Biaryl compounds and methods for controlling plant diseases

Abstract

This invention provides an excellent method for the prevention and control of plant diseases. Formula (I) [wherein, ring A] 5 This indicates a 5-membered non-aromatic nitrogen-containing heterocycle, etc. (where ring A...) 5 In this context, the atom bonded to D is either a carbon atom or a nitrogen atom, and the atom adjacent to the atom bonded to D forms a ring A. 5 (At least one of the atoms is a nitrogen atom), D represents CR 1 R 2 And so on, where n represents 0, 1, 2, or 3, m represents 0, 1, 2, or 3, q ​​represents 0, 1, 2, 3, 4, or 5, and R 1 and R 2 The same or different from each other indicates C1-C6 chain hydrocarbon groups, etc., R 1 and R 2 They can combine with the carbon atoms they are bonded to to form C3-C8 alicyclic hydrocarbons, etc., R 3 and R 5 The same or different from each other indicates C1-C6 chain hydrocarbon groups, etc., R 4 Indicates C1-C6 chain hydrocarbon groups, etc., R 6 Representing C1-C6 chain hydrocarbon groups, etc., when q is 2, 3, 4 or 5, two adjacent R groups 6 and R 6 They can form C5-C6 alicyclic hydrocarbons together with the carbon atoms they are bonded to. The compounds shown, or their N oxides, or their salts, can be used for the control of plant diseases.

Description

Technical Field

[0001] This patent application asserts priority and interests under the Paris Convention based on Japanese Patent Application No. 2023-174447 (October 6, 2023) and Japanese Patent Application No. 2024-073432 (April 30, 2024), the entire contents of which are incorporated herein by reference.

[0002] This invention relates to biaryl compounds and methods for controlling plant diseases. Background Technology

[0003] Patent document 1 describes biaryl compounds.

[0004] Existing technical documents Patent documents Patent Document 1: International Publication No. 2011 / 005674 Summary of the Invention

[0005] The problem that the invention aims to solve The subject of this invention is to provide excellent methods for the prevention and control of plant diseases.

[0006] Methods for solving problems The inventors of this application conducted research in order to find an excellent method for controlling plant diseases, and found that the compound shown in the following formula (I) has excellent control efficacy against plant diseases.

[0007] That is, the present invention is as follows.

[0008] [1] A method for controlling plant diseases, which is implemented by treating the plant or the soil of cultivated plants with a compound of formula (I) (hereinafter referred to as Compound A) or its N oxide or their salt (hereinafter referred to as Compound A or its N oxide or their salt). [Chemical Formula 1] In the formula, Ring A 5 This indicates a 5-membered non-aromatic nitrogen-containing heterocycle, or a 5-membered aromatic nitrogen-containing heterocycle (where ring A...). 5 In this context, the atom bonded to D is either a carbon atom or a nitrogen atom, and the atom adjacent to the atom bonded to D forms a ring A. 5 (At least one of the atoms is a nitrogen atom). D indicates CR 1 R 2 C=O, C=S, or C=N-OR 7 , n represents 0, 1, 2, or 3. m represents 0, 1, 2, or 3. q represents 0, 1, 2, 3, 4, or 5. R 1 and R 2 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, a phenyl group, a 5 membered aromatic heterocyclic group {the phenyl group and the 5 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 8 SR 9 S(O)R 10 S(O)2R 11 NR 12 R 13 C(O)R 14 C(R) 15 =NOR 16 cyano, nitro, halogen or hydrogen atom R 1 and R 2 They can form C3-C8 alicyclic hydrocarbons or 3-8 membered non-aromatic heterocycles together with the carbon atoms they are bonded to {the C3-C8 alicyclic hydrocarbons and the 3-8 membered non-aromatic heterocycles can be substituted by one or more substituents selected from group B}. R 3 and R 5 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3-8 membered non-aromatic heterocyclic group that can be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, or a 5-6 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group C, OR 17 SR 18 S(O)R 19 S(O)2R 20 NR 21 R 22 C(O)R 23 C(R) 24 =NOR 25 cyano, nitro, or halogen atoms R 4This indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 cyano, nitro, or halogen atoms R 6 This indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group D}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 32 SR 33 S(O)R 34 S(O)2R 35 NR 36 R 37 C(O)R 38 C(R) 39 =NOR 40 cyano, nitro, or halogen atoms R 8 R 12 R 13 R 17 R 21 R 22 R 26 R 27 R 28 R 32 R 36 and R 37"Identical" or "different from each other" refers to C1-C6 chain hydrocarbon groups, C1-C6 alkylsulfonyl groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, and (C2-C8 dialkylamino)carbonyl groups that can be substituted by one or more substituents selected from group A. The carbonyl group, and the (C2-C8 dialkylamino) carbonyl group may be substituted by one or more halogen atoms; C3-C8 alicyclic hydrocarbon group; 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted by one or more substituents selected from group B}; phenyl group; 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}; or hydrogen atom. R 7 R 9 R 16 R 18 R 25 R 31 R 33 and R 40 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or a hydrogen atom. R 10 R 11 R 19 R 20 R 34 and R 35 "Same" or "different from each other" refers to C1-C6 chain hydrocarbon groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {where the C1-C6 alkylamino group and the C2-C8 dialkylamino group can be substituted by one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, phenyl or 5-6 membered aromatic heterocyclic groups {where the phenyl or the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, which can be substituted by one or more substituents selected from group C. R 14 R 23 R 29 and R 38The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxyl group. R 15 R 24 R 30 and R 39 "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more substituents selected from group A. When q is 2, 3, 4, or 5, two adjacent R 6 and R 6 They can form C5-C6 alicyclic hydrocarbons, 5-6 membered non-aromatic heterocycles {the C5-C6 alicyclic hydrocarbons and the 5-6 membered non-aromatic heterocycles can be substituted by one or more substituents selected from group B}, benzene rings, or 5-6 membered aromatic heterocycles {the benzene rings and the 5-6 membered aromatic heterocycles can be substituted by one or more substituents selected from group C} together with the carbon atoms they are bonded to.

[0009] Group A: The group consisting of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted by one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted by one or more substituents selected from Group B}, phenyl groups, 5-6 membered aromatic heterocyclic groups {where the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group C}, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0010] Group B: The group consisting of oxo groups, thio groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms, and cyano groups.

[0011] Group C: Composed of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups, (C1-C6 alkyl)carbonylamino groups, (C1-C6 alkoxy)carbonylamino groups {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C...} The group consisting of 6-alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkylamino)carbonyl, (C2-C8 dialkylamino)carbonyl, (C1-C6 alkyl)carbonylamino, and (C1-C6 alkoxy)carbonylamino, which may be substituted with one or more halogen atoms, and C3-C8 alicyclic hydrocarbon groups, amino, nitro, cyano, hydroxyl, thioalkyl, and halogen atoms that may be substituted with one or more substituents selected from group B.

[0012] Group D: Composed of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group B}, phenyl groups, 5 membered aromatic heterocyclic groups {where the phenyl group and the 5 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group C}, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups. (The following compounds are excluded:) 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)difluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole-2(3H)-one, 2-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole, (3,5-Difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl) methyl ketone, 2-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-oxadiazole, (E)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, (Z)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-ethyl-1,2,4-thiadiazole, 5-Cyclopropyl-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-(trifluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxynitrile, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazol-5(4H)-one, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-ol, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-methoxy-1,2,4-thiadiazole, (2-chlorothiazol-4-yl)(3-fluoro-[1,1'-biphenyl]-4-yl)methanol, 2-Chloro-4-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)thiazole, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 5-Bromo-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxamide, and...

[0013] [2] The plant disease control method as described in [1], wherein the compound represented by formula (I) or its N oxide or their salt is a cyclic A5 Compounds of the formula H1, H2, H3 or H4, or their N oxides or salts, [Chemical Formula 2] [In the formula, # represents the bonding site with D,] X 1 Represents nitrogen atom or CR a4 X 2 Represents nitrogen atom or CR b4 X 3 Represents nitrogen atom or CR c4 (where X) 1 X 2 and X 3 The number of nitrogen atoms is either 0 or 1. Q 1 X 4 and X 5 Combinatorial representation: X 4 For nitrogen atoms, Q 1 For NR a1 X 5 For CR d4 A combination; or, X 4 For CR e4 Q 1 It is an oxygen atom, a sulfur atom, or NR. b1 X 5 Nitrogen atom or CR f4 The combination Q 2 Represents oxygen atom or NR c1 X 7 Represents nitrogen atom or CR g4 , Q 3 Represents sulfur atoms or NR d1 , R a4 R b4 R c4 R d4 R e4 R f4 R g4 R h4 R i4 and R j4"Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 cyano, nitro, halogen or hydrogen atom R a1 R b1 R c1 and R d1 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or a C(O)R group. 29 Or hydrogen atoms.

[0014] [3] The plant disease control method as described in [2], wherein the compound represented by formula (I) or its N oxide or their salt is a cyclic A 5 Compounds of which are represented by the group H1, or their N oxides or salts.

[0015] [4] The plant disease control method as described in [2], wherein the compound represented by formula (I) or its N oxide or their salt is a cyclic A 5 Compounds of which are represented by the group H2, or their N oxides or salts.

[0016] [5] The plant disease control method as described in [2], wherein the compound represented by formula (I) or its N oxide or their salt is a cyclic A 5 Compounds of which are represented by the group H3 or their N oxides or salts.

[0017] [6] The plant disease control method as described in [2], wherein the compound represented by formula (I) or its N oxide or their salt is a cyclic A 5 Compounds of which are represented by the group H4, or their N oxides or salts.

[0018] [7] The compound shown in formula (II) (hereinafter referred to as compound A of the present invention) or its N oxide or salt thereof (hereinafter referred to as compound A of the present invention or its N oxide or salt thereof as compound of the present invention). [Chemical Formula 3] In the formula, Ring A 5a This indicates a 5-membered aromatic nitrogen-containing heterocycle (where ring A...). 5a In the middle, with CR 1a R 2a The bonded atoms are carbon or nitrogen atoms, and, with CR 1a R 2a The bonded atoms are adjacent and form a ring A 5a (At least one of the atoms is a nitrogen atom). na represents 0, 1, 2, or 3. ma represents 0, 1, 2, or 3. qa represents 0, 1, 2, 3, 4, or 5. R 1a and R 2a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a phenyl groups with one or more substituents, OR 8a SR 9a S(O)R 10a S(O)2R 11a NR 12a R 13a C(O)R 14a C(R) 15a =NOR 16a cyano, nitro, halogen or hydrogen atom R 1a and R 2a They can form C3-C8 alicyclic hydrocarbons or 3-8 membered non-aromatic heterocycles together with the carbon atoms they are bonded to {the C3-C8 alicyclic hydrocarbons and the 3-8 membered non-aromatic heterocycles can be selected from group B} a Substitution of one or more substituents in the middle. R 3a and R 5a The same or different from each other indicates that they can be selected from group A. aThe C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17a SR 18a S(O)R 19a S(O)2R 20a NR 21a R 22a C(O)R 23a C(R) 24a =NOR 25a cyano, nitro, or halogen atoms R 4a This indicates that it can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in OR 26a NR 27a R 28a C(R) 29a =NOR 30a cyano, nitro, or halogen atoms R 6a Indicates that it can be selected from group E a A C1-C6 chain hydrocarbon group substituted with one or more substituents, which can be selected from group B a The C3-C8 alicyclic hydrocarbon group, phenyl group, or 5-6 membered aromatic heterocyclic group substituted with one or more substituents {the phenyl group and the 5-6 membered aromatic heterocyclic group can be selected from group C} a Substitution of one or more substituents in OR 31a SR 32a S(O)R 33a S(O)2R 34a NR 35a R 36a C(O)R 37a C(R) 38a =NOR 39a cyano, nitro, or halogen atoms R 8a R 12a R 13a R 17a R 31a R 21a R22a and R 35a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group { phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group C} a One or more substituents in the group, or hydrogen atoms, R 36a This indicates that it can be selected from group A. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 7a R 9a R 10a R 18a R 19a R 25a R 32a R 33a R 34a and R 39a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B}a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 11a and R 20a The same or different from each other indicates that they can be selected from group A. a The following are included: C1-C6 chain hydrocarbon groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {where the C1-C6 alkylamino group and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, and 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 14a and R 23a The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxyl group. R 15a R 24a and R 38a The same or different from each other indicates that they can be selected from group A. a One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom are substituted. R 26a R 27a and R 28a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group, or hydrogen atoms, R30a This indicates that it can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in the middle. R 29a This indicates that it can be selected from group D. a One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom are substituted. R 37a This indicates that a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, or a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}.

[0019] Group A a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a One or more substituents in the group { phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group C} a The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0020] Group B a The group consisting of oxo groups, thio groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms, and cyano groups.

[0021] Group C aComposed of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups, (C1-C6 alkyl)carbonylamino groups, (C1-C6 alkoxy)carbonylamino groups {the C1-C6 chain hydrocarbon group, the C1- The C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group, and the (C1-C6 alkoxy)carbonylamino group may be substituted with one or more halogen atoms; and may be selected from group B. a The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, thioalkyl groups, and halogen atoms substituted with one or more substituents.

[0022] Group D a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0023] Group E a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a The group consisting of one or more substituents, phenyl, 5-membered aromatic heterocyclic group, halogen atom, cyano, nitro, hydroxyl and thioalkyl groups. (The following compounds are excluded:) 4-((3,4,5-tribromo-1H-pyrazol-1-yl)methyl)-[1,1'-biphenyl]-3-ol, 5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-3-methyl-1,2,4-oxadiazole, 3-(chloromethyl)-5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-1,2,4-oxadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)difluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole-2(3H)-one, 2-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole, (3,5-Difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl) methyl ketone, 2-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-oxadiazole, (E)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, (Z)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-ethyl-1,2,4-thiadiazole, 5-Cyclopropyl-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-(trifluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxynitrile, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazol-5(4H)-one, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-ol, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-methoxy-1,2,4-thiadiazole, (2-chlorothiazol-4-yl)(3-fluoro-[1,1'-biphenyl]-4-yl)methanol, 2-Chloro-4-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)thiazole, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 5-Bromo-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxamide, and...

[0024] [8] The compound as described in [7] or its N oxide or salt thereof, wherein the ring A 5a It is a group represented by the formula H1a, H2a, H3a or H4a. [Chemical Formula 4] [In the formula, #] a Indicates CR 1a R 2a The bonding site, X 1a Represents nitrogen atom or CR a4a X 2a Represents nitrogen atom or CR b4a X 3a Represents nitrogen atom or CR c4a (where X) 1a X 2a and X 3a The number of nitrogen atoms is either 0 or 1. Q 1a X 4a X 5a Combinatorial representation: X 4a For nitrogen atoms, Q 1a For NR a1a X 5a For CR d4a A combination; or, X 4a For CR e4a Q 1a It is an oxygen atom, a sulfur atom, or NR. b1a X 5a Nitrogen atom or CR f4a The combination Q 2a Represents oxygen atom or NR c1a X 7a Represents nitrogen atom or CR g4a , Q 3a Represents sulfur atoms or NR d1a , R a4a R b4a R c4a R d4a R e4a R f4a R g4a R h4a R i4a and R j4a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in OR 26a NR 27a R 28a C(R) 29a =NOR 30a cyano, nitro, halogen or hydrogen atom R a1a R b1a R c1a and R d1a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can replace a cyano group or a hydrogen atom.

[0025] [9] A composition comprising an inactive support and the compound described in [7] or [8] or its N oxide or salt thereof.

[0026]

[10] A composition comprising one or more ingredients selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound described in [7] or [8] or its N oxide or salt thereof. Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients; Group (b): Bactericidal active ingredients; Group (c): Plant growth regulators; Group (d): Repellent component.

[0027]

[11] A method for controlling plant diseases, which is carried out by treating the soil of plants or cultivated plants with an effective amount of the compound described in [7] or [8] or its N oxide or salt thereof, or an effective amount of the composition described in

[10] .

[0028] The use of the compounds described in

[12] , [7] or [8], or their N oxides or salts, or the compositions described in

[10] for the control of plant diseases.

[0029]

[13] A seed or vegetative reproductive organ that retains an effective amount of the compound described in [7] or [8] or its N oxide or salt thereof or an effective amount of the composition described in

[10] .

[0030]

[14] The compound shown in formula (III) (hereinafter referred to as intermediate A). [Chemical Formula 5] In the formula, X n1 Represents halogen atoms, R n1 R n2 R n3 and R n5 The same or different from each other indicates hydrogen atom, halogen atom, methyl or methoxy atom. E n1 and R n4 Combinatorial representation: E n1 Halogen atoms, R n4 It is a combination of hydrogen atoms, methyl groups, or methoxy groups; or, E n1 It is a cyano group, C(O)OH, or C(NH2)=NOR n6 , R n4 It is a combination of hydrogen atoms, halogen atoms, methyl or methoxy groups. R n6 This indicates a C1-C6 alkyl carbonyl group, or a hydrogen atom, that can be substituted by one or more halogen atoms.

[0031]

[15] The compound shown in formula (IV) (hereinafter referred to as intermediate B), [Chemical Formula 6] In the formula, R m1 Indicates a chlorine atom, bromine atom, or iodine atom. R m2 Represents halogen atoms, R m3 Indicates hydrogen atom, halogen atom, methyl or methoxy group, E m1 This indicates that 1,2,4-thiadiazole-3-yl, 1,2,4-oxadiazole-3-yl {the 1,2,4-thiadiazole-3-yl and the 1,2,4-oxadiazole-3-yl can be selected from group A} m1 Substitution of one or more substituents, 1,2,3-triazol-2-yl, or isothiazol-3-yl {the 1,2,3-triazol-2-yl and the isothiazol-3-yl may be selected from group B} m1 Substitution of one or more substituents in the middle.

[0032] Group A m1 The group consisting of C1-C4 alkyl, C1-C4 alkoxy, cyclopropyl and CF3 groups.

[0033] Group B m1 The group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 alkoxy groups, C1-C4 haloalkyl groups, C1-C4 haloalkoxy groups, and cyclopropyl groups.

[0034] Invention Effects This invention enables the prevention and control of plant diseases. Detailed Implementation

[0035] The substituents in this invention will be explained.

[0036] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms.

[0037] When a substituent is replaced by two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0038] Regarding the phrase "can be substituted by one or more substituents selected from group X" in this specification (X refers to A, B, C, D, A...), a B a C a D a and E a The statement that "any one of the substituents in X" means that in the presence of more than two substituents selected from group X, these substituents may be the same or different.

[0039] (R) in this instruction manual 4 ) n This statement refers to the case where n is 2 or 3, multiple R 4 They can be the same or different.

[0040] (R) in this instruction manual 5 ) m This statement refers to the case where m is 2 or 3, and multiple R... 5 They can be the same or different.

[0041] (R) in this instruction manual 6 ) q This statement refers to the case where q is 2, 3, 4, or 5, and multiple R... 6 They can be the same or different.

[0042] (R) in this instruction manual 4a ) na This statement refers to the case where na is 2 or 3, and multiple R... 4a They can be the same or different.

[0043] (R) in this instruction manual 5a ) ma This statement refers to the case where ma is 2 or 3, and multiple R... 5a They can be the same or different.

[0044] (R) in this instruction manual 6a ) qa This expression refers to the case where qa is 2, 3, 4, or 5, and multiple R... 6a They can be the same or different.

