Plant disease control method

Abstract

The present invention provides a plant disease control method having an excellent control effect on plant diseases, which comprises using a compound represented by formula (I) (in the formula, n represents 0, 1, or 2, R1 represents a C1-C6 alkyl group or the like, R2 and R3 may be the same or different from each other and represent a C1-C6 chain hydrocarbon group or the like that may be substituted with one or more halogen atoms, R4 represents a C1-C6 chain hydrocarbon group or the like, q represents 1, 2, or 3, and in the case where q is 2 or 3, R1 represents a C1-C6 alkyl group or the like, R2 represents a C1-C6 chain hydrocarbon group or the like, and q represents a C1-C6 chain hydrocarbon group or the like. In the formula, two or three R4 may be the same or different, a combination of X1, X2, X3, and X4 represents a combination of X1 being CR5, X2 being CR6, X3 being CR7, and X4 being a nitrogen atom, or the like, and R5, R6, and R7 may be the same or different from each other, and each represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, or the like. ) A step for treating a plant or a soil in which a plant is cultivated with a compound represented by the formula, an N-oxide thereof, or a salt of the compound or the N-oxide. # imgabs0 #

Description

Technical Field

[0001] This patent application asserts priority and interests under the Paris Convention based on Japanese Patent Application No. 2022-098034 (filed on June 17, 2022) and Japanese Patent Application No. 2022-180831 (filed on November 11, 2022), the entire contents of which are incorporated herein by reference.

[0002] This invention relates to methods for the prevention and control of plant diseases. Background Technology

[0003] Patent document 1 describes a compound called biaromatic compound as a plant disease control agent.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Description of Chinese Patent Application Publication No. 101875639 Summary of the Invention

[0007] Problems to be solved by the invention

[0008] The objective of this invention is to provide a superior method for the prevention and control of plant diseases.

[0009] Methods for solving problems

[0010] 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.

[0011] That is, the present invention is as follows.

[0012] [1] A method for controlling plant diseases, which is carried out by treating the plant or the soil of cultivated plants with a compound of formula (I) (hereinafter referred to as compound X) or its N oxide or their salt (hereinafter referred to as compound Y).

[0013] [Chemical Formula 1]

[0014]

[0015] In the formula,

[0016] n represents 0, 1, or 2.

[0017] R 1This indicates C1-C6 alkyl, C2-C6 ynyl (the C1-C6 alkyl and C2-C6 ynyl may have one or more substituents selected from group A), C2-C6 alkenyl (may have one or more substituents selected from group C), C3-C8 alicyclic hydrocarbon, 3-8 membered non-aromatic heterocyclic (the C3-C8 alicyclic hydrocarbon and 3-8 membered non-aromatic heterocyclic may have one or more substituents selected from group B), C6-C10 aryl (may have one or more substituents selected from group F), 5-10 membered aromatic heterocyclic (may have one or more substituents selected from group D), or NR. 33 R 34 ,

[0018] R 2 and R 3 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, or OR 9 SR 10 S(O)R 11 、S(O)2R 12 NR 13 R 14 C(O)R 15 Nitro, cyano, halogen atom or hydrogen atom,

[0019] 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 may have 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 may have one or more substituents selected from group D), or an OR group that may have one or more substituents selected from group D. 16 SR 17 S(O)R 18 、S(O)2R 19 NR 20 R 21 C(O)R 22 C(R) 23 ) = NOR 24 Cyano, nitro, amino, hydroxyl or halogen atom

[0020] q represents 1, 2, or 3.

[0021] When q is 2 or 3, there are 2 or 3 R 4 They can be the same or different.

[0022] X 1 X 2 X 3and X 4 Combinatorial representation:

[0023] X 1 For CR 5 X 2 For CR 6 X 3 For CR 7 X 4 It is a combination of nitrogen atoms;

[0024] X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 The combination;

[0025] X 1 For CR 5 X 2 For nitrogen atoms, X 3 For CR 7A X 4 For CR 8 The combination;

[0026] X 1 For nitrogen atoms, X 2 For CR 6 X 3 For CR 7B X 4 For CR 8 The combination;

[0027] X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 For CR 7C X 4 A combination of CH;

[0028] X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 For CH, X 4 For CR 8 The combination;

[0029] X 1 For nitrogen atoms, X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 The combination;

[0030] X 1 For nitrogen atoms, X2 CR 6 X 3 CR 7 X 4 It is a combination of nitrogen atoms;

[0031] X 1 CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 CR 8 The combination;

[0032] X 1 CR 5 X 2 For nitrogen atoms, X 3 For CH, X 4 It is a combination of nitrogen atoms;

[0033] X 1 For CH, X 2 For nitrogen atoms, X 3 CR 7D X 4 A combination of nitrogen atoms; or, X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 A combination of nitrogen atoms,

[0034] R 5 R 6 R 7 and R 8 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, or OR 25 SR 26 S(O)R 27 、S(O)2R 28 NR 29 R 30 C(O)R 31 Nitro, cyano, halogen atom or hydrogen atom,

[0035] R 9 R 10 R 13 and R 29 "Identical" or "different" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more halogen atoms.

[0036] R 7ARepresents a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, OR 25 SR 26 S(O)R 27 、S(O)2R 28 NR 29 R 32 C(O)R 31 Nitro, cyano, halogen atom or hydrogen atom,

[0037] R 7B Represents a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, OR 25 NR 29 R 30 C(O)R 31 Nitro, cyano, halogen atom or hydrogen atom,

[0038] R 7C Represents a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, OR 25 NR 29 R 30 C(O)R 31 nitro, cyano, or halogen atoms

[0039] R 7D Represents a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group that may have one or more substituents selected from group B, OR 25 S(O)R 27 、S(O)2R 28 NR 29 R 30 C(O)R 31 Nitro, cyano, fluorine, chlorine, or iodine atoms

[0040] R 11 R 12 R 25 R 26 R 27 and R 28 The same or different from each other indicates C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom.

[0041] R 14 and R 30"Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group {where the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group can be substituted by one or more halogen atoms} or a hydrogen atom.

[0042] R 15 R 22 and R 31 The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, or C2-C8 dialkylamino group can be substituted with one or more halogen atoms.

[0043] R 16 This 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 having one or more substituents selected from group A. The carbonyl group (C2-C8 dialkylamino) may be substituted with 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 have 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 have one or more substituents selected from group D); or hydrogen atom.

[0044] R 17 R 18 R 19 and R 24 "Identical" or "different from each other" indicates that the following groups may have one or more substituents selected from group A: C1-C6 chain hydrocarbon group, 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 have one or more substituents selected from group B), phenyl or 5-6 membered aromatic heterocyclic group (the phenyl or the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D).

[0045] R 20The following groups may have one or more substituents selected from Group A: C1-C6 chain hydrocarbon group, 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 have 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 have one or more substituents selected from Group D), (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, or C1-C6 alkylsulfonyl group (the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms).

[0046] R 21 and R 23 "Identical" or "different from each other" indicates that the C1-C6 chain hydrocarbon group or hydrogen atom may have one or more substituents selected from group A.

[0047] R 32 This indicates a C1-C6 chain hydrocarbon group, (C1-C6 alkyl)carbonyl group, or (C1-C6 alkoxy)carbonyl group that can be substituted by one or more halogen atoms {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group can be substituted by one or more halogen atoms}.

[0048] R 33 and R 34 "Same" or "different" indicates that it may have a C1-C6 chain hydrocarbon group with one or more substituents selected from group G, a C3-C6 alicyclic hydrocarbon group with one or more halogen atoms, or a hydrogen atom.

[0049] Adjacent R 2 and R 4 They can form C5-C6 alicyclic hydrocarbons, 5-6 membered non-aromatic heterocycles (the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have one or more substituents selected from group B), benzene rings, or 5-6 membered aromatic heterocycles (the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E) together with the carbon atoms they are bonded to.

[0050] Two adjacent R 4 and R 4 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 may have 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 may have one or more substituents selected from group E) together with the carbon atoms they are bonded to.

[0051] Group A: Composed of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {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 {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 {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group D}, halogen atoms, cyano groups, nitro groups, hydroxyl groups and thioalkyl groups.

[0052] 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0053] Group C: Composed of C1-C6 alkoxy groups, C1-C6 alkylthioalkyl groups, C1-C6 alkylsulfinyl groups, C1-C6 alkylsulfonyl groups {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 {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 {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted by one or more substituents selected from Group D}, chlorine atoms, bromine atoms, iodine atoms, cyano groups, nitro groups, hydroxyl groups and thioalkyl groups.

[0054] Group D: 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- The group consisting of C6 alkyl sulfinyl, C1-C6 alkyl sulfonyl, 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 have one or more substituents selected from group B.

[0055] Group E: The group consisting of C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthioalkyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group {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 by one or more halogen atoms}, hydroxyl group, thioalkyl group, halogen atom and cyano group.

[0056] Group F: 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 The group consisting of a C1-C6 alkyl sulfinyl group, the C1-C6 alkyl sulfinyl group, the C1-C6 alkyl amino group, the C2-C8 dialkyl amino group, the (C1-C6 alkyl) carbonyl group, the (C1-C6 alkoxy) carbonyl group, the (C1-C6 alkyl amino) carbonyl group, the (C2-C8 dialkyl amino) carbonyl group, the (C1-C6 alkyl) carbonyl amino group, and the (C1-C6 alkoxy) carbonyl amino group, which may be substituted with one or more halogen atoms, and a C3-C8 alicyclic hydrocarbon group, an amino group, a cyano group, a hydroxyl group, a thioalkyl group, and a halogen atom that may have one or more substituents selected from group B.

[0057] Group G: The group consisting of C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 alkylthio groups (the C3-C6 cycloalkyl, C1-C3 alkoxy, and C1-C3 alkylthio groups may be substituted with one or more halogen atoms), halogen atoms, and cyano groups.

[0058] [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 R 1 A compound (hereinafter referred to as Compound N) is a C1-C6 alkyl, C2-C6 alkynyl (the C1-C6 alkyl and the C2-C6 alkynyl may have one or more substituents selected from Group A), a C2-C6 alkenyl chain (may have one or more substituents selected from Group C), or a C3-C8 alicyclic hydrocarbon (the C3-C8 alicyclic hydrocarbon may have one or more substituents selected from Group B) or its N oxide or salt thereof (hereinafter, Compound N or its N oxide or salt thereof is referred to as Compound N).

[0059] [3] The method as described in [2], wherein the compound represented by formula (I) or its N oxide or salt thereof is X 1 X 2 X 3 and X 4 The combination is a compound or its N oxide or salt thereof, which is one of the following combinations: X 1 CR 5 X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 CR 7A X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Combinations; X 1 For nitrogen atoms, X2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 CR 8 A combination; or, X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 It is a combination of nitrogen atoms.

[0060] [4] The method as described in [2] or [3], wherein the compound represented by formula (I) or its N oxide or salt thereof is R 1 It is a compound of C2-C6 alkyl, C2-C6 ynyl (the C2-C6 alkyl and the C2-C6 ynyl may have one or more substituents selected from group A), methyl with one or more substituents selected from group C, or C3-C8 alicyclic hydrocarbon (the C3-C8 alicyclic hydrocarbon may have one or more substituents selected from group B) or its N oxide or salt thereof.

[0061] [5] The compound shown in formula (II) (hereinafter referred to as compound D of the present invention) or its N oxide or salt thereof (hereinafter referred to as compound R of the present invention).

[0062] [Chemical Formula 2]

[0063]

[0064] In the formula,

[0065] na represents 0, 1, or 2.

[0066] qa represents 1, 2, or 3.

[0067] When qa is 2 or 3, there are 2 or 3 R's. 4a They can be the same or different.

[0068] R 1a This indicates C2-C6 alkyl and C2-C6 ynyl groups {the C2-C6 alkyl and C2-C6 ynyl groups may have components selected from group A} a One or more substituents in the group can have a number selected from group F. a The C2-C6 alkenyl group with one or more substituents may have a group selected from group B.a C3-C8 alicyclic hydrocarbon group with one or more substituents, having a group selected from the group C a The methyl group having one or more substituents, or having a group selected from group G a 5-6 membered aromatic heterocyclic groups with one or more substituents,

[0069] R 8a This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R 13a C(O)R 14a Nitro, cyano, halogen atom or hydrogen atom,

[0070] R 2a and R 3a "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 15a SR 16a S(O)R 17a 、S(O)2R 18a NR 19a R 20a C(O)R 21a Nitro, cyano, halogen atom or hydrogen atom,

[0071] X a R 4a and R 6a Combinatorial representation:

[0072] X a For nitrogen atoms,

[0073] R 4a To have selected from group A a C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a、S(O)2R 26a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Cyano, nitro, amino, hydroxyl or halogen atom

[0074] R 6a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R 13a C(O)R 14a A combination of nitro, cyano, halogen, or hydrogen atoms; or,

[0075] X a For CR 5a ,

[0076] R 4a To have selected from group F a The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. a C2-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a 、S(O)2R 22a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Cyano, nitro, amino, hydroxyl or halogen atom

[0077] R 6a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7aA combination of nitro, fluorine, bromine, iodine, or hydrogen atoms.

[0078] R 5a This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R 13a C(O)R 14a Nitro, cyano, halogen atom or hydrogen atom,

[0079] R 7a R 9a R 10a R 11a R 15a R 16a R 17a and R 18a The same or different from each other indicates C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom.

[0080] R 12a and R 19a "Identical" or "different" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more halogen atoms.

[0081] R 13a and R 20a "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group {where the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group can be substituted by one or more halogen atoms} or a hydrogen atom.

[0082] R 14a R 21a and R 29a The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, or C2-C8 dialkylamino group can be substituted with one or more halogen atoms.

[0083] R 23a This indicates that it can have elements selected from group A. aC1-C6 chain hydrocarbons, C1-C6 alkylsulfonyl groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups {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 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 can have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents or hydrogen atoms in it

[0084] R 22a R 24a R 25a and R 31a The same or different from each other indicates that they can be selected from group A. a C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a One or more substituents, phenyl or 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have elements selected from group D} a One or more substituents in the middle,

[0085] R 26a Indicates that it has a selection from group A a The methyl group with one or more substituents may have a group selected from group A. a C2-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a One or more substituents, phenyl or 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have elements selected from group D} a One or more substituents in the middle,

[0086] R 27a This indicates that it can have elements selected from group A. a C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} aThe phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a The following groups may contain one or more substituents: (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, or C1-C6 alkylsulfonyl (the (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms).

[0087] R 28a and R 30a The same or different from each other indicates that they can be selected from group A. a C1-C6 chain hydrocarbon groups or hydrogen atoms with one or more substituents.

[0088] Adjacent R 2a and R 4a They can form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocycles together with the carbon atoms they are bonded to. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a One or more substituents in the group, a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E} a One or more substituents in the middle,

[0089] Two adjacent R 4a and R 4a They can form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocycles together with the carbon atoms they are bonded to. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a One or more substituents in the group, a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E} a One or more substituents in it.

[0090] Group A a : Composed 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, 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 phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. a The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0091] 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 {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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0092] Group C a : Composed 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, 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 substance may contain one or more substituents, and a 5-6 membered aromatic heterocyclic group (which may be selected from group D). a A group consisting of one or more substituents in the group.

[0093] Group D 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 have a group 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 with one or more substituents.

[0094] Group E aThe group consisting of 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0095] Group F a : Composed 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, 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 phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. a The group consisting of one or more substituents, chlorine atoms, bromine atoms, iodine atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0096] Group G a The group consisting 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, and C2-C8 dialkylamino groups {where the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group, and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, and C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, thioalkyl groups, and halogen atoms that may have one or more substituents selected from group B.

[0097] [6] The compound as described in [5] (hereinafter referred to as compound N of the present invention) or its N oxide or salt thereof (hereinafter referred to as compound N of the present invention or its N oxide or salt thereof as compound of the present invention), wherein R 1a It is a C2-C6 alkyl or C2-C6 ynyl group {the C2-C6 alkyl and the C2-C6 ynyl group may have components selected from group A} a One or more substituents in the group can have a number selected from group F. a The C2-C6 alkenyl group with one or more substituents may have a group selected from group B. a C3-C8 alicyclic hydrocarbon group with one or more substituents, or having a group selected from C10 ...a A methyl group with one or more substituents.

[0098] [7] The compound as described in [6] or its N oxide or salt thereof, wherein X a For nitrogen atoms, R 4a To have the option to select from group A a C1-C6 chain hydrocarbon groups with one or more substituents, OR 23a NR 27a R 28a Cyano, nitro, hydroxyl or halogen atom.

[0099] [8] The compound as described in [6] or its N oxide or salt thereof, wherein X a For CR 5a , R 4a It is methyl, and may contain elements selected from group A. a C2-C6 chain hydrocarbon groups with one or more substituents, OR 23a SR 24a S(O)R 25a 、S(O)2R 22a NR 27a R 28a Cyano, nitro, hydroxyl or halogen atom.

[0100] [9] The compound or its N oxide or salt thereof as described in any one of [5] to [8], wherein R 6a It is a hydrogen atom.

[0101]

[10] The compound shown in formula (III) (hereinafter referred to as compound E of the present invention) or its N oxide or salt thereof (hereinafter referred to as compound S of the present invention).

[0102] [Chemical Formula 3]

[0103]

[0104] In the formula,

[0105] nb represents 0, 1, or 2.

[0106] qb represents 1, 2, or 3.

[0107] With qb = 2 or 3, there are 2 or 3 R's. 4b They can be the same or different.

[0108] R 1b It indicates that it can have selected from group G b phenyl groups with one or more substituents

[0109] R8b This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b SR 9b S(O)R 10b 、S(O)2R 11b NR 12b R 13b C(O)R 14b Nitro, cyano, halogen atom or hydrogen atom,

[0110] R 2b and R 3b "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 15b SR 16b S(O)R 17b 、S(O)2R 18b NR 19b R 20b C(O)R 21b Nitro, cyano, halogen atom or hydrogen atom,

[0111] X b R 4b and R 6b Combinatorial representation:

[0112] X b For nitrogen atoms,

[0113] R 4b To have selected from group F b The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. b C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents in OR 23b SR 24b S(O)R 25b 、S(O)2R 22b NR 27b R 28b C(O)R 29b C(R) 30b) = NOR 31b , cyano, nitro, hydroxyl, amino or halogen atom,

[0114] R 6b It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b SR 9b S(O)R 10b 、S(O)2R 11b NR 12b R 13b C(O)R 14b A combination of nitro, halogen, or hydrogen atoms; or,

[0115] X b CR 5b ,

[0116] R 4b To have selected from group F b The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. b C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents in OR 32b SR 24b S(O)R 25b 、S(O)2R 22b NR 27b R 28b C(O)R 29b C(R) 30b ) = NOR 31b cyano, nitro, hydroxyl or halogen atom

[0117] R 6b It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b A combination of nitro, fluorine, bromine, iodine, or hydrogen atoms.

[0118] R 5b This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. bC3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b SR 9b S(O)R 10b 、S(O)2R 11b NR 12b R 13b C(O)R 14b Nitro, cyano, halogen atom or hydrogen atom,

[0119] R 7b R 9b R 10b R 11b R 15b R 16b R 17b and R 18b The same or different from each other indicates C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom.

[0120] R 12b and R 19b "Identical" or "different" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more halogen atoms.

[0121] R 13b and R 20b "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group {where the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group can be substituted by one or more halogen atoms} or a hydrogen atom.

[0122] R 14b R 21b and R 29b The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, or C2-C8 dialkylamino group can be substituted with one or more halogen atoms.

[0123] R 23b This indicates that it can have elements selected from group A. bC1-C6 chain hydrocarbons, C1-C6 alkylsulfonyl groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups {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 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 can have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents or hydrogen atoms in it

[0124] R 22b R 24b R 25b and R 31b The same or different from each other indicates that they can be selected from group A. b C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b One or more substituents, phenyl or 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have elements selected from group D} b One or more substituents in the middle,

[0125] R 27b This indicates that it can have elements selected from group A. b C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b The following groups may contain one or more substituents: (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, or C1-C6 alkylsulfonyl (the (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms).

[0126] R 28b and R 30b The same or different from each other indicates that they can be selected from group A. b C1-C6 chain hydrocarbon groups or hydrogen atoms with one or more substituents.

[0127] R 32b Indicates that it has a selection from group A b The methyl group with one or more substituents may have a group selected from group A. b C2-C6 chain hydrocarbons, C1-C6 alkylsulfonyl groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups {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 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 can have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents or hydrogen atoms in it

[0128] Adjacent R 2b and R 4b They can form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocycles together with the carbon atoms they are bonded to. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) b One or more substituents in the group, a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E} b One or more substituents in the middle,

[0129] Two adjacent R 4b and R 4b They can form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocycles together with the carbon atoms they are bonded to. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) b One or more substituents in the group, a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E} b One or more substituents in it.

[0130] Group A b: Composed 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, 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) b The phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. b The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0131] Group B 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0132] Group D b 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 have a group selected from group B. b The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, thioalkyl groups, and halogen atoms with one or more substituents.

[0133] Group E bThe group consisting of 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0134] Group F b : Composed 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, 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) b The phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. b The group consisting of one or more substituents, chlorine atoms, bromine atoms, iodine atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0135] Group G b 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 have a group selected from group B. b The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, cyano groups, hydroxyl groups, thioalkyl groups, and halogen atoms with one or more substituents.

[0136]

[11] The compound shown in formula (IV) (hereinafter referred to as compound F of the present invention) or its N oxide or salt thereof (hereinafter referred to as compound T of the present invention).

[0137] [Chemical Formula 4]

[0138]

[0139] In the formula,

[0140] nc represents 0, 1, or 2.

[0141] qc represents 1, 2, or 3.

[0142] With qc = 2 or 3, there are 2 or 3 Rs. 4c They can be the same or different.

[0143] X c Represents nitrogen atom or CR 5c ,

[0144] R 1c This indicates that it may have a selection from group B. c 3-8 membered non-aromatic heterocyclic groups with one or more substituents, or NR 33c R 34c ,

[0145] R 8c This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. c C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7c SR 9c S(O)R 10c 、S(O)2R 11c NR 12c R 13c C(O)R 14c Nitro, cyano, halogen atom or hydrogen atom,

[0146] R 2c and R 3c "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. c C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 15c SR 16c S(O)R 17c 、S(O)2R 18c NR 19c R 20c C(O)R 21c Nitro, cyano, halogen atom or hydrogen atom,

[0147] R 4c To have selected from group A c C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} c One or more substituents in the group, 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D} c One or more substituents in OR 23c SR 24c S(O)R 25c 、S(O)2R 22c NR 27c R 28c C(O)R 29c C(R) 30c ) = NOR 31c Cyano, nitro, amino, hydroxyl or halogen atom

[0148] R 6c This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. c C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7c SR 9c S(O)R 10c 、S(O)2R 11c NR 12c R 13c C(O)R 14c Nitro, cyano, halogen atom or hydrogen atom,

[0149] R 5c This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. c C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7c SR 9c S(O)R 10c 、S(O)2R 11c NR 12c R 13c C(O)R 14c Nitro, cyano, halogen atom or hydrogen atom,

[0150] R 7c R 9c R 10c R 11c R 15c R 16c R 17c and R18c The same or different from each other indicates C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom.

[0151] R 12c and R 19c "Identical" or "different" indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more halogen atoms.

[0152] R 13c and R 20c "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group {where the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group can be substituted by one or more halogen atoms} or a hydrogen atom.

[0153] R 14c R 21c and R 29c The terms "same" or "different" indicate that the C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylamino group, or C2-C8 dialkylamino group can be substituted with one or more halogen atoms.

[0154] R 23c This indicates that it can have elements selected from group A. c C1-C6 chain hydrocarbons, C1-C6 alkylsulfonyl groups, (C1-C6 alkyl)carbonyl groups, (C1-C6 alkoxy)carbonyl groups, (C1-C6 alkylamino)carbonyl groups, (C2-C8 dialkylamino)carbonyl groups {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 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 can have elements selected from group B} c The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. c One or more substituents or hydrogen atoms in it

[0155] R 22c R 24c R 25c and R 31c The same or different from each other indicates that they can be selected from group A. cC1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} c One or more substituents, phenyl or 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have elements selected from group D} c One or more substituents in the middle,

[0156] R 27c This indicates that it can have elements selected from group A. c C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} c The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. c The following groups may contain one or more substituents: (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, or C1-C6 alkylsulfonyl (the (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl, and C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms).

[0157] R 28c and R 30c The same or different from each other indicates that they can be selected from group A. c C1-C6 chain hydrocarbon groups or hydrogen atoms with one or more substituents.

[0158] R 33c It indicates that it can have selected from group G c The C1-C6 chain hydrocarbon group with one or more substituents, or the C3-C6 cycloalkyl group or hydrogen atom that may have one or more halogen atoms.

[0159] R 34c It indicates that it can have selected from group G c C1-C6 chain hydrocarbon groups with one or more substituents, or C3-C6 cycloalkyl groups that may have one or more halogen atoms.

[0160] Adjacent R 2c and R 4c They can form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocycles together with the carbon atoms they are bonded to. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) c One or more substituents in the group, a benzene ring or a 5-6 membered aromatic heterocycle {the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E} c One or more substituents in the middle,

[0161] Two adjacent R 4c and R 4c They can form with the carbon atoms they are bonded to, which can have a composition selected from group B. c C5-C6 alicyclic hydrocarbons with one or more substituents, which may have C16 groups selected from the group C16 group C2 ...5 group C26 group C c A 5-6 membered non-aromatic heterocycle, benzene ring, or 5-6 membered aromatic heterocycle with one or more substituents (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). c One or more substituents in it.

[0162] Group A c : Composed 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, 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) c The phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. c The group consisting of one or more substituents, halogen atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0163] Group B c 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0164] Group C c The group consisting of thioyl, C1-C6 chain hydrocarbon, C1-C6 alkoxy, C1-C6 alkylthioalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl (the C1-C6 chain hydrocarbon, the C1-C6 alkoxy, the C1-C6 alkylthioalkyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted by one or more halogen atoms), hydroxyl, thioalkyl, halogen atom and cyano.

[0165] Group D cComposed 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 have a group selected from group B. c The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, thioalkyl groups, and halogen atoms with one or more substituents.

[0166] Group E c The group consisting of 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 by one or more halogen atoms}, hydroxyl groups, thioalkyl groups, halogen atoms and cyano groups.

[0167] Group F c : Composed 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, 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) c The phenyl group has one or more substituents, and the phenyl group or the 5-6 membered aromatic heterocyclic group can be selected from group D. c The group consisting of one or more substituents, chlorine atoms, bromine atoms, iodine atoms, cyano groups, nitro groups, hydroxyl groups, and thioalkyl groups.

[0168] Group G c[The group consisting of C3-C6 cycloalkyl, C1-C3 alkoxy, C1-C3 alkylthio groups (where the C3-C6 cycloalkyl, C1-C3 alkoxy, and C1-C3 alkylthio groups may be substituted with one or more halogen atoms), halogen atoms, and cyano groups.]

[0169]

[12] A pesticide composition comprising an inactive support and any one of the compounds described in [5] to

[11] , or their N oxides or salts.

[0170]

[13] A composition comprising one or more components selected from the groups (a), (b), (c) and (d), and any one of [5] to

[11] , or an N oxide thereof, or a salt thereof:

[0171] Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients;

[0172] Group (b): Bactericidal active ingredient;

[0173] Group (c): Plant growth regulators;

[0174] Group (d): Repellent component.

[0175]

[14] A method for controlling plant diseases, which is carried out by treating the soil of plants or cultivated plants with an effective amount of any one of the compounds of [5] to

[11] or their N oxides or salts or an effective amount of the composition of

[13] .

[0176] The use of any one of the compounds in

[15] , [5] to

[11] or their N oxides or salts thereof or the composition described in

[13] for the control of plant diseases.

[0177]

[16] A seed or vegetative reproductive organ that retains an effective amount of any one of [5] to

[11] or its N oxide or salt thereof or an effective amount of the composition described in

[13] .

[0178]

[17] The compound shown in formula (V) (hereinafter referred to as intermediate A).

[0179] [Chemical Formula 5]

[0180]

[0181] In the formula,

[0182] R 1d This indicates a C2-C4 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group, or a 5-6 membered aromatic heterocyclic group (the 5-6 membered aromatic heterocyclic group can be selected from group V). 1 One or more substituents in the middle are substituted.

