyoxyethylene decyl ether (number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

[1382] Preparation Example 4

[1383] 2 parts of any one of the present compounds S, 1 part of silicon dioxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay are ground and mixed, and a suitable amount of water is added, kneaded, granulated with a granulator, and dried to obtain a preparation.

[1384] Preparation Example 5

[1385] 10 parts of any one of the present compounds S was mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark) NS-500LQ and 54 parts of solvent naphtha were added thereto and mixed to obtain a preparation.

[1386] Next, a test example is shown.

[1387] The untreated wells in Test Examples 4, 5, and 6 refer to wells in which the test was carried out under the same conditions as those described in the test examples, except that DMSO was dispensed instead of the DMSO dilution containing the present compound. The untreated wells in Test Examples 15 to 17 refer to wells in which the test was carried out under the same conditions as those described in the test examples, except that DMSO was dispensed instead of the DMSO dilution containing the present compound. In addition, the untreated leaf disc in Test Example 7 refers to a leaf disc in which the test was carried out under the same conditions as those described in the test examples, except that DMSO was dispensed instead of the DMSO dilution containing the present compound. In addition, the untreated wells in Test Examples 10 and 11 refer to wells in which the water dilution containing the preparation containing the present compound was not spread.

[1388] Test Example 1: Control test against wheat leaf blight pathogen (Septoria tritici)

[1389] The compound was diluted with DMSO in a manner containing 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of YBG medium pre-inoculated with spores of wheat leaf blight pathogen was dispensed. The plate was cultured at 18°C ​​for 3 days to proliferate wheat leaf blight pathogen, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of wheat leaf blight pathogen. As a result, various compounds of the present invention showed plant disease control effects.

[1390] Test Example 2: Control test against corn smut fungus (Ustilago maydis)

[1391] The compound was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of a potato extract liquid medium (PDB medium) inoculated with spores of corn smut fungus was dispensed. The plate was cultured at 18°C ​​for 4 days to proliferate corn smut fungus, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of corn smut fungus. As a result, various compounds of the present invention showed plant disease control effects.

[1392] Test Example 3: Control test against barley moire pathogen (Rhynchosporium secalis)

[1393] The compound was diluted with DMSO to contain 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of a potato extract liquid medium (PDB medium) inoculated with spores of barley moire pathogen was dispensed. The plate was cultured at 18°C ​​for 7 days to proliferate barley moire pathogen, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of barley moire pathogen. As a result, various compounds of the present invention showed plant disease control effects.

[1394] Test Example 4: Control test against cucumber gray mold (Botrytis cinerea)

[1395] The compound 24 was diluted with DMSO in a manner containing 150 ppm, and 1 μL was dispensed into a titer plate (96 wells), and then 150 μL of a complete medium pre-inoculated with spores of cucumber gray mold was dispensed. The plate was cultured at 18°C ​​for 4 days to proliferate cucumber gray mold, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of cucumber gray mold. As a result, the growth rate in the wells treated with the above-mentioned compound was less than 50% of the growth rate in the untreated wells.

[1396] Test Example 5: Control test against peach black spot fungus (Cladosporium carpophilum)

[1397] The present compound 79, 80, 81, 89, 92, 93, 96 or 99 was diluted with DMSO to contain 150 ppm, and 1 μL of each was dispensed into a titer plate (96 wells), and then 150 μL of a potato decoction liquid medium (PDB medium) inoculated with spores of peach venison was dispensed into each well. The plate was cultured at 18°C ​​for 5 days to proliferate peach venison, and the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of peach venison. As a result, the growth rate in the wells treated with the abov...

Claims

1. A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with a compound represented by formula (I) or its N-oxide or salt thereof, [Chemical formula 1] In formula (I), Z represents a C6-C10 aryl group or a 5-10 membered aromatic heterocyclic group {the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, R 1 and R 2 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group, and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a hydrogen atom, a halogen atom, a nitro group, a cyano group, NR 8 R 9 , OR 10 、S(O) k R 11 、C(O)R 12 、C(O)OR 13 、C(O)NR 4 R 5 or CR 6 =NOR 7 , R 3 represents a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}, a halogen atom, a nitro group, a cyano group, an NR 8 R 9 , OR 10 、S(O) k R 11 、C(O)R 12 、C(O)OR 13 、C(O)NR 4 R 5 or CR 6 =NOR 7 , Adjacent R 1 and R 3 Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}, a benzene ring or a 5-7-membered aromatic heterocycle {the benzene ring and the 5-7-membered aromatic heterocycle may be substituted with one or more substituents selected from Group E}, Two adjacent R 3 and R 3 Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7-membered non-aromatic heterocycle may be substituted with one or more substituents selected from Group B}, a benzene ring or a 5-7-membered aromatic heterocycle {the benzene ring and the 5-7-membered aromatic heterocycle may be substituted with one or more substituents selected from Group E}, R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C} or a hydrogen atom, p represents 0, 1, 2 or 3, When p is 2 or 3, 2 or 3 R 3 can be the same or different from each other, k represents 0, 1 or 2, Group A: a group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group, a C6-C10 aryl group, a 5-10 membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, a halogen atom and a cyano group, Group B: a group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group C: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group D: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group E: A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

2. The method for controlling plant diseases according to claim 1, wherein: The compound represented by formula (I) or its N-oxide or its salt is the following compound or its N-oxide or its salt, wherein: Z is a phenyl group or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, R 1 and R 2 is a hydrogen atom, R 3 is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8 R 9 , OR 10 , SR 11 、C(O)OR 13 or C(O)NR 4 R 5 , Two adjacent R 3 and R 3 Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle, or a 5-7-membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7-membered non-aromatic heterocycle, and the 5-7-membered aromatic heterocycle may be substituted with one or more halogen atoms}, R 4 , R 5 , R 8 , R 9 , R 10 , R 11 and R 13 The same or different from each other are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, phenyl groups or hydrogen atoms.

