Condensed ring compound and noxious arthropod control composition containing same

Abstract

The present invention provides a compound having an excellent controlling efficacy against harmful arthropods. (In the formula, L represents a single bond or the like, R1 represents a C1-C6 chain hydrocarbon group or the like, R2 represents a 5-or 6-membered aromatic heterocyclic group or the like, X represents NR11C (Z) R12 or the like, Z represents an oxygen atom or the like, R11 represents a C1-C6 chain hydrocarbon group or the like, R12 represents a phenyl group or the like which may be substituted with one or more substituents, and n represents a hydrogen atom or the like. Q represents a group represented by formula A1 (wherein # represents a bonding site to R2, and represents a bonding site to a carbon atom), or the like), or an N-oxide thereof, has an excellent controlling effect on harmful arthropods.

Description

Technical Field

[0001] This patent application claims priority and interest under the Paris Convention based on Japanese Patent Application No. 2023-176517 (filed on October 12, 2023), the entire contents of which are incorporated herein by reference.

[0002] This invention relates to fused-ring compounds and compositions for controlling harmful arthropods containing such fused-ring compounds. Background Technology

[0003] To date, various compounds have been studied for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes a compound that has pest control effects.

[0004] Existing technical documents Patent documents Patent Document 1: International Publication No. 2022 / 233777 Summary of the Invention

[0005] The problem that the invention aims to solve The purpose of this invention is to provide compounds that have excellent control efficacy against harmful arthropods.

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

[0007] The present invention is described below.

[0008] [1] [1] The compound shown in formula (I) (hereinafter referred to as compound N of the present invention) or its N oxide (hereinafter referred to as compound N of the present invention or its N oxide) [Chemical Formula 1] In the formula, L indicates a single bond or - (CR) 4a R 4b ) n -, R 4a and R 4b The same or different from each other indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group, a cyano group, a hydroxyl group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms. n represents 1, 2, 3, 4, 5, or 6. R1 This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from the group consisting of cyclopropyl and halogen atoms; a C3-C6 cycloalkyl group that can be substituted by one or more halogen atoms; or a C1-C6 alkoxy, cyano, halogen atom, hydroxyl, or hydrogen atom that can be substituted by one or more halogen atoms. Q represents the group shown in formula A1, formula A2, formula A3, formula A4, formula A5, or formula A6 (# indicates a group with R). 2 The bonding sites (● indicates the bonding sites with carbon atoms). [Chemical Formula 2] Q 1 Q 2 and Q 3 Combinatorial representation: Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 The combination; Q 1 For nitrogen atoms, Q 2 For CR 3q2 Q 3 For CR 3q3 The combination; Q 1 For CR 3q1 Q 2 For nitrogen atoms, Q 3 For CR 3q3 Combinations; or Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 A combination of nitrogen atoms, Q 1a and Q 2a Combinatorial representation: Q 1a For CR 3q4 Q 2a For CR 3q5 The combination; Q 1a For nitrogen atoms, Q 2a For CR 3q5 Combinations; or Q 1a For CR 3q4 Q 2a A combination of nitrogen atoms, R3q1 R 3q2 R 3q3 R 3q4 R 3q5 and R 4 "Same or different from each other" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or NR. 6 C(O)R 5 NR 6 C(O)OR 5 NR 6 C(O)NR 5 R 12 C(O)NR 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), N=S(O) p R 28 R 15 cyano, halogen, or hydrogen atoms Z 1 Represents oxygen or sulfur atoms. p represents 0 or 1. R 5 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 6 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 7 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 9This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 12 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 15 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, or a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B. R 2 This indicates a phenyl group that can be substituted by one or more substituents selected from group A, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A, or a C(O)NR group. 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), C(O)R 5 NR 16 C(O)R 17 NR 16 C(O)OR 17 NR 16 C(O)NR 17 R 18 S(O)2NR 16 R 17 OR 18 S(O) m R 15 , thiol, group shown in formula E1, group shown in formula E2, or group shown in formula E3 (# 2 (This indicates the bonding site with the group shown in Formula A1, Formula A2, Formula A3, Formula A4, Formula A5, or Formula A6). [Chemical Formula 3] m represents 0, 1, or 2. R 16 R 17 and R 18"Same" or "different from each other" refers to a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered heterocyclic group that can be substituted by one or more substituents selected from group B, a C1-C6 alkyl group that can be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 2 For NR 16 C(O)R 17 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom and R 17 The bonded carbon atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be replaced by one or more halogen atoms}. R 2 For NR 16 C(O)OR 17 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 The bonded oxygen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}. R 2 For NR 16 C(O)NR 17 R 18 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 The bonded nitrogen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}. Q 5 Indicates CR E11 R 27 NR E12 oxygen or sulfur atoms Q 4 Indicates CR E13 Or nitrogen atoms, Q 6 Indicates CR E14 Or nitrogen atoms, Q 7 Indicates CR E15 Or nitrogen atoms, Q 8 Indicates CR E16Or nitrogen atoms, Q 9 Indicates CR E17 Or nitrogen atom (wherein, the group represented by formula E2 does not include Q) 6 and Q 7 In the case of nitrogen atoms, Q 6 Q 8 and Q 9 The case where both are nitrogen atoms, and Q 7 Q 8 and Q 9 (The case where both are nitrogen atoms) Q 10 Indicates CR E18 Or nitrogen atoms, R E11 and R E31 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, or a C(O)NR group. 7 R 8 NR 9 C(O)R 5 A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 8 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R E12 and R E32 "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 27 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group B, consisting of halogen atoms and cyano groups, or a phenyl or hydrogen atom that can be substituted by one or more substituents selected from group B. R E13 R E14 R E15 R E16 R E17 and R E18 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, or a C(O)NR group. 7 R 8 NR 9 C(O)R 5A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. X represents NR 10 C(Z)R 11 NR 10 C(O)OR 11 NR 10 C(Z)NR 11 R 12 NR 10 C (=NOR) 9 R 11 NR 10 C (=NOR) 9 (NR) 11 R 12 N=C (OR) 9 R 11 N=C(SR) 15 R 11 N=C(NR) 6 R 7 R 11 NR 10 X 1 Or N=S(O) p R 11 R 28 , Z represents an oxygen atom or a sulfur atom. X 1 This indicates a 9- or 10-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A. R 10 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, a C1-C6 alkylsulfonyl group that can be substituted by one or more halogen atoms, OR 14 C(O)R 13 C(O)OR 13 C (=NR) 7 R 13 C(O)NR 6 R 7 Or hydrogen atoms, R 11 This indicates a phenyl group that can be substituted by one or more substituents selected from group A, or a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A. R 13This indicates a C1-C6 chain hydrocarbon group or phenyl group that can be substituted with one or more halogen atoms {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C6 alkoxy groups that can be substituted with one or more halogen atoms, C1-C6 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups or hydrogen atoms that can be substituted with one or more halogen atoms, R 14 This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a phenylmethyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more halogen atoms, or a hydrogen atom. R 28 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, or a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E. Group A: A C1-C6 chain hydrocarbon group {which may be substituted by one or more substituents selected from the group consisting of: C3-C6 cycloalkyl, cyano, and halogen atoms that may be substituted by one or more halogen atoms}, C3-C6 cycloalkyl {which may be substituted by one or more substituents selected from the group consisting of C1-C6 alkoxy, cyano, and halogen atoms}, a phenyl group that may be substituted by one or more substituents selected from Group B, a 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from Group B, OR 3a SF5, NR 3d OR 3b NR 3b C(O)R 3c NR 3d NR 3b C(O)R 3c NR 3b C(O)OR 3e NR 3d NR 3b C(O)OR 3e NR 3b C(O)NR 3f R 3g NR 3d NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i C(O)R 3c C(O)OR 3j C(O)NR 3f R3g S(O)2NR 3f R 3g NR 3b C (=NOR) 3j R 3d NR 3b S(O)2R 3k S(O) m R 3k It is a group composed of cyano, nitro and halogen atoms.

[0009] R 3a The following groups represent C3-C6 cycloalkyl groups that can be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms; phenyl groups that can be substituted with one or more substituents selected from group B; 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more substituents selected from group B; and C(O)R groups. 3c C(O)OR 3j C(O)NR 3f R 3g S(O)2R 3k Or hydrogen atoms, R 3b This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3c This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B, or a hydrogen atom. R 3d This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3e This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a (C1-C3 alkyl)phenyl group {the phenyl portion of the (C1-C3 alkyl)phenyl group can be substituted with one or more substituents selected from group B}. R 3f This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3g This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, or a hydrogen atom. R 3hThis indicates a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B, or a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms. R 3i This refers to C1-C6 alkyl groups that can be substituted with one or more halogen atoms, or C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms. R 3j This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenyl group that can be substituted by one or more substituents selected from group B, or a hydrogen atom. R 3k It represents a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, or a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms.

[0010] Group B: A group consisting of C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted by one or more halogen atoms, C1-C6 alkoxy groups, cyano groups, hydroxyl groups and halogen atoms that can be substituted by one or more halogen atoms.

[0011] Group C: C3-C6 cycloalkyl groups substituted with one or more substituents selected from Group E; phenyl groups substituted with one or more substituents selected from Group B; 5- or 6-membered aromatic heterocyclic groups substituted with one or more substituents selected from Group B; OR 3a NR 3d OR 3b NR 3b C(O)R 3c NR 3d NR 3b C(O)R 3c NR 3b C(O)OR 3e NR 3d NR 3b C(O)OR 3e NR 3b C(O)NR 3f R 3g NR 3d NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i C(O)R 3c C(O)OR 3j C(O)NR 3f R3g S(O) m R 3k It is a group composed of cyano, nitro and halogen atoms.

[0012] Group E: Composed of C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, OR 3a S(O) m R 3k It is a group composed of oxo groups, cyano groups, and halogen atoms.

[0013] Group F: C3-C6 cycloalkyl groups substituted with one or more substituents selected from Group E; phenyl groups substituted with one or more substituents selected from Group B; 5- or 6-membered aromatic heterocyclic groups substituted with one or more substituents selected from Group B; OR 3a S(O) m R 3k C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g NR 3b R 3c NR 3b C(O)R 3c NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i A group consisting of 3-6 membered non-aromatic heterocyclic groups, cyano groups, and halogen atoms. [2] The compound or its N oxide as described in [1], wherein R 3a C3-C6 cycloalkyl groups that can be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms; phenyl groups that can be substituted with one or more substituents selected from group B; 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more substituents selected from group B; C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g Or hydrogen atoms.

[0014] [3] The compound or its N oxide as described in [1] or [2], wherein, in formula (I), L represents a single bond. R 1 It is methyl. Q is a group represented by formula A1, formula A2, or formula A3. Q1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 , R 3q1 R 3q2 and R 3q3 They may be the same or different from each other, consisting of methyl, halogen, or hydrogen atoms. Q 1a and Q 2a The combination is: Q 1a For CR 3q4 Q 2a For CR 3q5 The combination; Q 1a For nitrogen atoms, Q 2a For CR 3q5 Combinations; or Q 1a For CR 3q4 Q 2a A combination of nitrogen atoms, R 3q4 R 3q5 and R 4 They may be the same or different from each other, consisting of methyl, halogen, or hydrogen atoms. R 2 The phenyl, pyrazolyl, thiazolyl, oxadiazolyl, pyridyl, and pyrimidinyl groups {the phenyl, pyrazolyl, thiazolyl, oxadiazolyl, pyridyl, and pyrimidinyl groups may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted by one or more halogen atoms, C1-C3 alkoxy groups substituted by one or more halogen atoms, cyano groups, and halogen atoms}, C(O)NR 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), C(O)R 5 Or S(O) m R 15 , R 5 It is a C1-C3 alkyl group. R 6 It is a methyl or hydrogen atom. R 7 It is a C1-C3 alkyl group or a hydrogen atom. R 9 It is a C1-C3 alkyl group or a hydrogen atom. R15 It is a C1-C3 alkyl group. m is 0, 1, or 2. X is NR 10 C(Z)R 11 or NR 10 C(Z)NR 11 R 12 , Z stands for oxygen atom. R 10 It is a methyl or hydrogen atom. R 11 The phenyl, pyrazolyl, or pyridyl group can be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl that can be substituted by a cyano, and a halogen atom. R 12 It is a hydrogen atom.

[0015] [4] The compound or its N oxide as described in any one of [1] to [3], wherein, in formula (I), L represents a single bond. R 1 It is methyl. Q is a group represented by formula A1 or a group represented by formula A2. Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 , R 3q1 R 3q2 and R 3q3 It is a hydrogen atom. R 2 It is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl groups may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups, cyano groups, and halogen atoms that may be substituted by one or more halogen atoms}, X is NR 10 C(Z)R 11 or NR 10 C(Z)NR 11 R 12 , Z stands for oxygen atom. R 10 It is a methyl or hydrogen atom. R 11The phenyl, pyrazolyl, or pyridyl group can be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl that can be substituted by a cyano, and a halogen atom. R 12 It is a hydrogen atom.

[0016] [5] A composition for controlling harmful arthropods, comprising an inactive carrier and any one of [1] to [4] or its N oxide.

[0017] [6] A composition comprising one or more components selected from the groups (a), (b), (c) and (d), and a compound or its N oxide as described in any one of [1] to [4]: Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients; Group (b): Bactericidal active ingredients; Group (c): Plant growth regulators; Group (d): Repellent component.

[0018] [7] A method for controlling harmful arthropods, wherein an effective amount of any one of [1] to [4] or its N oxide or an effective amount of the composition of claim 6 is applied to the harmful arthropod or its habitat.

[0019] [8] A seed or vegetative reproductive organ that retains an effective amount of any one of [1] to [4] or its N oxide or an effective amount of the composition of claim 6.

[0020] Invention Effects This invention enables the prevention and control of harmful arthropods. Detailed Implementation

[0021] The substituents in this invention will be explained.

[0022] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms.

[0023] When the substituent has two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0024] 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.

[0025] The term "chain hydrocarbon group" refers to alkyl, alkenyl, or alkynyl groups.

[0026] Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, butyl, sec-butyl, tert-butyl, pentyl, and hexyl.

[0027] Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl.

[0028] Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl.

[0029] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, and hexyloxy.

[0030] Examples of 5- or 6-membered aromatic heterocyclic groups include pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, and pyrazinyl.

[0031] Examples of 9-membered aromatic heterocyclic groups include benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, and triazolopyridyl. Examples of 10-membered aromatic heterocyclic groups include quinolinyl, isoquinolinyl, quinazolinyl, and quinazolinone.

[0032] The term "(C3-C6 cycloalkyl)C1-C3 alkyl" refers to a group that can be substituted with one or more halogen atoms. Examples of such groups include cyclopropylmethyl, cyclopropylethyl, (2,2-difluorocyclopropyl)methyl, 2-cyclopropyl-1,1,2,2-tetrafluoroethyl, and 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl.

[0033] The term "phenyl C1-C3 alkyl" refers to a phenyl moiety that can be substituted by one or more substituents selected from group B, such as benzyl, 2-fluorobenzyl, 4-chlorobenzyl, 4-(trifluoromethyl)benzyl, and 2-[4-(trifluoromethyl)phenyl]ethyl.

[0034] Examples of 3- to 6-membered non-aromatic heterocyclic groups include oxobutyranyl, pyrrolyl, 2-oxopyrrolyl, 2-oxopymidazolidinyl, 3,4,5,6-tetrahydro-2-pyrimidinyl, tetrahydrofuranyl, piperidinyl, tetrahydropyranyl, isoxazolidinyl, and morpholinyl.

[0035] Examples of alkyl sulfonyl groups include methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, and isopropyl sulfonyl.

[0036] Examples of cycloalkylsulfonyl groups include cyclopropylsulfonyl, cyclobutylsulfonyl, and cyclohexylsulfonyl.

[0037] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0038] The compounds of the present invention sometimes contain more than one stereoisomer. Examples of stereoisomers include enantiomers, diastereomers, and geometric isomers. The compounds of the present invention include each stereoisomer and mixtures of stereoisomers in any ratio.

[0039] The N oxide of the compound shown in formula (I) refers to the structure obtained by substituting at least one nitrogen atom in the compound shown in formula (I) with an oxo group.

[0040] Compound N of the present invention sometimes forms an acid addition salt. Examples of acids that can form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. Acid addition salts can be obtained, for example, by mixing compound N of the present invention with an acid.

[0041] Examples of compounds N in this invention include the following compounds.

[0042] [Method 1] In compound N of the present invention, Q is a group represented by formula A1-1, formula A1-2, formula A2-1, formula A2-2, formula A2-3, formula A3-1, formula A3-2, formula A4-1, formula A4-2, or formula A5-1 (# indicates a group related to R). 2 The bonding site (● indicates the bonding site with a carbon atom), R 3q1 R 3q2 R 3q3 R 3q4 R 3q5 and R 4The same or different from each other are compounds of C1-C3 chain hydrocarbon groups that can be substituted with one or more halogen atoms, phenyl groups that can be substituted with one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more substituents selected from group B, and cyclopropyl, cyano, halogen or hydrogen atoms that can be substituted with one or more substituents selected from group E.

[0043] [Chemical Formula 4] [Method 2] In compound N of the present invention, Q is a group represented by formula A1-1, formula A1-2, formula A2-1, formula A2-2, formula A2-3, formula A3-1, or formula A3-2 (# indicates a group related to R). 2 The bonding site (● indicates the bonding site with a carbon atom), R 3q1 R 3q2 R 3q3 R 3q4 R 3q5 and R 4 They are either identical or different from each other, and are C1-C3 chain hydrocarbon groups that can be substituted by one or more halogen atoms, or cyclopropyl, cyano, halogen or hydrogen atoms that can be substituted by one or more substituents selected from group E.

[0044] [Method 3] In compound N of the present invention, Q is a group represented by formula A1-1, a group represented by formula A2-1, a group represented by formula A3-1, or a group represented by formula A3-2 (# indicates a group related to R). 2 The bonding site (● indicates the bonding site with a carbon atom), R 3q1 R 3q2 R 3q3 R 3q4 R 3q5 and R 4 They are either identical or different from each other, and are C1-C3 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be replaced by one or more halogen atoms.

[0045] [Method 4] In the compound N of the present invention, L is a single bond or -(CR) 4a R 4b ) n -, R 4a and R 4b They are either identical or different from each other, and are C1-C3 chain hydrocarbon groups that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0046] [Method 5] In the compound N of the present invention, L is a single bond.

[0047] [Method 6] In Method 1, L is a single bond or - (CR4a R 4b ) n -, R 4a and R 4b Compounds that are the same or different from each other, and are C1-C3 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms, where n is 1, 2 or 3.

[0048] [Method 7] In Method 2, L is a single bond or - (CR 4a R 4b ) n -, R 4a and R 4b Compounds that are the same or different from each other, and are C1-C3 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms, where n is 1, 2 or 3.

[0049] [Method 8] In Method 3, L is a single bond or - (CR 4a R 4b ) n -, R 4a and R 4b Compounds that are the same or different from each other, and are C1-C3 chain hydrocarbon groups or hydrogen atoms that can be replaced by one or more halogen atoms, where n is 1, 2 or 3.

[0050] [Method 9] In Method 1, L is a compound with a single bond.

[0051] [Method 10] In Method 2, L is a compound with a single bond.

[0052] [Method 11] In Method 3, L is a compound with a single bond.

[0053] [Method 12] In compound N of the present invention, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0054] [Method 13] In compound N of the present invention, R 1 Compounds containing methyl groups.

[0055] [Method 14] In Method 1, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0056] [Method 15] In Method 2, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0057] [Method 16] In Method 3, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0058] [Method 17] In Method 4, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0059] [Method 18] In Method 5, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0060] [Method 19] In Method 6, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0061] [Method 20] In Method 7, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0062] [Method 21] In Method 8, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0063] [Method 22] In Method 9, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0064] [Method 23] In Method 10, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0065] [Method 24] In Method 11, R 1 It is a compound consisting of a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms.

[0066] [Method 25] In Method 1, R 1 Compounds containing methyl groups.

[0067] [Method 26] In Method 2, R 1 Compounds containing methyl groups.

[0068] [Method 27] In Method 3, R 1 Compounds containing methyl groups.

[0069] [Method 28] In Method 4, R 1 Compounds containing methyl groups.

[0070] [Method 29] In Method 5, R 1 Compounds containing methyl groups.

[0071] [Method 30] In Method 6, R 1 Compounds containing methyl groups.

[0072] [Method 31] In Method 7, R 1 Compounds containing methyl groups.

[0073] [Method 32] In Method 8, R 1 Compounds containing methyl groups.

[0074] [Method 33] In Method 9, R 1 Compounds containing methyl groups.

[0075] [Method 34] In Method 10, R 1 Compounds containing methyl groups.

[0076] [Method 35] In Method 11, R 1 Compounds containing methyl groups.

[0077] [Method 36] In compound N of the present invention, Q is a group represented by formula A1, Q 1 Q 2 and Q 3 For CH, R 1 A compound in which one or more substituents selected from the group consisting of cyclopropyl and halogen atoms are C1-C6 alkyl groups, and L is a single bond.

[0078] [Method 37] In any of Methods 1 to 36 or Compound N of the present invention, R 2 The phenyl group is a 5- or 6-membered aromatic heterocyclic group. The phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl groups substituted by one or more substituents selected from the group consisting of cyano groups and halogen atoms; C1-C3 chain hydrocarbon groups substituted by one or more halogen atoms; OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, C(O)NR 6 R 7 NR 16 C(O)R 17 NR 16 C(O)OR 17 NR 16 C(O)NR 17 R 18 OR 18The group shown in formula E1-1, the group shown in formula E1-2, the group shown in formula E2-1, the group shown in formula E2-2, the group shown in formula E3-1, or the group shown in formula E3-2 (# 2 (This indicates the bonding site with the group shown in Formula A1, Formula A2, Formula A3, Formula A4, Formula A5, or Formula A6). [Chemical Formula 5] R 18 R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more substituents selected from group E, or a hydrogen atom. 2 For NR 16 C(O)R 17 R 16 and R 17 With R 16 The bonded nitrogen atom and R 17 When the bonded carbon atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}, R 2 The group is represented by formula E4-1, formula E4-2, formula E4-3, formula E4-4, or formula E4-5. [Chemical Formula 6] R 2 For NR 16 C(O)OR 17 R 16 and R 17 With R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 When the bonded oxygen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}, R 2 The group is the group shown in formula E5-1, formula E5-2, formula E5-3, formula E5-4, formula E5-5, formula E5-6, or formula E5-7. [Chemical Formula 7] R 2 For NR 16 C(O)NR 17 R 18 R 16 and R17 With R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 When the bonded nitrogen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}, R 2 The group is the group shown in formula E6-1, the group shown in formula E6-2, the group shown in formula E6-3, or the group shown in formula E6-4. [Chemical Formula 8] R E31 R is a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms. E12 and R E32 The same or different from each other, is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a cyclopropyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom, R E13 R E14 R E15 R E16 R E17 and R E18 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group C, C1-C6 alkoxy groups that can be substituted by one or more halogen atoms, and C(O)NR. 7 R 8 NR 9 C(O)R 5 A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E; R 8 A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be substituted by one or more substituents selected from group C.

[0079] [Method 38] In any of Methods 1 to 36 or Compound N of the present invention, R 2 The group is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl group substituted by one or more substituents selected from the group consisting of cyano and halogen atoms; C1-C3 chain hydrocarbon group substituted by one or more halogen atoms; C1-C3 alkoxy group substituted by one or more halogen atoms; NR group substituted by one or more halogen atoms; ... 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k, cyano group and halogen atom}, C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 The groups shown in Formula E1-1, Formula E1-2, Formula E2-1, Formula E2-2, Formula E4-1, Formula E5-1, Formula E5-3, or Formula E6-1 (#) 2 (Indicates the bonding site with a carbon atom), R E12 R is a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, a cyclopropyl group that can be substituted by one or more halogen atoms, or a hydrogen atom. E13 R E14 R E15 R E16 and R E17 The same or different from each other are C1-C3 chain hydrocarbon groups that can be substituted by one or more halogen atoms, C1-C3 alkoxy groups that can be substituted by one or more halogen atoms, and C(O)NR. 7 R 8 NR 9 C(O)R 5 Compounds consisting of cyclopropyl, cyano, halogen, or hydrogen atoms that can be substituted by one or more halogen atoms.

[0080] [Method 39] In any of Methods 1 to 36 or Compound N of the present invention, R 2 The group is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl group substituted by one or more substituents selected from the group consisting of cyano and halogen atoms; C1-C3 chain hydrocarbon group substituted by one or more halogen atoms; C1-C3 alkoxy group substituted by one or more halogen atoms; NR group substituted by one or more halogen atoms; ... 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), the group shown in formula E1-1, or the group shown in formula E1-2 (# 2 Compounds that indicate the bonding sites with carbon atoms.

[0081] [Method 40] In any of Methods 1 to 36 or Compound N of the present invention, R 2 The group is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted by one or more halogen atoms, NR} 3b C(O)R 3c C(O)NR 3f R 3g Compounds containing cyano groups and halogen atoms.