[0183] X d Represents a chlorine atom or a bromine atom.

[0184] X 1d The combination of and nd represents:

[0185] X 1d CH is a combination of 0, 1, or 2; or,

[0186] X 1d For nitrogen atoms, nd is a combination of 1 or 2.

[0187] Group V 1 [The group consisting of C1-C4 alkyl groups, C1-C4 alkoxy groups (where the C1-C4 alkyl group and the C1-C4 alkoxy group may be substituted by one or more halogen atoms), and halogen atoms.]

[0188] (Excluding 3-chloro-5-(ethylthio)pyridine, 3-bromo-5-(ethylthio)pyridine, 3-chloro-5-(ethylsulfonyl)pyridine, 3-bromo-5-(ethylsulfonyl)pyridine, 3-chloro-5-(propylthio)pyridine, 3-chloro-5-[(1-methylethyl)thio]pyridine, 3-bromo-5-[(1-methylethyl)thio]pyridine, 3-chloro-5-[(1-methylethyl)sulfonyl]pyridine, 3-bromo-5-[(1-methylethyl)sulfonyl]pyridine, 3-chloro-5-[(1,1-dimethylethyl)thio]pyridine, 3-Bromo-5-[(1,1-dimethylethyl)thio]pyridine, 3-chloro-5-[(1,1-dimethylethyl)sulfonyl]pyridine, 3-bromo-5-[(1,1-dimethylethyl)sulfonyl]pyridine, 3-chloro-5-(cyclohexylsulfonyl)pyridine, 3-bromo-5-(cyclopropylthio)pyridine, 3-bromo-5-(cyclopropylsulfonyl)pyridine, 5-[(5-bromo-3-pyridinyl)thio]-2-methylpyridine, 5-[(5-bromo-3-pyridinyl)sulfonyl]-2-methylpyridine, and 3,3'-sulfonylbis(5-bromopyridine).

[0189] Invention Effects

[0190] This invention enables the prevention and control of plant diseases. Detailed Implementation

[0191] The substituents in this invention will be explained.

[0192] In this specification, the expression "may have" as used with respect to substituents has the same meaning as "can be replaced by".

[0193] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms.

[0194] When a substituent is replaced by two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0195] 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, E, F, G, H, A), a B a C a 、D a 、E a F a , G a H a A b B b 、D b 、E b F b , G b H b A c B c C c 、D c 、E c F c , G c and V 1 The statement that "any one of the substituents in group X" means that in the presence of more than two substituents selected from group X, these substituents may be the same or different.

[0196] 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.

[0197] The term "chain hydrocarbon group" refers to alkyl, alkenyl, or alkynyl groups.

[0198] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl.

[0199] 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.

[0200] 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.

[0201] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, and hexyloxy.

[0202] Examples of alkylthioalkyl groups include methylthioalkyl, ethylthioalkyl, isopropylthioalkyl, and hexylthioalkyl.

[0203] Examples of alkyl sulfinyl groups include methyl sulfinyl, ethyl sulfinyl, isopropyl sulfinyl, and hexyl sulfinyl.

[0204] Examples of alkyl sulfonyl groups include methanesulfonyl, ethanesulfonyl, isopropanesulfonyl, and hexanesulfonyl.

[0205] Examples of alkyl carbonyl groups include acetyl and propionyl.

[0206] Examples of alkoxycarbonyl groups include methoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl.

[0207] Examples of alicyclic hydrocarbon groups include cycloalkyl or cycloalkenyl groups.

[0208] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0209] Examples of cycloalkenyl groups include cyclopentenyl and cyclohexenyl.

[0210] Examples of aryl groups include phenyl and naphthyl groups.

[0211] Examples of aromatic heterocyclic groups include 5-membered aromatic heterocyclic groups such as pyrroleyl, furanyl, thiopheneyl, 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.

[0212] 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.

[0213] Compounds D, E, and F of this invention are designated as compound Q. Compound Q, its N oxide, or its salts are designated as compound Z. It should be noted that compound Z is synonymous with compounds R, S, and T of this invention.

[0214] Compound Y, compound Z, or intermediate A may sometimes contain more than one stereoisomer. Examples of stereoisomers include enantiomers, diastereomers, transisomers, and geometric isomers. This invention includes all stereoisomers and mixtures of stereoisomers in any ratio.

[0215] Compound X or compound Q of this invention, or its N oxide, sometimes forms 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.

[0216] In compound X or compound Q of this invention, adjacent R 2 and R 4 When the carbon atoms bonded to them together form a C5-C6 alicyclic hydrocarbon, a 5-6 membered non-aromatic heterocycle (the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have one or more substituents selected from group B), a benzene ring, or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E), specifically, for example, compound X, it is the following compound:

[0217] [Chemical Formula 6]

[0218]

[0219] In formula (IA-1),

[0220] R 1 R 3 X 1 X 2 X 3 X 4 and n represents the same meaning as [1],

[0221] R 4A and R 4B The same or different from each other indicates R with [1]. 4 The same meaning or hydrogen atom,

[0222] R 4C and R 2Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons, 5-6 membered nonaromatic heterocycles (the C5-C6 alicyclic hydrocarbons and the 5-6 membered nonaromatic heterocycles may have 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 may have one or more substituents selected from group E).

[0223] In compound X or compound Q of this invention, two adjacent R... 4 and R 4 When the carbon atoms bonded to them together form a C5-C6 alicyclic hydrocarbon, a 5-6 membered non-aromatic heterocyclic group (the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have one or more substituents selected from group B), a benzene ring, or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E), specifically, for example, compound X, it is the following compound:

[0224] 1) In equation (IA-1),

[0225] R 1 R 2 R 3 X 1 X 2 X 3 X 4 and n represents the same meaning as [1],

[0226] R 4C R represents [1]. 4 The same meaning or hydrogen atom,

[0227] R 4A and R 4B Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons, 5-6 membered non-aromatic heterocycles (the C5-C6 alicyclic hydrocarbons and the 5-6 membered non-aromatic heterocycles may have 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 may have one or more substituents selected from group E); or

[0228] 2) In equation (IA-1),

[0229] R 1 R 2 R 3 X 1 X 2 X 3 X 4 and n represents the same meaning as [1],

[0230] R 4AR represents [1]. 4 The same meaning or hydrogen atom,

[0231] R 4B and R 4C Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons, 5-6 membered nonaromatic heterocycles (the C5-C6 alicyclic hydrocarbons and the 5-6 membered nonaromatic heterocycles may have 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 may have one or more substituents selected from group E).

[0232] 3-Chloro-5-(ethylthio)pyridine is a compound represented by the following formula:

[0233] [Chemical Formula 7]

[0234]

[0235] 3-Bromo-5-(ethylthio)pyridine is a compound represented by the following formula:

[0236] [Chemical Formula 8]

[0237]

[0238] 3-Chloro-5-(ethylsulfonyl)pyridine is a compound represented by the following formula:

[0239] [Chemical Formula 9]

[0240]

[0241] 3-Bromo-5-(ethylsulfonyl)pyridine is a compound represented by the following formula:

[0242] [Chemical Formula 10]

[0243]

[0244] 3-Chloro-5-(propylthio)pyridine is a compound represented by the following formula:

[0245] [Chemical Formula 11]

[0246]

[0247] 3-Chloro-5-[(1-Methylethyl)thio]pyridine is a compound represented by the following formula:

[0248] [Chemical Formula 12]

[0249]

[0250] 3-Bromo-5-[(1-Methylethyl)thio]pyridine is a compound represented by the following formula:

[0251] [Chemical Formula 13]

[0252]

[0253] 3-Chloro-5-[(1-methylethyl)sulfonyl]pyridine is a compound represented by the following formula:

[0254] [Chemical Formula 14]

[0255]

[0256] 3-Bromo-5-[(1-methylethyl)sulfonyl]pyridine is a compound represented by the following formula:

[0257] [Chemical Formula 15]

[0258]

[0259] 3-Chloro-5-[(1,1-dimethylethyl)thio]pyridine is a compound represented by the following formula:

[0260] [Chemical Formula 16]

[0261]

[0262] 3-Bromo-5-[(1,1-dimethylethyl)thio]pyridine is a compound represented by the following formula:

[0263] [Chemical Formula 17]

[0264]

[0265] 3-Chloro-5-[(1,1-dimethylethyl)sulfonyl]pyridine is a compound represented by the following formula:

[0266] [Chemical Formula 18]

[0267]

[0268] 3-Bromo-5-[(1,1-dimethylethyl)sulfonyl]pyridine is a compound represented by the following formula:

[0269] [Chemical Formula 19]

[0270]

[0271] 3-Chloro-5-(cyclohexylsulfonyl)pyridine is a compound represented by the following formula:

[0272] [Chemical Formula 20]

[0273]

[0274] 3-Bromo-5-(cyclopropylthio)pyridine is a compound represented by the following formula:

[0275] [Chemical Formula 21]

[0276]

[0277] 3-Bromo-5-(cyclopropylsulfonyl)pyridine is a compound represented by the following formula:

[0278] [Chemical Formula 22]

[0279]

[0280] 5-[(5-bromo-3-pyridyl)thio]-2-methylpyridine is a compound represented by the following formula:

[0281] [Chemical Formula 23]

[0282]

[0283] 5-[(5-bromo-3-pyridyl)sulfonyl]-2-methylpyridine is a compound represented by the following formula:

[0284] [Chemical Formula 24]

[0285]

[0286] 3,3'-sulfonylbis(5-bromopyridine) is a compound represented by the following formula:

[0287] [Chemical Formula 25]

[0288]

[0289] Examples of compounds that can be used as a means of producing compound X include the following compounds.

[0290] [Method X1] In this compound X, R 1 It is a compound having one or more substituents selected from group A, which are C1-C6 alkyl groups.

[0291] [Method X2] In this compound X, R 1 It is a compound having one or more substituents selected from group A, which are C2-C6 alkyl groups.

[0292] [Method X3] In this compound X, R 1 It is a compound having a C2-C6 alkyl group having one or more substituents selected from group A, or a methyl group having one or more substituents selected from group C.

[0293] [Method X4] In this compound X, R 1 Compounds that are C3-C8 alicyclic hydrocarbon groups {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}.

[0294] [Method X5] In this compound X, R 1 Compounds that are C1-C6 alkyl or C2-C6 ynyl (the C1-C6 alkyl and the C2-C6 ynyl may have one or more substituents selected from group A).

[0295] [Method X6] In this compound X, R 1 A compound that is a C1-C6 alkyl, C2-C6 alkynyl (the C1-C6 alkyl and the C2-C6 alkynyl may have one or more substituents selected from group A), or a C2-C6 alkenyl chain that may have one or more substituents selected from group C.

[0296] [Method X7] In this compound X, R 1 It is a compound having a C1-C6 alkyl group or a C3-C8 alicyclic hydrocarbon group (which may have one or more substituents selected from group A) that may have one or more substituents selected from group B.

[0297] [Method X8] In this compound X, R 1 Compounds that are C1-C6 alkyl, C2-C6 alkynyl (the C1-C6 alkyl and the C2-C6 alkynyl may have one or more substituents selected from group A), or C3-C8 alicyclic hydrocarbon (the C3-C8 alicyclic hydrocarbon may have one or more substituents selected from group B).

[0298] [Method X9] In this compound X, R 1 It is a compound having a C2-C6 alkyl group having one or more substituents selected from group A, a methyl group having one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}.

[0299] [Method X10] In this compound X, R 2 and R 3 Compounds that are the same as 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.

[0300] [Method X11] In this compound X, R 2 and R 3 Compounds that are the same or different from each other and may have one or more substituents selected from group B, and are C3-C8 alicyclic hydrocarbon groups or hydrogen atoms.

[0301] [Method X12] In this compound X, R2 and R 3 Same or different from each other and OR 9 SR 10 S(O)R 11 、S(O)2R 12 NR 13 R 14 C(O)R 15 Compounds containing nitro, cyano, or hydrogen atoms.

[0302] [Method X13] In this compound X, R 2 and R 3 Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0303] [Method X14] In this compound X, R 2 and R 3 Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0304] [Method X15] In this compound X, R 2 and R 3 Compounds containing hydrogen atoms.

[0305] [Method X16] In this compound X, R 4 It is a compound having one or more substituents selected from group A, which are C1-C6 chain hydrocarbon groups.

[0306] [Method X17] In this compound X, 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}.

[0307] [Method X18] In this compound X, R 4 Compounds that are phenyl or 5-6 membered aromatic heterocyclic groups {the phenyl group and the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D}.

[0308] [Method X19] In this compound X, R 4 OR 16 SR 17 S(O)R 18 、S(O)2R 19 NR 20 R 21 C(O)R 22 C(R) 23 ) = NOR 24 Compounds with cyano, nitro, amino, or hydroxyl groups.

[0309] [Method X20] In this compound X, R 4 Compounds containing halogen atoms.

[0310] [Method X21] In this compound X, R 4 It is a compound that may have one or more substituents selected from group A, which are C1-C6 chain hydrocarbon groups or halogen atoms.

[0311] [Method X22] In this compound X, R 4 It can be a C1-C6 chain hydrocarbon group having one or more substituents selected from group A, OR 16 Compounds containing cyano, nitro, or halogen atoms.

[0312] [Method X23] In this compound X, adjacent R 2 and R 4 Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons or 5-6 membered nonaromatic heterocycles {the C5-C6 alicyclic hydrocarbons and the 5-6 membered nonaromatic heterocycles may have one or more substituents selected from group B}.

[0313] [Method X24] In this compound X, adjacent R 2 and R 4 Together with the carbon atoms they are bonded to, they form compounds with benzene rings or 5-6 membered aromatic heterocycles {the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E}.

[0314] [Method X25] In this compound X, two adjacent R 4 and R 4 Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons or 5-6 membered nonaromatic heterocycles {the C5-C6 alicyclic hydrocarbons and the 5-6 membered nonaromatic heterocycles may have one or more substituents selected from group B}.

[0315] [Method X26] In this compound X, two adjacent R 4 and R 4 Together with the carbon atoms they are bonded to, they form compounds with benzene rings or 5-6 membered aromatic heterocycles {the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E}.

[0316] [Method X27] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 For CR 5 X 2 For CR6 X 3 For nitrogen atoms, X 4 For CR 8 Compounds consisting of combinations of .

[0317] [Method X28] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 For CR 5 X 2 For CR 6 X 3 For CR 7 X 4 A combination of nitrogen atoms; X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 Combinations; X 1 For CR 5 X 2 For nitrogen atoms, X 3 For CR 7A X 4 For CR 8 Combinations; or X 1 For nitrogen atoms, X 2 For CR 6 X 3 For CR 7B X 4 For CR 8 Compounds consisting of combinations of .

[0318] [Method X29] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 For nitrogen atoms, X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 Compounds consisting of combinations of .

[0319] [Method X30] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3CR 7C X 4 Combinations of CH; X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 For CH, X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 For nitrogen atoms, X 3 For CH, X 4 A combination of nitrogen atoms; or X 1 For CH, X 2 For nitrogen atoms, X 3 CR 7D X 4 Compounds consisting of combinations of nitrogen atoms.

[0320] [Method X31] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 CR 8 Combinations; or X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 Compounds consisting of combinations of nitrogen atoms.

[0321] [Method X32] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 CR6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 CR 7A X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0322] [Method X33] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0323] [Method X34] In this compound X, R 5 R 6 R 7 R 7A R 7B and R 8 The same or different from each other and consisting of C1-C6 chain hydrocarbon groups or hydrogen atoms that can be substituted by more than one halogen atom, R 7C and R 7D Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom.

[0324] [Method X35] In this compound X, R 5 R 6 R 7 R 7A R 7B and R 8 The same or different from each other and may have C3-C8 alicyclic hydrocarbon groups or hydrogen atoms selected from group B, R 7C and R 7D Compounds that are the same as or different from each other and that may have one or more substituents selected from group B, and are C3-C8 alicyclic hydrocarbon groups.

[0325] [Method X36] In this compound X, R 5 R 6 R 7 and R 8 Same or different from each other and OR 25 SR 26 S(O)R 27 、S(O)2R 28 NR 29 R 30 C(O)R 31 Compounds containing nitro, cyano, or hydrogen atoms.

[0326] [Method X37] In this compound X, R 5 R 6 R 7 R 7A R 7B and R 8 The same or different from each other and consisting of halogen atoms or hydrogen atoms, R 7C For halogen atoms, R 7D Compounds consisting of fluorine, chlorine, or iodine atoms.

[0327] [Method X38] In this compound X, R 5 R 6 R 7 R 7A R 7B and R 8 The same or different from each other and consisting of a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms, R 7C R is a C1-C6 chain hydrocarbon group or halogen atom that can be replaced by one or more halogen atoms. 7D Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0328] [Method X39] In this compound X, R 5 R 6 R 7 R7A R 7B and R 8 The same or different from each other and being C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 25 NR 29 R 32 C(O)R 31 nitro, cyano, halogen atom or hydrogen atom, R 7C C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, OR 25 NR 29 R 30 C(O)R 31 nitro, cyano, or halogen atom, R 7D C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, OR 25 NR 29 R 30 C(O)R 31 Compounds with nitro or cyano groups.

[0329] [Method X40] In this compound X, R 5 R 6 R 7 R 7A R 7B and R 8 Compounds containing hydrogen atoms.

[0330] [Method X41] In this compound X, n is 0.

[0331] [Method X42] In this compound X, n is 1.

[0332] [Method X43] In this compound X, n is 2.

[0333] [Method X44] In this compound X, the compound in which q is 1.

[0334] [Method X45] In this compound X, q is 2.

[0335] [Method X46] In this compound X, q is 3.

[0336] [Method X47] In this compound X, R 1 X is a C2-C6 alkyl group having one or more substituents selected from group A, a methyl group having one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}. 1 X 2 X 3 and X4 The combination is X 1 CR 5 X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 CR 7A X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 CR 8 Combinations; or X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 R is a combination of nitrogen atoms. 5 R 6 R 7 R 7A R 7B and R 8 A compound consisting of a C1-C6 chain hydrocarbon group, a halogen atom, or a hydrogen atom that can be replaced by one or more halogen atoms.

[0337] [Method X48] In this compound X, R 1 R is a C1-C6 alkyl group that may have one or more substituents selected from group A.2 and R 3 The same or different from each other and consisting of halogen atoms or hydrogen atoms, R 4 It can be a C1-C6 chain hydrocarbon group having one or more substituents selected from group A, OR 16 SR 17 NR 20 R 21 , cyano, nitro or halogen atom, R 5 R 6 R 7 R 7A R 7B R 7C and R 8 The same or different from each other and being C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 25 NR 29 R 32 C(O)R 31 , cyano, halogen atom or hydrogen atom, R 7D Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0338] [Method X49] A seed or vegetative reproductive organ that retains an effective amount of this compound X or its N oxide or their salts.

[0339] [Method X50] In this compound X, R 1 It is a compound having one or more substituents selected from group D, which are 5-10 membered aromatic heterocyclic groups.

[0340] [Method X51] In this compound X, R 1 It is a compound having one or more substituents selected from group D, which are 5-6 membered aromatic heterocyclic groups.

[0341] [Method X52] In this compound X, R 1 It is a compound having one or more substituents selected from group F, that is a C6-C10 aryl group.

[0342] [Method X53] In this compound X, R 1 It is a compound that may have one or more substituents selected from group F.

[0343] [Method X54] In this compound X, R 1 It is a compound having a 3-8 membered non-aromatic heterocyclic group having one or more substituents selected from group B.

[0344] [Method X55] In this compound X, R 1 It is a compound having a 4-6 membered non-aromatic heterocyclic group having one or more substituents selected from group B.

[0345] [Method X56] In this compound X, R 1 NR 33 R 34 Compounds.

[0346] [Method X57] In this compound X, R 1 NR 33 R 34 R 33 It is a C1-C6 chain hydrocarbon group or a C3-C6 alicyclic hydrocarbon group, R 34 Compounds consisting of C1-C6 chain hydrocarbon groups, C3-C6 alicyclic hydrocarbon groups, or hydrogen atoms.

[0347] [Method X58] In this compound X, R 1 It is a compound having a C1-C6 alkyl group having one or more substituents selected from group A, a C6-C10 aryl group having one or more substituents selected from group F, or a 5-10 membered aromatic heterocyclic group {the 5-10 membered aromatic heterocyclic group may have one or more substituents selected from group D}.

[0348] [Method X59] In this compound X, R 1 It is a compound having a C1-C6 alkyl group having one or more substituents selected from group A, a phenyl group having one or more substituents selected from group F, or a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D}.

[0349] [Method X60] In this compound X, R 1 It can be a C1-C6 alkyl group having one or more substituents selected from group A, a C6-C10 aryl group having one or more substituents selected from group F, a 5-10 membered aromatic heterocyclic group having one or more substituents selected from group D, a 3-8 membered non-aromatic heterocyclic group having one or more substituents selected from group B, or NR. 33 R 34 Compounds.

[0350] [Method X61] In this compound X, R 1 It can be a C1-C6 alkyl group having one or more substituents selected from group A, a phenyl group having one or more substituents selected from group F, a 5-6 membered aromatic heterocyclic group having one or more substituents selected from group D, a 4-6 membered non-aromatic heterocyclic group having one or more substituents selected from group B, or NR. 33 R 34 Compounds.

[0351] [Method X62] In this compound X, R 1Compounds that are phenyl, pyridyl, pyridinyl, pyrimidinyl, pyrazinyl, furanyl, thiophene, oxazolyl, or thiazolyl {the phenyl, pyridyl, pyridinyl, pyrimidinyl, pyrazinyl, furanyl, thiophene, oxazolyl, and thiazolyl may have one or more substituents selected from group H}.

[0352] Group H: The group consisting of C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, C1-C6 alkoxy groups {the C1-C6 chain hydrocarbon group, the C3-C8 alicyclic hydrocarbon group and the C1-C6 alkoxy group may be substituted by more than one halogen atom}, halogen atoms, nitro groups and cyano groups.

[0353] [Method X63] In this compound X, R 1 It can be a phenyl group that can be substituted with one or more halogen atoms, a 5-6 membered aromatic heterocyclic group that may have one or more substituents selected from group H, a 3-8 membered non-aromatic heterocyclic group, a C1-C6 alkyl group that may have one or more substituents selected from group A, or NR. 33 R 34 , R 2 and R 3 The same or different from each other and consisting of a C1-C6 chain hydrocarbon group, a halogen atom, or a hydrogen atom, R 4 It can be a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, or an OR group having one or more substituents selected from group A. 16 SR 17 NR 20 R 21 Cyano, nitro, or halogen atom, two adjacent R 4 and R 4 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 halogen atoms), or 5-6 membered aromatic heterocycles (where the 5-6 membered aromatic heterocycle can be substituted by one or more halogen atoms) together with the carbon atoms they are bonded to. 5 R 6 R 7 R 7A R 7B and R 8 The same or different from each other and being C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 25 NR 29 R 32 C(O)R 31 , cyano, halogen atom or hydrogen atom, R 7C R is a C1-C6 chain hydrocarbon group or halogen atom that can be replaced by one or more halogen atoms. 7D Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0354] [Method X64] In this compound X, n and R 1 The combination is where n is 0, 1, or 2, R 1 It is a combination of C1-C6 alkyl, C2-C6 ynyl (the C1-C6 alkyl and the C2-C6 ynyl may have one or more substituents selected from group A), C2-C6 alkenyl (may have one or more substituents selected from group C), C6-C10 aryl (may have one or more substituents selected from group F), 5-10 membered aromatic heterocyclic group (may have one or more substituents selected from group D), or C3-C8 alicyclic hydrocarbon (the C3-C8 alicyclic hydrocarbon may have one or more substituents selected from group B); or, n is 2, R 1 It is a 3-8 membered non-aromatic heterocyclic group that may have one or more substituents selected from group B, or NR 33 R 34 Compounds consisting of combinations of .

[0355] [Method X65] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 The combination of R 5 R 6 and R 8 Compounds containing hydrogen atoms.

[0356] [Method X66] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 The combination of R 5 R 6 and R 8 Compounds containing hydrogen atoms.

[0357] [Method X67] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 The combination of R 6 and R 8 Compounds containing hydrogen atoms.

[0358] [Method X68] In this compound X, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 CR 7A X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 For CH, X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X1 For nitrogen atoms, X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 For CH, X 4 A combination of nitrogen atoms; or X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 R is a combination of nitrogen atoms. 5 R 6 R 7 R 7A R 7B and R 8 Compounds containing hydrogen atoms.

[0359] Examples of compounds N can be cited as a form of this compound N.

[0360] [Method 1] In this compound N, R 1 It is a compound having one or more substituents selected from group A, which are C1-C6 alkyl groups.

[0361] [Method 2] In this compound N, R 1 It is a compound having one or more substituents selected from group A, which are C2-C6 alkyl groups.

[0362] [Method 3] In this compound N, R 1 It is a compound having a C2-C6 alkyl group having one or more substituents selected from group A, or a methyl group having one or more substituents selected from group C.

[0363] [Method 5] In this compound N, R 1 Compounds that are C3-C8 alicyclic hydrocarbon groups {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}.

[0364] [Method 6] In this compound N, R 1Compounds that are C1-C6 alkyl or C2-C6 ynyl (the C1-C6 alkyl and the C2-C6 ynyl may have one or more substituents selected from group A).

[0365] [Method 7] In this compound N, R 1 A compound that is a C1-C6 alkyl, C2-C6 alkynyl (the C1-C6 alkyl and the C2-C6 alkynyl may have one or more substituents selected from group A), or a C2-C6 alkenyl chain that may have one or more substituents selected from group C.

[0366] [Method 8] In this compound N, R 1 It is a compound having one or more substituents selected from group A, namely a C1-C6 alkyl group or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}.

[0367] [Method 9] In this compound N, R 1 Compounds that are C1-C6 alkyl, C2-C6 alkynyl (the C1-C6 alkyl and the C2-C6 alkynyl may have one or more substituents selected from group A), or C3-C8 alicyclic hydrocarbon (the C3-C8 alicyclic hydrocarbon may have one or more substituents selected from group B).

[0368] [Method 10] In this compound N, R 1 It is a compound having a C2-C6 alkyl group having one or more substituents selected from group A, a methyl group having one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}.

[0369] [Method 11] In this compound N, R 2 and R 3 Compounds that are the same as 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.

[0370] [Method 12] In this compound N, R 2 and R 3 Compounds that are the same or different from each other and may have one or more substituents selected from group B, and are C3-C8 alicyclic hydrocarbon groups or hydrogen atoms.

[0371] [Method 13] In this compound N, R 2 and R 3 Same or different from each other and OR 9 SR 10 S(O)R 11 、S(O)2R 12 NR 13 R14 C(O)R 15 Compounds containing nitro, cyano, or hydrogen atoms.

[0372] [Method 14] In this compound N, R 2 and R 3 Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0373] [Method 15] In this compound N, R 2 and R 3 Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0374] [Method 16] In this compound N, R 2 and R 3 Compounds containing hydrogen atoms.

[0375] [Method 17] In this compound N, R 4 It is a compound having one or more substituents selected from group A, which are C1-C6 chain hydrocarbon groups.

[0376] [Method 18] In this compound N, 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}.

[0377] [Method 19] In this compound N, R 4 Compounds that are phenyl or 5-6 membered aromatic heterocyclic groups {the phenyl group and the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D}.

[0378] [Method 20] In this compound N, R 4 OR 16 SR 17 S(O)R 18 、S(O)2R 19 NR 20 R 21 C(O)R 22 C(R) 23 ) = NOR 24 Compounds with cyano, nitro, amino, or hydroxyl groups.

[0379] [Method 21] In this compound N, R 4 Compounds containing halogen atoms.

[0380] [Method 22] In this compound N, R 4It is a compound that may have one or more substituents selected from group A, which are C1-C6 chain hydrocarbon groups or halogen atoms.

[0381] [Method 23] In this compound N, R 4 It can be a C1-C6 chain hydrocarbon group having one or more substituents selected from group A, OR 16 Compounds containing cyano, nitro, or halogen atoms.

[0382] [Method 24] In this compound N, adjacent R 2 and R 4 Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocyclic groups {the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have one or more substituents selected from group B}.

[0383] [Method 25] In this compound N, adjacent R 2 and R 4 Together with the carbon atoms they are bonded to, they form compounds with benzene rings or 5-6 membered aromatic heterocycles {the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E}.

[0384] [Method 26] In this compound N, adjacent R 4 and R 4 Together with the carbon atoms they are bonded to, they form compounds of C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocyclic groups {the C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have one or more substituents selected from group B}.