3. The method for controlling plant diseases according to claim 1 or claim 2, wherein: The compound represented by formula (I) or its N-oxide or salt thereof is wherein Z is phenyl or 5-6-membered aromatic heterocyclic group {the phenyl and the 5-6-membered aromatic heterocyclic group may be substituted with one or more substituents selected from group F}, R 1 and R 2 is a compound containing a hydrogen atom or its N-oxide or a salt thereof, Group F: A group consisting of a C1-C6 chain hydrocarbon group and a halogen atom.

4. A compound represented by formula (II) or its N-oxide or salt thereof, wherein: The compound does not include 4-{[3-(4-fluorophenyl)-1H-pyrazol-1-yl]sulfonyl}-1,3-dimethyl-1H-pyrazole and 3-(2,3-dihydrobenzofuran-5-yl)-1-(thiophen-2-ylsulfonyl)-1H-pyrazole, [Chemical formula 2] In formula (II), Z a Indicates that it can be selected from group D a A 5-10 membered aromatic heterocyclic group substituted with one or more substituents in R 1a and R 2a The same or different from each other, indicating that they can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C a substituted with one or more substituents in}, hydrogen atom, halogen atom, nitro group, cyano group, NR 8a R 9a , OR 10a 、S(O) m R 11a 、C(O)R 12a 、C(O)OR 13a 、C(O)NR 4a R 5a or CR 6a =NOR 7a , R 3a Indicates that it can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C a substituted with one or more substituents in}, halogen atoms, nitro, cyano, NR 8a R 9a , OR 10a 、S(O) m R 11a 、C(O)R 12a 、C(O)OR 13a 、C(O)NR 4a R 5a or CR 6a =NOR 7a , Adjacent R 1a and R 3a Together with the carbon atoms to which they are bonded, they can form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a substituted with one or more substituents in}, Two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they can form a C4-C7 alicyclic hydrocarbon, a 5-7 membered non-aromatic heterocycle {the C4-C7 alicyclic hydrocarbon and the 5-7 membered non-aromatic heterocycle can be selected from Group B a substituted with one or more substituents in}, a benzene ring or a 5-7 membered aromatic heterocycle {the benzene ring and the 5-7 membered aromatic heterocycle may be selected from Group E a substituted with one or more substituents in}, R 4a , R 5a , R 6a , R 7a , R 8a , R 9a , R 10a , R 11a , R 12a and R 13a The same or different from each other, indicating that they can be selected from group A a wherein at least one substituent in the C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8-membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group is substituted {the C3-C8 alicyclic hydrocarbon group, the 3-8-membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group can be selected from the group C a One or more substituents in {} or a hydrogen atom, q means 1, 2 or 3, When q is 2 or 3, 2 or 3 R 3a can be the same or different from each other, m represents 0, 1 or 2, Group A a : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group, C6-C10 aryl group, 5-10 membered aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group, the 3-8 membered non-aromatic heterocyclic group, the C6-C10 aryl group and the 5-10 membered aromatic heterocyclic group may be selected from the group C a substituted with one or more substituents in}, a halogen atom and a cyano group, Group B a : a group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group C a : a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group D a : a group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group, Group E a : A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

5. The compound according to claim 4, or its N-oxide or salt thereof, wherein: Z a can be selected from group F a A 5-6 membered aromatic heterocyclic group substituted with one or more substituents in R 1a and R 2a is a hydrogen atom, Group F a : A group consisting of a C1-C6 chain hydrocarbon group and a halogen atom.

6. The compound according to claim 4 or 5, or its N-oxide or salt thereof, wherein: R 3a is a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a halogen atom, a nitro group, NR 8a R 9a , OR 10a or SR 11a , Two adjacent R 3a and R 3a Together with the carbon atoms to which they are bonded, they may form a C4-C7 alicyclic hydrocarbon, a 5-7-membered non-aromatic heterocycle, or a 5-7-membered aromatic heterocycle {the C4-C7 alicyclic hydrocarbon, the 5-7-membered non-aromatic heterocycle, and the 5-7-membered aromatic heterocycle may be substituted with one or more halogen atoms}, R 8a , R 9a , R 10a and R 11a The same or different from each other are C1-C6 chain hydrocarbon groups.

7. A composition comprising an inactive support and the compound according to any one of claims 4 to 6, or an N-oxide thereof, or a salt thereof.

8. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound or its N-oxide or salt thereof according to any one of claims 4 to 6, Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): fungicidal active ingredients; Group (c): plant growth regulating ingredients; Group (d): repellent ingredients.

9. A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with an effective amount of the compound according to any one of claims 4 to 6 or its N-oxide or salt thereof, or an effective amount of the composition according to claim 8.

10. Use of the compound according to any one of claims 4 to 6, or its N-oxide or salt thereof, or the composition according to claim 8 for controlling plant diseases.

11. Seeds or vegetative propagation organs, which hold an effective amount of the compound according to any one of claims 4 to 6 or its N-oxide or salt thereof, or an effective amount of the composition according to claim 8.

12. A compound represented by formula (III), [Chemical formula 3] In formula (III), Z b Indicates that it can be selected from group D b A 5-10 membered aromatic heterocyclic group substituted with one or more substituents in X b represents a chlorine atom, a bromine atom, an iodine atom, B(OH)2 or a 4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl group, Group D b : A group consisting of a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a C1-C6 alkoxy group {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by one or more halogen atoms}, a halogen atom, a nitro group and a cyano group.

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