Heterocyclic 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, Z represents an oxygen atom or the like, 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, R3 represents a C1-C6 chain hydrocarbon group or the like, R4 represents a hydrogen atom or the like, X represents NR11C (Z) R12 or the like, R11 represents a C1-C6 chain hydrocarbon group or the like, and X represents a hydrogen atom or the like. And R12 represents a phenyl group which may be substituted by one or more substituents, 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. 2023-175798 (filed on October 11, 2023), the entire contents of which are incorporated herein by reference.

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

[0003] To date, various compounds have been studied for the purpose of controlling harmful arthropods.

[0004] On the other hand, Patent Document 1 describes a certain heterocyclic compound that is useful for the treatment of inflammatory and immune diseases.

[0005] Existing technical documents Patent documents Patent Document 1: International Publication No. 2007 / 002701 Summary of the Invention

[0006] 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.

[0007] 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.

[0008] The present invention is described below.

[0009] [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, Z represents an oxygen atom or a sulfur atom. L indicates a single bond or - (CR) 4a R 4b ) n -, R 4a and R 4bThe 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. 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. 7a R 8a C (=NOR) 10 R 5a C (=NOR) 10 (NR) 7 R 8 ), NR 19 C(O)R 20 NR 19 C(O)OR 20 NR 19 C(O)NR 20 R 21 S(O)2NR 16 R 17 OR 18 S(O) m R 29 The group represented by formula E1, the group represented by formula E2, or the group represented by formula E3 (#) 2 (Indicates the bonding site with a carbon atom). [Chemical Formula 2] R 19 R 20 and R 21 "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 19 C(O)R 20 In the case of R 19 and R20 Can be used with R 19 The bonded nitrogen atom and R 20 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 19 C(O)OR 20 In the case of R 19 and R 20 Can be used with R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 19 C(O)NR 20 R 21 In the case of R 19 and R 20 Can be used with R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 2 Indicates CR 22 R 27 NR 23 oxygen or sulfur atoms Q 1 Indicates CR 22a Or nitrogen atoms, Q 3 Indicates CR 22b Or nitrogen atoms, Q 4 Indicates CR 22c Or nitrogen atoms, Q 5 Indicates CR 22d Or nitrogen atoms, Q 6 Indicates CR 22e or nitrogen atoms (Among them, the groups represented by formula E2 do not include Q) 3 and Q 4 In the case of nitrogen atoms, Q 3 Q 5 and Q 6 The case where it is simultaneously a nitrogen atom, and Q 4 Q5 and Q 6 (The case where both are nitrogen atoms) Q 7 Indicates CR 22f Or nitrogen atoms, R 22 and R E1 "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 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 22a R 22b R 22c R 22d R 22e and R 22f "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 23 and R E2 "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 16 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 17 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 3 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 A C3-C6 cycloalkyl group or a hydrogen atom that can be substituted by one or more substituents selected from group E. R 4 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, or OR. 18 S(O) m R 29 NR 7b R 8b C(O)NR 7b R 8b NR 9b C(O)R 5b NR 9b C(O)OR 6b NR 9 C(O)NR 7 R 8 A C3-C6 cycloalkyl, mercapto, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 18 This indicates 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, or a hydrogen atom. m represents 0, 1, or 2. R 29 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. R 3 and R 4 Can be used with R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form the group shown in formula A1, formula A2, formula A3, formula A4, formula A5, formula A6, or formula A7 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 3] B 1 B 2 B 3 and B 4 Combinatorial representation: B 1 For CR 2a B 2 For CR 2b B 3 Nitrogen atom or CR 2c B 4 Nitrogen atom or CR 2d The combination; B 1 For CR 2a B 2 For nitrogen atoms, B 3 For CR 2c B 4 Nitrogen atom or CR 2d The combination; B 1 For CR 2a B 2 For nitrogen atoms, B 3 For nitrogen atoms, B 4 For CR 2d The combination; B 1 For nitrogen atoms, B 2 For CR 2b B 3 For nitrogen atoms, B 4 For CR 2d The combination; B 1 For nitrogen atoms, B 2 For CR 2b B 3 For CR 2c B 4 Nitrogen atom or CR 2d Combinations; or B 1 For nitrogen atoms, B 2 For nitrogen atoms, B 3 For CR 2c B 4 For CR 2d The combination B 5 and B 8 The same or different from each other indicates CR 25 Or nitrogen atoms, B6 and B 7 The same or different from each other indicates oxygen atom, sulfur atom, or NR. 26 , R 25 This 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, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 C (=NOR) 10 R 5 C (=NOR) 10 (NR) 7 R 8 ), NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 N=S(O) p R 24 R 28 S(O) m R 29 cyano, halogen, or hydrogen atoms R 26 This indicates 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 halogen atoms, or a hydrogen atom. R A and R B "Identical" or "different from each other" refers to C1-C6 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms. R 2a R 2b R 2c R 2d R 2e R 2f R 2g R 2h R 2i R 2j R 2k R 2l R 2m R 2n R 2oR 2p R 2q R 2r R 2s R 2t R 2u and R 2v "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, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 C (=NOR) 10 R 5 C (=NOR) 10 (NR) 7 R 8 ), NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 N=S(O) p R 24 R 28 S(O) m R 29 cyano, halogen, or hydrogen atoms X represents NR 11 C(Z)R 12 NR 11 C(O)OR 12 NR 11 C(Z)NR 12 R 13 NR 11 C (=NOR) 10 R 12 NR 11 C (=NOR) 10 (NR) 11 R 12 N=C (OR) 10 R 12 N=C(SR) 10 R 12 N=C(NR) 7 R 8 R 12 NR 11 X1 Or N=S(O) p R 12 R 28 , p represents 0 or 1. X 1 This indicates a 9- or 10-membered aromatic heterocyclic group {this 9- or 10-membered aromatic heterocyclic group can be selected from group A} 2 If one or more substituents are used in the heterocycle, the ring member atoms of the heterocycle, in addition to the carbon atom, include one, two, or three heteroatoms selected from the group consisting of N, O, and S. R 5 R 5a and R 5b "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 a hydrogen atom. R 6 and R 6b "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 C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 7 R 7a and R 7b "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, or a C3-C6 cycloalkyl, cyano, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 8 R 8a and R 8b "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 a hydrogen atom. R 9 and R 9b "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 D, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 10This 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 11 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 15 C(O)R 14 C(O)OR 14 C (=NR) 8 R 14 C(O)NR 7 R 8 or hydrogen atoms, R 12 This indicates that it can be selected from group A. 3 The phenyl group having one or more substituents, or being selected from group A 3 A 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, R 24 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, or a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E. 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. R 13 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 14 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: halogen atom, C1-C6 alkoxy group that can be substituted with one or more halogen atoms, C1-C6 alkyl group that can be substituted with one or more halogen atoms, and cyano group}, 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, or hydrogen atom. R 15It represents a C1-C6 chain hydrocarbon group that can be replaced by one or more halogen atoms, a C3-C6 cycloalkyl group that can be replaced by one or more halogen atoms, a phenylmethyl group {the phenyl part of the phenylmethyl group can be replaced by one or more halogen atoms}, a phenyl group that can be replaced by one or more halogen atoms, or a hydrogen atom.

[0010] 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 3b1 C(O)R 3c1 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 3f1 R 3g1 S(O)2NR 3f R 3g NR 3b C (=NOR) 3j R 3d NR 3b S(O) m R 3k S(O) m R 3k It is a group composed of cyano, nitro and halogen atoms.

[0011] Group A 2: 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}, phenyl that may be substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group B, OR 3aa 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) m R 3k S(O) m R 3k It is a group composed of cyano, nitro and halogen atoms.

[0012] Group A 3: 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}, phenyl that may be substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group B, OR 3ab 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) m R 3k S(O) m R 3ka It is a group composed of cyano, nitro and halogen atoms.

[0013] R 3a R 3aa and R 3ab"Same or different" refers to 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 3c C(O)OR 3j C(O)NR 3f R 3g S(O)2R 3k or hydrogen atoms, R 3b and R 3b1 The same or different from each other indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3c and R 3c1 "Same" or "different" refers to 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 phenyl C1-C3 alkyl group {where the phenyl portion of the phenyl C1-C3 alkyl group can be substituted with one or more substituents selected from group B}. R 3f and R 3f1 The same or different from each other indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3g and R 3g1 "Same" or "different" refers to 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 3iThis 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 and R 3ka "Same or different" refers to 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.

[0014] 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.

[0015] 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 It is a group composed of cyano, nitro and halogen atoms.

[0016] Group D: 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.

[0017] 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 cyano groups, oxo groups, and halogen atoms.

[0018] 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.

[0019] Group G: 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 3dNR 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 consisting of 3-6 membered non-aromatic heterocyclic groups, cyano groups, nitro groups, and halogen atoms.] [2] The compound or its N oxide as described in [1], wherein R 3a R 3aa and R 3ab "Same or different" refers to 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 3c C(O)OR 3j C(O)NR 3f R 3g , or hydrogen atoms.

[0020] [3] The compound or its N oxide as described in [1] or [2], wherein, in formula (I), Z stands for oxygen atom. L is a single bond or -(CR) 4a R 4b ) n -, R 4a and R 4b They may be the same or different from each other, and are C1-C3 alkyl or hydrogen atoms. n is 1, 2, or 3. R 1 It is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 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} 3b1 C(O)R 3c1 C(O)NR 3f1 R 3g1 , cyano group and halogen atom}, C(O)NR 7a R8a C (=NOR) 10 R 5a The group shown in formula E1-1 or the group shown in formula E3-1 (# 2 (Indicates the bonding site with a carbon atom). [Chemical Formula 4] R 3b1 It is a C1-C3 alkyl group or a hydrogen atom. R 3c1 It is a C1-C3 alkyl or cyclopropyl group. R 3f1 It is a C1-C3 alkyl group or a hydrogen atom. R 3g1 It consists of a C1-C3 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom. R 5a It is a C1-C3 alkyl group. R 7a It is a C1-C3 alkyl group or a hydrogen atom. R 8a The following are possible meanings: a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyclopropyl and halogen atoms}; a phenyl group {the phenyl group may be substituted by one or more substituents selected from the group consisting of cyano, trifluoromethyl and halogen atoms}; a 5- or 6-membered aromatic heterocyclic group {the 5- or 6-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of cyano, trifluoromethyl and halogen atoms}; or a cyclopropyl group or a hydrogen atom. R 10 It is a C1-C3 alkyl group or a hydrogen atom. R 22a R 22f and R E1 They may be identical or different from each other, and are C1-C3 alkyl groups or hydrogen atoms that can be substituted by one or more halogen atoms. R 23 and R E2 The same or different from each other, being C1-C3 alkyl, cyclopropyl, or hydrogen atoms that can be substituted by one or more halogen atoms. R 3 It can be a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkylmethyl group, a phenylmethyl group, a pyridylmethyl group, a cyanomethyl group, a tetrahydrofuranylmethyl group, a cyclopropyl group, or a hydrogen atom. R 4 C1-C3 alkyl, phenyl, or pyridyl groups that can be substituted with one or more halogen atoms {the phenyl and pyridyl groups can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkyl, cyano, and halogen atoms that can be substituted with one or more halogen atoms}, OR 18 S(O)m R 29 NR 7b R 8b C(O)NR 7b R 8b NR 9b C(O)R 5b NR 9b C(O)OR 6b , mercapto group, cyclopropyl group, halogen atom or hydrogen atom, R 18 It is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. R 29 It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 5b It is a C1-C3 alkyl 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-C3 alkyl groups that can be substituted with one or more halogen atoms, C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, cyano groups and halogen atoms}, pyridyl groups, or C3-C6 cycloalkyl groups. R 6b It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 7b It is a C1-C3 chain hydrocarbon group, cyano group, or hydrogen atom that can be replaced by one or more halogen atoms. R 8b The following are C1-C3 chain hydrocarbon groups that can be substituted with one or more halogen atoms, phenyl groups {the phenyl group can be substituted with one or more substituents selected from the group consisting of cyano, trifluoromethyl, and halogen atoms}, 5- or 6-membered aromatic heterocyclic groups {the 5- or 6-membered aromatic heterocyclic groups can be substituted with one or more substituents selected from the group consisting of cyano, trifluoromethyl, and halogen atoms}, cyclopropyl groups, or hydrogen atoms. R 9b It consists of a C1-C3 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom. R 3 and R 4 With R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form a group represented by formula A1-1-1, a group represented by formula A5-2-1, or a group represented by formula A6-2 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R 1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 5] X is NR 11 C(O)R12 NR 11 C(O)NR 12 R 13 , or NR 11 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 groups substituted by one or more substituents selected from the group consisting of cyano and halogen atoms, cyclopropyl groups substituted by one or more cyano groups, OR} 3aa The ring members of the heterocycle, in addition to the carbon atom, include one, two, or three heteroatoms selected from the group consisting of N, O, and S. R 3aa It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 11 It is a C1-C3 alkyl, C1-C2 alkylsulfonyl, OCH3, C(O)R that can be substituted by one or more substituents selected from group F. 14 C(O)OR 14 or hydrogen atoms, R 12 The group is phenyl, pyrazolyl, or pyridyl {the phenyl, pyrazolyl, or pyridyl 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 cyano and halogen atoms}, cyclopropyl group substituted with one or more cyano groups, OR 3ab S(O) m R 3ka , cyano group and halogen atom}, R 13 It is a C1-C3 alkyl group or a hydrogen atom. R 14 It is a C1-C4 alkyl or cyclopropyl group. R 3ab It can be a C1-C3 alkyl group that can be substituted with one or more halogen atoms, a cyclopropyl group that can be substituted with one or more cyano groups, or a hydrogen atom. R 3ka It is a C1-C3 alkyl group or a cyclopropyl group that can be substituted with one or more halogen atoms. Group F is composed of cyclopropyl, phenyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl and cyano.

[0021] [4] The compound or its N oxide as described in [1] or [2], wherein, in formula (I), Z stands for oxygen atom. L represents a single bond. R 1 It is a methyl or 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}, R 3 It consists of C1-C3 chain hydrocarbon groups or hydrogen atoms. R 4 A C1-C3 alkyl, phenyl, pyridyl, or pyrimidinyl group that can be substituted with one or more halogen atoms {the phenyl, pyridyl, and pyrimidinyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkyl, cyano, and halogen atoms that can be substituted with one or more halogen atoms}, SR 29 NR 7b R 8b Cyclopropyl, cyano, or hydrogen atom R 29 It is a C1-C3 alkyl group. R 7b It is a hydrogen atom. R 8b It is a C1-C3 chain hydrocarbon group. X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 X 1 , X 1 The quinazolinyl group can be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, cyclopropyl which can be substituted by cyano, and halogen atoms. R 11 It is a methyl or hydrogen atom. R 12 The group is phenyl or pyrazolyl {the phenyl group and the pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: methyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl which may be substituted by cyano, and halogen atoms}. R 13 It is a hydrogen atom.

[0022] [5] A composition for controlling harmful arthropods, comprising an inactive carrier and any one of [1] to [4] or its N oxide.

[0023] [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.

[0024] [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 [6] is applied to the harmful arthropod or its habitat.

[0025] [8] A seed or vegetative reproductive organ containing an effective amount of any one of [1] to [4] or its N oxide, or an effective amount of the composition described in [6].

[0026] Invention Effects This invention enables the prevention and control of harmful arthropods. Detailed Implementation

[0027] The substituents in this invention will be explained.

[0028] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms.

[0029] When the substituent has two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different.

[0030] 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.

[0031] The term "chain hydrocarbon group" refers to alkyl, alkenyl, or alkynyl groups.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentoxy, and hexyloxy.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] The term "phenyl C1-C3 alkyl" refers to a phenyl moiety that can be substituted by one or more substituents selected from group B. Examples of substituents include phenylmethyl, 2-fluorobenzyl, 4-chlorobenzyl, 4-(trifluoromethyl)benzyl, and 2-[4-(trifluoromethyl)phenyl]ethyl.

[0040] Examples of 3-6 membered non-aromatic heterocyclic groups include oxobutyranyl, tetrahydrofuranyl, tetrahydropyranyl, and morpholinyl.

[0041] Examples of alkyl sulfonyl groups include methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, and isopropyl sulfonyl.

[0042] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0043] Examples of cycloalkylmethyl groups include cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, and cyclohexylmethyl.

[0044] 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.

[0045] 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.

[0046] Examples of compounds N in this invention include the following compounds.

[0047] [Method 1] In compound N of the present invention, R 3 The C1-C3 chain hydrocarbon group {this C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkoxy groups substituted by one or more halogen atoms, C3-C6 cycloalkyl groups substituted by one or more halogen atoms or cyano groups, phenyl groups substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic groups substituted by one or more substituents selected from group B, 3-6-membered non-aromatic heterocyclic groups, cyano groups and halogen atoms}, C(O)R 5 Cyclopropyl groups or hydrogen atoms that can be substituted by one or more halogen atoms or cyano groups, R 5 A compound consisting of a C1-C6 chain hydrocarbon group, phenyl group, cyclopropyl group, or hydrogen atom that can be replaced by one or more halogen atoms.

[0048] [Method 2] In compound N of the present invention, R 3 Compounds that are C1-C3 alkyl, 2-propenyl, 2-propynyl, C3-C6 cycloalkylmethyl, phenylmethyl, pyridylmethyl, cyanomethyl, tetrahydrofuranylmethyl, cyclopropyl or hydrogen atoms.

[0049] [Method 3] In compound N of the present invention, R 4 The C1-C3 chain hydrocarbon group {this C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of: cyclopropyl, phenyl group which may be substituted by one or more substituents selected from group B, 5 or 6-membered aromatic heterocyclic group which may be substituted by one or more substituents selected from group B, cyano group and halogen atom}, OR 18 S(O) m R 29 NR 7b R 8b C(O)NR 7b R 8b NR 9b C(O)R 5b NR9b C(O)OR 6b NR 9 C(O)NR 7 R 8 , cyclopropyl, halogen atom or hydrogen atom, R 18 R is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 29 R is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. 5 R is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, a phenyl group, a pyridyl group, a C3-C6 cycloalkyl group, or a hydrogen atom that can be substituted with one or more substituents selected from group B. 6 R is a C1-C3 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 C3-C6 cycloalkyl group, or a hydrogen atom. 7 and R 7b Identical or different from each other, it is a C1-C3 chain hydrocarbon group, C3-C6 cycloalkyl group, cyano group, or hydrogen atom that can be substituted by one or more halogen atoms, R 8 and R 8b The same or different from each other, is a C1-C3 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, a 5 or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B, a C3-C6 cycloalkyl group, or a hydrogen atom, R 9 and R 9b Compounds that are the same as or different from each other, and are C1-C3 chain hydrocarbon groups, C3-C6 cycloalkyl groups, or hydrogen atoms that can be replaced by one or more halogen atoms.