[0385] [Method 27] In this compound N, adjacent R 4 and R 4 Together with the carbon atoms they are bonded to, they form compounds with benzene rings or 5-6 membered aromatic heterocycles {the benzene ring and the 5-6 membered aromatic heterocycle may have one or more substituents selected from group E}.

[0386] [Method 28] In this compound, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0387] [Method 29] In this compound N, X 1 X2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 CR 7 X 4 A combination of nitrogen atoms; X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; X 1 CR 5 X 2 For nitrogen atoms, X 3 CR 7A X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Compounds consisting of combinations of .

[0388] [Method 30] In this compound N, X 1 X 2 X 3 and X 4 The combination is X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0389] [Method 31] In this compound N, X 1 X 2 X 3 and X 4 The combination is X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 CR 7C X 4 Combinations of CH; X 1 For nitrogen atoms, X 2 For nitrogen atoms, X 3 For CH, X 4 CR 8Combinations; X 1 For nitrogen atoms, X 2 For CR 6 X 3 For CR 7 X 4 A combination of nitrogen atoms; X 1 For CR 5 X 2 For nitrogen atoms, X 3 For CH, X 4 A combination of nitrogen atoms; or X 1 For CH, X 2 For nitrogen atoms, X 3 For CR 7D X 4 Compounds consisting of combinations of nitrogen atoms.

[0390] [Method 32] In this compound N, X 1 X 2 X 3 and X 4 The combination is X 1 For CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 For CR 8 Combinations; or X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 Compounds consisting of combinations of nitrogen atoms.

[0391] [Method 33] In this compound N, X 1 X 2 X 3 and X 4 The combination is X 1 For CR 5 X 2 For CR 6 X 3 For CR 7 X 4 A combination of nitrogen atoms; X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 Combinations; X 1 For CR 5 X 2 For nitrogen atoms, X 3CR 7A X 4 CR 8 Combinations; X 1 For nitrogen atoms, X 2 CR 6 X 3 CR 7B X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0392] [Method 34] In this compound N, X 1 X 2 X 3 and X 4 The combination is X 1 CR 5 X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Combinations; or X 1 For nitrogen atoms, X 2 CR 6 X 3 For nitrogen atoms, X 4 CR 8 Compounds consisting of combinations of .

[0393] [Method 35] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C R 7D and R 8 Compounds that are the same as 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.

[0394] [Method 36] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C R 7D and R 8Compounds that are the same or different from each other and may have one or more substituents selected from group B, and are C3-C8 alicyclic hydrocarbon groups or hydrogen atoms.

[0395] [Method 37] In this compound N, R 5 R 6 R 7 and R 8 Same or different from each other and OR 25 SR 26 S(O)R 27 、S(O)2R 28 NR 29 R 30 C(O)R 31 Compounds containing nitro, cyano, or hydrogen atoms.

[0396] [Method 38] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C and R 8 The same or different from each other and consisting of halogen atoms or hydrogen atoms, R 7D Compounds containing hydrogen atoms.

[0397] [Method 39] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C and R 8 The same or different from each other and consisting of a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms, R 7D A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0398] [Method 40] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C and R 8 The same or different from each other and being C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 25 NR 29 R 32 C(O)R 31 nitro, cyano, halogen atom or hydrogen atom, R 7D C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, OR25 NR 29 R 32 C(O)R 31 Compounds containing nitro, cyano, or hydrogen atoms.

[0399] [Method 41] In this compound N, R 5 R 6 R 7 R 7A R 7B R 7C R 7D and R 8 Compounds containing hydrogen atoms.

[0400] [Method 42] Compounds in which n is 0 in this compound N.

[0401] [Method 43] In this compound N, n is 1.

[0402] [Method 44] Compounds in which n is 2 in this compound N.

[0403] [Method 45] In this compound N, the compound in which q is 1.

[0404] [Method 46] In this compound N, the compound in which q is 2.

[0405] [Method 47] Compound N in which q is 3.

[0406] [Method 48] In this compound N, R 1 X is a C2-C6 alkyl group having one or more substituents selected from group A, a methyl group having one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}. 1 X 2 X 3 and X 4 The combination is X 1 For CR 5 X 2 For CR 6 X 3 For CR 7 X 4 A combination of nitrogen atoms; X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 Combinations; X 1 For CR 5 X 2For nitrogen atoms, X 3 For CR 7A X 4 For CR 8 Combinations; X 1 For nitrogen atoms, X 2 For CR 6 X 3 For CR 7B X 4 For CR 8 Combinations; X 1 For nitrogen atoms, X 2 For CR 6 X 3 For nitrogen atoms, X 4 For CR 8 Combinations; X 1 For CR 5 X 2 For nitrogen atoms, X 3 For nitrogen atoms, X 4 For CR 8 Combinations; or X 1 For CR 5 X 2 For CR 6 X 3 For nitrogen atoms, X 4 R is a combination of nitrogen atoms. 5 R 6 R 7 R 7A R 7B and R 8 A compound consisting of a C1-C6 chain hydrocarbon group, a halogen atom, or a hydrogen atom that can be replaced by one or more halogen atoms.

[0407] [Method 49] In this compound N, R 1 R is a C1-C6 alkyl group that may have one or more substituents selected from group A. 2 and R 3 The same or different from each other and consisting of halogen atoms or hydrogen atoms, R 4 It can be a C1-C6 chain hydrocarbon group having one or more substituents selected from group A, OR 16 SR 17 NR 20 R 21 , cyano, nitro or halogen atom, R 5 R 6 R 7 R 7A R 7B R 7C and R 8The same or different from each other and being C1-C6 chain hydrocarbon groups that can be substituted by more than one halogen atom, OR 25 NR 29 R 32 C(O)R 31 , cyano, halogen atom or hydrogen atom, R 7D Compounds that are C1-C6 chain hydrocarbon groups that can be replaced by one or more halogen atoms.

[0408] [Method 50] A seed or vegetative reproductive organ that retains an effective amount of the compound N or its N oxide or their salts.

[0409] Examples of compounds that can be used as compound D in this invention include the following compounds.

[0410] [Method D1] In compound D of the present invention, R 1a To have the option to select from group A a Compounds of C2-C6 alkyl groups with one or more substituents.

[0411] [Method D2] In compound D of the present invention, R 1a To have the option to select from group A a Compounds with one or more substituents in the C2-C6 alkynyl group.

[0412] [Method D3] In compound D of the present invention, R 1a To have selected from group F a Compounds with one or more substituents in the C2-C6 alkenyl chain.

[0413] [Method D4] In compound D of the present invention, R 1a To have the option to select from group B a Compounds of C3-C8 alicyclic hydrocarbon groups with one or more substituents.

[0414] [Method D5] In compound D of the present invention, R 1a For having selected from group C a Compounds containing one or more methyl groups.

[0415] [Method D6] In compound D of the present invention, R 1a To have the option to select from group A a C2-C6 alkyl groups with one or more substituents, and may have groups selected from group A a The C2-C6 ynyl group has one or more substituents, or may have a group selected from group F a Compounds with one or more substituents in the C2-C6 alkenyl chain.

[0416] [Method D7] In compound D of the present invention, R 1a To have the option to select from group Aa C2-C6 alkyl groups with one or more substituents, or having a group selected from C1-C6. a Compounds containing one or more methyl groups.

[0417] [Method D8] In compound D of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, or may have groups selected from group B a Compounds of C3-C8 alicyclic hydrocarbon groups with one or more substituents.

[0418] [Method D9] In compound D of the present invention, R 2a and R 3a Compounds that are the same as 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.

[0419] [Method D10] In compound D of the present invention, R 2a and R 3a They are the same or different from each other and can be selected from group B. a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0420] [Method D11] In compound D of the present invention, R 2a and R 3a Same or different from each other and OR 15a SR 16a S(O)R 17a 、S(O)2R 18a NR 19a R 20a C(O)R 21a Compounds containing nitro, cyano, or hydrogen atoms.

[0421] [Method D12] In compound D of the present invention, R 2a and R 3a Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0422] [Method D13] In compound D of the present invention, R 2a and R 3a Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0423] [Method D14] In compound D of the present invention, X a For nitrogen atoms, R 4a To have selected from group A aC1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a 、S(O)2R 26a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a , cyano, nitro, amino, hydroxyl or halogen atom, R 6a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R 13a C(O)R 14a Compounds containing nitro, cyano, halogen, or hydrogen atoms.

[0424] [Method D15] In compound D of the present invention, X a CR 5a R 4a To have selected from group F a The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. a C2-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a 、S(O)2R 22a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR31a , cyano, nitro, amino, hydroxyl or halogen atom, R 6a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a Compounds containing nitro, fluorine, bromine, iodine, or hydrogen atoms.

[0425] [Method D16] In compound D of the present invention, R 6a A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0426] [Method D17] In compound D of the present invention, R 6a To have the option to select from group B a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0427] [Method D18] In compound D of the present invention, R 6a OR 7a Compounds containing nitro or hydrogen atoms.

[0428] [Method D19] In compound D of the present invention, X a For CR 5a , R 6a Compounds consisting of fluorine, bromine, iodine, or hydrogen atoms.

[0429] [Method D20] In compound D of the present invention, X a For nitrogen atoms, R 6a Compounds consisting of halogen atoms or hydrogen atoms.

[0430] [Method D21] In compound D of the present invention, R 6a Compounds containing hydrogen atoms.

[0431] [Method D22] In compound D of the present invention, X a For CR 5a , R 4a To have selected from group F a The methyl, CH2F, CHF2, or other substituents in the group may be selected from group A. a Compounds of C2-C6 chain hydrocarbon groups with one or more substituents.

[0432] [Method D23] In compound D of the present invention, X a For CR 5a , R 4a OR 23a SR 24a S(O)R 25a、S(O)2R 22a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Compounds with cyano, nitro, amino, or hydroxyl groups.

[0433] [Method D24] In compound D of the present invention, X a For nitrogen atoms, R 4a To have the option to select from group A a Compounds of C1-C6 chain hydrocarbon groups with one or more substituents.

[0434] [Method D25] In compound D of the present invention, X a For nitrogen atoms, R 4a OR 23a SR 24a S(O)R 25a 、S(O)2R 26a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Compounds with cyano, nitro, amino, or hydroxyl groups.

[0435] [Method D26] In compound D 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} a Compounds with one or more substituents in the compound.

[0436] [Method D27] In compound D of the present invention, R 4a It is a phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have a group selected from group D} a Compounds with one or more substituents in the compound.

[0437] [Method D28] In compound D of the present invention, R 4a Compounds containing halogen atoms.

[0438] [Method D29] In compound D of the present invention, X a For CR 5a , R 4a To have selected from group F a The methyl group with one or more substituents may have a group selected from group A. a Compounds consisting of a C2-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0439] [Method D30] In compound D of the present invention, X a For nitrogen atoms, R 4a To have the option to select from group A a Compounds consisting of a C1-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0440] [Method D31] In compound D of the present invention, X a For CR 5a , R 4a To have selected from group F a The methyl group with one or more substituents may have a group selected from group A. a C2-C6 chain hydrocarbon groups with one or more substituents, OR 23a Compounds containing cyano, nitro, hydroxyl, or halogen atoms.

[0441] [Method D32] In compound D of the present invention, X a For nitrogen atoms, R 4a To have the option to select from group A a C1-C6 chain hydrocarbon groups with one or more substituents, OR 23a Compounds containing cyano, nitro, hydroxyl, or halogen atoms.

[0442] [Method D33] In compound D of the present invention, adjacent R 2a and R 4a Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a Compounds with one or more substituents in the compound.

[0443] [Method D34] In compound D of the present invention, adjacent R 2a and R 4a Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). a Compounds with one or more substituents in the compound.

[0444] [Method D35] In compound D of the present invention, two adjacent R 4a and R 4a Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a Compounds with one or more substituents in the compound.

[0445] [Method D36] In compound D of the present invention, two adjacent R 4aand R 4a Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). a Compounds with one or more substituents in the compound.

[0446] [Method D37] In compound D of the present invention, R 5a and R 8a Compounds that are the same as 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.

[0447] [Method D38] In compound D of the present invention, R 5a and R 8a They are the same or different from each other and can be selected from group B. a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0448] [Method D39] In compound D of the present invention, R 5a and R 8a Same or different from each other and OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R 13a C(O)R 14a Compounds containing nitro, cyano, or hydrogen atoms.

[0449] [Method D40] In compound D of the present invention, R 5a and R 8a Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0450] [Method D41] In compound D of the present invention, R 5a and R 8a Compounds containing hydrogen atoms.

[0451] [Method D42] In compound D of the present invention, R 5a and R 8a Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0452] [Method D43] The compound D of the present invention in which na is 0.

[0453] [Method D44] The compound D of the present invention in which na is 1.

[0454] [Method D45] The compound D of the present invention, wherein na is 2.

[0455] [Method D46] The compound D of the present invention, wherein qa is 1.

[0456] [Method D47] The compound D of the present invention, wherein qa is 2.

[0457] [Method D48] The compound D of the present invention, wherein qa is 3.

[0458] [Method D49] In compound D of the present invention, R 5a R 6a and R 8a Compounds containing hydrogen atoms.

[0459] [Method D50] In compound D of the present invention, R 2a and R 3a Compounds containing hydrogen atoms.

[0460] [Method D51] In compound D of the present invention, R 1a To have the option to select from group A a C2-C6 alkyl groups with one or more substituents, or having a group selected from C1-C6. a A methyl group with one or more substituents, R 2a and R 3a The same or different from each other and consisting of a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms, R 4a It is methyl, and may contain elements selected from group A. a C2-C6 chain hydrocarbon groups with one or more substituents, OR 23a , cyano, nitro or halogen atom, R 5a R 6a and R 8a Compounds containing hydrogen atoms.

[0461] [Method D52] In compound D of the present invention, R 1a To have the option to select from G a Compounds of 5-6 membered aromatic heterocyclic groups with one or more substituents.

[0462] [Method D53] In compound D of the present invention, R 1a To have the option to select from group A a C2-C6 alkyl groups with one or more substituents, or having groups selected from group D a Compounds of 5-6 membered aromatic heterocyclic groups with one or more substituents.

[0463] [Method D54] In compound D of the present invention, R 1a To have selected from group H aCompounds of 5-6 membered aromatic heterocyclic groups with one or more substituents.

[0464] Group H a The group consisting of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups (which may be substituted by one or more halogen atoms) and halogen atoms.

[0465] [Method D55] In compound D of the present invention, R 1a The phenyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, furanyl group, thiophenyl group, oxazolyl group, or thiazolyl group may have a group selected from group H. a Compounds with one or more substituents in the compound.

[0466] [Method D56] In compound D of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, or having groups selected from group H a 5-6 membered aromatic heterocyclic groups with one or more substituents, R 2a and R 3a The same or different from each other and consisting of a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms, R 4a To have selected from group F a The methyl group or CHF2 group with one or more substituents may have a group selected from group A. a The C2-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylthioalkyl group, C2-C8 dialkylamino group (the C1-C6 alkoxy group, the C1-C6 alkylthioalkyl group, and the C2-C8 dialkylamino group may be substituted by one or more halogen atoms), cyano group, nitro group, or halogen atom, R 5a R 6a and R 8a Compounds containing hydrogen atoms.

[0467] Examples of compounds N in this invention include the following compounds.

[0468] [Method C1] In compound N of the present invention, R 1a To have selected from group A a Compounds of C2-C6 alkyl groups with one or more substituents.

[0469] [Method C2] In compound N of the present invention, R 1a To have selected from group A a Compounds with one or more substituents in the C2-C6 alkynyl group.

[0470] [Method C3] In compound N of the present invention, R 1a To have selected from group F a Compounds with one or more substituents in the C2-C6 alkenyl chain.

[0471] [Method C4] In compound N of the present invention, R 1a To have the option to select from group B a Compounds of C3-C8 alicyclic hydrocarbon groups with one or more substituents.

[0472] [Method C5] In compound N of the present invention, R 1a For having selected from group C a Compounds containing one or more methyl groups.

[0473] [Method C6] In compound N of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, and may have groups selected from group A a The C2-C6 ynyl group with one or more substituents may have a group selected from group F a Compounds with one or more substituents in the C2-C6 alkenyl chain.

[0474] [Method C7] In compound N of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, having a group selected from C1-C6. a Compounds containing one or more methyl groups.

[0475] [Method C8] In compound N of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, and may have groups selected from group B a Compounds of C3-C8 alicyclic hydrocarbon groups with one or more substituents.

[0476] [Method C9] In compound N of the present invention, R 2a and R 3a Compounds that are the same as 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.

[0477] [Method C10] In compound N of the present invention, R 2a and R 3a They are the same or different from each other and can be selected from group B. a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0478] [Method C11] In compound N of the present invention, R 2a and R 3a Same or different from each other and OR 15a SR 16a S(O)R 17a 、S(O)2R 18a NR 19a R 20a C(O)R 21a Compounds containing nitro, cyano, or hydrogen atoms.

[0479] [Method C12] In compound N of the present invention, R 2a and R 3a Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0480] [Method C13] In compound N of the present invention, R 2a and R 3a Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be replaced by one or more halogen atoms.

[0481] [Method C14] In compound N of the present invention, X a For nitrogen atoms, R 4a To have the option to select from group A a C1-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a 、S(O)2R 26a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a , cyano, nitro, amino, hydroxyl or halogen atom, R6 a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a SR 9a S(O)R 10a 、S(O)2R 11a NR 12a R13a C(O)R 14a Compounds containing nitro, cyano, halogen, or hydrogen atoms.

[0482] [Method C15] In compound N of the present invention, X a CR 5a R 4a To have selected from group F a The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. a C2-C6 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} a The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. a One or more substituents in OR 23a SR 24a S(O)R 25a 、S(O)2R 22a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a , cyano, nitro, amino, hydroxyl or halogen atom, R 6a It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. a C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7a Compounds containing nitro, fluorine, bromine, iodine, or hydrogen atoms.

[0483] [Method C16] In compound N of the present invention, R 6a A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0484] [Method C17] In compound N of the present invention, R 6a To have the option to select from group B a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0485] [Method C18] In compound N of the present invention, R 6a OR 7a Compounds containing nitro or hydrogen atoms.

[0486] [Method C19] In compound N of the present invention, X a CR 5aR 6a Compounds consisting of fluorine, bromine, iodine, or hydrogen atoms.

[0487] [Method C20] In compound N of the present invention, X a For nitrogen atoms, R 6a Compounds consisting of halogen atoms or hydrogen atoms.

[0488] [Method C21] In compound N of the present invention, R 6a Compounds containing hydrogen atoms.

[0489] [Method C22] In compound N of the present invention, X a CR 5a R 4a To have selected from group F a The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. a Compounds of C2-C6 chain hydrocarbon groups with one or more substituents.

[0490] [Method C23] In the compounds of the present invention, X a CR 5a R 4a OR 23a SR 24a S(O)R 25a 、S(O)2R 22a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Compounds with cyano, nitro, amino, or hydroxyl groups.

[0491] [Method C24] In compound N of the present invention, X a For nitrogen atoms, R 4a To have selected from group A a Compounds of C1-C6 chain hydrocarbon groups with one or more substituents.

[0492] [Method C25] In the compounds of the present invention, X a For nitrogen atoms, R 4a OR 23a SR 24a S(O)R 25a 、S(O)2R 26a NR 27a R 28a C(O)R 29a C(R) 30a ) = NOR 31a Compounds with cyano, nitro, amino, or hydroxyl groups.

[0493] [Method C26] In compound N 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. a Compounds with one or more substituents in the compound.

[0494] [Method C27] In compound N of the present invention, R 4a It is a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have the following characteristics selected from group D} a Compounds with one or more substituents in the compound.

[0495] [Method C28] In compound N of the present invention, R 4a Compounds containing halogen atoms.

[0496] [Method C29] In compound N of the present invention, X a CR 5a R 4a To have selected from group F a The methyl group with one or more substituents may have a group selected from group A. a Compounds consisting of a C2-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0497] [Method C30] In compound N of the present invention, X a For nitrogen atoms, R 4a To have selected from group A a Compounds consisting of a C1-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0498] [Method C31] In compound N of the present invention, X a CR 5a R 4a To have selected from group F a The methyl group with one or more substituents may have a group selected from group A. a C2-C6 chain hydrocarbon groups with one or more substituents, OR 23a Compounds containing cyano, nitro, hydroxyl, or halogen atoms.

[0499] [Method C32] In compound N of the present invention, X a For nitrogen atoms, R 4a To have selected from group A a C1-C6 chain hydrocarbon groups with one or more substituents, OR 23a Compounds containing cyano, nitro, hydroxyl, or halogen atoms.

[0500] [Method C33] In compound N of the present invention, adjacent R 2a and R 4a Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocyclic groups. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a Compounds with one or more substituents in the compound.

[0501] [Method C34] In compound N of the present invention, adjacent R 2a and R 4a Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). a Compounds with one or more substituents in the compound.

[0502] [Method C35] In compound N of the present invention, adjacent R 4a and R 4a Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons and 5-6 membered non-aromatic heterocyclic groups. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) a Compounds with one or more substituents in the compound.

[0503] [Method C36] In compound N of the present invention, adjacent R 4a and R 4a Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). a Compounds with one or more substituents in the compound.

[0504] [Method C37] In compound N of the present invention, R 5a and R 8a Compounds that are the same as 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.

[0505] [Method C38] In compound N of the present invention, R 5a and R 8a They are the same or different from each other and can be selected from group B. a A compound consisting of a C3-C8 alicyclic hydrocarbon group or a hydrogen atom with one or more substituents.

[0506] [Method C39] In compound N of the present invention, R 5a and R 8a Same or different from each other and OR 7a SR 9a S(O)R 10a 、S(O)2R11a NR 12a R 13a C(O)R 14a Compounds containing nitro, cyano, or hydrogen atoms.

[0507] [Method C40] In compound N of the present invention, R 5a and R 8a They may be the same or different from each other and are either halogen atoms or hydrogen atoms.

[0508] [Method C41] In compound N of the present invention, R 5a and R 8a Compounds containing hydrogen atoms.

[0509] [Method C42] In compound N of the present invention, R 5a and R 8a Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0510] [Method C43] A compound in which na is 0 in compound N of the present invention.

[0511] [Method C44] A compound in which na is 1 in compound N of the present invention.

[0512] [Method C45] Compound N of the present invention, wherein na is 2.

[0513] [Method C46] The compound N of the present invention, wherein qa is 1.

[0514] [Method C47] The compound N of the present invention, wherein qa is 2.

[0515] [Method C48] The compound N of the present invention, wherein qa is 3.

[0516] [Method C49] In compound N of the present invention, R 5a R 6a and R 8a Compounds containing hydrogen atoms.

[0517] [Method C50] In compound N of the present invention, R 2a and R 3a Compounds containing hydrogen atoms.

[0518] [Method C51] In compound N of the present invention, R 1a To have selected from group A a C2-C6 alkyl groups with one or more substituents, or having a group selected from C1-C6. a A methyl group with one or more substituents, R 2a and R 3aThe same or different from each other and consisting of a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be substituted by one or more halogen atoms, R 4a It is methyl, and may contain elements selected from group A. a C2-C6 chain hydrocarbon groups with one or more substituents, OR 23a , cyano, nitro or halogen atom, R 5a R 6a and R 8a Compounds containing hydrogen atoms.

[0519] Examples of compounds that can be used as compound E in this invention include the following compounds.

[0520] [Method E1] In compound E of the present invention, R 2b and R 3b Compounds containing hydrogen atoms.

[0521] [Method E2] In compound E of the present invention, R 2b and R 3b Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0522] [Method E3] In compound E of the present invention, R 2b and R 3b Compounds that are the same as 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.

[0523] [Method E4] In compound E of the present invention, R 2b and R 3b Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0524] [Method E5] In compound E of the present invention, X b For nitrogen atoms, R 4b To have selected from group F b The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. b C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents in OR 23b SR 24b S(O)R 25b 、S(O)2R 22b NR27b R 28b C(O)R 29b C(R) 30b ) = NOR 31b , cyano, nitro, hydroxyl, amino or halogen atom, R 6b It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b SR 9b S(O)R 10b 、S(O)2R 11b NR 12b R 13b C(O)R 14b Compounds containing nitro, halogen, or hydrogen atoms.

[0525] [Method E6] In compound E of the present invention, X b CR 5b R 4b To have selected from group F b The methyl, CH2F, CHF2 groups with one or more substituents may be selected from group A. b C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group with one or more substituents {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may have elements selected from group B} b The phenyl group contains one or more substituents, a phenyl group, or a 5-6 membered aromatic heterocyclic group. The phenyl group and the 5-6 membered aromatic heterocyclic group may have components selected from group D. b One or more substituents in OR 32b SR 24b S(O)R 25b 、S(O)2R 22b NR 27b R 28b C(O)R 29b C(R) 30b ) = NOR 31b , cyano, nitro, hydroxyl or halogen atom, R 6b It is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, and may have components selected from group B. b C3-C8 alicyclic hydrocarbon groups with one or more substituents, OR 7b Compounds containing nitro, fluorine, bromine, iodine, or hydrogen atoms.

[0526] [Method E7] In compound E of the present invention, R 6b A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0527] [Method E8] In compound E of the present invention, X b For CR 5b , R 6b Compounds consisting of fluorine, bromine, iodine, or hydrogen atoms.

[0528] [Method E9] In compound E of the present invention, X b For nitrogen atoms, R 6b Compounds consisting of halogen atoms or hydrogen atoms.

[0529] [Method E10] In compound E of the present invention, R 6b Compounds containing hydrogen atoms.

[0530] [Method E11] In compound E of the present invention, R 4b To have selected from group F b The methyl, CH2F, CHF2, or other substituents in the group may be selected from group A. b Compounds of C2-C3 chain hydrocarbon groups with one or more substituents.

[0531] [Method E12] In compound E of the present invention, R 4b Compounds containing halogen atoms.

[0532] [Method E13] In compound E of the present invention, R 4b To have selected from group F b The methyl group with one or more substituents may have a group selected from group A. b A compound consisting of a C2-C3 chain hydrocarbon group or a halogen atom with one or more substituents.

[0533] [Method E14] In compound E of the present invention, adjacent R 2b and R 4b Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) b Compounds with one or more substituents in the compound.

[0534] [Method E15] In compound E of the present invention, adjacent R 2b and R 4b Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). b Compounds with one or more substituents in the compound.

[0535] [Method E16] In compound E of the present invention, two adjacent R 4b and R 4bTogether with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) b Compounds with one or more substituents in the compound.

[0536] [Method E17] In compound E of the present invention, two adjacent R 4b and R 4b Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). b Compounds with one or more substituents in the compound.

[0537] [Method E18] In compound E of the present invention, R 5b and R 8b Compounds that are the same as 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.

[0538] [Method E19] In compound E of the present invention, R 5b and R 8b They may be the same or different from each other and are either halogen atoms or hydrogen atoms.

[0539] [Method E20] In compound E of the present invention, R 5b and R 8b Compounds containing hydrogen atoms.

[0540] [Method E21] In compound E of the present invention, R 5b and R 8b Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be replaced by one or more halogen atoms.

[0541] [Method E22] The compound E of the present invention in which nb is 0.

[0542] [Method E23] The compound E of the present invention, wherein nb is 1.

[0543] [Method E24] Compound E of the present invention, wherein nb is 2.

[0544] [Method E25] The compound E of the present invention, wherein qb is 1.

[0545] [Method E26] The compound E of the present invention, wherein qb is 2.

[0546] [Method E27] The compound E of the present invention, wherein qb is 3.

[0547] [Method E28] In compound E of the present invention, R5b R 6b and R 8b Compounds containing hydrogen atoms.

[0548] [Method E29] In compound E of the present invention, R 1b To have selected from group H b Compounds of phenyl groups with one or more substituents.

[0549] Group H b The group consisting of C1-C6 chain hydrocarbon groups, C1-C6 alkoxy groups (which may be substituted by one or more halogen atoms) and halogen atoms.

[0550] [Method E30] In compound E of the present invention, R 1b It is a compound in which a phenyl group can be replaced by one or more halogen atoms.

[0551] [Method E31] In compound E of the present invention, R 4b R is a C1-C3 chain hydrocarbon group or halogen atom. 2b R 3b R 5b R 6b and R 8b Compounds containing hydrogen atoms.

[0552] Examples of compounds that can be used as compound F in this invention include the following compounds.