[0082] [Method 41] In any of Methods 1 to 36 or Compound N of the present invention, R 2 The phenyl group is a 5- or 6-membered aromatic heterocyclic group. The phenyl group and the 5- or 6-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl groups substituted by one or more substituents selected from the group consisting of cyano groups and halogen atoms; C1-C3 chain hydrocarbon groups substituted by one or more halogen atoms; OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, C(O)NR 6 R 7 NR 16 C(O)R 17 OR 18 The groups shown in Formula E1-1, Formula E1-2, Formula E2-1, Formula E2-2, Formula E3-1, Formula E3-2, Formula E4-1, Formula E4-2, Formula E4-3, Formula E4-4, Formula E4-5, Formula E5-1, Formula E5-2, Formula E5-3, Formula E5-4, Formula E5-5, Formula E5-6, Formula E5-7, Formula E6-1, Formula E6-2, Formula E6-3, or Formula E6-4 (#) 2 (Indicates the bonding site with a carbon atom), R 18 R is a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more substituents selected from group E, or a hydrogen atom. E31 R is a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms. E12 and RE32 The same or different from each other, is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a cyclopropyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom, R 27 R is a C1-C6 chain hydrocarbon group or hydrogen atom that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups. E13 R E14 R E15 R E16 R E17 and R E18 The same or different from each other are C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group C, C1-C6 alkoxy groups that can be substituted by one or more halogen atoms, and C(O)NR. 7 R 8 NR 9 C(O)R 5 A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E; R 8 A compound consisting of a C1-C6 chain hydrocarbon group or a hydrogen atom that can be substituted by one or more substituents selected from group C.

[0083] [Method 42] In any of Methods 1 to 36 or Compound N of the present invention, X is NR. 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1 It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3f R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0084] [Method 43] In Method 37, X is NR 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1 It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O)m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}, cyclopropyl groups that may be substituted with cyano, OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl moiety in the phenylmethyl group can be replaced by one or more halogen atoms} or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3f R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0085] [Method 44] In Method 38, X is NR 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}, cyclopropyl groups that may be substituted with cyano, OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3f R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0086] [Method 45] In Method 39, X is NR 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1 It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}, cyclopropyl groups that may be substituted with cyano, OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl moiety in the phenylmethyl group can be replaced by one or more halogen atoms} or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3fR is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0087] [Method 46] In Method 40, X is NR 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1 It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}, cyclopropyl groups that may be substituted with cyano, OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms.3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3f R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0088] [Method 47] In Method 41, X is NR 10 C(O)R 11 NR 10 C(O)NR 11 R 12 , or NR 10 X 1 X 1 It is a 9- or 10-membered aromatic heterocyclic group {the 9- or 10-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3a NR 3b C(O)R 3c C(O)NR 3f R 3g S(O) m R 3k , cyano group and halogen atom}, R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}, cyclopropyl groups that may be substituted with cyano, OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3b R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3c R is a C1-C3 alkyl, cyclopropyl, phenyl, pyridyl, or pyrazolyl group that can be substituted by one or more halogen atoms {where the phenyl, pyridyl, or pyrazolyl group can be substituted by one or more halogen atoms}. 3f R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3g R is a C1-C3 alkyl or cyclopropyl group that can be substituted with one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0089] [Method 48] In methods 1 to 36 or in compound N of the present invention, X is NR. 10 C(O)R 11 , or NR 10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3kIt is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0090] [Method 49] In Method 37, X is NR 10 C(O)R 11 , or NR 10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0091] [Method 50] In Method 38, X is NR 10 C(O)R 11 , or NR 10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3aS(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0092] [Method 51] In Method 39, X is NR 10 C(O)R 11 , or NR 10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0093] [Method 52] In Method 40, X is NR 10 C(O)R 11 , or NR10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0094] [Method 53] In Method 41, X is NR 10 C(O)R 11 , or NR 10 C(O)NR 11 R 12 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted with a substituent selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted with one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 12 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 13R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0095] [Method 54] In any of Methods 1 to 36 or Compound N of the present invention, X is NR. 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0096] [Method 55] In Method 37, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0097] [Method 56] In Method 38, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0098] [Method 57] In Method 39, X is NR 10 C(O)R 11 R 10C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0099] [Method 58] In Method 40, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0100] [Method 59] In Method 41, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0101] [Method 60] In any of Methods 1 to 36 or Compound N of the present invention, X is NR. 10 C(O)R 11 R 10 For hydrogen atoms, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0102] [Method 61] In Method 37, X is NR 10 C(O)R 11 R 10 For hydrogen atoms, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0103] [Method 62] In Method 38, X is NR 10 C(O)R 11 R 10 For hydrogen atoms, R 11The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0104] [Method 63] In Method 39, X is NR 10 C(O)R 11 R 10 For hydrogen atoms, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0105] [Method 64] In Method 40, X is NR 10 C(O)R 11 R 10 For hydrogen atoms, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0106] [Method 65] In Method 41, X is NR 10 C(O)R 11 R 10 For hydrogen atoms, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, and halogen atoms}.

[0107] [Method 66] In any of Methods 1 to 36 or Compound N of the present invention, R 2 X is a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A, where X is NR. 11 C(O)R 12 R 11 R is a C1-C6 alkyl group that can be substituted by one or more substituents selected from group F. 12 A compound of a phenyl group that can be substituted by one or more substituents selected from group A.

[0108] [Method A1] In compound N of the present invention, Q is a group represented by formula A3-3 (# indicates a group related to R). 2 The bonding site (● indicates the bonding site with a carbon atom), R 3q5 and R 4 They are either identical or different from each other, and are C1-C3 chain hydrocarbon groups, halogen atoms or hydrogen atoms that can be replaced by one or more halogen atoms.

[0109] [Chemical Formula 9] [Method A2] In Method A1, L is a compound with a single bond.

[0110] [Method A3] In Method A1, R 1 Compounds containing methyl groups.

[0111] [Method A4] In Method A2, R 1 Compounds containing methyl groups.

[0112] [Method A5] In Method A4, R 2 The group is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted by one or more halogen atoms, NR} 3b C(O)R 3c C(O)NR 3f R 3g Compounds containing cyano groups and halogen atoms.

[0113] [Method A6] In Method A4, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0114] [Method A7] In Method A4, X is NR 10 C(O)R 11 R 10It is a C1-C3 alkyl group or a hydrogen atom, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, C1-C3 alkoxy groups substituted with one or more halogen atoms, cyano groups and halogen atoms}.

[0115] [Method A8] In Method A5, X is NR 10 C(O)R 11 R 10 C1-C3 alkyl, OR 14 C(O)R 13 C(O)OR 13 Or hydrogen atom, R 11 The group is phenyl, pyridyl, or pyrazolyl {the phenyl, pyridyl, or pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, which may be substituted with a cyano group; C1-C3 alkyl {the C1-C3 alkyl group may be substituted by one or more substituents selected from the group consisting of cyclopropyl, cyano, and halogen atoms}; OR 3a S(O) m R 3k , cyano group and halogen atom}, R 13 R is a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 14 R is a C1-C3 alkyl group, phenylmethyl group {the phenyl portion of the phenylmethyl group can be replaced by one or more halogen atoms}, or a hydrogen atom that can be substituted with one or more halogen atoms. 3a R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 3k It is a C1-C3 alkyl or cyclopropyl compound that can be substituted with one or more halogen atoms.

[0116] [Method A9] In Method A5, X is NR 10 C(O)R 11 R 10 It is a C1-C3 alkyl group or a hydrogen atom, R 11 The compound is a phenyl group {which may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted with one or more halogen atoms, C1-C3 alkoxy groups substituted with one or more halogen atoms, cyano groups and halogen atoms}.

[0117] Next, the method for manufacturing the compound of the present invention will be described.

[0118] Manufacturing Method 1 The compound shown in formula (I-1) (hereinafter referred to as compound (I-1)) can be produced by reacting the compound shown in formula (I-2) (hereinafter referred to as compound (I-2)) with the compound shown in formula (I-3) (hereinafter referred to as compound (I-3)).

[0119] [Chemical Formula 10] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents include ethers such as tetrahydrofuran (THF), 1,4-dioxane, 1,2-dimethoxyethane, methyl tert-butyl ether, and diethyl ether; halogenated hydrocarbons such as dichloromethane and chloroform; nitriles such as acetonitrile; aromatic hydrocarbons such as toluene and xylene; aprotic polar solvents such as N-methylpyrrolidone (NMP) and N,N-dimethylformamide (DMF), and mixtures thereof.

[0120] In the reaction, a base may be used as needed. Examples of bases include organic bases such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases); and alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate (hereinafter referred to as alkali metal carbonates).

[0121] In the reaction, compound (I-3) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-2).

[0122] The reaction temperature is typically in the range of 0℃ to 200℃. The reaction time is typically in the range of 0.1 to 48 hours.

[0123] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-1).

[0124] Compound (I-3) is a commercially available compound or can be manufactured using known methods.

[0125] Manufacturing Method 2 The compound shown in formula (I) (i.e., compound N of the present invention) can be produced by reacting the compound shown in formula (I-8) (hereinafter referred to as compound (I-8)) with the compound shown in formula (IM) (hereinafter referred to as compound (IM)).

[0126] [Chemical Formula 11] [In the formula, X] a M represents a chlorine atom, a bromine atom, or an iodine atom. A [The symbols represent 9-boronbicyclo[3.3.1]nonane-9-yl, dihydroxyboronyl, 4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl, or tributyltinyl; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents include ethers; aromatic hydrocarbons; aprotic polar solvents; water and mixtures of two or more of them.

[0127] Examples of metal catalysts include palladium catalysts such as tetra(triphenylphosphine)palladium (0), 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride (II), tris(dibenzylacetone)palladium (0), and palladium acetate (II); nickel catalysts such as bis(cyclooctadiene)nickel (0) and nickel chloride (II); iron catalysts such as ferric chloride (III) and acetylacetone iron (III); copper catalysts such as copper iodide (I) and copper chloride (I), as well as combinations of two or more of them.

[0128] In the reaction, ligands, bases and / or inorganic halides may also be used as needed.

[0129] 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, and 1,10-phenanthroline.

[0130] Examples of alkalis include alkali metal carbonates and organic alkalis.

[0131] Examples of inorganic halides include alkali metal fluorides such as potassium fluoride and sodium fluoride, and alkali metal chlorides such as lithium chloride and sodium chloride.

[0132] In the reaction, compound (IM) is typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-8), and the metal catalyst is typically used in a ratio of 0.01 to 0.5 moles. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (I-8). When a base is used in the reaction, the base is typically used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (I-8). When an inorganic halide is used in the reaction, the inorganic halide is typically used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (I-8).

[0133] 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.

[0134] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound N of the present invention.

[0135] The compound (IM) is a commercially available compound or can be manufactured using known methods.

[0136] The reaction can also be carried out, for example, according to the method described in Example H2 of International Publication No. 2020 / 070049.

[0137] Manufacturing method 3 The compound shown in formula (I-1A) (hereinafter referred to as compound (I-1A)) can be prepared by reacting the compound shown in formula (I-2A) (hereinafter referred to as compound (I-2A)) with the compound shown in formula (Mg) (hereinafter referred to as compound (Mg)) in the presence of an acid.

[0138] [Chemical Formula 12] [In the formula, X] C [This indicates a leaving group such as a chlorine atom; Boc represents a tert-butyloxycarbonyl group; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents include ethers; haloalkanes; aromatic hydrocarbons; nitriles; aprotic polar solvents; water; and mixtures of two or more of them.

[0139] Examples of acids used in the reaction include trifluoroacetic acid and hydrogen chloride. When using hydrogen chloride, solutions of hydrogen chloride, such as hydrochloric acid or hydrogen chloride / methanol solution, can be supplied to the reaction.

[0140] The reaction can be carried out, for example, by first mixing the compound (I-2A) with an acid, then removing the acid by distillation, and then mixing the compound (Mg).

[0141] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-2A).

[0142] In the reaction, the compound (Mg) is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (I-2A), and the acid is usually used in a ratio of 1 to 100 moles.

[0143] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 24 hours.

[0144] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-1A).

[0145] The compound (Mg) is a commercially available compound or can be manufactured using known methods.

[0146] Manufacturing method 4 Compound (I-1A) can also be prepared by reacting compound (I-2A) with the compound shown in formula (Me) (hereinafter referred to as compound (Me)) in the presence of a condensing agent and an acid.

[0147] [Chemical Formula 13] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents include ethers; halogenated hydrocarbons; aromatic hydrocarbons; nitriles; esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); aprotic polar solvents; nitrogen-containing aromatic compounds such as pyridine, methylpyridine, dimethylpyridine, and quinoline (hereinafter referred to as nitrogen-containing aromatic compounds); and mixtures of two or more of them.

[0148] Examples of acids used in the reaction include trifluoroacetic acid and hydrogen chloride.

[0149] When using hydrogen chloride, solutions of hydrogen chloride, such as hydrochloric acid or hydrogen chloride / methanol solution, can be used for the reaction.

[0150] The reaction can be carried out, for example, by first mixing the compound (I-2A) with an acid, then removing the acid by distillation, and then mixing the compound (Me) with a condensing agent.

[0151] Examples of condensing agents used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0152] A catalyst may be used in the reaction as needed. Examples of catalysts include 1-hydroxybenzotriazole. 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 (I-2A).

[0153] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (I-2A).

[0154] In the reaction, relative to 1 mole of compound (I-2A), compound (Me) is usually used in a ratio of 1 to 2 moles, condensing agent is usually used in a ratio of 1 to 5 moles, and acid is usually used in a ratio of 1 to 100 moles.

[0155] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0156] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-1A).

[0157] The compound (Me) is a commercially available compound or can be manufactured using known methods.

[0158] Manufacturing Method 5 Compound (I-1A) can also be produced by reacting the compound shown in formula (I-11) (hereinafter referred to as compound (I-11)) with compound (I-3).

[0159] [Chemical Formula 14] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-11) instead of compound (I-2) according to manufacturing method 1.

[0160] Manufacturing Method 6 Compound (I-1A) can also be produced by reacting compound (I-11) with compound (Me) in the presence of a condensing agent.

[0161] [Chemical Formula 15] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters; nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of them.

[0162] Examples of condensing agents used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0163] A catalyst may be used in the reaction as needed. Examples of catalysts include 1-hydroxybenzotriazole. 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 (I-11).

[0164] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (I-11).

[0165] In the reaction, the compound (Me) is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (I-11), and the condensing agent is usually used in a ratio of 1 to 5 moles.

[0166] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0167] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-1A).

[0168] Manufacturing method 7 The compound shown in formula (I-1B) (hereinafter referred to as compound (I-1B)) can be produced by reacting the compound shown in formula (I-2B) (hereinafter referred to as compound (I-2B)) with compound (I-3).

[0169] [Chemical Formula 16] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-2B) instead of compound (I-2) according to manufacturing method 1.

[0170] Manufacturing Method 8 Compound (I-1B) can also be produced by reacting compound (I-2B) with compound (Me) in the presence of a condensing agent.

[0171] [Chemical Formula 17] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-2B) instead of compound (I-11) according to manufacturing method 6.

[0172] Manufacturing Method 9 Compound (I-1) can also be produced by reacting the compound shown in formula (I-20) (hereinafter referred to as compound (I-20)) with compound (IM).

[0173] [Chemical Formula 18] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-20) instead of compound (I-8) according to manufacturing method 2.

[0174] Manufacturing Method 10 The compound shown in formula (II-1) (hereinafter referred to as compound (II-1)) can be produced by reacting the compound shown in formula (II-2) (hereinafter referred to as compound (II-2)) with compound (I-3).

[0175] [Chemical Formula 19] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-2) instead of compound (I-2) according to manufacturing method 1.

[0176] Manufacturing method 11 Compound (II-1) can also be produced by reacting compound (II-2) with compound (Me) in the presence of a condensing agent.

[0177] [Chemical Formula 20] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-2) instead of compound (I-11) according to manufacturing method 6.

[0178] Manufacturing method 12 Compound (II-1) can also be produced by reacting the compound of formula (II-19) (hereinafter referred to as compound (II-19)) with compound (IM).

[0179] [Chemical Formula 21] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-19) instead of compound (I-8) according to manufacturing method 2.

[0180] Manufacturing method 13 The compound shown in formula (II-1A) (hereinafter referred to as compound (II-1A)) can be prepared by reacting the compound shown in formula (II-3A) (hereinafter referred to as compound (II-3A)) with compound (I-3) in the presence of an acid.

[0181] [Chemical Formula 22] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out in accordance with manufacturing method 3, using compound (II-3A) instead of compound (I-2A) and compound (I-3) instead of compound (Mg).

[0182] The manufacturing method for the intermediate is described below.

[0183] Reference manufacturing method 1 Compound (I-2) can be produced from the compound shown in formula (I-4) (hereinafter referred to as compound (I-4)).

[0184] [Chemical Formula 23] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Green's PROTECTIVE GROUPS in ORGANIC SYNTHESIS FORTHEDITION P727.

[0185] Compound (I-2) sometimes forms acid addition salts. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.

[0186] Reference manufacturing method 2 Compound (I-4) can be produced by reacting the compound shown in formula (I-5) (hereinafter referred to as compound (I-5)) with compound (IM).

[0187] [Chemical Formula 24] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-5) instead of compound (I-8) according to manufacturing method 2.

[0188] Reference manufacturing method 3 Compound (I-5) can be produced by reacting the compound shown in formula (I-6) (hereinafter referred to as compound (I-6)) with a halogenating agent.

[0189] [Chemical Formula 25] [In the formula, the symbols have the same meaning as in the preceding text.] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include alcohols such as methanol and ethanol (hereinafter referred to as alcohols); nitriles; ethers; aromatic hydrocarbons; aprotic polar solvents; halogenated hydrocarbons; water; and mixtures thereof.

[0190] Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide (hereinafter referred to as NIS).

[0191] In the reaction, a base may be used as needed. Examples of bases include alkali metal carbonates. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-6).

[0192] In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-6).

[0193] 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.

[0194] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-5).

[0195] Reference manufacturing method 4 Compound (I-6) can be produced from the compound shown in formula (I-7) (hereinafter referred to as compound (I-7)).

[0196] [Chemical Formula 26] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Intermediate 23 of International Publication No. 2007 / 147794 and the method described in Example 5 of International Publication No. 2003 / 037900.

[0197] Compound (I-7) is a commercially available compound or can be manufactured using known methods.

[0198] Reference manufacturing method 5 Compound (I-9) can be manufactured from the compound shown in formula (I-7A) (hereinafter referred to as compound (I-7A)) and the compound shown in formula (IA) (hereinafter referred to as compound (IA)).

[0199] [Chemical Formula 27] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Intermediate 23 of International Publication No. 2007 / 147794.

[0200] Reference manufacturing method 6 Compound (I-8) can be produced by reacting compound (I-10) with a halogenating agent.

[0201] [Chemical Formula 28] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-10) instead of compound (I-6) according to reference manufacturing method 3.

[0202] Reference manufacturing method 7 Compound (I-11) can be made from the compound shown in formula (I-2A) (hereinafter referred to as compound (I-2A)).

[0203] [Chemical Formula 29] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Green's PROTECTIVE GROUPS in ORGANIC SYNTHESIS FORTHEDITION P727.

[0204] Compound (I-11) sometimes forms acid addition salts. Examples of acids that can form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.

[0205] Reference manufacturing method 8 Compound (I-2A) can be produced by reacting the compound shown in formula (I-12) (hereinafter referred to as compound (I-12)) with compound (IM).

[0206] [Chemical Formula 30] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-12) instead of compound (I-8) according to manufacturing method 2.

[0207] Reference manufacturing method 9 Compound (I-12) can be produced by reacting the compound shown in formula (I-13) (hereinafter referred to as compound (I-13)) with a halogenating agent.

[0208] [Chemical Formula 31] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-13) instead of compound (I-6) according to reference manufacturing method 3.

[0209] Compound (I-13) is a commercially available compound or can be manufactured using known methods.

[0210] Reference manufacturing method 1-1 Compound (I-2) can also be made from the compound shown in formula (I-4B) (hereinafter referred to as compound (I-4B)).

[0211] [Chemical Formula 32] [In the formula, Cbz represents benzyloxycarbonyl, and other symbols have the same meaning as above.] The reaction can be carried out, for example, according to the method described in Green's PROTECTIVE GROUPS in ORGANIC SYNTHESIS FORTHEDITION P.750.

[0212] Compound (I-2) sometimes forms acid addition salts. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.

[0213] Reference manufacturing method 2-1 Compound (I-4B) can be produced by reacting the compound shown in formula (I-5B) (hereinafter referred to as compound (I-5B)) with compound (IM).

[0214] [Chemical Formula 33] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-5B) instead of compound (I-8) according to manufacturing method 2.

[0215] Refer to manufacturing method 3-1 Compound (I-5B) can be produced by reacting the compound of formula (I-6B) (hereinafter referred to as compound (I-6B)) with a halogenating agent.

[0216] [Chemical Formula 34] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-6B) instead of compound (I-6) according to reference manufacturing method 3.

[0217] Refer to manufacturing method 4-1 Compound (I-6B) can be produced from the compound represented by formula (I-7B) (hereinafter referred to as compound (I-7B)).

[0218] [Chemical Formula 35] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Intermediate 23 of International Publication No. 2007 / 147794, the method described in Example 5 of International Publication No. 2003 / 037900, the method described in Example 1 of International Publication No. 2007 / 134362, the method described in Step 1 of Intermediate BMR of International Publication No. 2021 / 158634, and the method described in Huaxue Xuebao (2005), 63(9), 855-860.

[0219] Refer to manufacturing method 10-1 Compound (I-7B) can be produced from the compound represented by formula (I-14B) (hereinafter referred to as compound (I-14B)).

[0220] [Chemical Formula 36] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Example 1-1, Step 1-1-3 of International Publication No. 2016 / 148145.

[0221] Refer to manufacturing method 10-2 Compound (I-14B) can be produced from the compound shown in formula (I-14A) (hereinafter referred to as compound (I-14A)).

[0222] [Chemical Formula 37] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the method described in Example 25 of the present invention in U.S. Patent Application Publication No. 2002 / 6387938.

[0223] The compound (I-14A) is a commercially available compound or can be manufactured using known methods.

[0224] Reference manufacturing method 11 Compound (I-2B) can be produced by reacting an amine or ammonium salt and a reducing agent with the compound shown in formula (I-15) (hereinafter referred to as compound (I-15)).

[0225] [Chemical Formula 38] [In the formula, the symbols have the same meaning as in the preceding text.] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include alcohols, ethers, aprotic polar solvents, and mixtures thereof.

[0226] Examples of amines include methylamine and ethylamine.

[0227] Examples of ammonium salts include ammonium acetate.

[0228] In the reaction, acids may be used as needed. Examples of acids include organic acids such as acetic acid. When an acid is used in the reaction, it is usually used in a ratio of 0.1 to 10 moles relative to 1 mole of compound (I-15).

[0229] In the reaction, the reducing agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-15).

[0230] 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.

[0231] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-2B).

[0232] Reference manufacturing method 12 Compound (I-15) can be produced by reacting the compound shown in formula (I-16) (hereinafter referred to as compound (I-16)) with the compound shown in formula (Mf) (hereinafter referred to as compound (Mf)).

[0233] [Chemical Formula 39] [In the formula, X] d [This indicates a chlorine atom, bromine atom, or iodine atom; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents include ethers; aromatic hydrocarbons; aprotic polar solvents; and mixtures of two or more of them.

[0234] In the reaction, compound (Mf) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-16).

[0235] 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.

[0236] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-15).

[0237] The compound (Mf) is a commercially available compound or can be manufactured using known methods.

[0238] Reference manufacturing method 13 Compound (I-16) can be produced by reacting the compound shown in formula (I-17) (hereinafter referred to as compound (I-17)) with compound (IM).

[0239] [Chemical Formula 40] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-17) instead of compound (I-8) according to manufacturing method 2.

[0240] Reference manufacturing method 14 Compound (I-17) can be prepared by reacting the compound of formula (I-18) (hereinafter referred to as compound (I-18)) with the compound of formula (Mg) (hereinafter referred to as compound (Mg)) in the presence of a condensing agent.

[0241] [Chemical Formula 41] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters; nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of them.

[0242] Examples of condensing agents used in the reaction include 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate.

[0243] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (I-18).

[0244] In the reaction, the compound (Mg) is usually used in a ratio of 1 to 3 moles relative to 1 mole of the compound (I-18), and the condensing agent is usually used in a ratio of 1 to 5 moles.

[0245] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0246] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-17).

[0247] Reference manufacturing method 15 Compound (I-18) can be prepared by hydrolyzing the compound of formula (I-19) (hereinafter referred to as compound (I-19)) in the presence of a base.

[0248] [Chemical Formula 42] [In the formula, R] X [This indicates C1-C4 alkyl groups; other symbols have the same meaning as above.] The reaction is carried out in the presence of a base, and in the presence of water and an organic solvent. Examples of solvents used in the reaction include ethers, nitriles, alcohols, and mixtures thereof.

[0249] Examples of bases used in reactions include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.

[0250] The reaction time typically ranges from 5 minutes to 72 hours. The reaction temperature typically ranges from 0°C to 100°C.

[0251] Regarding the amount of base used in the reaction, it can generally be used in any proportion from 1 mole to an excess relative to 1 mole of compound (I-19), preferably 1 to 5 moles.

[0252] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-18).

[0253] Compound (I-19) is a commercially available compound or can be manufactured using known methods.