[0050] [Method 4] In compound N of the present invention, R 4 It is a compound of C1-C3 alkyl group that can be substituted with one or more halogen atoms, phenyl group that can be substituted with one or more substituents selected from group B, pyridyl group, cyclopropyl group or hydrogen atom that can be substituted with one or more substituents selected from group B.

[0051] [Method 5] In Method 3, R 3 The C1-C3 chain hydrocarbon group {this C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of: C1-C3 alkoxy groups substituted by one or more halogen atoms, C3-C6 cycloalkyl groups substituted by one or more halogen atoms or cyano groups, phenyl groups substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic groups substituted by one or more substituents selected from group B, 3-6-membered non-aromatic heterocyclic groups, cyano groups and halogen atoms}, C(O)R 5 Compounds that can be replaced by one or more halogen atoms or cyano groups, or cyclopropyl groups or hydrogen atoms.

[0052] [Method 6] In Method 3, R 3 Compounds that are C1-C3 alkyl, 2-propenyl, 2-propynyl, C3-C6 cycloalkylmethyl, phenylmethyl, pyridylmethyl, cyanomethyl, tetrahydrofuranylmethyl, cyclopropyl or hydrogen atoms.

[0053] [Method 7] In Method 1, R 4 It is a compound of C1-C3 alkyl group that can be substituted with one or more halogen atoms, phenyl group that can be substituted with one or more substituents selected from group B, pyridyl group, cyclopropyl group or hydrogen atom that can be substituted with one or more substituents selected from group B.

[0054] [Method 8] In Method 2, R 4 It is a compound of C1-C3 alkyl group that can be substituted with one or more halogen atoms, phenyl group that can be substituted with one or more substituents selected from group B, pyridyl group, cyclopropyl group or hydrogen atom that can be substituted with one or more substituents selected from group B.

[0055] [Method 9] In compound N of the present invention, R 3 and R 4 With R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form the following groups: A1-1, A4-3, A5-2, A5-3, A6-1, or A7-1 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R 1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 6] R 25 It is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, a C1-C3 alkoxy group that can be substituted with one or more halogen atoms, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 , cyano, halogen atom or hydrogen atom, R 26 R represents a C1-C3 alkyl, cyclopropyl, or hydrogen atom that can be substituted by one or more halogen atoms. 2a R2b R 2c R 2d R 2g R 2h R 2i R 2j R 2k R 2l R 2m R 2n R 2o R 2p R 2q R 2r R 2s R 2t R 2u and R 2v The same or different from each other, being C1-C3 alkyl groups that can be substituted with one or more halogen atoms, C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, or C(O)R groups. 5 C(O)OR 6 C(O)NR 7 R 8 NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 Compounds containing cyano, halogen, or hydrogen atoms.

[0056] [Method 10] In compound N of the present invention, R 3 and R 4 With R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form the following groups: A1-1, A4-3, A5-2, A5-3, A6-2, or A7-2 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R 1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 7] R 25 R can be a methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano, halogen atom, or hydrogen atom. 26 R is a C1-C3 alkyl group or a hydrogen atom. 2a R 2b R 2c R 2dR 2g and R 2h Compounds that are the same or different from each other, and are composed of methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano, halogen, or hydrogen atoms.

[0057] [Method 11] 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0058] [Method 12] In the compound N of the present invention, L is a single bond.

[0059] [Method 13] In Method 1, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, where n is 1, 2 or 3.

[0060] [Method 14] In Method 2, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0061] [Method 15] In Method 3, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0062] [Method 16] In Method 4, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0063] [Method 17] In Method 5, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0064] [Method 18] In Method 6, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0065] [Method 19] In Method 7, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0066] [Method 20] In Method 8, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0067] [Method 21] In Method 9, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0068] [Method 22] In Method 10, 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 or hydrogen atoms that can be replaced by one or more halogen atoms, with n being 1, 2 or 3.

[0069] [Method 23] In Method 1, L is a compound with a single bond.

[0070] [Method 24] In Method 2, L is a compound with a single bond.

[0071] [Method 25] In Method 3, L is a compound with a single bond.

[0072] [Method 26] In Method 4, L is a compound with a single bond.

[0073] [Method 27] In Method 5, L is a compound with a single bond.

[0074] [Method 28] In Method 6, L is a compound with a single bond.

[0075] [Method 29] In Method 7, L is a compound with a single bond.

[0076] [Method 30] In Method 8, L is a compound with a single bond.

[0077] [Method 31] In Method 9, L is a compound with a single bond.

[0078] [Method 32] In Method 10, L is a compound with a single bond.

[0079] [Method 33] 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.

[0080] [Method 34] In compound N of the present invention, R 1 Compounds containing methyl groups.

[0081] [Method 35] 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.

[0082] [Method 36] 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.

[0083] [Method 37] 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.

[0084] [Method 38] 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.

[0085] [Method 39] In Method 5, R 1It 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.

[0086] [Method 40] 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.

[0087] [Method 41] 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.

[0088] [Method 42] 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.

[0089] [Method 43] 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.

[0090] [Method 44] 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.

[0091] [Method 45] 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.

[0092] [Method 46] In Method 12, 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.

[0093] [Method 47] In Method 13, 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.

[0094] [Method 48] In Method 14, 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.

[0095] [Method 49] In Method 15, 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.

[0096] [Method 50] In Method 16, 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.

[0097] [Method 51] In Method 17, 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.

[0098] [Method 52] In Method 18, 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.

[0099] [Method 53] In Method 19, 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.

[0100] [Method 54] In Method 20, 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.

[0101] [Method 55] In Method 21, 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.

[0102] [Method 56] In Method 22, 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.

[0103] [Method 57] In Method 23, 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.

[0104] [Method 58] In Method 24, 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.

[0105] [Method 59] In Method 25, 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.

[0106] [Method 60] In Method 26, 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.

[0107] [Method 61] In Method 27, 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.

[0108] [Method 62] In Method 28, 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.

[0109] [Method 63] In Method 29, 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.

[0110] [Method 64] In Method 30, 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.

[0111] [Method 65] In Method 31, 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.

[0112] [Method 66] In Method 32, 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.

[0113] [Method 67] In Method 1, R 1 Compounds containing methyl groups.

[0114] [Method 68] In Method 2, R 1 Compounds containing methyl groups.

[0115] [Method 69] In Method 3, R 1 Compounds containing methyl groups.

[0116] [Method 70] In Method 4, R 1 Compounds containing methyl groups.

[0117] [Method 71] In Method 5, R 1 Compounds containing methyl groups.

[0118] [Method 72] In Method 6, R 1 Compounds containing methyl groups.

[0119] [Method 73] In Method 7, R 1 Compounds containing methyl groups.

[0120] [Method 74] In Method 8, R 1 Compounds containing methyl groups.

[0121] [Method 75] In Method 9, R 1 Compounds containing methyl groups.

[0122] [Method 76] In Method 10, R 1 Compounds containing methyl groups.

[0123] [Method 77] In Method 11, R 1 Compounds containing methyl groups.

[0124] [Method 78] In Method 12, R 1 Compounds containing methyl groups.

[0125] [Method 79] In Method 13, R 1 Compounds containing methyl groups.

[0126] [Method 80] In Method 14, R 1 Compounds containing methyl groups.

[0127] [Method 81] In Method 15, R 1 Compounds containing methyl groups.

[0128] [Method 82] In Method 16, R 1 Compounds containing methyl groups.

[0129] [Method 83] In Method 17, R 1 Compounds containing methyl groups.

[0130] [Method 84] In Method 18, R 1 Compounds containing methyl groups.

[0131] [Method 85] In Method 19, R 1 Compounds containing methyl groups.

[0132] [Method 86] In Method 20, R 1 Compounds containing methyl groups.

[0133] [Method 87] In Method 21, R 1 Compounds containing methyl groups.

[0134] [Method 88] In Method 22, R 1 Compounds containing methyl groups.

[0135] [Method 89] In Method 23, R 1 Compounds containing methyl groups.

[0136] [Method 90] In Method 24, R 1 Compounds containing methyl groups.

[0137] [Method 91] In Method 25, R 1 Compounds containing methyl groups.

[0138] [Method 92] In Method 26, R 1 Compounds containing methyl groups.

[0139] [Method 93] In Method 27, R 1 Compounds containing methyl groups.

[0140] [Method 94] In Method 28, R 1Compounds containing methyl groups.

[0141] [Method 95] In Method 29, R 1 Compounds containing methyl groups.

[0142] [Method 96] In Method 30, R 1 Compounds containing methyl groups.

[0143] [Method 97] In Method 31, R 1 Compounds containing methyl groups.

[0144] [Method 98] In Method 32, R 1 Compounds containing methyl groups.

[0145] [Method 99] In compound N of the present invention, R 1 R is a C1-C3 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. 3 R is a C1-C3 alkyl group or a hydrogen atom. 4 A compound is a C1-C3 alkyl or hydrogen atom that can be replaced by one or more halogen atoms, where Z is an oxygen atom and L is a single bond.

[0146] [Method 100] In any of Methods 1 to 99 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 3b1 C(O)R 3c1 C(O)NR 3f1 R 3g1 S(O) m R 3k , cyano group and halogen atom}, C(O)NR 7a R 8a NR 19 C(O)R 20 NR 19 C(O)OR 20 NR 19 C(O)NR 20 R 21 OR 18 The 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 (Indicates the bonding site with a carbon atom). [Chemical Formula 8] R 18 R is a C1-C6 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. 2 For NR 19 C(O)R 20 And R 19 and R 20 With R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 represented by formula E4-1, formula E4-2, formula E4-4, formula E4-5, or formula E4-6. [Chemical Formula 9] R 2 For NR 19 C(O)OR 20 And R 19 and R 20 With R 19 The bonded nitrogen atom and R 20 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 E5-1, formula E5-2, formula E5-5, formula E5-6, formula E5-7, formula E5-8, or formula E5-10. [Chemical Formula 10] R 2 For NR 19 C(O)NR 20 R 21 And R 19 and R 20 With R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 2It can form a group represented by formula E6-1, a group represented by formula E6-5, a group represented by formula E6-6, or a group represented by formula E6-7. [Chemical Formula 11] R E1 R is a C1-C6 chain hydrocarbon group, halogen atom, or hydrogen atom that can be replaced by one or more halogen atoms. 23 and R E2 They are the same or different from each other, and are C1-C6 chain hydrocarbon groups that can be substituted by one or more substituents selected from group C, cyclopropyl groups that can be substituted by one or more substituents selected from group E, or compounds containing hydrogen atoms.

[0147] [Method 101] In any of Methods 1 to 99 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; ... 3b1 C(O)R 3c1 C(O)NR 3f1 R 3g1 S(O) m R 3k , cyano group and halogen atom}, C (=NOR) 10 R 5a C (=NOR) 10 (NR) 7 R 8 ), 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.

[0148] [Method 102] In any of Methods 1 to 99 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} 3b1 C(O)R 3c1 C(O)NR 3f1 R 3g1 Compounds containing cyano groups and halogen atoms.

[0149] [Method 103] In any of Methods 1 to 99 or Compound N of the present invention, X is NR.11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 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 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3aa NR 3b C(O)R 3c N=S(O) p R 3h R 3i C(O)NR 3f R 3g S(O)2NR 3f R 3g NR 3b S(O) m R 3k S(O) m R 3k , cyano group and halogen atom}, R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The group is phenyl or pyridyl {the phenyl and pyridyl groups may be substituted by substituents selected from the group consisting of: C1-C3 chain hydrocarbon {the C1-C3 chain hydrocarbon 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 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3aa and R 3ab The same or different from each other, is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 3b R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3c R is a C1-C3 chain hydrocarbon group that can be substituted with one or more halogen atoms, a cyclopropyl 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 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B. 3f R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3g R is a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a cyclopropyl group that can be substituted by one or more halogen atoms. 3h R is a C1-C3 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, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3i R is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3k and R 3ka The 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, or cyclopropyl groups that can be substituted with one or more halogen atoms.

[0150] [Method 104] In Method 100, X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 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 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3aa NR 3b C(O)R 3c N=S(O)p R 3h R 3i C(O)NR 3f R 3g S(O)2NR 3f R 3g NR 3b S(O) m R 3k S(O) m R 3k , cyano group and halogen atom}, R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The group is phenyl or pyridyl {the phenyl and pyridyl groups may be substituted by substituents selected from the group consisting of: C1-C3 chain hydrocarbon {the C1-C3 chain hydrocarbon 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 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3aa and R 3ab The same or different from each other, is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 3b R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3c R is a C1-C3 chain hydrocarbon group that can be substituted with one or more halogen atoms, a cyclopropyl 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 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B. 3fR is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3g R is a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a cyclopropyl group that can be substituted by one or more halogen atoms. 3h R is a C1-C3 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, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3i R is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3k and R 3ka The 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, or cyclopropyl groups that can be substituted with one or more halogen atoms.

[0151] [Method 105] In Method 101, X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 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 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3aa NR 3b C(O)R 3c N=S(O) p R 3h R 3i C(O)NR 3f R 3g S(O)2NR 3f R 3g NR 3b S(O) m R 3k S(O) m R 3k , cyano group and halogen atom}, R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14or hydrogen atom, R 12 The group is phenyl or pyridyl {the phenyl and pyridyl groups may be substituted by substituents selected from the group consisting of: C1-C3 chain hydrocarbon {the C1-C3 chain hydrocarbon 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 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3aa and R 3ab The same or different from each other, is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 3b R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3c R is a C1-C3 chain hydrocarbon group that can be substituted with one or more halogen atoms, a cyclopropyl 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 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B. 3f R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3g R is a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a cyclopropyl group that can be substituted by one or more halogen atoms. 3h R is a C1-C3 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, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3i R is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3k and R 3ka The 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, or cyclopropyl groups that can be substituted with one or more halogen atoms.

[0152] [Method 106] In Method 102, X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 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 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3aa NR 3b C(O)R 3c N=S(O) p R 3h R 3i C(O)NR 3f R 3g S(O)2NR 3f R 3g NR 3b S(O) m R 3k S(O) m R 3k , cyano group and halogen atom}, R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The group is phenyl or pyridyl {the phenyl and pyridyl groups may be substituted by substituents selected from the group consisting of: C1-C3 chain hydrocarbon {the C1-C3 chain hydrocarbon 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 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3aa and R 3ab The same or different from each other, is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom, R 3b R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3c R is a C1-C3 chain hydrocarbon group that can be substituted with one or more halogen atoms, a cyclopropyl 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 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more substituents selected from group B. 3f R is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 3g R is a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a cyclopropyl group that can be substituted by one or more halogen atoms. 3h R is a C1-C3 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, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3i R is a C1-C3 alkyl group that can be substituted with one or more halogen atoms, or a cyclopropyl group that can be substituted with one or more halogen atoms. 3k and R 3ka The 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, or cyclopropyl groups that can be substituted with one or more halogen atoms.

[0153] [Method 107] In any of Methods 1 to 99 or Compound N of the present invention, X is NR. 11 C(O)R 12 R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R12 The phenyl or pyridyl group {the phenyl and pyridyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3ab R is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom. 3ka It is a compound of C1-C3 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 cyclopropyl group that can be substituted with one or more halogen atoms.

[0154] [Method 108] In Method 100, X is NR 11 C(O)R 12 R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The phenyl or pyridyl group {the phenyl and pyridyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3ab R is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom. 3ka It is a compound of C1-C3 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 cyclopropyl group that can be substituted with one or more halogen atoms.

[0155] [Method 109] In Method 101, X is NR 11 C(O)R 12 R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The phenyl or pyridyl group {the phenyl and pyridyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3abR is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom. 3ka It is a compound of C1-C3 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 cyclopropyl group that can be substituted with one or more halogen atoms.

[0156] [Method 110] In Method 102, X is NR 11 C(O)R 12 R 11 It is a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group F, a C1-C3 alkylsulfonyl group that can be substituted by one or more halogen atoms, or OR 15 C(O)R 14 C(O)OR 14 or hydrogen atom, R 12 The phenyl or pyridyl group {the phenyl and pyridyl group may be substituted by one or more substituents selected from the group consisting of: C1-C3 chain hydrocarbon group {the C1-C3 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, cyclopropyl group {the cyclopropyl group may be substituted by one or more substituents selected from the group consisting of cyano and halogen atoms}, OR 3ab S(O) m R 3ka , cyano group and halogen atom}, R 14 The phenyl group is a C1-C4 chain hydrocarbon group that can be substituted with one or more halogen atoms, or a phenyl group {the phenyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, C1-C3 alkyl groups, cyano groups and halogen atoms that can be substituted with one or more halogen atoms}, cyclopropyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms, R 15 R is a C1-C6 chain hydrocarbon group that can be substituted by one or more halogen atoms, a phenylmethyl group {the phenyl portion of the phenylmethyl group can be substituted by one or more halogen atoms}, or a hydrogen atom. 3ab R is a cyclopropyl group that can be substituted by one or more substituents selected from the group consisting of halogen atoms and cyano groups, a C1-C3 chain hydrocarbon group that can be substituted by one or more halogen atoms, or a hydrogen atom. 3ka It is a compound of C1-C3 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 cyclopropyl group that can be substituted with one or more halogen atoms.

[0157] [Method 111] In any of Methods 1 to 99 or Compound N of the present invention, X is NR. 11 C(O)R12 R 11 For hydrogen atoms, R 12 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}.

[0158] [Method 112] In Method 100, X is NR 11 C(O)R 12 R 11 For hydrogen atoms, R 12 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}.

[0159] [Method 113] In Method 101, X is NR 11 C(O)R 12 R 11 For hydrogen atoms, R 12 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}.

[0160] [Method 114] In Method 102, X is NR 11 C(O)R 12 R 11 For hydrogen atoms, R 12 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}.

[0161] [Method 115] In any of Methods 1 to 99 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.

[0162] Next, the method for manufacturing the compound of the present invention will be described.

[0163] Manufacturing Method 1 The compound shown in formula (Ia) (hereinafter referred to as compound (Ia)) can be produced by reacting the compound shown in formula (M-6) (hereinafter referred to as compound (M-6)) with the compound shown in formula (Md) (hereinafter referred to as compound (Md)).

[0164] [Chemical Formula 12] [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 tetrahydrofuran (THF), 1,4-dioxane, 1,2-dimethoxyethane (DME), methyl tert-butyl ether (MTBE), diethyl ether, and other ethers; halogenated hydrocarbons such as dichloromethane and chloroform; aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile; dimethylformamide (DMF); N-methylpyrrolidone (NMP); water and mixtures of two or more of these solvents.