[0553] [Method F1] In compound F of the present invention, R 1c To have the option to select from group B c Compounds of 3-8 membered nonaromatic heterocyclic groups with one or more substituents.

[0554] [Method F2] In compound F of the present invention, R 1c Compounds consisting of 3-8 membered non-aromatic heterocyclic groups that can be substituted by one or more halogen atoms.

[0555] [Method F3] In compound F of the present invention, R 1c For NR 33c R 34c Compounds.

[0556] [Method F4] In compound F of the present invention, R 1c For NR 33c R 34c , R 33c It is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 34c Compounds that are C1-C6 chain hydrocarbon groups or C3-C6 cycloalkyl groups.

[0557] [Method F5] In compound F of the present invention, R 2c and R 3c Compounds containing hydrogen atoms.

[0558] [Method F6] In compound F of the present invention, R 2c and R 3c Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0559] [Method F7] In compound F of the present invention, R 2c and R 3c Compounds that are the same as 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.

[0560] [Method F8] In compound F of the present invention, R 2c and R 3c Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0561] [Method F9] In compound F of the present invention, X c Compounds containing nitrogen atoms.

[0562] [Method F10] In compound F of the present invention, X c CR 5c Compounds.

[0563] [Method F11] In compound F of the present invention, R 6c A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0564] [Method F12] In compound F of the present invention, R 6c Compounds consisting of halogen atoms or hydrogen atoms.

[0565] [Method F13] In compound F of the present invention, R 6c Compounds containing hydrogen atoms.

[0566] [Method F14] In compound F of the present invention, R 4c To have selected from group A c Compounds of C1-C6 chain hydrocarbon groups with one or more substituents.

[0567] [Method F15] In compound F of the present invention, R 4c Compounds containing halogen atoms.

[0568] [Method F16] In compound F of the present invention, R 4c To have selected from group A cCompounds consisting of a C1-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0569] [Method F17] In compound F of the present invention, adjacent R 2c and R 4c Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) c Compounds with one or more substituents in the compound.

[0570] [Method F18] In compound F of the present invention, adjacent R 2c and R 4c Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). c Compounds with one or more substituents in the compound.

[0571] [Method F19] In compound F of the present invention, two adjacent R 4c and R 4c Together with the carbon atoms they are bonded to, they form C5-C6 alicyclic hydrocarbons or 5-6 membered non-aromatic heterocycles. (The C5-C6 alicyclic hydrocarbon and the 5-6 membered non-aromatic heterocycle may have elements selected from group B.) c Compounds with one or more substituents in the compound.

[0572] [Method F20] In compound F of the present invention, two adjacent R 4c and R 4c Together with the carbon atoms they are bonded to, they form a benzene ring or a 5-6 membered aromatic heterocycle (the benzene ring and the 5-6 membered aromatic heterocycle may have elements selected from group E). c Compounds with one or more substituents in the compound.

[0573] [Method F21] In compound F of the present invention, R 5c and R 8c Compounds that are the same as 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.

[0574] [Method F22] In compound F of the present invention, R 5c and R 8c Compounds that are the same or different from each other and consist of halogen atoms or hydrogen atoms.

[0575] [Method F23] In compound F of the present invention, R 5c and R 8c Compounds containing hydrogen atoms.

[0576] [Method F24] In compound F of the present invention, R5c and R 8c Compounds that are the same as or different from each other and are C1-C6 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be substituted by one or more halogen atoms.

[0577] [Method F25] The compound of the present invention in which nc is 0.

[0578] [Method F26] The compound F of the present invention, wherein nc is 1.

[0579] [Method F27] The compound F of the present invention, wherein nc is 2.

[0580] [Method F28] The compound F of the present invention, wherein qc is 1.

[0581] [Method F29] The compound F of the present invention, wherein qc is 2.

[0582] [Method F30] The compound F of the present invention, wherein qc is 3.

[0583] [Method F31] In compound F of the present invention, R 5c R 6c and R 8c Compounds containing hydrogen atoms.

[0584] [Method F32] In compound F of the present invention, X c CR 5c R 4c R is a C1-C3 chain hydrocarbon group or halogen atom. 2c R 3c R 5c R 6c and R 8c Compounds containing hydrogen atoms.

[0585] [Method F33] In compound F of the present invention, R 5c R 6c and R 8c Compounds that are the same or different from each other and consist of methyl, halogen or hydrogen atoms.

[0586] [Method F34] In compound F of the present invention, R 5c R 6c and R 8c Compounds containing hydrogen atoms.

[0587] [Method F35] In compound F of the present invention, R 1c It is a 4-6 member non-aromatic heterocyclic group or NR 33c R 34c R 33cIt is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a hydrogen atom, R 34c It is a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, X c CR 5c R 5c R 6c and R 8c For hydrogen atoms, nc is 2, R 4c To have selected from group A c Compounds consisting of a C1-C6 chain hydrocarbon group or a halogen atom with one or more substituents.

[0588] The following compounds can be cited as intermediate A.

[0589] [Method G1] In intermediate A, R 1d It is a propyl, butyl, cyclobutyl, cyclopentyl, or 5-6 membered aromatic heterocyclic group, X d Compounds containing bromine atoms.

[0590] [Method G2] In intermediate A, X 1d For CH or nitrogen atoms, nd is 1 or 2, R 1d Compounds that are propyl, butyl, cyclobutyl, cyclopentyl, or 5-6 membered aromatic heterocyclic groups.

[0591] [Method G3] In intermediate A, X 1d CH, nd is 1 or 2, R 1d Compounds consisting of propyl, butyl, cyclopentyl, and 5-6 membered aromatic heterocyclic groups.

[0592] [Method G4] In intermediate A, X 1d A compound with nitrogen atoms and nd = 2.

[0593] [Method G5] In intermediate A, X 1d nd and R 1d The combination of compounds is as follows:

[0594] X 1d CH, nd is 1 or 2, R 1d It is a combination of propyl, butyl, cyclobutyl, cyclopentyl, or 5-6 membered aromatic heterocycles; or,

[0595] X 1d For nitrogen atoms, nd is 1 or 2, R 1d It is a C2-C4 alkyl, C3-C6 alicyclic hydrocarbon group or a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group can be selected from group V} 1 A combination of one or more substituents in the group.

[0596] Next, the method for manufacturing compound Y (including compound Z of the present invention) will be described.

[0597] Manufacturing Method A

[0598] The compound shown in formula (Ib) (hereinafter referred to as compound (Ib)) or the compound shown in formula (Ic) (hereinafter referred to as compound (Ic)) can be prepared by reacting the compound shown in formula (Ia) (hereinafter referred to as compound (Ia)) with an oxidizing agent.

[0599] [Chemical Formula 26]

[0600]

[0601] In the formula, R 1X The symbols represent C1-C6 alkyl, C2-C6 ynyl (the C1-C6 alkyl and C2-C6 ynyl may have one or more substituents selected from group A), C2-C6 alkenyl (may have one or more substituents selected from group C), C3-C8 alicyclic hydrocarbon, 3-8 membered non-aromatic heterocyclic (the C3-C8 alicyclic hydrocarbon and 3-8 membered non-aromatic heterocyclic may have one or more substituents selected from group B), C6-C10 aryl (may have one or more substituents selected from group F), or 5-10 membered aromatic heterocyclic (may have one or more substituents selected from group D). Other symbols have the same meaning as above.

[0602] First, a method for producing compound (Ib) from compound (Ia) is described.

[0603] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of these.

[0604] Examples of oxidizing agents used in the reaction include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.

[0605] When using hydrogen peroxide as an oxidant, an alkali or catalyst can be added as needed.

[0606] Examples of bases used in reactions include sodium carbonate. When a base is used in a reaction, it is usually used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (Ia).

[0607] Examples of catalysts used in the reaction include sodium tungstate. When a catalyst is used in the reaction, it is typically used in a ratio of 0.01 to 0.5 moles relative to 1 mole of compound (Ia).

[0608] In the reaction, the oxidant is usually used in a ratio of 1 to 1.2 moles relative to 1 mole of compound (Ia).

[0609] The reaction temperature is typically in the range of -20 to 80°C. The reaction time is typically in the range of 0.1 to 12 hours.

[0610] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate), as needed. The organic layer is then dried and concentrated to obtain compound (Ib).

[0611] Next, a method for producing compound (Ic) from compound (Ib) is described.

[0612] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of them.

[0613] Examples of oxidizing agents used in the reaction include mCPBA and hydrogen peroxide.

[0614] When using hydrogen peroxide as an oxidant, an alkali or catalyst can be added as needed.

[0615] Examples of bases used in reactions include sodium carbonate. When a base is used in a reaction, it is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (Ib).

[0616] Examples of catalysts used in the reaction include sodium tungstate. When a catalyst is used in the reaction, it is typically used in a ratio of 0.01 to 0.5 moles relative to 1 mole of compound (Ib).

[0617] In the reaction, the oxidant is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (Ib).

[0618] The reaction temperature is typically in the range of -20 to 120°C. The reaction time is typically in the range of 0.1 to 12 hours.

[0619] After the reaction is complete, water is added to the reaction mixture, and extraction is performed using an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of an alkali (e.g., sodium bicarbonate), as needed. The organic layer is then dried and concentrated to obtain compound (Ic).

[0620] Alternatively, compound (Ic) can also be produced in a one-step reaction (one-pot process) by reacting compound (Ia) with an oxidizing agent.

[0621] The reaction can be carried out by using an oxidizing agent, typically in a ratio of 2 to 5 moles relative to 1 mole of compound (Ia), to produce compound (Ic) from compound (Ib).

[0622] Manufacturing method B

[0623] Compound (Ia) can be prepared by reacting the compound of formula (B1) (hereinafter referred to as compound (B1)) with the compound of formula (M1) (hereinafter referred to as compound (M1)) in the presence of a base.

[0624] [Chemical Formula 27]

[0625]

[0626] [In the formula, X] 51 [This symbol represents a chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, or trifuranyloxy group; other symbols have the same meaning as above.]

[0627] 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 dimethoxyethane (DME); halogenated hydrocarbons; amides such as dimethylformamide (DMF) and N-methylpyrrolidone (NMP); esters such as methyl acetate and ethyl acetate; nitriles; water; and mixtures of two or more of these.

[0628] Examples of bases 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); sodium hydride and tripotassium phosphate.

[0629] Metal catalysts and / or ligands may be used in the reaction as needed.

[0630] Examples of metal catalysts include copper catalysts such as copper iodide (I), copper bromide (I), copper chloride (I), copper oxide (I), copper trifluoromethanesulfonate (I) benzene complex, tetra(acetonitrile)copper hexafluorophosphate (I), and copper 2-thiophenecarboxylate (I); nickel catalysts such as bis(cyclooctadiene)nickel (O) and nickel chloride (II); and palladium catalysts such as palladium acetate, tris(dibenzylacetone)palladium (O), tetra(triphenylphosphine)palladium (O), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (II). 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 (B1).

[0631] Examples of ligands 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, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, N,N'-dimethylethylenediamine, and N,N-dimethylglycine hydrochloride. When using ligands in a reaction, the ligand is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (B1).

[0632] In the reaction, compound (M1) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B1), and the base is usually used in a ratio of 1 to 10 moles.

[0633] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–48 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, thereby separating compound (Ia).

[0635] The compound (M1) is known or can be manufactured using known methods.

[0636] Manufacturing method C

[0637] The compound shown in formula (I) can 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.

[0638] [Chemical Formula 28]

[0639]

[0640] [In the formula, X] 52 M represents a chlorine atom, bromine atom, iodine atom, or trifuranyloxy group. 1 This represents B(OH)₂ or 4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl; other symbols have the same meaning as above.

[0641] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, dimethyl sulfoxide (hereinafter referred to as DMSO), water, and mixtures of two or more of them.

[0642] Examples of palladium catalysts used in the reaction include palladium(II) acetate and [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[0643] Examples of bases used in reactions include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium fluoride, and tripotassium phosphate.

[0644] In the reaction, compound (M2) is typically used in a ratio of 0.5 to 2 moles relative to 1 mole of compound (B2), 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.

[0645] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–120 hours.

[0646] 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 enabling the separation of the compound represented by formula (I).

[0647] The compound (M2) is known or can be manufactured using known methods.

[0648] Manufacturing method D

[0649] The compound shown in formula (I) can be prepared 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)) in the presence of a palladium catalyst and a base.

[0650] [Chemical Formula 29]

[0651]

[0652] [In the formula, the symbols have the same meaning as in the preceding text.]

[0653] In the reaction, compound (B3) can be used instead of compound (B2), and compound (M3) can be used instead of compound (M2), in accordance with manufacturing method C.

[0654] The compound (M3) is known or can be manufactured using known methods.

[0655] Manufacturing method E

[0656] Compound (Ia) can be prepared by reacting the compound of formula (B4) (hereinafter referred to as compound (B4)) with the compound of formula (M4) (hereinafter referred to as compound (M4)) in the presence of a base.

[0657] [Chemical Formula 30]

[0658]

[0659] [In the formula, X] 53 This symbol represents a fluorine atom, chlorine atom, bromine atom, iodine atom, methanesulfonyloxy group, or trifuranyloxy group; other symbols have the same meaning as above.

[0660] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, amides, water, and mixtures of two or more of them.

[0661] Examples of bases used in reactions include alkali metal hydrides, alkali metal carbonates, organic bases, sodium hydride, and tripotassium phosphate.

[0662] In X 53 In the case of bromine atoms, iodine atoms, or trifuranyloxy groups, metal catalysts and ligands can be added as needed.

[0663] 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 (B4).

[0664] 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 (B4).

[0665] In the reaction, compound (M4) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B4), and the base is usually used in a ratio of 1 to 10 moles.

[0666] 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.

[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 to obtain compound (Ia).

[0668] The compound (M4) is known or can be manufactured using known methods.

[0669] Manufacturing method F

[0670] Compound (Ic) can be produced by reacting compound (B4) with the compound shown in formula (M5) (hereinafter referred to as compound (M5)).

[0671] [Chemical Formula 31]

[0672]

[0673] [In the formula, the symbols have the same meaning as in the preceding text.]

[0674] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, nitriles, DMSO, water, and mixtures of two or more of them.

[0675] In the reaction, compound (M5) is usually used in a ratio of 1 to 3 moles relative to 1 mole of compound (B4).

[0676] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–48 hours.

[0677] 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 enabling the separation of compound (Ic).

[0678] The compound (M5) is known or can be manufactured using known methods.

[0679] Manufacturing method G

[0680] The compound represented by formula (Id) (hereinafter referred to as compound (Id)) can be produced by heating the compound represented by formula (B5) (hereinafter referred to as compound (B5)).

[0681] [Chemical Formula 32]

[0682]

[0683] [In the formula, the symbols have the same meaning as in the preceding text.]

[0684] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, alcohols, nitriles, ethers, esters, aromatic hydrocarbons, halogenated hydrocarbons, amides, DMSO, water, and mixtures of two or more of them.

[0685] The reaction temperature is typically in the range of 80℃ to 200℃. The reaction time is typically in the range of 0.1 to 24 hours.

[0686] 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 (Id).

[0687] Compound (B5) is known or can be manufactured according to the methods described in this specification or known methods.

[0688] Manufacturing method H

[0689] The compound represented by formula (Ie) (hereinafter referred to as compound (Ie)) can be prepared by reacting the compound represented by formula (B6) (hereinafter referred to as compound (B6)) with the compound represented by formula (M6) (hereinafter referred to as compound (M6)) in the presence of a base.

[0690] [Chemical Formula 33]

[0691]

[0692] In the formula, R 33X and R 34X"Identical" or "different" indicates that it may have a C1-C6 chain hydrocarbon group with one or more substituents selected from group G, a C3-C6 alicyclic hydrocarbon group with one or more halogen atoms, or a hydrogen atom. R 33X and R 34X These can form, together with the nitrogen atoms they are bonded to, 5-10 membered aromatic heterocycles, C3-C8 alicyclic hydrocarbons, or 3-8 membered non-aromatic heterocycles having one or more substituents selected from group D {the C3-C8 alicyclic hydrocarbon and the 3-8 membered non-aromatic heterocycle may have one or more substituents selected from group B}, with other symbols having the same meaning as above.

[0693] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixtures of two or more of them.

[0694] Examples of bases used in reactions include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium hydride, and tripotassium phosphate.

[0695] In the reaction, compound (M6) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (B6), and the base is usually used in a ratio of 1 to 10 moles.

[0696] The reaction temperature is typically in the range of 0–150°C. The reaction time is typically in the range of 0.1–48 hours.

[0697] 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 (Ie).

[0698] The compound (M6) is known or can be manufactured using known methods.

[0699] Reference manufacturing method A

[0700] Compound (B1) can be produced by reacting compound (B4) with a vulcanizing agent.

[0701] [Chemical Formula 34]

[0702]

[0703] [In the formula, the symbols have the same meaning as in the preceding text.]

[0704] In the reaction, hydrogen sulfide or other sulfiding agents can be used instead of compound (M4), and the reaction can be carried out according to manufacturing method E.

[0705] Reference manufacturing method B

[0706] Compound (B4) can be prepared by reacting the compound of formula (C1) (hereinafter referred to as compound (C1)) with compound (M2) in the presence of a palladium catalyst and a base.

[0707] [Chemical Formula 35]

[0708]

[0709] [In the formula, the symbols have the same meaning as in the preceding text.]

[0710] In the reaction, compound (C1) can be used instead of compound (B2), and the reaction can be carried out according to manufacturing method C.

[0711] The compound (C1) is known or can be manufactured using known methods.

[0712] Reference manufacturing method C

[0713] The compound represented by formula (C3) (hereinafter referred to as compound (C3)) can be prepared by reacting the compound represented by formula (C2) (hereinafter referred to as compound (C2)) with compound (M1) in the presence of a base.

[0714] [Chemical Formula 36]

[0715]

[0716] [In the formula, the symbols have the same meaning as in the preceding text.]

[0717] In the reaction, compound (C2) can be used instead of compound (B1) and carried out according to manufacturing method B.

[0718] The compound (C2) is known or can be manufactured using known methods.

[0719] Reference manufacturing method D

[0720] The compound represented by formula (C4) (hereinafter referred to as compound (C4)) or the compound represented by formula (C5) (hereinafter referred to as compound (C5)) can be prepared by reacting compound (C3) with an oxidizing agent.

[0721] [Chemical Formula 37]

[0722]

[0723] [In the formula, the symbols have the same meaning as in the preceding text.]

[0724] In the reaction, compound (C3) can be used instead of compound (Ia), and compound (C4) can be used instead of compound (Ib), in accordance with manufacturing method A.

[0725] Reference manufacturing method E

[0726] The compound shown in formula (C6) (hereinafter referred to as compound (C6)) can be prepared by reacting compound (B2) with bis(pinacol)diboron in the presence of a base and a palladium catalyst.

[0727] [Chemical Formula 38]

[0728]

[0729] [In the formula, the symbols have the same meaning as in the preceding text.]

[0730] In the reaction, bis(pinacol)diboron can be used instead of compound (M2), and the reaction is carried out according to manufacturing method C.

[0731] Reference manufacturing method F

[0732] The compound shown in formula (C7) (hereinafter referred to as compound (C7)) can be produced by reacting compound (C1) with compound (M5).

[0733] [Chemical Formula 39]

[0734]

[0735] [In the formula, the symbols have the same meaning as in the preceding text.]

[0736] In the reaction, compound (C1) can be used instead of compound (B4), and the reaction is carried out according to manufacturing method F.

[0737] Reference manufacturing method G

[0738] The compound represented by formula (C9) (hereinafter referred to as compound (C9)) can be produced by heating the compound represented by formula (C8) (hereinafter referred to as compound (C8)).

[0739] [Chemical Formula 40]

[0740]

[0741] [In the formula, the symbols have the same meaning as in the preceding text.]

[0742] In the reaction, compound (C8) can be used instead of compound (B5), and the reaction is carried out according to manufacturing method G.

[0743] The compound (C8) is known or can be manufactured using known methods.

[0744] Reference manufacturing method H

[0745] Compound (B6) can be produced from the compound represented by formula (C10) (hereinafter referred to as compound (C10)).

[0746] [Chemical Formula 41]

[0747]

[0748] [In the formula, X] 55 This represents SH or S(O)₂OH; other symbols have the same meaning as described above.

[0749] The reaction can be carried out according to, for example, the methods described in International Publication No. 2016 / 204096, Tetrahedron Letters, 2017, 58, 2244-2247, etc.

[0750] The compound (C10) is known or can be manufactured using known methods.

[0751] The compound of the present invention or compound Z of the present invention may be used in combination or mixed 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.

[0752] The aforementioned combination or use refers to using the compound of the present invention or compound Z of the present invention with the present ingredient simultaneously, separately or at intervals.

[0753] When the compound of the present invention or compound Z of the present invention is used simultaneously with the ingredient, the compound of the present invention or compound Z of the present invention and the ingredient may be contained in separate formulations or in the same formulation.

[0754] 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 thereof), and the compounds of the present invention.

[0755] 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 compound Z of the present invention (hereinafter referred to as composition A).

[0756] 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, ranitidine 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.

[0757] 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., phenylaminopyridine fungicides), signal transduction inhibitors, lipid 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.

[0758] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0759] Group (d) is the group containing the repellent component.

[0760] The following describes examples of combinations of this component with compound Z of the present invention (which includes compounds of the present invention). For example, alanycarb + SX refers to the combination of alanycarb and SX.

[0761] It should be noted that the abbreviation SX refers to any one of the compounds Z of this invention selected from compound groups SX1 to SX210. 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 indicate CAS RN (registered trademark).

[0762] The combination of the component of group (a) above with compound Z of the present invention:

[0763] 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, Bendiocorb + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid acid) + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphidePhosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride Hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chlorpicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chlorafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanavalin AA) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, cyprofen flanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, dizinon + SX, dichlorvos + SX, diloromezotiazine + 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 Dryopterisfilix-mas)+SX, emamectin-benzoate+SX, empenthrin+SX, endosulfan+SX, EPN (O-ethyl O-(4-nitrophenyl)phenylphosphonothioate)+SX, epsilon-metofluthrin+SX, epsilon-momfluorothrin+SX, esfenvalerate+SX, ethiofencarb+SX, ethion+SX, etiprole+SX, ethoprophos+SX, etofenprox+SX, etoxazole+SX, extract of Artemisia absinthium+SX, neem extract Azadirachta indica + SX, Cassia nigricans extract + SX, Butterfly pea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tanacetum vulgare extract + SX, Urtica dioica extract + SX, Viscum album extract + SX, Famphur + SX, Fenamiphos + SX, Fenazaquin + SX, Fenbutatinoxide)+SX, fenitrothion+SX, fenmezoditiaz+SX, fenobucarb+SX, fenoxycarb+SX, fenpropathrin+SX, fenpyroximate+SX, fenthion+SX, fenvalerate+SX, fipronil+SX, 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

[0764] 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, isoprocarb+SX, O-(methoxyaminothiophosphoryl)salicylic acid isopropyl (isopropyl-O-(me Thoxyaminothiophosphoryl salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilane + SX, lufenuron + SX, machine oiloil)+SX, malathion+SX, mecarbam+SX, meperfluthrin+SX, metaflumizone+SX, metam+SX, methamidophos+SX, methidathion+SX, methiocarb+SX, metomyl+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, Phosm et)+SX, phosphamidon+SX, phosphine+SX, phoxim+SX, pirimicarb+SX, pirimiphos-methyl+SX, prallethrin+SX, profenofos+SX, profluthrin+SX, propargite+SX, propetamphos+SX, propoxur+SX, propylene glycol alginate glycolalginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, pyraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyri... minostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borateBorate + SX, Sodium Metaborate + SX, Spidoxamat + SX, Spinetoram + SX, Spinosad + SX, Spirobudifen + SX, Spirodiclofen + SX, Spiomesifen + SX, Spiropidion + SX, Spiotetramat + SX, Sulfiflumin + SX, Sulfuramid + SX, Sulfotep + SX, Sulfoxaflor + SX, Sulfur + SX, Sulfurylfluoride + SX, Tartar emetic)+SX, tau-fluvalinate+SX, tebufenozide+SX, tebufenpyrad+SX, tebupirimfos+SX, teflubenzuron+SX, tefluthrin+SX, temephos+SX, terbufos+SX, terpene constituents of the extract of chenopodium ambrosioides nearambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-disodium + SX, thiosultap-disodium + SX, thiosultap-disodium + SX ultap-monosodium)+SX, tigolaner+SX, tiorantraniliprole+SX, tioxazafen+SX, tolfenpyrad+SX, tralomethrin+SX, transfluthrin+SX, triazamate+SX, triazophos+SX, trichlorfon+SX, trifluenfuronate+SX, triflumezopyrim+SX, triflumuron+SX, trimethacarb+SX, tyclopyrazoflor+SX, umifoxolaner+SX, vamidothion+SX, wood extract of the nanmu tree (wood) Extract of Quassia amara) + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX,

[0765] 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,

[0766] BT crop protein Cry1Ab + SX, BT crop protein Cry1Ac + SX, BT crop protein Cry1Fa + SX, BT crop protein Cry1A.105 + SX, BT crop protein Cry2Ab + SX, BT crop protein Vip3A + SX, BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 (BT crop protein) Cry34Ab1 / Cry35Ab1)+SX, Tea Leaf Roller Granulovirus BV-0001 (Adoxophyes orana granulosis virus strain BV-0001)+SX, Soybean Noctuid Moth Nucleopolyhedrovirus (Anticarsia gemmatalis mNPV)+SX, Alfalfa Silver-striped Noctuid Moth Nucleopolyhedrovirus (Autographa californica mNPV)+SX, Codling Moth Granulovirus V15 (Cydia pomonella GVstrain V15)+SX, Codling Moth Granulovirus V22 (Cydia pomonella GV strain V22)+SX, Apple Helicoverpa granulovirus (Cryptophlebia leucotreta GV)+SX, Pine Caterpillar Cypovirus (Dendrolimus punctatus cypovirus)+SX, Cotton Bollworm Nucleopolyhedrovirus BV-0003 (Helicoverpa Armigera NPV strain BV-0003+SX, Helicoverpazea NPV+SX, Lymantria dispar NPV+SX, Mamestra brassicae NPV+SX, Mamestra brassicae NPV+SX, and Mamestra brassicae NPV+SX.The following are listed: configurata NPV+SX, balsam fir sawfly nucleopolyhedrovirus (Neodiprion abietis NPV+SX), red pine sawfly nucleopolyhedrovirus (Neodiprion lecontei NPV+SX), pine yellow sawfly nucleopolyhedrovirus (Neodiprionsertifer NPV+SX), locust microsporidia (Nosema locustae)+SX, yellow fir tussock moth nucleopolyhedrovirus (Orgyia pseudotsugata NPV+SX), cabbage white butterfly granulovirus (Pieris rapae GV+SX), Indian meal moth granulovirus (Plodia interpunctella GV+SX), beet armyworm nucleopolyhedrovirus (Spodopteraexigua mNPV+SX), sea gray winged moth nucleopolyhedrovirus (Spodoptera littoralis mNPV+SX), and beet armyworm nucleopolyhedrovirus (Spodoptera liturata NPV+SX). NPV)+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637+SX, Bacillus megaterium+SX, Bacillus sp. strain AQ175+SX, Bacillus sp. strain AQ177+SX, Bacillus sp. strain AQ178+SX, Bacillus sphaericus strain 2362 serotype H5a5b 2362serotypeH5a5b)+SX, Bacillus sphaericus strain ABTS1743+SX, Bacillus thuringiensis strain AQ52+SX, Bacillus thuringiensis strain BD#32BD#32)+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawaistrain NB200+SX, Bacillus thuringiensis subsp. Aizawaistrain serotype H-7 (Bacillus thuringiensis subsp. Aizawaistrain serotype H-7). The following strains were found to be infected with Bacillus thuringiensis subsp. Aizawai Serotype strain H-7+SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348+SX, and Bacillus thuringiensis subsp. Kurstaki strain EG7841. EG7841)+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19+SX, Bacillus thuringiensis subsp. Kurstaki strain F810F810)+SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1+SX, Bacillus thuringiensis subsp. Kurstaki strain PB54+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Tenebriosis strain MPPL002 The following strains of Bacillus thuringiensis were tested: subsp. Thuringiensis strain MPPL002+SX, subsp. Morrisoni, var. Colmeri, var. Darmstadiensis strain 24-91, var. dendrolimus, var. galleriae, and strain Bacillus thuringiensis var. israelensis. BMP144)+SX, Bacillus thuringiensis var. israelensis serotype strain H-14)+SX, Bacillus thuringiensis var. japonicusstrains of *Bacillus thuringiensis* var. *sandiego* strain M-7 + SX, strains of *Bacillus thuringiensis* var. 7216 + SX, strains of *Bacillus thuringiensis* var. *aegypti* + SX, strains of *Bacillus thuringiensis* var. *T36* + SX, strains of *Beauveria bassiana* ANT-03 + SX, strains of *Beauveria bassiana* ATCC74040 + SX, strains of *Beauveria bassiana* GHA + SX, strains of *Beauveria* var. *bryophyte* The following bacteria were tested: *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, *Lagenidium giganteum* + SX, *Lecanicillium lecanii* strain KV01 + SX, and conidia of *Lecanicillium lecanii* strain DAOM198499. DAOM198499)+SX, conidia of strain DAOM216596 of *Verticillium lecanii* (conidia of strain DAOM216596)+SX, strain Ve6+SX of *Lecanicillium muscarium*, strain F52 of *Metarhizium anisopliae* (*Metarhizium anisopliae* strain)F52)+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52+SX, Metarhizium flavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomyces fumosoroseus Apopka strain 97+SX, Paecilomyces lilacinus strain 251+SX, Paecilomyces tenuipes strain T1+SX, Paenibacillus popilliae+SX, Pasteurium Pn1 strain The strains are: nishizawaestrain Pn1)+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecani strain NCIM1312+SX, and Wolbachia pipientis+SX.