[0254] Reference manufacturing method 16 The compound shown in formula (I-20) (hereinafter referred to as compound (I-20)) can be produced by reacting the compound shown in formula (I-21) (hereinafter referred to as compound (I-21)) with a halogenating agent.

[0255] [Chemical Formula 43] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-21) instead of compound (I-6) according to reference manufacturing method 3.

[0256] Reference manufacturing method 17 Compound (I-21) can be produced by reacting the compound shown in formula (I-22) (hereinafter referred to as compound (I-22)) with compound (I-3).

[0257] [Chemical Formula 44] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-22) instead of compound (I-2) according to manufacturing method 1.

[0258] Reference manufacturing method 18 Compound (I-21) can also be produced by reacting compound (I-22) with compound (Me) in the presence of a condensing agent.

[0259] [Chemical Formula 45] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-22) instead of compound (I-11) according to manufacturing method 6.

[0260] Reference manufacturing method 19 Compound (I-22) can be produced by reacting an amine or ammonium salt and a reducing agent with the compound shown in formula (I-23) (hereinafter referred to as compound (I-23).

[0261] [Chemical Formula 46] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-23) instead of compound (I-15) according to reference manufacturing method 11.

[0262] Reference manufacturing method 20 Compound (I-23) can be produced by reacting the compound shown in formula (I-24) (hereinafter referred to as compound (I-24)) with compound (Mf).

[0263] [Chemical Formula 47] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (I-24) instead of compound (I-16) according to reference manufacturing method 12.

[0264] Reference manufacturing method 21 Compound (I-24) can be prepared by reacting the compound of formula (I-25) (hereinafter referred to as compound (I-25)) with compound (Mg) in the presence of a Lewis acid.

[0265] [Chemical Formula 48] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; haloalkanes; aromatic hydrocarbons; aprotic polar solvents; and mixtures of two or more of them.

[0266] Examples of Lewis acids used in the reaction include trimethylaluminum.

[0267] In the reaction, Lewis acids are typically used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (I-25).

[0268] In the reaction, compound (Mg) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (I-25).

[0269] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0270] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (I-24).

[0271] Compound (I-25) is a commercially available compound or can be manufactured using known methods.

[0272] Reference manufacturing method 22 Compound (II-2) can be produced from the compound shown in formula (II-3) (hereinafter referred to as compound (II-3)).

[0273] [Chemical Formula 49] [In the formula, PG represents tert-butyloxycarbonyl or benzyloxycarbonyl, and other symbols have the same meaning as above.] The reaction can be carried out, for example, according to the methods described in Green's PROTECTIVE GROUPS in ORGANIC SYNTHESIS FORTHEDITION P.727 or P.750.

[0274] Compound (II-2) sometimes forms acid addition salts. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.

[0275] Reference manufacturing method 23 Compound (II-3) can be prepared by reacting the compound shown in formula (II-4) (hereinafter referred to as compound (II-4)) with the compound shown in formula (Mh) (hereinafter referred to as compound (Mh)) in the presence of an acid.

[0276] [Chemical Formula 50] [In the formula, R] v [This indicates C1-C3 alkyl groups; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters; nitriles; aprotic polar solvents; and mixtures of two or more of them.

[0277] Examples of organic acids used in reactions include trifluoroacetic acid and acetic acid.

[0278] In the reaction, the acid is usually used in a ratio of 0.1 to 100 moles relative to 1 mole of compound (II-4).

[0279] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-4).

[0280] In the reaction, compound (Mh) is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-4).

[0281] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0282] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-3).

[0283] Reference manufacturing method 24 Compound (II-4) can be prepared by reacting the compound shown in formula (II-5) (hereinafter referred to as compound (II-5)) with hydrazine.

[0284] [Chemical Formula 51] [In the formula, X] b [This represents a chlorine or bromine atom; other symbols have the same meaning as described above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; haloalkanes; aromatic hydrocarbons; alcohols; aprotic polar solvents; water and mixtures of two or more of them.

[0285] Examples of hydrazines used in the reaction include anhydrous hydrazine, hydrazine monohydrate, and hydrazine monohydrochloride.

[0286] In the reaction, hydrazines are typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-5).

[0287] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0288] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-4).

[0289] Reference manufacturing method 25 Compound (II-5) can be produced by reacting the compound of formula (II-6) (hereinafter referred to as compound (II-6)) with a halogenating agent.

[0290] [Chemical Formula 52] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; haloalkanes; aromatic hydrocarbons; nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of them.

[0291] Examples of halogenating agents used in the reaction include phosphoryl chloride.

[0292] In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-6).

[0293] In the reaction, a base may be used as needed. Examples of bases include organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-6).

[0294] In the reaction, quaternary ammonium salts may be used as needed. Examples of quaternary ammonium salts include benzyltriethylammonium chloride. When using quaternary ammonium salts in the reaction, they are typically used in a ratio of 0.1 to 5 moles relative to 1 mole of compound (II-6).

[0295] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0296] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-5).

[0297] Reference manufacturing method 26 Compound (II-6) can be produced by reacting the compound shown in formula (II-7) (hereinafter referred to as compound (II-7)) with compound (IM).

[0298] [Chemical Formula 53] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-7) instead of compound (I-8) according to manufacturing method 2.

[0299] Reference manufacturing method 27 Compound (II-7) can be produced by reacting the compound of formula (II-8) (hereinafter referred to as compound (II-8)) with a halogenating agent.

[0300] [Chemical Formula 54] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-8) instead of compound (I-6) according to reference manufacturing method 3.

[0301] Reference manufacturing method 28 Compound (II-8) can be produced by reacting the compound shown in formula (II-9) (hereinafter referred to as compound (II-9)) with the compound shown in formula (Mi) (hereinafter referred to as compound (Mi)).

[0302] [Chemical Formula 55] [In the formula, R] y [This indicates C1-C4 alkyl groups; other symbols have the same meaning as above.] Reactions are typically carried out in a solvent. Examples of solvents used in reactions include alcohols; ethers; aromatic hydrocarbons; nitriles; aprotic polar solvents; halogenated hydrocarbons; and mixtures of two or more of these.

[0303] In the reaction, compound (Mi) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (II-9).

[0304] In the reaction, a base may be used as needed. Examples of bases include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal carbonates; and organic bases. When a base is used in the reaction, it is usually used in a ratio of 1 to 10 moles relative to 1 mole of compound (II-9).

[0305] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 24 hours.

[0306] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-8).

[0307] The compound (Mi) is a commercially available compound or can be manufactured using known methods.

[0308] Compound (II-9) is known or can be prepared by known methods as described in Tetrahedron (2013) 69, 11092-11108, etc.

[0309] Reference manufacturing method 29 The compound shown in formula (II-10) (hereinafter referred to as compound (II-10)) can be produced by reacting the compound shown in formula (II-11) (hereinafter referred to as compound (II-11)) with a halogenating agent.

[0310] [Chemical Formula 56] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-11) instead of compound (I-6) according to reference manufacturing method 3.

[0311] Reference manufacturing method 30 Compound (II-11) can be prepared by reacting the compound of formula (II-12) (hereinafter referred to as compound (II-12)) with compound (Mh) in the presence of an acid.

[0312] [Chemical Formula 57] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-12) instead of compound (II-4) according to reference manufacturing method 23.

[0313] Reference manufacturing method 31 Compound (II-12) can be prepared by reacting the compound of formula (II-13) (hereinafter referred to as compound (II-13)) with hydrazine.

[0314] [Chemical Formula 58] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-5) instead of compound (II-5) according to reference manufacturing method 24.

[0315] Reference manufacturing method 32 Compound (II-13) can be produced by reacting compound (II-8) with a halogenating agent.

[0316] [Chemical Formula 59] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-8) instead of compound (II-6) according to reference manufacturing method 25.

[0317] Reference manufacturing method 33 Compound (II-3A) can be produced by reacting the compound shown in formula (II-14) (hereinafter referred to as compound (II-14)) with compound (IM).

[0318] [Chemical Formula 60] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-14) instead of compound (I-8) according to manufacturing method 2.

[0319] Reference manufacturing method 34 Compound (II-14) can be produced by reacting the compound shown in formula (II-15) (hereinafter referred to as compound (II-15)) with the compound shown in formula (Mj) (hereinafter referred to as compound (Mj)).

[0320] [Chemical Formula 61] [In the formula, X] c R represents a chlorine atom, a bromine atom, or an iodine atom. z [This indicates C1-C3 alkyl groups; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; aromatic hydrocarbons; aprotic polar solvents; halogenated hydrocarbons; and mixtures of two or more of them.

[0321] In the reaction, compound (Mj) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (II-15).

[0322] In the reaction, acids may be used as needed. Examples of acids include organic acids such as acetic acid and p-toluenesulfonic acid. When an acid is used in the reaction, it is usually used in a ratio of 0.1 to 100 moles relative to 1 mole of compound (II-15).

[0323] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0324] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-14).

[0325] Reference manufacturing method 35 Compound (II-15) can be produced from the compound represented by formula (II-16) (hereinafter referred to as compound (II-16)).

[0326] [Chemical Formula 62] [In the formula, PG] 1 [This represents 2,4,6-trimethoxyphenylmethyl, 2,4-dimethoxyphenylmethyl, or 4-methoxyphenylmethyl; other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; alcohols; aromatic hydrocarbons; aprotic polar solvents; halogenated hydrocarbons; water; and mixtures of two or more of these.

[0327] In the reaction, acids may be used as needed. Examples of acids include inorganic acids such as hydrochloric acid and organic acids such as trifluoroacetic acid and p-toluenesulfonic acid. When an acid is used in the reaction, it is usually used in a ratio of 0.1 to 100 moles relative to 1 mole of compound (II-16).

[0328] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 72 hours.

[0329] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-15).

[0330] Reference manufacturing method 36 Compound (II-16) can be produced by reacting the compound shown in formula (II-17) (hereinafter referred to as compound (II-17)) with the compound shown in formula (Mk) (hereinafter referred to as compound (Mk)).

[0331] [Chemical Formula 63] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; aromatic hydrocarbons; aprotic polar solvents; nitriles; halogenated hydrocarbons; and mixtures of two or more of them.

[0332] In the reaction, compound (Mk) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (II-17).

[0333] In the reaction, a base may be used as needed. Examples of bases include alkali metal carbonates and organic bases. When a base is used in the reaction, it is usually used in a ratio of 0.1 to 10 moles relative to 1 mole of compound (II-17).

[0334] The reaction temperature is typically in the range of -20 to 200°C. The reaction time is typically in the range of 0.1 to 48 hours.

[0335] After the reaction is complete, water can be added to the reaction mixture, and extraction can be performed using an organic solvent. Post-processing operations such as drying and concentrating the organic layer are then carried out to obtain compound (II-16).

[0336] Reference manufacturing method 37 Compound (II-17) can be produced by reacting compound (II-7) with a halogenating agent.

[0337] [Chemical Formula 64] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-7) instead of compound (II-6) according to reference manufacturing method 25.

[0338] Reference manufacturing method 38 The compound shown in formula (II-18) (hereinafter referred to as compound (II-18)) can be produced from compound (II-10).

[0339] [Chemical Formula 65] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out, for example, according to the methods described in Green's PROTECTIVE GROUPS in ORGANIC SYNTHESIS FORTHEDITION P.727 or P.750.

[0340] Compound (II-18) sometimes forms acid addition salts. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid.

[0341] Reference manufacturing method 39 Compound (II-19) can be produced by reacting compound (II-18) with compound (I-3).

[0342] [Chemical Formula 66] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-18) instead of compound (I-2) according to manufacturing method 1.

[0343] Reference manufacturing method 40 Compound (II-3) can be produced by reacting compound (II-10) with compound (IM).

[0344] [Chemical Formula 67] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (II-10) instead of compound (I-8) according to manufacturing method 2.

[0345] The compounds of the present invention may be used in combination or in combination with one or more components (hereinafter referred to as the component) selected from the group consisting of group (a), group (b), group (c) and group (d) below.

[0346] The aforementioned combination or use refers to using the compound of the present invention and the ingredient simultaneously, separately, or at intervals.

[0347] When the compound of the present invention and the ingredient are used simultaneously, the compound of the present invention and the ingredient may be contained in separate formulations or in the same formulation.

[0348] One aspect of the present invention is a composition comprising one or more components selected from groups (a), (b), (c) and (d) (i.e., the component itself) and the compound of the present invention (hereinafter referred to as composition A).

[0349] Group (a) comprises acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABA-gated chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormones, multisite inhibitors, chordal organ TRPV channel modulators, mite growth inhibitors, and insect midgut membrane disruption derived from microorganisms. This group comprises insecticides, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncoupling agents, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin-based insecticides), chitin biosynthesis inhibitors, ecdysone inhibitors, ecdysone receptor agonists, octopamine receptor agonists, inhibitors of mitochondrial electron transport chain complexes I, II, III, and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ranotin receptor modulators (e.g., diamide-based insecticides), string organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients. These ingredients are described according to their IRAC-based mechanisms of action.

[0350] Group (b) comprises nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., aniline-pyridine 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.

[0351] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0352] Group (d) is the group containing the repellent component.

[0353] Examples of combinations of this component with the compounds of the present invention are described below. For example, alanycarb + SX refers to the combination of alanycarb and SX.

[0354] It should be noted that the abbreviation SX refers to the compounds of the present invention selected from any of the compound groups SX1 to SX1338 and compounds 1 to 58 of the present invention. Furthermore, all the ingredients described below are known ingredients and can be obtained from commercially available formulations or manufactured by known methods. If the ingredient is a microorganism, it can also be obtained from a microbial depository. It should be noted that the numbers in parentheses represent CAS RN (registered trademark).

[0355] The combination of the component of group (a) above with the compounds of the present invention: Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acridine lactate + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide Phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus Angulatus + SX, Bendiocal + SX, Benfluthrin + SX, Benfuracarb + SX, Bensultap + SX, Benzoximate + SX, Benzpyrimoxan + SX, Beta-cyfluthrin + SX, Beta-cypermethrin + SX, Bifenazate + SX, Bifenthrin + SX, Bioallethrin + SX, Bioresmethrin + SX, Bistrifluron + SX, Borax + SX, Boric acid acid) + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphidePhosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride Hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, 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 Dryopteris filix-mas + SX, emamectin-benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethylO-(4-nitrophenyl)phenylphosphonothioate, 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, extract of Azadirachta indica +SX, extract of Cassia nigricans +SX, extract of clitoria ternatea +SX, comfrey extract... Symphytum officinale + 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, flucyanfenoxuron The following compounds are listed: flucythrinate + SX, fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, and furathiocarb + SX. Gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid) +SX, hydramethylnon +SX, hydroprene +SX, imicafos +SX, imidacloprid +SX, imidaclothiz +SX, imiprothrin +SX, indazapyroxamet +SX, indoxacarb +SX, isocycloseram +SX, isofenphos +SX, isoprocarb +SX, isopropyl-O-(methoxyaminothiophosphoryl)salicylate salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX, kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oiloil) + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX, nicotine-sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, Chenopodium anthelminticum seed oil (oil of the seeds of Chenopodium)Anthelminticum + SX, Omethoate + SX, Oxamyl + SX, Oxazosulfyl + SX, Oxydemeton-methyl + SX, Parathion + SX, Parathion-methyl + SX, Permethrin + SX, Phenothrin + SX, Phenthoate + SX, Phorate + SX, Phosalone + SX, 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, piraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyri... minostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SXMetaborate + 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 ... 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, 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, 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 GV (granulovirus) strain BV-0001) + SX, Soybean Noctuid Moth Nucleopolyhedrovirus (Anticarsia gemmatalis MNPV (multiple nucleocapsidnucleopolyhedrovirus)) + SX, Alfalfa Silver-striped Noctuid Moth Nucleopolyhedrovirus (Autographa californica MNPV) + SX, Codling Moth Granulovirus V15 (Cydia pomonella GV strain V15) + SX, Codling Moth Granulovirus V22 (Cydia pomonella GV strain V22) + SX, Apple Aberrant Leaf Roller Granulovirus (Cryptophlebia leucotreta GV) + SX, Pine Caterpillar Polyhedrovirus (Dendrolimus) punctatuscypovirus) + SX, Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003 + SX, Helicoverpazea NPV + SX, Lymantria disparNPV+SX, Mamestra brassicae NPV+SX, Mamestra configurata NPV+SX, Neodiprion abietis NPV+SX, Neodiprion lecontei NPV+SX, Neodiprionsertifer NPV+SX, Nosema locustae NPV+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodopteraexigua NPV+SX MNPV)+SX, Spodoptera littoralis MNPV+SX, Spodoptera litura NPV+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637+SX, Bacillus megaterium+SX, Bacillus sp. strain AQ175+SX, Bacillus sp. strain AQ177 AQ177) + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52AQ52)+SX, Bacillus thuringiensis strain BD#32+SX, Bacillus thuringiensis strain CR-371+SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200 NB200)+SX, 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 EG2348)+SX, Bacillus thuringiensis subsp. Kurstakistrain EG7841+SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19The following strains were tested: EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, and Bacillus thuringiensis subsp. Tenebriosis strain NB176. Tenebriosis strain NB176) + SX, Bacillus thuringiensis subsp. thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp. Morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis Bacillus thuringiensis var. israelensis + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype H-14The following strains were tested: * Bacillus thuringiensis var. japonensis strain buibui* (serotype strain H-14) + SX; * Bacillus thuringiensis var. san diego strain M-7* (serotype strain H-14) + SX; * Bacillus thuringiensis var. 7216* (serotype strain H-14) + SX; * Bacillus thuringiensis var. aegypti ... ATCC74040) +SX, Beauveria bassiana strain GHA +SX, Beauveria brongniartii +SX, Burkholderia rinojensis strain A396 +SX, Chromobacterium subtsugae strain PRAA4-1T +SX, Dactyllela ellipsospora +SX, Decylaria thaumasia +SX, Hirsutella minnesotensis +SX, Hirsutella rhossiliensis +SX, Hirsutella thompsonii +SX, Lagenidium giganteum +SX, Lecanicillium lecanii strain KV01 KV01)+SX, conidia of strain DAOM198499 (Verticillium lecanii conidia of strain DAOM198499)+SX, conidia of strain DAOM216596 (Verticillium lecanii conidia of strain KV01)+SX, conidia of strain DAOM216596 (Verticillium lecanii conidia of strain KV01)+SX, conidia of strain DAOM19849 ...DAOM216596)+SX, Lecanicillium muscarium strain Ve6+SX, Metarhizium anisopliae strain F52+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae var. acridum+SX, Metarhizium anisopliae BIPESCO 5 / F52+SX, Metarhizium flavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomyces fumosoroseus Apopka strain 97+SX, Paecilomyces lilacinus strain 251 251)+SX, Paecilomyces tenuipes strain T1+SX, Paenibacillus popilliae+SX, Pasteuria nishizawaestrain Pn1+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia entomophila+SX, Verticillium chlamydosporium+SX, Verticillium lecani strain NCIM1312+SX, Wolbachia pipientis+SX.

[0356] The combination of this component of group (b) above with the compounds of the present invention: Acibenzolar-S-methyl + SX, Aldimorph + SX, Ametoctradin + SX, Aminopyrifen + SX, Amisulbrom + SX, Anilazine + SX, Azaconazole + SX, Azoxystrobin + SX, Basic copper sulfate sulfate) + SX, benalaxyl + SX, benalaxyl-M + SX, benodanil + SX, benomyl + SX, benthiavalicarb + SX, benthiavalicarb-isopropyl + SX, benzovindiflupyr + SX, binapacryl + SX, biphenyl + SX, bitertanol + SX, bixafen + SX, blasticidin-S + SX, Bordeaux mixture mixture) + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionat + SX, chitin + SX, chloroinconazide + SX, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, basic copper chloride oxychloride) + SX, copper(II) sulfate (copper(II))sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX Diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX, dinocap + SX, dipotassium hydrogen phosphate Hydrogenphosphite + SX, Dipymetitrone + SX, Dithianon + SX, Dodecylbenzenesulphonic acidbisethylenediamine copper(II) salt + SX, Dodemorph + SX, Dodine + SX, Edifenphos + SX, Enoxastrobin + SX, Epixaconazole + SX, Etaconazole + SX, Ethaboxam + SX, Ethirimol + SX, Etridiazole + SX, Allium sativum extract + SX, Lupine cotyledon extract (“BLAD”) + SX, Equisetum extract Arvense) + SX, Melaleuca alternifolia extract + SX, Polygonum cuspidatum extractReynoutria sachalinensis + SX, extract of Tropaeolum majus + 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, fentinacetate + 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 Imazalil + SX, Imibenconazole + SX, Iminoctadine + SX, Iminoctadine Triacetate Triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX, ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamid + SX, isoflucypram + SX, isoprethiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, leaves and bark of oak treesQuercus + SX, Mancozeb + SX, Mandestrobin + SX, Mandipropamid + SX, Maneb + ​​SX, Mefentrifluconazole + SX, Mepanipyrim + SX, Mepronil + SX, Meptyldinocap + SX, Metalaxyl + SX, Metalaxyl-M + SX, Metrilpicoxamid + SX, Metconazole + SX, Methasulfocarb + S X, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + SX, ofuronamide + SX, orysastrobin + SX, oxadixyl + SX, oxathiapiprolin + SX, oxine-copper + SX, oxolinic Acid) + SX, Oxpoconazole + SX, Oxpoconazole fumarate + SX, Oxycarboxin + SX, Oxytetracycline + SX, Pefurazoate + SX, Penconazole + SX, Pencycuron + SX, Penflufen + SX, Penthiopyrad + SX, Phenamacril + SX, Phosphorous acid + SX, Phthalide + SX, Picarbutrazox + SX, Picoxystrobin + SX, Piperalin + SX, Polyoxins + SX, Potassium hydrogencarbonate + SX, Potassium dihydrogen phosphatedihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, piraclostrobin + SX, pyramet ostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract extract) +SX, quinconazole +SX, quinofumelin +SX, quinoxyfen +SX, quintozene +SX, saponins of Chenopodium quinoa +SX, seboctylamine +SX, sedaxane +SX, silthiofam +SX, simeconazole +SX, sodium bicarbonateHydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thioprazan + SX, Thioprazan-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos -methyl)+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX, triadimefon+SX, triadimenol+SX, triazoxide+SX, chlorpyrifos+SX, tricyclazole+SX, triridemorph+SX, trifloxystrobin+SX, triflumizole+SX, triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX, vinclozolin+SX, yellow mustard powder ( Mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidin (1202781-91-6)+SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidin (929908-57-6)+SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidin (1052688-31-9)+SX, N '-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylformamidin (2055589-28-9)+SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidin (2055756-21-1)+SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidin (2062599-39-5)+SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl- [5-Methoxyphenyl]-N-isopropyl-N-methylformamidinium (2101814-55-3)+SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformamidinium (1817828-69-5)+SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (1362477-26-6)+SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin- 2-yl]quinazolin (1257056-97-5) + SX, (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridine-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2)+SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol4-Triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5)+SX, 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylic acid methyl ester (1791398-02-1)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (20 19215-86-0)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylonitrile (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylonitrile (2018317-25-2) )+SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082661-43-4)+SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propane-2-ol (2082660-27-1)+SX, ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879- 98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-indene-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-54-3)+SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]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 (2098918-25-1) +SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one (2098918-25-1) +SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol) -3-yl]phenyl}methyl)isoxazolin-3-one (2098918-26-2)+SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide+SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropionamide+SX, N-methoxy-N'-methyl-N-({4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9)+SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(4-bromo-7-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromoindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine 3-(7-bromo-4-fluoroindole-1-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]- L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester +SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine 3-(3,5-dichloropyridin-2-yl)but-2-yl ester +SX, N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester) N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate)+SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropionic acid +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide +SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionic acid +SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionic acid +SX, 3,3,3-Trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propionamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butyramide + SX, N-methoxy-N-methyl-N'-({4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2,4-Oxadiazol-3-yl]phenyl}methyl)morpholin-3-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3-one+SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinane-3-one+SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azacycloheptane-2-one+SX, 4,4 -Dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one +SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one +SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylic acid ethyl ester +SX, N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-propyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX,4-Oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-methoxy-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N-methoxy-N-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxamide +SX, N,N-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-1,2,4-triazol-3-amine +SX, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol- [3-yl]benzamide +SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate methyl ester +SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate ethyl ester +SX, 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate methyl ester +SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl] ]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide +SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile +SX, 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester +SX, 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]oxy [Phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester +SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-Dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3,4]oct-1-yl)-5-methylthiazol-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazol-4-carboxamide +SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2 -[(2-methylpropionyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-{[(oxetane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +S X, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3, 4-Oxadiazol-2-yl]-N-[1-(6-chloropyridin-3-yl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluoro-3-methoxyphenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluoromethyl ...6-Difluorophenyl)cyclopropyl]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + S X, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[ 2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2-methylpropionamide +SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2,2-di ...hydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2,2-dimethylpropionamide +SX, N-((2S)-1-{3-[2 [3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl]propane-2-yl)-2-methylpropionamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propane-2-yl)-2-methylpropionamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-Dihydropyrimidin-1(2H)-ylpropane-2-yl)-2-methylpropionamide + SX, methyl carbamate ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazole-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazole-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazole-3-yl]) Methyl 2-methylphenyl)carbamate + SX, (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-2-acrylate + SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-acrylate + SX, (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxy-2-acrylate Ester + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-di Methyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinoline-4(3H)-one + SX, (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]-2-acrylate methyl ester + SX, Agrobacterium radioactivity strain K1026 The following strains were tested: * *Agrobacterium radiobactor strain K1026* + SX; * *Bacillus amyloliquefaciens strain PTA-4838* + SX; * *Bacillus amyloliquefaciens strain AT332* + SX; * *Bacillus amyloliquefaciens strain B3* + SX; * *Bacillus amyloliquefaciens strain D747* + SX; * *Bacillus amyloliquefaciens strain DB101*.DB101) + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 QST713) + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + 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 GB344 + SX. Bacillus pumilus strain GB34) + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153The following strains of Bacillus subtilis were tested: AQ153 + SX, AQ743 + SX, BU1814 + SX, D747 + SX, DB101 + SX, FZB24 + SX, GB03 + SX, HAI0404 + SX, and IAB / BS03. IAB / BS03) + SX, Bacillus subtilis strain MBI600 + SX, 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 FZB24) + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54Wisconsinstrain M54) + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, Cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 Fo47) + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxastrain AC-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 aureofaciens strain AFS009 chlororaphisstrain AFS009) + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506The following strains of Pseudomonas fluorescens ( strain A506) were added to the SX strain: *Pseudomonas fluorescens* strain CL145A + SX, *Pseudomonas fluorescens* strain G7090 + SX, *Pseudomonas* sp. strain CAB-02 + SX, *Pseudomonas syringae* strain 742RS + SX, *Pseudomonas syringae* strain MA-4 + SX, *Pseudozyma flocculosa* strain PF-A22UL + SX, *Pseudomonas rhodesiae* strain HAI-0804 + SX, and *Pythium oligandrum* strain DV74. The following strains were tested: * *Pythium oligandrum* strain DV74 + SX, *Streptomyces griseoviridis* strain K61 + 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, and *Trichoderma asperellum* strain SKT-1. SKT-1) + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma CNCMTrichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atrovirides strain IMI 206040 + SX, Trichoderma atrovirides strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichodermagamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 DB104)+SX, Trichoderma harzianum strain DSM 14944+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 SF+SX, Trichoderma harzianum strain T22+SX, Trichoderma harzianum strain T39T39) + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, Trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichodermaviride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX.