[0165] 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). 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 (M-6).

[0166] In the reaction, compound (Md) is usually used in a ratio of 1 to 2 moles relative to 1 mole of compound (M-6).

[0167] 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.

[0168] 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 (Ia).

[0169] The compound (Md) is a commercially available compound or can be manufactured using known methods.

[0170] Manufacturing Method 2 Compound (Ia) can also be prepared by reacting compound (M-6) with the compound shown in formula (Me) (hereinafter referred to as compound (Me)) in the presence of a condensing agent.

[0171] [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 used in the reaction include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); nitriles; nonprotic polar solvents such as NMP, DMF, and dimethyl sulfoxide (hereinafter referred to as DMSO); 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.

[0172] Examples of condensing agents used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0173] 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 (M-6).

[0174] 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 (M-6).

[0175] In the reaction, the compound (Me) is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (M-6), and the condensing agent is usually used in a ratio of 1 to 5 moles.

[0176] 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.

[0177] 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 (Ia).

[0178] The compound (Me) is a commercially available compound or can be manufactured using known methods.

[0179] Manufacturing method 3 Compound (Ia) can also be produced by reacting the compound shown in formula (M-5) (hereinafter referred to as compound (M-5)) with the compound shown in formula (Mg) (hereinafter referred to as compound (Mg)) in the presence of an acid.

[0180] [Chemical Formula 14] [In the formula, Boc represents tert-butyloxycarbonyl, X] C [This indicates a leaving group such as a chlorine atom; other symbols have the same meaning as described above.] The reaction is usually carried out in a solvent. Examples of solvents include ethers; halogenated hydrocarbons; aromatic hydrocarbons; nitriles; DMF; NMP; water; and mixtures of two or more of them.

[0181] 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.

[0182] The reaction can be carried out, for example, by first mixing the compound (M-5) with an acid, then removing the acid by distillation, and then mixing the compound (Mg) again.

[0183] 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 (M-5).

[0184] In the reaction, the compound (Mg) is usually used in a ratio of 1 to 2 moles relative to 1 mole of the compound (M-5), and the acid is usually used in a ratio of 1 to 100 moles.

[0185] 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.

[0186] 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 (Ia).

[0187] The compound (Mg) is a commercially available compound or can be manufactured using known methods.

[0188] Manufacturing method 4 Compound (Ia) can also be produced by reacting compound (M-5) with compound (Me) in the presence of a condensing agent and an acid.

[0189] [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 include ethers; halogenated hydrocarbons; aromatic hydrocarbons; nitriles; esters; aprotic polar solvents; nitrogen-containing aromatic compounds and mixtures of two or more of them.

[0190] Examples of acids used in the reaction include trifluoroacetic acid and hydrogen chloride.

[0191] When using hydrogen chloride, solutions of hydrogen chloride, such as hydrochloric acid or hydrogen chloride / methanol solution, can be used for the reaction.

[0192] The reaction can be carried out, for example, by first mixing the compound (M-5) with an acid, then removing the acid by distillation, and then mixing the compound (Me) with a condensing agent.

[0193] Examples of condensing agents used in the reaction include carbodiimides such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide.

[0194] 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 (M-5).

[0195] 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 (M-5).

[0196] In the reaction, relative to 1 mole of compound (M-5), 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.

[0197] 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.

[0198] 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 (Ia).

[0199] The compound (Me) is a commercially available compound or can be manufactured using known methods.

[0200] Manufacturing method 5 The compound shown in formula (I) (i.e., the compound N of the present invention) can be produced by reacting the compound shown in formula (M-10) (hereinafter referred to as compound (M-10)) with the compound shown in formula (Mc) (hereinafter referred to as compound (Mc)) in the presence of a metal catalyst.

[0201] [Chemical Formula 16] [In the formula, X]A M represents a chlorine atom, a bromine atom, or an iodine atom. A The symbol represents 9-boronbicyclo[3.3.1]nonane-9-yl, dihydroxyboronyl, 4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl, or tributyltinyl. For other symbols, the 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.

[0202] 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.

[0203] In the reaction, ligands, bases and / or inorganic halides may also be used as needed.

[0204] 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.

[0205] Examples of bases include alkali metal carbonates and organic bases.

[0206] 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.

[0207] In the reaction, compound (Mc) is typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-10), and metal catalysts are typically used in a ratio of 0.01 to 0.5 moles. When ligands are used in the reaction, the ligands are typically used in a ratio of 0.01 to 1 mole relative to 1 mole of compound (M-10). 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 (M-10). When inorganic halides are 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 (M-10).

[0208] 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.

[0209] 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.

[0210] The compound (Mc) is a commercially available compound or can be manufactured using known methods.

[0211] Reference manufacturing method 1 Compound (M-6) can be produced from compound (M-5).

[0212] [Chemical Formula 17] [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.

[0213] Compound (M-6) 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.

[0214] Reference manufacturing method 2 Compound (M-5) can be prepared by reacting the compound of formula (M-4) (hereinafter referred to as compound (M-4)) with compound (Mc) in the presence of a metal catalyst.

[0215] [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 (M-4) instead of compound (M-10) according to manufacturing method 5.

[0216] Reference manufacturing method 3 Compound (M-4) can be produced by reacting the compound of formula (M-3a) (hereinafter referred to as compound (M-3a)) with a halogenating agent.

[0217] [Chemical Formula 19] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols such as methanol and ethanol (hereinafter referred to as alcohols); nitriles; ethers; aromatic hydrocarbons; aprotic polar solvents; halogenated hydrocarbons; acetic acid; water; and mixtures of two or more of them.

[0218] Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide.

[0219] 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 (M-3a).

[0220] In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles relative to 1 mole of compound (M-3a).

[0221] 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.

[0222] 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 (M-4).

[0223] Reference manufacturing method 4 Compound (M-3a) can be prepared by reacting the compound of formula (M-2a) (hereinafter referred to as compound (M-2a)) with the compound of formula (Mb) (hereinafter referred to as compound (Mb)) in the presence of a base.

[0224] [Chemical Formula 20] [In the formula, X] B [These symbols represent leaving groups such as bromine and iodine atoms; 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; aromatic hydrocarbons; nitriles; aprotic polar solvents; and mixtures of two or more of them.

[0225] Examples of bases used in reactions include alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides); alkali metal carbonates; and organic bases.

[0226] In the reaction, compound (Mb) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (M-2a), and the base is usually used in a ratio of 1 to 5 moles.

[0227] 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.

[0228] 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 (M-3a).

[0229] The compound (Mb) is a commercially available compound or can be manufactured using known methods.

[0230] Reference manufacturing method 5 Compound (M-4) can also be prepared by reacting compound (Mb) with compound (Mb) in the presence of a base.

[0231] [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 (M-3b) instead of compound (M-2a) according to reference manufacturing method 4.

[0232] Reference manufacturing method 6 Compound (M-4) can also be produced by reacting compound (M-2a) and compound (Mb) with a halogenating agent in the presence of a base.

[0233] [Chemical Formula 22] [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; nitriles; aprotic polar solvents; and mixtures of two or more of them.

[0234] Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, the halogenating agent is typically used in a ratio of 1 to 20 moles relative to 1 mole of compound (M-2a).

[0235] Examples of bases include alkali metal hydrides, alkali metal carbonates, and organic bases. For example, alkali metal carbonates are an example. In the reaction, the base is typically used in a ratio of 1 to 10 moles relative to 1 mole of compound (M-2a).

[0236] 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.

[0237] In terms of the reaction, it can be carried out by reacting compound (M-2a) with a halogenating agent and then mixing the resulting mixture with compound (Mb); it can also be carried out by reacting compound (M-2a) with compound (Mb) and then mixing the resulting mixture with a halogenating agent; or it can be carried out by mixing compound (M-2a), compound (Mb) with a halogenating agent.

[0238] 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 (M-4).

[0239] Reference manufacturing method 7 Compound (M-3b) can be produced by reacting compound (M-2a) with a halogenating agent.

[0240] [Chemical Formula 23] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M-2a) instead of compound (M-3a) according to reference manufacturing method 3.

[0241] Reference manufacturing method 8 The compound shown in formula (M-2b) (hereinafter referred to as compound (M-2b)) can be produced by reacting the compound shown in formula (M-2) (hereinafter referred to as compound (M-2)) with a vulcanizing agent.

[0242] [Chemical Formula 24] In the formula, R y Represents C1-C4 alkyl, cyano, halogen, or hydrogen atoms, R z [This indicates C1-C4 alkyl, C3-C6 cycloalkyl, or hydrogen atoms; other symbols have the same meaning as above.] The reaction can be carried out in a solvent or in the absence of a solvent. Examples of solvents include ethers; haloalkanes; aromatic hydrocarbons; nitriles; nitrogen-containing aromatic compounds and mixtures of two or more of them.

[0243] Examples of sulfiding agents include phosphorus pentasulfide and Lawson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphacyclobutane-2,4-disulfide).

[0244] In the reaction, the vulcanizing agent is usually used in a ratio of 1 to 3 moles relative to 1 mole of compound (M-2).

[0245] The reaction temperature is typically in the range of 0℃ to 200℃. The reaction time is typically in the range of 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 (M-2b).

[0247] Reference manufacturing method 9 Compound (M-2) can be produced by reacting the compound shown in formula (M-1) (hereinafter referred to as compound (M-1)) with the compound shown in formula (Ma) (hereinafter referred to as compound (Ma)).

[0248] [Chemical Formula 25] In the formula, R x [This indicates a C1-C4 alkyl group; other symbols have the same meaning as described 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.

[0249] In the reaction, compound (Ma) is usually used in a ratio of 1 to 5 moles relative to 1 mole of compound (M-1).

[0250] 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 hydrides; 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 the compound (M-1).

[0251] 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.

[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 (M-2).

[0253] The compound (Ma) is a commercially available compound or can be manufactured using known methods.

[0254] Compound (M-1) is known or can be prepared by known methods as described in Tetrahedron (2013) 69, 11092-11108, etc.

[0255] Reference manufacturing method 10 The compound shown in formula (M-7) (hereinafter referred to as compound (M-7)) can be produced by reacting the compound shown in formula (M-1) (hereinafter referred to as compound (M-1)) with compound (Mg).

[0256] [Chemical Formula 26] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M-1) instead of compound (M-5) according to manufacturing method 3.

[0257] Reference manufacturing method 11 The compound shown in formula (M-8a) (hereinafter referred to as compound (M-8a)) can be produced by reacting the compound shown in formula (M-7a) (hereinafter referred to as compound (M-7a)) with compound (Ma).

[0258] [Chemical Formula 27] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M-7a) instead of compound (M-1) according to reference manufacturing method 9.

[0259] Compound (M-7a) is a commercially available compound or can be manufactured using known methods.

[0260] Reference manufacturing method 12 The compound shown in formula (M-8b) (hereinafter referred to as compound (M-8b)) can be produced by reacting compound (M-8a) with a vulcanizing agent.

[0261] [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 (M-8a) instead of compound (M-2) according to reference manufacturing method 8.

[0262] Reference manufacturing method 13 The compound shown in formula (M-9) (hereinafter referred to as compound (M-9)) can be prepared by reacting compound (M-8) with compound (Mb) in the presence of a base.

[0263] [Chemical Formula 29] [In the formula, the symbols have the same meaning as in the preceding text.] The reaction can be carried out using compound (M-8) instead of compound (M-2a) according to reference manufacturing method 4.

[0264] Reference manufacturing method 14 Compound (M-10) can be produced by reacting compound (M-9) with a halogenating agent.

[0265] [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 (M-9) instead of compound (M-3a) according to reference manufacturing method 3.

[0266] 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.

[0267] The aforementioned combination or use refers to using the compound of the present invention and the ingredient simultaneously, separately, or at intervals.

[0268] 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.

[0269] 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).

[0270] 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.

[0271] Group (b) comprises nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acyl amino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiration inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid and protein synthesis inhibitors (e.g., aniline pyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-point contact active fungicides, microbial fungicides, and other fungicidal active ingredients. These ingredients are described according to the classification based on FRAC-based mechanisms of action.

[0272] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0273] Group (d) is the group containing the repellent component.

[0274] 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.

[0275] It should be noted that the abbreviation SX refers to the compound of the present invention selected from any one of the compound groups SX1 to SX1186. Furthermore, all the ingredients described below are known ingredients and can be obtained from commercially available formulations or manufactured by known methods. In the case of 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).

[0276] The combination of the component of group (a) above with the compounds of the present invention: Abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acridine lactate + SX, acynonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide Phosphide + SX, Amitraz + SX, Azadirachtin + SX, Azamethiphos + SX, Azinphos-ethyl + SX, Azinphos-methyl + SX, Azocyclotin + SX, Bark of Celastrus angulatus + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, bentioflumin + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX, bisulflufen + SX, borax + SX, boric acid acid) + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphidePhosphide + SX, Carbaryl + SX, Carbofuran + SX, Carbosulfan + SX, Cartap hydrochloride Hydrochloride + SX, Cartap + SX, Chinomethionat + SX, Chlorantraniliprole + SX, Chlordane + SX, Chlorethoxyfos + SX, Chlorfenapyr + SX, Chlorfenvinphos + SX, Chlorfluazuron + SX, Chlormephos + SX, Chlorpicrin + SX, Chlorpyrifos + SX, Chlorpyrifos-methyl + SX, Chlorafenozide + SX, Clofentezine + SX, Clothianidin + SX, Concanavalin AA) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX, cybenzoxasulfyl + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX Cyenopyrafen + SX, Cyetpyrafen + SX, Cyflumetofen + SX, Cyfluthrin + SX, Cyhalodiamide + SX, Cyhalothrin + SX, Cyhexatin + SX, Cypermethrin + SX, Cyphenothrin + SX, Cyproterone cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichlorvos + SX, dichlorvos + SX, trichlorfon + SX icofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX Disulfoton + SX, DNOC (2-methyl-4,6-dinitrophenol) + SX, doramectin + SX, dried leaves of Dryopteris filix-mas + SX, emamectin-benzoate + SX, empenthrin + SX, endosulfan + SX, EPN (O-ethyl O-(4-nitrophenyl)phenyl thiophosphonate, O-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 clitoriaternatea + SX, extract of Symphytum officinale + SX, extract of Chenopodium ambrosioides + 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, flucythrinate + SX, fluene Fluensulfone + SX, flufenoprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flumetnicam + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyridine (flup... yroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS- Omega / kappa HXTX-Hv1a peptide (GS-omega / kappa HXTX-Hv1a peptide) + SX, Halfenprox + SX, Halofenozide + SX, Heptafluthrin + SX, Heptenophos + SX, Hexaflumuron + SX, Hexythiazox + SX, Potassium salt of hop β-acidSalt of hop beta acid) + SX, hydramethylnon + SX, hydroprene + SX, imicafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflurane + SX, isoflualanam + SX, isoprocarb + SX, O-(methoxyaminothiophosphoryl)salicylic acid isopropyl ester (isop) ropyl-O-(methoxyaminothiophosphoryl)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 Lotilana + SX, Lufenuron + SX, Machine Oil + SX, Malathion + SX, Mecarbam + SX, Meperfluthrin + SX, Metaflumizone + SX, Metam + SX, Methamophos + SX, Methidathion + SX, Methiocarb + SX, Methomyl + SX, Methoprene + SX, Methoxychlor + SX, Methoxyfenozide + SX, Methyl bromide bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX, monocotophos + 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 ofChenopodium anthelminticum + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamid (on) + SX, phosphine + SX, phoxim + SX, pioxaliprole + SX, piperflanilide + SX, pirimicarb + SX, pirimitoso + SX, pirimitoso + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginatealginate + SX, prothiofos + SX, pyflubumide + SX, pymetrozine + SX, piraclofos + SX, pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyrimin ostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate Sodium metaborate + SX, spidoxamat + SX, spintoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidion + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfur + SX, sulfuryl fluoride fluoride + SX, tartaremetic + SX, tau-fluvalinate + SX, tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene components extracted from *Euphorbia milii*.The constituents of the extract of chenopodium ambrosioides (nearambrosioides) + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, tetraliprole + SX, theta-cypermethrin + SX, and thiacloprid + SX. Thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap-disodium + SX, thiosultap-monosodium + SX, tiapyrachlor + SX, tigolaner + SX, tiorantraniliprole + SX, tioxazafen + SX, tolfenpyrad + SX, tetrabromopyr... alomethrin + SX, transfluthrin + SX, triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, tyclopyrazoflor + SX, umifoxolaner + SX, vadescana + SX, vamidothion + SX, wood extract of Quassia amara + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphidephosphide) + 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 (2171099-09-3)+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)pyrrolidone-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-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, (S)-2-chloro-N-(3-ethylpent-2-yl)furan-3-carboxamide +SX, Cry1Ab protein from Bacillus thuringiensis +SX, Cry1Ac protein from Bacillus thuringiensis +SXBacillus thuringiensis Cry1Ac protein +SX, Bacillus thuringiensis Cry1Fa protein +SX, Bacillus thuringiensis Cry1A.105 protein +SX, Bacillus thuringiensis Cry2Ab protein +SX, Bacillus thuringiensis Vip3A protein +SX, Bacillus thuringiensis mCry3A protein +SX, Bacillus thuringiensis Cry3Ab protein +SX, Bacillus thuringiensis Cry3Bb protein +SX. Cry3Bb protein + SX, Cry34Ab1 / Cry35Ab1 protein from Bacillus thuringiensis + SX, Adoxophyes orana GV (granulovirus) strain BV-0001 + SX, Anticarsia monas nucleopolyhedrovirus (Anticarsiagemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus)) + SX, Autographa californica nucleopolyhedrovirus (Autographa californica MNPV) + SX, Codling moth granulovirus V15 (Cydiapomonella GV strain V15) + SX, Codling moth granulovirus V22 (Cydia pomonella GV strain V22) + SX, Cryptophorbia monas nucleopolyhedrovirus (Cryptophlebia) Leucotreta GV+SX, Dendrolimus punctatus cypovirus+SX, Cotton bollworm nucleopolyhedrovirus strain BV-0003 (Helicoverpa armigera NPV (nucleopolyhedrovirus) strain BV-0003) + SX, corn borer nucleopolyhedrovirus (Helicoverpazea NPV) + SX, gypsy moth nucleopolyhedrovirus (Lymantria dispar NPV) + SX, cabbage cutworm nucleopolyhedrovirus (Mamestra brassicae NPV) + SX, bud-headed cutworm nucleopolyhedrovirus (Mamestra configurata NPV) + SX, balsam fir sawfly nucleopolyhedrovirus (Neodiprion abietis NPV) + SX, red pine sawfly nucleopolyhedrovirus (Neodiprion lecontei NPV) + SX, pine yellow sawfly nucleopolyhedrovirus (Neodiprionsertifer NPV) + SX, locust microsporidia (Nosema) locustae+SX, Orgyia pseudotsugata NPV+SX, Pieris rapae GV+SX, Plodia interpunctella GV+SX, Spodopteraexigua MNPV+SX, Spodoptera littoralis MNPV+SX, Spodoptera litura NPV+SX, Arthrobotrysdactyloides+SX, Bacillus firmus strain GB-126+SX, Bacillus firmus strain I-1582+SX, Bacillus firmus strain NCIM2637 NCIM2637) + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX.The following strains of Bacillus sphaericus were tested: strain AQ178 + SX, serotype H5a5b of strain 2362 + SX, strain ABTS1743 of Bacillus sphaericus + SX, strain AQ52 of Bacillus thuringiensis + SX, strain BD#32 of Bacillus thuringiensis + SX, strain CR-371 of Bacillus thuringiensis + SX, and strain Aizawai of Bacillus thuringiensis + SX. The following strains were tested: ABTS-1857+SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52+SX, Bacillus thuringiensis subsp. Aizawai strain GC-91+SX, Bacillus thuringiensis subsp. Aizawai strain NB200+SX, Bacillus thuringiensis subsp. Aizawai serotype strain H-7+SX, and Bacillus thuringiensis subsp. Kurstaki strain ABTS351. strain ABTS351+SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123+SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306+SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348.The following strains were tested: * *Bacillus thuringiensis* strain EG2348 + SX; *Bacillus thuringiensis* subsp. Kurstaki strain EG7841 + SX; *Bacillus thuringiensis* subsp. Kurstaki strain EVB113-19 + SX; *Bacillus thuringiensis* subsp. Kurstaki strain F810 + SX; *Bacillus thuringiensis* subsp. Kurstaki strain HD-1 + SX; *Bacillus thuringiensis* subsp. Kurstaki strain PB54. PB54)+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11+SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12+SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176+SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002+SX, Bacillus thuringiensis subsp. Morrisoni+SX, Bacillus thuringiensis var. (colmeri)+SX, Bacillus thuringiensis var. darmstadiensis strain 24-91+SX, Bacillus thuringiensis var.The following strains are listed: *Bacillus thuringiensis* var. *galeriae* + SX, *Bacillus thuringiensis* var. *israelensis* strain BMP144 + SX, *Bacillus thuringiensis* var. *israelensis* serotype strain H-14 + SX, *Bacillus thuringiensis* var. *japonensis* strain buibui + SX, *Bacillus thuringiensis* var. *san diego* strain M-7 + SX, and *Bacillus thuringiensis* 7216 strain. var.7216)+SX, Bacillus thuringiensis var.aegypti+SX, Bacillus thuringiensis T36 var.T36) + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Decylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis+SX, Hirsutellathompsonii+SX, Lagenidium giganteum+SX,. The following strains of *Verticillium lecanii* were tested: *Lecanicillium lecanii* strain KV01 + SX, *Verticillium lecanii* conidia of strain DAOM198499 + SX, *Verticillium lecanii* conidia of strain DAOM216596 + SX, *Lecanicillium muscarium* strain Ve6 + SX, *Metarhizium anisopliae* strain F52 + SX, *Metarhizium anisopliae var. acridum* + SX, and *Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52. 5 / F52)+SX, Metarhizium flavoviride+SX, Monacrosporium phymatopagum+SX, Paecilomyces fumosoroseus Apopka strain 97+SX, Paecilomyces lilacinus strain 251+SX, Paecilomyces tenuipesstrain T1+SX, Paenibacillus popilliae+SX, Pasteuria nishizawae strain Pn1+SX, Pasteuria penetrans+SX, Pasteuria usgae+SX, Pasteuria thornei+SX, Serratia The following strains were found: *Verticillium chlamydosporium* + SX, *Verticillium lecani* strain NCIM1312 + SX, and *Wolbachia pipientis* + SX.