[0767] The combination of this component of group (b) above with compound Z of the present invention:

[0768] 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 The following are listed: mixture + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX, colletochlorinB+SX, Copper(II)acetate+SX, Copper(II)hydroxide+SX, Copper(II)chloride+SX, Copper(II)sulfate+SX, Coumoxystrobin+SX, Cyazofamid+SX, Cyflufenamid+SX, Cymoxanil+SX, Cyproconazole+SX, Cyprodinil+SX, Dichlobentiazox+SX, Dichlofluanid+SX, Diclomezine+SX, Diclomezine+SX, Dicloramide an)+SX, diethofencarb+SX, difenoconazole+SX, diflumetorim+SX, dimethachlone+SX, dimethirimol+SX, dimethomorph+SX, dimoxystrobin+SX, diniconazole+SX, diniconazole-M+SX, dinocap+SX, dipotassium hydrogen phosphite+SX, dipymetitrone+SX, dithianon+SX, dodecylbenzenesulphonic bis(ethylenediamine)copper(II) complex salt acid bisethylenediamine copper(II)salt)+SX, dodemorph+SX, dodine+SX, edifenphos+SX, enoxastrobin+SX, epoxiconazole+SX, etaconazole+SX, ethaboxam+SX, ethirimol+SX, etridiazole+SX, extract of Melaleuca alternifolia+SX, extract of Reynoutriasachalinensis extract + SX, lupine cotyledon extract + SX, allium sativum extract + SX, equisetum arvense extract + SX, nasturtium extract + SX of Tropaeolummajus + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, fenfuram + SX, fenhexamid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, fentin acetate + SX, fentin chloride + SX, fentin...Hydroxide + SX, 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, Fluofluoxapiprolin + SX, Fluoxastrobin +SX, fluoxytioconazole +SX, fluquinconazole +SX, flusilazole +SX, flusulfamide +SX, flutianil +SX, flutolanil +SX, flutriafol +SX, fluxapyroxad +SX, folpet +SX, fosetyl +SX, fosetyl-aluminium +SX, furberidazole +SX, furalaxyl +SX, furametpyr +SX, guazatine +SX, hexaconazole +SX, hymexazole +SX

[0769] 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, isoprothiolane + 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, penthiophanate + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium bicarbonate + 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, pyraclostrobin + SX, pyramet ostrobin+SX, pyraoxystrobin+SX, pyrapropoyne+SX, pyraziflumid+SX, pyrazophos+SX, pyribencarb+SX, pyributicarb+SX, pyridachlometyl+SX, pyrifenox+SX, pyrimethanil+SX, pyrimorph+SX, pyriofenone+SX, pyrisoxazole+SX, pyroquilon+SX, Quillaja extract 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

[0770] 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-methylformamidin (2101814-55-3)+SX、N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidin (181782) 8-69-5)+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-nitropyridin-2-amine (1446247-98-8)+SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl 1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4)+SX, (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2)+SX, (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol4-Triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6)+SX, (1R,2S,5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4)+SX, (1S,2R,5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5)+SX, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-yl) Methyl cyclopentane-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 (2019215-86-0)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazolium-5-carboxylonitrile (2018316-13-5) )+SX、1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile (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-dimethylpent-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl)}amino)-6-methylpyrimidine (1605340-92-8)+SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9)+SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5)+SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098) 918-25-1)+SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098918-26-2)+SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)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-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-di ...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-(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]ethy l N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethylN-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]eth yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanina te)+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)acetamide +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-Oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)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)morpholin-3-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one+SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one +SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azacycloheptan-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-carboxylic acid ethyl ester+SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester+SX,4-Oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N,N-di ... [diazol-3-yl]phenylmethyl)-1H-1,2,4-triazol-3-amine + SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + SX, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate + 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] Ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate +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-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,[2-Difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3,4]oct-1-yl)-5-methylthiazole-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide +SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole -4-Carboxamide +SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2-methylpropionyl)(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-(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-(2,6-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-difluorophenyl)cyclopropyl]oxy}pyrimidin + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-Oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6 -Dihydro-4H-1,2,4-oxadiazine +SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine +SX, 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-dimethylpropionamide + 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}propane-2-yl)-2-methylpropionamide + S X, N-((2S)-1-{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,

[0771] 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 The following strains of Bacillus amyloliquefaciens were tested: 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, and 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 strain MA342 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, Pseudozymaflocculosa PF-A22UL strain + SX, Pseudomonas rhodesiaestrain HAI-0804 strain + SX, Pythium oligandrum strain DV74 strain + SX, Pythium oligandrum strain M1 strain + SX, Streptomyces griseoviridis strain K61 strainK61)+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 atrovirides* 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, *Trichoderma gamsii* endophytic fungus ICC080 strain 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, Trichoderma viride+SX, Variovorax paradoxus strain CGF4526+SX, Harpinprotein+SX.

[0772] The combination of this component of group (c) above with compound Z of the present invention:

[0773] 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 falfya+SX meliloti)+SX, Zucchini Yellow Mosaik Virus weak strain+SX.

[0774] The combination of the component of group (d) above with compound Z of the present invention:

[0775] Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0776] The ratio of compound Z to the present component is not particularly limited, but examples of weight ratios (compound of the present invention: the present component) 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.

[0777] This compound, compound Y, compound Z, or composition A 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, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specifically, the following examples can be cited. The scientific names of the plant pathogenic microorganisms causing each disease are shown in parentheses.

[0778] Rice diseases: Blight (Pyricularia oryzae), Sesame leaf blight (Cochliobolus miyabeanus), Sheath blight (Rhizoctonia solani), Bakanae disease (Gibberella fujikuroi), Yellowing and stunting disease (Sclerophthora macrospora), Pseudo-rice blast and panicle blight (Epicoccum nigrum), Seedling blight (Trichodermaviride, Rhizopus oryzae), False sheath blight (Waiteacircinata), Brown sclerotinia (Ceratobasidium setariae), Brown sheath blight (Thanatephorus). cucumeris), rice false smut (Ustilaginoidea virens), grain smut (Tilletia horrida, Tilletia barclayana);

[0779] 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 of snow rot (Typhula incarnata, Typhula ishikariensis), Large sclerotium rot of snow rot (Sclerotinia northernis) The following diseases are associated with wheat diseases: brown snow rot (Pythium spp.), loose smut (Ustilagotritici), 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), damping-off (Gaeumannomyces graminis), and blast disease (Pyricularia graminis-tritici).

[0780] 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), Smut (Ustilago nuda), Cloud blight (Rhynchosporium secalis), Net blight (Pyrenophora teres), Leaf spot (Cochliobolus sativus), Leaf stripe (Pyrenophora sclerotiorum). graminea), Ramularia collo-cygni leaf spot, and Rhizoctonia solani (a fungus causing seedling damping-off).

[0781] 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), Dark coccidioides leaf spot (Phaeosphaeria maydis), Two-spore rot (Stenocarpella maydis, Stenocarpellamacrospora), Stem rot (Fusarium graminii). graminearum), Fusarium verticilioides, Colletotrichum graminicola, Ustilago maydis (corn smut), Physoderma maydis (corn rot), and Phyllachora maydis (corn black spore causal agent).

[0782] Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternaria gossypii), Root black rot (Thielaviopsis basicola).

[0783] Coffee diseases: Rust (cafe rust fungus (Hemileia vastatrix)), leaf spot (Cercospora coffeicola));

[0784] Diseases of rapeseed: Sclerotinia sclerotiorum, Alternaria brassicae, Phona lingam, Pyrenopeziza brassicae;

[0785] Sugarcane diseases: Rust (Puccinia melanocephela, Pucciniakuehnii), Smut (Ustilago scitaminea);

[0786] Sunflower diseases: Rust (Puccinia helianthi), downy mildew (Plasmopara halstedii);

[0787] Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), penicillin rot (Penicillium digitatum), penicillin disease (Penicillium italicum), blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;

[0788] Apple diseases: Blossom rot (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria alternata (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), blight (Phytophthora cactorum), red spot (Gymnosporangium). juniperi-virginianae), Gymnosporangium yamadae);

[0789] Pear diseases: Black spot (Venturia nashicola, Venturiapirina), Black spot (Alternaria alternata Japanese pearpathotype), Gymnosporangium haraeanum (Gymnosporangium haraeanum);

[0790] Peach diseases: Gray spot (Monilinia fructicola), Black spot (Cladosporium carpophilum), Brown spot (Phomopsis sp.), Leaf curl (Taphrina deformans), Powdery mildew (Podosphaeraleucotricha).

[0791] Grape diseases: Black rot (Elsinoe ampelina), Late rot (Glomerella cingulata, Colletotrichum acutatum), Powdery mildew (Uncinula necator), Rust (Neophysopella sp.), Black rot (Guignardia bidwellii), Downy mildew (Plasmopara viticola), Brown spot (Pseudocercospora vitis), White rot (Coniella castaneicola);

[0792] Diseases of persimmon: Anthracnose (Gloeosporium kaki, Colletotrichum acutatum), Leaf spot (Cercospora kaki, Mycosphaerella nawae), Brown spot (Pseudocercospora vitis), White rot (Coniella castaneicola), Powdery mildew (Phyllactiniakakicola);

[0793] Fig diseases: Rust (Phakopsora nishidana)

[0794] Diseases of gourds: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Gynostemma pentaphyllum (Didymella bryoniae), Brown spot (Corynespora cassiicola), Fusarium wilt (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Phytophthora capsici, Damping-off (Pythium sp.), Phopsis sp. root rot;

[0795] Tomato diseases: Ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), anthracnose (Pseudocercospora fuligena), blight (Phytophthora infestans), powdery mildew (Leveillula taurica);

[0796] Eggplant diseases: Brown spot (Phomopsis vexans)), powdery mildew (Erysiphe cichoracearum)), black rot (Corynespora melongenae)), leaf mold (Mycovellosiella nattrassii)), brown spot (Thanatephorus cucumeris);

[0797] Diseases of cruciferous vegetables: Black spot (Alternaria japonica), White spot (Cercosporella brassicae), Clubroot (Plasmodiophorabrassicae), Downy mildew (Peronospora parasitica), White rust (Albugocandida), Black mold (Alternaria brassicicola);

[0798] 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).

[0799] Soybean diseases: Purple blotch (Cercospora kikuchii), Black rot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. sojae), Rust (Phakopsora pachyrhizi), Brown ring rot (Corynespora cassiicola), Anthracnose (Colletotrichum glycines, Colletotrichum truncatum), Damping-off (Rhizoctonia solani), Brown spot (Septoria glycines), Spot disease (Cercospora sojina), Sclerotinia rot (Sclerotinia sclerotiorum). sclerotiorum), 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);

[0800] Diseases of common beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular leaf spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), and root rot (Fusarium solani).

[0801] Peanut diseases: Black spot (Cercospora personata) , Brown spot (Cercospora arachidicola) , White rot (Sclerotium rolfsii) , Red crown rot (Calonectria ilicicola) ;

[0802] Pea diseases: powdery mildew (Erysiphe pisi) and root rot (Fusarium solani).

[0803] Potato diseases: Early blight (Alternaria solani)), blight (Phytophthora infestans)), red 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);

[0804] Strawberry diseases: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum);

[0805] Tea diseases: Net cake disease (Exobasidium reticulatum), white spot disease (Elsinoe leucospila), gray blight (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis);

[0806] Tobacco diseases: Red spot disease (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), blight (Phytophthora nicotianae);

[0807] Diseases of sugar beets: Brown spot (Cercospora beticola)), Leaf blight (Thanatephorus cucumeris)), Root rot (Thanatephorus cucumeris)), Black root rot (Aphanomyces cochlioides)), Rust (Uromyces betae);

[0808] Diseases of roses: Black spot (Diplocarpon rosae) and powdery mildew (Sphaerotheca pannosa);

[0809] Chrysanthemum diseases: Brown spot (Septoria chrysanthemi-indici) and white rust (Puccinia horiana).

[0810] Onion diseases: Botrytis leaf blight (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa, Botrytis allii, Botrytis squamosa);

[0811] 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).

[0812] Radish diseases: Black spot (Alternaria brassicicola);

[0813] Sweet potato diseases: vine rot (Fusarium oxysporum f.sp.batatas), basal rot (Diaporthedestruens), black spot (Ceratocystis fimbriata);

[0814] Diseases of turfgrass: Coin spot (Sclerotinia homoeocarpa), brown patch, large patch (Rhizoctonia solani), Pythium wilt (Pythium aphandidermatum), anthracnose (Colletotrichum caudatum);

[0815] Banana diseases: Banana leaf spot (Sigatoka disease) (Mycosphaerella fijiensis, Mycosphaerella musicola));

[0816] Diseases of lentils: Ascochyta disease (Ascochyta lentis);

[0817] Chickpea diseases: Ascochyta rabiei (blight);

[0818] Diseases of green peppers: Anthracnose (Colletotrichum scovillei) , Powdery mildew (Leveillula taurica) , White mold (Sclerotium rolfsii) ;

[0819] Mango diseases: Anthracnose (from the polyprotic plant anthracnose fungus Colletotrichum acutatum);

[0820] Sweet potato diseases: basal rot (Diaporthe destruens);

[0821] Fruit tree diseases: White root rot (Rosellinia necatrix) and purple root rot (Helicobasidium mompa);

[0822] Post-harvest diseases of fruits such as apples and pears: Mucor rot diseases (Mucorpiriformis);

[0823] 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;

[0824] Viral diseases: Giant vein disease of lettuce mediated by Olpidium brassicae; and various viral diseases of crops mediated by Polymyxa species (e.g., Polymyxa betae and Polymyxa graminis).

[0825] 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)

[0826] 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.

[0827] 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 compound, compound Y, the present invention compound, compound Z, or composition A. Examples of treatment methods include foliar treatment, soil treatment, and seed treatment.

[0828] For this compound, compound Y, compound Z, or composition A, it is typically mixed with inactive carriers such as solid or liquid carriers and surfactants, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate aqueous suspensions, oil suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, water-dispersible granules, powders, or pellets for use. 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.

[0829] These formulations typically contain 0.0001 to 99% by weight of the present compound, compound Y, compound Z, or composition A.

[0830] Examples of solid carriers include clay (pyrophyllite clay, kaolin 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.).

[0831] 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.).

[0832] 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.).

[0833] Examples of adjuvants used in other formulations include binders, dispersants, colorants, and stabilizers. Specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), isopropyl phosphate, and butylated hydroxytoluene.

[0834] In addition, adjuvants may be used as components that enhance or assist the efficacy of this compound, compound Y, compound Z 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).

[0835] 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.

[0836] 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.

[0837] Seedlings include seedlings and saplings.

[0838] As a method for preventing plant diseases by applying an effective amount of the present compound, compound Y, compound Z, or composition A to the soil, examples include applying an effective amount of the present compound, compound Y, compound Z, or composition A to the soil before or after transplanting the plants. More specifically, examples include: planting hole treatment (planting hole distribution, planting hole 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), and 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).

[0839] Examples of seed treatment include treatments of seeds or vegetative reproductive organs using compounds of this invention, compound Y, compound Z, or composition A. More specifically, examples include: spraying treatment by atomizing a suspension of compounds of this invention, compound Y, compound Z, or composition A and spraying it onto the surface of the seed or vegetative reproductive organ; coating treatment by applying compounds of this invention, compound Y, compound Z, or composition A to the seed or vegetative reproductive organ; immersion treatment by immersing the seed or vegetative reproductive organ in a solution of compounds of this invention, compound Y, compound Z, or composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs using a carrier containing compounds of this invention, compound Y, compound Z, or composition A (coating treatment, granule coating treatment, etc.). Seed potatoes are a particularly good example of the aforementioned vegetative reproductive organ.

[0840] In this invention, a seed or vegetative reproductive organ that retains this compound, compound Y, compound Z, or composition A refers to a seed or vegetative reproductive organ in which this compound, compound Y, compound Z, or composition A is attached to its surface. Regarding the aforementioned seed or vegetative reproductive organ that retains this compound, compound Y, compound Z, or composition A, materials other than this compound, compound Y, compound Z, or composition A may be attached before or after attaching this compound, compound Z, or composition A to the seed or vegetative reproductive organ.

[0841] 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.

[0842] Seeds or vegetative reproductive organs containing this compound, compound Y, compound Z of the present invention, or composition A can be obtained, for example, by applying a preparation containing this compound, compound Y, compound Z of the present invention, or composition A to the seeds or vegetative reproductive organs using the aforementioned seed treatment method.

[0843] Although the application rate of this compound, compound Y, compound Z 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, the application rate is generally 1000 m³ / h. 2 The dosage is typically 1–500 g. In the case of seed treatment, the amount of this compound, compound Y, compound Z, or composition A is typically 0.001–100 g relative to 1 kg of seeds. When this compound, compound Y, compound Z, or composition A is formulated as an emulsion, wettable powder, aqueous suspension, etc., it is typically diluted with water to a concentration of 0.01–10000 ppm of active ingredient and then applied. Powders and granules are typically applied directly.

[0844] This compound, compound Y, compound Z, or composition A 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.

[0845] Maize (dent, flint, soft, popcorn, glutinous, sweet, non-sweet maize), Rice (long-grain, short-grain, medium-grain, Japanese, 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.

[0846] The above-mentioned plants are any commonly cultivated varieties and are not particularly limited. 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, 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.

[0847] Example

[0848] 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.

[0849] In this specification, Me represents methyl, Et represents ethyl, Pr represents propyl, i-Pr represents isopropyl, c-Pr represents cyclopropyl, Bu represents butyl, i-Bu represents isobutyl, s-Bu represents sec-butyl, c-Pn represents cyclopentyl, Ph represents phenyl, and Bn represents benzyl. When Ph has substituents, the substitution position is stated before the substituent symbol. For example, 4-F-Ph represents 4-fluorophenyl, and 4-MeO-Ph represents 4-methoxyphenyl.

[0850] When determining the physical properties of a compound using liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H]+ or [MH]- and retention time (hereinafter referred to as RT) are recorded. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0851] [LC conditions]

[0852] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Generally Incorporated Chemical Substances Evaluation and Research Organization).

[0853] UV measurement wavelength: 254nm

[0854] Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile

[0855] Flow rate: 2.0 mL / min

[0856] Pumps: 2 units of LC-20AD (manufactured by Shimadzu Corporation) (high pressure gradient)

[0857] Gradient conditions: The solution is delivered using the concentration gradient described in [Table LC1].

[0858] [Table 1]

[0859] [Table LC1]

[0860] Time (minutes) Solution A (%) Solution B (%) 0.01 90 10 2.00 0 100 4.00 0 100 4.01 90 10

[0861] [MS conditions]

[0862] Detector: LCMS-2020 (manufactured by Shimadzu Corporation)

[0863] Ionization method: DUIS

[0864] When the physical properties of a compound are determined using gas chromatography (GC) / mass spectrometry (MS) (hereinafter referred to as GCMS), the measured molecular ion value [M]+ and retention time (hereinafter referred to as RT) are recorded. The conditions for GC and MS are described below.

[0865] [GC Analysis Conditions]

[0866] Equipment: HP 7890A (manufactured by Agilent Technologies)

[0867] Column: HP-5MS (0.25μm × 0.25mm × 30m) (manufactured by Agilent Technologies)

[0868] Inlet temperature: 250℃

[0869] Control mode: Linear velocity, pressure: 14.7 psi, linear velocity: 23.98 cm / sec

[0870] Carrier gas: Helium

[0871] Flow rate: 1 mL / min

[0872] Injection volume: 1.0 μL (split ratio of 200:1)

[0873] Column oven temperature: 70℃ (2 min) → 15℃ / min → 300℃ (2.67 min)

[0874] [MS Analysis Conditions]

[0875] Detector: 5975C Inert XL MSD (Made by Agilent)

[0876] Ionization method: EI

[0877] Ionization voltage: 69.9 eV, ion source temperature: 230℃

[0878] First, an example of manufacturing compound Y (including this compound, the compound of the present invention and compound Z of the present invention) is shown.

[0879] Production Example 1

[0880] 0.22 mL of 1-propanethiol was added to a mixture of 0.50 g of 2-chloro-4-(3-fluoro-4-methylphenyl)pyrimidine, 0.62 g of potassium carbonate, and 5 mL of DMF at 0 °C, and the mixture was stirred at room temperature for 5 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 6:4) to give 0.55 g of compound 1 as shown below.

[0881] [Chemical Formula 42]

[0882]

[0883] Compound 1: 1 H-NMR(CDCl3)δ:8.53(1H,d),7.80-7.72(2H,m),7.33-7.27(2H,m),3.21(2H,t),2.35(3H,d),1.89-1.77(2H,m),1.09(3H,t).

[0884] Manufacturing Example 1-1

[0885] The following shows the compounds manufactured according to Manufacturing Example 1 and their physical properties.

[0886] In the compound represented by formula (IA-1) (hereinafter referred to as compound (IA-1)), n and X 1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compounds are any combination of those listed in [Table A-1].

[0887] [Chemical Formula 43]

[0888]

[0889] [Table 2]

[0890] [Table A-1]

[0891] This compound n <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 2 0 N CH CH CH Et H H H Cl H 3 0 CH N CH CH Pr H H H Me F 67 0 CH N N CH Pr H H H Me F

[0892] Compound 2: 1 H-NMR(CDCl3)δ:8.01-7.95(2H,m),7.53(1H,t),7.46-7.36(3H,m),7.11(1H,dd),3.28(2H,q),1.44(3H,t).

[0893] Compound 3: 1 H-NMR(CDCl3)δ:8.45(1H,dd),7.34(1H,dd),7.31-7.24(3H,m),7.14(1H,dd),3.19(2H,t),2.33(3H,d),1.82-1.71(2H,m),1.06(3H,t).

[0894] Compound 67: 1 H-NMR(CDCl3)δ:8.96(1H,d),7.78-7.68(2H,m),7.52(1H,d),7.32(1H,t),3.06(2H,t),2.35(3H,d),1.88-1.76(2H,m),1.12(3H,t).

[0895] Production Example 2

[0896] A mixture of 0.50 g of 2-bromo-4-(propylthio)pyridine, 0.39 g of 3-fluoro-4-methylphenylboronic acid, 0.15 g of {1,1'-bis(diphenylphosphino)ferrocene}palladium(II) dichloride, 0.91 g of tripotassium phosphate, 9 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 = 10:1) to give 0.53 g of compound 4 as shown below.

[0897] [Chemical Formula 44]

[0898]

[0899] Compound 4: 1H-NMR(CDCl3)δ:8.45(1H,dd),7.66-7.60(2H,m),7.48(1H,dd),7.29-7.24(1 H,m),7.05(1H,dd),3.01(2H,t),2.33(3H,d),1.84-1.72(2H,m),1.09(3H,t).

[0900] Manufacturing Example 2-1

[0901] The following shows the compounds manufactured according to Manufacturing Example 2 and their physical properties.

[0902] In compound (IA-1), n ​​and X 1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compound is any combination of the compounds listed in [Table A-2], [Table A-2A] and [Table A-2B].

[0903] [Table 3]

[0904] [Table A-2]

[0905]

[0906] [Table 4]

[0907] [Table A-2A]

[0908]

[0909] [Table 5]

[0910] [Table A-2B]

[0911]

[0912] Compound 5: 1 H-NMR(CDCl3)δ:8.98(1H,d),7.74-7.69(2H,m),7.51(1H,d),7.30(1H,t),2.62(3H,s),2.34(3H,d).

[0913] Compound 6: 1H-NMR(CDCl3)δ:8.56(2H,t),7.75(1H,t),7.23-7.18(1H,m),6.53-6.47(1H,m),2.99(2H,t),1.77-1.68(2H,m),1.07(3H,t).

[0914] Compound 7: 1 H-NMR(CDCl3)δ:8.59(1H,d),8.52(1H,d),7.77(1H,t),7.33-7.20(3H,m),2.97(2H,t),2.33(3H,d),1.78-1.66(2H,m),1.05(3H,t).

[0915] Compound 8: 1 H-NMR(CDCl3)δ:8.60(1H,s),8.35(1H,s),7.74-7.67(2H,m),7.33-7.27(1H,m),3.25(2H,t),2.35(3H,d),1.86-1.76(2H,m),1.09(3H,t).

[0916] Compound 9: 1 H-NMR(CDCl3)δ:8.80(1H,d),8.58(1H,d),7.36-7.27(3H,m),3.55(2H,q),2.35(3H,d),1.35(3H,t).

[0917] Compound 68: 1 H-NMR(CDCl3)δ:8.96(1H,d),7.76-7.68(2H,m),7.52(1H,d),7.35-7.30(1H,m),3.06(2H,t),2.36(3H,d),1.87-1.78(2H,m),1.12(3H,t).

[0918] Compound 69: LCMS: 300 [M+H] + RT = 1.753 minutes

[0919] Compound 70: LCMS: 296 [M+H] + RT = 1.841 minutes

[0920] Compound 71: LCMS: 296 [M+H] + RT = 1.857 minutes

[0921] Compound 72: LCMS: 316[M+H] + RT = 1.855 minutes

[0922] Compound 73: LCMS: 284 [M+H] + RT = 1.642 minutes

[0923] Compound 74: LCMS: 280 [M+H] + RT = 1.729 minutes

[0924] Compound 75: LCMS: 276 [M+H] + RT = 1.798 minutes

[0925] Compound 76: LCMS: 302[M+H] + RT = 1.712 minutes

[0926] Compound 77: LCMS: 266 [M+H] + RT = 1.584 minutes

[0927] Compound 78: LCMS: 282[M+H] + RT = 1.724 minutes

[0928] Compound 79: LCMS: 262[M+H] + RT = 1.692 minutes

[0929] Compound 80: LCMS: 280 [M+H] + RT = 1.724 minutes

[0930] Compound 81: LCMS: 266 [M+H] + RT = 1.599 minutes

[0931] Compound 82: LCMS: 282[M+H] + RT = 1.716 minutes

[0932] Compound 83: LCMS: 278 [M+H] + RT = 1.569 minutes

[0933] Compound 84: LCMS: 293 [M+H] + RT = 1.547 minutes

[0934] Compound 85: LCMS: 262 [M+H] + RT = 1.600 minutes

[0935] Compound 86: LCMS: 287 [M+H] + RT = 1.846 minutes

[0936] Compound 87: LCMS: 288 [M+H] + RT = 1.860 minutes

[0937] Compound 88: LCMS: 262 [M+H] + RT = 1.695 minutes

[0938] Compound 89: LCMS: 344 [M+H] + RT = 1.778 minutes

[0939] Compound 90: LCMS: 282 [M+H] + RT = 1.666 minutes

[0940] Compound 91: LCMS: 294 [M+H] + RT = 1.859 minutes

[0941] Compound 92: LCMS: 291 [M+H] + RT = 1.568 minutes

[0942] Compound 93: LCMS: 316 [M+H] + RT = 1.891 minutes

[0943] Compound 94: LCMS: 276 [M+H] + RT = 1.815 minutes

[0944] Compound 95: LCMS: 273 [M+H] + RT = 1.466 minutes

[0945] Compound 96: LCMS: 298 [M+H] + RT = 1.791 minutes

[0946] Compound 97: LCMS: 278 [M+H] + RT = 1.593 minutes

[0947] Compound 98: LCMS: 291 [M+H] + RT = 1.451 minutes

[0948] Compound 99: LCMS: 294 [M+H] + RT = 1.711 minutes

[0949] This compound 100: 1H-NMR(CDCl3)δ:9.08(1H,d),9.04(1H,d),8.34(1H,t),7.55-7.52(2H,m),7.3 5-7.32(2H,m),3.18-3.13(2H,m),2.44(3H,s),1.86-1.77(2H,m),1.04(3H,t).