[0357] The combination of the component of group (c) above with the compounds of the present invention: 1-Methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) Acid + SX, 5-aminolevulinic acid hydrochloride + SX, 6-benzylaminopurine + SX, abscisic acid + SX, AVG (aminoethoxyvinylglycine) + SX, anisiflupurin + SX, ancymidol + SX, butralin + SX, calcium carbonate + SX, calcium chloride + SX, calcium formate + SX, calcium peroxide + SX, calcium polysulfide + SX, calcium sulfate + SX, chlormequat-chloride + SX, chlorpropham + SX, choline chloridechloride) + SX, cloprop + SX, cyanamide + SX, cyclanilide + SX, daminozide + SX, decan-1-ol + SX, dichlorprop + SX, dikegulac + SX, dimethipin + SX, diquat + SX, ethephon + SX, ethychlozate + SX, flumetralin + SX, flurprimidol + SX, forchlorfenuron + SX, formononetin + SX, gibberellin A A) + SX, Gibberellin A3 + SX, Inabenfide + SX, Kinetin + SX, Lipochitooligosaccharide SP104 + SX, Maleic hydrazide + SX, Mefluidide + SX, Mepiquat-chloride + SX, Oxidized glutathione + SX, Paclobutrazol + SX, Pendimethalin + SX, Prohexadione-calcium + SX, Prohydrojasmon + SX, Pyraflufen-ethyl + SX, Sintofen + SX, Sodium 1-naphthaleneacetate + SX, Sodium cyanate cyanate) + SX, thidiazuron + SX, triapenthenol + SX, tribufos + SX, trinexapac-ethyl + SX, uniconazole-P + SX, 2-(naphthalen-1-yl)acetamide + SX, [4-oxo-4-(2-phenylethyl)amino]butyric acid + SX, methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate + SX, 3-[(6-chloro-4-phenylquinazolin-2-yl)amino]propane-1-ol + SX, Claroideoglomusetunicatum) + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Giaspora margarita + SX, Giaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 strain + SX, Rhizophagus irregularis DAOM Azospirillum caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 strain + SX, Bradyrhizobium japonicum TA-11 strain + SX, Bradyrhizobium japonicum USDA 110 strain + SX, Bradyrhizobium liaoningense strain + SX, Bradyrhizobium lupini strain + SX, Delftia acidovorans RAY209 strain + SX, Mesorhizobium ciceri strain + SX, MesorhizobiumRhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini yellow mosaic virus (attenuated strain) YellowMosaik Virus weak strain)+SX.

[0358] The combination of the component of group (d) above with the compounds of the present invention: Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0359] The ratio of the compound to the component of this invention is not particularly limited, but examples of weight ratios (compound of this invention: component of this invention) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, etc.

[0360] The compounds of this invention are effective against harmful arthropods such as harmful insects and mites, as well as harmful nematodes and harmful mollusks. Examples of harmful arthropods, nematodes, and mollusks include the following animals.

[0361] Hemiptera: Planthoppers include *Laodelphax striatellus*, *Nilaparvatalugens*, *Sogatella furcifera*, *Peregrinus maidis*, *Javesella pellucida*, *Perkinsiella saccharicida*, *Tagosodesorizicolus*, and *Stenocranus pacificus*; Planthoppers include: *Nephotettix cincticeps*, *Nephotettix virescens*, *Nephotettix nigropictus*, *Recilia dorsalis*, *Empoasca onukii*, *Empoasca fabae*, and *Dalbulus*. Leafhoppers such as maidis, Cofanaspectra, and Amrasca biguttula biguttula belong to the family Cicadellidae; leafhoppers such as Philaenus spumarius belong to the family Aphrophoridae; and leafhoppers such as Mahanarvaposticata and Mahanarva fimbriolata belong to the family Cercopidae.Beet aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), spiraecola aphid (Aphis spiraecola), peach aphid (Myzus persicae), plum short-tailed aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), rose apple aphid (Dysaphis plantaginea), cabbage tube aphid (Lipaphis erysimi), potato long-tube aphid (Macrosiphum euphorbiae), eggplant weevil aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal tube aphid (Rhopalosiphumpadi), corn aphid (Rhopalosiphum maidis), orange aphid (Toxoptera citricida), peach pink aphid (Hyalopterus pruni), sorghum aphid (Melanaphis) The aphid family includes: *Sacchari*, *Tetraneuranigriabdominalis*, *Ceratovacuna lanigera*, *Eriosomalanigerum*, and *Sitobion avenae*; the root aphid family includes: *Daktulosphaira vitifoliae*, *Phylloxera devastatrix*, *Phylloxera notabilis*, and *Phylloxera russelae*; and the ball aphid family includes: *Adelges tsugae*, *Adelges piceae*, and *Aphrastasia pectinatae*.The species include the black rice bug (Scotinophara lurida), the Malayan black rice bug (Scotinophara coarctata), the black-bearded green rice bug (Nezara antennata), the northern two-spotted bug (Eysarcoris aeneus), the large-spined white-spotted bug (Eysarcoris lewisi), the broad-spotted two-spotted bug (Eysarcoris ventralis), the false two-spotted bug (Eysarcoris annamita), the tea-winged bug (Halyomorpha halys), the green rice bug (Nezara viridula), the brown bug (Euschistus heros), the red-banded bug (Piezodorus guildinii), the rice bug (Oebalus pugnax), the stink bug (Dichelops melacanthus), and the wall stink bug (Piezodorus hybneri), belonging to the family Pentatomidae; the burrowing brown bug (Scaptocoris). Cydnidae (soil bugs such as *Castanea*); Alydidae (spider bugs such as *Riptortus clavatus*, *Leptocorisa chinensis*, and *Leptocorisa acuta*); Coreidae (leaf bugs such as *Cletus punctiger* and *Leptoglossus australis*); Lygaeidae (long bugs such as *Cavelerius saccharivorus*, *Togohemipterus*, and *Blissus leucopterus*); Trigonotylus caelestialium, Stenotus rubrovittatus, and Stenodema. Miridae (including species such as *Calcarata* and *Lygus lineolaris*); Aleyrodidae (including species such as *Trialeurodes vaporariorum*, *Bemisia tabaci*, *Dialeurodescitri*, *Aleurocanthus spiniferus*, *Aleurocanthus cameelliae*, and *Pealius euryae*).The species include scale insects of the family Diaspididae (such as *Abgrallaspis cyanophylli*, *Aonidiella aurantii*, *Diaspidiotus perniciosus*, *Pseudaulacaspis pentagona*, *Unaspis yanonensis*, and *Unaspis citri*); scale insects of the family Coccidae (such as *Ceroplastes rubens*); cottony cushion scales of the family Margarodidae (such as *Icerya purchasi* and *Icerya seychellarum*); and mealy cushion scales of the family Phenacoccus solani, Phenacoccus sonopsis, and *Planococcus rubens*. The family Pseudococcidae includes species such as *Pseudococcus comstocki*, *Planococcus citri*, *Pseudococcus calceolariae*, *Pseudococcus longispinus*, and *Brevennia rehi*. The family Psyllidae includes species such as *Diaphorina citri*, *Trioza erytreae*, *Cacopsylla pyrisuga*, *Cacopsylla chinensis*, *Bactericera cockerelli*, and *Cacopsylla pyricola*. The family Psyllidae includes species such as *Corythucha ciliata* and *Corythucha*. The family Tingidae includes species such as marmorata, pear lace bug (Stephanitis nashi), and cuckoo lace bug (Stephanitis pyrioides); the family Cimicidae includes species such as temperate bed bug (Cimex lectularius) and tropical bed bug (Cimex hemipterus); and the family Cicadidae includes species such as giant cicada (Quesada gigas).The Reduviidae family includes assassin bugs such as the harassing kissing bug (Triatoma infestans), the red-banded kissing bug (Triatoma rubrofasciata), the two-part kissing bug (Triatoma dimidiata), and the long red assassin bug (Rhodonius prolixus).

[0362] Lepidoptera: Rice stem borer (Chilo suppressalis), Chilo polychrysus, Rice white stem borer (Scirpophaga innotata), Rice three-stem borer (Scirpophaga incertulas), Rupela albina, Rice leaf roller (Cnaphalocrocis medinalis), Broad-striped brush-bearded leaf roller (Marasmia patnalis), Rice leaf roller (Marasmia exigua), Cotton leaf roller (Notarcha derogata), Asian corn borer (Ostriniafurnacalis), European corn borer (Ostrinia nubilalis), Cabbage borer (Hellula undalis), Grape leaf cutter moth (Herpetogramma luctuosale), Kentucky bluegrass stem borer (Parapediasia teterrellus), Rice three-spotted leaf borer (Nymphula) Crombidae (grass moths such as *Diatraea saccharalis*, *Leucinodesorbonalis*, etc.); Pyralidae (corn borers such as *Elasmopalpus lignosellus*, *Plodia interpunctella*, *Euzophera batangensis*, *Cadracautella*, etc.).Spodoptera litura, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotisipsilon, Agrotis segetum, Autographa nigrisigna, Plusia festucae, Chrysodeixis includens, Trichoplusia spp., Heliothis Noctuidae include genus *Heliothis* (e.g., *Virescens*), genus *Helicoverpa* (e.g., *Helicoverpa armigera*), genus *Helicoverpa* (e.g., *Helicoverpa zea*), genus *Anticarsia gemmatalis*, genus *Alabama argillacea*, and genus *Hydraecia immanis*; Pieris rapae includes butterfly species.The following moths belong to the family Tortricidae: pear fruit moth (Grapholita molesta), crabapple fruit moth (Grapholita dimorpha), soybean fruit moth (Leguminivora glycinivorella), soybean leafroller (Matsumuraeses azukivora), apple leafroller (Adoxophyes orana fasciata), tea leafroller (Adoxophyes honmai), tea long leafroller (Homona magnanima), apple yellow leafroller (Archips fuscocupreanus), apple leafroller (Cydiapomonella), yellow rice borer (Tetramoera schistaceana), bean shooter (Epinotiaaporema), citrus fruit fly (Citripestis sagittiferella), grape flower leafroller (Lobesia botrana), etc.; tea leafroller (Caloptilia). Theivora, Phyllonorycterringoniella, and other gracillariidae moths; Carposinidae moths, Carposina sasakii, and other carposinidae moths; Lyonetiidae moths, Leucoptera coffeella, Lyonetia clerkella, Lyonetia prunifoliella, and other tussock moths; Lymantriidae moths, Lymantriadispar, Euproctis spp., Euproctis pseudoconspersa, and other tussock moths; Plutellidae moths, Plutella xylostella, Anarsia lineatella, Helcystogrammatriannulella, Pectinophora Gelechiidae (including gossypiella, Phthorimaea operculella, and Tuta absoluta); Arctiidae (including Hyphantria cunea); and Castniidae (including Telchin licus).The following species are listed: Cossidae (wood-boring moths such as *Cossus insularis*); Geometridae (geometridae); Limacodidae (slug moths such as *Parasa lepida*); Stathmopodidae (slug moths such as *Stathmopoda masinissa*); Sphingidae (hawk moths such as *Acherontialachesis*); Sesiidae (clearwing moths such as *Nokona feralis*, *Synanthedon hector*, and *Synanthedon tenuis*); Hesperiidae (skipper moths such as *Parnaraguttata*); and Tineidae (grass moths such as *Tinea translucens* and *Tineolabisselliella*).

[0363] Thysanoptera: Thripidae (Frankliniella occidentalis), palm thistle (Thrips palmi), yellow thrips (Scirtothrips dorsalis), tobacco thrips (Thrips tabaci), flower thrips (Frankliniella intonsa), rice thrips (Stenchaetothrips biformis), American thorny thrips (Echinothrips americanus), avocado thrips (Scirtothrips perseae), etc.; Phlaeothripidae (Haplothrips aculeatus), etc.

[0364] Diptera: Anthomyiidae (including species such as *Delia platura*, *Delia antiqua*, and *Pegomya cunicularia*); Ulidiidae (including species such as *Tetanopsmyopaeformis*); Agromyzidae (including species such as *Agromyza oryzae*, *Liriomyza sativae*, *Liriomyza trifolii*, and *Chromatomyia horticola*); Chloropidae (including species such as *Chlorops oryzae*); Bactrocera cucurbitae (including species such as *Bactrocera dorsalis*, *Bactrocera latifrons*, and *Bactrocera cucurbitae*). Fruit flies (Tephritidae), including the Queensland fruit fly (Bactroceratryoni), Mediterranean fruit fly (Ceratitis capitata), apple fruit fly (Rhagoletis pomonella), and Japanese cherry fruit fly (Rhacochlaena japonica); water flies (Ephydridae), including the rice leaf miner (Hydrelliagriseola), rice philippina, and rice stalk water fly (Hydrelliasasakii); fruit flies (Drosophila suzukii) and black-bellied fruit flies (Drosophila melanogaster); flea flies (Phoridae), including the East Asian flea fly (Megaselia spiracularis); midges (Psychodidae), including the clogmia albipunctata; and mushroom midges (Bradysia). Sciaridae, including species such as *Difformis* and *Bradysia odoriphaga*; Cecidomyiidae, including species such as *Mayetiola destructor* and *Orseolia oryzae*; and Diopsidae, including species such as *Diopsis macrophthalma*.The species include: *Glossinidae* (Tsetse Fly, *Glossina palpalis*, *Glossina morsitans*, etc.); *Simuliidae* (Japonicum, *Simulium damnosum*, etc.); *Phlebotominae* (Lysimachia); *Tipulidae* (Tipulapaludosa, etc.); *Culex pipiens pallens*, *Culex tritaeniorhynchus*, *Culex pipiens f. molestus*, *Culex quinquefasciatus*, *Culex pipiens pipiens*, *Culex vishnui*, *Aedes albopictus*, and *Aedes aegypti*. Anopheles species include: *Anopheles aegypti*, *Anopheles sinensis*, *Anopheles gambiae*, *Anopheles stephensi*, *Anopheles coluzzii*, *Anopheles albimanus*, *Anopheles saintii*, *Anopheles arabiensis*, *Anopheles funestus*, *Anopheles darlingi*, *Anopheles farauti*, and *Anopheles minimus*, belonging to the Culicidae family; *Prosimulium yezoensis* and *Simulium ornatum*, belonging to the Simulidae family; *Tabanus trigonus*, belonging to the Tabanidae family; and houseflies (*Muscadomestica*), stable flies (*Muscina stabulans*), and stable stinging flies (*Stomoxys*). Muscidae (flies such as *Calcitrans* and *Haematobia irritans*); Calliphoridae; Sarcophagidae.Chironomidae (including species such as *Chironomus plumosus*, *Chironomus yoshimatsui*, and *Glyptotendipes tokunagai*); Fannidae (including species such as *Glyptotendipes*).

[0365] Coleoptera: Genus *Diabrotica* spp., including species such as the western corn rootworm (*Diabrotica virgifera virgifera*), the southern corn rootworm (*Diabrotica undecimpunctatahowardi*), the northern corn rootworm (*Diabrotica barberi*), the Mexican corn rootworm (*Diabrotica virgiferazeae*), the spotted cucumber leaf beetle (*Diabrotica balteata*), and the Cucurbit Beetle (*Diabrotica speciosa*), the bean leaf beetle (*Cerotoma trifurcata*), the grain leaf beetle (*Oulemamelanopus*), the cucumber beetle (*Aulacophora femoralis*), the yellow striped flea beetle (*Phyllotreta striolata*), the cabbage flea beetle (*Phyllotreta cruciferae*), the western black flea beetle (*Phyllotreta pusilla*), and the rapeseed flea beetle (*Psylliodes*). Chrysomelidae (leaf beetle), Psylliodes punctulata, Leptinotarsa ​​decemlineata, Oulema oryzae, Colaspis brunnea, Chaetocnema pulicaria, Chaetocnema confinis, Epitrix cucumeris, Dicladispa armigera, Myochrous denticollis, Laccoptera quadrimaculata, Epitrix hirtipennis, Phaeton brassicae, Medythiani grobilineata, etc.; Seedcorn beetle (Stenolophus lecontei), Clivina (corn beetle). Carabidae, including impressifrons;The following species belong to the Scarabaeidae family: * *Anomala cuprea*, *Anomala rufocuprea*, *Anomala albopilosa*, *Popillia japonica*, *Heptophyllapicea*, *Rhizotrogus majalis*, *Tomarus gibbosus*, *Holotrichia spp.*, *Phyllophaga crinita*, and other species in the *Phyllophaga* genus; *Diloboderus abderus* and other species in the *Diloboderus* genus; *Anthriibidae*, such as the coffee bean weevil *Araecerus coffeae*; and *Cylas*, the sweet potato ant weevil. Aponidae family including *Zabrotes subfasciatus*; Bruchidae family including *Zabrotes subfasciatus*; Scolytidae family including *Tomicus piniperda* and *Hypothenemus hampei*; West Indian sweet potato weevil *Euscepespostfasciatus*, alfalfa leaf weevil *Hypera postica*, maize weevil *Sitophilus zeamais*, rice weevil *Sitophilus oryzae*, grain weevil *Sitophilus granarius*, rice weevil *Echinocnemus squameus*, rice water weevil *Lissorhoptrus oryzophilus*, palm weevil *Rhabdoscelus lineaticollis*, cotton boll weevil *Anthonomus grandis*, parasitic grain weevil *Sphenophorus venatus*, southern maize long-beaked weevil *Sphenophorus callosus*, soybean stem weevil *Sternechus* Subsignatus, sugarcane weevil (Sphenophorus levis), rust weevil (Scepticus griseus), rust weevil (Scepticus uniformis), mouse weevil (Aracanthus spp.), cotton root borer (Eutinobothrus brasiliensis), etc., are all from the family Curculionidae.Tenebrionidae (including the red flour beetle *Tribolium castaneum*, the mixed flour beetle *Tribolium confusum*, and the black fungus beetle *Alphitobius diaperinus*); Coccinellidae (including the eggplant ladybug *Epilachna vigintioctopunctata*); Bostrychidae (including the brown powdery beetle *Lyctus brunneus* and the grain beetle *Rhizopertha dominica*); Ptinidae (spider beetles); Cerambycidae (longhorn beetles including the star longhorn beetle *Anoplophora malasiaca*, *Migdolus fryanus*, and the peach-necked longhorn beetle *Aromiabungii*); Melanotus okinawensis (click beetle), Agriotes fuscicollis (click beetle), and Melanotus (click beetle). Elateridae (click beetles), including genera such as *Leetus*, *Anchastus* spp., *Conoderus* spp., *Ctenicera* spp., *Limonius* spp., and *Aeolus* spp.; Staphylinidae (rove beetles), including *Paederus fuscipes*; Dermestidae (dermestid beetles), including *Anthrenus verbasci*, *Dermestes maculates*, and *Trogoderma granarium*; Anobiidae (grass beetles), including *Lasioderma serricorne* and *Stegobium paniceum*; and Cryptolestes (rusty grain beetle). Laemophloeidae (e.g., *ferrugineus*); Silvanidae (e.g., *Oryzaephilus surinamensis*); and Nitidulidae (e.g., *Brassicogethesaeneus*).

[0366] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red-winged locust (Nomadacrisseptemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Long-fronted locust (Melanoplus differentialis), Two-banded grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clearwing locust (Camnula pellucida), Desert locust (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Small-winged rice locust (Oxya The family Acrididae includes species such as *Yezoensis*, *Oxya japonica*, and *Patanga succincta*; the family Gryllotalpidae includes species such as *Gryllotalpa orientalis*; the family Gryllidae includes species such as *Acheta domestica* and *Teleogryllus emma*; and the family Tettigoniidae includes species such as *Anabrus simplex*.

[0367] Hymenoptera: Tenthredinidae (leaf bee family), including species like *Athalia rosae* and *Athalia japonica*; genera such as *Solenopsis* spp. (fire ant), *Solenopsis geminata* (tropical fire ant); genera such as *Atta* spp. (brown leaf-cutting ant), *Acromyrmex* spp. (leaf-cutting ant), *Paraponera clavata* (bullet ant), *Ochetellus glaber* (hairless stink ant), *Monomoriumpharaonis* (small yellow house ant), *Linepithema humile* (Argentine ant), *Formica japonica* (Japanese black brown ant), *Pristomyrmex punctutus* (striated leaf-cutting ant), and *Pheidole* (broad-knotted big-headed ant). Formic ants (Camponotus spp.), including *Pheidolemegacephala*, *Camponotus japonicus*, and *Camponotus obscuripes*; ants (Pogonomyrmex spp.), including *Pogonomyrmex occidentalis*; ants (Wasmania spp.), including *Wasmania auropunctata*; ants (Anoplolepis gracilipes) (Formicidae); wasps (Vespa mandarinia), horned hornets (Vespa simillima), black-tailed wasps (Vespa analis), black-breasted wasps (Vespa velutina), and domestic wasps (Polistes jokahamae) (Vespidae); large tree wasps (Urocerus). The family Siricidae includes species such as gigas; the family Bethylidae includes species such as swollen-legged bees.

[0368] Blattodea: Includes species such as the German cockroach (Blattella germanica) and the family Ectobiidae; species such as the American cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australasiae), brown-spotted cockroach (Periplaneta brunnea), and oriental cockroach (Blattaorientalis); species such as the northern subterranean termite (Reticulitermes speratus), Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, Neotermes koshunensis, and Glyptotermes. The termites include species such as *Glyptotermes satsumensis*, *Glyptotermes nakajimai*, *Glyptotermes fuscus*, *Hodotermopsis sjostedti*, *Coptotermes guangzhouensis*, *Reticulitermes amamianus*, *Reticulitermes miyatakei*, *Reticulitermes kanmonensis*, *Nasutitermes takasagoensis*, *Pericapritermes nitobei*, *Sinocapritermes mushae*, and *Cornitermes cumulans*, all belonging to the family Termitidae.

[0369] Siphonaptera: Human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog comb flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), bird crest flea (Echidnophaga gallinacea) and other flea families (Pulicidae); skin-penetrating flea (Tunga penetrans) and other sand flea families (Hectopsyllidae); European mouse flea (Nosopsyllus fasciatus) and other angular leaf flea families (Ceratophyllidae).

[0370] Order Psocodae: Human head louse (Pediculus humanus capitis) and other louse families (Pediculidae); pubic louse (Pthirus pubis) and other pubic louse families (Pthiridae); blood louse family (Haematopinidae) such as bovine blood louse (Haematopinuseurysternus) and swine blood louse (Haematopinus suis); gnatidae family (Linognathidae) such as calf gnatidae (Linognathus vituli), sheep gnatidae (Linognathus ovillus), and buffalo blind louse (Solenopotescapillatus); bovicoliidae family (Bovicoliidae) such as bovine hairy louse (Bovicola bovis), sheep gnatidae (Bovicolaovis), bovicola breviceps, Damalinia forficula, and Werneckiella spp.); dog-biting louse (Trichodectes). Lice such as *Fragaria canis*, *Felicola subrostratus*, etc. (Trichodectidae); *Menopon* gallinae, *Menacanthus stramineus*, *Trinoton* spp., etc. (Menoponidae); *Cummingsia* spp., etc. (Trimenoponidae); *Trogium pulsatorium*, etc. (Trogiidae); *Liposcelis corrodens*, *Liposcelis bostrychophila*, *Liposcelis pearmani*, *Liposcelisentomophila*, etc. (Liposcelidae or Liposcelididae).