[0277] The combination of the 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, bifemetstrobin + 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 acid bisethylenediamine 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 extractof Reynoutria sachalinensis) + SX, extract of Tropaeolum majus + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, feneptamidoquin + SX, fenfuram + SX, fenhexamid + SX, fenopyramid + SX, fenoxanil + SX, fenpiclonil + SX, fenpicoxamid + SX, fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, fentinacetate + SX, fentin chloride + SX Triphenyltin hydroxide (fentin hydroxide) + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, fluquinconazole ( Fluquinometoate + SX, Flusilazole + SX, Flusulfamide + SX, Flutianil + SX, Flutolanil + SX, Flutriafol + SX, Fluxapyroxad + SX, Folpet + SX, Fosetyl + SX, Fosetyl-aluminium + SX, Furanylbenzimidazole (f Uberidazole + SX, furaxyl + SX, furamepyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine + triacetateTriacetate + 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 trees Quercus + 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, Octilinone + SX, Ofurace + SX, Orysastrobin + SX, Oxadixyl + SX, Oxathiapiprolin + SX, Oxine-copper + SX, Oxolinic acid + SX, Oxpoconazole + SX, Oxpoconazole fumarateFumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, penhiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX, picoxystrobin + SX, piperalin + SX Polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogen phosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, pyraclostrobin + SX, pyramet ostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridachlometyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriofenone + SX, pyrisoxazole + SX, pyroquilon + SX, Quillaja extract extract) +SX, quinconazole +SX, quinofumelin +SX, quinoxyfen +SX, quintozene +SX, saponins of Chenopodium quinoa +SX, seboctylamine +SX, sedaxane +SX, silthiofam +SX, simeconazole +SX, sodium bicarbonateHydrogencarbonate + SX, Spiroxamine + SX, Streptomycin + SX, Sulfur + SX, Tebuconazole + SX, Tebufloquin + SX, Teclofthalam + SX, Tecnazene + SX, Terbinafine + SX, Tetraconazole + SX, Thiabendazole + SX, Thifluzamide + SX, Thioprazan + SX, Thioprazan-methyl + SX, Thiram + SX, Thymol + SX, Tiadinil + SX, Tolclofos -methyl)+SX, tolfenpyrad+SX, tolprocarb+SX, tolylfluanid+SX, triadimefon+SX, triadimenol+SX, triazoxide+SX, chlorpyrifos+SX, tricyclazole+SX, triridemorph+SX, trifloxystrobin+SX, triflumizole+SX, triforine+SX, triticonazole+SX, validamycin+SX, valifenalate+SX, vinclozolin+SX, yellow mustard powder+SX, zinc thiamethoxamthiazole) + 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-(2-(2-fluorophenoxy)-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-methylformamidinium (2055756-21-1)+SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylformamidinium (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]quinazoline (1257056-97-5)+SX, (2Z)-3-amino-2-cyano-3-phenylacrylate ethyl ester (39491-78-6)+SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8)+SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4)+SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2)+SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3)+SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-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-bromophenyl) -2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0)+SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile (2018316-13-5)+SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-Difluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxylon (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-pyridol-3-yl]phenyl}methyl)amino Methyl formate (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- (1-(2,4-dichlorophenyl)-1H-pyrazole-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpentan-3-enamide (1445331-27-0)+SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazole-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, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazole- 3-[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)propionamide+SX, N-methoxy-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)propionamide+SX,4-Oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide +SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea +SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea +SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea +SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) +SX, N-[(3-hydroxy-4-methoxypyridine- [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-bromo-4 ... -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 ester) N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate)+SX, N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alanine (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl ester ((1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate)+SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide+SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)acetamide+SX, N-allyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanecarboxamide+SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanecarboxamide+SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-( (3-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,N-diethyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea4-Oxadiazol-3-yl]phenyl}methyl)urea+SX, N-methyl-N'-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidone-2-one+SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one+SX, 4-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)morpholin-3-one+SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolin-3- Ketone + 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-oxazin-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)pyrrolidine-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidine-2-one 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-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, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate +SX, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propionate +SX,4-Triazol-1-yl)ethyl propionate +SX, 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)methyl propionate +SX, 1-(2,3-dimethylpyridin-5-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-[2-(difluoromethyl)-3-methylpyridin-5-yl]-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 2,2-difluoro-N-[6-({[1-(1-methyl-1H-tetrazol-5-yl)] Benzimidazol-2-yl]oxy}methyl)pyridin-2-yl]-2-phenoxyacetamide + SX, 1-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]-1H-imidazol-5-carboxynitrile + SX, 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylic acid ethyl ester + SX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-Chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide +SX, 6-Chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide +SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole- 4-Formamide + 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-{[(oxecyclobutane-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazol-4-carboxamide +SX, 2-{[ [(oxane-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-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-2-{[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + SX, (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- ... (2-(2-chloro-4-methylphenyl)methyl)-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-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-methylpyridazine-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-hydroxy]-3-[3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxy]-5-[2 ... [Ethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2-methylpropionamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutane-2-yl)-2,2-dimethylpropionamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-Dioxo-3,6-dihydropyrimidin-1(2H)-yl}propane-2-yl)-2-methylpropionamide +SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propane-2-yl)-2-methylpropionamide +SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propane-2-yl)-2-methylpropionamide + SX, ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, ({5-[1-(2,6-difluoro-4-methoxy ... Methyl carbamate (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-2-acrylate +SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-acrylate +SX, (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-2-acrylate +SX, (Z)-2-[(3-isopropyl-1H-pyrazole-1-yl)-2-methylphenoxy]-3-methoxy-2-acrylate +SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl -3,4-Dihydroisoquinoline +SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline +SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinoline-4(3H)-one +SX, N-[2-(pyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-[2-(6-cyanopyridine) -2-yl)-2-(1-methylpyrazole-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-[(2S)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazole-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-[(2R)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazole-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-3-carboxamide +SX, N-(2,4-difluorophenyl)isoxazole-2-yl)pyridin-2-yl}-2-(1-methylpyrazole-4-yl)propyl)-5 ...4-Difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(5-methylpyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-dichlorophenyl)isoxazole-3-carboxamide + SX, 6-(2-{[5-(2,4-difluorophenyl)isoxazole-3-carbonyl]amino} -1-Methyl-1-(1-methylpyrazole-4-yl)ethyl)pyridine-3-carboxylic acid methyl ester +SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazole-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)isoxazole-3-carboxamide +SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazole-4-yl)propyl]-3-(2,4-difluorophenyl)-1,2,4-oxadiazole-5-carboxamide +SX, N-[2- [(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(5-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluorophenyl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4 ... Fluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)-1,3,4-thiadiazole-2-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,6-difluoropyridin-3-yl)-1,3,4-thiadiazole-2-carboxamide + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 DB101) + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 QST713) + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727F727)+SX, Bacillus amyloliquefaciens subsp. plantarum strain D747+SX, Bacillus licheniformis strain HB-2+SX, Bacillus licheniformis strain SB3086+SX, Bacillus pumilus strain AQ717+SX, Bacillus pumilus strain BUF-33+SX, Bacillus pumilus strain GB34+SX, Bacillus pumilus strain QST2808+SX, Bacillus simplex strain CGF2856+SX. The following strains of Bacillus subtilis were tested: simplexstrain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, and Bacillus subtilis strain HAI0404. HAI0404) + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002The following strains were tested: Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, and Burkholderia cepacia type Wisconsin strain J82. J82)+SX, Burkholderia cepacia type Wisconsinstrain M54+SX, Candida oleophila strain O+SX, Candida saitoana+SX, Chaetomium cupreum+SX, Clonostachys rosea+SX, Coniothyrium minitans strain CGMCC8325+SX, Coniothyrium minitans strain CON / M / 91-8+SX, Cryptococcus albidus+SX, Erwinia carotovora subsp. carotovora strain CGE234M403 CGE234M403) + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxastrain AC-1AC-1) + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis MA342 + SX strain MA342) + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa PF-A22UL strain + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61K61) + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum strain SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 T34) + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma DB104 + SX Trichoderma harzianum strain 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 + SX. Trichoderma harzianum strain 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, Trichodermavirens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX.

[0278] 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.

[0279] The combination of the component of group (d) above with the compounds of the present invention: Anthraquinone + SX, DEET + SX, Icaridin + SX.

[0280] 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.

[0281] 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.

[0282] 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 include *Cicadellidae* (including *maidis*, *Cofanaspectra*, and *Amrasca biguttula biguttula*); leafhoppers include *Philaenus spumarius* (including *Philaenus spumarius*); leafhoppers include *Geishadistinctissima* (including *Geishadistinctissima*); leafhoppers include *Ricania shantungensis* (including *Ricania shantungensis*); and leafhoppers include *Mahanarva posticata* and *Mahanarva fimbriolata* (including *Mahanarva posticata*).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-tailed aphid (Macrosiphum euphorbiae), eggplant ditch aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), cereal tube aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), orange aphid (Toxoptera citricida), peach pink aphid (Hyalopterus pruni), sorghum aphid (Melanaphis) The aphid family includes: *Sacchari*, *Tetraneura nigriabdominalis*, *Ceratovacuna lanigera*, *Eriosoma lanigerum*, 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).

[0283] 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 family, including grass moths such as depunctalis, sugarcane moth (Diatraea saccharalis), eggplant moth (Leucinodesorbonalis), and peach borer (Conogethes punctiferalis); and Pyralidae family, including corn borer (Elasmopalpus lignosellus), Indian grain moth (Plodia interpunctella), dark-skinned moth (Euzopherabatangensis), and powdery moth (Cadra cautella).Spodoptera exigua, Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, Spodoptera exempta, Spodoptera cosmioides, Spodoptera eridania, Agrotis ipsilon, Agrotis segetum, Autographanigrisigna, Plusia festucae, Chrysodeixis includens, Chrysodeixis Noctuidae include species such as *Trichoplusia ni* (silver-striped noctuid moth), *Trichoplusia agnata* (silver-striped noctuid moth), *Trichoplusia ni* (silver-striped noctuid moth), *Heliothis spp.* (tobacco bud noctuid moth), *Helicoverpa armigera* (cotton bollworm), *Helicoverpa zea* (grain noctuid moth), *Anticarsiagemmatalis* (bean noctuid moth), *Alabama argillacea* (cotton leaf wavy noctuid moth), and *Hydraecia immanis* (hop vine borer). Other noctuid moths include *Malacosoma neustrium* (brown tent caterpillar), *Kunugia undans* (wavy leaf moth), and *Pieris rapae* (cabbage white butterfly).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 (Homonamagnanima), apple yellow leafroller (Archips fuscocupreanus), apple leafroller (Cydia pomonella), yellow rice borer (Tetramoera schistaceana), bean shooter (Epinotia aporema), 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); Hepialidae (ghost moths); Geometridae (geomemoths); Monema flavescens (shrew moths); Limacodidae (shrew moths); Stathmopoda masinissa (shrew moths); Sphingidae (hawk moths); Nokona (shrew moths). The family Sesiidae includes species such as *feralis*, *Synanthedon hector*, and *Synanthedon tenuis*; the family Hesperiidae includes species such as *Parnara guttata*; the family Tineidae includes species such as *Tinea translucens* and *Tineola bisselliella*; and the family Eumeta minuscula and *Eumeta japonica* are bagworms.

[0284] 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.

[0285] 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*).

[0286] 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.Leaf-rolling weevils such as the Japanese apple weevil (Rhynchites heros); Tenebrionidae beetles such as the red flour beetle (Tribolium castaneum), the mixed flour beetle (Tribolium confusum), and the black fungus beetle (Alphitobius diaperinus); Coccinellidae beetles such as the eggplant ladybug (Epilachnavigintioctopunctata); Bostrychidae beetles such as the brown powder beetle (Lyctus brunneus) and the grain beetle (Rhizopertha dominica); Ptinidae beetles; Cerambycidae beetles such as the star longhorn beetle (Anoplophora malasiaca), the longhorn beetle (Migdolus fryanus), the pink-necked longhorn beetle (Aromia bungii), the gleaming star longhorn beetle (Anoplophora glabripennis), and the yellow-spotted longhorn beetle (Psacothea hilaris); and Melanotus beetle. The family Elateridae includes click beetles such as *Okinawensis*, *Agriotes fuscicollis*, *Melanotus legatus*, *Anchastus* spp., *Conoderus* spp., *Ctenicera* spp., *Limonius* spp., and *Aeolus* spp.; the family Staphylinidae includes rove beetles such as *Paederus fuscipes*; the family Dermestidae includes small round-bellied ground beetles such as *Anthrenus verbasci*, white-bellied ground beetles such as *Dermestes maculates*, and grazing ground beetles such as *Trogoderma granarium*; and the family Stegobium includes tobacco beetles and medicinal beetles. Pheasant beetles such as *paniceum* (Anobiidae); rusty grain beetles such as *Cryptolestes ferrugineus* (Laemophloeidae); Surinamese grain beetles such as *Oryzaephilus surinamensis* (Silvanidae); and rapeseed beetles such as *Brassicogethesaeneus* (Nitidulidae).

[0287] 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*.

[0288] 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.

[0289] 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.

[0290] 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).

[0291] 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).

[0292] Thysanura: Ctenolepisma villosa, Lepismasaccharina and other Lepismatidae.

[0293] 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*).

[0294] Araneae: Eutichuridae (red-clawed spiders such as Cheiracanthium japonicum); Theridiidae (ball spiders such as Latrodectus hasseltii).

[0295] Polydesmida: Oxidus gracilis, Nedyopus tambanus, and other species in the family Paradoxosomatidae.

[0296] Isopoda: Armadillidium vulgare, Armadillidiidae.

[0297] Chilopoda: Scutigeridae (e.g., Thereuonema hilgendorfi); Scolopendridae (e.g., Scolopendra subspinipes); Ethopolyidae (e.g., Bothropolys rugosus).

[0298] Gastropoda: Limacidae (including Limax marginatus and Limaxflavus); Philomycidae (including Meghimatium bilineatum); Ampullariidae (including Pomacea canaliculata); Lymnaeidae (including Austropeplea ollula).

[0299] 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*).

[0300] 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.

[0301] 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.

[0302] For the compound or composition A of this invention, it is typically mixed with non-active 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.

[0303] These formulations typically contain 0.0001 to 99% by weight of the compound or composition A of the present invention.

[0304] 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.).

[0305] 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.).

[0306] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.

[0307] 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.).

[0308] 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.

[0309] In addition, adjuvants may be used as components to enhance or assist the efficacy of the compounds of the present invention. Specifically, examples include AgriDex (registered trademark), Induce (registered trademark), Gramin S (registered trademark), Genamin T200BM (registered trademark), Silwet L77 (registered trademark), Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol Gold (registered trademark), BreakThru (registered trademark), SundanceII (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), BANOLE (registered trademark), Ochima (registered trademark), Agris (registered trademark), AMS (Ammonium Sulfate), and UAN (Urea Ammonium). Brands include Nitrate (urea ammonium nitrate), AdGreen (registered trademark), Mees (trademark), Rumba (registered trademark), Strides (registered trademark), Partner, Orix (registered trademark), Penetrator, etc.