[0045] In this specification, expressions such as "CX-CY" refer to carbon atoms ranging from X to Y. For example, expressions such as "C1-C6" refer to carbon atoms ranging from 1 to 6.

[0046] The term "chain hydrocarbon group" refers to alkyl, alkenyl, or alkynyl groups.

[0047] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl.

[0048] Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl.

[0049] Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl.

[0050] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, and hexyloxy.

[0051] Examples of alkylthioalkyl groups include methylthioalkyl, ethylthioalkyl, isopropylthioalkyl, and hexylthioalkyl.

[0052] Examples of alkyl sulfinyl groups include methyl sulfinyl, ethyl sulfinyl, isopropyl sulfinyl, and hexyl sulfinyl.

[0053] Examples of alkyl sulfonyl groups include methanesulfonyl, ethanesulfonyl, isopropanesulfonyl, and hexanesulfonyl.

[0054] Examples of alkyl carbonyl groups include acetyl and propionyl.

[0055] Examples of alkoxycarbonyl groups include methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl.

[0056] Examples of alicyclic hydrocarbons include cyclobutene ring, cyclopentene ring, cyclopentadiene ring, cyclohexene ring, cyclohexadiene ring, and cycloheptene ring.

[0057] Examples of alicyclic hydrocarbon groups include cycloalkyl or cycloalkenyl groups.

[0058] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0059] Examples of cycloalkenyl groups include cyclopentenyl and cyclohexenyl.

[0060] Examples of non-aromatic heterocycles include dihydrofuran ring, dihydrothiophene ring, dihydropyrrole ring, 1,3-dioxocyclopentane ring, pyran ring, and dihydropyran ring.

[0061] Examples of aromatic heterocycles include furan rings, thiophene rings, pyrrole rings, pyrazole rings, imidazole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, triazole rings, oxadiazole rings, thiadiazole rings, pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings.

[0062] Examples of aromatic heterocyclic groups include 5-membered aromatic heterocyclic groups such as pyrroleyl, furanyl, thiophenyl, pyrazolyl, imidazoleyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, and thiazolyl; and 6-membered aromatic heterocyclic groups such as pyridyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetraazinyl.

[0063] Examples of non-aromatic heterocyclic groups include acridinel, oxadiazolyl, thiohexacyclopropane, aziridine, oxadiazolyl, thiohexacyclobutane, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, pyrazolinyl, pyrazolinyl, imidazolinyl, imidazolinyl, oxazolinyl, thiazolinyl, oxazolinyl, thiazolinyl, isoxazolinyl, isoxazolinyl, isothiazolinyl, isothiazolinyl, isothiazolinyl, dioxadiazolinyl, dioxadiazolinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiaranyl, aziridine, oxadiazolinyl, and thiohexacyclohexacyclobutane.

[0064] Ring A in Equation (I) 5 It refers to the formula (A) 5 The group shown in -1) represents a 5-membered non-aromatic nitrogen-containing heterocycle, or a 5-membered aromatic nitrogen-containing heterocycle (wherein ring A...). 5 In this context, the atom bonded to D is either a carbon atom or a nitrogen atom, and the atom adjacent to the atom bonded to D forms a ring A. 5 (At least one of the atoms is a nitrogen atom). [Chemical Formula 7] [In the formula, # indicates the same meaning as in the preceding text.]

[0065] As described in equation (I), ring A 5 by n R 4 Replaced by n R 4 Replaced ring A 5 It refers to the formula (A) 5 -2) shows a partial structure. [Chemical Formula 8] [In the formula, # and R] 4 And n has the same meaning as in the previous text.

[0066] Formula (A) 5 -2) shows the n R's 4 Replaced ring A 5 That is, it means being n R's 4 Substituted 5-membered non-aromatic nitrogen-containing heterocycle, or replaced by n R 4 Substituted 5-membered aromatic nitrogen-containing heterocycle (where ring A) 5 In this context, the atom bonded to D is either a carbon atom or a nitrogen atom, and the atom adjacent to the atom bonded to D forms a ring A. 5 (At least one of the atoms is a nitrogen atom).

[0067] As formula (A) 5 The groups shown in -2) can be exemplified by, for example, those shown in formulas H1, H2, H3, and H4. [Chemical Formula 9] [In the formula, the symbols have the same meaning as in the preceding text.]

[0068] Ring A in Equation (II) 5a It refers to the formula (A) 5a The group shown in -1) represents a 5-membered aromatic nitrogen-containing heterocycle (where ring A...). 5a In the middle, with CR 1a R 2a The bonded atoms are carbon or nitrogen atoms, and, with CR 1a R 2a The bonded atoms are adjacent and form a ring A 5a (At least one of the atoms is a nitrogen atom).

[0069] [Chemical Formula 10] [In the formula, #] a This indicates the same meaning as in the preceding text.

[0070] As described in equation (II), ring A 5a be na a R 4a Replaced by na R 4a Replaced ring A 5a It refers to the formula (A) 5a -2) shows a partial structure. [Chemical Formula 11] [In the formula, #] a R 4a And na has the same meaning as in the previous text.

[0071] Formula (A) 5a -2) shows the na R 4a Replaced ring A 5a That is, it means that na R 4a Substituted 5-membered aromatic nitrogen-containing heterocycle (where ring A) 5a In the middle, with CR 1a R 2a The bonded atoms are carbon or nitrogen atoms, and, with CR 1a R 2a The bonded atoms are adjacent and form a ring A 5a (At least one of the atoms is a nitrogen atom).

[0072] As formula (A) 5a -2) The groups shown can be exemplified by those shown in formulas H1a, H2a, H3a, and H4a. [Chemical Formula 12] [In the formula, the symbols have the same meaning as in the preceding text.]

[0073] 4-((3,4,5-tribromo-1H-pyrazol-1-yl)methyl)-[1,1'-biphenyl]-3-ol is a compound shown in the following formula.

[0074] [Chemical Formula 13] 5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-3-methyl-1,2,4-oxadiazole is a compound represented by the following formula.

[0075] [Chemical Formula 14] 3-(chloromethyl)-5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-1,2,4-oxadiazole is a compound shown in the following formula.

[0076] [Chemical Formula 15] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole is a compound represented by the following formula.

[0077] [Chemical Formula 16] 3-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole is a compound represented by the following formula.

[0078] [Chemical Formula 17] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)difluoromethyl)-1,2,4-thiadiazole is a compound represented by the following formula.

[0079] [Chemical Formula 18] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole-2(3H)-one is a compound shown in the following formula.

[0080] [Chemical Formula 19] 2-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole is a compound represented by the following formula.

[0081] [Chemical Formula 20] (3,5-Difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl) methyl ketone is a compound shown in the following formula.

[0082] [Chemical Formula 21] 2-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-oxadiazole is a compound represented by the following formula.

[0083] [Chemical Formula 22] (E)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime is a compound shown in the following formula.

[0084] [Chemical Formula 23] (Z)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime is a compound shown in the following formula.

[0085] [Chemical Formula 24] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-ethyl-1,2,4-thiadiazole is a compound shown in the following formula.

[0086] [Chemical Formula 25] 5-Cyclopropyl-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole is a compound represented by the following formula.

[0087] [Chemical Formula 26] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-(trifluoromethyl)-1,2,4-thiadiazole is a compound shown in the following formula.

[0088] [Chemical Formula 27] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxynitrile is a compound represented by the following formula.

[0089] [Chemical Formula 28] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole-5(4H)-one is a compound shown in the following formula.

[0090] [Chemical Formula 29] 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole is a compound represented by the following formula.

[0091] [Chemical Formula 30] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-ol is a compound shown in the following formula.

[0092] [Chemical Formula 31] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-methoxy-1,2,4-thiadiazole is a compound shown in the following formula.

[0093] [Chemical Formula 32] (2-chlorothiazol-4-yl)(3-fluoro-[1,1'-biphenyl]-4-yl)methanol is a compound shown in the following formula.

[0094] [Chemical Formula 33] 2-Chloro-4-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)thiazole is a compound represented by the following formula.

[0095] [Chemical Formula 34] 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole is a compound shown in the following formula.

[0096] [Chemical Formula 35] 5-Bromo-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole is a compound shown in the following formula.

[0097] [Chemical Formula 36] 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxamide is a compound shown in the following formula.

[0098] [Chemical Formula 37] The N oxide of the compound represented by formula (I) or formula (II) refers to the structure obtained by substituting at least one nitrogen atom in the compound represented by formula (I) or formula (II) with an oxo group.

[0099] This compound, the compound of this invention, intermediate A, or intermediate B sometimes contain more than one stereoisomer. Examples of stereoisomers include enantiomers, diastereomers, transisomers, and geometric isomers. This invention includes each stereoisomer and mixtures of stereoisomers in any ratio.

[0100] The compounds shown in formula (I) or formula (II) or their N oxides sometimes form acid addition salts such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid by mixing with acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.

[0101] In this compound, when q is 2, 3, 4, or 5, two adjacent R 6 and R 6 Compounds that, together with the carbon atoms they are bonded to, form C5-C6 alicyclic hydrocarbons, 5-6 membered nonaromatic heterocycles {where the C5-C6 alicyclic hydrocarbon and the 5-6 membered nonaromatic heterocycle can be substituted by one or more substituents selected from group B}, benzene rings, or 5-6 membered aromatic heterocycles {where the benzene ring and the 5-6 membered aromatic heterocycle can be substituted by one or more substituents selected from group C}, specifically, are the following compounds: 1) [Chemical Formula 38] In formula (IA), Ring A 5 R 3 R 4 R 5 D, m, and n represent the same meaning as in [1]. R 6A R 6B and R 6C The same or different from each other indicates R with [1].6 The same meaning or hydrogen atom, R 6D and R 6E Compounds that, together with the carbon atoms they are bonded to, form C5-C6 alicyclic hydrocarbons, 5-6 membered nonaromatic heterocycles {where the C5-C6 alicyclic hydrocarbon and the 5-6 membered nonaromatic heterocycle can be substituted by one or more substituents selected from group B}, benzene rings, or 5-6 membered aromatic heterocycles {where the benzene ring and the 5-6 membered aromatic heterocycle can be substituted by one or more substituents selected from group C}; or 2) In formula (IA), Ring A 5 R 3 R 4 R 5 D, m, and n represent the same meaning as in [1]. R 6A R 6B and R 6E The same or different from each other indicates R with [1]. 6 The same meaning or hydrogen atom, R 6C and R 6D Compounds that, together with the carbon atoms they are bonded to, form C5-C6 alicyclic hydrocarbons, 5-6 membered nonaromatic heterocycles {where the C5-C6 alicyclic hydrocarbon and the 5-6 membered nonaromatic heterocycle can be substituted by one or more substituents selected from group B}, benzene rings, or 5-6 membered aromatic heterocycles {where the benzene ring and the 5-6 membered aromatic heterocycle can be substituted by one or more substituents selected from group C}.

[0102] Examples of compounds that can be used as a means of producing compound A include the following compounds.

[0103] [Method A1] In this compound A, ring A 5 It is a 5-membered non-aromatic nitrogen-containing heterocyclic compound.

[0104] [Method A2] In this compound A, ring A 5 It is a 5-membered aromatic nitrogen-containing heterocyclic compound.

[0105] [Method A3] In this compound A, ring A 5 Compounds containing the group represented by formula H1.

[0106] [Method A4] In this compound A, ring A 5 Compounds containing the group represented by formula H2.

[0107] [Method A5] In this compound A, ring A 5 Compounds containing the group represented by formula H3.

[0108] [Method A6] In this compound A, ring A5 Compounds containing the group represented by formula H4.

[0109] [Method A7] In this compound A, ring A 5 Compounds that are groups represented by the formula H1, H2, H3 or H4.

[0110] [Method A8] In compound A, D is CR 1 R 2 Compounds.

[0111] [Method A9] In this compound A, D is a C=O compound.

[0112] [Method A10] In compound A, R 1 and R 2 They are either identical or different from each other, and are C1-C6 chain hydrocarbon groups or hydrogen atoms that can be substituted by one or more substituents selected from group A.

[0113] [Method A11] In this compound A, R 1 and R 2 They are either identical or different from each other, and are C1-C6 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms.

[0114] [Method A12] In compound A, R 1 and R 2 The same or different from each other is OR. 8 Compounds containing hydrogen atoms.

[0115] [Method A13] In compound A, R 1 and R 2 The same or different from each other is SR 9 S(O)R 10 S(O)2R 11 NR 12 R 13 Compounds containing hydrogen atoms.

[0116] [Method A14] In this compound A, R 1 and R 2 If they are the same or different from each other, it is called C(O)R. 14 C(R) 15 =NOR 16 Compounds containing cyano, nitro, or hydrogen atoms.

[0117] [Method A15] In compound A, R 1 and R 2 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0118] [Method A16] In compound A, R 1 and R 2 Compounds containing hydrogen atoms.

[0119] [Method A17] In compound A, R 1 and R 2 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8 Compounds containing halogen atoms or hydrogen atoms.

[0120] [Method A18] In this compound A, R 1 and R 2 The same or different from each other is OR. 8 Compounds containing halogen atoms or hydrogen atoms.

[0121] [Method A19] In this compound A, R 1 and R 2 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8 Compounds containing hydrogen atoms.

[0122] [Method A20] In this compound A, R 3 and R 5 They are either identical or different from each other, and are compounds of C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group A.

[0123] [Method A21] In this compound, R 3 and R 5 Compounds that are the same as or different from each other, and are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0124] [Method A22] In this compound A, R 3 and R 5 Compounds that are the same or different from each other, and are C3-C8 alicyclic hydrocarbon groups or 3-8 non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon group and the 3-8 non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}.

[0125] [Method A23] In compound A, R 3 and R 5 They are either identical or different from each other, and are compounds of 5-6 membered aromatic heterocyclic groups that can be substituted by one or more substituents selected from group C.

[0126] [Method A24] In compound A, R 3 and R 5 The same or different from each other is OR. 17 SR 18S(O)R 19 S(O)2R 20 NR 21 R 22 C(O)R 23 C(R) 24 =NOR 25 Compounds with cyano or nitro groups.

[0127] [Method A25] In compound A, R 3 and R 5 Compounds that are the same or different from each other and are composed of halogen atoms.

[0128] [Method A26] In compound A, R 3 and R 5 They are either identical or different from each other, and are compounds of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0129] [Method A27] In compound A, R 4 It is a compound of C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group A.

[0130] [Method A28] In this compound, R 4 Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0131] [Method A29] In compound A, R 4 Compounds that are C3-C8 alicyclic hydrocarbon groups or 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have one or more substituents selected from group B}.

[0132] [Method A30] In compound A, R 4 OR 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 Compounds with cyano or nitro groups.

[0133] [Method A31] In this compound A, R 4 Compounds containing halogen atoms.

[0134] [Method A32] In this compound A, R 4 Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0135] [Method A33] In this compound A, R 6It is a compound of C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group A.

[0136] [Method A34] In compound A, R 6 Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0137] [Method A35] In compound A, R 6 Compounds that are C3-C8 alicyclic hydrocarbon groups or 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have one or more substituents selected from group B}.

[0138] [Method A36] In compound A, R 6 Compounds that are phenyl or 5-6 membered aromatic heterocyclic groups {where the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}.

[0139] [Method A37] In compound A, R 6 OR 32 SR 33 S(O)R 34 S(O)2R 35 NR 36 R 37 C(O)R 38 C(R) 39 =NOR 40 Compounds with cyano or nitro groups.

[0140] [Method A38] In compound A, R 6 Compounds containing halogen atoms.

[0141] [Method A39] In this compound A, R 6 Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0142] [Method A40] In this compound A, two adjacent R 6 and R 6 Compounds formed together with the carbon atoms they are bonded to, forming C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles {the C5-C6 alicyclic hydrocarbons and the 5-6 membered non-aromatic heterocycles can be substituted by more than one halogen atom}.

[0143] [Method A41] In this compound A, two adjacent R 6 and R 6Compounds that, together with the carbon atoms they are bonded to, form a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may be substituted by more than one halogen atom}.

[0144] [Method A42] Compound A, in which n is 0.

[0145] [Method A43] In this compound A, n is 1.

[0146] [Method A44] Compound A, in which n is 2.

[0147] [Method A45] In this compound A, n is 3.

[0148] [Method A46] In this compound A, m is 0.

[0149] [Method A47] In this compound A, m is 1.

[0150] [Method A48] In this compound A, m is 2.

[0151] [Method A49] In this compound A, m is 3.

[0152] [Method A50] In this compound A, m is 0 or 1.

[0153] [Method A51] In this compound A, the compound in which q is 0.

[0154] [Method A52] In this compound A, the compound in which q is 1.

[0155] [Method A53] In this compound A, the compound in which q is 2.

[0156] [Method A54] In this compound A, the compound in which q is 3.

[0157] [Method A55] In this compound A, the compound in which q is 4.

[0158] [Method A56] In this compound A, the compound in which q is 5.

[0159] [Method A57] In this compound A, ring A 5 It is a group represented by formula H1, H2, H3 or H4, where D is CR 1 R 2 R 1 and R 2 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8 halogen atoms or hydrogen atoms, R 3 and R 5The same or different from each other, is a C1-C6 chain hydrocarbon group or halogen atom that can be replaced by one or more halogen atoms, R 4 R is a C1-C6 chain hydrocarbon group or halogen atom that can be replaced by one or more halogen atoms. 6 Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0160] [Method A58] In this compound A, R 1 and R 2 Compounds that, together with the carbon atoms they are bonded to, form C3-C8 alicyclic hydrocarbons or 3-8 membered nonaromatic heterocycles {the C3-C8 alicyclic hydrocarbons and the 3-8 membered nonaromatic heterocycles may be substituted by one or more substituents selected from group B}.

[0161] [Method A59] In this compound A, ring A 5 Compounds that are groups represented by formula H1 or H2.

[0162] [Method A60] In this compound A, ring A 5 Compounds that are groups represented by formula H1 or H3.

[0163] [Method A61] In this compound A, ring A 5 Compounds that are groups represented by formula H1 or H4.

[0164] [Method A62] In this compound A, ring A 5 Compounds that are groups represented by the formula H2 or H3.

[0165] [Method A63] In this compound A, ring A 5 Compounds that are groups represented by the formula H2 or H4.

[0166] [Method A64] In this compound A, ring A 5 Compounds that are groups represented by formula H3 or H4.

[0167] [Method A65] In this compound A, ring A 5 Compounds of the formula H1, H2, H3 or H4, or of the tetrazol-1-yl or tetrazol-2-yl group.

[0168] Other compounds that can be cited as examples of compound A include the following compounds.

[0169] [Method AX1] In this compound A, ring A 5 Compounds having groups represented by formulas H1-1, H1-2, H1-3, H1-4, H1-5, H1-6, H2-1, H2-2, H3-1, H3-2, H4-1, or H4-2.