[0371] Thysanura: Ctenolepisma villosa, Lepismasaccharina and other Lepismatidae.

[0372] Order Acari: Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligochus spp., etc.; Family Tetranychidae; Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculus schlechtendali, Aceria diospyri, Aceria leucocephalus. Eriophyidae (including species such as *Eriophyta tosichella* and *Shevtchenkella sp.*); Tarsonemidae (including species such as *Polyphagotarsonemus latus*); Tenuipalpidae (including species such as *Brevipalpus phoenicis*); and Tuckerellidae (family such as Tuckerellidae).Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Dermacentor andersoni, Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Ixodes pacificus, Ixodes holocyclus, Ixodes ricinus, Amblyomma americanum, Amblyomma maculatum, Rhipicephalus Microplus, including the family Ixodidae (Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus decoloratus); the family Argasidae (Argas persicus, Ornithodoros hermsi, Ornithodoros turicata); the family Acaridae (Tyrophagus putrescentiae, Tyrophagus similis); the family Pyroglyphidae (Dermatophagoides farinae, Dermatophagoides pteronyssinus); and the family Cheyletus. Carnivorous mites include *Cheyletus eruditus*, *Cheyletus malaccensis*, *Chelacaropsis moorei*, and *Cheyletiella yasguri*, among others, belonging to the family Cheyletidae.The following mites are included: sheep itch mites (Psoroptes ovis), horse itch mites (Psoroptes equi), mutant knee mites (Knemidocoptes mutans), ear mites (Otodectes cynotis), and skin mites (Chorioptes spp.), belonging to the family Psoroptidae; cat ear mites (Notoedres cati), cat anal mites (Notoedres muris), and human scabies mites (Sarcoptes scabiei), belonging to the family Sarcoptes; rabbit scabies mites (Listrophorus gibbus), belonging to the family Listrophoridae; chicken scabies mites (Dermanyssus gallinae), belonging to the family Dermanyssidae; forest scabies mites (Ornithonyssus sylviarum), avian scabies mites (Ornithonyssus bacoti), belonging to the family Macronyssidae; and Varroa mites. Varoidae (such as *Jacobsoni*); Demodicidae (such as *Demodex canis* and *Demodex cati*); Trombulidae (such as *Leptotrombidium akamushi*, *Leptotrombidium pallidum*, and *Leptotrombidium scutellare*).

[0373] Araneae: Eutichuridae (red-clawed spiders such as Cheiracanthium japonicum); Theridiidae (ball spiders such as Latrodectus hasseltii).

[0374] Polydesmida: including Oxidus gracilis, Nedyopustambanus, and other species in the family Paradoxosomatidae.

[0375] Isopoda: Armadillidium vulgare, Armadillidiidae.

[0376] Chilopoda: Scutigeridae (e.g., Thereuonema hilgendorfi); Scolopendridae (e.g., Scolopendra subspinipes); Ethopolyidae (e.g., Bothropolys rugosus).

[0377] Gastropoda: Limacidae (including Limax marginatus and Limaxflavus); Philomycidae (including Meghimatium bilineatum); Ampullariidae (including Pomacea canaliculata); Lymnaeidae (including Austropeplea ollula).

[0378] Nematodes: Rice stem nematode (Aphelenchoides besseyi) and other nematodes of the family Aphelenchoididae; coffee nematode (Pratylenchus coffeae), piercing nematode (Pratylenchus brachyurus), neglected nematode (Pratylenchus neglectus), banana nematode (Radopholus similis) and other short-bodied nematodes of the family Pratylenchidae; Javan root-knot nematode (Meloidogyne javanica), southern root-knot nematode (Meloidogyne incognita), guava root-knot nematode (Meloidogyne enterolobii), northern root-knot nematode (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato golden nematode (Globodera). The family includes Heteroderidae (such as *Rostochiensis*, *Globodera pallida*, and *Meloidogyne chitwoodi*); Hoplolaimidae (such as *Rotylenchulus reniformis*); Anguinidae (such as *Nothotylenchus acris* and *Ditylenchus dipsaci*); Tylenchulidae (such as *Tylenchulus semipenetrans*); Longidoridae (such as *Xiphinema index*); Trichodoridae; and Parasitaphelenchidae (such as *Bursaphelenchus xylophilus*).

[0379] Harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes can also refer to harmful insects, harmful mites and other harmful arthropods, harmful mollusks and harmful nematodes whose sensitivity to pesticides, acaricides, molluscicides or nematicides has decreased or who have strong resistance to pesticides.

[0380] As a method for controlling harmful arthropods according to the present invention, it can be implemented by directly applying an effective amount of the compound or composition A of the present invention to the harmful arthropods and / or to their habitats (plants, soil, houses, animals, etc.). Examples of methods for controlling harmful arthropods according to the present invention include foliar treatment, soil treatment, root treatment, spraying treatment, fumigation treatment, water surface treatment, and seed treatment.

[0381] For the compound or composition A of this invention, it is typically mixed with non-activated carriers such as solid carriers, liquid carriers, and gaseous carriers, and surfactants, and formulation adjuvants such as binders, dispersants, and stabilizers are added as needed to formulate it into aqueous suspensions, oil suspensions, oils, emulsions, microemulsions, microcapsules, wettable powders, water-dispersible granules, powders, granules, tablets, aerosols, resin formulations, etc. It is not limited to these formulations and can be formulated into the formulations described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271~276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.

[0382] These formulations typically contain 0.0001 to 99% by weight of the compound or composition A of the present invention.

[0383] Examples of solid carriers include clay (pyrophyllite clay, kaolinite clay, etc.), talc, calcium carbonate, diatomite, zeolite, bentonite, acid clay, palygorskite, silica, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.) in powder and granular form, as well as resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0384] 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.).

[0385] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0386] 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.).

[0387] Examples of adjuvants used in other formulations include binders, dispersants, colorants, and stabilizers. Specifically, 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.

[0388] In addition, adjuvants may be used as components to enhance or assist the efficacy of the compounds of the present invention. 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).

[0389] In this invention, the plant can be categorized as the whole plant, stem and leaves, flower, spike, fruit, trunk, branch, crown, seed, vegetative reproductive organs, and seedling.

[0390] 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 (including leaves and stems, rootless shoots) of plants such as sweet potatoes and Japanese yam. Bulbs, corms, tubers, rhizomes, stem cuttings, rhizophores, or tuberous roots are collectively referred to as bulbils. Potato cultivation begins by planting tubers in the soil, but the tubers used are usually called seed tubers.

[0391] As a method for controlling harmful arthropods by applying an effective amount of the compound or composition A of the present invention to the soil, examples include applying an effective amount of the compound or composition A of the present invention to the soil before or after transplanting. More specifically, examples include planting hole treatment (planting hole distribution, planting hole treatment soil mixing), root treatment (root distribution, root soil mixing, root irrigation, late seedling stage root treatment), planting furrow treatment (planting furrow distribution, planting furrow soil mixing), ridge furrow treatment (ridge furrow distribution, ridge furrow soil mixing, growing season ridge furrow distribution), sowing furrow treatment (sowing season ridge furrow distribution, sowing season ridge furrow soil mixing), overall treatment (whole soil distribution, whole soil mixing), ridge planting side treatment, water surface treatment (water surface application, water surface application after water storage), other soil distribution treatments (growing season granule foliar distribution, distribution under the canopy or around the trunk, soil surface distribution, soil surface mixing, planting 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).

[0392] As seed treatment, examples include treatment of seeds or vegetative reproductive organs by the compound or composition A of the present invention. More specifically, examples include: spraying treatment by atomizing a suspension of the compound or composition A of the present invention and spraying it onto the surface of the seed or vegetative reproductive organ; coating treatment by applying the compound or composition A of the present invention onto the seed or vegetative reproductive organ; immersion treatment by immersing the seed or vegetative reproductive organ in a solution of the compound or composition A of the present invention for a certain period of time; and methods of coating seeds or vegetative reproductive organs using a carrier containing the compound or composition A of the present invention (coating treatment, granule coating treatment, etc.). Seed potatoes are a particularly good example of the aforementioned vegetative reproductive organ.

[0393] When treating seeds or vegetative reproductive organs with composition A, composition A can be formulated as a single preparation for treating the seeds or vegetative reproductive organs, or composition A can be formulated as multiple different preparations for treating the seeds or vegetative reproductive organs multiple times. Examples of methods for treating seeds or vegetative reproductive organs multiple times with multiple different preparations include: treating with a preparation containing only the compound of the present invention as an active ingredient, air-drying the seeds or vegetative reproductive organs, and then treating with a preparation containing this ingredient; and treating with a preparation containing both the compound of the present invention and this ingredient as active ingredients, air-drying the seeds or vegetative reproductive organs, and then treating with a preparation containing this ingredient other than the ingredient that has been treated.

[0394] In this invention, a seed or vegetative reproductive organ that retains the compound or composition A of the present invention refers to a seed or vegetative reproductive organ in which the compound or composition A of the present invention is attached to its surface. For the aforementioned seed or vegetative reproductive organ that retains the compound or composition A of the present invention, materials other than the compound or composition A of the present invention may be attached before or after the compound or composition A of the present invention is attached to the seed or vegetative reproductive organ.

[0395] 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.

[0396] Seeds or vegetative reproductive organs containing the compound or composition A of the present invention can be obtained, for example, by applying a preparation containing the compound or composition A of the present invention to the seed or vegetative reproductive organ using the aforementioned seed treatment method.

[0397] When the compound or composition A of the present invention is used for the control of harmful arthropods in the agricultural field, the application rate is per 10,000 m³. 2 The amount of the compound of the present invention is typically 1 to 10,000 g. When treating seeds or vegetative reproductive organs, the amount of the compound of the present invention applied is typically in the range of 0.001 to 100 g relative to 1 kg of seeds or vegetative reproductive organs. When the compound or composition A of the present invention is formulated as an emulsion, wettable powder, suspension, etc., it is typically diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm and then applied. Granules, powders, etc., are typically applied directly.

[0398] In addition, the compound or composition A of the present invention can also be processed by methods such as wrapping the processed resin preparation into sheet or thread form around the crop, laying it near the crop, or laying it in the soil around the roots.

[0399] When using the compound or composition A of the present invention to control harmful arthropods inhabiting houses, the dosage, when applied to a surface, is [amount] per 1m². 2 The amount of the compound of the present invention applied to the treatment area is typically 0.01 to 1000 mg, and in the case of treatment in a space, it is applied per 1 m². 3 The amount of the compound of the present invention used in the treatment space is typically 0.01 to 500 mg. When the compound or composition A of the present invention is formulated as an emulsion, wettable powder, suspension, etc., it is usually diluted with water and applied in a manner that the concentration of the active ingredient is 0.1 to 10,000 ppm. Oils, aerosols, fumigants, poison baits, etc., are applied directly.

[0400] When using the compound or composition A of the present invention to control external parasites in livestock such as cattle, horses, pigs, sheep, goats, and chickens, as well as small animals such as dogs, cats, rats, and mice, it can be administered to animals using methods known in veterinary medicine. Specifically, for systemic suppression, it can be administered via methods such as tablets, feed mixing, suppositories, or injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). For non-systemic suppression, it can be used via methods such as spraying, pouring, or dripping an oily or aqueous solution, washing the animal with a shampoo, or making a collar or ear tag from a resin preparation for the animal to wear. The amount of the compound or composition A of the present invention administered to the animal is generally in the range of 0.1 to 1000 mg relative to 1 kg of the animal's body weight.

[0401] The compound or composition A of the present invention can be used as a control agent for harmful arthropods in farmland such as dry fields, paddy fields, lawns, and orchards. Examples of plants that can be cited as examples include the following.

[0402] Maize (dent, flint, soft, popcorn, glutinous, sweet, non-sweet maize), Rice (long-grain, short-grain, medium-grain, Japanese (japonica), tropical Japanese, Indian (indica), Javanese, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), Wheat (bread wheat (dull, soft, medium, red, white), durum wheat, spelt wheat, dense-eared wheat, each winter wheat type, spring wheat type), Barley (two-row barley (=brewing barley), six-row barley, naked barley, sticky barley, each...) Winter barley type, spring barley type), rye (winter rye type, spring rye type), black wheat (winter black wheat type, spring black wheat type), oats (winter oat type, spring oat type), sorghum, cotton (land-grown variety, Pima variety), soybean (mature seed harvest variety, edamame variety, green-harvested variety, each with indeterminate, determinate, and semi-determinate growth types), peanut, buckwheat, sugar beet (for sugar production, feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), Canada rapeseed (winter Canada rapeseed type, spring Canada rapeseed type), sunflower (for oil extraction, food). Vegetables used for both medicinal and ornamental purposes include sugarcane, tobacco, tea trees, mulberries, nightshade vegetables (eggplant, tomato, green pepper, chili pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, cantaloupe, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, bok choy, mustard greens, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, chrysanthemum, artichoke, lettuce, etc.), lilyaceous vegetables (scallions, onions, garlic, asparagus, etc.), umbelliferous vegetables (carrots, parsley, celery, parsnips, etc.), chenopodiaceae vegetables (spinach, sauvignon Blanc, etc.), and lamiaceae vegetables (perilla, mint). Basil, strawberries, sweet potatoes, Japanese yam, taro, pears (apples, European pears, Japanese pears, white pears, quince, quince, etc.), stone fruits (peach, plum, nectarine, green plum, cherry, apricot, plum, etc.), citrus fruits (Wenzhou mandarin oranges, oranges, lemons, limes, grapefruits, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates, coconuts, ornamental plants, forest plants, turfgrass, and pasture grasses.

[0403] The above-mentioned plants are any commonly cultivated varieties, without any particular limitation. These plants also include plants produced through natural mating, plants produced through mutation, F1 hybrids, and recombinant crops. Examples of recombinant crops include, for instance, plants conferred resistance to herbicides such as isoxaflutole (HPPD inhibitors, such as 4-hydroxyphenylpyruvate dioxygenase), imidazoline, thifensulfuron-methyl (ALS inhibitors, such as ALS inhibitors, such as acetolactate synthase), EPSP (5-enolpyruvate-shikimate-3-phosphate synthase), glutamine synthase inhibitors, PPO (protoporphyrinogen oxidase) 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.

[0404] Example The present invention will be described in more detail below using manufacturing examples, formulation examples, and test examples, but the present invention is not limited to these examples.

[0405] In this specification, Me represents methyl, Et represents ethyl, Boc represents tert-butyloxycarbonyl, and Cbz represents benzyloxycarbonyl.

[0406] First, examples of manufacturing the compounds of the present invention and their manufacturing intermediates are shown.

[0407] When the physical properties of a compound are determined using liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] is recorded. + Or [MH] - Retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows.

[0408] [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 35 mm, particle size 3 μm (General Incorporated Chemical Substances Evaluation and Research Organization) UV measurement wavelength: 252nm Mobile phase: Solution A: 0.1% formic acid aqueous solution; Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Gradient conditions: The solution is delivered using the concentration gradient described in [Table LC1].

[0409] [Table 1] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) Ionization methods: DUIS method (ESI, APCI) Reference Manufacturing Example 1 0.50 g of [(1S)-1-(5-amino-1H-pyrazol-3-yl)ethyl](methyl)carbamate tert-butyl ester, prepared according to the method described in Example 1-1 of Japanese Patent Application Publication No. 2018-76234, was mixed with 0.41 g of 1,1,3,3-tetramethoxypropane and 8.3 mL of acetic acid, and stirred under reflux for 3 hours. The reaction mixture was cooled to room temperature, and 0.46 g of N-iodosuccinimide was added, followed by further stirring for 16 hours. The resulting mixture was then injected into an ice-cooled saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The resulting organic layer was washed successively with a saturated aqueous solution of sodium thiosulfate, water, and saturated brine. The resulting organic layer was dried with sodium sulfate and concentrated.

[0410] To the residue obtained, 0.52 g of 2-(tributyltinyl)pyrimidine, 0.16 g of tetra(triphenylphosphine)palladium, 0.05 g of copper iodide (I), 0.06 g of lithium chloride, and 7.1 mL of 1,4-dioxane were added, and the mixture was stirred at 100 °C for 12 hours. The resulting mixture was cooled to room temperature, water was added, and extraction was performed using chloroform. The resulting organic layer was washed successively with water and saturated brine. The resulting organic layer was dried with sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 0.13 g of intermediate 1 as shown in the following formula.

[0411] [Chemical Formula 68] Intermediate 1: 1 H-NMR (CDCl3) δ: 8.87(2H, d), 8.74(1H, d), 8.71(1H, dd), 7.11(1H, s), 6.93(1H, t), 6.51-6.40(1H, m), 2.84-2.67(3H, m), 1.65(3H, d), 1.40-1.33(9H, m). Reference Manufacturing Example 2 A mixture of 2.79 g of ethyl 3-bromoimidazolo[1,2-b]pyridazine-2-carboxylate and 6.0 mL of THF was prepared according to the method described in Example 5 of International Publication No. 2016 / 020786. 12.0 mL of a 1 mol / L sodium hydroxide aqueous solution was added, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was then neutralized by adding 1 mol / L hydrochloric acid under ice-cooling conditions. The precipitated solid was filtered off and dried under reduced pressure to obtain 2.44 g of intermediate 2 as shown in the following formula.

[0412] [Chemical Formula 69] Intermediate 2: 1 H-NMR (DMSO-D6) δ: 8.78 (1H, d), 8.26 (1H, d), 7.46-7.44 (1H,m). Reference Manufacturing Example 3 To a mixture of 0.56 g of intermediate 2 and 7.7 mL of DMF, 2.1 mL of N,N-diisopropylethylamine, 2.64 g of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, and 0.29 g of N,O-dimethylhydroxylamine hydrochloride were added sequentially, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.63 g of intermediate 3.

[0413] [Chemical Formula 70] Intermediate 3: 1 H-NMR (CDCl3) δ: 8.53-8.52 (1H, m), 8.00-7.98 (1H, m), 7.20-7.17 (1H, m), 3.81 (3H, s), 3.48 (3H, s). Refer to manufacturing example 4 A mixture of 0.50 g of intermediate 3, 0.71 g of 2-(tributyltinyl)pyrimidine, 0.21 g of tetra(triphenylphosphine)palladium (0), 0.07 g of copper iodide (I), 0.07 g of lithium chloride, and 5.8 mL of 1,4-dioxane was stirred at 100 °C for 18 hours. The resulting mixture was cooled to room temperature, concentrated under reduced pressure, and then dissolved in chloroform. After filtration through diatomaceous earth, the resulting solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.13 g of intermediate 4.

[0414] [Chemical Formula 71] Intermediate 4: 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.65 (1H, dd), 8.10 (1H, dd), 7.25-7.22 (2H, m), 3.55 (3H, s), 3.41 (3H, s). Reference Manufacturing Example 5 To a mixture of 0.13 g of intermediate 4 and 4.6 mL of THF, 0.24 mL of methylmagnesium chloride (3.0 mol / L THF solution) was added under ice-cooling, and the mixture was stirred for 3 hours under ice-cooling. A saturated aqueous solution of ammonium chloride was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried using sodium sulfate, filtered, and concentrated to obtain 0.11 g of intermediate 5.

[0415] [Chemical Formula 72] Intermediate 5: 1 H-NMR (CDCl3) δ: 8.99 (2H, d), 8.45 (1H, dd), 8.11 (1H, dd), 7.43 (1H, t), 7.21 (1H, dd), 2.74 (3H, s). Reference Manufacturing Example 6 A mixture of 0.11 g of intermediate 5, 0.36 g of ammonium acetate, and 9.2 mL of methanol was stirred at 65 °C for 2 hours. After cooling the resulting mixture to room temperature, 0.087 g of sodium cyanoborohydride and 0.1 mL of acetic acid were added, and the mixture was stirred at 65 °C for 2 hours. After cooling the resulting mixture to room temperature, water and chloroform were added for extraction. The aqueous layer was adjusted to pH 12 by adding 3 mol / L sodium hydroxide solution, and then extracted with chloroform. The resulting organic layer was dried over sodium sulfate, filtered, and concentrated to give 0.058 g of intermediate 6.

[0416] [Chemical Formula 73] Intermediate 6: 1H-NMR (CDCl3) δ: 8.96 (2H, d), 8.53 (1H, dd), 8.04 (1H, dd), 7.25 (1H, m), 7.17 (1H, dd), 4.81 (1H, m), 1.61 (3H, d). Refer to manufacturing example 7 To a mixture of 1.12 g of intermediate 5, 1.26 mL of titanium ethoxide (IV), and 30 mL of methanol, 1.42 mL of methylamine (approximately 40% methanol solution) was added, and the mixture was stirred at 40 °C for 2 hours. The resulting mixture was cooled to room temperature, and 0.175 g of sodium borohydride was added, followed by stirring at room temperature for 2 hours. The resulting mixture was then injected into ice water, and extraction was performed with ethyl acetate. The aqueous layer was adjusted to pH 12 by adding 1 mol / L sodium hydroxide solution, and extraction was performed using chloroform. The resulting organic layer was dried with sodium sulfate and concentrated to give 0.573 g of intermediate 7 as shown in the formula below.

[0417] [Chemical Formula 74] Intermediate 7: 1 H-NMR (CDCl3) δ: 8.96 (2H, d), 8.55-8.52 (1H, m), 8.03 (1H,dd), 7.34 (1H, s), 7.25 (1H, t), 7.16 (1H, dd), 4.64 (1H, q), 2.29 (3H, s),1.55 (3H, d). Reference Manufacturing Example 8 To a mixture of 6.11 g of N,O-dimethylhydroxylamine hydrochloride and 120 mL of THF, 35 mL of trimethylaluminum (15% toluene solution) was added dropwise under ice-cooling, and the mixture was stirred for 30 minutes under ice-cooling. To the reaction mixture, 4.00 g of a mixture of pyrazolo[1,5-a]pyrimidine-2-carboxylate and 30 mL of THF was added, and the mixture was heated to room temperature and stirred for 2 hours. The resulting mixture was injected into 1 mol / L hydrochloric acid and extracted with chloroform. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 1.56 g of intermediate 8 as shown below.

[0418] [Chemical Formula 75] Intermediate 8: 1H-NMR (CDCl3) δ: 8.74-8.73 (1H, m), 8.56 (1H, dd), 7.19 (1H,d), 6.93 (1H, dd), 3.79 (3H, s), 3.49 (3H, s). Reference Manufacturing Example 9 The following shows the compound and its physical properties manufactured using intermediate 8 instead of intermediate 4 in accordance with Reference Manufacturing Example 5.

[0419] [Chemical Formula 76] Intermediate 9: 1 H-NMR (CDCl3) δ: 8.71-8.69 (1H, m), 8.57 (1H, dd), 7.20 (1H,m), 6.96 (1H, dd), 2.73 (3H, s). Reference Manufacturing Example 10 The following shows the compound and its physical properties manufactured using intermediate 9 instead of intermediate 5 in accordance with Reference Manufacturing Example 6.

[0420] [Chemical Formula 77] Intermediate 10: 1 H-NMR (CDCl3) δ: 8.61-8.60 (1H, m), 8.44 (1H, dd), 6.77 (1H,dd), 6.61 (1H, s), 4.36 (1H, q), 1.55 (3H, d). Reference Manufacturing Example 11 To a mixture of 0.058 g of intermediate 10 and 3.0 mL of DMF, 0.32 mL of N,N-diisopropylethylamine and 0.099 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.052 g of intermediate 11 as shown below.

[0421] [Chemical Formula 78] Intermediate 11: 1H-NMR (CDCl3) δ: 8.65-8.63 (1H, m), 8.50 (1H, dd), 8.29 (2H,s), 8.02 (1H, s), 7.12-7.10 (1H, m), 6.84 (1H, dd), 6.66 (1H, s), 5.65-5.58(1H, m), 1.75 (3H, d). Reference Manufacturing Example 12 Add 2.0 mL of acetic acid, 2.0 mL of chloroform, and 0.325 g of N-iodosuccinimide to 0.485 g of intermediate 11, and stir at room temperature for 5 hours. Add water to the resulting mixture and extract with chloroform. Wash the resulting organic layer successively with saturated sodium bicarbonate aqueous solution, saturated sodium thiosulfate aqueous solution, water, and saturated brine. Dry the resulting organic layer with sodium sulfate, filter, and concentrate. Spray the residue onto silica gel column chromatography to give 0.500 g of intermediate 12 as shown in the formula below.

[0422] [Chemical Formula 79] Intermediate 12: 1 H-NMR (CDCl3) δ: 8.63 (1H, dd), 8.59 (1H, dd), 8.30 (2H, s), 8.03 (1H, s), 7.20 (1H, d), 6.92 (1H, dd), 5.68-5.60 (1H, m), 1.73 (3H, d). Refer to manufacturing example 13-1 To 18.7 g of cyanoacetic acid, 293 mL of acetonitrile, 61.3 mL of triethylamine, and 55.9 g of magnesium chloride were added sequentially, and the mixture was stirred at room temperature for 23 hours to obtain mixture A. To a mixture of 34.8 g of N-methyl-N-(benzyloxycarbonyl)-L-alanine and 200 mL of THF, 28.5 g of 1,1'-carbonyldiimidazole and 3.58 g of 4-dimethylaminopyridine were added sequentially, and the mixture was stirred at room temperature for 4 hours to obtain mixture B. Mixture B was added dropwise to mixture A, and the mixture was stirred at room temperature for 44 hours. 1 mol / L hydrochloric acid was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed sequentially with water, saturated sodium bicarbonate aqueous solution, and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated to obtain 27.8 g of intermediate 13-1 as shown in the following formula.