[0950] This compound 101: 1 H-NMR(CDCl3)δ:9.07-9.04(2H,m),8.31(1H,t),7.47-7.39(2H,m),7.16 (1H,t),3.18-3.14(2H,m),2.38(3H,d),1.87-1.77(2H,m),1.05(3H,t).

[0951] This compound 102: 1 H-NMR(CDCl3)δ:9.12(1H,d),9.03(1H,d),8.28(1H,t),7.29-7.25(2H,m),3.19-3.15(2H,m),1.88-1.77(2H,m),1.06(3H,t).

[0952] This compound 103: 1 H-NMR(CDCl3)δ:9.11(1H,d),9.06(1H,d),8.32(1H,t),7.60-7.55(1H,m),7.43 (1H,dd),7.39-7.35(1H,m),3.19-3.15(2H,m),1.88-1.77(2H,m),1.06(3H,t).

[0953] This compound 104: 1 H-NMR(CDCl3)δ:9.01(1H,d),8.96(1H,d),8.19(1H,t),7.37-7.27(3H,m),2.81(6H,s),2.36(3H,d).

[0954] Compound 105: 1 H-NMR(CDCl3)δ:9.01(1H,d),8.97(1H,d),8.15(1H,t),7.28-7.23(2H,m),2.82(6H,s).

[0955] This compound 106: 1H-NMR(CDCl3)δ:8.99(1H,d),8.96(1H,d),8.20(1H,t),7.36-7.25(3H,m),3.20(2H,q),2.83(3H,s),2.35(3H,d),1.19(3H,t).

[0956] Compound 107: 1 H-NMR(CDCl3)δ:9.01(1H,d),8.94(1H,d),8.16(1H,t),7.26-7.22(2H,m),3.21(2H,q),2.84(3H,s),1.20(3H,t).

[0957] This compound 108: 1 H-NMR(CDCl3)δ:9.16(1H,d),9.07(1H,d),8.41(1H,t),7.80-7.72(3H,m),7.52(1H,dd),6.85(1H,dd),3.23(2H,q),1.38(3H,t).

[0958] This compound 109: 1 H-NMR(CDCl3)δ:9.30(1H,s),9.26(1H,s),8.34-8.29(2H,m),7.43(1H,t),3.46-3.42(2H,m),1.94-1.84(2H,m),1.09(3H,t).

[0959] This compound 110: 1 H-NMR(CDCl3)δ:9.24(1H,s),9.21(1H,s),7.86-7.83(2H,m),7.26-7.23(1H,m),3.45-3.41(2H,m),1.93-1.83(2H,m),1.08(3H,t).

[0960] This compound 111: 1 H-NMR(CDCl3)δ:9.26(1H,s),9.21(1H,s),7.78-7.75(2H,m),3.45-3.41(2H,m),1.91-1.84(2H,m),1.09(3H,t).

[0961] Compound 112: 1H-NMR(CDCl3)δ:9.32(1H,s),9.25(1H,s),8.19(2H,d),7.71(2H,d),6.74(1H,t),3.47-3.43(2H,m),1.93-1.84(2H,m),1.08(3H,t).

[0962] This compound 113: 1 H-NMR(CDCl3)δ:9.28(1H,s),9.25(1H,s),7.78-7.73(2H,m),3.46-3.42(2H,m),1.93-1.84(2H,m),1.09(3H,t).

[0963] Compound 114: LCMS: 303 [M+H] + RT = 1.942 minutes

[0964] Compound 115: LCMS: 355 [M+H] + RT = 2.044 minutes

[0965] Compound 116: LCMS: 320 [M+H] + RT = 1.578 minutes

[0966] Compound 117: LCMS: 277 [M+H] + RT = 1.841 minutes

[0967] This compound 118: 1 H-NMR(CDCl3)δ:9.09(1H,d),9.05(1H,d),8.31(1H,t),7.19-7.10(2H,m),3.19-3.15(2H,m),2.27(3H,d),1.89-1.77(2H,m),1.06(3H,t).

[0968] This compound 119: 1 H-NMR(CDCl3)δ:9.24-9.21(2H,m),7.64-7.57(2H,m),3.47-3.42(2H,m),2.29(3H,t),1.93-1.83(2H,m),1.09(3H,t).

[0969] This compound 120: 1H-NMR(CDCl3)δ:8.61(1H,d),8.50(1H,d),7.62(1H,t),7.28-7.24(1H,m),7 .22-7.08(4H,m),6.86-6.80(2H,m),4.10(2H,s),3.79(3H,s),2.32(3H,d).

[0970] This compound 160: 1 H-NMR(CDCl3)δ:9.10(1H,d),9.05(1H,d),8.30(1H,t),7.48-7.43(1H,m ),7.38-7.31(2H,m),3.19-3.15(2H,m),1.89-1.76(2H,m),1.06(3H,t).

[0971] Compound 161: 1 H-NMR(CDCl3)δ:9.08(1H,d),9.03(1H,d),8.34(1H,t),7.43-7.35(2H,m),7.31-7.27 (1H,m),3.21-3.12(2H,m),2.36(3H,s),2.34(3H,s),1.88-1.76(2H,m),1.04(3H,t).

[0972] Compound 162: 1 H-NMR(CDCl3)δ:9.09-9.06(2H,m),8.32(1H,t),7.62(1H,d),7.45-7.37 (2H,m),3.20-3.12(2H,m),2.46(3H,s),1.88-1.76(2H,m),1.05(3H,t).

[0973] This compound 169: 1 H-NMR(CDCl3)δ:9.13(1H,d),9.07(1H,d),8.32(1H,t),7.20-7.13(2H,m ),6.98-6.91(1H,m),3.20-3.14(2H,m),1.89-1.77(2H,m),1.06(3H,t).

[0974] This compound 170: 1H-NMR(CDCl3)δ:9.09(1H,d),9.04(1H,d),8.34(1H,t),7.56-7.51(2H,m),7.36-7.31(2 H,m),3.22-3.12(2H,m),2.44(3H,s),1.80-1.72(2H,m),1.49-1.38(2H,m),0.92(3H,t).

[0975] Compound 171: 1 H-NMR(CDCl3)δ:9.10(1H,d),9.05(1H,d),8.30(1H,t),7.50-7.42(1H,m),7.40-7 .30(2H,m),3.22-3.13(2H,m),1.82-1.71(2H,m),1.51-1.38(2H,m),0.93(3H,t).

[0976] Compound 172: 1 H-NMR(CDCl3)δ:9.07(2H,d),8.32(1H,t),7.38-7.27(3H,m),3.21-3.12 (2H,m),2.36(3H,d),1.82-1.70(2H,m),1.50-1.38(2H,m),0.93(3H,t).

[0977] Compound 173: 1 H-NMR(CDCl3)δ:9.07(2H,t),8.32(1H,t),7.62(1H,d),7.45-7.37(2H,m),3.22-3.15(2H,m),2.45(3H,s),1.82-1.71(2H,m),1.50-1.38

[0978] (2H,m),0.93(3H,t).

[0979] Compound 174: 1 H-NMR(CDCl3)δ:9.07(1H,d),9.03(1H,d),8.34(1H,t),7.56-7.51(2H,m),7.36-7.31(2H,m),3.62-3 .50(1H,m),2.44(3H,s),2.18-2.07(2H,m),2.00-1.88(2H,m),1.88-1.76(2H,m),1.70-1.61(2H,m).

[0980] Compound 175: 1H-NMR(CDCl3)δ:9.09(1H,d),9.03(1H,d),8.30(1H,t),7.49-7.42(1H,m),7.39-7.3 0(2H,m),3.62-3.49(1H,m),2.21-2.06(2H,m),2.00-1.76(4H,m),1.74-1.61(2H,m).

[0981] Compound 176: 1 H-NMR(CDCl3)δ:9.06(1H,d),9.05(1H,d),8.32(1H,t),7.37-7.27(3H,m),3.61-3.50(1H,m ),2.36(3H,d),2.18-2.07(2H,m),2.01-1.89(2H,m),1.88-1.77(2H,m),1.72-1.61(2H,m).

[0982] Compound 177: 1 H-NMR(CDCl3)δ:9.06(1H,d),9.05(1H,d),8.32(1H,t),7.62(1H,d),7.45-7.37(2H,m),3.63-3.4 9(1H,m),2.45(3H,s),2.19-2.05(2H,m),2.00-1.89(2H,m),1.87-1.78(2H,m),1.73-1.61(2H,m).

[0983] This compound 178: 1 H-NMR(CDCl3)δ:9.11(1H,d),8.99(1H,d),8.39(1H,t),7.79(1H,dd),7.72 (1H,dd),7.52-7.47(2H,m),7.35-7.30(2H,m),7.14(1H,dd),2.43(3H,s).

[0984] This compound 179: 1 H-NMR(CDCl3)δ:9.12(1H,d),8.96(1H,d),8.36(1H,t),7.79(1H,dd),7.73(1H,dd),7.44-7.35(2H,m),7.18-7.11(2H,m),2.37(3H,d).

[0985] This compound 180: 1H-NMR(CDCl3)δ:9.16(1H,d),8.95(1H,d),8.35(1H,t),7.80(1H,dd),7.74(1H,dd),7.45-7.39(1H,m),7.36-7.30(2H,m),7.16(1H,dd).

[0986] Compound 181: 1 H-NMR(CDCl3)δ:9.15(1H,s),8.63(1H,s),7.55(1H,t),7.13(1H,dd),7.07- 7.02(1H,m),3.23-3.15(2H,m),2.59(3H,s),1.92-1.79(2H,m),1.07(3H,t).

[0987] Compound 182: 1 H-NMR(CDCl3)δ:9.11(1H,s),8.64(1H,s),7.33-7.28(2H,m),7.21-7.15(2H,m ),3.23-3.14(2H,m),2.59(3H,s),2.44(3H,s),1.90-1.78(2H,m),1.07(3H,t).

[0988] Compound 183: LCMS: 296 [M+H] + RT = 1.844 minutes

[0989] Compound 184: LCMS: 280 [M+H] + RT = 1.723 minutes

[0990] Compound 185: LCMS: 336 [M+H] + RT = 1.966 minutes

[0991] Compound 186: LCMS: 320 [M+H] + RT = 1.850 minutes

[0992] This compound 187: 1 H-NMR(CDCl3)δ:9.09(1H,d),9.08(1H,d),8.34(1H,t),7.70-7.64(2H,m),7.54-7.46(2H,m),3.22(2H,q),1.36(3H,t).

[0993] Compound 188: LCMS: 332 [M+H] + RT = 1.915 minutes

[0994] This compound 189: 1 H-NMR(CDCl3)δ:9.11(1H,d),8.94(1H,d),8.33(1H,t),8.04-7.99(2H,m),7.70-7.53(3H,m),7.46-7.38(1H,m),7.35-7.30(2H,m).

[0995] This compound 190: 1 H-NMR(CDCl3)δ:9.13(1H,d),8.92(1H,d),8.30(1H,t),8.04-7.98(2H,m),7.69-7.55(3H,m),7.25-7.19(2H,m).

[0996] This compound 191: 1 H-NMR(CDCl3)δ:9.12(1H,d),8.95(1H,d),8.34(1H,t),8.04-7.99(2H,m),7.67-7.62(1H,m),7.61-7.53(3H,m),7.41-7.30(2H,m).

[0997] Compound 192: LCMS: 330 [M+H] + RT = 1.992 minutes

[0998] Compound 193: LCMS: 314 [M+H] + RT = 1.863 minutes

[0999] Compound 194: LCMS: 310 [M+H] + RT = 1.965 minutes

[1000] Compound 195: LCMS: 330 [M+H] + RT = 1.980 minutes

[1001] Compound 196: LCMS: 314 [M+H] + RT = 1.872 minutes

[1002] Compound 197: LCMS: 348 [M+H] + RT = 1.987 minutes

[1003] Compound 198: LCMS: 314 [M+H] + RT = 1.857 minutes

[1004] Manufacturing Example 3

[1005] At 0°C, 0.53 g of mCPBA (75% purity, containing 25% water) was added to a mixture of 0.41 g of compound 4 and 6 mL of chloroform, and the mixture was stirred at room temperature for 1 hour. 10 mL of saturated sodium thiosulfate aqueous solution and 10 mL of saturated sodium bicarbonate aqueous solution were added to the resulting mixture, and after stirring for 1 hour, extraction was performed using chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.18 g of compound 10 and 0.22 g of compound 11.

[1006] [Chemical Formula 45]

[1007]

[1008] Compound 10: 1 H-NMR(CDCl3)δ:8.93(1H,dd),8.13(1H,dd),7.80-7.72(2H,m),7.67(1H,dd) ,7.32(1H,t),3.16-3.11(2H,m),2.35(3H,d),1.86-1.75(2H,m),1.04(3H,t).

[1009] [Chemical Formula 46]

[1010]

[1011] Compound 11: 1 H-NMR(CDCl3)δ:8.79(1H,d),7.98-7.95(1H,m),7.79-7.72(2H,m),7.38(1H,dd),7.30(1 H,t),2.89-2.83(2H,m),2.34(3H,d),1.98-1.86(1H,m),1.77-1.66(1H,m),1.09(3H,t).

[1012] Manufacturing Example 3-1

[1013] The following shows the compound manufactured according to manufacturing example 3 and its physical properties.

[1014] In compound (IA-1), n ​​and X 1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4CThe compounds are any combination of those listed in [Table A-3].

[1015] [Table 6]

[1016] [Table A-3]

[1017] This compound n <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 12 2 N CH CH CH Et H H H H Cl 13 1 N CH CH CH Et H H H H Cl 14 2 CH CH N CH Pr H H H Me F 15 1 CH CH N CH Pr H H H Me F 16 2 CH N CH CH Pr H H H Me F 17 1 CH N CH CH Pr H H H Me F 18 2 CH N CH N Me H H H Me F 19 1 CH N CH N Me H H H Me F 20 2 CH CH N CH Pr H H F Cl F 21 1 CH CH N CH Pr H H F Cl F 22 2 N CH N CH Pr H H H Me F 23 1 N CH N CH Pr H H H Me F 121 2 CH CH N CH 4-Pyridyl H H H Me F 122 1 CH CH N CH 4-Pyridyl H H H Me F 123 2 CH CH N CH 3-F-Ph H H H Me F 124 1 CH CH N CH 3-F-Ph H H H Me F 125 2 CH CH N CH 2-Furanyl H H H Me F 126* 2 CH CH N CH 2-Furanyl H H H Me F 127 2 CH CH N CH 3-Furanyl H H H Me F 128 1 CH CH N CH 3-Furanyl H H H Me F 129 2 CH CH N CH 2-Thienyl H H H Me F 130 1 CH CH N CH 2-Thienyl H H H Me F 131 2 CH CH N CH 3-Thienyl H H H Me F 132 1 CH CH N CH 3-Thienyl H H H Me F 133 2 CH CH N CH 2-Pyridyl H H H Me F 134 2 CH CH N CH i-Pr H H H Me F 135 2 CH CH N CH 2-Pyrazinyl H H H Me F 136 2 N CH CH CH Et H H H Me F 137 1 N CH CH CH Et H H H Me F 138 2 N CH CH CH Et H H H H <![CDATA[C(O)NMe2]]> 139 1 N CH CH CH Et H H H H <![CDATA[C(O)NMe2]]> 140 2 CH N N CH Pr H H H Me F 141 1 CH N N CH Pr H H H Me F 142 2 CH CH N N Pr H H H Me F 143 1 CH CH N N Pr H H H Me F 144 2 N N CH CH Pr H H H Me F

[1018] [Table 7]

[1019] [Table A-3] (continued)

[1020] 145 1 N N CH CH Pr H H H Me F 158 2 CH CH N CH Ph H H H Me F 159* 2 CH CH N CH Ph H H H Me F 163 2 CH CH N CH 7-quinolinyl H H H Me F 164 2 CH CH N CH 3-Furanyl H H H Me H 165 2 CH CH N CH 3-Thienyl H H H Me H 166 2 CH CH N CH 3-Furanyl H H H Cl H 167 2 CH CH N CH 3-Thienyl H H H Cl H

[1021] Here, the asterisk (*) in the compound designation of the compounds listed in [Table A-3] above refers to N-oxides. Specifically, these are compounds with the following structures.

[1022] This compound 126

[1023] [Chemical Formula 47]

[1024]

[1025] This compound 159

[1026] [Chemical Formula 48]

[1027]

[1028] Compound 12: 1 H-NMR(CDCl3)δ:8.06-7.91(5H,m),7.52-7.46(2H,m),3.52(2H,q),1.36(3H,t).

[1029] Compound 13: 1 H-NMR(CDCl3)δ:8.03-7.92(4H,m),7.78(1H,d),7.49-7.43(2H,m),3.31-3.18(1H,m),3.05-2.96(1H,m),1.29-1.23(3H,m).

[1030] Compound 14: 1 H-NMR(CDCl3)δ:9.07(2H,d),8.32(1H,t),7.37-7.27(3H,m),3.19-3.12(2H,m),2.36(3H,d),1.89-1.76(2H,m),1.05(3H,t).

[1031] Compound 15: 1H-NMR(CDCl3)δ:8.93(1H,s),8.69(1H,s),8.22(1H,t),7.35-7.29(3H,m),2.9 6-2.84(2H,m),2.35(3H,d),1.95-1.82(1H,m),1.79-1.69(1H,m),1.10(3H,t).

[1032] Compound 16: 1 H-NMR(CDCl3)δ:8.77(1H,dd),8.28(1H,dd),7.71(1H,dd),7.42-7.32(3H,m),3.46-3.39(2H,m),2.36(3H,d),1.87-1.77(2H,m),1.05(3H,t).

[1033] Compound 17: 1 H-NMR(CDCl3)δ:8.65(1H,d),8.19(1H,t),7.55-7.52(1H,m),7.47-7.37(2H,m),7.35-7.29(1H,m),3 .18-3.07(1H,m),2.98-2.87(1H,m),2.35(3H,s),2.03-1.88(1H,m),1.73-1.62(1H,m),1.08(3H,t).

[1034] Compound 18: 1 H-NMR(CDCl3)δ:9.36(1H,d),8.34(1H,d),7.93-7.82(2H,m),7.37(1H,t),3.31(3H,s),2.38(3H,d).

[1035] Compound 19: 1 H-NMR(CDCl3)δ:9.21(1H,s),8.40(1H,s),7.95-7.87(2H,m),7.35(1H,t),2.95(3H,s),2.37(3H,d).

[1036] Compound 20: 1 H-NMR(CDCl3)δ:9.13(1H,d),9.06(1H,d),8.34(1H,t),7.33-7.25(2H,m),3.22-3.15(2H,m),1.88-1.78(2H,m),1.06(3H,t).

[1037] Compound 21: 1H-NMR(CDCl3)δ:8.91(1H,d),8.74(1H,d),8.25(1H,t),7.33-7.27(2H,m ),2.97-2.81(2H,m),1.97-1.84(1H,m),1.80-1.67(1H,m),1.11(3H,t).

[1038] Compound 22: 1 H-NMR(CDCl3)δ:9.24(1H,s),9.19(1H,s),7.81-7.74(2H,m),7.41-7.34 (1H,m),3.48-3.41(2H,m),2.38(3H,d),1.94-1.82(2H,m),1.08(3H,t).

[1039] Compound 23: 1 H-NMR(CDCl3)δ:9.10(1H,s),9.09(1H,s),7.75-7.69(2H,m),7.35(1H,t),3.24-3.12(1 H,m),3.08-2.98(1H,m),2.37(3H,d),2.07-1.95(1H,m),1.79-1.66(1H,m),1.10(3H,t).

[1040] This compound 121: 1 H-NMR(CDCl3)δ:9.12(1H,d),9.03(1H,d),8.90(2H,dd),8.35(1H,t),7.84(2H,dd),7.38-7.22(3H,m),2.35(3H,d).

[1041] This compound 122: 1 H-NMR(CDCl3)δ:8.94-8.89(1H,m),8.84-8.81(1H,m),8.80-8.75(2H,m),8.17-8.13(1H,m),7.63-7.60(2H,m),7.37-7.20(3H,m),2.33(3H,s).

[1042] This compound 123: 1 H-NMR(CDCl3)δ:9.09(1H,d),8.99(1H,d),8.33(1H,t),7.83-7.79(1H,m ),7.73-7.69(1H,m),7.59-7.53(1H,m),7.36-7.22(4H,m),2.35(3H,d).

[1043] This compound 124:1 H-NMR(CDCl3)δ:8.88(1H,d),8.74(1H,d),8.16(1H,t),7.51-7.45(3H,m),7.33-7.17(4H,m),2.33(3H,d).

[1044] Compound 125: 1 H-NMR(CDCl3)δ:9.14(1H,d),9.02(1H,d),8.40(1H,t),7.61(1H,dd),7.38-7.24(4H,m),6.56(1H,dd),2.35(3H,d).

[1045] Compound 126: 1 H-NMR(CDCl3)δ:8.66(1H,t),8.50(1H,t),7.91(1H,t),7.67(1H,dd),7.38-7.32(2H,m),7.26-7.20(2H,m),6.61(1H,dd),2.35(3H,d).

[1046] Compound 127: 1 H-NMR(CDCl3)δ:9.11(1H,d),9.01(1H,d),8.35(1H,t),8.12(1H,dd),7.51(1H,t),7.36-7.23(3H,m),6.68(1H,dd),2.35(3H,d).

[1047] Compound 128: 1 H-NMR(CDCl3)δ:8.92(1H,d),8.68(1H,d),8.23(1H,t),7.96(1H,t),7.51(1H,t),7.36-7.27(3H,m),6.45(1H,dd),2.34(3H,d).

[1048] This compound 129: 1 H-NMR(CDCl3)δ:9.13(1H,d),8.98(1H,d),8.37(1H,t),7.80(1H,dd),7.73(1H,dd),7.35-7.24(3H,m),7.15(1H,dd),2.34(3H,d).

[1049] This compound 130: 1H-NMR(CDCl3)δ:8.91(1H,d),8.70(1H,d),8.28(1H,t),7.69-7.67(2H,m),7.34-7.27(3H,m),7.15-7.12(1H,m),2.34(3H,d).

[1050] This compound 131: 1 H-NMR(CDCl3)δ:9.10(1H,d),8.98(1H,d),8.35(1H,t),8.21(1H,dd),7.46(1H,dd),7.40(1H,dd),7.35-7.23(3H,m),2.35(3H,d).

[1051] Compound 132: 1 H-NMR(CDCl3)δ:8.89(1H,d),8.68(1H,d),8.21(1H,t),7.92(1H,dd),7.47(1H,dd),7.34-7.25(3H,m),7.15(1H,dd),2.34(3H,d).

[1052] This compound 133: 1 H-NMR(CDCl3)δ:9.19(1H,d),9.02(1H,d),8.71-8.69(1H,m),8.52(1H,t),8.28 -8.25(1H,m),7.99(1H,td),7.54-7.50(1H,m),7.36-7.28(3H,m),2.34(3H,d).

[1053] Compound 134: 1 H-NMR(CDCl3)δ:9.07(1H,d),9.04(1H,d),8.30(1H,t),7.38-7.27(3H,m),3.33-3.23(1H,m),2.36(3H,d),1.37(6H,d).

[1054] Compound 135: 1 H-NMR(CDCl3)δ:9.45(1H,d),9.21(1H,d),9.05(1H,d),8.83(1H,d),8.67(1H,dd),8.50(1H,t),7.38-7.27(3H,m),2.35(3H,d).

[1055] Compound 136: 1H-NMR(CDCl3)δ:8.05-7.98(2H,m),7.96-7.91(1H,m),7.78-7.68(2H,m),7.31(1H,t),3.53(2H,q),2.35(3H,d),1.37(3H,t).

[1056] Compound 137: 1 H-NMR(CDCl3)δ:8.00-7.91(2H,m),7.79-7.64(3H,m),7.29(1H,t),3.28-3.21(1H,m),3.05-2.98(1H,m),2.34(3H,d),1.25(3H,t).

[1057] This compound 138: 1 H-NMR(CDCl3)δ:8.15-7.97(5H,m),7.59-7.49(2H,m),3.52(2H,q),3.16(3H,s),3.02(3H,s),1.35(3H,t).

[1058] This compound 139: 1 H-NMR(CDCl3)δ:8.12-7.93(4H,m),7.85-7.79(1H,m),7.56-7.47(2H,m),3.31-3.20(1H,m),3.16(3H,s),3.07-2.96(4H,m),1.25(3H,t).

[1059] Compound 140: 1 H-NMR(CDCl3)δ:9.52(1H,d),8.22(1H,d),7.91(1H,d),7.83(1H,d),7.4 0(1H,t),3.22-3.18(2H,m),2.39(3H,s),1.89-1.79(2H,m),1.08(3H,t).

[1060] Compound 141: 1 H-NMR(CDCl3)δ:9.17(1H,d),8.21(1H,d),7.92(1H,dd),7.84(1H,dd),7.37(1H,t) ,3.02-2.85(2H,m),2.38(3H,d),2.04-1.89(1H,m),1.80-1.66(1H,m),1.12(3H,t).

[1061] Compound 142: LCMS: 295 [M+H] + RT = 1.804 minutes

[1062] Compound 143: 1 H-NMR(CDCl3)δ:9.19(1H,d),8.21-8.20(1H,m),7.93-7.82(2H,m),7.37(1H,t),3.0 3-2.87(2H,m),2.37(3H,s),2.03-1.88(1H,m),1.80-1.64(1H,m),1.15-1.08(3H,m).

[1063] Compound 144: 1 H-NMR(CDCl3)δ:8.93(1H,d),7.88-7.82(3H,m),7.36(1H,t),3.61-3.56(2H,m),2.38(3H,d),2.02-1.92(2H,m),1.12(3H,t).

[1064] Compound 145: 1 H-NMR(CDCl3)δ:8.90(1H,d),7.88-7.81(2H,m),7.71(1H,d),7.35(1H,t),3.2 2-3.08(2H,m),2.37(3H,d),2.10-1.96(1H,m),1.83-1.68(1H,m),1.10(3H,t).

[1065] This compound 158: 1 H-NMR(CDCl3)δ:9.08(1H,d),8.96(1H,d),8.34(1H,t),8.03-8.00(2H,m),7.66-7 .61(1H,m),7.59-7.52(2H,m),7.34-7.28(2H,m),7.24-7.22(1H,m),2.34(3H,d).

[1066] Compound 159: 1 H-NMR(CDCl3)δ:8.59(1H,t),8.45(1H,t),8.01-8.00(1H,m),7.99-7.98(1H,m),7.85(1H,t ),7.71-7.67(1H,m),7.62-7.58(2H,m),7.38-7.30(1H,m),7.24-7.18(2H,m),2.35(3H,d).

[1067] Compound 163: 1H-NMR(CDCl3)δ:9.17(1H,d),9.06(1H,dd),8.97(1H,d),8.83(1H,t),8.41(1H,t), 8.26-8.22(1H,m),8.07-7.98(2H,m),7.58(1H,dd),7.34-7.22(3H,m),2.34(3H,d).

[1068] Compound 164: 1 H-NMR(CDCl3)δ:9.08(1H,d),9.02(1H,d),8.36(1H,t),8.11(1H,dd),7.52-7.49(3H,m),7.33(2H,d),6.67(1H,dd),2.43(3H,s).

[1069] Compound 165: 1 H-NMR(CDCl3)δ:9.08(1H,d),9.00(1H,d),8.37(1H,t),8.20(1H,dd),7.53-7.4 8(2H,m),7.46-7.43(1H,m),7.41-7.38(1H,m),7.35-7.31(2H,m),2.43(3H,s).

[1070] Compound 166: 1 H-NMR(CDCl3)δ:9.12(1H,d),9.01(1H,d),8.36(1H,t),8.12(1H,dd),7.57-7.48(5H,m),6.68(1H,dd).