[0310] 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.

[0311] 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.

[0312] 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).

[0313] 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.

[0314] 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.

[0315] 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.

[0316] 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.

[0317] 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.

[0318] 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. 2The 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.

[0319] In addition, the compound or composition A of the present invention can also be processed by wrapping the resin preparation into sheets or threads around the crop, laying it near the crop, or spreading it in the soil around the roots.

[0320] 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 at 1 m². 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 at an active ingredient concentration of 0.1 to 10,000 ppm. Oils, aerosols, fumigants, poison baits, etc., are applied directly.

[0321] 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.

[0322] 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.

[0323] Maize (dent, flint, soft, popcorn, glutinous, sweet, non-sweet maize), Rice (long-grain, short-grain, medium-grain, Japanese (japonica), tropical Japanese (Japanese), Indian (indica), Javanese, paddy rice, upland rice, floating rice, direct seeding, transplanting, glutinous rice), Wheat (bread wheat (durum, soft, medium, red, white), durum wheat, spelt wheat, dense-eared wheat, each type of winter wheat, each type of spring wheat), Barley (two-row barley (=brewing barley), six-row barley, naked barley, sticky barley, each type of winter barley) (Type 1, 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 Variety, Pima Variety), Soybean (Mature Seed Harvesting Variety, Pineapple Variety, Green Harvest Variety, Each with Indeterminate, Determinate, and Semi-Determinate Growth Types), Peanut, Potato (Tetraploid, Diploid, Seedling Variety), Buckwheat, Sugar Beet (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, and ornamental purposes), sugarcane, tobacco, tea trees, mulberries, nightshade vegetables (eggplant, tomato, green pepper, chili pepper, 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.), lamiaceae vegetables (purple...). Perilla, mint, basil, etc.), strawberries, sweet potatoes, Japanese yam, taro, pears (apples, European pears, Japanese pears, white pears, quince, etc.), stone fruits (peach, plum, nectarine, green plum, cherry, apricot, prune, 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.

[0324] 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.

[0325] 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.

[0326] In this specification, Me represents methyl, Et represents ethyl, Boc represents tert-butyloxycarbonyl, and Cbz represents benzyloxycarbonyl.

[0327] First, examples of manufacturing the compounds of the present invention and their manufacturing intermediates are shown.

[0328] 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.

[0329] [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].

[0330] [Table 1] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) Ionization methods: DUIS method (ESI, APCI) Manufacturing Example 1 A mixture of 0.50 g of intermediate 1-4-1, 0.35 g of 2-(tributyltinyl)pyrimidine, 0.10 g of tetra(triphenylphosphine)palladium (0), 0.04 g of copper iodide (I), 0.04 g of lithium chloride, and 4.7 mL of 1,4-dioxane was stirred at 100 °C for 18 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, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.16 g of compound 1 of the present invention.

[0331] [Chemical Formula 31] Compound 1 of this invention: 1 H-NMR (CDCl3) δ: 8.84(2H, d), 8.24(1H, s), 7.87(1H, s),7.75(2H, s), 7.25(1H, s), 5.86-5.84(1H, m), 3.61(3H, s), 2.77(3H, s), 1.54(3H, d). Manufacturing Example 2 1 mL of trifluoroacetic acid was added to a mixture of 0.20 g of intermediate 2-4-4 and 3 mL of chloroform, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated, and 2.8 mL of THF, 0.50 mL of N,N-diisopropylethylamine, and 0.16 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially, and the mixture was stirred at room temperature for 2 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 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 2 of the present invention.

[0332] [Chemical Formula 32] Compound 2 of this invention: 1H-NMR (CDCl3) δ: 8.85-8.83(2H, m), 7.87(1H, s), 7.75(2H, s), 7.23-7.22(1H, m), 5.83(1H, s), 3.61(3H, s), 2.78(3H, s), 2.63(3H,s), 1.52(3H,d). Manufacturing Example 3 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-1 instead of intermediate 2-4-4 and 3-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0333] [Chemical Formula 33] Compound 3 of this invention: 1 H-NMR (CDCl3) δ: 8.84(2H, d), 8.23(1H, s), 7.61(1H, s),7.51-7.48(3H, m), 7.24(1H, s), 5.90-5.88(1H, m), 3.60(3H, s), 2.74(3H, s),1.52(3H, d). Manufacturing Example 4 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-1 instead of intermediate 2-4-4 and 2-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0334] [Chemical Formula 34] Compound 4 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 8.22(1H, s), 7.62(1H, d),7.52(1H, t), 7.44(1H, t), 7.30(2H, t), 5.99(1H, d), 3.59(3H, s), 2.57(3H, s),1.47(3H, d). Manufacturing Example 5 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-1 instead of intermediate 2-4-4 and 4-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0335] [Chemical Formula 35] Compound 5 of this invention: 1 H-NMR (CDCl3) δ: 8.84(2H, d), 8.23(1H, s), 7.60(2H, d),7.42(2H, d), 7.24(1H, s), 5.90-5.88(1H, m), 3.60(3H, s), 2.74(3H, s), 1.52(3H, d). Manufacturing Example 6 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-2 instead of intermediate 2-4-4.

[0336] [Chemical Formula 36] Compound 6 of this invention: 1 H-NMR (CDCl3) δ: 8.87(2H, dd), 8.26(1H, d), 8.10(1H,s), 7.89(2H, t), 7.31(1H, t), 4.71(1H, s), 4.24(1H, s), 3.61(3H, s), 2.97(3H,d). Manufacturing Example 7 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-2 instead of intermediate 2-4-4 and 3-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0337] [Chemical Formula 37] Compound 7 of this invention: 1 H-NMR (CDCl3) δ: 8.86(2H, dd), 8.25(1H, d), 7.83-7.74(1H, m), 7.64-7.61(2H, m), 7.52-7.48(1H, m), 7.29(1H, t), 4.69(1H, s), 4.28(1H, s), 3.60(3H, s), 2.95(3H, d). Manufacturing Example 8 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-2 instead of intermediate 2-4-4 and 2-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0338] [Chemical Formula 38] Compound 8 of this invention: 1 H-NMR (CDCl3) δ: 8.91-8.82(2H, m), 8.25(1H, s), 7.65-7.60(2H, m), 7.53-7.41(2H, m), 7.32-7.29(1H, m), 4.24-4.21(1H, m), 3.99-3.96(1H, m), 3.59(3H, d), 3.02-2.76(3H, m). Manufacturing Example 9 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-1 instead of intermediate 2-4-4 and 4-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0339] [Chemical Formula 39] Compound 9 of this invention: 1 H-NMR (CDCl3) δ: 8.89-8.82(2H, m), 8.25(1H, d), 7.65-7.61(3H, m), 7.52(1H, d), 7.30-7.29(1H, m), 4.69(1H, s), 4.28(1H, s), 3.60(3H, s), 3.01-2.91(3H, m). Manufacturing Example 10 1 mL of trifluoroacetic acid was added to a mixture of 0.10 g of intermediate 2-4-2 and 3 mL of chloroform, and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated, and 3 mL of DMF, 0.27 mL of N,N-diisopropylethylamine, 0.09 g of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride, 0.05 g of 1-hydroxybenzotriazole, and 0.08 g of 3,5-dibromobenzoic acid were added sequentially, and the mixture was stirred at room temperature for 2 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 resulting organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.08 g of compound 10 of the present invention.

[0340] [Chemical Formula 40] Compound 10 of this invention: 1H-NMR (CDCl3) δ: 8.90-8.88(2H, m), 8.26(1H, d), 7.68(1H, d), 7.64(1H, s), 7.46(1H, s), 7.32-7.30(1H, m), 4.65(1H, s), 4.28(1H,s), 3.60(3H,s), 2.92(3H,d). Manufacturing Example 11 The following shows the compounds and their physical properties produced in accordance with Manufacturing Example 10 using 3,5-dichlorobenzoic acid instead of 3,5-dibromobenzoic acid.

[0341] [Chemical Formula 41] Compound 11 of this invention: 1 H-NMR (CDCl3) δ: 8.90-8.87(2H, m), 8.26(1H, d), 7.44(1H, d), 7.38(1H, d), 7.32-7.29(1H, m), 4.65(1H, s), 4.28(1H, s), 3.60(3H,d), 2.93(3H,d). Manufacturing Example 12 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-3 instead of intermediate 2-4-4.

[0342] [Chemical Formula 42] Compound 12 of this invention: 1 H-NMR (CDCl3) δ: 8.86(2H, s), 8.52(1H, s), 7.88(1H,s), 7.75(2H, s), 5.89(1H, s), 2.81(3H, s), 2.51(3H, s), 1.54(3H, d). Manufacturing Example 13 The following shows the compounds and their physical properties produced in accordance with Manufacturing Example 2 using 3-(trifluoromethyl)benzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0343] [Chemical Formula 43] Invented compound 13: 1H-NMR (CDCl3) δ: 8.83(2H, d), 7.61-7.60(1H, m), 7.51-7.47(3H, m), 7.21(1H, s), 5.87-5.86(1H, m), 3.59(3H, s), 2.75(3H, s), 2.62(3H, s), 1.50(3H, d). Manufacturing Example 14 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-5 instead of intermediate 2-4-4.

[0344] [Chemical Formula 44] Compound 14 of this invention: 1 H-NMR (CDCl3) δ: 8.85(2H, d), 8.23(1H, s), 7.88(1H,s), 7.76(2H, s), 7.25(1H, s), 5.85-5.84(1H, m), 4.10-4.04(2H, m), 2.78(3H,s), 1.53(3H, d), 1.47(3H, t). Manufacturing Example 15 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-6 instead of intermediate 2-4-4.

[0345] [Chemical Formula 45] Compound 15 of this invention: 1 H-NMR (CDCl3) δ: 8.93(2H, d), 8.29(1H, s), 8.20(2H,s), 8.00(1H, s), 7.46(1H, d), 7.36(1H, t), 5.23-5.21(1H, m), 3.61(3H, s),1.49(3H, d). Manufacturing Example 16 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-7 instead of intermediate 2-4-4.

[0346] [Chemical Formula 46] Compound 16 of this invention: 1H-NMR (CDCl3) δ: 8.85-8.83(2H, m), 7.87(1H, s), 7.76(2H, s), 7.24-7.22(1H, m), 5.85-5.84(1H, m), 3.61(3H, s), 2.86-2.85(2H, m),2.81(3H, s), 1.54(3H, d), 1.40-1.38(3H, m). Manufacturing Example 17 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-8 instead of intermediate 2-4-4.

[0347] [Chemical Formula 47] Compound 17 of this invention: 1 H-NMR (CDCl3) δ: 8.91(2H, d), 8.21(2H, s), 8.00(1H,s), 7.65(1H, d), 7.33(1H, t), 5.23-5.18(1H, m), 3.61(3H, s), 2.66(3H, s),1.45(3H, d). Manufacturing Example 18 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 2, using intermediate 2-4-8 instead of intermediate 2-4-4 and 3,5-dibromobenzoyl chloride instead of 3,5-bis(trifluoromethyl)benzoyl chloride.

[0348] [Chemical Formula 48] Compound 18 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 7.81(2H, d), 7.77(1H,t), 7.39(1H, d), 7.31(1H, t), 5.15-5.11(1H, m), 3.60(3H, s), 2.66(3H, s),1.41(3H, d). Manufacturing Example 19 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-9 instead of intermediate 2-4-4.

[0349] [Chemical Formula 49] Compound 19 of this invention: 1H-NMR (CDCl3) δ: 8.92(2H, d), 8.22(2H, s), 8.00(1H,s), 7.67(1H, d), 7.33(1H, dd), 5.18(1H, m), 4.19-4.10(2H, m), 2.69(3H,t),1.44(3H,d), 1.40(3H,t). Manufacturing Example 20 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-10 instead of intermediate 2-4-4.

[0350] [Chemical Formula 50] Compound 20 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, t), 8.21(2H, s), 8.01(1H,s), 7.74-7.73(1H, m), 7.32(1H, t), 5.20-5.15(1H, m), 3.78(3H, s), 2.12-2.11(1H, m), 1.38(3H, d), 1.35-1.30(1H, m), 1.30-1.24(3H, m). Manufacturing Example 21 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-11 instead of intermediate 2-4-4.

[0351] [Chemical Formula 51] Compound 21 of this invention: 1 H-NMR (CDCl3) δ: 8.92-8.91(2H, m), 8.24(2H, s), 8.01(1H, s), 7.94(1H, d), 7.34-7.33(1H, m), 5.24-5.23(1H, m), 3.61(3H, d), 2.91-2.90(2H, m), 1.48-1.43(6H, m). Manufacturing Example 22 0.20 g of intermediate 2-4-8 was added to 5.0 mL of hydrogen chloride (5-10 wt% methanol solution), and stirred at 70 °C for 4 hours. The resulting mixture was cooled to room temperature and concentrated by adding 5.8 mL of DMF, 0.52 mL of N,N-diisopropylethylamine, and 0.35 g of 4-chloro-6,8-bis(trifluoromethyl)quinazoline, and stirring at room temperature for 2 hours. Water 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. The residue was subjected to silica gel column chromatography to give 0.063 g of compound 22 of the present invention.

[0352] [Chemical Formula 52] Compound 22 of this invention: 1 H-NMR (CDCl3) δ: 8.92(2H, d), 8.70(1H, s), 8.22(2H,d), 7.59(1H, d), 7.35(1H, t), 5.54-5.52(1H, m), 3.62(3H, s), 2.71(3H, s),1.49(3H, d). Manufacturing Example 23 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 22 using intermediate 2-4-10 instead of intermediate 2-4-8.

[0353] [Chemical Formula 53] Compound 23 of this invention: 1 H-NMR (CDCl3) δ: 8.92(2H, d), 8.73(1H, s), 8.24(1H,s), 8.18(1H, s), 7.76(1H, d), 7.34(1H, t), 5.50-5.45(1H, m), 3.79(3H, s),2.17-2.14(1H, m), 1.42-1.33(4H, m), 1.41(3H, d). Manufacturing Example 24 Add 5.0 mL of hydrogen chloride (5-10 wt% methanol solution) to 0.20 g of intermediate 2-4-8 and stir at 70 °C for 4 hours. Cool the resulting mixture to room temperature and concentrate it, then add 3.0 mL of THF and 0.21 mL of triethylamine to obtain reaction solution A. Add 0.15 g of triphosgene and 0.14 mL of triethylamine to a mixture of 0.12 g of 2,4-bis(trifluoromethyl)aniline and 5.1 mL of THF, and stir at ice temperature for 1 hour to obtain a mixture. Add reaction solution A to this mixture and stir at room temperature for 3 hours. Add water to the resulting mixture and extract with ethyl acetate. Wash the obtained organic layer successively with water and saturated brine. Dry the obtained organic layer with sodium sulfate, filter, and concentrate. Perform silica gel column chromatography on the residue to obtain 0.14 g of compound 24 of the present invention.

[0354] [Chemical Formula 54] Compound 24 of this invention: 1 H-NMR (CDCl3) δ: 8.88(2H, d), 8.28(1H, d), 7.79(1H,s), 7.71(1H, d), 7.30(1H, t), 6.82(1H, s), 5.89(1H, s), 4.94-4.89(1H, m),3.59(3H, s), 2.63(3H, s), 1.39(3H, d). Manufacturing Example 25 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 2-4-12 instead of intermediate 2-4-4.

[0355] [Chemical Formula 55] Compound 25 of this invention: 1 H-NMR (CDCl3) δ: 8.93(2H, d), 8.28(1H, s), 8.21(2H,s), 8.00(1H, s), 7.48(1H, d), 7.36(1H, t), 5.22-5.17(1H, m), 4.11-4.02(2H,m), 1.48-1.46(6H,m). Manufacturing Example 26 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10, using intermediate 2-4-8 instead of intermediate 2-4-2 and 3,5-diiodobenzoic acid instead of 3,5-dibromobenzoic acid.

[0356] [Chemical Formula 56] Compound 26 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 8.16(1H, t), 8.02(2H,d), 7.36(1H, d), 7.31(1H, t), 5.12(1H, m), 3.60(3H, s), 2.66(3H, s), 1.41(3H,d). Manufacturing Example 27 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10, using intermediate 2-4-8 instead of intermediate 2-4-2 and 3,5-bis(difluoromethoxy)benzoic acid instead of 3,5-dibromobenzoic acid.

[0357] [Chemical Formula 57] Compound 27 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 7.53(1H, d), 7.37(2H,d), 7.31(1H, t), 7.04(1H, d), 6.56(2H, t), 5.15(1H, m), 3.60(3H, s), 2.65(3H,s), 1.42(3H,d). Manufacturing Example 28 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10, using intermediate 2-4-8 instead of intermediate 2-4-2 and 3-chloro-5-trifluoromethoxybenzoic acid instead of 3,5-dibromobenzoic acid.

[0358] [Chemical Formula 58] Compound 28 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 7.67(1H, t), 7.51-7.48(2H, m), 7.35(1H, s), 7.32(1H, t), 5.18-5.14(1H, m), 3.60(3H, s), 2.66(3H,s), 1.42(3H,d). Manufacturing Example 29 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 10 using intermediate 2-4-1 instead of intermediate 2-4-2.

[0359] [Chemical Formula 59] Compound 29 of this invention: 1 H-NMR (CDCl3) δ: 8.86(2H, d), 8.23(1H, s), 7.65(1H,s), 7.36(2H, s), 7.26-7.25(1H, m), 5.84-5.82(1H, m), 3.60(3H, s), 2.74(3H,s), 1.49(3H,d). Manufacturing Example 30 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10 using intermediate 2-4-1 instead of intermediate 2-4-2 and 3,5-dichlorobenzoic acid instead of 3,5-dibromobenzoic acid.

[0360] [Chemical Formula 60] Compound 30 of this invention: LCMS: 418 [M + H] + RT=1.44 minutes Manufacturing Example 31 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10, using intermediate 2-4-1 instead of intermediate 2-4-2 and 1-methyl-3-trifluoromethyl-1H-pyrazole-5-carboxylic acid instead of 3,5-dibromobenzoic acid.

[0361] [Chemical Formula 61] Compound 31 of this invention: LCMS: 422[M+H] + RT = 1.30 minutes Manufacturing Example 32 The following shows the compounds and their physical properties manufactured in accordance with Manufacturing Example 10, using intermediate 2-4-1 instead of intermediate 2-4-2 and 3,5-dichloro-4-fluorobenzoic acid instead of 3,5-dibromobenzoic acid.