[0423] [Chemical Formula 80] Intermediate 13-1: LCMS: 259 [MH] - RT=1.65 minutes Refer to manufacturing example 13-2 22.8 g of intermediate 13-1 was added to a mixture of 175 mL of ethanol, 175 mL of acetic acid, and 12.8 mL of hydrazine monohydrate, and stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed successively with saturated sodium bicarbonate aqueous solution and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated to obtain 22.0 g of intermediate 13-2 as shown in the formula below.

[0424] [Chemical Formula 81] Intermediate 13-2: LCMS: 275 [M+H] + RT=1.17 minutes Reference Manufacturing Example 14 A mixture of 22.0 g of intermediate 13, 15.8 mL of 1,1,3,3-tetramethoxypropane, and 40.1 mL of acetic acid was stirred at 90 °C for 5 hours. The resulting mixture was cooled to room temperature and concentrated. A saturated aqueous solution of sodium bicarbonate was added to the residue, and extraction was performed using ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 11.6 g of intermediate 14 as shown below.

[0425] [Chemical Formula 82] Intermediate 14: 1 H-NMR (CDCl3) δ: 8.64-8.62 (1H, m), 8.45 (1H, dd), 7.41-7.33(5H, m), 6.78 (1H, dd), 6.58-6.53 (1H, m), 5.81-5.67 (1H, m), 5.25-5.17 (2H,m), 2.79 (3H, s), 1.64 (3H, d). Reference Manufacturing Example 15 20 mL of chloroform and 4.80 g of N-iodosuccinimide were added to 6.30 g of intermediate 14, and the mixture was stirred at room temperature for 6 hours. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed successively with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium thiosulfate solution, water, and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 6.61 g of intermediate 15 as shown in the formula below.

[0426] [Chemical Formula 83] Intermediate 15: 1 H-NMR (CDCl3) δ: 8.61-8.59 (1H, m), 8.54 (1H, dd), 7.42-7.30(5H, m), 6.85 (1H, dd), 5.80-5.61 (1H, m), 5.25-5.23 (2H, m), 2.75-2.69 (3H,m), 1.65 (3H, d). Reference Manufacturing Example 16 The following shows the compound and its physical properties manufactured using intermediate 15 instead of intermediate 3 in accordance with Reference Manufacturing Example 4.

[0427] [Chemical Formula 84] Intermediate 16: 1 H-NMR (CDCl3) δ: 8.75-8.74 (1H, m), 8.69-8.64 (3H, m), 7.33-7.31 (5H, m), 6.99 (1H, t), 6.95-6.93 (1H, m), 6.58-6.53 (1H, m), 5.12-5.09(2H, m), 2.81-2.76 (3H, m), 1.68 (3H, d). Reference Manufacturing Example 17 Add 5 mL of trifluoroacetic acid to 0.44 g of intermediate 16 and stir at 70 °C for 3 hours. Cool the reaction mixture to room temperature and concentrate. Add 1 mol / L hydrochloric acid to the residue and extract with methyl tert-butyl ether. Adjust the pH to 10 by adding 1 mol / L sodium hydroxide aqueous solution to the resulting aqueous layer and extract with chloroform. Dry the resulting organic layer with sodium sulfate, filter, and concentrate to obtain 0.226 g of intermediate 17 as shown in the formula below.

[0428] [Chemical Formula 85] Intermediate 17: 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.77-8.76 (1H, m), 8.73-8.71(1H, m), 7.14 (1H, t), 6.94 (1H, dd), 4.72 (1H, q), 2.36 (3H, s), 1.55 (3H,d). Reference Manufacturing Example 18 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 14 using acetylacetone instead of 1,1,3,3-tetramethoxypropane.

[0429] [Chemical Formula 86] Intermediate 18: 1 H-NMR (CDCl3) δ: 7.39-7.31 (5H, m), 6.52 (1H, s), 6.41 (1H,s), 5.78-5.65 (1H, m), 5.21 (2H, s), 2.79 (3H, s), 2.70 (3H, s), 2.54 (3H,s), 1.62 (3H,d). Refer to manufacturing example 19 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 14 using 2-chloromalondialdehyde instead of 1,1,3,3-tetramethoxypropane.

[0430] [Chemical Formula 87] Intermediate 19: 1 H-NMR (CDCl3) δ: 8.67-8.65 (1H, m), 8.39 (1H, d), 7.39-7.34(5H, m), 6.61-6.55 (1H, m), 5.79-5.63 (1H, m), 5.21 (2H, s), 2.79-2.77 (3H,m), 1.62 (3H, d). Reference Manufacturing Example 20 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 14 using 1,1,3,3-tetraethoxy-2-methylpropane instead of 1,1,3,3-tetramethoxypropane.

[0431] [Chemical Formula 88] Intermediate 20:1 H-NMR (CDCl3) δ: 8.42 (1H, s), 8.33 (1H, d), 7.39-7.32 (5H,m), 6.52-6.47 (1H, m), 5.77-5.70 (1H, m), 5.21 (2H, s), 2.77 (3H, s), 2.36 (3H, s), 1.62 (3H, d). Refer to manufacturing example 21 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 14 using 1-dimethylamino-1-buten-3-one instead of 1,1,3,3-tetramethoxypropane.

[0432] [Chemical Formula 89] Intermediate 21: 1 H-NMR (CDCl3) δ: 8.34 (1H, d), 7.37-7.32 (5H, m), 6.65-6.64(1H, m), 6.56-6.52 (1H, m), 5.81-5.68 (1H, m), 5.21 (2H, s), 2.82-2.80 (3H, m), 2.75 (3H, s), 1.64 (3H, d). Refer to manufacturing example 22 The following shows the compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 15 using intermediate 18, intermediate 19, intermediate 20 or intermediate 21 instead of intermediate 14.

[0433] [Chemical Formula 90] In the compound shown in formula (B-1), R 3q1 R 3q2 and R 3q3 The combination is any combination of compounds listed in [Table B-1].

[0434] [Table 2] Intermediate 22: 1 H-NMR (CDCl3) δ: 7.40-7.32 (5H, m), 6.57 (1H, s), 5.75-5.62(1H, m), 5.25-5.20 (2H, m), 2.76-2.71 (6H, m), 2.61 (3H, s), 1.63 (3H, d). Intermediate 23:1 H-NMR (CDCl3) δ: 8.67-8.63 (1H, m), 8.46 (1H, d), 7.40-7.34(5H, m), 5.72-5.61 (1H, m), 5.23-5.21 (2H, m), 2.75-2.72 (3H, m), 1.63-1.62(3H, m). Intermediate 24: 1 H-NMR (CDCl3) δ: 8.40 (2H, s), 7.38-7.33 (5H, m), 5.76-5.61(1H, m), 5.25-5.22 (2H, m), 2.73-2.70 (3H, m), 2.39 (3H, s), 1.63 (3H, d). Intermediate 25: 1 H-NMR (CDCl3) δ: 8.44 (1H, d), 7.42-7.30 (5H, m), 6.71 (1H,d), 5.81-5.62 (1H, m), 5.26-5.17 (2H, m), 2.80-2.77 (3H, m), 2.76-2.74 (3H,m), 1.65 (3H, d). Refer to manufacturing example 23 The following shows the compounds manufactured according to Reference Manufacturing Example 4 and their physical properties.

[0435] [Chemical Formula 91] In the compound shown in formula (B-2), R 3q1 R 3q2 and R 3q3 The combination is any combination of compounds listed in [Table B-2].

[0436] [Table 3] Intermediate 26: 1 H-NMR (CDCl3) δ: 8.68-8.59 (2H, m), 7.34-7.30 (5H, m), 6.96-6.94 (1H, m), 6.67-6.65 (1H, m), 6.55-6.42 (1H, m), 5.12-5.10 (2H, m), 2.81-2.76 (3H, m), 2.75-2.73 (3H, m), 2.68 (3H, s), 1.67 (3H, d). Intermediate 27: 1 H-NMR (CDCl3) δ: 8.76-8.61 (4H, m), 7.33-7.31 (5H, m), 7.02(1H, t), 6.52 (1H, q), 5.10-5.07 (2H, m), 2.83-2.78 (3H, m), 1.67 (3H, d). Intermediate 28: 1 H-NMR (CDCl3) δ: 8.71-8.70 (1H, m), 8.61-8.59 (2H, m), 8.51-8.49 (1H, m), 7.31-7.30 (5H, m), 6.96 (1H, t), 6.54-6.51 (1H, m), 5.14-5.11(2H, m), 2.79-2.74 (3H, m), 2.42 (3H, d), 1.67 (3H, d). Intermediate 29: 1 H-NMR (CDCl3) δ: 8.73-8.72 (1H, m), 8.64-8.63 (2H, m), 7.32-7.26 (5H, m), 6.98 (1H, t), 6.81-6.79 (1H, m), 6.61-6.54 (1H, m), 5.16-5.08(2H, m), 2.87-2.82 (6H, m), 1.69 (3H, d). Refer to manufacturing example 24 The following shows the compounds manufactured according to Reference Manufacturing Example 17 and their physical properties.

[0437] [Chemical Formula 92] In the compound shown in formula (B-3), R 3q1 R 3q2 and R 3q3 The combination is any combination of compounds listed in [Table B-3].

[0438] [Table 4] Intermediate 30: 1H-NMR (CDCl3) δ: 8.85 (2H, d), 7.09 (1H, t), 6.67-6.67 (1H,m), 4.62 (1H, q), 2.79-2.78 (3H, m), 2.69 (3H, s), 2.36 (3H, s), 1.53 (3H,d). Intermediate 31: 1 H-NMR (CDCl3) δ: 8.91 (2H, d), 8.76 (1H, d), 8.69 (1H, d), 7.18 (1H, t), 4.75 (1H, q), 2.38 (3H, s), 1.57 (3H, d). Intermediate 32: 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.64-8.63 (1H, m), 8.51-8.51(1H, m), 7.12 (1H, t), 4.70 (1H, q), 2.43-2.43 (3H, m), 2.36 (3H, s), 1.56(3H, d). Intermediate 33: 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.65 (1H, d), 7.11 (1H, t), 6.81-6.80 (1H, m), 4.70 (1H, q), 2.85-2.85 (3H, m), 2.38 (3H, s), 1.56 (3H,d). Refer to manufacturing example 25 10 mL of ethanol and 5.19 g of methyl 2-chloro-3-oxovalerate were added to 2.00 g of 3-aminopyridazine, and the mixture was stirred at 80 °C for 8 hours. The reaction solution was cooled to room temperature and concentrated. The residue was subjected to silica gel column chromatography to give 0.473 g of intermediate 34 as shown in the formula below.

[0439] [Chemical Formula 93] Intermediate 34: 1 H-NMR (CDCl3) δ: 8.55 (1H, dd), 7.98 (1H, dd), 7.21 (1H,dd), 4.02 (3H, s), 3.17 (2H, q), 1.38 (3H, t). Refer to manufacturing example 26 0.473 g of intermediate 34 was added to 15 mL of chloroform, 0.038 g of 2,2'-azobis(isobutyronitrile), and 0.491 g of N-bromosuccinimide, and stirred at 65 °C for 5 hours. The reaction mixture was cooled to room temperature, and a saturated aqueous solution of sodium thiosulfate was added. Extraction was performed using chloroform. The resulting organic layer was washed successively with a saturated aqueous solution of sodium bicarbonate and a saturated brine solution, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.475 g of intermediate 35 as shown in the formula below.

[0440] [Chemical Formula 94] Intermediate 35: 1 H-NMR (CDCl3) δ: 8.59 (1H, dd), 8.07 (1H, dd), 7.27 (1H,dd), 6.10 (1H, q), 4.06 (3H, s), 2.19 (3H, d). Refer to manufacturing example 27 Add 1 mL of methanol and 0.505 mL of methylamine (approximately 40% methanol solution) to 0.237 g of intermediate 35, and stir at room temperature for 30 hours. Concentrate the reaction solution to obtain 0.241 g of intermediate 36 as shown in the formula below.

[0441] [Chemical Formula 95] Intermediate 36: 1 H-NMR (CDCl3) δ: 8.54 (1H, dd), 8.13 (1H, dd), 7.31 (1H,dd), 4.79 (1H, q), 3.49 (1H, s), 3.11 (3H, d), 2.50 (3H, s), 1.72 (3H, d). Reference Manufacturing Example 28 70 mL of THF, 9.6 mL of triethylamine, and 7.44 mL of methanesulfonyl chloride were added sequentially to 5.00 g of ethyl 3,5-dihydroxybenzoate, and the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, and the solution was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 9.32 g of intermediate 37 as shown in the formula below.

[0442] [Chemical Formula 96] Intermediate 37: 1H-NMR (CDCl3) δ: 7.92 (2H, d), 7.47 (1H, t), 4.42 (2H, q), 3.23 (6H, s), 1.41 (3H, t). Refer to manufacturing example 29 To 3.00 g of methyl 3-bromo-5-hydroxybenzoate, 20 mL of THF, 2.0 mL of triethylamine, and 1.23 mL of methanesulfonyl chloride were added sequentially, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated to give 4.53 g of intermediate 38 as shown in the formula below.

[0443] [Chemical Formula 97] Intermediate 38: 1 H-NMR (CDCl3) δ: 8.16 (1H, t), 7.87 (1H, t), 7.66 (1H, t), 3.95 (3H, s), 3.22 (3H, s). Reference Manufacturing Example 30 To 1.00 g of methyl 3-bromo-5-iodobenzoate, 0.45 g of sodium cyclopropyl sulfinate, 0.055 g of copper iodide (I), 0.067 g of L-proline, 0.040 g of potassium carbonate, and 2.9 mL of DMSO were added, and the mixture was stirred at 115 °C for 7 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.287 g of intermediate 39 as shown in the formula below.

[0444] [Chemical Formula 98] Intermediate 39: 1 H-NMR (CDCl3) δ: 8.47 (1H, t), 8.42 (1H, dd), 8.21 (1H, t), 3.98 (3H, s), 2.52-2.48 (1H, m), 1.42-1.37 (2H, m), 1.13-1.07 (2H, m). Refer to manufacturing example 31 Add 5 mL of DMSO and 0.193 g of sodium hydride (60%, dispersed in liquid paraffin) to 0.495 g of methyl 3-bromo-5-(cyanomethyl)benzoate, and stir at room temperature for 15 minutes. Add 0.605 g of 1,2-dibromoethane to the reaction mixture, and stir further at room temperature for 7.5 hours. Add a saturated aqueous solution of ammonium chloride to the resulting mixture and extract with methyl tert-butyl ether. Wash the resulting organic layer with saturated brine, dry with magnesium sulfate, filter, and concentrate. Spread the residue to silica gel column chromatography to give 0.085 g of intermediate 40 as shown below.

[0445] [Chemical Formula 99] Intermediate 40: 1 H-NMR (CDCl3) δ: 8.10 (1H, t), 7.81 (1H, t), 7.70 (1H, t), 3.94 (3H, s), 1.82-1.80 (2H, m), 1.48-1.46 (2H, m). Refer to manufacturing example 32 Add 10 mL of THF and 5 mL of water to 1.00 g of intermediate 37, then add 0.186 g of lithium hydroxide monohydrate under ice cooling, and stir at room temperature for 30 minutes. Adjust the pH to 2 with hydrochloric acid, and extract with ethyl acetate. Wash the resulting organic layer with saturated brine, dry with sodium sulfate, filter, and concentrate to obtain 0.818 g of intermediate 41 as shown in the formula below.

[0446] [Chemical Formula 100] Intermediate 41: 1 H-NMR (CDCl3) δ: 7.98 (2H, d), 7.53 (1H, t), 3.25 (6H, s). Refer to manufacturing example 32-1 The following shows compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 32 using intermediate 38, intermediate 39 or intermediate 40 instead of intermediate 37.

[0447] [Chemical Formula 101] Intermediate 42: 1 H-NMR (CDCl3) δ: 8.21 (1H, t), 7.93 (1H, dd), 7.73 (1H, t), 3.24 (3H, s). [Chemical Formula 102] Intermediate 43: 1 H-NMR (CDCl3) δ: 8.52 (1H, t), 8.47 (1H, t), 8.25 (1H, t), 2.54-2.48 (1H, m), 1.42-1.40 (2H, m), 1.13-1.10 (2H, m). [Chemical Formula 103] Intermediate 44: 1 H-NMR (CDCl3) δ: 8.16 (1H, t), 7.87 (1H, t), 7.76 (1H, t), 1.85-1.81 (2H, m), 1.51-1.47 (2H, m). Reference Manufacturing Example 33 A mixture of 15 g of (S)-4-[N-(benzyloxycarbonyl)amino]-3-oxovalerate methyl ester, prepared according to the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108, and 107 mL of methanol was mixed with 5.59 g of acetamiprine hydrochloride, followed by 21.8 g of sodium methoxide (28% by weight methanol solution), and stirred at room temperature for 18 hours. The resulting mixture was concentrated, water was added, and chloroform was used for extraction. Citric acid was added to the resulting aqueous layer until pH 5 was reached, followed by chloroform extraction. The resulting organic layer was washed successively with water and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated to give 12.1 g of intermediate 45 as shown in the following formula.

[0448] [Chemical Formula 104] Intermediate 45: 1 H-NMR (CDCl3) δ: 7.36-7.32 (5H, m), 6.26 (1H, s), 5.51 (1H,d), 5.13-5.08 (2H, m), 4.69-4.64 (1H, m), 2.45 (3H, s), 1.41 (3H, d). Refer to manufacturing example 34 To a mixture of 5.0 g of intermediate 45 and 87 mL of THF, add 8.83 g of iodine and 5.04 g of potassium carbonate, and stir under reflux for 7 hours. Cool the resulting mixture to room temperature, add water, and extract with chloroform. Wash the resulting organic layer successively with a saturated aqueous solution of sodium thiosulfate, water, and saturated brine. Dry the resulting organic layer with sodium sulfate, filter, and concentrate to obtain 3.37 g of intermediate 46 as shown in the formula below.

[0449] [Chemical Formula 105] Intermediate 46: 1 H-NMR (CDCl3) δ: 7.36-7.32 (5H, m), 5.90 (1H, d), 5.19-5.11(3H, m), 2.47 (3H, s), 1.37 (3H, d). Reference Manufacturing Example 35 The following shows the compound and its physical properties manufactured using intermediate 46 instead of intermediate 3 in accordance with Reference Manufacturing Example 4.

[0450] [Chemical Formula 106] Intermediate 47: 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 7.33-7.31 (6H, m), 5.94-5.92(1H, m), 5.06-5.02 (2H, m), 4.81 (1H, s), 2.44 (3H, s), 1.37 (3H, d). Reference Manufacturing Example 36 To a mixture of 0.84 g of intermediate 47 and 4.6 mL of toluene, 0.64 mL of phosphoric acid chloride was added, and the mixture was stirred at 110 °C for 3 hours. The resulting mixture was cooled to room temperature, and a 1 mol / L sodium hydroxide aqueous solution was added. After stirring for 30 minutes, extraction was performed using chloroform. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.14 g of intermediate 48.

[0451] [Chemical Formula 107] Intermediate 48: 1H-NMR (CDCl3) δ: 8.92 (2H, d), 7.40 (1H, t), 7.37-7.31 (5H,m), 6.05 (1H, d), 5.06-5.04 (2H, m), 4.84-4.79 (1H, m), 2.76 (3H, s), 1.33(3H, d). Reference Manufacturing Example 37 Add 0.05 mL of hydrazine monohydrate to a mixture of 0.14 g of intermediate 48 and 3.5 mL of ethanol, and stir at room temperature for 15 hours. Add water to the resulting mixture, filter out the precipitated solid, and dry under reduced pressure to obtain 0.059 g of intermediate 49 as shown in the following formula.

[0452] [Chemical Formula 108] Intermediate 49: 1 H-NMR (CDCl3) δ: 8.84 (2H, d), 7.36-7.28 (5H, m), 7.22 (1H,t), 6.36 (1H, d), 5.69-5.67 (1H, m), 5.08-5.02 (2H, m), 4.15 (2H, d), 2.56(3H, s), 1.50(3H, d). Reference Manufacturing Example 38 To a mixture of 0.059 g of intermediate 49 and 3.2 mL of chloroform, add 0.05 mL of trimethyl orthoformate and 0.04 mL of trifluoroacetic acid, and stir at room temperature for 15 hours. Add a saturated aqueous solution of sodium bicarbonate to the resulting mixture and extract with chloroform. Wash the resulting organic layer successively with water and saturated brine. Dry the resulting organic layer with sodium sulfate, filter, and concentrate to obtain 0.065 g of intermediate 50.

[0453] [Chemical Formula 109] Intermediate 50: 1 H-NMR (CDCl3) δ: 9.00 (2H, d), 8.42 (1H, s), 7.40 (1H, t), 7.34-7.31 (5H, m), 5.95 (1H, d), 5.38-5.35 (1H, m), 5.06-5.01 (2H, m), 3.05(3H, s), 1.55(3H, d). Reference Manufacturing Example 39 To a mixture of 0.065 g of intermediate 50, 3.2 mL of ethyl acetate, and 1.6 mL of methanol, 0.07 g of 10% palladium / activated carbon (approximately 55% water) was added. The mixture was stirred at room temperature for 6 hours under a hydrogen atmosphere. The resulting mixture was filtered through diatomaceous earth, and the solution was concentrated under reduced pressure to obtain 0.13 g of intermediate 51.

[0454] [Chemical Formula 110] Intermediate 51: 1 H-NMR (CDCl3) δ: 8.99 (2H, d), 8.39 (1H, s), 7.40 (1H, t), 4.28 (1H, q), 3.07 (3H, s), 1.46 (3H, d). Reference Manufacturing Example 40 The following shows the compounds and their physical properties produced using formamidine acetate instead of acetamidine hydrochloride in accordance with Reference Manufacturing Example 33.

[0455] [Chemical Formula 111] Intermediate 52: 1 H-NMR (CDCl3) δ: 8.10 (1H, s), 7.36-7.30 (5H, m), 6.42 (1H,s), 5.40 (1H, d), 5.12-5.09 (2H, m), 4.69-4.67 (1H, m), 1.43 (3H, d). Refer to manufacturing example 41 To a mixture of 4.0 g of intermediate 52, 3.33 g of benzyltriethylammonium chloride, 1.84 mL of dimethylaniline, and 49 mL of acetonitrile, 2.04 mL of phosphoric acid chloride was added, and the mixture was stirred at 60 °C for 2 hours. The resulting mixture was cooled to room temperature, concentrated under reduced pressure, and then extracted with saturated sodium bicarbonate aqueous solution for 30 minutes. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 3.7 g of intermediate 53.

[0456] [Chemical Formula 112] Intermediate 53: 1H-NMR (CDCl3) δ: 8.93 (1H, s), 7.36-7.34 (6H, m), 5.60 (1H,d), 5.13-5.09 (2H, m), 4.89-4.84 (1H, m), 1.49 (3H, d). Refer to manufacturing example 42 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 37 using intermediate 53 instead of intermediate 48.

[0457] [Chemical Formula 113] Intermediate 54: 1 H-NMR (CDCl3) δ: 8.52 (1H, s), 7.36-7.31 (5H, m), 6.64 (1H,s), 6.24 (1H, s), 5.77 (1H, d), 5.12-5.10 (2H, m), 4.76-4.71 (1H, m), 3.81 (2H, s), 1.45 (3H, d). Refer to manufacturing example 43 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 38 using intermediate 54 instead of intermediate 49.

[0458] [Chemical Formula 114] Intermediate 55: 1 H-NMR (CDCl3) δ: 9.36 (1H, s), 8.42 (1H, s), 7.64 (1H, s), 7.35-7.34 (5H, m), 5.47 (1H, d), 5.13-5.07 (2H, m), 5.00-4.99 (1H, m), 1.54(3H, d). Refer to manufacturing example 44 2.90 g of N-bromosuccinimide was added to a mixture of 2.42 g of intermediate 55 and 16.3 mL of acetic acid, and the mixture was stirred at room temperature for 21 hours. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed successively with saturated aqueous sodium bicarbonate solution, saturated aqueous sodium thiosulfate solution, water, and saturated brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 1.66 g of intermediate 56 as shown in the formula below.

[0459] [Chemical Formula 115] Intermediate 56: 1 H-NMR (CDCl3) δ: 9.29 (1H, s), 8.45 (1H, s), 7.37-7.34 (5H,m), 5.79 (1H, d), 5.51-5.49 (1H, m), 5.13-5.06 (2H, m), 1.49 (3H, d). Refer to manufacturing example 45 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 4 using intermediate 56 instead of intermediate 3.