[1071] Compound 167: 1 H-NMR(CDCl3)δ:9.12(1H,d),8.99(1H,d),8.37(1H,t),8.21(1H,dd),7.56-7.45(5H,m),7.41(1H,dd).

[1072] Production Example 4

[1073] A mixture of 0.21 g of 2-chloro-4-(ethylsulfonyl)pyrimidine, 0.17 g of 4-chlorophenylboronic acid, 0.07 g of {1,1'-bis(diphenylphosphino)ferrocene}palladium(II) dichloride, 0.64 g of tripotassium phosphate, and 4 mL of DME was stirred under reflux for 5 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 4:1) to give 0.01 g of compound 24 as shown below.

[1074] [Chemical Formula 49]

[1075]

[1076] Compound 24: 1 H-NMR(CDCl3)δ:9.14(1H,d),8.44(2H,dt),7.89(1H,d),7.50(2H,dt),3.55(2H,q),1.41(3H,t).

[1077] Production Example 5

[1078] A mixture of 0.40 g of intermediate 14, 0.24 mL of 3-bromofluorobenzene, 0.02 g of palladium acetate, 0.11 g of Xantphos, 0.35 g of sodium tert-butoxide, and 5 mL of toluene was stirred under reflux for 7 hours. Ethyl acetate was added to the resulting mixture, and the mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 2:1) to give 0.53 g of compound 146 as shown below.

[1079] [Chemical Formula 50]

[1080]

[1081] Compound 146: 1 H-NMR(CDCl3)δ:8.72(1H,d),8.56(1H,d),7.83(1H,t),7.35-7.26(2H,m),7.24-7 .17(2H,m),7.16-7.12(1H,m),7.07-7.02(1H,m),7.01-6.95(1H,m),2.32(3H,d).

[1082] Manufacturing Example 5-1

[1083] The following shows the compounds manufactured according to Manufacturing Example 5 and their physical properties.

[1084] In compound (IA-1), n ​​and X 1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compounds are any combination of those listed in [Table A-9].

[1085] [Table 8]

[1086] [Table A-9]

[1087] This compound m <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 147 0 CH CH N CH 7-Quinolinyl H H H Me F 148 0 CH CH N CH 4-Pyridyl H H H Me F 149 0 CH CH N CH 2-Furanyl H H H Me F 150 0 CH CH N CH 2-Thienyl H H H Me F 151 0 CH CH N CH 3-Furanyl H H H Me F 152 0 CH CH N CH 3-Thienyl H H H Me F 153 0 CH CH N CH 3-Pyridyl H H H Me F 168 0 CH CH N CH 3-Thienyl H H H Me H

[1088] Compound 147: LCMS: 347 [M+H] + RT = 1.954 minutes

[1089] Compound 148: 1 H-NMR(CDCl3)δ:8.88(1H,d),8.71(1H,d),8.42(2H,dd),8.02(1H,t),7.34-7.22(3H,m),7.02(2H,dd),2.34(3H,d).

[1090] This compound 149: 1 H-NMR(CDCl3)δ:8.60(1H,d),8.39(1H,d),7.63-7.59(2H,m),7.29-7.23(1H,m),7.22-7.13(2H,m),6.82(1H,dd),6.50(1H,dd),2.31(3H,d).

[1091] This compound 150: 1 H-NMR(CDCl3)δ:8.57(1H,d),8.40(1H,d),7.59(1H,t),7.52(1H,d),7.37-7.34(1H,m),7.30-7.08(4H,m),2.31(3H,d).

[1092] Compound 151: 1 H-NMR(CDCl3)δ:8.57(1H,d),8.41(1H,d),7.69-7.68(1H,m),7.61(1H,t),7.56 -7.54(1H,m),7.30-7.23(1H,m),7.21-7.13(2H,m),6.48(1H,dd),2.32(3H,d).

[1093] Compound 152: 1 H-NMR(CDCl3)δ:8.58(1H,d),8.40(1H,d),7.61(1H,t),7.50(1H,dd),7.43 (1H,dd),7.29-7.23(1H,m),7.20-7.13(2H,m),7.09(1H,dd),2.31(3H,d).

[1094] Compound 153: 1H-NMR(CDCl3)δ:8.70(1H,d),8.66(1H,d),8.56-8.53(2H,m),7.79(1H,t ),7.72-7.68(1H,m),7.30-7.26(2H,m),7.22-7.16(2H,m),2.32(3H,d).

[1095] This compound 168: 1 H-NMR(CDCl3)δ:8.61(1H,d),8.39(1H,d),7.64(1H,t),7.48(1H,dd),7.44-7.38(3H,m),7.29-7.24(2H,m),7.09(1H,dd),2.40(3H,s).

[1096] Production Example 6

[1097] 0.49 g of N-chlorosuccinimide was added to a mixture of 0.20 g of intermediate 14, 0.14 mL of 2-propanol, and 3 mL of chloroform at 0 °C, and the mixture was stirred at room temperature for 4 hours. An aqueous solution of sodium sulfite and a saturated aqueous solution of sodium bicarbonate were added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was dried with sodium sulfate and concentrated under reduced pressure.

[1098] At 0°C, 0.11 mL of pyrrolidine was added to a mixture of the obtained residue, 5 mL of chloroform, and 0.19 mL of triethylamine, and the mixture was stirred at room temperature for 2 hours. An aqueous solution of sodium sulfite was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.23 g of compound 154 as shown below.

[1099] [Chemical Formula 51]

[1100]

[1101] Compound 154: 1 H-NMR(CDCl3)δ:9.02-8.99(2H,m),8.25(1H,t),7.37-7.26(3H,m),3.37-3.29(4H,m),2.35(3H,d),1.87-1.80(4H,m).

[1102] Manufacturing Example 6-1

[1103] The following shows the compounds manufactured according to Manufacturing Example 6 and their physical properties.

[1104] In compound (IA-1), n ​​and X1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compounds are those of the combinations listed in [Table A-10].

[1105] [Table 9]

[1106] [Table A-10]

[1107] This compound n <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 199 2 CH CH N CH NHMe H H H Cl H

[1108] This compound 199: 1 H-NMR(CDCl3)δ:9.05(1H,d),9.01(1H,d),8.29(1H,t),7.60-7.48(4H,m),4.56(1H,d),2.78(3H,d).

[1109] Production Example 7

[1110] A mixture of 0.10 g of intermediate 14, 0.05 mL of 2-chloropyrazine, 0.22 g of cesium carbonate, and 2 mL of NMP was stirred at 80 °C for 2 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was dried over sodium sulfate, concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.12 g of compound 155 as shown below.

[1111] [Chemical Formula 52]

[1112]

[1113] Compound 155: 1 H-NMR(CDCl3)δ:8.85(1H,d),8.74(1H,d),8.44(1H,d),8.35(1H,dd),8.32(1H,d),8.08(1H,t),7.33-7.22(3H,m),2.34(3H,d).

[1114] Manufacturing Example 7-1

[1115] The following shows the compounds manufactured according to Manufacturing Example 7 and their physical properties.

[1116] In compound (IA-1), n ​​and X 1 X 2 X 3X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compounds are any combination of those listed in [Table A-8].

[1117] [Table 10]

[1118] [Table A-8]

[1119] This compound n <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 156 0 CH CH N CH 2-Pyridyl H H H Me F 157 0 CH CH N CH i-Pr H H H Me F

[1120] Compound 156: 1 H-NMR(CDCl3)δ:8.81(1H,d),8.72(1H,d),8.46-8.41(1H,m),8.06(1H,t),7.54(1H,td),7.33-7.21(3H,m),7.13-7.05(2H,m),2.33(3H,d).

[1121] Compound 157: 1 H-NMR(CDCl3)δ:8.66(1H,d),8.59(1H,d),7.86(1H,t),7.32-7.21(3H,m),3.49-3.39(1H,m),2.33(3H,d),1.34(6H,d).

[1122] Production Example 8

[1123] Under a nitrogen atmosphere, at 0°C, 2.4 mL of a solution of isopropyl magnesium chloride and lithium chloride complex (1.3 M, THF solution) was added to a mixture of 0.5 g of 5-bromo-1,3-difluoro-2-methylbenzene and 5.5 mL of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours. At room temperature, 4 mL of the resulting mixture was added dropwise to a mixture of 0.3 g of intermediate 12, 27 mg of nickel(II) chloride, 96 mg of zinc(II) chloride, and 3 mL of THF, and the mixture was stirred at 60°C for 4.5 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 concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give compound 96 as shown in the following formula.

[1124] [Chemical Formula 53]

[1125]

[1126] Compound 96: LCMS: 298 [M+H] + RT = 1.791 minutes

[1127] The following shows the compounds and their physical properties manufactured according to the above manufacturing method and manufacturing examples.

[1128] In compound (IA-1), n ​​and X 1 X 2 X 3 X 4 R 1 R 2 R 3 R 4A R 4B and R 4C The compounds are any combination of those listed in Tables A-4, A-5, A-6 and A-7.

[1129] [Table 11]

[1130] [Table A-4]

[1131]

[1132] [Table 12]

[1133] [Table A-5]

[1134]

[1135] [Table 13]

[1136] [Table A-6]

[1137]

[1138] [Table 14]

[1139] [Table A-7]

[1140]

[1141] Compound 26: 1 H-NMR(CDCl3)δ:9.07(2H,t),8.32(1H,t),7.64-7.58(2H,m),7.26-7.20(2H,m),3.22(2H,q),1.36(3H,t).

[1142] Compound 28: LCMS: 367 [M+H] + RT = 2.486 minutes

[1143] Compound 29: LCMS: 323[M+H] + RT = 2.414 minutes

[1144] Compound 30: LCMS: 327 [M+H] + RT = 2.316 minutes

[1145] Compound 31: LCMS: 365 [M+H] + RT = 2.402 minutes

[1146] Compound 32: LCMS: 387 [M+H] + RT = 2.444 minutes

[1147] Compound 33: LCMS: 433[M+H] + RT = 2.452 minutes

[1148] Compound 34: LCMS: 339 [M+H] + RT = 2.322 minutes

[1149] Compound 36: LCMS: 305[MH] - RT = 1.574 minutes

[1150] Compound 37: LCMS: 323[MH] - RT = 1.873 minutes

[1151] Compound 39: LCMS: 233 [M+H] + RT = 1.919 minutes

[1152] Compound 40: LCMS: 331 [M+H] + RT = 1.934 minutes

[1153] Compound 41: LCMS: 295 [M+H] + RT = 1.837 minutes

[1154] Compound 42: LCMS: 295 [M+H] + RT = 1.846 minutes

[1155] Compound 43: LCMS: 329 [M+H] + RT = 1.997 minutes

[1156] Compound 44: LCMS: 262 [M+H] + RT = 2.065 minutes

[1157] Compound 45: LCMS: 262 [M+H] + RT = 2.077 minutes

[1158] Compound 46: LCMS: 295 [M+H]+ RT = 2.068 minutes

[1159] Compound 47: LCMS: 335 [M+H] + RT = 1.882 minutes

[1160] Compound 48: LCMS: 306 [M+H] + RT = 1.317 minutes

[1161] Compound 50: LCMS: 349 [M+H] + RT = 1.862 minutes

[1162] Compound 52: LCMS: 381 [M+H] + RT = 2.481 minutes

[1163] Compound 53: LCMS: 377 [M+H] + RT = 2.352 minutes

[1164] Compound 54: LCMS: 377 [M+H] + RT = 2.470 minutes

[1165] Compound 55: LCMS: 369 [M+H] + RT = 2.235 minutes

[1166] Compound 56: LCMS: 319 [M+H] + RT = 2.213 minutes

[1167] Compound 57: LCMS: 331[M+H] + RT = 2.135 minutes

[1168] Compound 58: LCMS: 233 [M+H] + RT = 1.917 minutes

[1169] Compound 59: LCMS: 383 [M+H] + RT = 2.801 minutes

[1170] Compound 60: LCMS: 281 [M+H] + RT = 2.118 minutes

[1171] Compound 61: LCMS: 347 [M+H] + RT = 2.520 minutes

[1172] Compound 62: LCMS: 381 [M+H] +RT = 2.473 minutes

[1173] Compound 63: LCMS: 267 [M+H] + RT = 1.913 minutes

[1174] Compound 64: LCMS: 285 [M+H] + RT = 2.258 minutes

[1175] Compound 65: LCMS: 403 [M+H] + RT = 1.240 minutes

[1176] Reference Manufacturing Example 1

[1177] A mixture of 1.0 g of 2,4-dichloropyrimidine, 1.1 g of 3-fluoro-4-methylphenylboronic acid, 0.24 g of {1,1'-bis(diphenylphosphino)ferrocene}palladium(II) dichloride, 2.9 g of tripotassium phosphate, 20 mL of DME, and 2 mL of water was stirred under reflux for 7 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 = 2:1) to give 1.03 g of intermediate 1 as shown below.

[1178] [Chemical Formula 54]

[1179]

[1180] Intermediate 1: 1 H-NMR(CDCl3)δ:8.64(1H,d),7.82-7.74(2H,m),7.60(1H,d),7.33(1H,t),2.36(3H,d).

[1181] Refer to manufacturing example 1-1

[1182] The following shows an intermediate manufactured according to Reference Manufacturing Example 1.

[1183] In the compound represented by formula (IB-1) (hereinafter referred to as compound (IB-1)), X 1 X 2 X 3 X 4 X 5 R 2 R 3 R 4A R 4B and R 4C The compounds are any combination of those listed in [Table B-1].

[1184] [Chemical Formula 55]

[1185]

[1186] [Table 15]

[1187] [Table B-1]

[1188] intermediate <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[X 5 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 2 CH CH CH N F H H H Me F 3 CH N N CH Cl H H H Me F

[1189] Intermediate 2: 1 H-NMR(CDCl3)δ:8.26(1H,d),7.38-7.35(1H,m),7.34-7.27(3H,m),7.11-7.09(1H,m),2.35(3H,d).

[1190] Intermediate 3: 1 H-NMR(CDCl3)δ:9.15(1H,d),7.84(1H,d),7.79(1H,dd),7.73(1H,dd),7.35(1H,t),2.37(3H,d).

[1191] Reference Manufacturing Example 2

[1192] Under a nitrogen atmosphere, 0.31 g of sodium hydride (oil, 60%) and 10 mL of DMF were added to a mixture at 0 °C, and the mixture was stirred at room temperature for 30 minutes. 1.0 g of 2-bromo-4-chloropyridine was added to the resulting mixture, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 3:1) to give 1.1 g of intermediate 4 as shown below.

[1193] [Chemical Formula 56]

[1194]

[1195] Intermediate 4: 1 H-NMR(CDCl3)δ:8.12(1H,d),7.26(1H,d),7.04(1H,dd),2.95(2H,t),1.81-1.71(2H,m),1.08(3H,t).

[1196] Refer to manufacturing example 2-1

[1197] The following shows an intermediate manufactured according to Reference Manufacturing Example 2.

[1198] In the compound represented by formula (IB-2) (hereinafter referred to as compound (IB-2)), X1 X 2 X 3 X 4 X 6 and R 1 The compounds are any combination of those listed in [Table B-2].

[1199] [Chemical Formula 57]

[1200]

[1201] [Table 16]

[1202] [Table B-2]

[1203] intermediate <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[X 6 ]]> <![CDATA[R 1 ]]> 5 CH CH N CH Br Pr 6 N CH N CH Br Pr 7 CH CH N N Cl Pr 9 N CH N CH Cl Pr 10 CH CH N CH Br <![CDATA[CH2(4-OMe-Ph)]]> 15 CH CH N CH Br Bu 16 CH CH N CH Br c-Pn 17 CH CH N CH Br Ph 18 CH CH N CH Br 2-Thienyl 19 <![CDATA[CCH3]]> CH N CH Br Pr

[1204] Intermediate 5: 1 H-NMR(CDCl3)δ:8.40(1H,d),8.35(1H,d),7.59(1H,t),2.93(2H,t),1.76-1.65(2H,m),1.05(3H,t).

[1205] Intermediate 6: 1 H-NMR(CDCl3)δ:8.34(1H,s),8.27(1H,s),3.15(2H,t),1.80-1.70(2H,m),1.05(3H,t).

[1206] Intermediate 7: 1 H-NMR(CDCl3)δ:8.88(1H,d),7.21(1H,d),3.00(2H,t),1.85-1.75(2H,m),1.11(3H,t).

[1207] Intermediate 9: 1 H-NMR(CDCl3)δ:8.32(1H,s),8.18(1H,s),3.16(2H,t),1.81-1.70(2H,m),1.05(3H,t).

[1208] Intermediate 10: 1 H-NMR(CDCl3)δ:8.46(1H,d),8.39(1H,d),7.68(1H,t),7.21-7.16(2H,m),6.86-6.81(2H,m),4.08(2H,s),3.79(3H,s).

[1209] Intermediate 15: 1H-NMR(CDCl3)δ:8.44(1H,d),8.43(1H,d),7.74(1H,t),2.94(2H,t),1.70-1.61(2H,m),1.51-1.41(2H,m),0.94(3H,t).

[1210] Intermediate 16: 1 H-NMR(CDCl3)δ:8.47-8.44(2H,m),7.78(1H,t),3.66-3.56(1H,m),2.18-2.05(2H,m),1.86-1.73(2H,m),1.71-1.56(4H,m).

[1211] Intermediate 17: 1 H-NMR(CDCl3)δ:8.47(1H,d),8.39(1H,d),7.63(1H,t),7.47-7.36(5H,m).

[1212] Intermediate 18: 1 H-NMR(CDCl3)δ:8.43(1H,d),8.33(1H,d),7.56(1H,dd),7.53(1H,t),7.35(1H,dd),7.13(1H,dd).

[1213] Intermediate 19: 1 H-NMR(CDCl3)δ:8.48(1H,s),8.36(1H,s),2.90(2H,t),2.50(3H,s),1.75-1.63(2H,m),1.05(3H,t).

[1214] Reference Manufacturing Example 3

[1215] 1.16 g of sodium ethanesulfinate was added to a mixture of 1.49 g of 2,4-dichloropyrimidine and 20 mL of DMSO, and the mixture was stirred at room temperature for 8 hours. 20 mL of saturated brine was added to the resulting mixture, and extraction was performed using MTBE. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:1) to give 0.76 g of intermediate 8 as shown in the formula below.

[1216] [Chemical Formula 58]

[1217]

[1218] Intermediate 8: 1H-NMR(CDCl3)δ:9.00(1H,d),7.97(1H,d),3.51(2H,q),1.39(3H,t).

[1219] Refer to manufacturing example 4

[1220] 48.8 g of mCPBA (75% purity, containing 25% water) was added to a mixture of 18.5 g of 2-chloro-6-(propylthio)pyrazine and 250 mL of chloroform at 0 °C, and the mixture was stirred at room temperature for 2 hours. 1.43 g of mCPBA (75% purity, containing 25% water) was added to the resulting mixture, and the mixture was allowed to stand overnight. 400 mL of saturated sodium bicarbonate aqueous solution was added to the resulting mixture, and after stirring for 1 hour, extraction was performed using chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to give 24.7 g of intermediate 11.

[1221] [Chemical Formula 59]

[1222]

[1223] Intermediate 11: 1 H-NMR(CDCl3)δ:9.18(1H,s),8.86(1H,s),3.39(2H,q),1.85(2H,m),1.08(3H,t).

[1224] Refer to manufacturing example 4-1

[1225] The following shows an intermediate manufactured according to Reference Manufacturing Example 4.

[1226] In the compound represented by formula (IB-3) (hereinafter referred to as compound (IB-3)), X 1 X 2 X 3 X 4 X 6 and R 1 These are compounds in any combination listed in [Table B-3].

[1227] [Chemical Formula 60]

[1228]

[1229] [Table 17]

[1230] [Table B-3]

[1231] intermediate <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[X 6 ]]> <![CDATA[R 1 ]]> 12 CH CH N CH Br Et 13 CH CH N CH Br Pr 20 CH CH N CH Br Bu 21 CH CH N CH Br c-Pn 22 CH CH N CH Br Ph 23 CH CH N CH Br 2-Thienyl 24 <![CDATA[CCH3]]> CH N CH Br Pr

[1232] Intermediate 12: 1H-NMR(CDCl3)δ:9.02(1H,d),8.95(1H,d),8.34(1H,t),3.22-3.17(2H,q),1.35(3H,t).

[1233] Intermediate 13: 1 H-NMR(CDCl3)δ:9.01(1H,d),8.94(1H,d),8.33(1H,t),3.16-3.11(2H,m),1.85-1.75(2H,m),1.05(3H,t).

[1234] Intermediate 20: 1 H-NMR(CDCl3)δ:9.02(1H,d),8.95(1H,d),8.34(1H,t),3.20-3.12(2H,m),1.81-1.67(2H,m),1.51-1.38(2H,m),0.93(3H,t).

[1235] Intermediate 21: 1 H-NMR(CDCl3)δ:9.01(1H,d),8.93(1H,d),8.33(1H,t),3.57-3.49(1H,m),2.15-2.03(2H,m),1.99-1.77(4H,m),1.73-1.59(2H,m).

[1236] Intermediate 22: 1 H-NMR(CDCl3)δ:9.03(1H,d),8.83(1H,d),8.34(1H,t),8.00-7.96(2H,m),7.69-7.63(1H,m),7.62-7.55(2H,m).

[1237] Intermediate 23: 1 H-NMR(CDCl3)δ:9.08(1H,d),8.85(1H,d),8.37(1H,t),7.80-7.74(2H,m),7.19-7.14(1H,m).

[1238] Intermediate 24: 1 H-NMR(CDCl3)δ:9.05(1H,s),8.91(1H,s),3.18-3.12(2H,m),2.79(3H,s),1.85-1.75(2H,m),1.05(3H,t).

[1239] Reference Manufacturing Example 5

[1240] 0.41 g of aluminum chloride was added to a mixture of 0.7 g of compound 120 and 10 mL of toluene at room temperature, and the mixture was stirred overnight at room temperature. The resulting mixture was added dropwise to ice water, followed by the addition of a 5% sodium hydroxide aqueous solution. After stirring the resulting mixture at room temperature for 1 hour, it was neutralized with 1 M hydrochloric acid and extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate = 1:3) to give 0.38 g of intermediate 14 as shown below.

[1241] [Chemical Formula 61]

[1242]

[1243] Intermediate 14: 1 H-NMR(CDCl3)δ:8.59(1H,d),8.48(1H,d),7.76(1H,t),7.33-7.18(3H,m),3.49(1H,s),2.33(3H,d).

[1244] Refer to manufacturing example 5-1

[1245] The following shows an intermediate manufactured according to Reference Manufacturing Example 5.

[1246] In the compound represented by formula (IB-4) (hereinafter referred to as compound (IB-4)), X 1 X 2 X 3 X 4 R 2 R 3 R 4A R 4B and R 4C These are compounds in any combination listed in [Table B-4].

[1247] [Chemical Formula 62]

[1248]

[1249] [Table 18]

[1250] [Table B-4]

[1251] intermediate <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> <![CDATA[X 3 ]]> <![CDATA[X 4 ]]> <![CDATA[R 2 ]]> <![CDATA[R 3 ]]> <![CDATA[R 4A ]]> <![CDATA[R 4B ]]> <![CDATA[R 4C ]]> 25 CH CH N CH H H H Cl H 26 CH CH N CH H H H Me H

[1252] Intermediate 25: 1 H-NMR(CDCl3)δ:8.59(1H,d),8.50(1H,d),7.76(1H,t),7.51-7.44(4H,m),3.50(1H,s).

[1253] Intermediate 26: 1 H-NMR(CDCl3)δ:8.61(1H,d),8.46(1H,d),7.78(1H,t),7.47-7.43(2H,m),7.31-7.27(2H,m),3.48(1H,s),2.41(3H,s).

[1254] The following shows the compound and examples of the compound manufactured according to the above manufacturing method and manufacturing example.

[1255] In the compound shown in formula (A-1) (hereinafter referred to as compound (A-1)), n is 0, R 6 R 7 and R 8 Each is a hydrogen atom, R 1 R 4A R 4B R 4C R 2 and R 3 The combination is any combination of compounds recorded in combination A (hereinafter referred to as compound group SX1).

[1256] [Chemical Formula 63]

[1257]

[1258] Combination A consists of substituents numbered A1 to A1863. Substituents numbered A1 to A1863 refer to the R group in the compounds shown in formula (A-1), (A-2), (A-3), (A-4), (A-5), (A-6), (A-7), (A-8), (A-9), and (A-10). 1 R 4A R 4B R 4C R 2 and R 3 The combination of [substituent number; R] is denoted below as [substituent number; R]. 1 ,R 4A ,R 4B ,R 4C ,R 2 ,R 3 ].

[1259] For example, substituent number A5 means: R 1 For ethyl, R 4A R 4B and R 4C Each is a methyl group, R 2and R 3 It is a combination of hydrogen atoms.

[1260] Combination A

[1261] [A1;Et,Me,H,H,H,H]、[A2;Et,H,Me,H,H,H]、[A3;Et,Me,Me,H,H,H]、[A4;Et,Me,H,Me,H,H]、[A5;Et,Me,Me,Me,H,H]、[A6;Et,F,H,H,H,H]、[A7;Et,H,F,H,H,H]、[A8;Et,F,F,H,H,H]、[A9;Et,F,H,F,H,H]、[A10;Et,F,F,F,H,H]、[A11;Et,Cl,H,H,H,H]、[A12;Et,H,Cl,H,H,H]、[A13;Et,Cl,Cl,H,H,H]、[A14;Et,Cl,H,Cl,H,H]、[A15;Et,Cl,Cl,Cl,H,H]、[A16;Et,Br,H,H,H,H]、[A17;Et,H,Br,H,H,H]、[A18;Et,Br,Br,H,H,H]、[A19;Et,Br,H,Br,H,H]、[A20;Et,Br,Br,Br,H,H]、[A21;Et,I,H,H,H,H]、[A22;Et,H,I,H,H,H]、[A23;Et,I,I,H,H,H]、[A24;Et,I,H,I,H,H]、[A25;Et,I,I,I,H,H]、[A26;Et,Et,H,H,H,H]、[A27;Et,H,Et,H,H,H]、[A28;Et,Et,H,Et,H,H]、[A29;Et,CF3,H,H,H,H]、[A30;Et,H,CF3,H,H,H]、[A31;Et,CF3,H,CF3,H,H]、[A32;Et,c-Pr,H,H,H,H]、[A33;Et,H,c-Pr,H,H,H]、[A34;Et,OMe,H,H,H,H]、[A35;Et,H,OMe,H,H,H]、[A36;Et,OMe,H,OMe,H,H]、[A37;Et,SMe,H,H,H,H]、[A38;Et,H,SMe,H,H,H]、[A39;Et,S(O)Me,H,H,H,H]、[A40;Et,H,S(O)Me,H,H,H]、[A41;Et,S(O)2Me,H,H,H,H]、[A42;Et,H,S(O)2Me,H,H,H]、[A43;Et,C(O)OMe,H,H,H,H]、[A44;Et,H,C(O)OMe,H,H,H]、[A45;Et,C(O)Me,H,H,H,H]、[A46;Et,H,C(O)Me,H,H,H]、[A47;Et,CN,H,H,H,H]、[A48;Et,H,CN,H,H,H]、[A49;Et,NO2,H,H,H,H]、[A50;Et,H,NO2,H,H,H]、[A51;Et,NH2,H,H,H,H]、[A52;Et,H,NH...