[0362] [Chemical Formula 62] Compound 32 of this invention: LCMS: 436 [M + H] + RT=1.48 minutes Manufacturing Example 33 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 5-2 instead of intermediate 2-4-4.

[0363] [Chemical Formula 63] Compound 33 of this invention: 1 H-NMR (CDCl3) δ: 8.88(2H, d), 8.25(2H, s), 8.07(1H,d), 8.00(1H, s), 7.25-7.24(1H, m), 5.28-5.27(1H, m), 4.96(1H, s), 3.47(3H,s), 3.17(3H,d), 1.41(3H,d). Manufacturing Example 34 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 6-2 instead of intermediate 2-4-4.

[0364] [Chemical Formula 64] Compound 34 of this invention: 1 H-NMR (CDCl3) δ: 8.88(2H, d), 8.24(2H, s), 8.01(2H,d), 7.26-7.24(1H, m), 5.28-5.23(1H, m), 4.87(1H, s), 3.70-3.59(2H, m), 3.46(3H, s), 1.41-1.37(6H, m). Manufacturing Example 35 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 7-4-1 instead of intermediate 2-4-4.

[0365] [Chemical Formula 65] Compound 35 of this invention: 1 H-NMR (CDCl3) δ: 8.90(2H, d), 8.21(2H, s), 8.01(1H,s), 7.74(1H, d), 7.32(1H, t), 5.30-5.25(1H, m), 3.60(3H, s), 2.70(3H, s),1.45(3H, d). Manufacturing Example 36 The following shows the compound and its physical properties manufactured in accordance with Manufacturing Example 2 using intermediate 7-4-2 instead of intermediate 2-4-4.

[0366] [Chemical Formula 66] Compound 36 of this invention: 1H-NMR (CDCl3) δ: 9.00-8.96(4H, m), 8.24(2H, s), 7.97(1H, s), 7.87(1H, d), 7.56(1H, t), 7.37(1H, t), 5.33-5.31(1H, m), 3.59(3H,s), 1.51(3H,d). Manufacturing Example 37 To a mixture of 0.059 g of intermediate 8-5 and 2.4 mL of THF, 0.13 mL of N,N-diisopropylethylamine and 0.072 g of 3,5-bis(trifluoromethyl)benzoyl chloride were added sequentially, and the mixture was stirred at room temperature for 2 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 with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.095 g of compound 37 of the present invention.

[0367] [Chemical Formula 67] Compound 37 of this invention: 1 H-NMR (CDCl3) δ: 8.24(2H, s), 7.99(1H, s), 7.93(1H,d), 7.45(1H, d), 6.66(1H, d), 5.63-5.61(1H, m), 3.97(3H, s), 3.58(3H, s),2.61(3H, s), 1.48(3H, d). Refer to manufacturing example 1-1-1 3.5 g of methyl (S)-4-[N-(tert-butyloxycarbonyl)-N-methylamino]-3-oxovalerate (hereinafter referred to as intermediate A) prepared according to the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108 was added to 27 mL of hydrogen chloride (5-10 wt% methanol solution), and stirred at room temperature for 1 hour. The resulting mixture was concentrated, the residue was dissolved in pyridine, and 3,5-bis(trifluoromethyl)benzoyl chloride was added dropwise under ice cooling, followed by stirring at room temperature for 3 hours. The resulting mixture was concentrated, 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 over sodium sulfate, filtered, and concentrated to give 3.4 g of intermediate 1-1-1 as shown below.

[0368] [Chemical Formula 68] Intermediate 1-1-1:1 H-NMR (CDCl3) δ: 7.97(1H, s), 7.92(2H, s), 5.13-5.11(1H,m), 3.77(3H, s), 3.64(2H, s), 2.93(3H, s), 1.52(3H, d). Refer to manufacturing example 1-2-1 Add 4.68 g of formamidine acetate to a mixture of 6.0 g of intermediate 1-1-1 and 50 mL of methanol, followed by 8.68 g of sodium methoxide (28% wt% methanol solution), and stir at room temperature for 18 hours. Concentrate the resulting mixture, add water, and extract with chloroform. Wash the resulting organic layer successively with water and saturated brine, dry with sodium sulfate, filter, and concentrate. Perform silica gel column chromatography on the residue to give 1.93 g of intermediate 1-2-1 as shown below.

[0369] [Chemical Formula 69] Intermediate 1-2-1: 1 H-NMR (CDCl3) δ: 8.18(1H, s), 8.09(1H, s), 7.94(2H, s), 6.55-6.44(1H, m), 5.71-4.65(1H, m), 2.90(3H, s), 1.60-1.54(3H, m). Refer to manufacturing example 1-3-1 To a mixture of 1.93 g of intermediate 1-2-1 and 24 mL of THF, 0.23 g of sodium hydride and 0.75 g of methyl iodide were added sequentially under ice-cooling conditions, and the mixture was stirred at room temperature for 7 hours. Water was added to the resulting mixture, and extraction was performed with ethyl acetate. The resulting organic layer was washed sequentially with water and saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 1.20 g of intermediate 1-3-1 as shown in the formula below.

[0370] [Chemical Formula 70] Intermediate 1-3-1: 1 H-NMR (CDCl3) δ: 8.13(1H, s), 8.11(1H, s), 7.93(2H, s), 6.44(1H, d), 5.72-4.63(1H, m), 3.53(3H, s), 2.86(3H, s), 1.57-1.54(3H, m). Refer to manufacturing example 1-4-1 To a mixture of 1.20 g of intermediate 1-3-1 and 15 mL of acetic acid, 0.80 g of N-iodosuccinimide was added, and the mixture was stirred at 50 °C for 6 hours. Another 0.80 g of N-iodosuccinimide was added, and the mixture was stirred for 7 hours. The resulting mixture was injected into an ice-cooled saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The resulting organic layer was washed with water and saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 1.07 g of intermediate 1-4-1 as shown in the formula below.

[0371] [Chemical Formula 71] Intermediate 1-4-1: 1 H-NMR (CDCl3) δ: 7.98(1H, s), 7.91(2H, s), 7.25(1H, s), 5.75(1H, s), 3.59(3H, s), 2.99(3H, s), 1.54-1.54(3H, m). Refer to manufacturing example 2-1-1 Add 3.86 g of formamidine acetate to a mixture of 6.40 g of intermediate A and 72 mL of methanol, followed by 11.9 g of sodium methoxide (28% by weight methanol solution), and stir at room temperature for 18 hours. Concentrate the resulting mixture, add water, and extract with chloroform. Add citric acid to the resulting aqueous layer until the pH reaches 5, and then 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 5.04 g of intermediate 2-1-1 as shown in the following formula.

[0372] [Chemical Formula 72] Intermediate 2-1-1: 1 H-NMR (CDCl3) δ: 8.14(1H, s), 6.35(1H, s), 5.26-4.97(1H,m), 2.80(3H, s), 1.49-1.47(12H, m). Refer to manufacturing example 2-1-2 The following shows the compound and its physical properties produced by replacing intermediate A with methyl 4-[N-(tert-butoxycarbonyl)-N-methylamino]-3-oxobutyrate according to the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108.

[0373] [Chemical Formula 73] Intermediate 2-1-2: 1 H-NMR (CDCl3) δ: 8.11(1H, s), 6.31(1H, s), 4.32(2H, d), 2.98-2.95(3H, m), 1.50-1.42(10H, m). Refer to manufacturing example 2-1-3 The following shows the compounds and their physical properties produced using acetamidine hydrochloride instead of formamidine acetate in accordance with Reference Manufacturing Example 2-1-1.

[0374] [Chemical Formula 74] Intermediate 2-1-3: 1 H-NMR (CDCl3) δ: 6.20(1H, s), 5.21-4.95(1H, m), 2.80(3H,s), 2.46(3H, s), 1.48-1.46(12H, m). Refer to manufacturing example 2-1-4 The following shows the compound and its physical properties produced by using (S)-4-[N-(tert-butoxycarbonyl)amino]-3-oxovalerate methyl ester (hereinafter referred to as intermediate B) instead of intermediate A, produced according to the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108.

[0375] [Chemical Formula 75] Intermediate 2-1-4: 1 H-NMR (CDCl3) δ: 8.12(1H, s),6.42(1H, s),5.10-5.09(1H,m),4.61(1H, s),1.44(9H, s),1.41(3H, d). Refer to manufacturing example 2-1-5 The following shows the compounds and their physical properties produced using propanedione hydrochloride instead of formamidine acetate in accordance with Reference Manufacturing Example 2-1-1.

[0376] [Chemical Formula 76] Intermediate 2-1-5: 1H-NMR (CDCl3) δ: 6.20(1H, s), 5.10-5.08(1H, m), 2.84-2.78(3H, m), 2.70-2.69(2H, m), 1.47-1.45(12H, m), 1.32(3H, t). Refer to manufacturing example 2-1-6 The following shows the compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 2-1-1 using intermediate B instead of intermediate A and acetamidine hydrochloride instead of formamidine acetate.

[0377] [Chemical Formula 77] Intermediate 2-1-6: 1 H-NMR (CDCl3) δ: 6.27(1H, s), 5.17-5.16(1H, m), 4.56(1H,s), 2.47(3H, s), 1.44(9H, s), 1.39(3H, d). Refer to manufacturing example 2-1-7 The following shows the compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 2-1-1 using intermediate B instead of intermediate A and cyclopropane formamidin hydrochloride instead of formamidin acetate.

[0378] [Chemical Formula 78] Intermediate 2-1-7: 1 H-NMR (CDCl3) δ: 6.18(1H, s), 5.07-5.05(1H, m), 4.52-4.51(1H, m), 1.91-1.87(1H, m), 1.44(9H, s), 1.33(3H, d), 1.23-1.21(2H, m), 1.13-1.09(2H, m). Refer to manufacturing example 2-1-8 The following shows the compounds and their physical properties manufactured in accordance with Reference Manufacturing Example 2-1-1 using intermediate B instead of intermediate A and propanediol hydrochloride instead of formamidine acetate.

[0379] [Chemical Formula 79] Intermediate 2-1-8: 1H-NMR (CDCl3) δ: 6.27(1H, s), 5.18-5.17(1H, m), 4.59-4.58(1H, m), 2.71(2H, q), 1.45(9H, s), 1.39(3H, d), 1.33(3H, t). Refer to manufacturing example 2-2-1 To a mixture of 1.0 g of intermediate 2-1-1 and 4 mL of DMF, add 0.62 g of methyl iodide and 1.93 g of cesium carbonate, and stir at 80 °C for 1 hour. Cool the resulting mixture to room temperature, add water, 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 to obtain 0.89 g of intermediate 2-2-1 as shown in the formula below.

[0380] [Chemical Formula 80] Intermediate 2-2-1: 1 H-NMR (CDCl3) δ: 8.07(1H, s), 6.33(1H, s), 5.24-4.97(1H,m), 3.50(3H, s), 2.77(3H, s), 1.46-1.45(12H, m). Refer to manufacturing example 2-2-2 The following shows the compound and its physical properties manufactured using intermediate 2-1-2 instead of intermediate 2-1-1 in accordance with reference manufacturing example 2-2-1.

[0381] [Chemical Formula 81] Intermediate 2-2-2: 1 H-NMR (CDCl3) δ: 8.07(1H, s), 6.29(1H, s), 4.27(2H, d), 3.50(3H, s), 2.93(3H, d), 1.45(9H, d). Refer to manufacturing example 2-3-1 3.40 g of N-iodosuccinimide was added to a mixture of 3.37 g of intermediate 2-2-1 and 25 mL of acetic acid, and the mixture was stirred at room temperature for 21 hours. Another 3.40 g of N-iodosuccinimide was added, and the mixture was stirred at room temperature for 27 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 over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 2.33 g of intermediate 2-3-1 as shown in the formula below.

[0382] [Chemical Formula 82] Intermediate 2-3-1: 1 H-NMR (CDCl3) δ: 7.93(1H, s), 5.26(1H, s), 3.57(3H, s), 2.97-2.89(3H, m), 1.42-1.41(12H, m). Refer to manufacturing example 2-3-2 The following shows the compound and its physical properties manufactured using intermediate 2-2-2 instead of intermediate 2-2-1 in accordance with Reference Manufacturing Example 2-3-1.

[0383] [Chemical Formula 83] Intermediate 2-3-2: 1 H-NMR (CDCl3) δ: 7.96(1H, s), 4.40(2H, d), 3.57(3H, d), 2.95(3H, d), 1.49-1.39(9H, m). Refer to manufacturing example 3-2-1 To a mixture of 1.0 g of intermediate 2-1-3 and 25 mL of THF, add 1.90 g of iodine and 1.08 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 sodium thiosulfate aqueous solution, water, and saturated brine. Dry the resulting organic layer with sodium sulfate, filter, and concentrate to obtain 1.38 g of intermediate 3-2-1 as shown in the formula below.

[0384] [Chemical Formula 84] Intermediate 3-2-1: 1H-NMR (CDCl3) δ: 12.27(1H, s), 5.41-5.25(1H, m), 3.01(3H,s), 2.46(3H, s), 1.43-1.41(12H, m). Refer to manufacturing example 3-2-2 The following shows the compound and its physical properties manufactured using intermediate 2-1-1 instead of intermediate 2-1-3 in accordance with reference manufacturing example 3-2-1.

[0385] [Chemical Formula 85] Intermediate 3-2-2: 1 H-NMR (CDCl3) δ: 8.05(1H, s), 5.26(1H, s), 2.95-2.85(3H,m), 1.45-1.44(3H, m), 1.41-1.39(9H, m). Refer to manufacturing example 3-3-1 To a mixture of 1.0 g of intermediate 3-2-1 and 12.7 mL of DMF, 0.40 g of methyl iodide and 1.24 g of cesium carbonate were added sequentially, and the mixture was stirred at 80 °C for 1 hour. 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 0.88 g of intermediate 3-3-1 as shown in the formula below.

[0386] [Chemical Formula 86] Intermediate 3-3-1: 1 H-NMR (CDCl3) δ: 5.25-5.22(1H, m), 3.59(3H, s), 2.95-2.93(3H, m), 2.50(3H, s), 1.42(9H, s), 1.39(3H, d). Refer to manufacturing example 3-3-2 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 3-3-1 using intermediate 3-2-2 instead of intermediate 3-2-1 and iodoethane instead of iodomethane.

[0387] [Chemical Formula 87] Intermediate 3-3-2: LCMS: 408 [M+H] + RT=1.72 minutes Refer to manufacturing example 4-3-1 To a mixture of 0.66 g of intermediate 2-1-4 and 14 mL of THF, add 1.39 g of iodine and 0.79 g of potassium carbonate, and stir under reflux for 7 hours. Cool the resulting mixture to room temperature, add 0.41 g of iodomethane, and stir at 50°C for 5 hours. Add water 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. Perform silica gel column chromatography on the residue to give 0.88 g of intermediate 4-3-1 as shown below.

[0388] [Chemical Formula 88] Intermediate 4-3-1: 1 H-NMR (CDCl3) δ: 7.96(1H, s), 5.45(1H, s), 5.09(1H, s), 3.57(3H, s), 1.48-1.45(9H, m), 1.36-1.34(3H, m). Refer to manufacturing example 4-3-2 The following shows the compound and its physical properties manufactured using intermediate 2-1-5 instead of intermediate 2-1-4 in accordance with Reference Manufacturing Example 4-3-1.

[0389] [Chemical Formula 89] Intermediate 4-3-2: 1 H-NMR (CDCl3) δ: 5.35-5.28(1H, m), 3.59(3H, s), 3.03(3H,s), 2.72(2H, q), 1.46-1.44(3H, m), 1.41-1.39(9H, m), 1.31-1.30(3H, m). Refer to manufacturing example 4-3-3 The following shows the compound and its physical properties manufactured using intermediate 2-1-6 instead of intermediate 2-1-4 in accordance with Reference Manufacturing Example 4-3-1.

[0390] [Chemical Formula 90] Intermediate 4-3-3: 1H-NMR (CDCl3) δ: 5.57(1H, s), 5.04(1H, s), 3.59(3H, s), 2.54(3H, s), 1.44-1.39(9H, m), 1.34-1.26(3H, m). Refer to manufacturing example 4-3-4 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 4-3-1 using intermediate 2-1-6 instead of intermediate 2-1-4 and iodoethane instead of iodomethane.

[0391] [Chemical Formula 91] Intermediate 4-3-4: 1 H-NMR (CDCl3) δ: 5.60(1H, s), 5.04(1H, s), 4.11(2H, t), 2.57(3H, s), 1.45(9H, s), 1.35-1.34(6H, m). Refer to manufacturing example 4-3-5 The following shows the compound and its physical properties manufactured using intermediate 2-1-7 instead of intermediate 2-1-4 in accordance with Reference Manufacturing Example 4-3-1.

[0392] [Chemical Formula 92] Intermediate 4-3-5: 1 H-NMR (CDCl3) δ: 5.33-5.32(1H, m), 5.01-4.99(1H, m), 3.76(3H, s), 1.98-1.93(1H, m), 1.44(9H, s), 1.29-1.27(3H, m), 1.23-1.22(2H, m),1.19-1.15(2H, m). Refer to manufacturing example 4-3-6 The following shows the compound and its physical properties manufactured using intermediate 2-1-8 instead of intermediate 2-1-4 in accordance with Reference Manufacturing Example 4-3-1.

[0393] [Chemical Formula 93] Intermediate 4-3-6: 1H-NMR (CDCl3) δ: 5.55-5.54(1H, m), 5.06-5.05(1H, m), 3.59(3H, s), 2.76(2H, q), 1.44(9H, s), 1.35-1.33(6H, m). Refer to manufacturing example 2-4-1 A mixture of 1.0 g of intermediate 2-3-1, 0.94 g of 2-(tributyltinyl)pyrimidine, 0.29 g of tetra(triphenylphosphine)palladium(0), 0.08 g of copper iodide(I), 0.09 g of lithium chloride, and 8.6 mL of 1,4-dioxane was stirred at 100 °C for 18 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 organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.50 g of intermediate 2-4-1 as shown below.