[0460] [Chemical Formula 116] Intermediate 57: 1 H-NMR (CDCl3) δ: 9.45 (1H, s), 9.01 (2H, d), 8.46 (1H, s), 7.43 (1H, t), 7.33-7.31 (5H, m), 5.82 (1H, d), 5.38-5.37 (1H, m), 5.05-4.99 (2H, m), 1.57 (3H, d). Refer to manufacturing example 46 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 39 using intermediate 57 instead of intermediate 50.

[0461] [Chemical Formula 117] Intermediate 58: LCMS: 242 [M+H] + RT=0.26 minutes Refer to manufacturing example 47 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 41 using intermediate 46 instead of intermediate 52.

[0462] [Chemical Formula 118] Intermediate 59: 1 H-NMR (CDCl3) δ: 7.36-7.32 (5H, m), 6.05 (1H, d), 5.31-5.27(1H, m), 5.13-5.10 (2H, m), 2.64 (3H, s), 1.42 (3H, d). Reference Manufacturing Example 48 To a mixture of 1.0 g of intermediate 59 and 11.6 mL of acetonitrile, 0.69 g of 2,4,6-trimethoxybenzylamine and 0.64 g of potassium carbonate were added, and the mixture was stirred at room temperature for 21 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 1.31 g of intermediate 60 as shown in the formula below.

[0463] [Chemical Formula 119] Intermediate 60: 1 H-NMR (CDCl3) δ: 7.36-7.31 (5H, m), 6.32 (1H, d), 6.16 (2H,s), 6.03-6.02 (1H, m), 5.12-5.09 (2H, m), 5.04-4.99 (1H, m), 4.69-4.62 (2H,m), 3.86 (6H, s), 3.82 (3H, s), 2.48 (3H, s), 1.35 (3H, d). Reference Manufacturing Example 49 Add 8.4 mL of hydrogen chloride (5-10 wt% methanol solution) to 0.50 g of intermediate 60 and stir at 90 °C for 15 hours. Cool the resulting mixture to room temperature and concentrate it by adding 4.2 mL of DMF, 4.2 mL of bromoacetaldehyde diacetal, and 1.0 mL of acetic acid, and stirring at 80 °C for 15 hours. Add water to the resulting mixture and extract with ethyl acetate. Wash the resulting organic layer successively with water and saturated brine. Dry the resulting organic layer with sodium sulfate, filter, and concentrate. Perform silica gel column chromatography on the residue to give 0.10 g of intermediate 61 as shown in the formula below.

[0464] [Chemical Formula 120] Intermediate 61: 1 H-NMR (CDCl3) δ: 7.73 (1H, d), 7.61 (1H, s), 7.36-7.32 (5H, m), 5.96 (1H, d), 5.41-5.36 (1H, m), 5.14-5.09 (2H, m), 2.79 (3H, s), 1.44(3H, d). Reference Manufacturing Example 50 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 4 using intermediate 61 instead of intermediate 3.

[0465] [Chemical Formula 121] Intermediate 62: 1 H-NMR (CDCl3) δ: 8.98 (2H, d), 7.72 (1H, d), 7.54 (1H, d), 7.37-7.37 (1H, m), 7.34-7.31 (5H, m), 6.00 (1H, d), 5.14-5.13 (1H, m), 5.05-5.03 (2H, m), 2.86 (3H, s), 1.49 (3H, d). Refer to manufacturing example 51 A mixture of 6.0 g of intermediate 56 and 31.9 mL of trifluoroacetic acid was stirred at 70 °C for 4 hours. The resulting mixture was cooled to room temperature and concentrated, then extracted with methyl tert-butyl ether and water. The resulting aqueous layer was adjusted to pH 10 by adding saturated sodium bicarbonate, and then extracted with chloroform (containing 20% ​​isopropanol by volume). The resulting organic layer was dried using sodium sulfate, filtered, and concentrated.

[0466] To a mixture of the obtained residue and 35.5 mL of THF, 10.0 mL of N,N-diisopropylethylamine and 5.94 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially under ice-cooling, and the mixture was stirred at room temperature for 4 hours. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 6.84 g of intermediate 63 as shown in the formula below.

[0467] [Chemical Formula 122] Intermediate 63: 1 H-NMR (CDCl3) δ: 9.38 (1H, s), 8.50 (1H, s), 8.27 (2H, s), 8.04 (1H, s), 7.34 (1H, d), 5.93-5.91 (1H, m), 1.65 (3H, d). Refer to manufacturing example 52 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 4, using intermediate 63 instead of intermediate 3, and using tributyl(1-ethoxyvinyl)stanane instead of 2-(tributylmethylstanyl)pyrimidine.

[0468] [Chemical Formula 123] Intermediate 64: 1 H-NMR (CDCl3) δ: 9.41 (1H, s), 8.44 (1H, s), 8.25 (2H, s), 8.02 (1H, s), 7.30 (1H, d), 5.87-5.84 (1H, m), 4.87 (1H, d), 4.81 (1H, d),4.13-4.09 (2H, m), 1.64 (3H, d), 1.45 (3H, t). Refer to manufacturing example 53 Add 23.9 g of 1,1'-carbonyldiimidazole to a mixture of 30 g of N-(tert-butoxycarbonyl)-N-methyl-L-alanine and 300 mL of chloroform, and stir at room temperature for 1 hour. Add 9.3 mL of malononitrile, stir further at room temperature for 4 hours, and concentrate the resulting mixture.

[0469] To the mixture of the obtained residue and 490 mL of 1,4-dioxane, 86 g of sodium carbonate and 56 mL of dimethyl sulfate were added sequentially, and the mixture was stirred at 85 °C for 8 hours. 28 mL of dimethyl sulfate was added, and the mixture was stirred for another 9 hours. Then, 28 mL of dimethyl sulfate and 24.7 g of sodium carbonate were added, and the mixture was stirred for another 3 hours. The resulting mixture was cooled to room temperature and filtered through a cotton plug. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried using sodium sulfate, filtered, and concentrated. The resulting residue was subjected to silica gel column chromatography to give 12.2 g of intermediate 65.

[0470] [Chemical Formula 124] Intermediate 65: 1 H-NMR (CDCl3) δ: 5.02-4.88 (1H, m), 4.36 (3H, s), 2.89 (3H,s), 1.48 (9H, s), 1.43 (3H, d). Refer to manufacturing example 54 To a mixture of 12.2 g of intermediate 65 and 50 mL of ethanol, 4.5 mL of hydrazine monohydrate was added sequentially, and the mixture was stirred at 60 °C for 8 hours. After cooling the resulting mixture to room temperature, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried using sodium sulfate, filtered, and concentrated.

[0471] Add 15 mL of 1,1,3,3-tetramethoxypropane and 50 mL of acetic acid to the residue, and stir at 80 °C for 6 hours. After cooling the mixture to room temperature, add a saturated aqueous sodium bicarbonate solution and extract with ethyl acetate. Wash the resulting organic layer successively with water and saturated brine. Dry the organic layer with sodium sulfate, filter, and concentrate. Perform silica gel column chromatography on the residue to give 10.0 g of intermediate 66.

[0472] [Chemical Formula 125] Intermediate 66: 1 H-NMR (CDCl3) δ: 8.71-8.69 (2H, m), 7.05 (1H, s), 5.77-5.67(1H, m), 2.83 (3H, s), 1.67 (3H, d), 1.51 (9H, s). Reference Manufacturing Example 66 The mixture of 0.30 g of intermediate 66 and 5.0 mL of hydrogen chloride / 1,4-dioxane solution (4 mol / L) was stirred at room temperature for 15 hours, and the resulting mixture was concentrated.

[0473] To the mixture of the obtained residue and 5.0 mL of THF, 0.37 mL of triethylamine and 0.27 mL of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.15 g of intermediate 78.

[0474] [Chemical Formula 126] Intermediate 78: 1 H-NMR (CDCl3) δ: 8.75-8.73 (2H, m), 8.08 (2H, s), 7.96 (1H,s), 7.13-7.11 (1H, m), 6.28 (1H, s), 3.04-2.93 (3H, m), 1.84 (3H, d). Reference Manufacturing Example 55 The following shows the compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 38, using intermediate 54 instead of intermediate 49 and trimethyl orthoacetate instead of trimethyl orthoformate.

[0475] [Chemical Formula 127] Intermediate 67: LCMS: 312 [M+H] + RT=1.44 minutes Reference Manufacturing Example 56 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 44 using intermediate 67 instead of intermediate 55.

[0476] [Chemical Formula 128] Intermediate 68: 1 H-NMR (CDCl3) δ: 9.15 (1H, s), 7.37-7.31 (5H, m), 5.81 (1H,d), 5.47-5.45 (1H, m), 5.13-5.07 (2H, m), 2.65 (3H, s), 1.47 (3H, d). Refer to manufacturing example 57 The following shows the compound and its physical properties manufactured using intermediate 68 instead of intermediate 3 in accordance with Reference Manufacturing Example 4.

[0477] [Chemical Formula 129] Intermediate 69: 1 H-NMR (CDCl3) δ: 9.32 (1H, s), 9.00 (2H, d), 7.41 (1H, t), 7.35-7.31 (5H, m), 5.84 (1H, d), 5.29-5.28 (1H, m), 5.05-5.00 (2H, m), 2.64(3H, s), 1.53(3H, d). Reference Manufacturing Example 58 A mixture of 1.0 g of intermediate 69 and 5.1 mL of trifluoroacetic acid was stirred at 70 °C for 4 hours. The resulting mixture was cooled to room temperature and concentrated, then extracted with methyl tert-butyl ether and water. The resulting aqueous layer was adjusted to pH 10 by adding saturated sodium bicarbonate, and then extracted with chloroform (containing 20% ​​isopropanol by volume). The resulting organic layer was dried with sodium sulfate, filtered, and concentrated to obtain 0.54 g of intermediate 70.

[0478] [Chemical Formula 130] Intermediate 70: 1H-NMR (CDCl3) δ: 9.35 (1H, s), 8.99 (2H, d), 7.41 (1H, t), 4.20 (1H, q), 2.63 (3H, s), 1.45 (3H, d). Reference Manufacturing Example 59 The following shows the compounds and their physical properties manufactured using the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108, methyl (S)-4-[N-(benzyloxycarbonyl)-N-methylamino]-3-oxovalerate instead of methyl (S)-4-[N-(benzyloxycarbonyl)amino]-3-oxovalerate, and formamidine acetate instead of acetamidine hydrochloride, in accordance with Reference Manufacturing Example 33.

[0479] [Chemical Formula 131] Intermediate 71: LCMS: 288 [M+H] + RT=1.35 minutes Reference Manufacturing Example 60 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 41 using intermediate 71 instead of intermediate 52.

[0480] [Chemical Formula 132] Intermediate 72: LCMS: 306 [M+H] + RT=1.88 minutes Refer to manufacturing example 61 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 37 using intermediate 72 instead of intermediate 48.

[0481] [Chemical Formula 133] Intermediate 73: 1 H-NMR (CDCl3) δ: 8.55 (1H, s), 7.36-7.32 (5H, m), 6.53 (1H,d), 6.24 (1H, s), 5.41-5.10 (3H, m), 3.79-3.72 (2H, m), 2.86 (3H, s), 1.54(3H, d). Refer to manufacturing example 62 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 38 using intermediate 73 instead of intermediate 49.

[0482] [Chemical Formula 134] Intermediate 74: LCMS: 312 [M+H] + RT=1.56 minutes Reference Manufacturing Example 63 The following shows the compound and its physical properties manufactured using intermediate 74 instead of intermediate 56 in accordance with Reference Manufacturing Example 44.

[0483] [Chemical Formula 135] Intermediate 75: LCMS: 390 / 392 [M+H] + RT=1.70 minutes Refer to manufacturing example 64 The following shows the compound and its physical properties manufactured using intermediate 75 instead of intermediate 3 in accordance with Reference Manufacturing Example 4.

[0484] [Chemical Formula 136] Intermediate 76: LCMS: 390 [M+H] + RT=1.49 minutes Reference Manufacturing Example 65 The following shows the compound and its physical properties manufactured in accordance with Reference Manufacturing Example 39 using intermediate 76 instead of intermediate 50.

[0485] [Chemical Formula 137] Intermediate 77: 1 H-NMR (CDCl3) δ: 9.48 (1H, s), 9.00 (2H, d), 8.43 (1H, s), 7.43 (1H, t), 4.00 (1H, q), 2.18 (3H, s), 1.45 (3H, d). Manufacturing Example 1 To a mixture of 0.13 g of intermediate 1 and 3.0 mL of chloroform, 1.0 mL of trifluoroacetic acid was added at room temperature, and the mixture was stirred for 2 hours. The resulting mixture was concentrated, and then 3.7 mL of THF, 0.33 mL of N,N-diisopropylethylamine, and 0.10 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially at room temperature, and the mixture was stirred for 1 hour. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 0.059 g of compound 1 of the present invention, as shown in the formula below.

[0486] [Chemical Formula 138] Compound 1 of this invention: LCMS: 495 [M+H] + RT=1.74 minutes Manufacturing Example 2 To a mixture of 0.058 g of intermediate 6 and 2.4 mL of DMF, 0.21 mL of N,N-diisopropylethylamine and 0.066 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.060 g of compound 2 of the present invention.

[0487] [Chemical Formula 139] Compound 2 of this invention: 1 H-NMR (CDCl3) δ: 9.00 (2H, d), 8.61-8.59 (1H, m), 8.50(1H, d), 8.33 (2H, s), 8.07-8.05 (1H, m), 8.00 (1H, s), 7.32 (1H, t), 7.24-7.22 (1H, m), 6.21-6.19 (1H, m), 1.67 (3H, d). Manufacturing Example 3 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 7 instead of intermediate 6.

[0488] [Chemical Formula 140] Compound 3 of this invention: LCMS: 495 [M+H] + RT=1.73 minutes Manufacturing Example 4 To a mixture of 0.11 g of intermediate 7 and 2.0 mL of THF, 0.100 g of 3,5-bis(difluoromethoxy)benzoic acid, 0.136 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, and 0.130 g of 4-dimethylaminopyridine were added sequentially, and the mixture was stirred at room temperature for 6 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed with saturated brine. The organic layer was dried using sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.041 g of compound 4 of the present invention, as shown in the formula below.

[0489] [Chemical Formula 141] Compound 4 of this invention: LCMS: 491[M+H] + RT=1.58 minutes Manufacturing Example 5 The following shows the compound and its physical properties manufactured using intermediate 12 instead of intermediate 3 in accordance with Reference Manufacturing Example 4.

[0490] [Chemical Formula 142] Compound 5 of this invention: 1 H-NMR (CDCl3) δ: 10.05 (1H, d), 8.95 (2H, d), 8.82 (1H,dd), 8.74 (1H, dd), 8.37 (2H, s), 8.00 (1H, s), 7.27 (1H, t), 7.02 (1H, dd),6.14-6.10 (1H, m), 1.61 (3H, d). Manufacturing Example 6 To 0.165 g of 3,5-bis(difluoromethoxy)benzoic acid, 2.9 mL of THF, 2.3 μL of DMF, and 0.061 mL of oxaloyl chloride were added sequentially, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, and 0.5 mL of THF was added to the residue to prepare mixture C. Mixture C was added to a mixture of 0.15 g of intermediate 17, 0.164 mL of triethylamine, and 1.2 mL of THF, and the mixture was stirred at room temperature for 1 hour. Water 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, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.206 g of compound 6 of the present invention, as shown in the formula below.

[0491] [Chemical Formula 143] Compound 6 of this invention: LCMS: 491 [M+H] + RT=1.57 minutes Manufacturing Example 7 The following shows the compounds manufactured according to Manufacturing Example 6 and their physical properties.

[0492] [Chemical Formula 144] In the compound shown in formula (B-4), A 1 A 2 A 3 and A 4 The combination is any combination of compounds listed in [Table B-4].

[0493] [Table 5] Compound 7 of this invention: LCMS: 515 / 517 / 519 [M+H] + RT=1.64 minutes Compound 8 of this invention: LCMS: 462 / 464 [M+H] + RT=1.44 minutes Compound 9 of this invention: LCMS: 547 [M+H] + RT=1.33 minutes Compound 10 of this invention: LCMS: 531 / 533 [M+H] + RT=1.45 minutes Compound 11 of this invention: LCMS: 516 / 518 / 520 [M+H] + RT=1.50 minutes Compound 12 of this invention: LCMS: 515 / 517 [M+H] + RT=1.33 minutes Compound 13 of this invention: LCMS: 438 / 440 [M+H] + RT=1.25 minutes Compound 14 of this invention: LCMS: 495 [M+H] + RT=1.72 minutes Compound 15 of this invention: LCMS: 502 / 504 [M+H] + RT=1.52 minutes Compound 16 of this invention: LCMS: 504 / 506 [M+H] + RT=1.56 minutes Compound 17 of this invention: LCMS: 541 / 543 [M+H] + RT=1.45 minutes Manufacturing Example 8 The following shows the compounds manufactured according to Manufacturing Example 2 and their physical properties.

[0494] [Chemical Formula 145] In the compound shown in formula (B-5), R 3q1 R 3q2 and R 3q3 The combination is any combination of compounds listed in [Table B-5].

[0495] [Table 6] Compound 18 of this invention: LCMS: 523 [M+H] + RT=1.92 minutes Compound 19 of this invention: LCMS: 529 / 531 [M+H] + RT=1.94 minutes Compound 20 of this invention: LCMS: 509 [M+H] + RT=1.83 minutes Compound 21 of this invention: LCMS: 509 [M+H] + RT=1.87 minutes Manufacturing Example 9 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 36 instead of intermediate 6.

[0496] [Chemical Formula 146] Compound 22 of this invention: LCMS: 474 [M+H] + RT=1.78 minutes Manufacturing Example 10 The following shows the compounds manufactured according to Manufacturing Example 2 and their physical properties.

[0497] [Chemical Formula 147] In the compound shown in formula (C-1), R 10 R 4 and R 3q4 The combination is any combination of compounds listed in [Table C-1].

[0498] [Table 7] Compound 23 of this invention: 1H-NMR (CDCl3) δ: 9.04 (2H, d), 8.46 (1H, s), 8.22 (2H,s), 8.01 (1H, s), 7.55 (1H, d), 7.45 (1H, t), 5.85-5.83 (1H, m), 3.12 (3H,s), 1.66 (3H,d). Compound 24 of this invention: 1 H-NMR (CDCl3) δ: 9.54 (1H, s), 9.06 (2H, d), 8.50 (1H,s), 8.21 (2H, s), 8.01 (1H, s), 7.48 (1H, t), 7.42 (1H, d), 5.86-5.84 (1H,m), 1.69 (3H, d). Compound 26 of this invention: 1 H-NMR (DMSO-D6) δ: 9.82 (1H, s), 9.35 (1H, d), 9.00(2H, d), 8.40 (2H, s), 8.29 (1H, s), 7.60 (1H, t), 5.36-5.31 (1H, m), 2.48(3H, s), 1.64(3H, d). Compound 49 of this invention: 1 H-NMR (CDCl3) δ: 9.51 (1H, s), 8.97 (2H, d), 8.49 (1H,s), 7.87 (1H, s), 7.70 (2H, s), 7.40-7.38 (1H, m), 6.31-6.30 (1H, m), 2.87(3H, s), 1.75(3H, d). Manufacturing Example 11 The following shows the compounds manufactured according to manufacturing example 4 and their physical properties.

[0499] [Chemical Formula 148] In the compound shown in formula (C-2), A 5 A 6 R 10 R 4 and R 3q4 The combination is any combination of compounds listed in [Table C-2].

[0500] Compound 27 of this invention: 1H-NMR (DMSO-D6) δ: 9.00-8.97 (3H, m), 8.61 (1H, d), 8.00-7.99 (1H, m), 7.92-7.91 (2H, m), 7.61-7.58 (1H, m), 5.33-5.27 (1H, m), 2.99 (3H, s), 1.60 (3H, d). Compound 28 of this invention: 1 H-NMR (CDCl3) δ:: 9.03 (2H, d), 8.45 (1H, s), 7.63(2H, d), 7.48 (1H, t), 7.43 (1H, t), 7.36 (1H, d), 5.79-5.76 (1H, m), 3.13(3H, s), 1.62 (3H, d). Compound 29 of this invention: 1 H-NMR (CDCl3) δ: 9.41 (1H, s), 9.03 (2H, d), 7.82 (2H,d), 7.78 (1H, t), 7.46-7.43 (1H, m), 7.30 (1H, d), 5.71-5.68 (1H, m), 2.65(3H, s), 1.60(3H, d). Compound 50 of this invention: 1 H-NMR (DMSO-D6) δ: 9.95 (1H, s), 9.03 (1H, d), 9.01(2H, d), 8.64 (1H, s), 7.99 (1H, t), 7.93 (2H, d), 7.62 (1H, t), 5.32-5.27(1H, m), 1.61 (3H, d). Compound 51 of this invention: 1 H-NMR (DMSO-D6) δ: 9.95 (1H, s), 9.03 (1H, d), 9.02(2H, d), 8.65 (1H, s), 7.78-7.76 (3H, m), 7.63 (1H, t), 5.32-5.28 (1H, m), 1.61 (3H, d). Compound 52 of this invention: 1H-NMR (CDCl3) δ: 9.50 (1H, s), 8.98 (2H, d), 8.48 (1H,s), 7.65 (1H, s), 7.41-7.39 (1H, m), 7.30 (2H, s), 6.30-6.27 (1H, m), 2.83(3H, s), 1.71(3H, d). Compound 53 of this invention: 1 H-NMR (CDCl3) δ: 9.50 (1H, s), 8.98 (2H, d), 8.48 (1H,s), 7.40-7.39 (1H, m), 7.34 (1H, s), 7.11 (2H, s), 6.29-6.28 (1H, m), 2.84(3H, s), 1.71(3H, d). Compound 54 of this invention: 1 H-NMR (CDCl3) δ: 9.50 (1H, s), 8.98 (2H, d), 8.48 (1H,s), 8.03 (1H, s), 7.49 (2H, s), 7.40-7.39 (1H, m), 6.30-6.27 (1H, m), 2.81(3H, s), 1.70(3H, d). Compound 55 of this invention: LCMS: 492 [M+H] + RT=1.57 minutes Compound 56 of this invention: LCMS: 516 / 518 [M+H] + RT=1.31 minutes Compound 57 of this invention: LCMS: 503 / 505 [M+H] + RT=1.50 minutes Compound 58 of this invention: 1 H-NMR (CDCl3) δ: 9.50 (1H, s), 8.99 (2H, d), 8.48 (1H,s), 7.58 (1H, s), 7.41-7.40 (1H, m), 7.29 (2H, s), 6.29-6.28 (1H, m), 2.85(3H, s), 1.73 (3H, d), 1.68 (6H, d). Manufacturing Example 21 To a mixture of 0.16 g of intermediate 51 and 6.3 mL of DMF, 0.17 g of 3-difluoromethyl-1-methyl-1H-pyrazole-5-carboxylic acid, 0.24 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.32 mL of N,N-diisopropylethylamine, and 0.13 g of 1-hydroxybenzotriazole were added sequentially, and the mixture was stirred at room temperature for 22 hours. Water was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed with water and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.10 g of compound 47 of the present invention, as shown in the formula below.

[0501] [Chemical Formula 149] Compound 47 of this invention: 1 H-NMR (CDCl3) δ: 9.03 (2H, d), 8.46 (1H, s), 7.43 (1H,t), 7.34 (1H, d), 6.77-6.58 (2H, m), 5.77-5.75 (1H, m), 4.13 (3H, s), 3.13 (3H, s), 1.61 (3H, d). Manufacturing Example 22 A mixture of 0.052 g of intermediate 61 and 2.8 mL of trifluoroacetic acid was stirred at 70 °C for 4 hours. The resulting mixture was cooled to room temperature and concentrated, then extracted with methyl tert-butyl ether and water. The resulting aqueous layer was adjusted to pH 10 by adding saturated sodium bicarbonate, and then extracted with chloroform (containing 20% ​​isopropanol by volume). The resulting organic layer was dried using sodium sulfate, filtered, and concentrated.

[0502] The residue was added sequentially at room temperature with 2.8 mL of DMF, 0.071 mL of N,N-diisopropylethylamine, and 0.82 g of 3,5-bis(trifluoromethyl)benzoyl chloride, and stirred for 3 hours. Water was added to the resulting mixture, and extraction was performed using chloroform. The resulting organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to give 0.046 g of compound 25 of the present invention, as shown in the formula below.

[0503] [Chemical Formula 150] Compound 25 of this invention: 1H-NMR (CDCl3) δ: 9.02 (2H, d), 8.23 ​​(2H, s), 8.00 (1H,s), 7.76 (1H, d), 7.67 (1H, d), 7.59 (1H, d), 7.42 (1H, t), 5.61-5.59 (1H,m), 2.94 (3H, s), 1.58 (3H, d). Manufacturing Example 12 Under a nitrogen atmosphere, 0.24 g of 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-1-H-pyrazole, 0.073 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, and 0.65 g of potassium phosphate were added sequentially to a mixture of 0.50 g of intermediate 63, 10 mL of toluene, and 1.0 mL of water. The mixture was stirred under reflux for 3 hours. The resulting mixture was cooled to room temperature, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.060 g of compound 30 of the present invention.