Claims

1. A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with a compound represented by formula (I) or its N-oxide or salt thereof, [Chemical formula 1] In formula (I), n represents 0, 1 or 2, R 1 represents a C1-C6 alkyl group, a C2-C6 alkynyl group {the C1-C6 alkyl group and the C2-C6 alkynyl group may have one or more substituents selected from group A}, a C2-C6 alkenyl group which may have one or more substituents selected from group C, 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 may have one or more substituents selected from group B}, a C6-C10 aryl group which may have one or more substituents selected from group F, a 5-10 membered aromatic heterocyclic group which may have one or more substituents selected from group D, or NR 33 R 34 , R 2 and R 3 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from group B, OR 9 , SR 10 、S(O)R 11 、S(O)2R 12 NR 13 R 14 、C(O)R 15 , nitro group, cyano group, halogen atom or hydrogen atom, R 4 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A, 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 may have one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D}, OR 16 , SR 17 、S(O)R 18 、S(O)2R 19 NR 20 R 21 、C(O)R 22 , C(R 23 )=NOR 24 , cyano, nitro, amino, hydroxyl or halogen atoms, q means 1, 2 or 3, When q is 2 or 3, 2 or 3 R 4 Can be the same or different, X 1 , X 2 , X 3 and X 4 The combination of: X 1 CR 5 , X 2 CR 6 , X 3 CR 7 , X 4 is a combination of nitrogen atoms; X 1 CR 5 , X 2 CR 6 , X 3 is a nitrogen atom, X 4 CR 8 combination of; X 1 CR 5 , X 2 is a nitrogen atom, X 3 CR 7A , X 4 CR 8 combination of; X 1 is a nitrogen atom, X 2 CR 6 , X 3 CR 7B , X 4 CR 8 combination of; X 1 is a nitrogen atom, X 2 is a nitrogen atom, X 3 CR 7C , X 4 It is a combination of CH; X 1 is a nitrogen atom, X 2 is a nitrogen atom, X 3 CH, X 4 CR 8 combination of; X 1 is a nitrogen atom, X 2 CR 6 , X 3 is a nitrogen atom, X 4 CR 8 combination of; X 1 is a nitrogen atom, X 2 CR 6 , X 3 CR 7 , X 4 is a combination of nitrogen atoms; X 1 CR 5 , X 2 is a nitrogen atom, X 3 is a nitrogen atom, X 4 CR 8 combination of; X 1 CR 5 , X 2 is a nitrogen atom, X 3 CH, X 4 is a combination of nitrogen atoms; X 1 CH, X 2 is a nitrogen atom, X 3 CR 7D , X 4 is a combination of nitrogen atoms; or, X 1 CR 5 , X 2 CR 6 , X 3 is a nitrogen atom, X 4 is the combination of nitrogen atoms, R 5 , R 6 , R 7 and R 8 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from group B, OR 25 , SR 26 、S(O)R 27 、S(O)2R 28 NR 29 R 30 、C(O)R 31 , nitro group, cyano group, halogen atom or hydrogen atom, R 9 , R 10 , R 13 and R 29 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group or a hydrogen atom which may be substituted by one or more halogen atoms, R 7A represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from Group B, OR 25 , SR 26 、S(O)R 27 、S(O)2R 28 NR 29 R 32 、C(O)R 31 , nitro group, cyano group, halogen atom or hydrogen atom, R 7B represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from Group B, OR 25 NR 29 R 30 、C(O)R 31 , nitro group, cyano group, halogen atom or hydrogen atom, R 7C represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from Group B, OR 25 NR 29 R 30 、C(O)R 31 , nitro, cyano or halogen atoms, R 7D represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from Group B, OR 25 、S(O)R 27 、S(O)2R 28 NR 29 R 30 、C(O)R 31 , nitro, cyano, fluorine, chlorine or iodine, R 11 , R 12 , R 25 , R 26 , R 27 and R 28 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 14 and R 30 are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted by one or more halogen atoms} or a hydrogen atom, R 15 , R 22 and R 31 are the same or different from each other, and represent 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 by one or more halogen atoms}, R 16 represents a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, or a (C2-C8 dialkylamino)carbonyl group which may have one or more substituents selected from Group A {the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group, the (C1-C6 alkylamino)carbonyl group a phenyl group, a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may have one or more substituents selected from group D} or a hydrogen atom, R 17 , R 18 , R 19 and R 24 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group, a C3-C8 alicyclic hydrocarbon group, a 3-8-membered non-aromatic heterocyclic group {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}, a phenyl group, or a 5-6-membered aromatic heterocyclic group {the phenyl group and the 5-6-membered aromatic heterocyclic group may have one or more substituents selected from group D}, R 20 represents a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group A, 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 may have one or more substituents selected from group B}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have one or more substituents selected from group D}, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group or a C1-C6 alkylsulfonyl group {the (C1-C6 alkyl)carbonyl group, the (C1-C6 alkoxy)carbonyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, R 21 and R 23 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group or a hydrogen atom which may have one or more substituents selected from Group A, R 32 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a (C1-C6 alkyl)carbonyl group or a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted with one or more halogen atoms}, R 33 and R 34 are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may have one or more substituents selected from group G, a C3-C6 alicyclic hydrocarbon group which may have one or more halogen atoms, or a hydrogen atom, Adjacent R 2 and R 4 Together with the carbon atoms to which they are bonded, they may form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have one or more substituents selected from group B}, a benzene ring or a 5-6-membered aromatic heterocycle {the benzene ring and the 5-6-membered aromatic heterocycle may have one or more substituents selected from group E}, Two adjacent R 4 and R 4 Together with the carbon atoms to which they are bonded, they may form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have one or more substituents selected from Group B}, a benzene ring or a 5-6-membered aromatic heterocycle {the benzene ring and the 5-6-membered aromatic heterocycle may have one or more substituents selected from Group E}; Group A: a group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {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}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, a halogen atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group B: the group consisting of oxo, thio, C1-C6 chain hydrocarbon, C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 chain hydrocarbon, the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, hydroxyl, sulfanyl, halogen atoms and cyano; Group C: a group consisting of a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group, a 3-8 membered non-aromatic heterocyclic group {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}, a phenyl group, a 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may be substituted with one or more substituents selected from Group D}, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group D: C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino may be substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from Group B, an amino group, a nitro group, a cyano group, a hydroxyl group, a sulfanyl group and a halogen atom; Group E: the group consisting of C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, hydroxyl group, sulfanyl group, halogen atom and cyano group; Group F: C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, -C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino which may be substituted with one or more halogen atoms}, the group consisting of a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from group B, an amino group, a cyano group, a hydroxyl group, a sulfanyl group and a halogen atom; Group G: A group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may be substituted by one or more halogen atoms}, a halogen atom and a cyano group.

2. The method for controlling plant diseases according to claim 1, wherein: The compound represented by formula (I) or its N-oxide or salt thereof is R 1 A compound which is a C1-C6 alkyl group, a C2-C6 alkynyl group {the C1-C6 alkyl group and the C2-C6 alkynyl group may have one or more substituents selected from group A}, a C2-C6 alkenyl group which may have one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}, or its N-oxide, or a salt thereof.

3. The method of claim 2, wherein: The compound represented by formula (I) or its N-oxide or salt thereof is X 1 , X 2 , X 3 and X 4 The combination is the following combination of compounds or their N oxides or salts thereof: X 1 CR 5 , X 2 CR 6 , X 3 CR 7 , X 4 is a combination of nitrogen atoms; X 1 CR 5 , X 2 CR 6 , X 3 is a nitrogen atom, X 4 CR 8 Combination of; X 1 CR 5 , X 2 is a nitrogen atom, X 3 CR 7A , X 4 CR 8 Combination of; X 1 is a nitrogen atom, X 2 CR 6 , X 3 CR 7B , X 4 CR 8 Combination of; X 1 is a nitrogen atom, X 2 CR 6 , X 3 is a nitrogen atom, X 4 CR 8 Combination of; X 1 CR 5 , X 2 is a nitrogen atom, X 3 is a nitrogen atom, X 4 CR 8 or, X 1 CR 5 , X 2 CR 6 , X 3 is a nitrogen atom, X 4 A combination of nitrogen atoms.

4. The method according to claim 2 or claim 3, wherein: The compound represented by formula (I) or its N-oxide or salt thereof is R 1 A compound which is a C2-C6 alkyl group, a C2-C6 alkynyl group {the C2-C6 alkyl group and the C2-C6 alkynyl group may have one or more substituents selected from group A}, a methyl group having one or more substituents selected from group C, or a C3-C8 alicyclic hydrocarbon group {the C3-C8 alicyclic hydrocarbon group may have one or more substituents selected from group B}, or its N-oxide, or a salt thereof.

5. A compound represented by formula (II) or an N-oxide thereof or a salt thereof, [Chemical formula 2] In formula (II), na means 0, 1 or 2, qa means 1, 2 or 3, In the case of qa of 2 or 3, 2 or 3 R 4a Can be the same or different, R 1a represents a C2-C6 alkyl group, a C2-C6 alkynyl group {the C2-C6 alkyl group and the C2-C6 alkynyl group may have a member selected from the group A a One or more substituents in Group F a The C2-C6 alkenyl group having one or more substituents in the group B may have a A C3-C8 alicyclic hydrocarbon group having one or more substituents selected from Group C a methyl, or one or more substituents selected from Group G a A 5-6 membered aromatic heterocyclic group having one or more substituents, R 8a represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a a C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7a , SR 9a 、S(O)R 10a 、S(O)2R 11a NR 12a R 13a 、C(O)R 14a , nitro group, cyano group, halogen atom or hydrogen atom, R 2a and R 3a The same or different from each other, representing a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a a C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 15a , SR 16a 、S(O)R 17a 、S(O)2R 18a NR 19a R 20a 、C(O)R 21a , nitro group, cyano group, halogen atom or hydrogen atom, X a , R 4a and R 6a The combination of: X a is a nitrogen atom, R 4a may have a selected from group A a wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B a phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a One or more substituents in 23a , SR 24a 、S(O)R 25a 、S(O)2R 26a NR 27a R 28a 、C(O)R 29a , C(R 30a )=NOR 31a , cyano, nitro, amino, hydroxyl or halogen atoms, R 6a is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a a C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7a , SR 9a 、S(O)R 10a 、S(O)2R 11a NR 12a R 13a 、C(O)R 14a , a nitro group, a cyano group, a halogen atom or a hydrogen atom; or, X a CR 5a , R 4a may have a selected from group F a One or more substituents in the methyl group, CH2F group, CHF2 group, may have a substituent selected from Group A a wherein at least one substituent is a C2-C6 chain hydrocarbon group, 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 a substituent selected from Group B a phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a One or more substituents in 23a , SR 24a 、S(O)R 25a 、S(O)2R 22a NR 27a R 28a 、C(O)R 29a , C(R 30a )=NOR 31a , cyano, nitro, amino, hydroxyl or halogen atoms, R 6a is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a a C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7a , nitro, fluorine, bromine, iodine or hydrogen, R 5a represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a a C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7a , SR 9a 、S(O)R 10a 、S(O)2R 11a NR 12a R 13a 、C(O)R 14a , nitro group, cyano group, halogen atom or hydrogen atom, R 7a , R 9a , R 10a , R 11a , R 15a , R 16a , R 17a and R 18a are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 12a and R 19a are the same or different from each other, and represent a C1-C6 chain hydrocarbon group or a hydrogen atom which may be substituted by one or more halogen atoms, R 13a and R 20a are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted by one or more halogen atoms} or a hydrogen atom, R 14a , R 21a and R 29a are the same or different from each other, and represent 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 by one or more halogen atoms}, R 23a Indicates that there may be a selected group A a wherein at least one substituent is a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {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 may be substituted with at least one halogen atom}, 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 may have a substituted group selected from Group B a phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a one or more substituents in} or hydrogen atoms, R 22a , R 24a , R 25a and R 31a The same or different from each other, indicating that they may have a a wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B a phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a One or more substituents in R 26a Indicates that the a The methyl group of one or more substituents in the a wherein at least one substituent is a C2-C6 chain hydrocarbon group, 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 a substituent selected from Group B a phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a One or more substituents in R 27a Indicates that there may be a selected group A a wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B a phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D a substituted with one or more halogen atoms}, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl or C1-C6 alkylsulfonyl {the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, R 28a and R 30a The same or different from each other, indicating that they may have a a One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom, Adjacent R 2a and R 4a Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have a member selected from Group B a 1 or more substituents in}, a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring may have a substituent selected from Group E a One or more substituents in Two adjacent R 4a and R 4a Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have a member selected from Group B a 1 or more substituents in}, a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring may have a substituent selected from Group E a More than one substituent in}; Group A a : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B a substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D a substituted with one or more substituents in}, a halogen atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group B a : a group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group C a : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B a substituted with one or more substituents in}, and a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may be selected from group D a A group consisting of one or more substituents in substituted with}; Group D a : C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkyl The C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino may be substituted with one or more halogen atoms}, may have a halogen atom selected from Group B a The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, sulfanyl groups and halogen atoms having one or more substituents; Group E a : a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group F a : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B a substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D a substituted with one or more substituents in}, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group G a : A group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a C2-C8 dialkylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C1-C6 alkylamino group and the C2-C8 dialkylamino group may be substituted with one or more halogen atoms}, a C3-C8 alicyclic hydrocarbon group which may have one or more substituents selected from group B, an amino group, a nitro group, a cyano group, a hydroxyl group, a sulfanyl group and a halogen atom.

6. The compound according to claim 5, or its N-oxide or salt thereof, wherein: R 1a is C2-C6 alkyl, C2-C6 alkynyl {the C2-C6 alkyl and the C2-C6 alkynyl may have a member selected from Group A a One or more substituents in Group F a The C2-C6 alkenyl group having one or more substituents in the group B may have a C3-C8 alicyclic hydrocarbon group having one or more substituents, or having a substituent selected from Group C a 1 or more methyl substituents.

7. The compound according to claim 6, or its N-oxide or salt thereof, wherein: X a is a nitrogen atom, R 4a may have a selected from group A a C1-C6 chain hydrocarbon group with one or more substituents, OR 23a NR 27a R 28a , cyano, nitro, hydroxyl or halogen atoms.

8. The compound according to claim 6, or its N-oxide or salt thereof, wherein: X a CR 5a , R 4a is methyl, may have a a C2-C6 chain hydrocarbon group with one or more substituents, OR 23a , SR 24a 、S(O)R 25a 、S(O)2R 22a NR 27a R 28a , cyano, nitro, hydroxyl or halogen atoms.

9. The compound according to any one of claims 5 to 8, or its N-oxide or salt thereof, wherein R 6a A hydrogen atom.

10. A compound represented by formula (III) or its N-oxide or a salt thereof, [Chemical formula 3] In formula (III), nb means 0, 1 or 2, qb means 1, 2 or 3, When qb is 2 or 3, 2 or 3 R 4b Can be the same or different, R 1b Indicates that there may be a selected group G b phenyl having one or more substituents, R 8b represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a b C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7b , SR 9b 、S(O)R 10b 、S(O)2R 11b NR 12b R 13b 、C(O)R 14b , nitro group, cyano group, halogen atom or hydrogen atom, R 2b and R 3b The same or different from each other, representing a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a b C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 15b , SR 16b 、S(O)R 17b 、S(O)2R 18b NR 19b R 20b 、C(O)R 21b , nitro group, cyano group, halogen atom or hydrogen atom, X b , R 4b and R 6b The combination of: X b is a nitrogen atom, R 4b may have a selected from group F b One or more substituents in the methyl group, CH2F group, CHF2 group, may have a substituent selected from Group A b The C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group having one or more substituents in the b phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b One or more substituents in 23b , SR 24b 、S(O)R 25b 、S(O)2R 22b NR 27b R 28b 、C(O)R 29b , C(R 30b )=NOR 31b , cyano, nitro, hydroxyl, amino or halogen atoms, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a b C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7b , SR 9b 、S(O)R 10b 、S(O)2R 11b NR 12b R 13b 、C(O)R 14b , a nitro group, a halogen atom or a hydrogen atom; or X b CR 5b , R 4b may have a selected from group F b One or more substituents in the methyl group, CH2F group, CHF2 group, may have a substituent selected from Group A b The C2-C3 chain hydrocarbon group, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group having one or more substituents in the b phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b One or more substituents in 32b , SR 24b 、S(O)R 25b 、S(O)2R 22b NR 27b R 28b 、C(O)R 29b , C(R 30b )=NOR 31b , cyano, nitro, hydroxyl or halogen atoms, R 6b is a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a b C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7b , nitro, fluorine, bromine, iodine or hydrogen, R 5b represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a b C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7b , SR 9b 、S(O)R 10b 、S(O)2R 11b NR 12b R 13b 、C(O)R 14b , nitro group, cyano group, halogen atom or hydrogen atom, R 7b , R 9b , R 10b , R 11b , R 15b , R 16b , R 17b and R 18b are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 12b and R 19b are the same or different from each other, and represent a C1-C6 chain hydrocarbon group or a hydrogen atom which may be substituted by one or more halogen atoms, R 13b and R 20b are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted by one or more halogen atoms} or a hydrogen atom, R 14b , R 21b and R 29b are the same or different from each other, and represent 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 by one or more halogen atoms}, R 23b Indicates that there may be a selected group A b wherein at least one substituent is a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {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 may be substituted with at least one halogen atom}, 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 may have a substituted group selected from Group B b phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b one or more substituents in} or hydrogen atoms, R 22b , R 24b , R 25b and R 31b The same or different from each other, indicating that they may have a b wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B b phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b One or more substituents in R 27b Indicates that there may be a selected group A b wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B b phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b substituted with one or more halogen atoms}, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl or C1-C6 alkylsulfonyl {the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, R 28b and R 30b The same or different from each other, indicating that they may have a b One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom, R 32b Indicates that the b The methyl group of one or more substituents in the b wherein at least one substituent is a C2-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {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 may be substituted with at least one halogen atom}, 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 may have a substituted group selected from Group B b phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D b one or more substituents in} or hydrogen atoms, Adjacent R 2b and R 4b Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have a member selected from Group B b 1 or more substituents in}, a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring may have a substituent selected from Group E b One or more substituents in Two adjacent R 4b and R 4b Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have a member selected from Group B b 1 or more substituents in}, a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring may have a substituent selected from Group E b More than one substituent in}; Group A b : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B b substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D b substituted with one or more substituents in}, a halogen atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group B b : a group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group D b : C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkyl The C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino may be substituted with one or more halogen atoms}, may have a halogen atom selected from Group B b The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, sulfanyl groups and halogen atoms having one or more substituents; Group E b : a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group F b : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B b substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D b substituted with one or more substituents in}, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group G b : C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkyl The C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino may be substituted with one or more halogen atoms}, may have a halogen atom selected from Group B b The group consisting of a C3-C8 alicyclic hydrocarbon group, an amino group, a cyano group, a hydroxyl group, a sulfanyl group and a halogen atom as substituent.

11. A compound represented by formula (IV) or an N-oxide thereof or a salt thereof, [Chemical formula 4] In formula (IV), nc represents 0, 1 or 2, qc means 1, 2 or 3, In the case of qc of 2 or 3, 2 or 3 R 4c Can be the same or different, X c Represents nitrogen atom or CR 5c , R 1c Indicates that it can have a selected from group B c 3-8 membered non-aromatic heterocyclic group or NR 33c R 34c , R 8c represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a c C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7c , SR 9c 、S(O)R 10c 、S(O)2R 11c NR 12c R 13c 、C(O)R 14c , nitro group, cyano group, halogen atom or hydrogen atom, R 2c and R 3c The same or different from each other, representing a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a c C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 15c , SR 16c 、S(O)R 17c 、S(O)2R 18c NR 19c R 20c 、C(O)R 21c , nitro group, cyano group, halogen atom or hydrogen atom, R 4c may have a selected from group A c wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B c }, a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may have a substituent selected from Group D c One or more substituents in 23c , SR 24c 、S(O)R 25c 、S(O)2R 22c NR 27c R 28c 、C(O)R 29c , C(R 30c )=NOR 31c , cyano, nitro, amino, hydroxyl or halogen atoms, R 6c represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a c C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7c , SR 9c 、S(O)R 10c 、S(O)2R 11c NR 12c R 13c 、C(O)R 14c , nitro group, cyano group, halogen atom or hydrogen atom, R 5c represents a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, and may have a c C3-C8 alicyclic hydrocarbon group with one or more substituents, OR 7c , SR 9c 、S(O)R 10c 、S(O)2R 11c NR 12c R 13c 、C(O)R 14c , nitro group, cyano group, halogen atom or hydrogen atom, R 7c , R 9c , R 10c , R 11c , R 15c , R 16c , R 17c and R 18c are the same or different from each other, and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, R 12c and R 19c are the same or different from each other, and represent a C1-C6 chain hydrocarbon group or a hydrogen atom which may be substituted by one or more halogen atoms, R 13c and R 20c are the same or different from each other and represent a C1-C6 chain hydrocarbon group which may be substituted by one or more halogen atoms, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group {the (C1-C6 alkyl)carbonyl group and the (C1-C6 alkoxy)carbonyl group may be substituted by one or more halogen atoms} or a hydrogen atom, R 14c , R 21c and R 29c are the same or different from each other, and represent 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 by one or more halogen atoms}, R 23c Indicates that there may be a selected group A c wherein at least one substituent is a C1-C6 chain hydrocarbon group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a (C2-C8 dialkylamino)carbonyl group {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 may be substituted with at least one halogen atom}, 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 may have a substituted group selected from Group B c phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D c one or more substituents in} or hydrogen atoms, R 22c , R 24c , R 25c and R 31c The same or different from each other, indicating that they may have a c wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B c phenyl or a 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D c One or more substituents in R 27c Indicates that there may be a selected group A c wherein one or more substituents are C1-C6 chain hydrocarbon groups, C3-C8 alicyclic hydrocarbon groups, 3-8 membered non-aromatic heterocyclic groups {the C3-C8 alicyclic hydrocarbon groups and the 3-8 membered non-aromatic heterocyclic groups may have a substituent selected from Group B c phenyl, 5-6 membered aromatic heterocyclic group {the phenyl group and the 5-6 membered aromatic heterocyclic group may have a substituent selected from group D c substituted with one or more halogen atoms}, (C1-C6 alkyl)carbonyl, (C1-C6 alkoxy)carbonyl or C1-C6 alkylsulfonyl {the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, R 28c and R 30c The same or different from each other, indicating that they may have a c One or more substituents in the C1-C6 chain hydrocarbon group or hydrogen atom, R 33c Indicates that there may be a selected group G c a C1-C6 chain hydrocarbon group having one or more substituents, a C3-C6 cycloalkyl group which may have one or more halogen atoms, or a hydrogen atom, R 34c Indicates that there may be a selected group G c a C1-C6 chain hydrocarbon group having one or more substituents, or a C3-C6 cycloalkyl group which may have one or more halogen atoms, Adjacent R 2c and R 4c Together with the carbon atoms to which they are bonded, they can form a C5-C6 alicyclic hydrocarbon, a 5-6-membered non-aromatic heterocycle {the C5-C6 alicyclic hydrocarbon and the 5-6-membered non-aromatic heterocycle may have a member selected from Group B c 1 or more substituents in}, a benzene ring or a 5-6-membered aromatic heterocyclic ring {the benzene ring and the 5-6-membered aromatic heterocyclic ring may have a substituent selected from Group E c One or more substituents in Two adjacent R 4c and R 4c Together with the carbon atoms to which they are bonded, they may form a c C5-C6 alicyclic hydrocarbon having one or more substituents, which may have a substituent selected from Group C c 5-6 membered non-aromatic heterocyclic ring, benzene ring or 5-6 membered aromatic heterocyclic ring {the benzene ring and the 5-6 membered aromatic heterocyclic ring may have a ring selected from Group E c More than one substituent in}; Group A c : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B c substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D c substituted with one or more substituents in}, a halogen atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group B c : a group consisting of an oxo group, a thio group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group C c : a group consisting of a thio group, a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group D c : C1-C6 chain hydrocarbon group, C1-C6 alkoxy group, C1-C6 alkylsulfanyl group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 alkylamino group, C2-C8 dialkylamino group, (C1-C6 alkyl)carbonyl group, (C1-C6 alkoxy)carbonyl group, (C1-C6 alkylamino)carbonyl group, (C2-C8 dialkylamino)carbonyl group, (C1-C6 alkyl)carbonylamino group, (C1-C6 alkoxy)carbonylamino group {the C1-C6 chain hydrocarbon group, the C1-C6 alkyl The C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl, the C1-C6 alkylsulfonyl, the C1-C6 alkylamino, the C2-C8 dialkylamino, the (C1-C6 alkyl)carbonyl, the (C1-C6 alkoxy)carbonyl, the (C1-C6 alkylamino)carbonyl, the (C2-C8 dialkylamino)carbonyl, the (C1-C6 alkyl)carbonylamino and the (C1-C6 alkoxy)carbonylamino may be substituted with one or more halogen atoms}, may have a halogen atom selected from Group B c The group consisting of C3-C8 alicyclic hydrocarbon groups, amino groups, nitro groups, cyano groups, hydroxyl groups, sulfanyl groups and halogen atoms having one or more substituents; Group E c : a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group and the C1-C6 alkylsulfonyl group may be substituted with one or more halogen atoms}, a hydroxyl group, a sulfanyl group, a halogen atom and a cyano group; Group F c : C1-C6 alkoxy, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl {the C1-C6 alkoxy, the C1-C6 alkylsulfanyl, the C1-C6 alkylsulfinyl and the C1-C6 alkylsulfonyl may be substituted with one or more halogen atoms}, C3-C8 alicyclic hydrocarbon group, 3-8 membered non-aromatic heterocyclic group {the C3-C8 alicyclic hydrocarbon group and the 3-8 membered non-aromatic heterocyclic group may be selected from group B c substituted with one or more substituents in}, phenyl, 5-6 membered aromatic heterocyclic group {the phenyl and the 5-6 membered aromatic heterocyclic group can be selected from group D c substituted with one or more substituents in}, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group and a sulfanyl group; Group G c : A group consisting of a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, a C1-C3 alkylthio group {the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may be substituted by one or more halogen atoms}, a halogen atom and a cyano group.

12. An agricultural chemical composition comprising an inactive carrier and the compound according to any one of claims 5 to 11, or an N-oxide thereof, or a salt thereof.

13. A composition comprising one or more components selected from the group consisting of Group (a), Group (b), Group (c) and Group (d), and the compound or N-oxide thereof or a salt thereof according to any one of claims 5 to 11: Group (a): a group consisting of insecticidal active ingredients, acaricidal active ingredients and nematicidal active ingredients; Group (b): fungicidal active ingredients; Group (c): plant growth regulating ingredients; Group (d): repellent ingredients.

14. A method for controlling plant diseases, which is carried out by treating plants or soil for cultivating plants with an effective amount of the compound according to any one of claims 5 to 11 or its N-oxide or salt thereof, or an effective amount of the composition according to claim 13.

15. Use of the compound according to any one of claims 5 to 11, or its N-oxide or salt thereof, or the composition according to claim 13 for controlling plant diseases.

16. Seeds or vegetative propagation organs, which retain an effective amount of the compound according to any one of claims 5 to 11 or its N-oxide or salt thereof, or an effective amount of the composition according to claim 13.

17. A compound represented by formula (V), [Chemical formula 5] In formula (V), R 1d represents a C2-C4 chain hydrocarbon group, a C3-C6 alicyclic hydrocarbon group or a 5-6 membered aromatic heterocyclic group {the 5-6 membered aromatic heterocyclic group may be selected from Group V 1 substituted with one or more substituents in}, X d represents a chlorine atom or a bromine atom, X 1d The combination of and nd means: X 1d is a combination of CH, nd is 0, 1 or 2; or, X 1d is a nitrogen atom, nd is a combination of 1 or 2, Group V 1 : A group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group {the C1-C4 alkyl group and the C1-C4 alkoxy group may be substituted by one or more halogen atoms} and a halogen atom; in, The compound represented by formula (V) does not include: 3-Chloro-5-(ethylthio)pyridine, 3-Bromo-5-(ethylthio)pyridine, 3-Chloro-5-(ethylsulfonyl)pyridine, 3-bromo-5-(ethylsulfonyl)pyridine, 3-Chloro-5-(propylthio)pyridine, 3-chloro-5-[(1-methylethyl)thio]pyridine, 3-bromo-5-[(1-methylethyl)thio]pyridine, 3-chloro-5-[(1-methylethyl)sulfonyl]pyridine, 3-bromo-5-[(1-methylethyl)sulfonyl]pyridine, 3-Chloro-5-[(1,1-dimethylethyl)thio]pyridine, 3-Bromo-5-[(1,1-dimethylethyl)thio]pyridine, 3-Chloro-5-[(1,1-dimethylethyl)sulfonyl]pyridine, 3-bromo-5-[(1,1-dimethylethyl)sulfonyl]pyridine, 3-Chloro-5-(cyclohexylsulfonyl)pyridine, 3-Bromo-5-(cyclopropylthio)pyridine, 3-bromo-5-(cyclopropylsulfonyl)pyridine, 5-[(5-bromo-3-pyridyl)thio]-2-methylpyridine, 5-[(5-bromo-3-pyridyl)sulfonyl]-2-methylpyridine, and 3,3'-Sulfonylbis(5-bromopyridine).

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