[0394] [Chemical Formula 94] Intermediate 2-4-1: 1 H-NMR (CDCl3) δ: 8.85(2H, d), 8.18(1H, s), 7.26-7.24(1H,m), 5.42-5.17(1H, m), 3.57-3.55(3H, m), 2.65-2.63(3H, m), 1.41-1.39(3H, m),1.27(9H, s). Refer to manufacturing example 2-4-2 The following shows the compound and its physical properties manufactured using intermediate 2-3-2 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0395] [Chemical Formula 95] Intermediate 2-4-2: 1 H-NMR (CDCl3) δ: 8.85(2H, s), 8.16(1H, s), 7.28-7.26(1H,m), 4.30(2H, d), 3.55(3H, s), 2.78(3H, d), 1.37(9H, d). Refer to manufacturing example 2-4-3 The following shows the compound and its physical properties manufactured using intermediate 3-2-1 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0396] [Chemical Formula 96] Intermediate 2-4-3: 1 H-NMR (CDCl3) δ: 12.35(1H, s), 8.86(2H, d), 7.23-7.21(1H,m), 5.47-5.13(1H, m), 2.79-2.63(3H, m), 2.43(3H, s), 1.37-1.35(3H, m), 1.28-1.26(9H, m). Refer to manufacturing example 2-4-4 The following shows the compound and its physical properties manufactured using intermediate 3-3-1 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0397] [Chemical Formula 97] Intermediate 2-4-4: 1 H-NMR (CDCl3) δ: 8.84(2H, d), 7.23(1H, t), 5.42-5.13(1H,br m), 3.56(3H, s), 2.72-2.71(3H, m), 2.58(3H, s), 1.41-1.37(3H, m), 1.28-1.25(9H, m). Refer to manufacturing example 2-4-5 The following shows the compound and its physical properties manufactured using intermediate 3-3-2 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0398] [Chemical Formula 98] Intermediate 2-4-5: 1 H-NMR (CDCl3) δ: 8.86(2H, d), 8.18(1H, s), 7.26-7.24(1H,m), 5.28(1H, d), 4.15-3.94(2H, m), 2.67(3H, s), 1.43-1.42(6H, m), 1.27-1.25(9H, m). Refer to manufacturing example 2-4-6 The following shows the compound and its physical properties manufactured using intermediate 4-3-1 instead of intermediate 2-3-1 in accordance with reference manufacturing example 2-4-1.

[0399] [Chemical Formula 99] Intermediate 2-4-6: 1 H-NMR (CDCl3) δ: 8.88(2H, d), 8.19(1H, s), 7.30(1H, t),5.47-5.45(1H, m), 4.68-4.67(1H, m), 3.56(3H, s), 1.39(9H, s), 1.35(3H, d). Refer to manufacturing example 2-4-7 The following shows the compound and its physical properties manufactured using intermediate 4-3-2 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0400] [Chemical Formula 100] Intermediate 2-4-7: 1 H-NMR (CDCl3) δ: 8.84(2H, d), 7.23(1H, t), 5.28(1H, m),3.56(3H, s), 2.87-2.66(3H, s), 2.81(2H, m), 1.45-1.22(12H, m), 1.37(3H, t). Refer to manufacturing example 2-4-8 The following shows the compound and its physical properties manufactured using intermediate 4-3-3 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0401] [Chemical Formula 101] Intermediate 2-4-8: 1 H-NMR (CDCl3) δ: 8.87(2H, d), 7.26-7.24(1H, m), 5.61-5.59(1H, m), 4.66-4.65(1H, m), 3.57(3H, s), 2.60(3H, s), 1.40(9H, s), 1.33(3H,d). Refer to manufacturing example 2-4-9 The following shows the compound and its physical properties manufactured using intermediate 4-3-4 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0402] [Chemical Formula 102] Intermediate 2-4-9: 1H-NMR (CDCl3) δ: 8.87(2H, d), 7.27-7.24(1H, m), 5.61(1H,s), 4.64(1H, s), 4.13-4.10(2H, m), 2.63(3H, s), 1.40(9H, s), 1.37(3H, t),1.33(3H, d). Refer to manufacturing example 2-4-10 The following shows the compound and its physical properties manufactured using intermediate 4-3-5 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0403] [Chemical Formula 103] Intermediate 2-4-10: 1 H-NMR (CDCl3) δ: 8.86(2H, d), 7.26-7.24(1H, m), 5.38-5.36(1H, m), 4.64(1H, s), 3.73(3H, s), 2.06-2.00(1H, m), 1.39-1.27(14H, m),1.18-1.16(2H,m). Refer to manufacturing example 2-4-11 The following shows the compound and its physical properties manufactured using intermediate 4-3-6 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0404] [Chemical Formula 104] Intermediate 2-4-11: 1 H-NMR (CDCl3) δ: 8.87(2H, d), 7.28-7.27(1H, m), 5.60-5.59(1H, m), 4.68-4.67(1H, m), 3.57(3H, s), 2.84(2H, q), 1.40-1.29(15H, m). Refer to manufacturing example 3-2-3 The following shows the compound and its physical properties manufactured using intermediate 2-1-4 instead of intermediate 2-1-3 in accordance with Reference Manufacturing Example 3-2-1.

[0405] [Chemical Formula 105] Intermediate 3-2-3: 1H-NMR (CDCl3) δ: 8.12 (1H, s), 5.51 (1H, d), 5.15-5.14 (1H, m), 1.44 (9H, s), 1.37 (3H, d). Refer to manufacturing example 3-3-3 The following shows the compounds and their physical properties produced in accordance with Reference Manufacturing Example 3-3-1 using intermediate 3-2-3 instead of intermediate 3-2-1 and iodoethane instead of iodomethane.

[0406] [Chemical Formula 106] Intermediate 3-3-3: 1 H-NMR (CDCl3) δ: 7.95 (1H, s), 5.48 (1H, s), 5.10 (1H,s), 4.04-4.00 (2H, m), 1.44 (9H, s), 1.40 (3H, t), 1.35 (3H, d). Refer to manufacturing example 2-4-12 The following shows the compound and its physical properties manufactured using intermediate 3-3-3 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0407] [Chemical Formula 107] Intermediate 2-4-12: 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.19 (1H, s), 7.30 (1H,t), 5.48 (1H, d), 4.67-4.65 (1H, m), 4.06-3.99 (2H, m), 1.43 (3H, t), 1.39(9H, s), 1.35(3H, d). Refer to manufacturing example 5-1 Add 2.24 g of 1-methylguanidine hydrochloride to a mixture of 5.0 g of intermediate B and 41 mL of methanol, followed by 8.25 g of sodium methoxide (28% by weight methanol solution). Stir at room temperature for 18 hours. Concentrate the resulting mixture, add water, and extract with chloroform. Wash the resulting organic layer successively with water and saturated brine, dry with sodium sulfate, filter, and concentrate.

[0408] The residue was dissolved in 56 mL of THF, and 5.68 g of iodine and 3.25 g of potassium carbonate were added. The mixture was stirred under reflux for 4 hours. The resulting mixture was concentrated, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with saturated sodium thiosulfate aqueous solution, water, and saturated brine, dried over sodium sulfate, filtered, and concentrated.

[0409] The residue was dissolved in 22 mL of THF, and 1.90 g of iodomethane and 2.32 g of potassium carbonate were added. The mixture was stirred at 50 °C for 2 hours. Further, 1.90 g of iodomethane was added, and the mixture was stirred at 50 °C for 6 hours. The resulting mixture was concentrated, water was added, and extraction was performed using ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.62 g of intermediate 5-1 as shown in the formula below.

[0410] [Chemical Formula 108] Intermediate 5-1: 1 H-NMR (CDCl3) δ: 5.56 (1H, d), 5.01-5.00 (1H, m), 4.76 (1H,d), 3.45 (3H, s), 3.07 (3H, d), 1.45 (9H, s), 1.34 (3H, d). Refer to manufacturing example 5-2 The following shows the compound and its physical properties manufactured using intermediate 5-1 instead of intermediate 2-3-1 in accordance with reference manufacturing example 2-4-1.

[0411] [Chemical Formula 109] Intermediate 5-2: LCMS: 361 [M+H] + RT=1.26 minutes Refer to manufacturing example 6-1 The following shows the compounds and their physical properties produced using 1-ethylguanidine sulfate instead of 1-methylguanidine hydrochloride in accordance with Reference Manufacturing Example 5-1.

[0412] [Chemical Formula 110] Intermediate 6-1: 1H-NMR (CDCl3) δ: 5.51 (1H, d), 5.01-4.98 (1H, m), 4.72-4.69(1H, m), 3.56-3.50 (2H, m), 3.45 (3H, s), 1.45 (9H, s), 1.32-1.29 (6H, m). Refer to manufacturing example 6-2 The following shows the compound and its physical properties manufactured using intermediate 6-1 instead of intermediate 2-3-1 in accordance with Reference Manufacturing Example 2-4-1.

[0413] [Chemical Formula 111] Intermediate 6-2: 1 H-NMR (CDCl3) δ: 8.83 (2H, d), 7.19 (1H, t), 5.59 (1H, d), 4.72-4.71 (2H, m), 3.61-3.60 (2H, m), 3.42 (3H, s), 1.40 (9H, s), 1.33-1.32(6H, m). Refer to manufacturing example 7-1 Add 2.84 g of S-methylisothiourea sulfate and 4.28 g of sodium carbonate to a mixture of 5.0 g of intermediate B, 40 mL of water, and 40 mL of methanol, and stir at room temperature for 4 hours. Add water to the resulting mixture and filter out the precipitated solid. Wash the solid with water and dry it under reduced pressure to obtain 4.34 g of intermediate 7-1 as shown in the following formula.

[0414] [Chemical Formula 112] Intermediate 7-1: 1 H-NMR (CDCl3) δ: 6.17 (1H, s), 5.04 (1H, d), 4.57 (1H, m), 2.58 (3H, s), 1.45 (9H, s), 1.39 (3H, d). Refer to manufacturing example 7-2 Add 5.13 g of N-iodosuccinimide to a mixture of 4.34 g of intermediate 7-1 and 15.2 mL of chloroform, and stir at 50 °C for 2 hours. Cool the resulting mixture to room temperature, add water, and extract with chloroform. Wash the resulting organic layer successively with water and saturated brine. Dry the organic layer with sodium sulfate, filter, and concentrate to obtain 3.3 g of intermediate 7-2 as shown in the formula below.

[0415] [Chemical Formula 113] Intermediate 7-2: 1 H-NMR (CDCl3) δ: 10.81 (1H, s), 5.34 (1H, d), 5.11-5.09 (1H, m), 2.62 (3H, s), 1.44 (9H, s), 1.35 (3H, d). Refer to manufacturing example 7-3 To a mixture of 0.50 g of intermediate 7-2, 0.058 g of 60% sodium hydride (oily), and 6.1 mL of THF, 0.21 g of iodomethane was added, and the mixture was stirred at 60 °C for 4 hours. The resulting mixture was cooled to room temperature, and 0.42 g of iodomethane was added, followed by stirring for 16 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 using sodium sulfate, filtered, and concentrated to obtain 0.49 g of intermediate 7-3 as shown in the formula below.

[0416] [Chemical Formula 114] Intermediate 7-3: LCMS: 426 [M+H] + RT=1.85 minutes Refer to manufacturing example 7-4 Using intermediate 7-3 instead of intermediate 2-3-1 and reacting according to reference manufacturing example 2-4-1, intermediates 7-4-1 and 7-4-2 as shown below are obtained.

[0417] [Chemical Formula 115] Intermediate 7-4-1: 1 H-NMR (CDCl3) δ: 8.86 (2H, d), 7.26-7.25 (1H, m), 5.33(1H, s), 4.75-4.73 (1H, m), 3.56 (3H, s), 2.66 (3H, s), 1.41-1.34 (12H, m). [Chemical Formula 116] Intermediate 7-4-2: 1H-NMR (CDCl3) δ: 8.98 (2H, d), 8.91 (2H, d), 7.52 (1H,t), 7.31 (1H, t), 5.55 (1H, d), 4.77-4.76 (1H, m), 3.48 (3H, s), 1.41 (3H,d), 1.37 (9H, s). Refer to manufacturing example 8-1 The following shows the compound and its physical properties produced by using methyl (S)-4-[N-(benzyloxycarbonyl)amino]-3-oxovalerate instead of intermediate B, produced according to the method described in non-patent literature Tetrahedron (2013) 69, 11092-11108, and produced according to Reference Manufacturing Example 2-1-6.

[0418] [Chemical Formula 117] Intermediate 8-1: 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 8-2 The following shows the compound and its physical properties manufactured using intermediate 8-1 instead of intermediate 2-1-3 in accordance with reference manufacturing example 3-2-1.

[0419] [Chemical Formula 118] Intermediate 8-2: 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). Refer to manufacturing example 8-3 The following shows the compound and its physical properties manufactured using intermediate 8-2 instead of intermediate 3-2-1 in accordance with reference manufacturing example 3-3-1.

[0420] [Chemical Formula 119] Intermediate 8-3: 1H-NMR (CDCl3) δ: 7.37-7.32 (5H, m), 5.89 (1H, d), 5.12-5.10(3H, m), 3.58 (3H, s), 2.51 (3H, s), 1.36 (3H, d). Refer to manufacturing example 8-4 A mixture of 0.50 g of intermediate 8-3, 0.29 g of 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)-1-H-pyrazole, 0.14 g of tetra(triphenylphosphine)palladium(0), 0.75 g of potassium phosphate, and 11.7 mL of toluene was stirred at 110 °C for 9 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 organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.18 g of intermediate 8-4 as shown below.

[0421] [Chemical Formula 120] Intermediate 8-4: 1 H-NMR (CDCl3) δ: 7.40 (1H, d), 7.34-7.31 (5H, m), 6.59 (1H,d), 5.97 (1H, d), 5.20-5.15 (1H, m), 5.09-5.03 (2H, m), 3.93 (3H, s), 3.54(3H, s), 2.54 (3H, s), 1.40 (3H, d). Refer to manufacturing example 8-5 A mixture of 0.18 g of intermediate 8-4, 0.12 g of palladium / carbon (10% by mass), and 4.7 mL of ethyl acetate was stirred at room temperature for 3 hours under a hydrogen atmosphere. The resulting mixture was filtered through diatomaceous earth and extracted with 1 mol / L hydrochloric acid and chloroform. The aqueous layer was neutralized with an aqueous solution of sodium hydroxide (10% by mass) and extracted again with chloroform. The resulting organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to give 0.059 g of intermediate 8-5 as shown in the formula below.

[0422] [Chemical Formula 121] Intermediate 8-5: 1H-NMR (CDCl3) δ: 7.41 (1H, d), 6.50 (1H, d), 4.15 (1H, q), 3.93 (3H, s), 3.54 (3H, s), 2.56 (3H, s), 1.29 (3H, d). 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.

[0423] [Chemical Formula 122] In the compound represented by formula (L-1-1) (hereinafter referred to as compound (L-1-1)), T 1 For T1-1 (#) 4 (Indicates the bonding site with the carbon atom of the carbonyl group), R 3 R 4 and R 11 For hydrogen atoms, R 2 For those recorded in [Table L1] to [Table L20] (#) 3 Compounds with any substituents (representing the bonding site with a carbon atom of a heterocyclic ring) are hereinafter referred to as compound group SX1.

[0424] [Table 2] [Table 3] [Table 4] [Table 5] [Table 6] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX2).

[0425] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 and R 11 For hydrogen atoms, R 2Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX3).

[0426] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 For methyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX4.

[0427] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX5).

[0428] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX6).

[0429] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX7).

[0430] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX8).

[0431] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 For ethyl, R 11 For hydrogen atoms, R2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX9).

[0432] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX10).

[0433] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX11).

[0434] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX12).

[0435] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX13).

[0436] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX14).

[0437] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 It is trifluoromethyl, R11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX15).

[0438] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX16).

[0439] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX17).

[0440] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX18).

[0441] In compound (L-1-1), T 1 For T1-1, R 3 and R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX19).

[0442] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX20).

[0443] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX21).

[0444] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX22).

[0445] In compound (L-1-1), T 1 For T1-1, R 3 R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX23).

[0446] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX24).

[0447] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX25).

[0448] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX26).

[0449] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 For ethyl, R11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX27).

[0450] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX28).

[0451] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX29).

[0452] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX30).

[0453] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX31).

[0454] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX32).

[0455] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX33).

[0456] In compound (L-1-1), T 1 For T1-1, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX34).

[0457] In compound (L-1-1), T 1 For T1-1, R 3 For methyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX35).

[0458] In compound (L-1-1), T 1 For T1-1, R 3 For ethyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX36).

[0459] In compound (L-1-1), T 1 For T1-2, R 3 R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX37).

[0460] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX38).

[0461] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX39).

[0462] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX40).

[0463] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX41).

[0464] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX42).

[0465] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX43).

[0466] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX44).

[0467] In compound (L-1-1), T 1 For T1-2, R 3For ethyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX45).

[0468] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX46).

[0469] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX47).

[0470] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX48).

[0471] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX49).

[0472] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX50).

[0473] In compound (L-1-1), T 1For T1-2, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX51).

[0474] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX52).

[0475] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX53).

[0476] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX54).

[0477] In compound (L-1-1), T 1 For T1-2, R 3 and R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX55).

[0478] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX56).

[0479] In compound (L-1-1), T1 For T1-2, R 3 For ethyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX57).

[0480] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX58).

[0481] In compound (L-1-1), T 1 For T1-2, R 3 R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX59).

[0482] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX60).

[0483] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX61).

[0484] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 For ethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX62.

[0485] In compound (L-1-1), T1 For T1-2, R 3 For ethyl, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX63).

[0486] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX64).

[0487] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX65).

[0488] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX66).

[0489] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX67).

[0490] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX68).

[0491] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX69).

[0492] In compound (L-1-1), T 1 For T1-2, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX70).

[0493] In compound (L-1-1), T 1 For T1-2, R 3 For methyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX71).

[0494] In compound (L-1-1), T 1 For T1-2, R 3 For ethyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX72).

[0495] In compound (L-1-1), T 1 For T1-3, R 3 R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX73).

[0496] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX74).

[0497] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX75).

[0498] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX76).

[0499] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX77).

[0500] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX78).

[0501] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX79).

[0502] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX80).

[0503] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX81).

[0504] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX82.

[0505] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX83).

[0506] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX84).

[0507] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX85).

[0508] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX86).

[0509] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX87).

[0510] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX88.

[0511] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX89).

[0512] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX90).

[0513] In compound (L-1-1), T 1 For T1-3, R 3 and R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX91).

[0514] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 For hydrogen atoms, R 11 For methyl, R2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX92).

[0515] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX93.

[0516] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX94).

[0517] In compound (L-1-1), T 1 For T1-3, R 3 R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX95).

[0518] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX96).

[0519] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX97).

[0520] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 For ethyl, R 11 For methyl, R2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX98).

[0521] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 For ethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX99).

[0522] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX100).

[0523] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX101).

[0524] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX102).

[0525] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX103).

[0526] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is trifluoromethyl, R11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX104).

[0527] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX105).

[0528] In compound (L-1-1), T 1 For T1-3, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX106).

[0529] In compound (L-1-1), T 1 For T1-3, R 3 For methyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX107).