[0170] [Chemical Formula 39] [Chemical Formula 40] [Chemical Formula 41] [In the formula, the symbols have the same meaning as in the preceding text.] [Method AX2] In this compound A, ring A 5 The group represented by formula H1-1, H1-2, H1-3, H1-4, H1-5, H1-6, H2-1, H2-2, H3-1, H3-2, H4-1, or H4-2 R a4 R b4 R c4 R e4 R f4 R h4 R i4 and R j4 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 26 halogen atoms or hydrogen atoms R d1 It is a C1-C6 chain hydrocarbon group that can be replaced by one or more halogen atoms. D is CR 1 R 2 Or C=O, R 1 and R 2 They may be the same or different from each other, consisting of halogen atoms, hydroxyl groups, or hydrogen atoms. R 3 and R 5 They may be identical or different from each other, and are C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, and can be selected from group A. X 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17 or halogen atoms, R 6 It is a C1-C6 chain hydrocarbon group or a halogen atom that can be replaced by one or more halogen atoms. R 17 and R 26 They are either identical or different from each other, and are C1-C6 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms.

[0171] Group A XThe group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 haloalkyl groups, C1-C4 alkoxy groups, and C1-C4 haloalkoxy groups.

[0172] [Method AX3] In this compound A, ring A 5 The group represented by formula H1-1, H1-2, H1-3, H1-4, H1-5, H1-6, H2-1, H2-2, H3-1, H3-2, H4-1, or H4-2 R a4 R b4 R c4 R e4 R f4 R h4 R i4 and R j4 They may be the same as or different from each other, and are C1-C6 chain hydrocarbon groups, C1-C4 alkoxy groups, halogen atoms, or hydrogen atoms that can be substituted by one or more halogen atoms. R d1 It is a C1-C6 chain hydrocarbon group. D is CR 1 R 2 Or C=O, R 1 and R 2 They may be the same or different from each other, consisting of halogen atoms, hydroxyl groups, or hydrogen atoms. R 3 and R 5 They may be the same or different from each other, consisting of C1-C6 chain hydrocarbon groups, 5-6 membered aromatic heterocyclic groups, C1-C4 alkoxy groups, or halogen atoms. R 6 Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms.

[0173] [Method AX4] In any of Method AX2, Method AX3, or Compound A, ring A 5 Compounds of the groups represented by formula H1-1, H1-2, H1-3, H1-4, H1-5, H1-6, H2-1, H2-2, H3-1, H4-1 or H4-2.

[0174] [Method AX5] In any of Method AX2, Method AX3, or Compound A, ring A 5 Compounds having groups represented by formulas H1-1, H1-2, H1-3, H1-5, H1-6, H2-1, H2-2, H3-1, H4-1, or H4-2.

[0175] [Method AX5] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A5 Compounds containing the group represented by formula H1-1.

[0176] [Method AX6] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds containing the groups shown in formula H1-2.

[0177] [Method AX7] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H1-3.

[0178] [Method AX8] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H1-4.

[0179] [Method AX9] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H1-5.

[0180] [Method AX10] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H1-6.

[0181] [Method AX11] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H2-1.

[0182] [Method AX12] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds containing the group represented by formula H2-2.

[0183] [Method AX13] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds containing the group represented by formula H3-1.

[0184] [Method AX14] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds containing the group represented by formula H3-2.

[0185] [Method AX15] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A 5 Compounds with groups represented by formula H4-1.

[0186] [Method AX16] In any of Method AX2, Method AX3, or Compound A of the present invention, ring A5 Compounds containing the group shown in formula H4-2.

[0187] Examples of compounds that can be used as compound A in this invention include the following compounds.

[0188] [Method B1] In compound A of the present invention, ring A 5a It is a 5-membered aromatic nitrogen-containing heterocyclic compound.

[0189] [Method B2] In compound A of the present invention, ring A 5a Compounds with groups represented by formula H1a.

[0190] [Method B3] In compound A of the present invention, ring A 5a Compounds with the group represented by formula H2a.

[0191] [Method B4] In compound A of the present invention, ring A 5a Compounds containing the group represented by formula H3a.

[0192] [Method B5] In compound A of the present invention, ring A 5a Compounds containing the group represented by formula H4a.

[0193] [Method B6] In compound A of the present invention, ring A 5a Compounds that are groups represented by the formula H1a, H2a, H3a or H4a.

[0194] [Method B7] In compound A of the present invention, R 1a and R 2a If they are the same or different from each other, they can be selected from group A. a Compounds in which one or more substituents are substituted C1-C6 chain hydrocarbon groups or hydrogen atoms.

[0195] [Method B8] In compound A of the present invention, R 1a and R 2a They are either identical or different from each other, and are C1-C6 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms.

[0196] [Method B9] In compound A of the present invention, R 1a and R 2a The same or different from each other is OR. 8a Compounds containing hydrogen atoms.

[0197] [Method B10] In compound A of the present invention, R 1a and R 2a The same or different from each other is SR 9a S(O)R 10a S(O)2R 11a NR12a R 13a Compounds containing hydrogen atoms.

[0198] [Method B11] In compound A of the present invention, R 1a and R 2a If they are the same or different from each other, it is called C(O)R. 14a C(R) 15a =NOR 16a Compounds containing cyano, nitro, or hydrogen atoms.

[0199] [Method B12] In compound A of the present invention, R 1a and R 2a Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0200] [Method B13] In compound A of the present invention, R 1a and R 2a Compounds containing hydrogen atoms.

[0201] [Method B14] In compound A of the present invention, R 1a and R 2a The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8a Compounds containing halogen atoms or hydrogen atoms.

[0202] [Method B15] In compound A of the present invention, R 1a and R 2a The same or different from each other is OR. 8a Compounds containing halogen atoms or hydrogen atoms.

[0203] [Method B16] In compound A of the present invention, R 1a and R 2a The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8a Compounds containing hydrogen atoms.

[0204] [Method B17] In compound A of the present invention, R 3a and R 5a If they are the same or different from each other, they can be selected from group A. a Compounds in which one or more substituents are substituted C1-C6 chain hydrocarbon groups.

[0205] [Method B18] In compound A of the present invention, R 3a and R 5a Compounds that are the same as or different from each other, and are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0206] [Method B19] In compound A of the present invention, R3a and R 5a They may be identical or different from each other, being C3-C8 alicyclic hydrocarbon groups or 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Compounds in which one or more substituents are substituted.

[0207] [Method B20] In compound A of the present invention, R 3a and R 5a If they are the same or different from each other, they can be selected from group C. a Compounds of 5-6 membered aromatic heterocyclic groups substituted with one or more substituents.

[0208] [Method B21] In compound A of the present invention, R 3a and R 5a The same or different from each other is OR. 17a SR 18a S(O)R 19a S(O)2R 20a NR 21a R 22a C(O)R 23a C(R) 24a =NOR 25a Compounds with cyano or nitro groups.

[0209] [Method B22] In compound A of the present invention, R 3a and R 5a Compounds that are the same or different from each other and are composed of halogen atoms.

[0210] [Method B23] In compound A of the present invention, R 3a and R 5a They are either identical or different from each other, and are compounds of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0211] [Method B24] In compound A of the present invention, R 4a For can be selected from group D a Compounds in which one or more substituents are substituted C1-C6 chain hydrocarbon groups.

[0212] [Method B25] In compound A of the present invention, R 4a Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0213] [Method B26] In compound A of the present invention, R 4a It is a C3-C8 alicyclic hydrocarbon group or a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have components selected from group B} aCompounds with one or more substituents.

[0214] [Method B27] In compound A of the present invention, R 4a OR 26a NR 27a R 28a C(O)R 29a C(R) 30a =NOR 31a Compounds with cyano or nitro groups.

[0215] [Method B28] In compound A of the present invention, R 4a Compounds containing halogen atoms.

[0216] [Method B29] In compound A of the present invention, R 4a Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0217] [Method B30] In compound A of the present invention, R 6a For can be selected from group E a Compounds in which one or more substituents are substituted C1-C6 chain hydrocarbon groups.

[0218] [Method B31] In compound A of the present invention, R 6a Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0219] [Method B32] In compound A of the present invention, R 6a For can be selected from group B a Compounds in which one or more substituents are substituted C3-C8 alicyclic hydrocarbon groups.

[0220] [Method B33] In compound A of the present invention, R 6a It is a phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group C} a Compounds in which one or more substituents are substituted.

[0221] [Method B34] In compound A of the present invention, R 6a OR 31a SR 32a S(O)R 33a S(O)2R 34a NR 35a R 36a C(O)R 37a C(R) 38a =NOR 39a Compounds with cyano or nitro groups.

[0222] [Method B35] In compound A of the present invention, R 6a Compounds containing halogen atoms.

[0223] [Method B36] In compound A of the present invention, R 6a Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms that can be replaced by one or more halogen atoms.

[0224] [Method B37] Compound A of the present invention, wherein na is 0.

[0225] [Method B38] Compound A of the present invention, wherein na is 1.

[0226] [Method B39] Compound A of the present invention, wherein na is 2.

[0227] [Method B40] Compound A of the present invention, wherein na is 3.

[0228] [Method B41] Compound A of the present invention, wherein ma is 0.

[0229] [Method B42] Compound A of the present invention, wherein ma is 1.

[0230] [Method B43] Compound A of the present invention, wherein ma is 2.

[0231] [Method B44] Compound A of the present invention, wherein ma is 3.

[0232] [Method B45] Compound A of the present invention, wherein ma is 0 or 1.

[0233] [Method B46] The compound A of the present invention in which qa is 0.

[0234] [Method B47] Compound A of the present invention, wherein qa is 1.

[0235] [Method B48] Compound A of the present invention, wherein qa is 2.

[0236] [Method B49] Compound A of the present invention, wherein qa is 3.

[0237] [Method B50] Compound A of the present invention, wherein qa is 4.

[0238] [Method B51] Compound A of the present invention, wherein qa is 5.

[0239] [Method B52] In compound A of the present invention, R 1a and R 2aTogether with the carbon atoms they are bonded to, they form C3-C8 alicyclic hydrocarbons or 3-8 membered non-aromatic heterocycles {the C3-C8 alicyclic hydrocarbons and the 3-8 membered non-aromatic heterocycles can be selected from group B} a Compounds in which one or more substituents are substituted.

[0240] [Method B53] In compound A of the present invention, ring A 5a Compounds that are groups represented by formula H1a or H2a.

[0241] [Method B54] In compound A of the present invention, ring A 5a Compounds that are groups represented by formula H1a or H3a.

[0242] [Method B55] In compound A of the present invention, ring A 5a Compounds that are groups represented by the formula H1a or H4a.

[0243] [Method B56] In compound A of the present invention, ring A 5a Compounds that are groups represented by the formula H2a or H3a.

[0244] [Method B57] In compound A of the present invention, ring A 5a Compounds with groups represented by the formula H2a or H4a.

[0245] [Method B58] In compound A of the present invention, ring A 5a Compounds that are groups represented by the formula H3a or H4a.

[0246] [Method B59] In compound A of the present invention, ring A 5a Compounds of the formula H1a, H2a, H3a or H4a, or of the tetrazol-1-yl or tetrazol-2-yl group.

[0247] In addition, the following compounds can also be cited as examples of compound A of the present invention.

[0248] [Method BB1] The compound shown in formula (II-1A), [Chemical Formula 42] In the formula, Q 5A The group represented by formula H1a, H2a, H3a or H4a R 1B and R 2B Same or different from each other, indicating C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 8a SR 9a S(O)R 10a S(O)2R11a NR 12a R 13a C(O)R 14a C(R) 15a =NOR 16a cyano, nitro, halogen or hydrogen atom R C2 This indicates that it can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17a SR 18a S(O)R 19a S(O)2R 20a NR 21a R 22a C(O)R 23a C(R) 24a =NOR 25a cyano, nitro, or halogen atoms R C3 R C4 and R C5 The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17a SR 18a S(O)R 19a S(O)2R 20a NR 21a R 22a C(O)R 23a C(R) 24a =NOR 25a cyano, nitro, halogen or hydrogen atom R D2 R D3 R D4 R D5 and R D6 The same or different from each other indicates that they can be selected from group E. aA C1-C6 chain hydrocarbon group substituted with one or more substituents, which may have a group selected from group B a The C3-C8 alicyclic hydrocarbon group, phenyl group, or 5-6 membered aromatic heterocyclic group with one or more substituents {the phenyl group and the 5-6 membered aromatic heterocyclic group can be selected from group C} a Substitution of one or more substituents in OR 31a SR 32a S(O)R 33a S(O)2R 34a NR 35a R 36a C(O)R 37a C(R) 38a =NOR 39a cyano, nitro, halogen or hydrogen atom Other symbols have the same meaning as [7] and [8].

[0249] [Method BB2] In Method BB1, R D2 R D3 R D4 R D5 and R D6 The same or different from each other are C1-C4 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 31a SR 32a S(O)R 33a S(O)2R 34a , cyano, halogen atom or hydrogen atom, R 32a R 33a R 34a and R 35a They are either identical or different from each other, and are C1-C4 alkyl compounds that can be substituted with one or more halogen atoms.

[0250] [Method BB3] In Method BB1, R D2 R D3 R D4 R D5 and R D6 They are the same or different from each other, and are compounds of C1-C4 chain hydrocarbon groups that can be replaced by one or more halogen atoms, C1-C4 alkoxy groups that can be replaced by one or more halogen atoms, halogen atoms or hydrogen atoms.

[0251] [Method BB4] In Method BB1, R D2 R D3 R D4 R D5 and R D6 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0252] [Method BB5] In Method BB1, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 They may be the same or different from each other, and are either halogen atoms or hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0253] [Method BB6] In Method BB2, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 They may be the same or different from each other, and are either halogen atoms or hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0254] [Method BB7] In Method BB3, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 They may be the same or different from each other, and are either halogen atoms or hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0255] [Method BB8] In Method BB4, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 They may be the same or different from each other, and are either halogen atoms or hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0256] [Method BB9] In Method BB1, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 RC4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0257] In method BB10, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0258] [Method BB11] In Method BB3, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0259] In method BB12, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0260] [Method BB13] In Method BB1, R C2 For halogen atoms, R C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0261] [Method BB14] In Method BB2, R C2 For halogen atoms, R C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0262] [Method BB15] In Method BB3, R C2 For halogen atoms, R C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0263] [Method BB16] In Method BB4, R C2For halogen atoms, R C3 R C4 and R C5 Compounds that are the same or different from each other, consisting of halogen atoms or hydrogen atoms.

[0264] [Method BB17] In Method BB1, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 For hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0265] In method BB18, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 For hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0266] [Method BB19] In Method BB3, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 For hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0267] [Method BB20] In Method BB4, R C2 R is a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom. C3 and R C4 For hydrogen atoms, R C5 It is a compound consisting of a C1-C4 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C1-C4 alkoxy group that can be replaced by one or more halogen atoms, a halogen atom, or a hydrogen atom.

[0268] [Method BB21] In Method BB1, R C2 For halogen atoms, R C3and R C4 For hydrogen atoms, R C5 Compounds consisting of halogen atoms or hydrogen atoms.

[0269] [Method BB22] In Method BB2, R C2 For halogen atoms, R C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of halogen atoms or hydrogen atoms.

[0270] [Method BB23] In Method BB3, R C2 For halogen atoms, R C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of halogen atoms or hydrogen atoms.

[0271] [Method BB24] In Method BB4, R C2 For halogen atoms, R C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of halogen atoms or hydrogen atoms.

[0272] [Method BB25] In Method BB1, R C2 and R C5 The same or different from each other, being a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom, R C3 and R C4 Compounds containing hydrogen atoms.

[0273] [Method BB26] In Method BB2, R C2 and R C5 The same or different from each other, being a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom, R C3 and R C4 Compounds containing hydrogen atoms.

[0274] [Method BB27] In Method BB3, R C2 and R C5 The same or different from each other, being a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom, R C3 and R C4 Compounds containing hydrogen atoms.

[0275] [Method BB28] In Method BB4, R C2 and R C5The same or different from each other, being a C1-C4 chain hydrocarbon group that can be substituted by one or more halogen atoms, a C1-C4 alkoxy group that can be substituted by one or more halogen atoms, or a halogen atom, R C3 and R C4 Compounds containing hydrogen atoms.

[0276] [Method BB29] In Method BB1, R C2 and R C5 For halogen atoms, R C3 and R C4 Compounds containing hydrogen atoms.

[0277] [Method BB30] In Method BB2, R C2 and R C5 For halogen atoms, R C3 and R C4 Compounds containing hydrogen atoms.

[0278] [Method BB31] In Method BB3, R C2 and R C5 For halogen atoms, R C3 and R C4 Compounds containing hydrogen atoms.

[0279] In method BB32, R C2 and R C5 For halogen atoms, R C3 and R C4 Compounds containing hydrogen atoms.

[0280] [Method BB33] In Method BB1, R C2 R is a fluorine atom. C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of fluorine or hydrogen atoms.

[0281] [Method BB34] In Method BB2, R C2 R is a fluorine atom. C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of fluorine or hydrogen atoms.

[0282] [Method BB35] In Method BB3, R C2 R is a fluorine atom. C3 and R C4 For hydrogen atoms, R C5 Compounds consisting of fluorine or hydrogen atoms.

[0283] In method BB36, R C2 R is a fluorine atom. C3 and RC4 For hydrogen atoms, R C5 Compounds consisting of fluorine or hydrogen atoms.

[0284] [Method BB37] In Method BB1, R C2 and R C5 R is a fluorine atom. C3 and R C4 Compounds containing hydrogen atoms.

[0285] [Method BB38] In Method BB2, R C2 and R C5 R is a fluorine atom. C3 and R C4 Compounds containing hydrogen atoms.

[0286] [Method BB39] In Method BB3, R C2 and R C5 R is a fluorine atom. C3 and R C4 Compounds containing hydrogen atoms.

[0287] [Method BB40] In Method BB4, R C2 and R C5 R is a fluorine atom. C3 and R C4 Compounds containing hydrogen atoms.

[0288] [Method BB41] In any of methods BB1 to BB40, R 1B and R 2B The same or different from each other is OR. 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0289] [Method BB42] In any of methods BB1 to BB40, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0290] [Method BB43] In any of methods BB1 to BB40, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0291] [Method BB44] In any of methods BB1 to BB40, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0292] [Method BB45] In any of methods BB1 to BB40, R 1B and R 2B Compounds containing hydrogen atoms.

[0293] [Method BB46] In any of methods BB1 to BB40, Q 5A Compounds having groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8.

[0294] The groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8 are each represented by the group shown in the following formula.

[0295] [Chemical Formula 43] [Chemical Formula 44] [In the formula, #] A Indicates CR 1B R 2B The bonding site, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 R Q62 R Q71 R Q72 R Q81 and R Q82 The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in OR 26a NR 27a R 28a C(R) 29a=NOR 30a [Cyano, nitro, halogen, or hydrogen atom.] [Method BB47] In any of methods BB1 to BB40, Q 5A Compounds having a group represented by formula HQ1, HQ2, HQ3, HQ4, HQ5 or HQ6.

[0296] [Method BB48] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0297] [Method BB49] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 They are either identical or different from each other, and are C1-C4 alkyl or hydrogen atoms that can be substituted by one or more halogen atoms.

[0298] [Method BB50] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 RQ21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 Compounds containing hydrogen atoms.

[0299] [Method BB51] In any of methods BB1 to BB40, Q 5A Compounds that have groups represented by formula HQ1, HQ2, HQ3 or HQ4.

[0300] [Method BB52] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0301] [Method BB53] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0302] [Method BB54] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 RQ31 R Q32 R Q41 and R Q42 Compounds containing hydrogen atoms.

[0303] [Method BB55] In any of the methods BB1 to BB40, Q 5A Compounds with groups represented by formula HQ1.

[0304] [Method BB56] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0305] [Method BB57] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0306] [Method BB58] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 Compounds containing hydrogen atoms.