[0504] [Chemical Formula 151] Compound 30 of this invention: 1 H-NMR (CDCl3) δ: 9.40 (1H, s), 8.45 (1H, s), 8.25 (2H,s), 8.01 (1H, s), 7.74 (1H, d), 7.58 (1H, d), 7.19 (1H, d), 6.28-6.26 (1H,m), 4.07 (3H, s), 1.67 (3H, d). Manufacturing Example 12-1 The following shows the compounds manufactured according to manufacturing example 12 and their physical properties.

[0505] [Chemical Formula 152] In the compound shown in formula (C-3), R 2a R 2b R 2c and R 2d The combination is any combination of compounds listed in [Table C-3].

[0506] [Table 8] Compound 31 of this invention:1 H-NMR (CDCl3) δ: 9.47 (1H, s), 8.43 (1H, s), 8.23 ​​(2H,s), 8.03 (1H, s), 7.97-7.95 (2H, m), 7.87-7.85 (1H, m), 7.77-7.75 (1H, m),7.12 (1H, d), 5.47-5.43 (1H, m), 1.57 (3H, d). Compound 32 of this invention: 1 H-NMR (CDCl3) δ: 9.46 (1H, s), 8.42 (1H, s), 8.23 ​​(2H,s), 8.03 (1H, s), 7.92 (2H, d), 7.82 (2H, d), 7.09 (1H, d), 5.50-5.48 (1H,m), 1.55 (3H, d). Compound 33 of this invention: 1 H-NMR (CDCl3) δ: 9.44 (1H, s), 8.42 (1H, s), 8.23 ​​(2H,s), 8.03 (1H, s), 7.38-7.36 (2H, m), 7.05 (1H, d), 5.53-5.50 (1H, m), 1.57(3H, d). Compound 34 of this invention: 1 H-NMR (CDCl3) δ: 9.45 (1H, s), 8.42 (1H, s), 8.23 ​​(2H,s), 8.02 (1H, s), 7.67-7.65 (1H, m), 7.60 (1H, d), 7.51 (1H, d), 7.42 (1H,d), 7.12 (1H,d), 5.56-5.49 (1H,m), 1.55 (3H,d). Compound 35 of this invention: LCMS: 498 [M+H] + RT=2.01 minutes Compound 36 of this invention: 1H-NMR (CDCl3) δ: 9.42 (1H, s), 8.40 (1H, s), 8.24 (2H,s), 8.02 (1H, s), 7.56-7.54 (2H, m), 7.21 (1H, d), 7.14-7.12 (2H, m), 5.68-5.66 (1H, m), 3.90 (3H, s), 1.54 (3H, d). Manufacturing Example 12-2 The following shows the compounds and their physical properties produced in accordance with Manufacturing Example 12 using pyridine-4-boronic acid instead of 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-1-H-pyrazole.

[0507] [Chemical Formula 153] Compound 48 of this invention: 1 H-NMR (CDCl3) δ: 9.47 (1H, s), 8.90-8.89 (2H, m), 8.43(1H, s), 8.24 (2H, s), 8.03 (1H, s), 7.64-7.63 (2H, m), 7.14 (1H, d), 5.54-5.52 (1H, m), 1.55 (3H, d). Manufacturing Example 13 A mixture of 0.30 g of intermediate 63, 0.22 g of sodium 5-(trifluoromethyl)pyridine-2-sulfinate, 0.027 g of palladium(II) acetate, 0.034 g of tricyclohexylphosphine, 0.17 g of potassium carbonate, and 3.1 mL of 1,4-dioxane was stirred at 150 °C for 1.5 h using a microwave reaction apparatus. The resulting mixture was cooled to room temperature, concentrated under reduced pressure, and then dissolved in chloroform. After filtration through diatomaceous earth, the resulting solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.26 g of compound 37 of the present invention.

[0508] [Chemical Formula 154] Compound 37 of this invention: 1H-NMR (CDCl3) δ: 9.50 (1H, s), 9.12 (1H, s), 8.46 (1H,s), 8.25 (1H, d), 8.21-8.20 (3H, m), 8.01 (1H, s), 7.24 (1H, d), 5.77-5.72(1H, m), 1.75 (3H, d). Manufacturing Example 14 Under a nitrogen atmosphere, 0.44 mL of ethanethiol was added to a mixture of 0.50 g of intermediate 63, 0.073 g of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, 0.43 g of potassium carbonate, and 10.4 mL of 1,4-dioxane, and the mixture was stirred at 80 °C for 6 hours. The resulting mixture was cooled to room temperature, concentrated under reduced pressure, and then extracted with chloroform by adding water. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of compound 38 of the present invention.

[0509] [Chemical Formula 155] Compound 38 of this invention: 1 H-NMR (CDCl3) δ: 9.34 (1H, s), 8.45 (1H, s), 8.28 (2H,s), 8.03 (1H, s), 7.40 (1H, d), 6.17-6.14 (1H, m), 3.53-3.36 (2H, m), 1.58(3H, d), 1.32(3H, t). Manufacturing Example 15 A mixture of 0.45 g of intermediate 63, 0.38 g of 2-(tributyltinyl)thiazole, 0.10 g of tetra(triphenylphosphine)palladium (0), 0.036 g of copper iodide (I), 0.039 g of lithium chloride, and 9.3 mL of 1,4-dioxane was stirred at 100 °C for 13 hours. The resulting mixture was cooled to room temperature, concentrated under reduced pressure, and then dissolved in chloroform. After filtration through diatomaceous earth, the resulting solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.12 g of compound 39 of the present invention.

[0510] [Chemical Formula 156] Compound 39 of this invention: 1H-NMR (CDCl3) δ: 9.44 (1H, s), 8.54 (1H, s), 8.25 (2H,s), 8.19 (1H, d), 8.01 (1H, s), 7.77 (1H, d), 7.74 (1H, d), 6.73-6.70 (1H,m), 1.75 (3H, d). Manufacturing Example 15-1 The following shows the compounds and their physical properties produced in accordance with Manufacturing Example 15 using 2-(tributyltinyl)pyridine instead of 2-(tributyltinyl)thiazole.

[0511] [Chemical Formula 157] Compound 40 of this invention: 1 H-NMR (CDCl3) δ: 9.47 (1H, s), 8.85-8.84 (1H, m), 8.45(1H, s), 8.22 (2H, s), 8.01-8.00 (2H, m), 7.97-7.96 (1H, m), 7.51 (1H, d),7.47-7.46 (1H, m), 5.80-5.77 (1H, m), 1.67 (3H, d). Manufacturing Example 16 A mixture of 0.30 g of intermediate 64, 1.6 mL of THF, and 1.6 mL of 3 mol / L hydrochloric acid was stirred at room temperature for 1 hour. A saturated aqueous sodium carbonate solution was added to the resulting mixture, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of compound 41 of the present invention.

[0512] [Chemical Formula 158] Compound 41 of this invention: 1 H-NMR (CDCl3) δ: 9.43 (1H, s), 8.49 (1H, s), 8.21 (2H,s), 8.02 (1H, s), 7.07 (1H, d), 5.71-5.66 (1H, m), 3.03 (3H, s), 1.71 (3H,d). Manufacturing Example 17 A mixture of 0.20 g of compound 41 of the present invention, 0.10 g of methoxyamine hydrochloride, 0.074 g of sodium acetate, and 4.5 mL of ethanol was stirred at 50 °C for 3 hours. The resulting mixture was cooled to room temperature, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.20 g of compound 42 of the present invention.

[0513] [Chemical Formula 159] Compound 42 of this invention: 1 H-NMR (CDCl3) δ: 9.39 (1H, s), 8.44 (1H, s), 8.23 ​​(2H,s), 8.02 (1H, s), 7.19 (1H, d), 5.76-5.72 (1H, m), 4.06 (3H, s), 2.48 (3H,s), 1.69 (3H,d). Manufacturing Example 17-1 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 17 using hydroxylamine hydrochloride instead of methoxyamine hydrochloride.

[0514] [Chemical Formula 160] Compound 43 of this invention: 1 H-NMR (DMSO-D6) δ: 9.30 (1H, d), 9.20 (1H, s), 8.80 (1H, s), 8.45 (2H, s), 8.30 (1H, s), 5.16 (1H, s), 2.29 (3H, s), 1.50 (3H,d). Manufacturing Example 19 A mixture of 1.0 g of intermediate 78, 0.19 g of hydroxylamine hydrochloride, 0.25 g of sodium acetate, and 10.0 mL of ethanol was stirred at 80 °C for 6 hours. The resulting mixture was cooled to room temperature, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.47 g of compound 45 of the present invention.

[0515] [Chemical Formula 161] Compound 45 of this invention: LCMS: 475 [M+H]+ RT=1.43 minutes Manufacturing Example 20 To a mixture of 0.17 g of compound 45 of the present invention and 3.6 mL of pyridine, 0.042 g of acetyl chloride was added, and the mixture was stirred at room temperature for 2 hours. The mixture was then stirred further at 80°C for 13 hours. The resulting mixture was cooled to room temperature, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine. The organic layer was dried using sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.072 g of compound 46 of the present invention.

[0516] [Chemical Formula 162] Compound 46 of this invention: LCMS: 499 [M+H] + RT=1.86 minutes Next, examples of compounds of the present invention manufactured according to any of the manufacturing examples described in the embodiments and the manufacturing methods described in this specification are shown below.

[0517] [Chemical Formula 163] In the compound represented by formula (L-1) (hereinafter referred to as compound (L-1)), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-1 (#) 4 (Indicates the bonding site with the carbon atom of the carbonyl group), R 2 For those recorded in [Table L1] to [Table L20] (#) 3 Compounds with any substituents (representing the bonding site with a carbon atom in a fused ring) are hereinafter referred to as compound group SX1.

[0518] [Table 9] [Table 10] [Table 11] [Table 12] [Table 13] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-1, R 2Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX2).

[0519] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-1, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX3).

[0520] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-1, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX4.

[0521] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-1, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX5).

[0522] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-1, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX6).

[0523] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX7).

[0524] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX8).

[0525] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX9).

[0526] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX10).

[0527] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX11).

[0528] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-2, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX12).

[0529] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX13).

[0530] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX14).

[0531] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX15).

[0532] In compound (L-1), R1 For methyl, R 10 For methyl, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX16).

[0533] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX17).

[0534] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-3, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX18).

[0535] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-4, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX19).

[0536] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-4, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX20).

[0537] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-4, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX21).

[0538] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-4, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX22.

[0539] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-4, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX23).

[0540] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-4, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX24).

[0541] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-5, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX25).

[0542] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-5, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX26).

[0543] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-5, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX27).

[0544] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-5, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX28).

[0545] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-5, R 2Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX29).

[0546] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-5, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX30).

[0547] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX31).

[0548] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX32).

[0549] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX33).

[0550] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX34).

[0551] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX35).

[0552] In compound (L-1), R 1 For methyl, R 10 For ethyl, R11 For T1-6, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX36).

[0553] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-7, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX37).

[0554] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-7, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX38).

[0555] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-7, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX39).

[0556] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-7, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX40).

[0557] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-7, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX41).

[0558] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-7, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX42).

[0559] In compound (L-1), R1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX43).

[0560] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX44).

[0561] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX45).

[0562] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX46).

[0563] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX47).

[0564] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-8, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX48).

[0565] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-9, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX49).

[0566] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-9, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX50).

[0567] In compound (L-1), R 1 For hydrogen atoms, R 10 For methyl, R 11 For T1-9, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX51).

[0568] In compound (L-1), R 1 For methyl, R 10 For methyl, R 11 For T1-9, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX52.

[0569] In compound (L-1), R 1 For hydrogen atoms, R 10 For ethyl, R 11 For T1-9, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX53).

[0570] In compound (L-1), R 1 For methyl, R 10 For ethyl, R 11 For T1-9, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX54).

[0571] In compound (L-1), R 1 For hydrogen atoms, R 10 For hydrogen atoms, R 11 For T1-10, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX55).

[0572] In compound (L-1), R 1 For methyl, R 10 For hydrogen atoms, R 11 For T1-10, R 2Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX56).

[0573] In compound (L-1), R 1 For hydrogen ...

Claims

1. The compound shown in formula (I) or its N oxide, [Chemical Formula 1] In formula (I), L indicates a single bond or - (CR) 4a R 4b ) n -, R 4a and R 4b The same or different from each other indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a C1-C6 alkoxy group, a cyano group, a hydroxyl group, a halogen atom, or a hydrogen atom that can be substituted with one or more halogen atoms. n represents 1, 2, 3, 4, 5, or 6. R 1 This refers to a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from the group consisting of cyclopropyl and halogen atoms; a C3-C6 cycloalkyl group that can be substituted by one or more halogen atoms; or a C1-C6 alkoxy, cyano, halogen atom, hydroxyl, or hydrogen atom that can be substituted by one or more halogen atoms. Q represents the group shown in formula A1, formula A2, formula A3, formula A4, formula A5, or formula A6 (# indicates a group with R). 2 The bonding sites (● indicates the bonding sites with carbon atoms). [Chemical Formula 2] Q 1 Q 2 and Q 3 Combinatorial representation: Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 The combination; Q 1 For nitrogen atoms, Q 2 For CR 3q2 Q 3 For CR 3q3 The combination; Q 1 For CR 3q1 Q 2 For nitrogen atoms, Q 3 For CR 3q3 Combinations; or Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 A combination of nitrogen atoms, Q 1a and Q 2a Combinatorial representation: Q 1a For CR 3q4 Q 2a For CR 3q5 The combination; Q 1a For nitrogen atoms, Q 2a For CR 3q5 Combinations; or Q 1a For CR 3q4 Q 2a A combination of nitrogen atoms, R 3q1 R 3q2 R 3q3 R 3q4 R 3q5 and R 4 "Same or different from each other" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or NR. 6 C(O)R 5 NR 6 C(O)OR 5 NR 6 C(O)NR 5 R 12 C(O)NR 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), N=S(O) p R 28 R 15 cyano, halogen, or hydrogen atoms Z 1 Represents oxygen or sulfur atoms. p represents 0 or 1. R 5 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 6 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 7 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 9 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 12 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 15 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a phenyl group that can be substituted by one or more substituents selected from group B, or a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group B. R 2 This indicates a phenyl group that can be substituted by one or more substituents selected from group A, a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A, or a C(O)NR group. 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), C(O)R 5 NR 16 C(O)R 17 NR 16 C(O)OR 17 NR 16 C(O)NR 17 R 18 S(O)2NR 16 R 17 OR 18 S(O) m R 15 , thiol, group shown in formula E1, group shown in formula E2, or group shown in formula E3 (# 2 (This indicates the bonding site with the group shown in Formula A1, Formula A2, Formula A3, Formula A4, Formula A5, or Formula A6). [Chemical Formula 3] m represents 0, 1, or 2. R 16 R 17 and R 18 "Same" or "different from each other" refers to a phenyl group that can be substituted by one or more substituents selected from group B, a 5- or 6-membered heterocyclic group that can be substituted by one or more substituents selected from group B, a C1-C6 alkyl group that can be substituted by one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 2 For NR 16 C(O)R 17 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom and R 17 The bonded carbon atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}. R 2 For NR 16 C(O)OR 17 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 The bonded oxygen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}. R 2 For NR 16 C(O)NR 17 R 18 In the case of R 16 and R 17 Can be used with R 16 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 17 The bonded nitrogen atoms together form a 5- or 6-membered non-aromatic heterocycle that can be substituted by a C1-C3 chain hydrocarbon group {which can be substituted by one or more halogen atoms}. Q 5 CR E11 R 27 NR E12 oxygen or sulfur atoms Q 4 CR E13 Or nitrogen atoms, Q 6 CR E14 Or nitrogen atoms, Q 7 CR E15 Or nitrogen atoms, Q 8 CR E16 Or nitrogen atoms, Q 9 CR E17 or nitrogen atoms (where, The group represented by formula E2 does not include Q. 6 and Q 7 In the case of nitrogen atoms, Q 6 Q 8 and Q 9 The case where it is simultaneously a nitrogen atom, and Q 7 Q 8 and Q 9 (The case where both are nitrogen atoms) Q 10 CR E18 Or nitrogen atoms, R E11 and R E31 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, or a C(O)NR group. 7 R 8 NR 9 C(O)R 5 A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 8 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R E12 and R E32 "Identical" or "different from each other" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 27 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group B, consisting of halogen atoms and cyano groups, a phenyl group, or a hydrogen atom that can be substituted by one or more substituents selected from group B. R E13 R E14 R E15 R E16 R E17 and R E18 "Same or different" indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, a C1-C6 alkoxy group that can be substituted by one or more halogen atoms, or a C(O)NR group. 7 R 8 NR 9 C(O)R 5 A C3-C6 cycloalkyl, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. X represents NR 10 C(Z)R 11 、NR 10 C(O)OR 11 、NR 10 C(Z)NR 11 R 12 、NR 10 C(=NOR 9 )R 11 、NR 10 C(=NOR 9 )(NR 11 R 12 )、N=C(OR 9 )R 11 、N=C(SR 15 )R 11 、N=C(NR 6 R 7 )R 11 、NR 10 X 1 or N=S(O) p R 11 R 28 , Z represents an oxygen atom or a sulfur atom. X 1 This indicates a 9- or 10-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A. R 10 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, a C1-C6 alkylsulfonyl group that can be substituted by one or more halogen atoms, OR 14 C(O)R 13 C(O)OR 13 C (=NR) 7 R 13 C(O)NR 6 R 7 Or hydrogen atoms, R 11 This indicates a phenyl group that can be substituted by one or more substituents selected from group A, or a 5- or 6-membered aromatic heterocyclic group that can be substituted by one or more substituents selected from group A. R 13 This indicates a C1-C6 chain hydrocarbon group or phenyl group that can be substituted with one or more halogen atoms {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C6 alkoxy groups that can be substituted with one or more halogen atoms, C1-C6 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups or hydrogen atoms that can be substituted with one or more halogen atoms, R 14 This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a phenylmethyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more halogen atoms, or a hydrogen atom. R 28 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group C, or a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E. Group A: A C1-C6 chain hydrocarbon group {which may be substituted by one or more substituents selected from the group consisting of: C3-C6 cycloalkyl, cyano, and halogen atoms that may be substituted by one or more halogen atoms}, C3-C6 cycloalkyl {which may be substituted by one or more substituents selected from the group consisting of C1-C6 alkoxy, cyano, and halogen atoms}, a phenyl group that may be substituted by one or more substituents selected from Group B, a 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from Group B, OR 3a SF5, NR 3d OR 3b NR 3b C(O)R 3c NR 3d NR 3b C(O)R 3c NR 3b C(O)OR 3e NR 3d NR 3b C(O)OR 3e NR 3b C(O)NR 3f R 3g NR 3d NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g S(O)2NR 3f R 3g NR 3b C (=NOR) 3j R 3d NR 3b S(O)2R 3k S(O) m R 3k A group composed of cyano, nitro and halogen atoms. R 3a The following groups represent C3-C6 cycloalkyl groups that can be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms; phenyl groups that can be substituted with one or more substituents selected from group B; 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more substituents selected from group B; and C(O)R groups. 3c C(O)OR 3j C(O)NR 3f R 3g S(O)2R 3k Or hydrogen atoms, R 3b This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3c This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B, or a hydrogen atom. R 3d This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3e This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a (C1-C3 alkyl)phenyl group {the phenyl portion of the (C1-C3 alkyl)phenyl group can be substituted with one or more substituents selected from group B}. R 3f This refers to a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3g This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, or a hydrogen atom. R 3h This indicates a C1-C6 alkyl group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, a 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B, or a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms. R 3i This refers to C1-C6 alkyl groups that can be substituted with one or more halogen atoms, or C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms. R 3j This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenyl group that can be substituted by one or more substituents selected from group B, or a hydrogen atom. R 3k This indicates a C1-C6 chain hydrocarbon group that can be substituted with one or more halogen atoms, a phenyl group that can be substituted with one or more substituents selected from group B, or a C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms. Group B: A group consisting of C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, C1-C6 alkoxy groups, cyano groups, hydroxyl groups and halogen atoms that can be substituted with one or more halogen atoms. Group C: C3-C6 cycloalkyl groups substituted with one or more substituents selected from Group E; phenyl groups substituted with one or more substituents selected from Group B; 5- or 6-membered aromatic heterocyclic groups substituted with one or more substituents selected from Group B; OR 3a NR 3d OR 3b NR 3b C(O)R 3c NR 3d NR 3b C(O)R 3c NR 3b C(O)OR 3e NR 3d NR 3b C(O)OR 3e NR 3b C(O)NR 3f R 3g NR 3d NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g S(O) m R 3k A group composed of cyano, nitro and halogen atoms. Group E: Composed of C1-C6 chain hydrocarbon groups that can be substituted by one or more halogen atoms, OR 3a S(O) m R 3k A group composed of oxo groups, cyano groups, and halogen atoms. Group F: C3-C6 cycloalkyl groups substituted with one or more substituents selected from Group E; phenyl groups substituted with one or more substituents selected from Group B; 5- or 6-membered aromatic heterocyclic groups substituted with one or more substituents selected from Group B; OR 3a S(O) m R 3k C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g NR 3b R 3c NR 3b C(O)R 3c NR 3b C(O)NR 3f R 3g N=S(O) p R 3h R 3i A group consisting of 3-6 non-aromatic heterocyclic groups, cyano groups, and halogen atoms.

2. The compound or its N oxide as claimed in claim 1, wherein, R 3a C3-C6 cycloalkyl groups that can be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; C1-C6 chain hydrocarbon groups that can be substituted with one or more halogen atoms; phenyl groups that can be substituted with one or more substituents selected from group B; 5- or 6-membered aromatic heterocyclic groups that can be substituted with one or more substituents selected from group B; C(O)R 3c C(O)OR 3j C(O)NR 3f R 3g Or hydrogen atoms.

3. The compound or its N oxide as described in claim 1 or 2, wherein, In formula (I), L represents a single bond. R 1 It is methyl. Q is a group represented by formula A1, formula A2, or formula A3. Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 , R 3q1 R 3q2 and R 3q3 They may be the same or different from each other, consisting of methyl, halogen, or hydrogen atoms. Q 1a and Q 2a The combination is: Q 1a For CR 3q4 Q 2a For CR 3q5 The combination; Q 1a For nitrogen atoms, Q 2a For CR 3q5 Combinations; or Q 1a For CR 3q4 Q 2a A combination of nitrogen atoms, R 3q4 R 3q5 and R 4 They may be the same or different from each other, consisting of methyl, halogen, or hydrogen atoms. R 2 The phenyl, pyrazolyl, thiazolyl, oxadiazolyl, pyridyl, and pyrimidinyl groups {the phenyl, pyrazolyl, thiazolyl, oxadiazolyl, pyridyl, and pyrimidinyl groups may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups substituted by one or more halogen atoms, C1-C3 alkoxy groups substituted by one or more halogen atoms, cyano groups, and halogen atoms}, C(O)NR 6 R 7 C (=NOR) 9 R 5 C (=NOR) 9 (NR) 6 R 7 ), C(O)R 5 Or S(O) m R 15 , R 5 It is a C1-C3 alkyl group. R 6 It is a methyl or hydrogen atom. R 7 It is a C1-C3 alkyl group or a hydrogen atom. R 9 It is a C1-C3 alkyl group or a hydrogen atom. R 15 It is a C1-C3 alkyl group. m is 0, 1, or 2. X is NR 10 C(Z)R 11 or NR 10 C(Z)NR 11 R 12 , Z stands for oxygen atom. R 10 It is a methyl or hydrogen atom. R 11 The group is phenyl, pyrazolyl, or pyridyl {the phenyl, pyrazolyl, and pyridyl groups may be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl which may be substituted by a cyano, and a halogen atom}. R 12 It is a hydrogen atom.

4. The compound or its N oxide according to any one of claims 1 to 3, wherein, In formula (I), L represents a single bond. R 1 It is methyl. Q is a group represented by formula A1 or a group represented by formula A2. Q 1 For CR 3q1 Q 2 For CR 3q2 Q 3 For CR 3q3 , R 3q1 R 3q2 and R 3q3 It is a hydrogen atom. R 2 It is phenyl, pyrazolyl, pyridyl, or pyrimidinyl {the phenyl, pyrazolyl, pyridyl, and pyrimidinyl groups may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkyl groups, cyano groups, and halogen atoms that may be substituted by one or more halogen atoms}, X is NR 10 C(Z)R 11 or NR 10 C(Z)NR 11 R 12 , Z stands for oxygen atom. R 10 It is a methyl or hydrogen atom. R 11 The phenyl, pyrazolyl, or pyridyl group can be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl that can be substituted by a cyano, and a halogen atom. R 12 It is a hydrogen atom.

5. A composition for controlling harmful arthropods, comprising an inactive carrier and the compound or its N oxide as described in any one of claims 1 to 4.

6. A composition comprising one or more ingredients selected from the group consisting of (a), (b), (c), and (d), and the compound or its N oxide as described in any one of claims 1 to 4: Group (a): A group consisting of insecticidal, acaricidal, and nematicidal active ingredients; Group (b): Bactericidal active ingredients; Group (c): Plant growth regulators; Group (d): Repellent component.

7. Methods for controlling harmful arthropods, including, Apply an effective amount of the compound of any one of claims 1 to 4 or its N oxide, or an effective amount of the composition of claim 6, to a harmful arthropod or its habitat.

8. A seed or vegetative reproductive organ containing an effective amount of any one of claims 1 to 4, or its N oxide, or an effective amount of the composition of claim 6.

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