[0530] In compound (L-1-1), T 1 For T1-3, R 3 For ethyl, R 4 It is a phenyl group, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX108).

[0531] In compound (L-1-1), T 1 For T1-4, R 3 R 4 and R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX109).

[0532] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 and R11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX110).

[0533] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX111).

[0534] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 For methyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX112).

[0535] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX113).

[0536] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX114.

[0537] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX115).

[0538] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R4 For ethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX116).

[0539] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX117).

[0540] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX118).

[0541] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX119).

[0542] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX120).

[0543] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX121.

[0544] In compound (L-1-1), T 1 For T1-4, R3 For methyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX122.

[0545] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX123).

[0546] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX124.

[0547] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX125).

[0548] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX126.

[0549] In compound (L-1-1), T 1 For T1-4, R 3 and R 4 For hydrogen atoms, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX127.

[0550] In compound (L-1-1), T1 For T1-4, R 3 For methyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX128).

[0551] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX129).

[0552] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX130).

[0553] In compound (L-1-1), T 1 For T1-4, R 3 R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX131).

[0554] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 and R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX132.

[0555] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX133).

[0556] In compound (L-1-1), T1 For T1-4, R 3 For methyl, R 4 For ethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX134.

[0557] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 For ethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX135.

[0558] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX136.

[0559] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX137.

[0560] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX138.

[0561] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX139.

[0562] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX140).

[0563] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX141.

[0564] In compound (L-1-1), T 1 For T1-4, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX142).

[0565] In compound (L-1-1), T 1 For T1-4, R 3 For methyl, R 4 It is a phenyl group, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX143).

[0566] In compound (L-1-1), T 1 For T1-4, R 3 For ethyl, R 4 It is a phenyl group, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX144.

[0567] In compound (L-1-1), T 1 For T1-5, R 3 R 4 and R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX145.

[0568] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 and R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX146).

[0569] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 and R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX147).

[0570] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 For methyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX148).

[0571] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX149).

[0572] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 For methyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX150).

[0573] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 For ethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX151).

[0574] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX152.

[0575] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 For ethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX153.

[0576] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX154.

[0577] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX155.

[0578] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 It is cyclopropyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX156).

[0579] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX157.

[0580] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX158).

[0581] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 It is trifluoromethyl, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX159.

[0582] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX160).

[0583] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX161).

[0584] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 It is a phenyl group, R 11 For hydrogen atoms, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents (hereinafter referred to as compound group SX162).

[0585] In compound (L-1-1), T 1 For T1-5, R 3 and R 4 For hydrogen atoms, R 11For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX163).

[0586] In compound (L-1-1), T 1 For T1-5, R 3 For methyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX164).

[0587] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 For hydrogen atoms, R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX165.

[0588] In compound (L-1-1), T 1 For T1-5, R 3 For hydrogen atoms, R 4 and R 11 For methyl, R 2 The compounds listed in [Table L1] to [Table L20] with any substituents are referred to as compound group SX166.

[0589] In compound (L-1-1), T 1 For T1-5, R 3 R 4 and R 11 For methyl, R 2 Compounds with any substituents listed in [Table L1] to [Table L20] (hereinafter referred to as compound group SX167).

[0590] In compound (L-1-1), T 1 For T1-5, R 3 For ethyl, R 4 and R 11 For methyl, R 2 The compou...

Claims

1. The compound shown in formula (I) or its N oxide, [Chemical Formula 1] In formula (I), Z represents an oxygen atom or a sulfur atom. 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. 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. 7a R 8a C (=NOR) 10 R 5a C (=NOR) 10 (NR) 7 R 8 ), NR 19 C(O)R 20 NR 19 C(O)OR 20 NR 19 C(O)NR 20 R 21 S(O)2NR 16 R 17 OR 18 S(O) m R 29 The group represented by formula E1, the group represented by formula E2, or the group represented by formula E3 (#) 2 (Indicates the bonding site with a carbon atom). [Chemical Formula 2] R 19 R 20 and R 21 "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 19 C(O)R 20 In the case of R 19 and R 20 Can be used with R 19 The bonded nitrogen atom and R 20 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 19 C(O)OR 20 In the case of R 19 and R 20 Can be used with R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 19 C(O)NR 20 R 21 In the case of R 19 and R 20 Can be used with R 19 The bonded nitrogen atom, the carbon atom bonded to the nitrogen atom, and R 20 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 2 CR 22 R 27 NR 23 oxygen or sulfur atoms Q 1 CR 22a Or nitrogen atoms, Q 3 CR 22b Or nitrogen atoms, Q 4 CR 22c Or nitrogen atoms, Q 5 CR 22d Or nitrogen atoms, Q 6 CR 22e or nitrogen atom (wherein, formula) The group shown in E2 does not include Q. 3 and Q 4 In the case of nitrogen atoms, Q 3 Q 5 and Q 6 The case where it is simultaneously a nitrogen atom, and Q 4 Q 5 and Q 6 (The case where both are nitrogen atoms) Q 7 CR 22f Or nitrogen atoms, R 22 and R E1 "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 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 22a R 22b R 22c R 22d R 22e and R 22f "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 23 and R E2 "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 16 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 17 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 3 This indicates a C1-C6 chain hydrocarbon group that can be substituted by one or more substituents selected from group G, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 A C3-C6 cycloalkyl group or a hydrogen atom that can be substituted by one or more substituents selected from group E. R 4 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, or OR. 18 S(O) m R 29 NR 7b R 8b C(O)NR 7b R 8b NR 9b C(O)R 5b NR 9b C(O)OR 6b NR 9 C(O)NR 7 R 8 A C3-C6 cycloalkyl, mercapto, cyano, halogen, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 18 This indicates 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, or a hydrogen atom. m represents 0, 1, or 2. R 29 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. R 3 and R 4 Can be used with R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form the group shown in formula A1, formula A2, formula A3, formula A4, formula A5, formula A6, or formula A7 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R 1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 3] B 1 B 2 B 3 and B 4 Combinatorial representation: B 1 For CR 2a B 2 For CR 2b B 3 Nitrogen atom or CR 2c B 4 Nitrogen atom or CR 2d The combination; B 1 For CR 2a B 2 For nitrogen atoms, B 3 For CR 2c B 4 Nitrogen atom or CR 2d The combination; B 1 For CR 2a B 2 For nitrogen atoms, B 3 For nitrogen atoms, B 4 For CR 2d The combination; B 1 For nitrogen atoms, B 2 For CR 2b B 3 For nitrogen atoms, B 4 For CR 2d The combination; B 1 For nitrogen atoms, B 2 For CR 2b B 3 For CR 2c B 4 Nitrogen atom or CR 2d Combinations; or B 1 For nitrogen atoms, B 2 For nitrogen atoms, B 3 For CR 2c B 4 For CR 2d The combination B 5 and B 8 The same or different from each other indicates CR 25 Or nitrogen atoms, B 6 and B 7 The same or different from each other indicates oxygen atom, sulfur atom, or NR. 26 , R 25 This 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, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 C (=NOR) 10 R 5 C (=NOR) 10 (NR) 7 R 8 ), NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 N=S(O) p R 24 R 28 S(O) m R 29 cyano, halogen, or hydrogen atoms R 26 This indicates 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 halogen atoms, or a hydrogen atom. R A and R B "Identical" or "different from each other" refers to C1-C6 alkyl groups that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups that can be substituted with one or more halogen atoms, or hydrogen atoms. R 2a R 2b R 2c R 2d R 2e R 2f R 2g R 2h R 2i R 2j R 2k R 2l R 2m R 2n R 2o R 2p R 2q R 2r R 2s R 2t R 2u and R 2v "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, 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, or a C(O)R group. 5 C(O)OR 6 C(O)NR 7 R 8 C (=NOR) 10 R 5 C (=NOR) 10 (NR) 7 R 8 ), NR 7 R 8 NR 9 C(O)R 5 NR 9 C(O)OR 6 NR 9 C(O)NR 7 R 8 N=S(O) p R 24 R 28 S(O) m R 29 cyano, halogen, or hydrogen atoms X represents NR 11 C(Z)R 12 、NR 11 C(O)OR 12 、NR 11 C(Z)NR 12 R 13 、NR 11 C(=NOR 10 )R 12 、NR 11 C(=NOR 10 )(NR 11 R 12 ), N=C(OR 10 )R 12 、N=C(SR 10 )R 12 、N=C(NR 7 R 8 )R 12 、NR 11 X 1 、 or N=S(O) p R 12 R 28 , p represents 0 or 1. X 1 This indicates a 9- or 10-membered aromatic heterocyclic group {this 9- or 10-membered aromatic heterocyclic group can be selected from group A} 2 If one or more substituents are used in the heterocycle, the ring member atoms of the heterocycle, in addition to the carbon atom, include one, two, or three heteroatoms selected from the group consisting of N, O, and S. R 5 R 5a and R 5b "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 a hydrogen atom. R 6 and R 6b "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 C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 7 R 7a and R 7b "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, or a C3-C6 cycloalkyl, cyano, or hydrogen atom that can be substituted by one or more substituents selected from group E. R 8 R 8a and R 8b "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 a hydrogen atom. R 9 and R 9b "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 D, a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E, or a hydrogen atom. R 10 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 11 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 15 C(O)R 14 C(O)OR 14 C (=NR) 8 R 14 C(O)NR 7 R 8 or hydrogen atoms, R 12 This indicates that it can be selected from group A. 3 The phenyl group having one or more substituents, or being selected from group A 3 A 5- or 6-membered aromatic heterocyclic group substituted with one or more substituents, R 24 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, or a C3-C6 cycloalkyl group that can be substituted by one or more substituents selected from group E. 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. R 13 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 14 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: halogen atom, C1-C6 alkoxy group that can be substituted with one or more halogen atoms, C1-C6 alkyl group that can be substituted with one or more halogen atoms, and cyano group}, 5- or 6-membered aromatic heterocyclic group that can be substituted with one or more halogen atoms, C3-C6 cycloalkyl group that can be substituted with one or more halogen atoms, or hydrogen atom. R 15 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 {where the phenyl portion of the phenylmethyl group 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. 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 3b1 C(O)R 3c1 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 3f1 R 3g1 S(O)2NR 3f R 3g NR 3b C (=NOR) 3j R 3d NR 3b S(O) m R 3k S(O) m R 3k A group composed of cyano, nitro and halogen atoms. Group A 2 : 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}, phenyl that may be substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group B, OR 3aa 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) m R 3k S(O) m R 3k A group composed of cyano, nitro and halogen atoms. Group A 3 : 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}, phenyl that may be substituted by one or more substituents selected from group B, 5- or 6-membered aromatic heterocyclic group that may be substituted by one or more substituents selected from group B, OR 3ab 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) m R 3k S(O) m R 3ka A group composed of cyano, nitro and halogen atoms. R 3a R 3aa and R 3ab "Same or different" refers to 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 3c C(O)OR 3j C(O)NR 3f R 3g S(O)2R 3k or hydrogen atoms, R 3b and R 3b1 The same or different from each other indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3c and R 3c1 "Same" or "different" refers to 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 phenyl C1-C3 alkyl group {where the phenyl portion of the phenyl C1-C3 alkyl group can be substituted with one or more substituents selected from group B}. R 3f and R 3f1 The same or different from each other indicates a C1-C6 chain hydrocarbon group or hydrogen atom that can be replaced by one or more halogen atoms. R 3g and R 3g1 "Same" or "different" refers to 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 and R 3ka "Same or different" refers to 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 D: 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 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 cyano groups, oxo 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 membered non-aromatic heterocyclic groups, cyano groups, and halogen atoms. Group G: 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 It is a group composed of 3-6 non-aromatic heterocyclic groups, cyano groups, nitro groups, and halogen atoms.

2. The compound or its N oxide as claimed in claim 1, wherein, R 3a R 3aa and R 3ab "Same or different" refers to 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 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), Z stands for oxygen atom. L is a single bond or -(CR) 4a R 4b ) n -, R 4a and R 4b They may be the same or different from each other, and are C1-C3 alkyl or hydrogen atoms. n is 1, 2, or 3. R 1 It is a C1-C3 chain hydrocarbon group or a hydrogen atom that can be replaced by one or more halogen atoms. 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} 3b1 C(O)R 3c1 C(O)NR 3f1 R 3g1 , cyano group and halogen atom}, C(O)NR 7a R 8a C (=NOR) 10 R 5a The group shown in formula E1-1 or the group shown in formula E3-1 (# 2 (Indicates the bonding site with a carbon atom). [Chemical Formula 4] R 3b1 It is a C1-C3 alkyl group or a hydrogen atom. R 3c1 It is a C1-C3 alkyl or cyclopropyl group. R 3f1 It is a C1-C3 alkyl group or a hydrogen atom. R 3g1 It consists of a C1-C3 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom. R 5a It is a C1-C3 alkyl group. R 7a It is a C1-C3 alkyl group or a hydrogen atom. R 8a The following are possible meanings: a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted by one or more substituents selected from the group consisting of cyclopropyl and halogen atoms}; a phenyl group {the phenyl group may be substituted by one or more substituents selected from the group consisting of cyano, trifluoromethyl and halogen atoms}; a 5- or 6-membered aromatic heterocyclic group {the 5- or 6-membered aromatic heterocyclic group may be substituted by one or more substituents selected from the group consisting of cyano, trifluoromethyl and halogen atoms}; or a cyclopropyl group or a hydrogen atom. R 10 It is a C1-C3 alkyl group or a hydrogen atom. R 22a R 22f and R E1 They may be identical or different from each other, and are C1-C3 alkyl groups or hydrogen atoms that can be substituted by one or more halogen atoms. R 23 and R E2 The same or different from each other, being C1-C3 alkyl, cyclopropyl, or hydrogen atoms that can be substituted by one or more halogen atoms. R 3 It can be a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkylmethyl group, a phenylmethyl group, a pyridylmethyl group, a cyanomethyl group, a tetrahydrofuranylmethyl group, a cyclopropyl group, or a hydrogen atom. R 4 C1-C3 alkyl, phenyl, or pyridyl groups that can be substituted with one or more halogen atoms {the phenyl and pyridyl groups can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkyl, cyano, and halogen atoms that can be substituted with one or more halogen atoms}, OR 18 S(O) m R 29 NR 7b R 8b C(O)NR 7b R 8b NR 9b C(O)R 5b NR 9b C(O)OR 6b , mercapto group, cyclopropyl group, halogen atom or hydrogen atom, R 18 It is a C1-C3 alkyl group or a hydrogen atom that can be substituted by one or more halogen atoms. R 29 It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 5b It is a C1-C3 alkyl 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-C3 alkyl groups that can be substituted with one or more halogen atoms, C1-C3 alkoxy groups that can be substituted with one or more halogen atoms, cyano groups and halogen atoms}, pyridyl groups, or C3-C6 cycloalkyl groups. R 6b It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 7b It is a C1-C3 chain hydrocarbon group, cyano group, or hydrogen atom that can be replaced by one or more halogen atoms. R 8b The following are C1-C3 chain hydrocarbon groups that can be substituted with one or more halogen atoms, phenyl groups {the phenyl group can be substituted with one or more substituents selected from the group consisting of cyano, trifluoromethyl, and halogen atoms}, 5- or 6-membered aromatic heterocyclic groups {the 5- or 6-membered aromatic heterocyclic groups can be substituted with one or more substituents selected from the group consisting of cyano, trifluoromethyl, and halogen atoms}, cyclopropyl groups, or hydrogen atoms. R 9b It consists of a C1-C3 chain hydrocarbon group, a cyclopropyl group, or a hydrogen atom. R 3 and R 4 With R 3 The bonded nitrogen atom and R 4 The bonded carbon atoms together form a group represented by formula A1-1-1, a group represented by formula A5-2-1, or a group represented by formula A6-2 (# indicates a group with R). 2 The bonding site, ● indicates the bonding with R 1 (The bonding sites of the bonded carbon atoms). [Chemical Formula 5] X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 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 groups substituted by one or more substituents selected from the group consisting of cyano and halogen atoms, cyclopropyl groups substituted by one or more cyano groups, OR} 3aa The ring members of the heterocycle, in addition to the carbon atom, include one, two, or three heteroatoms selected from the group consisting of N, O, and S. R 3aa It is a C1-C3 alkyl group that can be substituted by one or more halogen atoms. R 11 It is a C1-C3 alkyl, C1-C2 alkylsulfonyl, OCH3, C(O)R that can be substituted by one or more substituents selected from group F. 14 C(O)OR 14 or hydrogen atoms, R 12 The group is phenyl, pyrazolyl, or pyridyl {the phenyl, pyrazolyl, or pyridyl 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 cyano and halogen atoms}, cyclopropyl group substituted with one or more cyano groups, OR 3ab S(O) m R 3ka , cyano group and halogen atom, R 13 It is a C1-C3 alkyl group or a hydrogen atom. R 14 It is a C1-C4 alkyl or cyclopropyl group. R 3ab It can be a C1-C3 alkyl group that can be substituted with one or more halogen atoms, a cyclopropyl group that can be substituted with one or more cyano groups, or a hydrogen atom. R 3ka It is a C1-C3 alkyl group or a cyclopropyl group that can be substituted with one or more halogen atoms. Group F is composed of cyclopropyl, phenyl, pyridyl, tetrahydrofuranyl, tetrahydropyranyl and cyano.

4. The compound or its N oxide as described in claim 1 or 2, wherein, In formula (I), Z stands for oxygen atom. L represents a single bond. R 1 It is a methyl or 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}, R 3 It consists of C1-C3 chain hydrocarbon groups or hydrogen atoms. R 4 A C1-C3 alkyl, phenyl, pyridyl, or pyrimidinyl group that can be substituted with one or more halogen atoms {the phenyl, pyridyl, and pyrimidinyl group can be substituted with one or more substituents selected from the group consisting of: C1-C3 alkyl, cyano, and halogen atoms that can be substituted with one or more halogen atoms}, SR 29 NR 7b R 8b Cyclopropyl, cyano, or hydrogen atom R 29 It is a C1-C3 alkyl group. R 7b It is a hydrogen atom. R 8b It is a C1-C3 chain hydrocarbon group. X is NR 11 C(O)R 12 NR 11 C(O)NR 12 R 13 , or NR 11 X 1 , X 1 The quinazolinyl group can be substituted by one or more substituents selected from the group consisting of: trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, cyclopropyl which can be substituted by cyano, and halogen atoms. R 11 It is a methyl or hydrogen atom. R 12 The group is phenyl or pyrazolyl {the phenyl group and the pyrazolyl group may be substituted by one or more substituents selected from the group consisting of: methyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, methanesulfonyl, trifluoromethanesulfonyl, cyano, cyclopropyl which may be substituted by cyano, and halogen atoms}. R 13 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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