[0307] [Method BB59] In any of methods BB1 to BB40, Q 5A Compounds having a group represented by the formula HQ2, HQ3 or HQ4.

[0308] [Method BB60] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0309] [Method BB61] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0310] [Method BB62] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Compounds containing hydrogen atoms.

[0311] [Method BB63] In any of methods BB1 to BB40, Q 5A Compounds with the group represented by formula HQ2.

[0312] [Method BB64] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0313] [Method BB65] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0314] [Method BB66] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2.Q21 and R Q22 Compounds containing hydrogen atoms.

[0315] [Method BB67] In any of methods BB1 to BB40, Q 5A Compounds with the group represented by formula HQ3.

[0316] [Method BB68] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0317] [Method BB69] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0318] [Method BB70] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 Compounds containing hydrogen atoms.

[0319] [Method BB71] In any of methods BB1 to BB40, Q 5A Compounds with the group represented by formula HQ4.

[0320] [Method BB72] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0321] [Method BB73] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0322] [Method BB74] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 Compounds containing hydrogen atoms.

[0323] [Method BB75] In any of the methods BB1 to BB40, Q 5A Compounds having groups represented by formula HQ5 or HQ6.

[0324] [Method BB76] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0325] [Method BB77] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0326] [Method BB78] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 Compounds containing hydrogen atoms.

[0327] [Method BB79] In any of methods BB1 to BB40, Q 5A Compounds with groups represented by formula HQ5.

[0328] [Method BB80] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0329] [Method BB81] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0330] [Method BB82] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 Compounds containing hydrogen atoms.

[0331] [Method BB83] In any of methods BB1 to BB40, Q 5A Compounds with the group represented by formula HQ6.

[0332] [Method BB84] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 They are the same or different from each other, and are C1-C4 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C4 alkoxy groups, cyano groups, halogen atoms or hydrogen atoms that can be substituted with one or more halogen atoms.

[0333] [Method BB85] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 They are either identical or different from each other, and are C1-C4 alkyl, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0334] [Method BB86] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 Compounds containing hydrogen atoms.

[0335] [Method BB87] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8, R1B and R 2B The same or different from each other is OR. 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0336] [Method BB88] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0337] [Method BB89] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0338] [Method BB90] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62Identical or different from each other, R is a C1-C4 alkyl or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0339] [Method BB91] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0340] [Method BB92] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0341] [Method BB93] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0342] [Method BB94] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0343] [Method BB95] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0344] [Method BB96] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0345] [Method BB97] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0346] [Method BB98] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0347] [Method BB99] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0348] [Method BB100] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0349] [Method BB101] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0350] [Method BB102] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 RQ41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0351] [Method BB103] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0352] [Method BB104] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0353] [Method BB105] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0354] [Method BB106] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0355] [Method BB107] In any of methods BB1 to BB40, Q5A R is the group represented by formula HQ2. Q21 and R Q22 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0356] [Method BB108] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0357] [Method BB109] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0358] [Method BB110] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0359] [Method BB111] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0360] [Method BB112] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0361] [Method BB113] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0362] [Method BB114] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0363] [Method BB115] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0364] [Method BB116] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0365] [Method BB117] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8aIt is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0366] [Method BB118] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0367] [Method BB119] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0368] [Method BB120] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0369] [Method BB121] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0370] [Method BB122] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0371] [Method BB123] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 For hydrogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0372] [Method BB124] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0373] [Method BB125] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0374] [Method BB126] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0375] [Method BB127] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 For hydrogen atoms, R 8aIt is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0376] [Method BB128] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0377] [Method BB129] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0378] [Method BB130] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0379] [Method BB131] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0380] [Method BB132] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0381] [Method BB133] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8aIt is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0382] [Method BB134] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0383] [Method BB135] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0384] [Method BB136] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 RQ22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0385] [Method BB137] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0386] [Method BB138] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0387] [Method BB139] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0388] [Method BB140] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0389] [Method BB141] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0390] [Method BB142] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0391] [Method BB143] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms.1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0392] [Method BB144] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0393] [Method BB145] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0394] [Method BB146] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0395] [Method BB147] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0396] [Method BB148] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0397] [Method BB149] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0398] [Method BB150] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0399] [Method BB151] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0400] [Method BB152] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0401] [Method BB153] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0402] [Method BB154] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0403] [Method BB155] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0404] [Method BB156] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0405] [Method BB157] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0406] [Method BB158] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0407] [Method BB159] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 RQ52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0408] [Method BB160] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0409] [Method BB161] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0410] [Method BB162] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0411] [Method BB163] In any of methods BB1 to BB40, Q5A R is the group represented by formula HQ5. Q51 and R Q52 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0412] [Method BB164] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0413] [Method BB165] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0414] [Method BB166] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0415] [Method BB167] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6.Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0416] [Method BB168] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a It is a compound that can be replaced by one or more halogen atoms, namely a C1-C4 alkyl group, a (C1-C4 alkyl) carbonyl group, or a hydrogen atom.

[0417] [Method BB169] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0418] [Method BB170] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0419] [Method BB171] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42R Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0420] [Method BB172] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0421] [Method BB173] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8aCompounds containing hydrogen atoms.

[0422] [Method BB174] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0423] [Method BB175] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0424] [Method BB176] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0425] [Method BB177] In any of methods BB1 to BB40, Q 5AFor groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0426] [Method BB178] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0427] [Method BB179] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0428] [Method BB180] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0429] [Method BB181] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1.Q11 R Q12 and R Q13 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0430] [Method BB182] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0431] [Method BB183] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0432] [Method BB184] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0433] [Method BB185] In any of methods BB1 to BB40, Q 5AFor groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0434] [Method BB186] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0435] [Method BB187] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0436] [Method BB188] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0437] [Method BB189] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8aOr hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0438] [Method BB190] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0439] [Method BB191] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0440] [Method BB192] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0441] [Method BB193] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0442] [Method BB194] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R8a Compounds containing hydrogen atoms.

[0443] [Method BB195] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0444] [Method BB196] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0445] [Method BB197] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0446] [Method BB198] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0447] [Method BB199] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0448] [Method BB200] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0449] [Method BB201] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0450] [Method BB202] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0451] [Method BB203] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1BFor hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0452] [Method BB204] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0453] [Method BB205] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0454] [Method BB206] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0455] [Method BB207] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0456] [Method BB208] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0457] [Method BB209] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a Or hydrogen atom, R 8a Compounds containing hydrogen atoms.

[0458] [Method BB210] In any of methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0459] [Method BB211] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0460] [Method BB212] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0461] [Method BB213] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0462] [Method BB214] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0463] [Method BB215] In any of the methods BB1 to BB40, Q 5AFor groups represented by formula HQ1, HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0464] [Method BB216] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0465] [Method BB217] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0466] [Method BB218] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0467] [Method BB219] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0468] [Method BB220] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0469] [Method BB221] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0470] [Method BB222] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0471] [Method BB223] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0472] [Method BB224] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0473] [Method BB225] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0474] [Method BB226] In any of methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R8a Compounds containing hydrogen atoms.

[0475] [Method BB227] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0476] [Method BB228] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0477] [Method BB229] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0478] [Method BB230] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0479] [Method BB231] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0480] [Method BB232] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0481] [Method BB233] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0482] [Method BB234] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0483] [Method BB235] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0484] [Method BB236] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0485] [Method BB237] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0486] [Method BB238] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0487] [Method BB239] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0488] [Method BB240] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0489] [Method BB241] In any of the methods BB1 to BB40, Q 5AR is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0490] [Method BB242] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0491] [Method BB243] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0492] [Method BB244] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0493] [Method BB245] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2BOR 8a R 8a Compounds containing hydrogen atoms.

[0494] [Method BB246] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 For hydrogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0495] [Method BB247] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0496] [Method BB248] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0497] [Method BB249] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B For hydrogen atoms, R 2B OR 8a R 8a Compounds containing hydrogen atoms.

[0498] [Method BB250] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 For hydrogen atoms, R 1B For hydrogen atoms, R 2BOR 8a R 8a Compounds containing hydrogen atoms.

[0499] [Method BB251] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, HQ6, HQ7, or HQ8, R 1B and R 2B Compounds containing hydrogen atoms.

[0500] [Method BB252] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R 1B and R 2B Compounds containing hydrogen atoms.

[0501] [Method BB253] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0502] [Method BB254] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0503] [Method BB255] In any of the methods BB1 to BB40, Q 5A For groups represented by formulas HQ1, HQ2, HQ3, HQ4, HQ5, or HQ6, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 R Q42 R Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0504] [Method BB256] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R 1B and R 2B Compounds containing hydrogen atoms.

[0505] [Method BB257] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0506] [Method BB258] In any of the methods BB1 to BB40, Q 5AFor groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0507] [Method BB259] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ1, HQ2, HQ3 or HQ4, R Q11 R Q12 R Q13 R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0508] [Method BB260] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. 1B and R 2B Compounds containing hydrogen atoms.

[0509] [Method BB261] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0510] [Method BB262] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0511] [Method BB263] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ1. Q11 R Q12 and R Q13 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0512] [Method BB264] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R 1B and R 2B Compounds containing hydrogen atoms.

[0513] [Method BB265] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0514] [Method BB266] In any of the methods BB1 to BB40, Q 5A For groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0515] [Method BB267] In any of methods BB1 to BB40, Q 5AFor groups represented by formula HQ2, HQ3 or HQ4, R Q21 R Q22 R Q31 R Q32 R Q41 and R Q42 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0516] [Method BB268] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. 1B and R 2B Compounds containing hydrogen atoms.

[0517] [Method BB269] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0518] [Method BB270] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0519] [Method BB271] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ2. Q21 and R Q22 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0520] [Method BB272] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. 1B and R 2B Compounds containing hydrogen atoms.

[0521] [Method BB273] In any of the methods BB1 to BB40, Q5A R is the group represented by formula HQ3. Q31 and R Q32 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0522] [Method BB274] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0523] [Method BB275] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ3. Q31 and R Q32 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0524] [Method BB276] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. 1B and R 2B Compounds containing hydrogen atoms.

[0525] [Method BB277] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0526] [Method BB278] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms.1B and R 2B Compounds containing hydrogen atoms.

[0527] [Method BB279] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ4. Q41 and R Q42 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0528] [Method BB280] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. 1B and R 2B Compounds containing hydrogen atoms.

[0529] [Method BB281] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0530] [Method BB282] In any of methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0531] [Method BB283] In any of the methods BB1 to BB40, Q 5A R is a group represented by formula HQ5 or formula HQ6. Q51 R Q52 R Q61 and R Q62 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0532] [Method BB284] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. 1B and R 2B Compounds containing hydrogen atoms.

[0533] [Method BB285] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0534] [Method BB286] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0535] [Method BB287] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ5. Q51 and R Q52 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0536] [Method BB288] In any of the methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. 1B and R 2B Compounds containing hydrogen atoms.

[0537] [Method BB289] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 The same or different from each other, being a C1-C4 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C4 alkoxy group, a cyano group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0538] [Method BB290] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 Identical or different from each other, R is a C1-C4 alkyl group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms. 1B and R 2B Compounds containing hydrogen atoms.

[0539] [Method BB291] In any of methods BB1 to BB40, Q 5A R is the group represented by formula HQ6. Q61 and R Q62 For hydrogen atoms, R 1B and R 2B Compounds containing hydrogen atoms.

[0540] In addition, the following compounds can also be cited as examples of compound A of the present invention.

[0541] [Method BX1] In compound A of the present invention, ring A 5a Compounds of the formula H1a-1, H1a-2, H1a-3, H1a-4, H1a-5, H1a-6, H2a-1, H2a-2, H3a-1, H3a-2, H4a-1 or H4a-2.

[0542] [Chemical Formula 45] [Chemical Formula 46] [Chemical Formula 47] [In the formula, the symbols have the same meaning as in the preceding text.] [Method BX2] In compound A of the present invention, ring A 5a The group represented by formula H1a-1, H1a-2, H1a-3, H1a-4, H1a-5, H1a-6, H2a-1, H2a-2, H3a-1, H3a-2, H4a-1, or H4a-2. R a4a R b4a R c4a R e4a R f4a R h4a R i4a and R j4aThe same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 26a halogen atoms or hydrogen atoms R d1a It is a C1-C6 chain hydrocarbon group that can be replaced by one or more halogen atoms. R 1a and R 2a They may be the same or different from each other, consisting of halogen atoms, hydroxyl groups, or hydrogen atoms. R 3a and R 5a They may be identical or different from each other, and are C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, and can be selected from group A. Xa 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17a or halogen atoms, R 6a It is a C1-C6 chain hydrocarbon group or a halogen atom that can be replaced by one or more halogen atoms. R 17a and R 26a They are either identical or different from each other, and are C1-C6 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms.

[0543] Group A Xa The group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 haloalkyl groups, C1-C4 alkoxy groups, and C1-C4 haloalkoxy groups.

[0544] [Method BX3] In compound A of the present invention, ring A 5a The group represented by formula H1a-1, H1a-2, H1a-3, H1a-4, H1a-5, H1a-6, H2a-1, H2a-2, H3a-1, H3a-2, H4a-1, or H4a-2. R a4a R b4a R c4a R e4a R f4a R h4a R i4a and R j4a They may be the same as or different from each other, and are C1-C6 chain hydrocarbon groups, C1-C4 alkoxy groups, halogen atoms, or hydrogen atoms that can be substituted by one or more halogen atoms. R d1a It is a C1-C6 chain hydrocarbon group that can be replaced by one or more halogen atoms. R 1a and R 2a They may be the same or different from each other, consisting of halogen atoms, hydroxyl groups, or hydrogen atoms. R3a and R 5a They may be the same as or different from each other, and are C1-C6 chain hydrocarbon groups, 5-6 membered aromatic heterocyclic groups, C1-C4 alkoxy groups, or halogen atoms that can be substituted by one or more halogen atoms. R 6a Compounds consisting of C1-C6 chain hydrocarbon groups or halogen atoms.

[0545] [Method BX4] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds of the formula H1a-1, H1a-2, H1a-3, H1a-4, H1a-5, H1a-6, H2a-1, H2a-2, H3a-1, H4a-1 or H4a-2.

[0546] [Method BX5] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-1.

[0547] [Method BX6] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-2.

[0548] [Method BX7] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-3.

[0549] [Method BX8] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-4.

[0550] [Method BX9] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-5.

[0551] [Method BX10] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H1a-6.

[0552] [Method BX11] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H2a-1.

[0553] [Method BX12] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A5a Compounds containing the group represented by formula H2a-2.

[0554] [Method BX13] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H3a-1.

[0555] [Method BX14] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H3a-2.

[0556] [Method BX15] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H4a-1.

[0557] [Method BX16] In any of Method BX2, Method BX3, or Compound A of the present invention, ring A 5a Compounds containing the group represented by formula H4a-2.

[0558] [Method C1] A method for controlling soybean rust fungus, which is carried out by treating soybeans or the soil in which soybeans are cultivated with this compound.

[0559] [Method C2] A method for controlling soybean rust fungus, which is carried out by treating soybeans or the soil in which soybeans are cultivated with the compound of the present invention.

[0560] Next, the method for manufacturing this compound (including the compound of the present invention) will be described.

[0561] Manufacturing Method A The compound shown in formula (I) (this compound A) can be prepared by reacting the compound shown in formula (B1) (hereinafter referred to as compound (B1)) with the compound shown in formula (M1) (hereinafter referred to as compound (M1)) in the presence of a palladium catalyst and a base.

[0562] [Chemical Formula 48] [In the formula, X] 51 Met represents a chlorine atom, bromine atom, iodine atom, or trifluoromethanesulfonyloxy group. 51 This represents B(OH)₂ or 4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl; other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons such as hexane, toluene, and xylene; ethers such as methyl tert-butyl ether (MTBE), tetrahydrofuran (THF), and 1,2-dimethoxyethane (DME); halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene; amides such as dimethylformamide (DMF) and N-methylpyrrolidone (NMP); esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; dimethyl sulfoxide (DMSO), water, and mixtures of two or more of them.

[0563] Examples of palladium catalysts used in the reaction include palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride.

[0564] Examples of bases used in reactions 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 bicarbonates such as sodium bicarbonate and potassium bicarbonate (hereinafter referred to as alkali metal bicarbonates); alkali metal bicarbonates, sodium fluoride, and tripotassium phosphate.

[0565] In the reaction, compound (M1) is typically used in a ratio of 0.5 to 2 moles relative to 1 mole of compound (B1), palladium catalyst is typically used in a ratio of 0.01 to 0.3 moles, and base is typically used in a ratio of 1 to 10 moles.

[0566] The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0567] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating compound A.

[0568] The compound (M1) is known or can be manufactured using known methods.

[0569] Manufacturing method B The compound shown in formula (I) (this compound A) can also be prepared by reacting the compound shown in formula (B2) (hereinafter referred to as compound (B2)) with the compound shown in formula (M2) (hereinafter referred to as compound (M2)) in the presence of a palladium catalyst and a base.

[0570] [Chemical Formula 49] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out in accordance with manufacturing method A, using compound (M2) instead of compound (B1) and compound (B2) instead of compound (M1).

[0571] The compound (M2) is known or can be manufactured using known methods.

[0572] Manufacturing method C The compound represented by formula (Ia) (hereinafter referred to as compound (Ia)). Wherein, the ring A of compound (Ia) 5 In, with C(OH)(R) 1 The bonded atom is a carbon atom. It can be produced by reacting an organolithium reactant, which is generated by reacting the compound shown in formula (B3) (hereinafter referred to as compound (B3)) with the compound shown in formula (M3) (hereinafter referred to as compound (M3)), with the compound shown in formula (M4) (hereinafter referred to as compound (M4)).

[0573] [Chemical Formula 50] [In the formula, X] 52 X represents a bromine atom or an iodine atom. 53 This indicates butyl, sec-butyl, or tert-butyl; other symbols have the same meaning as described above. Specifically, in compounds (M4) and (Ia), the symbol R... 1 The bonded carbon atoms bonded to ring A 5 The atom is a carbon atom. First, a method for preparing an organolithium reactant from compound (B3) is described.

[0574] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include hydrocarbons, ethers, and mixtures of two or more of them.

[0575] In the reaction, compound (M3) is usually used in a ratio of 0.5 to 2 moles relative to 1 mole of compound (B3).

[0576] The reaction temperature is typically in the range of -78°C to the boiling point of the solvent. The reaction time is typically in the range of 0.1 to 120 hours.

[0577] Next, a method for producing compound (Ia) from an organolithium reactant is described.

[0578] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include hydrocarbons, ethers, and mixtures of two or more of them.

[0579] In the reaction, compound (M4) is typically used in a ratio of 0.5 to 2 moles relative to 1 mole of organolithium reactant.

[0580] The reaction temperature is typically in the range of -78°C to the boiling point of the solvent. The reaction time is typically in the range of 0.1 to 120 hours.

[0581] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating compound (Ia).

[0582] Compounds (B3), (M3), and (M4) are known or can be manufactured using known methods.

[0583] Manufacturing method D Compound (Ia) can also be produced by reacting a Grignard reagent, which is generated by reacting compound (B3) with a compound of formula (M5) (hereinafter referred to as compound (M5)), with compound (M4).

[0584] [Chemical Formula 51] [In the formula, X] 54 This indicates a chlorine or bromine atom; other symbols have the same meaning as described above. In compounds (M4) and (Ia), the symbol R... 1 The bonded carbon atoms bonded to ring A 5 The atom is a carbon atom. The reaction can be carried out using compound (M5) instead of compound (M3) according to manufacturing method C.

[0585] Compound (M5) is a commercially available compound or can be manufactured using known methods.

[0586] Manufacturing method E Compound (Ia) can also be produced by reacting an organolithium reactant, which is generated by reacting the compound (M6) shown in formula (M6) with compound (M3), with the compound (M7) shown in formula (M7).

[0587] [Chemical Formula 52] [In the formula, the symbols have the same meaning as in the preceding text. Among them, in compounds (M6) and (Ia), the symbol with respect to R...] 1 The bonded carbon atoms bonded to ring A 5 The atom is a carbon atom. The reaction can be carried out using compound (M6) instead of compound (B3) and compound (M7) instead of compound (M4), in accordance with manufacturing method C.

[0588] Compounds (M6) and (M7) are known or can be manufactured using known methods.

[0589] Manufacturing method F Compound (Ia) can also be produced by reacting a Grignard reagent, which is generated by reacting compound (M6) with compound (M5), with compound (M7).

[0590] [Chemical Formula 53] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out in accordance with manufacturing method C, using compound (M6) instead of compound (B3), compound (M5) instead of compound (M3), and compound (M7) instead of compound (M4).

[0591] Manufacturing method G The compound shown in formula (Ib) (hereinafter referred to as compound (Ib)) can be prepared by dehydroxylation of compound (Ia).

[0592] [Chemical Formula 54] [In the formula, the symbols have the same meaning as in the preceding text. Among them, in compounds (Ia) and (Ib), the symbol with respect to R...] 1 The bonded carbon atoms bonded to ring A 5 The atom is a carbon atom. Examples of dehydroxylation methods include catalytic hydrogenation reduction reactions or reactions with phosphorus tribromide.

[0593] First, a method for producing compound (Ib) from compound (Ia) by means of a catalytic hydrogenation reduction reaction is described.

[0594] Catalytic hydrogenation can be carried out by reacting compound (Ia) with hydrogen in the presence of a solvent and a catalyst.

[0595] Examples of solvents used in the reaction include alcohols such as methanol and ethanol (hereinafter referred to as alcohols); esters, acetic acid, and mixtures of two or more of them.

[0596] Examples of catalysts used in reactions include palladium on carbon.

[0597] The pressure of hydrogen in the reaction is usually 1 to 5 atmospheres.

[0598] In the reaction, the catalyst is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (Ia).

[0599] The reaction temperature is typically in the range of 10 to 50°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0600] Next, a method for producing compound (Ib) from compound (Ia) by reacting with phosphorus tribromide is described.

[0601] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include hydrocarbons, ethers, and mixtures of two or more of them.

[0602] In the reaction, phosphorus tribromide is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (Ia).

[0603] The reaction temperature is typically in the range of 0°C to the boiling point of the solvent. The reaction time is typically in the range of 0.1 to 120 hours.

[0604] After the reaction is complete, water is added to the reaction mixture, and the organic layer is washed with an alkaline aqueous solution (e.g., a saturated sodium bicarbonate solution) as needed. Post-treatment operations such as drying and concentrating the organic layer are then performed, thereby enabling the separation of compound (Ib).

[0605] Manufacturing method H The compound shown in formula (Ic) (hereinafter referred to as compound (Ic)) can be produced by oxidation of compound (Ia).

[0606] [Chemical Formula 55] [In the formula, the symbols have the same meaning as in the preceding text. Among them, in compounds (Ia) and (Ic), the symbol with respect to R...] 1 The bonded carbon atoms bonded to ring A 5 The atom is a carbon atom. The oxidation reaction can be carried out according to the methods described in Natural Product Reports, 2011, 28, 1722-1754, etc.

[0607] Manufacturing Method I [Chemical Formula 56] [In the formula, the symbols have the same meaning as in the preceding text.] Reduction reactions are typically carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, and mixtures of two or more of them.

[0608] Sodium borohydride can be cited as an example of a reducing agent used in the reaction.

[0609] In the reaction, the reducing agent is usually used in a ratio of 0.5 to 2 moles relative to 1 mole of compound (Ic).

[0610] The reaction temperature is typically in the range of 0 to 100°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0611] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating compound (Ia).

[0612] Manufacturing Method J The compound represented by formula (Id) (hereinafter referred to as compound (Id)). Wherein, the ring A of compound (Id) 5 In, with C(OH)(R) 1 The bonded atom is a carbon atom. It can be produced by reacting compound (Ia) with compound (M8) shown in formula (M8) in the presence of a base.

[0613] [Chemical Formula 57] [In the formula, X] 55 This symbol represents a fluorine atom, chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, or trifluoromethanesulfonyloxy group; other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, hydrocarbons, amides, DMSO, water, and mixtures of two or more of them.

[0614] Examples of bases used in reactions include alkali metal hydrides, alkali metal carbonates, organic bases, sodium hydride, and tripotassium phosphate.

[0615] X 55 In the case of bromine atoms, iodine atoms, or trifluoromethanesulfonyloxy groups, metal catalysts and ligands can be added as needed to carry out the reaction.

[0616] Examples of metal catalysts used in the reaction include palladium catalysts such as palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride; nickel catalysts such as bis(cyclooctadiene)nickel(O) and nickel(II) chloride; and copper catalysts such as copper(I) iodide and copper(I) chloride. When a metal catalyst is used in the reaction, it is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (Ia).

[0617] Examples of ligands used in the reaction include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When using ligands in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (Ia).

[0618] In the reaction, the compound (M8) is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (Ia), and the base is usually used in a ratio of 1 to 10 moles.

[0619] The reaction temperature is typically in the range of -20℃ to 200℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0620] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain the compound (Id).

[0621] The compound (M8) is known or can be manufactured using known methods.

[0622] Manufacturing method K The compound shown in formula (Ie) (hereinafter referred to as compound (Ie)) can be prepared by reacting the compound shown in formula (B4) (hereinafter referred to as compound (B4)) with the compound shown in formula (M9) (hereinafter referred to as compound (M9)) in the presence of a condensing agent.

[0623] [Chemical Formula 58] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include nitriles, ethers, hydrocarbons, amides, DMSO, water, and mixtures of two or more of them.

[0624] Examples of condensing agents used in the reaction include cyanomethylene tributylphosphine; mixtures of azodiesters such as diethyl azodicarbonate and di(methoxyethyl) azodicarbonate with triphenylphosphine.

[0625] In the reaction, compound (M9) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (B4), and condensing agent is usually used in a ratio of 1 to 5 moles.

[0626] The reaction temperature is typically in the range of 0℃ to 150℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0627] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (Ie).

[0628] The compound (M9) is known or can be manufactured using known methods.

[0629] Manufacturing method L Compound (Ie) can also be produced by reacting the compound shown in formula (B5) (hereinafter referred to as compound (B5)) with compound (M9) in the presence of a base.

[0630] [Chemical Formula 59] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, hydrocarbons, amides, DMSO, water, and mixtures of two or more of them.

[0631] Examples of bases used in reactions include alkali metal hydrides, alkali metal carbonates, organic bases, sodium hydride, and tripotassium phosphate.

[0632] In the reaction, compound (M9) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (B5), and the base is usually used in a ratio of 1 to 5 moles.

[0633] The reaction temperature is typically in the range of -20℃ to 150℃. The reaction time is typically in the range of 0.1 to 72 hours.

[0634] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (Ie).

[0635] The compound (B5) is known or can be manufactured using known methods.

[0636] Reference manufacturing method A The compound shown in formula (C2) (hereinafter referred to as compound (C2)) can be produced by reacting an organolithium reactant generated by reacting compound (M6) with compound (M3) with the compound shown in formula (C1) (hereinafter referred to as compound (C1)).

[0637] [Chemical Formula 60] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M6) instead of compound (B3) and compound (C1) instead of compound (M4), according to manufacturing method C.

[0638] The compound (C1) is known or can be manufactured using known methods.

[0639] Reference manufacturing method B Compound (C2) can also be produced by reacting a Grignard reagent, which is generated by reacting compound (M6) with compound (M5), with compound (C1).

[0640] [Chemical Formula 61] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M6) instead of compound (B3) and compound (C1) instead of compound (M4), according to manufacturing method D.

[0641] Reference manufacturing method C The compound shown in formula (C4) (hereinafter referred to as compound (C4)) can be prepared by reacting the compound shown in formula (C3) (hereinafter referred to as compound (C3)) with compound (M9) in the presence of a condensing agent.

[0642] [Chemical Formula 62] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (C3) instead of compound (B4) according to manufacturing method K.

[0643] The compound (C3) is known or can be manufactured using known methods.

[0644] Reference manufacturing method D Compound (C6) can be prepared by reacting compound (C5) (hereinafter referred to as compound (C5)) with compound (M9) in the presence of a base.

[0645] [Chemical Formula 63] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (C5) instead of compound (B5) according to manufacturing method L.

[0646] The compound (C5) is known or can be manufactured using known methods.

[0647] Reference manufacturing method E The compound shown in formula (C7) (hereinafter referred to as compound (C7)) can be prepared by reacting compound (B1) with bis(pinacol)diboron in the presence of a base and a palladium catalyst.

[0648] [Chemical Formula 64] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using bis(pinacol)diboron instead of compound (M1) according to manufacturing method A.

[0649] Reference manufacturing method F Compound (B4) can be produced by reducing the compound shown in formula (C8) (hereinafter referred to as compound (C8)).

[0650] [Chemical Formula 65] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, and mixtures of two or more of them.

[0651] Sodium borohydride can be cited as an example of a reducing agent used in the reaction.

[0652] In the reaction, the reducing agent is usually used in a ratio of 0.5 to 2 moles relative to 1 mole of compound (C8).

[0653] The reaction temperature is typically in the range of 0 to 100°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0654] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating the compound (B4).

[0655] The compound (C8) is known or can be manufactured using known methods.

[0656] Reference manufacturing method G The compound shown in formula (C10) (hereinafter referred to as compound (C10)) can be produced by oxidizing the compound shown in formula (C9) (hereinafter referred to as compound (C9)).

[0657] [Chemical Formula 66] [In the formula, the symbols have the same meaning as in the preceding text.] The oxidation reaction can be carried out according to the methods described in Natural Product Reports, 2011, 28, 1722-1754, etc.

[0658] Compound (C9) can be manufactured according to either Reference Manufacturing Method A or Reference Manufacturing Method B.

[0659] Reference manufacturing method H The compound shown in formula (C11) (hereinafter referred to as compound (C11)) can be prepared by thiocarbonylation of compound (C10).

[0660] [Chemical Formula 67] [In the formula, the symbols have the same meaning as in the preceding text.] The thiocarbonylation reaction can be carried out according to the methods described in Tetrahedron, 1985, 41, 5061-5087, etc.

[0661] Reference Manufacturing Method I The compound represented by formula (C12) (hereinafter referred to as compound (C12)) can be produced by reacting compound (C10) with compound (M10) or a salt of compound (M10).

[0662] [Chemical Formula 68] [In the formula, the symbols have the same meaning as in the preceding text.] Examples of salts of compound (M10) include hydrochloride and sulfate.

[0663] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, and mixtures of two or more of them.

[0664] A base may also be added to the reaction as needed. Examples of bases used in reactions include organic bases; alkali metal carbonates; alkali metal bicarbonates; sodium hydride; and tripotassium phosphate. When a base is used in a reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of the compound (C10).

[0665] In the reaction, compound (M9) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (C10).

[0666] The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0667] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating the compound (C12).

[0668] Salts of compound (M10) are known or can be produced by known methods.

[0669] Reference Manufacturing Method J The compound shown in formula (C13) (hereinafter referred to as compound (C13)) can be produced by reacting compound (M6) with the compound shown in formula (M11) (hereinafter referred to as compound (M11)).

[0670] [Chemical Formula 69] [In the formula, Met] 52 This represents B(OH)₂, 4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl, or ZnBr; other symbols have the same meaning as above. The reaction can be carried out in accordance with manufacturing method A, using compound (M6) instead of compound (B1) and compound (M11) instead of compound (M1).

[0671] Alternatively, the reaction can be carried out according to the methods described in Journal of Medicinal Chemistry, 2017, 60, (23), 9769-9789, or International Publication No. 2011 / 075515.

[0672] The compound (M11) is known or can be manufactured using known methods.

[0673] Reference manufacturing method K The compound shown in formula (B1-1) (hereinafter referred to as compound (B1-1)) can be produced by cyclization reaction of the compound shown in formula (C14) (hereinafter referred to as compound (C14)).

[0674] [Chemical Formula 70] [In the formula, R] 1v R 2v R 3v R 4v R 5v and R 6v "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 , cyano, nitro, halogen atom or hydrogen atom, R 9v This indicates C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, and 3-8 membered non-aromatic heterocyclic groups that can be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, and phenyl groups and C(O)R groups that can be substituted by one or more substituents selected from group C. 29 [The symbol , or hydrogen atom, and other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of them.

[0675] A base may be added to the reaction as needed.

[0676] Examples of bases used in reactions include organic bases, alkali metal carbonates, alkali metal bicarbonates, or phosphazene bases such as 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphine-enzymylamino]-2λ5,4λ5-diphenyl (phosphine nitrogen compound).

[0677] In the reaction, the base is usually used in a ratio of 0.01 to 10 moles relative to 1 mole of compound (C14).

[0678] The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0679] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating compound (B1-1).

[0680] Alternatively, the reaction can be carried out according to the methods described in Tetrahedron Letters, 2022, 89, 153599, Org. Lett, 2022, 24, 51, 9447, J. Am. Chem. Soc. 2014, 136, 35, 12217, etc.

[0681] The compound (C14) can be prepared according to known methods, such as those described in Tetrahedron Letters, 2022, 89, 153599, Org. Lett, 2022, 24, 51, 9447, J. Am. Chem. Soc. 2014, 136, 35, 12217, etc.

[0682] Reference manufacturing method L The compound shown in formula (B1-2) (hereinafter referred to as compound (B1-2)) can be produced by reacting the compound shown in formula (C15) (hereinafter referred to as compound (C15)) with the compound shown in formula (M1-1) (hereinafter referred to as compound (M1-1)).

[0683] [Chemical Formula 71] In the formula, Q v Represents oxygen atom, sulfur atom, or NR. 9v Other symbols have the same meaning as those in the preceding text. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of them.

[0684] A base may be added to the reaction as needed.

[0685] Examples of bases used in reactions include organic bases, alkali metal carbonates, and alkali metal bicarbonates.

[0686] In the reaction, compound (M1-1) is usually used in a ratio of 0.5 to 10 moles relative to 1 mole of compound (C15), and base is usually used in a ratio of 1 to 10 moles.

[0687] The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0688] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating the compound (B1-2).

[0689] Alternatively, the reaction can be carried out according to the methods described in J. Chem. Soc., Perkin Trans. 1, 1977, 2328-2332.

[0690] The compound (C15) is known or can be manufactured using known methods.

[0691] Reference manufacturing method M The compound shown in formula (B1-3) (hereinafter referred to as compound (B1-3)) can be prepared by reacting the compound shown in formula (C16) (hereinafter referred to as compound (C16)) with the compound shown in formula (M1-2) (hereinafter referred to as compound (M1-2)) in the presence of sodium hypochlorite.

[0692] [Chemical Formula 72] [In the formula, R] 1w R 2w R 3w and R 4w "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 [The symbols cyano, nitro, halogen, or hydrogen atom, and other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, DMSO, water, and mixtures of two or more of them.

[0693] Examples of bases used in reactions include organic bases, alkali metal carbonates, and alkali metal bicarbonates.

[0694] In the reaction, compound (M1-2) is usually used in a ratio of 0.5 to 10 moles relative to 1 mole of compound (C16), and sodium hypochlorite is usually used in a ratio of 1 to 10 moles.

[0695] The reaction temperature is typically in the range of 0 to 150°C. The reaction time is typically in the range of 0.1 to 120 hours.

[0696] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out, thereby separating compounds (B1-3).

[0697] The compound (C16) is known or can be manufactured using known methods.

[0698] The compounds of the present invention may be used in combination or in combination with one or more components (hereinafter referred to as the component) selected from the group consisting of group (a), group (b), group (c) and group (d) below.

[0699] The aforementioned combination or use refers to using the compound of the present invention and the ingredient simultaneously, separately, or at intervals.

[0700] When the compound of the present invention and the ingredient are used simultaneously, the compound of the present invention and the ingredient may be contained in separate formulations or in the same formulation.

[0701] One aspect of the present invention is a composition comprising one or more components selected from groups (a), (b), (c) and (d) (i.e., the component itself) and the compound of the present invention (hereinafter referred to as composition A).

[0702] Group (a) comprises acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate 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), juvenile hormones, multisite inhibitors, chordal organ TRPV channel modulators, mite growth inhibitors, and insect midgut membrane disruption derived from microorganisms. This group comprises insecticides, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitin biosynthesis inhibitors, ecdysone 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, ranotin receptor modulators (e.g., diamide-based insecticides), string organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients. These ingredients are described according to their IRAC-based mechanisms of action.

[0703] Group (b) comprises nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., aniline pyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-point contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are described according to the classification based on FRAC-based mechanisms of action.

[0704] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0705] Group (d) is the group containing the repellent component.

[0706] Examples of combinations of this component with the compounds of the present invention are described below. For example, alanycarb + SX refers to the combination of alanycarb and SX.

[0707] It should be noted that the abbreviation SX refers to the compound of the present invention selected from any of the compound groups SX1 to SX98. Furthermore, all the ingredients described below are known ingredients and can be obtained from commercially available formulations or manufactured by known methods. In the case of microorganisms, these ingredients can also be obtained from microbial depositories. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0708] The combination of the component of group (a) above with the compounds of the present invention: Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acridine lactate + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide 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, bentioflumin + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX, bisulflufen + 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, Chlorpicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chlorafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanavalin A A) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cybenzoxasulfyl + 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, Cyproflanilide + SX, Cyromazine + SX, Dazomet + SX, Deltamethrin + SX, Demeton-S-meth yl) + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, diloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate octaborate) + SX, disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol + SX, doramectin + SX, dried leaves of Dryopteris filix-mas + SX, emamectin-benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl)phenyl thiophosphonate, O-ethylO-(4-nitrophenyl)phenylphosphonothioate +SX, epsilon-metofluthrin +SX, epsilon-momfluorothrin +SX, esfenvalerate +SX, ethiofencarb +SX, ethion +SX, etiprole +SX, ethoprophos +SX, etofenprox +SX, etoxazole +SX, extract of Artemisia absinthium +SX, extract of Azadirachta indica +SX, extract of Cassia nigricans +SX, extract of clitoria ternatea +SX, extract of Symphytum officinale) + SX, extract of Chenopodium ambrosioides + SX, extract of Tanacetum vulgare + SX, extract of Urtica dioica + SX, extract of Viscum album + 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, fometoquin + SX, flonicamid + SX, fluacrypyrim + SX, fluazaindolizine + SX, fluazuron + SX, flubendiamide + SX, fluchlordiniliprole + SX, flucycloxuron + SX, flu... Cypermethrin +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 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) +SX, hydramethylnon +SX, hydroprene +SX, imicafos +SX, imidacloprid +SX, imidaclothiz +SX, imiprothrin +SX, indazapyroxamet +SX, indoxacarb +SX, isocycloseram +SX, isofenphos +SX, isoflurane +SX, isoflurane +SX, isoprocarb +SX, isopropyl-O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester 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, Chenopodium anthelminticum seed oil (oil of the seeds of Chenopodium)Anthelminticum + 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, Phosphamidon + S X, phosphine + SX, phoxim + SX, piocarbamate + SX, piperflanilide + SX, pirimicarb + SX, pirimitosophos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate alginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, piraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyrimin ostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borateSodium metaborate + SX, spidoxamat + SX, spintoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride fluoride + SX, tartaremetic + 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 ambrosioidesThe following are listed: nearambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodi m)+SX, tiapyrachlor+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, vadescana+SX, vamidothion+SX, wood extract of the magnesia tree (wood Extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothiohexacyclobutane-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)propionamide (1118626-57-5)+SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3 -(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9)+SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazole-4-yl]-2-(methanesulfonyl)propionamide (2396747-83-2)+SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazolyl-5-yl]-N-ethyl-3-(methanesulfonyl)propionamide+SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazole-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-0) 9-3) +SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-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)pyrrolidine-1-yl]phenyl}methyl)cyclopropanecarboxamide +SX, 7-fluoro-N-[1-(methylthioalkyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 7-fluoro-N-[1-(methanethionyl)-2-methyl [1-[1-(methanesulfonyl)-2-methylpropane-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide +SX, 7-fluoro-N-[1-(methanesulfonyl)-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]pyridolo[2,3-b][1,4]oxazapyro-10-one (2607927-97-7) +SX, Cry1Ab protein from Bacillus thuringiensis +SX, Cry1Ac protein from Bacillus thuringiensis +SX, Cry1Fa protein from Bacillus thuringiensis +SX, Cry1A.105 protein from Bacillus thuringiensis +SX, Cry2Ab protein from Bacillus thuringiensis +SX, Vip3A protein from Bacillus thuringiensis +SX, mCry3A protein from Bacillus thuringiensis The following proteins were tested: Cry3Ab protein from Bacillus thuringiensis + SX, Cry3Bb protein from Bacillus thuringiensis + SX, Cry34Ab1 / Cry35Ab1 protein from Bacillus thuringiensis + SX, Adoxophyes orana granulosis virus strain BV-0001 + SX, Anticarsia gemmatalis mNPV for soybean leafroller + SX, Autographa californica mNPV for alfalfa silver-striped moth + SX, and Cydiapomonella GV strain for codling moth. V15) + SX, Cydia pomonella GV strain V22 + SX, Cryptophorbia leucotreta GV + SX, Dendrolimus punctatus punctatusThe following viruses were detected: Cypovirus + SX, Helicoverpa armigera NPV strain BV-0003 + SX, Helicoverpazea NPV + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprionsertifer NPV + SX, and Nosema microsporidia. locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodopteraexigua mNPV+SX, Spodoptera littoralis mNPV+SX, Spodoptera litura NPV+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637 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 H5a5b2362serotype H5a5b)+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD#32+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 strain AM65-52) + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 BMP123)+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348+SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841.The following strains were tested: * *Kurstakistrain EG7841* + SX; * *Bacillus thuringiensis subsp. Kurstaki* strain EVB113-19 + SX; * *Bacillus thuringiensis subsp. Kurstaki* strain F810 + SX; * *Bacillus thuringiensis subsp. Kurstaki* strain HD-1 + SX; * *Bacillus thuringiensis subsp. Kurstaki* strain PB54 + SX; * *Bacillus thuringiensis subsp. Kurstaki* strain SA-11. SA-11) + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. Morrison + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 24-91)+SX, Bacillus thuringiensis var. dendrolimus+SX, Bacillus thuringiensis var. galleriae+SX, Bacillus thuringiensis strain BMP144The following strains of Bacillus thuringiensis were found to be infected with the following strains: Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, and Beauveria bassiana ANT-03 strain. The following bacteria were tested: *Beauveria bassiana* strain ANT-03 + SX, *Beauveria bassiana* strain ATCC74040 + SX, *Beauveria bassiana* strain GHA + SX, *Beauveria brongniartii* + SX, *Burkholderia rinojensis* strain A396 + SX, *Chromobacterium subtsugae* strain PRAA4-1T + SX, *Dactyllela ellipsospora* + SX, *Dectylaria thaumasia* + SX, *Hirsutella minnesotensis* + SX, *Hirsutella rhossiliensis* + SX, *Hirsutella thompsonii* + SX, and *Lagenidium*. giganteum) + SX, Lecanicillium lecanii strain KV01 + SX, conidia of Lecanicillium lecanii strain DAOM198499The following strains of bacteria were tested: DAOM198499 + SX, conidia of strain DAOM216596 (Lecanicillium lecanii), strain Ve6 of Lecanicillium muscarium, strain F52 of Metarhizium anisopliae + SX, strain var. acridum of Metarhizium anisopliae + SX, strain BIPESCO 5 / F52 of Metarhizium anisopliae + SX, strain flavoviride of Metarhizium flavoviride + SX, strain Monacrosporium phymatopagum + SX, and strain Apopka97 of Paecilomyces fumosoroseus. 97) +SX, Paecilomyces lilacinus strain 251 +SX, Paecilomyces tenuipes strain T1 +SX, Paenibacillus popilliae +SX, Pasteuria nishizawaestrain Pn1 +SX, Pasteuria penetrans +SX, Pasteuria usgae +SX, Pasteuria thornei +SX, Serratia entomophila +SX, Verticillium chlamydosporium +SX, Verticillium lecani strain NCIM1312 +SX, Wolbachia pipientis)+SX.

[0709] The combination of this component of group (b) above with the compounds of the present invention: 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, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, basic copper chloride oxychloride) + SX, copper(II) sulfate (copper(II))sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX Diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogen phosphate Hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acidbisethylenediamine copper(II) salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epixaconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Extract of Melaleuca alternifolia + SX, Extract of Reynoutria sachalinensis + SX, Extract of the cotyledons of lupine plantlets ("BLAD") + SX, garlic extract (extract of Allium)Satisfactionum + SX, Equisetum arvense extract + SX, Tropaeolum majus extract + SX, Famoxadone + SX, Fenamidone + SX, Fenaminstrobin + SX, Fenarimol + SX, Fenbuconazole + SX, Feneptamidoquin + SX, Fenfuram + SX, Fenhexamid + SX, Fenopyramid + SX, Fenoxanil + SX, Fenpiclonil + SX, Fenpicoxamid + SX, Fenpropidin + SX, Fenpropimorph + SX, Fenpyrazamine + SX, Fentin acetate) + SX, triphenyltin chloride (fentin chloride) + SX, triphenyltin hydroxide (fentin)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, fluoxex Fluoxytioconazole + SX, fluquinconazole + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX, fosetyl-aluminium + SX, furberidazole + SX, furalaxyl + SX, furametpyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX 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, isoflucypram + SX, isoprethiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, leaves and bark of oak treesQuercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + ​​SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metrilpicoxamid + SX, Metconazole + SX, Methasulfocarb + S X, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofuronamide + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic 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 phosphatedihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, piraclostrobin + 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 extract) +SX, quinconazole +SX, quinofumelin +SX, quinoxyfen +SX, quintozene +SX, saponins of Chenopodium quinoa +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, Thioprazan + SX, Thioprazan-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos -methyl)+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX, triadimefon+SX, triadimenol+SX, triazoxide+SX, chlorpyrifos+SX, tricyclazole+SX, triridemorph+SX, trifloxystrobin+SX, triflumizole+SX, triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX, vinclozolin+SX, yellow mustard powder ( Mustard powder + SX, thiamethoxam + SX, zineb + ​​SX, ziram + SX, zoxamide + SX N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidin (1202781-91-6)+SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidin (929908-57-6)+SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidin (1052688-31-9)+SX, N '-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidin (2055589-28-9)+SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidin (2055756-21-1)+SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidin (2062599-39-5)+SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl- [5-Methoxyphenyl]-N-isopropyl-N-methylformamidinium (2101814-55-3)+SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidinium (1817828-69-5)+SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (1362477-26-6)+SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin- 2-yl]quinazolin (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-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-carboxylic acid methyl ester (1791398-02-1)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (20 19215-86-0)+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-imidazol-5-carboxylonitrile (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylonitrile (2018317-25-2) )+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082660-27-1)+SX, ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879- 98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl] Ethylamino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098918-25-1) + 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)propionamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropionamide + SX, N-methoxy-N'-methyl ... 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, N-acetyl-2-(ethanesulfonyl)-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-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]- L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester +SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)but-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]ethyl 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 ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester) N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate)+SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropionic acid +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)propionic acid +SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionic acid +SX, 3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butyramide + 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)pyrrolidone-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 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-oxazinane-3-one+SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azacycloheptane-2-one+SX, 4,4 -Dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one +SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-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-(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-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX,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-1,2,4-triazol-3-amine +SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol- [3-yl]benzamide +SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate methyl ester +SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate ethyl ester +SX, 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate methyl ester +SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl] ]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide +SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile +SX, 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolane-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]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-methylthiazol-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3,4]oct-1-yl)-5-methylthiazol-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazol-4-carboxamide +SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2 -[(2-methylpropionyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +S X, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-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-(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-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluoromethyl ...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 + S X, 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, 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-methylbutane-2-yl)-2-methylpropionamide +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-methylbutane-2-yl)-2,2-di ...hydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2,2-dimethylpropionamide +SX, N-((2S)-1-{3-[2 [3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl]propane-2-yl)-2-methylpropionamide + 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}propane-2-yl)-2-methylpropionamide + 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}propane-2-yl)-2-methylpropionamide +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, ({ 5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl]methyl carbamate + SX, (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-2-acrylate + SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-acrylate + SX, (Z)-2-[(3-isopropyl-1H] [-pyrazole-1-yl)-2-methylphenoxy]-3-methoxy-2-acrylate methyl ester +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-(pyrazole-1-yl)-2-methylphenoxy-3-methoxy-2-acrylate methyl ester ... [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-dimethylisoquinoline-4(3H)-one + SX, (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]-2-acrylate methyl ester + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 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 QST713) + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727F727)+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 strain CGF2856+SX. The following strains of Bacillus subtilis were tested: simplexstrain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, and Bacillus subtilis strain HAI0404. HAI0404) + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002The following strains were tested: Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, and Burkholderia cepacia type Wisconsin strain J82. J82)+SX, Burkholderia cepacia type Wisconsinstrain 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 CGE234M403) + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxastrain AC-1AC-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, Pseudozyma flocculosa PF-A22UL strain + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61K61) + 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 strain SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 T34) + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichodermagamsii strain ICC080 ICC080) + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 1494414944)+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 T22)+SX, Trichoderma harzianum strain T39+SX, Trichoderma harzianum strain T78+SX, Trichoderma harzianum strain TH35+SX, Trichoderma polysporum strain IMI206039+SX, Trichoderma stromaticum+SX, Trichoderma virens strain G-41+SX, Trichoderma virens strain GL-21+SX, Trichodermaviride+SX, Variovorax paradoxus strain CGF4526+SX, Harpin protein+SX.

[0710] The combination of the component of group (c) above with the compounds of the present invention: 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 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, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propane-1-ol + SX, Claroideoglomusetunicatum) + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Giaspora margarita + SX, Giaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 strain + SX, Rhizophagus irregularis DAOM Azospirillum caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 strain + SX, Bradyrhizobium japonicum TA-11 strain + SX, Bradyrhizobium japonicum USDA 110 strain + SX, Bradyrhizobium liaoningense strain + SX, Bradyrhizobium lupini strain + SX, Delftia acidovorans RAY209 strain + SX, Mesorhizobium ciceri strain + SX, MesorhizobiumRhizobium huakii + 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 meliloti + SX, Zucchini yellow mosaic virus (attenuated strain) YellowMosaik Virus weak strain)+SX.

[0711] The combination of the component of group (d) above with the compounds of the present invention: Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0712] The ratio of the compound to the component of this invention is not particularly limited, but examples of weight ratios (compound of this invention: component of this invention) of 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, etc.

[0713] This compound, or the compound or composition A of this invention, can prevent and control plant diseases caused by plant pathogenic microorganisms such as fungi, oomycetes, phytomyxea, and bacteria. Examples of fungi include, for example, Ascomycota, Basidiomycota, Blastodactyla, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specifically, examples include, for instance, the following. The scientific names of the plant pathogenic microorganisms causing each disease are shown in parentheses.

[0714] Rice diseases: Blight (Pyricularia oryzae), Sesame leaf blight (Cochliobolus miyabeanus), Sheath blight (Rhizoctonia solani), Bakanae disease (Gibberella fujikuroi), Yellowing and stunting disease (Sclerophthora macrospora), False rice blast and panicle blight (Epicoccum nigrum), Seedling damping-off (Trichodermaviride, Rhizopus oryzae), False sheath blight (Waiteacircinata), Brown sclerotinia (Ceratobasidium setariae), Brown sheath blight (Thanatephorus) Rice smut (Ustilaginoidea virens), grain smut (Tilletia horrida, Tilletia barclayana). Wheat diseases: Powdery mildew (Blumeria graminis), Fusarium 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 sclerotium rot (Typhula incarnata, Typhula ishikariensis), Large sclerotium rot (Sclerotinia northernis) (borelis)), brown root rot (Pythium spp.)), loose smut (Ustilago tritici)), smut (Tilletia caries, Tilletia controversa)), eye spot (Pseudocercosporella herpotrichoides)), leaf blight (Septoria tritici)), glume blight (Stagonospora nodorum)), yellow spot (Pyrenophora tritici-repentis)), seedling damping-off (Rhizoctonia solani) caused by Rhizoctonia spp.), damping-off (Gaeumannomyces graminis)), and blast disease (Pyricularia graminis-tritici). Barley diseases: Powdery mildew (Blumeria graminis), Fusarium head blight (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Barley stalk rust (Puccinia hordei), Loose smut (Ustilago nuda), Cloud blight (Rhynchosporium secalis), Net blight (Pyrenophora teres), Leaf spot (Cochliobolus sativus), Leaf stripe (Pyrenophora teres). graminea), Ramularia collo-cygni leaf spot, and Rhizoctonia solani (a fungus causing seedling damping-off). Corn diseases: Rust (Puccinia sorghi), Southern rust (Puccinia polysora), Large leaf spot (Setosphaeria turcica), Tropical rust (Physopella zeae), Sesame leaf blight (Cochliobolus heterostrophus), Anthracnose (Colletotrichum graminicola), Gray leaf spot (Cercospora zeae-maydis), Brown spot (Kabatiella zeae), Phaeosphaeria maydis, Stenocarpella maydis, Stenocarpellamacrospora, Stem rot (Fusarium graminii). graminearum, Fusarium verticilioides, Colletotrichum graminicola, Ustilago maydis (corn smut), Physoderma maydis (corn stalk rot), and Phyllachora maydis (corn black spore causal agent). Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternariagossypii), Root black rot (Thielaviopsis basicola). Coffee diseases: Rust (Hemileia vastatrix) and leaf spot (Cercospora coffeicola). Diseases of rapeseed: Sclerotinia sclerotiorum, Alternaria brassicae, Phona lingam, Pyrenopeziza brassicae. Sugarcane diseases: Rust (Puccinia melanocephela, Pucciniakuehnii), Smut (Ustilago scitaminea); Sunflower diseases: Rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), penicillium italicum, blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger; Apple diseases: Blossom blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), blight (Phytophthora racactorum), red spot (Gymnosporangium). juniperi-virginianae), Gymnosporangium yamadae); Pear diseases: Black spot (Venturia nashicola, Venturiapirina), Black spot (Alternaria alternata Japanese pearpathotype), Gymnosporangium haraeanum (Gymnosporangium haraeanum). Peach diseases: Gray spot (Monilinia fructicola), Black spot (Cladosporium carpophilum), Brown spot (Phomopsis sp.), Leaf curl (Taphrina deformans), Powdery mildew (Podosphaeraleucotricha). Grape diseases: Black rot (Elsinoe ampelina), Late rot (Glomerella cingulata, Colletotrichum acutatum), Powdery mildew (Uncinula necator), Rust (Neophysopella sp.), Black rot (Guignardiabidwellii), Downy mildew (Plasmopara viticola), Brown spot (Pseudocercospora vitis), White rot (Coniella castaneicola). Diseases of persimmon: Anthracnose (Gloeosporium kaki, Colletotrichum acutatum) , Leaf spot (Cercospora kaki, Mycosphaerella nawae) , Powdery mildew (Phyllactinia kakicola) ; Fig diseases: Rust (Phakopsora nishidana)); Diseases of gourds: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Anthracnose (Didymella bryoniae), Brown spot (Corynespora cassiicola), Fusarium wilt (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Phytophthora capsici, Damping-off (Pythium sp.), Phomopsis sp. root rot. Tomato diseases: ring rot (Alternaria solani)), leaf mold (Cladosporium fulvum)), sooty mold (Pseudocercospora fuligena)), blight (Phytophthora infestans)), powdery mildew (Leveillula taurica)); Eggplant diseases: Brown spot (Phomopsis vexans) , powdery mildew (Erysiphe cichoracearum) , black rot (Corynespora melongenae) , leaf mold (Mycovellosiella nattrassii) , brown spot (Thanatephorus cucumeris) ; 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); Diseases of onions: Rust (Puccinia allii), Black spot (Alternaria porri), Black rot (Sclerotium cepivorum), Sclerotium neck rot (Botrytis squamosa), Leaf blight (Stemphylium vesicarium, Stemphylium botryosum), White mold (Sclerotium rolfsii), White spot leaf blight (Botrytis squamosa). Soybean diseases: Purple blotch (Cercospora kikuchii), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Rust (Phakopsora pachyrhizi), Brown ring spot (Corynespora cassiicola), Anthracnose (Colletotrichum glycines, Colletotrichum truncatum), Damping-off (Rhizoctonia solani), Brown spot (Septoria glycines), Spot disease (Cercospora sojina), Sclerotinia rot (Sclerotinia sclerotiorum). Sclerrotiorum), powdery mildew (Microsphaeradiffusa), stem blight (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death syndrome (Fusarium virguliforme), red crown rot (Calonectria ilicicola), Diaporthe / Phomopsis complex (Diaporthe longicolla, Diaporthe phaseolorum, Phopsis longicolla), and pod anomalies caused by various pathogens. Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), and root rot (Fusarium solani). Peanut diseases: Black spot (Cercospora personata) , Brown spot (Cercospora arachidicola) , White rot (Sclerotium rolfsii) , Red crown rot (Calonectria ilicicola) . Pea diseases: powdery mildew (Erysiphe pisi) and root rot (Fusarium solani). 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), canker (Synchytrium endobioticum). Strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum); Tea diseases: Net cake disease (Exobasidium reticulatum), white spot disease (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis). Tobacco diseases: Red spot disease (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora nicotianae). Diseases of sugar beets: Brown spot (Cercospora beticola) , Leaf blight (Thanatephorus cucumeris) , Root rot (Thanatephorus cucumeris) , Black root disease (Aphanomyces cochlioides) , Rust (Uromyces betae) ; Rose diseases: Black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa). Chrysanthemum diseases: Brown spot (Septoria chrysanthemi-indici) and white rust (Puccinia horiana). Onion diseases: White spot leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), gray rot (Botrytis allii), and sclerotium neck rot (Botrytis squamosa). Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), white mold (Sclerotium rolfsii), seedling blight (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum). Radish diseases: Black spot (Alternaria brassicicola). Sweet potato diseases: vine rot (Fusarium oxysporum f. sp. batatas), basal rot (Diaporthedestruens), black spot (Ceratocystis fimbriata). Diseases of turfgrass: Coin spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), Pythium wilt (Pythium aphandidermatum), anthracnose (Colletotrichum caudatum). Banana diseases: Banana leaf spot (Sigatoka disease) (Mycosphaerella fijiensis, Mycosphaerella musicola)); Diseases of lentils: Ascochyta disease (Ascochyta lentis); Chickpea diseases: Ascochyta rabiei (blight of the chickpea plant) Diseases of green peppers: Anthracnose (Colletotrichum scovillei) , Powdery mildew (Leveillula taurica) , White mold (Sclerotium rolfsii) ; Mango diseases: Anthracnose (Colletotrichum acutatum); Diseases of cocoa: witches' broom disease (Moniliophthora perniciosa), pod rot (Moniliophthora roreri); Diseases of thin-shelled pecans: Black spot disease (Venturia effusa). Diseases of litchi: downy mildew (Peronophythora litchii) and anthracnose (Colletotrichum siemense). Fruit tree diseases: White root rot (Rosellinia necatrix) and Purple root rot (Helicobasidium mompa)); Post-harvest diseases of fruits such as apples and pears: Mucor rot diseases (Mucorpiriformis); Seed diseases or diseases in the early stages of growth caused by fungi such as Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thieviopsis, Rhizopus, Mucor, Corticium, Phona, Rhizoctonia, and Diplodia; Viral diseases: Giant vein disease of lettuce mediated by Olpidium brassicae; and various viral diseases of crops mediated by Polymyxa species (such as Polymyxa betae and Polymyxa graminis). Diseases caused by bacteria: Rice bacterial damping-off (Burkholderia plantarii), rice inner glume browning (Pantoea ananatis), rice bacterial leaf blight (Xanthomonas oryzae pv. oryzae.), cucumber bacterial angular leaf spot (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker (Xanthomonas citri), Chinese cabbage soft rot (Erwinia carotovora), potato scab (Streptomyces cabbiei), potato black shank (Pectobacterium soft rot). Bacterial leaf spot of peach (Pseudomonas syringae, Erwinianigrifluens, Xanthomonas campestris)), bacterial canker of plum (Pseudomonas syringae pv. morsprunorum, Erwinia sp.)), corn wilt (Clavibacter michiganensis), crown gall of grape, olive, peach, etc. (Xylella fastidiosa)), root nodule of Rosaceae plants such as apple, peach, cherry, etc. (Agrobacterium tumefaciens)

[0715] The soybean rust fungus with the F129L amino acid substitution in the mitochondrial cytochrome b protein is the following soybean rust fungus (scientific name: Phakopsora pachyrhizi): It has a mutation in the mitochondrial cytochrome b gene that encodes the mitochondrial cytochrome protein. As a result of this mutation, the F129L amino acid substitution has occurred, thereby showing resistance to QoI fungicide.

[0716] 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 the soil in which soybeans are cultivated with the present compound.

[0717] As a method for controlling plant diseases according to the present invention, it can be implemented by treating the plant or the soil of cultivated plants with an effective amount of the present invention compound, the present invention compound, or composition A. Examples of treatment methods include foliar treatment, soil treatment, and seed treatment.

[0718] With respect to this compound, the compound of the present invention, or composition A, it is generally mixed with inactive carriers such as solid carriers and liquid carriers, and surfactants, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate it into aqueous suspensions, oil suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, water-dispersible granules, powders, granules, etc. It is not limited to these formulations and can be formulated into the formulations described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.

[0719] These formulations typically contain 0.0001 to 99% of the present compound, the compound of the present invention, or composition A by weight.

[0720] Examples of solid carriers include clay (pyrophyllite clay, kaolinite clay, etc.), talc, calcium carbonate, diatomite, zeolite, bentonite, acid clay, palygorskite, silica, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) in powder and granular form, as well as resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0721] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxyl ethane, 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-dimethyloctylamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0722] Examples of surfactants 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.).

[0723] Examples of adjuvants for other formulations include binders, dispersants, colorants, and stabilizers. Specifically, examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginate, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), isopropyl phosphate, and butylated hydroxytoluene. Furthermore, adjuvants can be used as components to enhance or assist the efficacy of this compound, the compound of the present invention, or composition A. Specifically, examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (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), among others.

[0724] In this invention, "plant" includes the plant as a whole and specific parts of the plant. Examples of specific parts of a plant include, for example, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0725] Vegetative reproductive organs refer to the parts of a plant, such as roots, stems, and leaves, that have the ability to grow when separated from the main body and placed in the soil. Examples of vegetative reproductive organs include tuberous roots, creeping roots, bulbs, corms (or solid bulbs), tubers, rhizomes, stolons, rhizophores, cane cuttings, propagules, and vine cuttings. 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 shoots (a general term for leaves and stems, without roots) of plants such as sweet potatoes and Japanese yam. Bulbs, corms, tubers, rhizomes, stem cuttings, rootstocks, or tuberous roots are collectively referred to as bulbs. The cultivation of tubers begins by planting tubers into the soil, but the tubers used are usually called seed tubers.

[0726] Seedlings include seedlings and saplings.

[0727] As a method for controlling plant diseases by applying an effective amount of the present invention, its compound, or composition A to the soil, examples include applying an effective amount of the present invention, its compound, or composition A to the soil before or after transplanting. More specifically, examples include planting hole treatment (planting hole distribution, planting hole treatment soil mixing), root treatment (root distribution, root soil mixing, root irrigation, late seedling stage root treatment), planting furrow treatment (planting furrow distribution, planting furrow soil mixing), ridge furrow treatment (ridge furrow distribution, ridge furrow soil mixing, growing season ridge furrow distribution), sowing furrow treatment (sowing season ridge furrow distribution, sowing season ridge furrow soil mixing), comprehensive treatment (whole soil distribution, whole soil mixing), ridge planting lateral treatment, water surface treatment (water surface application, water surface application after water storage), other soil distribution treatments (growing season granule foliar distribution, distribution under the canopy or around the trunk, soil surface distribution, soil surface mixing, sowing hole distribution, ridge surface distribution). Distribute, interplant distribution), other irrigation treatments (soil irrigation, seedling irrigation, pesticide injection, basal irrigation, drip irrigation, chemical solution irrigation), seedling box treatment (seedling box distribution, seedling box irrigation, seedling box pesticide accumulation), seedling tray treatment (seedling tray distribution, seedling tray irrigation, seedling tray pesticide accumulation), seedbed treatment (seedbed distribution, seedbed irrigation, seedling bed distribution, seedling soaking), bed soil mixing treatment (bed soil mixing, pre-sowing bed soil mixing, distribution before sowing and covering with soil, distribution after sowing and covering with soil, soil mixing), and other treatments (cultivated soil mixing, turning in, topsoil mixing, rainwater drip soil mixing, planting location treatment, granular calyx distribution, paste fertilizer mixing).

[0728] Examples of seed treatment include treatments of seeds or vegetative reproductive organs by means of this compound, the compound of the present invention, or composition A. More specifically, examples include: spraying treatment by atomizing a suspension of this compound, the compound of the present invention, or composition A and spraying it onto the surface of the seed or vegetative reproductive organ; coating treatment by applying this compound, the compound of the present invention, or composition A onto the seed or vegetative reproductive organ; immersion treatment by immersing the seed or vegetative reproductive organ in a solution of this compound, the compound of the present invention, or composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs using a carrier containing this compound, the compound of the present invention, or composition A (coating treatment, granule coating treatment, etc.). Seed potatoes are a particularly good example of the aforementioned vegetative reproductive organ.

[0729] In this invention, "seeds or vegetative reproductive organs retaining this compound, or compound A of this invention, refer to seeds or vegetative reproductive organs in a state where this compound, or compound A of this invention, is attached to the surface of the seed or vegetative reproductive organ. For the aforementioned seeds or vegetative reproductive organs retaining this compound, or compound A of this invention, other materials besides this compound, or composition A may be attached before or after attaching this compound, or compound A of this invention, to the seed or vegetative reproductive organ.

[0730] Furthermore, when composition A adheres to the surface of a seed or vegetative reproductive organ by forming a layer, this layer is formed of one or more layers. Additionally, when multiple layers are formed, each layer may contain one or more active ingredients, or it may be formed of a layer containing one or more active ingredients and a layer not containing any active ingredient.

[0731] Seeds or vegetative reproductive organs containing this compound, the compound of the present invention, or composition A can be obtained, for example, by applying a preparation containing this compound, the compound of the present invention, or composition A to the seeds or vegetative reproductive organs using the aforementioned seed treatment method.

[0732] Although the application rate of this compound, the compound of the present invention, or composition A varies depending on meteorological conditions, formulation form, application time, application method, application location, target disease, target crop, etc., in the case of foliar or soil treatment, per 1000m 2 Typically, the dosage is 1 to 500 g. In the case of seed treatment, the amount of this compound, the compound of the present invention, or composition A is typically 0.001 to 100 g relative to 1 kg of seeds. When this compound, the compound of the present invention, or composition A is formulated into emulsions, wettable powders, aqueous suspensions, etc., it is usually applied by diluting with water to a concentration of 0.01 to 10,000 ppm of active ingredient. Powders, granules, etc., are usually applied directly.

[0733] This compound, or the compound or composition A of this invention, can be used as a control agent for plant diseases in farmland such as dry fields, paddy fields, lawns, and orchards. Examples of plants include the following.

[0734] Maize (dent, flint, soft, popcorn, glutinous, sweet, non-sweet maize), Rice (long-grain, short-grain, medium-grain, Japanese (japonica), tropical Japanese, Indian (indica), Javanese, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), Wheat (bread wheat (dull, soft, medium, red, white), durum wheat, spelt wheat, dense-eared wheat, each winter wheat type, spring wheat type), Barley (two-row barley (=brewing barley), six-row barley, naked barley, sticky barley, each...) Winter barley type, spring barley type), rye (winter rye type, spring rye type), black wheat (winter black wheat type, spring black wheat type), oats (winter oat type, spring oat type), sorghum, cotton (land-grown variety, Pima variety), soybean (mature seed harvest variety, edamame variety, green-harvested variety, each with indeterminate, determinate, and semi-determinate growth types), peanut, buckwheat, sugar beet (for sugar production, feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), Canada rapeseed (winter Canada rapeseed type, spring Canada rapeseed type), sunflower (for oil extraction, food). Vegetables used for both medicinal and ornamental purposes include sugarcane, tobacco, tea trees, mulberries, nightshade vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, cantaloupe, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, bok choy, mustard greens, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, chrysanthemum, artichoke, lettuce, etc.), lilyaceous vegetables (scallions, onions, garlic, asparagus, etc.), umbelliferous vegetables (carrots, parsley, celery, parsnips, etc.), chenopodiaceae vegetables (spinach, sauvignon Blanc, etc.), and lamiaceae vegetables (perilla, mint). Basil, strawberries, sweet potatoes, Japanese yam, taro, pears (apples, European pears, Japanese pears, white pears, quince, quince, etc.), stone fruits (peach, plum, nectarine, green plum, cherry, apricot, plum, etc.), citrus fruits (Wenzhou mandarin oranges, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants, turfgrass, and pasture grasses.

[0735] The above-mentioned plants are any commonly cultivated varieties, without any particular limitation. These plants also include plants produced through natural mating, plants produced through mutation, F1 hybrids, and recombinant crops. Examples of recombinant crops include, for instance, plants conferred resistance to herbicides such as isoxaflutole (HPPD inhibitors, imidazoline, ALS inhibitors, thifensulfuron-methyl inhibitors, EPSP inhibitors, glutamine synthase inhibitors, PPO inhibitors, bromobenzonitrile, or dicamba; plants capable of synthesizing known selective toxins from Bacillus species such as Bacillus thuringiensis; and plants conferred specific insecticidal activity by synthesizing gene fragments identical to endogenous genes from harmful insects and inducing gene silencing (RNAi; RNA interference) in target harmful insects.

[0736] Example The following examples, including manufacturing examples, reference manufacturing examples, formulation examples, and test examples, illustrate the present invention in more detail, but the present invention is not limited to these examples.

[0737] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, cPr represents cyclopropyl, Bu represents butyl, i-Bu represents isobutyl, s-Bu represents sec-butyl, Ph represents phenyl, and Bn represents benzyl. When Ph is substituted, the substituent and its position are listed before the symbol. For example, 4-OMe-Ph represents 4-methoxyphenyl, and 2,6-Cl2-Ph represents 2,6-dichlorophenyl.

[0738] When the physical properties of a compound are determined using liquid chromatography / mass spectrometry (hereinafter referred to as LC / MS), the measured molecular ion value [M+H] is recorded. + [M+H+MeCN] + Or [MH] - Retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0739] [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (General Incorporated Chemical Substances Evaluation and Research Organization). UV measurement wavelength: 254nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pumps: 2 units of LC-20AD (manufactured by Shimadzu Corporation) (high pressure gradient) Gradient conditions: The solution is delivered using the concentration gradient described in [Table LC1].

[0740] [Table 1] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) Ionization methods: DUIS method (ESI, APCI) First, examples of manufacturing this compound (including the compound of the present invention) are shown.

[0741] Manufacturing Example 1 Under a nitrogen atmosphere at 0°C, 6.3 mL of isopropyl magnesium chloride-lithium chloride complex (THF solution, 1.3 M) was added dropwise to a mixture of 2 g of 4-bromo-3,5-difluoro-1,1'-biphenyl and 18 mL of THF, and the mixture was stirred at room temperature for 2 hours. 6 mL of the resulting solution was added to 5 mL of a THF solution containing 0.22 g of 1,3-oxazol-2-carboxaldehyde, and the mixture was stirred at room temperature for 2.5 hours. An aqueous solution of ammonium chloride was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1 to 1:19) to give 0.41 g of compound 1 as shown below.

[0742] [Chemical Formula 73] Compound 1: 1 H-NMR (CDCl3) δ: 7.67 (1H, s), 7.55-7.52 (2H, m), 7.49-7.39(3H, m), 7.20-7.13 (3H, m), 6.26 (1H, d), 3.75-3.63 (1H, m). Manufacturing Example 1-1 The following shows the compounds manufactured according to Manufacturing Example 1 and their physical properties.

[0743] Formula (IA-1) [Chemical Formula 74] In the compound shown (hereinafter referred to as compound (IA-1)), R 1a R 2a X 1a X 2a X 3a X4a R 5A R 5B R 5C R 5D The combination of E is any combination of compounds listed in [Table A-1].

[0744] [Table 2] Compound 2: 1 H-NMR (CDCl3) δ: 8.79-8.76 (1H, m), 7.54-7.49 (2H, m), 7.46-7.36 (3H, m), 7.34 (1H, s), 7.15-7.11 (2H, m), 6.38 (1H, d), 3.84-3.54(1H, m). Compound 3: 1 H-NMR (CDCl3) δ: 7.74-7.73 (1H, m), 7.56-7.50 (2H, m), 7.48-7.33 (4H, m), 7.19-7.10 (2H, m), 6.43 (1H, d), 4.03-3.90 (1H, m). Compound 51: 1 H-NMR (CDCl3) δ: 7.43-7.33 (2H, m), 7.31 (1H, d), 7.25-7.09 (4H, m), 6.27 (1H, d), 6.20 (1H, d), 3.89 (3H, s), 3.20 (1H, d). Manufacturing Example 2 At room temperature, 0.30 g of a mixture of compound 1 and 5 mL of THF was added to 0.30 mL of phosphorus tribromide, and the mixture was stirred under reflux for 3 hours. A 1 M aqueous sodium hydroxide solution was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.2 g of compound 4 as shown below.

[0745] [Chemical Formula 75] Compound 4: 1H-NMR (CDCl3) δ: 7.59 (1H, d), 7.56-7.52 (2H, m), 7.48-7.36(3H, m), 7.21-7.13 (2H, m), 7.05 (1H, d), 4.22 (2H, s). Manufacturing Example 2-1 The following shows the compounds manufactured according to Manufacturing Example 2 and their physical properties.

[0746] In compound (IA-1), R 1a R 2a X 1a X 2a X 3a X 4a R 5A R 5B R 5C R 5D The combination of E is any combination of compounds listed in [Table A-2].

[0747] [Table 3] Compound 6: LC / MS: 288 [M+H] + RT = 2.083 minutes Manufacturing Example 3 At room temperature, 0.15 g of Dysmart oxidant was added to a mixture of 0.067 g of compound 1 and 5 mL of chloroform, and the mixture was stirred at room temperature for 4 hours. Then, 5 mL of saturated sodium thiosulfate aqueous solution and 5 mL of saturated sodium bicarbonate aqueous solution were added sequentially to the resulting mixture, and after stirring for 1 hour, extraction was performed using chloroform. The resulting organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.041 g of compound 7 as shown below.

[0748] [Chemical Formula 76] Compound 7: 1 H-NMR (CDCl3) δ: 7.94 (1H, s), 7.61-7.56 (2H, m), 7.52-7.42 (4H, m), 7.28-7.22 (2H, m). Manufacturing Example 4 Under a nitrogen atmosphere, a mixture of 0.43 g of intermediate 1,2,4-difluorophenylboronic acid, 0.27 g of {1,1'-bis(diphenylphosphino)ferrocene} palladium(II) dichloride, 0.60 g of tripotassium phosphate, 5 mL of DME, and 1 mL of water was stirred under reflux for 5 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.41 g of compound 8 as shown below.

[0749] [Chemical Formula 77] Compound 8: 1 H-NMR (CDCl3) δ: 7.56 (1H, d), 7.53 (2H, s), 7.47 (1H, d), 7.42-7.34 (1H, m), 7.00-6.91 (2H, m), 6.26 (1H, t), 5.66 (2H, s). Manufacturing Example 4-1 The following shows the compounds manufactured according to Manufacturing Example 4 and their physical properties.

[0750] In compound (IA-1), R 1a R 2a X 1a X 2a X 3a X 4a R 5A R 5B R 5C R 5D The combination of E is any combination of compounds listed in [Table A-3].

[0751] [Table 4] Compound 9: 1 H-NMR (CDCl3) δ: 7.52 (2H, dd), 7.47-7.42 (2H, m), 7.29-7.24 (2H, m), 7.19-7.11 (2H, m), 6.25 (1H, t), 5.42 (2H, s), 2.63 (2H, t),1.72-1.62 (2H, m), 0.96 (3H, t). Compound 10: 1H-NMR (CDCl3) δ: 7.55-7.50 (4H, m), 7.48-7.37 (3H, m), 7.20-7.13 (2H, m), 6.26 (1H, t), 5.43 (2H, s). Compound 11: 1 H-NMR (CDCl3) δ: 7.58-7.48 (4H, m), 7.46-7.41 (2H, m), 7.40-7.28 (3H, m), 7.21 (1H, t), 6.30 (1H, t), 5.41 (2H, s). Compound 12: 1 H-NMR (CDCl3) δ: 7.57 (1H, t), 7.50 (1H, d), 7.30-7.19(3H, m), 7.09-7.02 (2H, m), 6.85-6.78 (1H, m), 6.31 (1H, t), 5.42 (2H, s). Compound 13: 1 H-NMR (CDCl3) δ: 7.61-7.54 (3H, m), 7.47-7.39 (4H, m), 7.38-7.31 (2H, m), 7.10 (1H, d), 6.28 (1H, t), 5.37 (2H, s), 2.34 (3H, s). Compound 14: 1 H-NMR (CDCl3) δ: 7.59-7.54 (3H, m), 7.49-7.40 (3H, m), 7.39-7.33 (1H, m), 7.15-7.07 (3H, m), 6.27 (1H, t), 5.38 (2H, s), 3.92 (3H,s). Compound 15: 1 H-NMR (CDCl3) δ: 7.59 (2H, s), 7.56-7.52 (3H, m), 7.49-7.37 (4H, m), 6.25 (1H, t), 5.66 (2H, s). Compound 16: 1H-NMR (CDCl3) δ: 7.85 (1H, d), 7.80 (1H, d), 7.47 (1H, d), 7.45-7.35 (3H, m), 7.20 (1H, d), 7.00-6.90 (2H, m), 6.47 (1H, t), 6.16 (1H,t), 5.47 (2H, d). Compound 17: 1 H-NMR (CDCl3) δ: 7.56 (3H, d), 7.44-7.39 (3H, m), 7.27(2H, d), 6.25-6.24 (1H, m), 5.65 (2H, s), 2.41 (3H, s). Compound 37: 1 H-NMR (CDCl3) δ: 7.88 (1H, d), 7.76 (1H, dd), 7.60 (2H,dd), 7.54-7.52 (2H, m), 7.49-7.45 (2H, m), 7.43-7.39 (1H, m), 7.31 (1H, d),6.34 (1H, t), 5.57 (2H, s). Compound 38: 1 H-NMR (CDCl3) δ: 7.87 (1H, br s), 7.73 (1H, dt), 7.61 (2H,t), 7.40-7.39 (1H, m), 7.37-7.36 (1H, m), 7.29 (1H, d), 7.24-7.22 (1H, m),7.19-7.16 (1H, m), 6.35 (1H, t), 5.58 (2H, s). Compound 41: 1 H-NMR (CDCl3) δ: 7.64 (2H, s), 7.24-7.15 (5H, m), 5.75 (2H, s). Compound 4...

Claims

1. A method for controlling plant diseases, which is implemented by treating the plant or the soil of cultivated plants with a compound of formula (I) or its N oxide or salts. [Chemical Formula 1] In formula (I), Ring A 5 This indicates a 5-membered non-aromatic nitrogen-containing heterocycle, or a 5-membered aromatic nitrogen-containing heterocycle (wherein, Ring A 5 In this context, the atom bonded to D is either a carbon atom or a nitrogen atom, and the atom adjacent to the atom bonded to D forms a ring A. 5 (At least one of the atoms is a nitrogen atom). D indicates CR 1 R 2 C=O, C=S, or C=N-OR 7 , n represents 0, 1, 2, or 3. m represents 0, 1, 2, or 3. q represents 0, 1, 2, 3, 4, or 5. R 1 and R 2 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, a phenyl group, a 5 membered aromatic heterocyclic group {the phenyl group and the 5 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 8 SR 9 S(O)R 10 S(O)2R 11 NR 12 R 13 C(O)R 14 C(R) 15 =NOR 16 cyano, nitro, halogen atom or hydrogen atom R 1 and R 2 They can form C3-C8 alicyclic hydrocarbons or 3-8 membered non-aromatic heterocycles together with the carbon atoms they are bonded to {the C3-C8 alicyclic hydrocarbons and the 3-8 membered non-aromatic heterocycles can be substituted by one or more substituents selected from group B}. R 3 and R 5 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or a 3-8 membered non-aromatic heterocyclic group that can be substituted by one or more substituents selected from group A {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, or a 5-6 membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group C, OR 17 SR 18 S(O)R 19 S(O)2R 20 NR 21 R 22 C(O)R 23 C(R) 24 =NOR 25 cyano, nitro, or halogen atoms R 4 This indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 cyano, nitro, or halogen atoms R 6 This indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group D}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 32 SR 33 S(O)R 34 S(O)2R 35 NR 36 R 37 C(O)R 38 C(R) 39 =NOR 40 cyano, nitro, or halogen atoms R 8 R 12 R 13 R 17 R 21 R 22 R 26 R 27 R 28 R 32 R 36 and R 37 "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, or (C2-C8 dialkylamino)carbonyl group that can be substituted by one or more substituents selected from group A. The carbonyl group, and the (C2-C8 dialkylamino) carbonyl group may be substituted by one or more halogen atoms; C3-C8 alicyclic hydrocarbon group; 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted by one or more substituents selected from group B}; phenyl group; 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from group C}; or hydrogen atom. R 7 R 9 R 16 R 18 R 25 R 31 R 33 and R 40 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or a hydrogen atom. R 10 R 11 R 19 R 20 R 34 and R 35 This indicates a C1-C6 chain hydrocarbon group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {where the C1-C6 alkylamino group and the C2-C8 dialkylamino group can be substituted by one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group B}, or a phenyl or 5-6 membered aromatic heterocyclic group {where the phenyl or the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}. R 14 R 23 R 29 and R 38 The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxyl group. R 15 R 24 R 30 and R 39 "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more substituents selected from group A. When q is 2, 3, 4, or 5, two adjacent R 6 and R 6 They can form C5-C6 alicyclic hydrocarbons, 5-6 membered non-aromatic heterocycles {where the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle can be substituted by one or more substituents selected from group B}, benzene rings, or 5-6 membered aromatic heterocycles {where the benzene ring and the 5-6 membered aromatic heterocycle can be substituted by one or more substituents selected from group C} together with the carbon atoms they are bonded to. Group A: The group consisting of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted by one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted by one or more substituents selected from Group B}, phenyl groups, 5-6 membered aromatic heterocyclic groups {where the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group C}, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups. Group B: The group consisting of oxo groups, thio groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms, and cyano groups. Group C: Composed of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups, (C1-C6 alkyl)carbonylamino groups, (C1-C6 alkoxy)carbonylamino groups {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C...} The group consisting of 6-alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 alkylamino, C2-C8 dialkylamino, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, (C1-C6 alkylamino)carbonyl, (C2-C8 dialkylamino)carbonyl, (C1-C6 alkyl)carbonylamino, and (C1-C6 alkoxy)carbonylamino, wherein one or more halogen atoms may be substituted; and C3-C8 alicyclic hydrocarbon groups, amino, nitro, cyano, hydroxyl, thioalkyl, and halogen atoms that may be substituted by one or more substituents selected from group B. Group D: The group consisting of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted by one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be substituted by one or more substituents selected from Group B}, phenyl groups, 5 membered aromatic heterocyclic groups {where the phenyl group and the 5 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group C}, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups. (Among them, not) Including the following compounds: 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)difluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole-2(3H)-one, 2-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole, (3,5-Difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl) methyl ketone, 2-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-oxadiazole, (E)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, (Z)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-ethyl-1,2,4-thiadiazole, 5-Cyclopropyl-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-(trifluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxynitrile, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazol-5(4H)-one, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-ol, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-methoxy-1,2,4-thiadiazole, (2-chlorothiazol-4-yl)(3-fluoro-[1,1'-biphenyl]-4-yl)methanol, 2-Chloro-4-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)thiazole, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 5-Bromo-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxamide, and...

2. The plant disease control method as described in claim 1, wherein, The compound shown in formula (I), or its N oxide or salt, is a cyclic A 5 Compounds of the formula H1, H2, H3 or H4, or their N oxides or salts, [Chemical Formula 2] In the formula, # represents the bonding site with D. X 1 Represents nitrogen atom or CR a4 X 2 Represents nitrogen atom or CR b4 X 3 Represents nitrogen atom or CR c4 (where X) 1 X 2 and X 3 (The number of nitrogen atoms is 0 or 1). Q 1 X 4 and X 5 Combinatorial representation: X 4 For nitrogen atoms, Q 1 For NR a1 X 5 For CR d4 A combination; or, X 4 For CR e4 Q 1 For oxygen atoms, sulfur atoms, or NR b1 X 5 Nitrogen atom or CR f4 The combination Q 2 Represents oxygen atom or NR c1 X 7 Represents nitrogen atom or CR g4 , Q 3 Represents sulfur atoms or NR d1 , R a4 R b4 R c4 R d4 R e4 R f4 R g4 R h4 R i4 and R j4 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or an OR group. 26 NR 27 R 28 C(O)R 29 C(R) 30 =NOR 31 cyano, nitro, halogen atom or hydrogen atom R a1 R b1 R c1 and R d1 "Same" or "different from each other" indicates a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be substituted by one or more substituents selected from group A}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group can be substituted by one or more substituents selected from group C}, or a C(O)R group. 29 Or hydrogen atoms.

3. The plant disease control method as described in claim 2, wherein, The compound shown in formula (I), or its N oxide or salt, is a cyclic A 5 Compounds of which are represented by the group H1, or their N oxides or salts.

4. The plant disease control method as described in claim 2, wherein, The compound shown in formula (I), or its N oxide or salt, is a cyclic A 5 Compounds of which are represented by the group H2, or their N oxides or salts.

5. The plant disease control method as described in claim 2, wherein, The compound shown in formula (I), or its N oxide or salt, is a cyclic A 5 Compounds of which are represented by the group H3 or their N oxides or salts.

6. The plant disease control method as described in claim 2, wherein, The compound shown in formula (I), or its N oxide or salt, is a cyclic A 5 Compounds of which are represented by the group H4, or their N oxides or salts.

7. The compound shown in formula (II) or its N oxide or salt thereof, [Chemical Formula 3] In formula (II), Ring A 5a This indicates a 5-membered aromatic nitrogen-containing heterocycle (where, Ring A 5a In the middle, with CR 1a R 2a The bonded atoms are carbon or nitrogen atoms, and, with CR 1a R 2a The bonded atoms are adjacent and form a ring A 5a (At least one of the atoms is a nitrogen atom). na represents 0, 1, 2, or 3. ma represents 0, 1, 2, or 3. qa represents 0, 1, 2, 3, 4, or 5. R 1a and R 2a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a phenyl groups with one or more substituents, OR 8a SR 9a S(O)R 10a S(O)2R 11a NR 12a R 13a C(O)R 14a C(R) 15a =NOR 16a cyano, nitro, halogen atom or hydrogen atom R 1a and R 2a They can form C3-C8 alicyclic hydrocarbons or 3-8 membered non-aromatic heterocycles together with the carbon atoms they are bonded to {the C3-C8 alicyclic hydrocarbons and the 3-8 membered non-aromatic heterocycles can be selected from group B} a Substitution of one or more substituents in the middle. R 3a and R 5a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can be substituted, and the substituents can be selected from group C. a 5-6 membered aromatic heterocyclic groups substituted with one or more substituents, OR 17a SR 18a S(O)R 19a S(O)2R 20a NR 21a R 22a C(O)R 23a C(R) 24a =NOR 25a cyano, nitro, or halogen atoms R 4a This indicates that it can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in OR 26a NR 27a R 28a C(R) 29a =NOR 30a cyano, nitro, or halogen atoms R 6a Indicates that it can be selected from group E a A C1-C6 chain hydrocarbon group substituted with one or more substituents, which can be selected from group B a The C3-C8 alicyclic hydrocarbon group, phenyl group, or 5-6 membered aromatic heterocyclic group substituted with one or more substituents {the phenyl group and the 5-6 membered aromatic heterocyclic group can be selected from group C} a Substitution of one or more substituents in OR 31a SR 32a S(O)R 33a S(O)2R 34a NR 35a R 36a C(O)R 37a C(R) 38a =NOR 39a cyano, nitro, or halogen atoms R 8a R 12a R 13a R 17a R 31a R 21a R 22a and R 35a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group { phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group C} a One or more substituents in the group, or hydrogen atoms, R 36a This indicates that it can be selected from group A. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 7a R 9a R 10a R 18a R 19a R 25a R 32a R 33a R 34a and R 39a The same or different from each other indicates that they can be selected from group A. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 11a and R 20a The same or different from each other indicates that they can be selected from group A. a The following are included: C1-C6 chain hydrocarbon groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups {where the C1-C6 alkylamino group and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon groups, and 3-8 membered non-aromatic heterocyclic groups {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a One or more substituents are included in the group; phenyl or 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be selected from group C}. a Substitution of one or more substituents in the middle. R 14a and R 23a The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, or a hydroxyl group. R 15a R 24a and R 38a The same or different from each other indicates that they can be selected from group A. a One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom are substituted. R 26a R 27a and R 28a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C1-C6 alkylsulfonyl group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group {where the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, and the (C2-C8 dialkylamino)carbonyl group can be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {where the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group, or hydrogen atoms, R 30a This indicates that it can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in the middle. R 29a This indicates that it can be selected from group D. a One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom are substituted. R 37a This indicates that a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylamino group, or a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}. Group A a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a One or more substituents in the group { phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group C} a The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups. Group B a The group consisting of oxo groups, thio groups, C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {where the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms, and cyano groups. Group C a Composed of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups, C1-C6 alkylamino groups, C2-C8 dialkylamino groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups, (C1-C6 alkyl)carbonylamino groups, (C1-C6 alkoxy)carbonylamino groups {the C1-C6 chain hydrocarbon group, the C1- The C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, the C2-C8 dialkylamino group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group, the (C2-C8 dialkylamino)carbonyl group, the (C1-C6 alkyl)carbonylamino group, and the (C1-C6 alkoxy)carbonylamino group may be substituted with one or more halogen atoms; and may be selected from group B. a The group consisting of C3-C8 alicyclic hydrocarbon groups, amino, nitro, cyano, hydroxyl, thioalkyl, and halogen atoms substituted with one or more substituents. Group D a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups. Group E a The group consists of C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B}. a The group consisting of one or more substituents, phenyl, 5-membered aromatic heterocyclic group, halogen atom, cyano, nitro, hydroxyl and thioalkyl groups, (Among them, not) Including the following compounds: 4-((3,4,5-tribromo-1H-pyrazol-1-yl)methyl)-[1,1'-biphenyl]-3-ol, 5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-3-methyl-1,2,4-oxadiazole, 3-(chloromethyl)-5-(1-(3-fluoro-[1,1'-biphenyl]-4-yl)ethyl)-1,2,4-oxadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)difluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole-2(3H)-one, 2-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-thiadiazole, (3,5-Difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl) methyl ketone, 2-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)-1,3,4-oxadiazole, (E)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, (Z)-(3,5-difluoro-[1,1'-biphenyl]-4-yl)(1,2,4-thiadiazol-3-yl)methyl ketone O-methyl oxime, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-ethyl-1,2,4-thiadiazole, 5-Cyclopropyl-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-(trifluoromethyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxynitrile, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazol-5(4H)-one, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)isoxazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-ol, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-5-methoxy-1,2,4-thiadiazole, (2-chlorothiazol-4-yl)(3-fluoro-[1,1'-biphenyl]-4-yl)methanol, 2-Chloro-4-((3-fluoro-[1,1'-biphenyl]-4-yl)methyl)thiazole, 5-Chloro-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 5-Bromo-3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole, 3-((3,5-difluoro-[1,1'-biphenyl]-4-yl)methyl)-1,2,4-thiadiazole-5-carboxamide, and...

8. The compound of claim 7 or its N oxide or salt thereof, wherein, Ring A 5a It is a group represented by the formula H1a, H2a, H3a or H4a. [Chemical Formula 4] [In the formula, #] a Indicates CR 1a R 2a The bonding site, X 1a Represents nitrogen atom or CR a4a X 2a Represents nitrogen atom or CR b4a X 3a Represents nitrogen atom or CR c4a (where X) 1a X 2a and X 3a (The number of nitrogen atoms is 0 or 1). Q 1a X 4a X 5a Combinatorial representation: X 4a For nitrogen atoms, Q 1a For NR a1a X 5a For CR d4a A combination; or, X 4a For CR e4a Q 1a For oxygen atoms, sulfur atoms, or NR b1a X 5a Nitrogen atom or CR f4a The combination Q 2a Represents oxygen atom or NR c1a X 7a Represents nitrogen atom or CR g4a , Q 3a Represents sulfur atoms or NR d1a , R a4a R b4a R c4a R d4a R e4a R f4a R g4a R h4a R i4a and R j4a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a Substitution of one or more substituents in OR 26a NR 27a R 28a C(R) 29a =NOR 30a cyano, nitro, halogen atom or hydrogen atom R a1a R b1a R c1a and R d1a The same or different from each other indicates that they can be selected from group D. a The C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, and 3-8 membered non-aromatic heterocyclic group substituted with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group can be selected from group B} a One or more substituents in the group can replace a cyano group or a hydrogen atom.

9. A composition comprising an inactive support and the compound of claim 7 or claim 8, or its N oxide or salt thereof.

10. A composition comprising one or more ingredients selected from the group consisting of (a), (b), (c), and (d), and the compound of claim 7 or claim 8, or its N oxide or salt thereof. Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients; Group (b): Bactericidal active ingredients; Group (c): Plant growth regulators; Group (d): Repellent component.

11. A method for controlling plant diseases, which is carried out by treating the soil of a plant or cultivated plant with an effective amount of the compound of claim 7 or claim 8 or its N oxide or salt thereof, or an effective amount of the composition of claim 10.

12. Use of the compound of claim 7 or claim 8, or its N oxide, or its salt, or the composition of claim 10, for the control of plant diseases.

13. A seed or vegetative reproductive organ containing an effective amount of the compound of claim 7 or claim 8 or its N oxide or salt thereof, or an effective amount of the composition of claim 10.

14. The compound shown in formula (III), [Chemical Formula 5] In formula (III), X n1 Represents halogen atoms, R n1 R n2 R n3 and R n5 The same or different from each other indicates hydrogen atom, halogen atom, methyl or methoxy atom. E n1 and R n4 Combinatorial representation: E n1 Halogen atoms, R n4 It is a combination of hydrogen atoms, methyl groups, or methoxy groups; or, E n1 It is a cyano group, C(O)OH, or C(NH2)=NOR n6 , R n4 It is a combination of hydrogen atoms, halogen atoms, methyl or methoxy groups. R n6 It represents a C1-C6 alkyl carbonyl group or a hydrogen atom that can be replaced by one or more halogen atoms.

15. The compound shown in formula (IV), [Chemical Formula 6] In equation (IV), R m1 Indicates a chlorine atom, bromine atom, or iodine atom. R m2 Represents halogen atoms, R m3 Indicates hydrogen atom, halogen atom, methyl or methoxy group, E m1 This indicates that 1,2,4-thiadiazole-3-yl, 1,2,4-oxadiazole-3-yl {the 1,2,4-thiadiazole-3-yl and the 1,2,4-oxadiazole-3-yl can be selected from group A} m1 Substitution of one or more substituents, 1,2,3-triazol-2-yl, or isothiazol-3-yl {the 1,2,3-triazol-2-yl and the isothiazol-3-yl may be selected from group B} m1 Substitution of one or more substituents in the middle. Group A m1 The group consisting of C1-C4 alkyl, C1-C4 alkoxy, cyclopropyl, and CF3 groups. Group B m1 The group consisting of halogen atoms, C1-C4 alkyl groups, C1-C4 alkoxy groups, C1-C4 haloalkyl groups, C1-C4 haloalkoxy groups, and cyclopropyl groups.

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