Heterocyclic compound and harmful arthropod-controlling composition containing same

Abstract

Provided is a compound which has an excellent controlling effect on harmful arthropods. This compound represented by formula (I) (in the formula, R1 represents a C1-C3 chain hydrocarbon group or the like which may be substituted with one or more halogen atoms; R2 represents a 5- or 6-membered aromatic heterocyclic group or the like which may be substituted with one or more substituents selected from group A; R3 represents a C1-C6 chain hydrocarbon group or the like which may be substituted with one or more substituents selected from group B; Q represents a group represented by formula B1 or the like; Z1 represents an oxygen atom or the like; X represents a group represented by formula C1-1 or the like; group A is a group consisting of C1-C6 chain hydrocarbon groups and the like; and group B is a group consisting of cyclopropyl groups and the like) or an N oxide thereof has an excellent controlling effect on harmful arthropods.

Description

Heterocyclic compound and pest control composition containing the same

[0001] This patent application claims priority under the Paris Convention to and the benefit of Japanese Patent Application No. 2024-130877 (filed August 7, 2024), the entire contents of which are incorporated herein by reference. The present invention relates to heterocyclic compounds and pest arthropod control compositions containing the same.

[0002] Various compounds have been investigated so far for the purpose of controlling harmful arthropods. For example, Patent Document 1 describes that certain compounds have a pest control effect.

[0003] International Publication No. 2022 / 157188

[0004] An object of the present invention is to provide a compound having excellent control activity against arthropod pests.

[0005] The present inventors have conducted research to find an excellent method for controlling harmful arthropods, and as a result have found that a compound represented by the following formula (I) has excellent control activity against harmful arthropods. The present invention is as follows: [1] Formula (I) [In the formula, R １ represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; R ２ represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group A, a phenyl group optionally substituted with one or more substituents selected from group A, a 9-membered aromatic heterocyclic group {the 9-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4 (# 1 represents a bonding site with Q), R a11 , R a12 , R a33 , and R a34are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, a C(O)OR aa1 , C(O)NR aa2 R aa3 , a cyano group, a halogen atom, or a hydrogen atom; R a21 , R a23 , R a42 , and R a44 are the same or different and represent a halogen atom or a hydrogen atom; R aa1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a hydrogen atom; R aa2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R aa3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R a31 , R a32 , R a53 , or R a54 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a phenyl group optionally substituted with one or more substituents selected from Group C, a cyclopropyl group, and a halogen atom, or a hydrogen atom, R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, a cyclopropyl group, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkylsulfonyl group, OR 3a , C(O)R 3b , C(O)OR 3c or a hydrogen atom, R 3a represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R 3brepresents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), a phenyl group which may be substituted with one or more substituents selected from Group C, a cyclopropyl group, or a hydrogen atom; R 3c represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, and a halogen atom}, a phenyl group optionally substituted with one or more substituents selected from Group C, or a cyclopropyl group; Q represents a group represented by Formula B1, a group represented by Formula B2, or a group represented by Formula B3 (# 2 is R 1 represents the bonding site with the carbon atom to which it is bonded, and # 3 is R 2 represents a binding site with R b11 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, NR ba1 C(O)R ba2 , N.R. ba3 C(O)OR ba4 , N.R. ba5 R ba6 , C(O)NR ba7 R ba8 , C(O)OR ba9 , S(O) ｑ R ba10 , a cyano group, or a hydrogen atom; R ba1 represents a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, C(O)R ba11 or a hydrogen atom, R ba2 , R ba4 , R ba9 , R ba10 , and R ba11 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms; R ba3 , Rba5 , R ba6 , R ba7 and R ba8 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; q represents 0, 1, or 2; R b21 , and R b22 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, or a hydrogen atom; R b31 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, NR bb1 C(O)R bb2 , N.R. bb3 C(O)OR bb4 , N.R. bb5 C(O)NR bb6 R bb7 , N.R. bb8 S(O)2R bb9 , N.R. bb10 R bb11 , a nitro group, a cyano group, a halogen atom, or a hydrogen atom; R bb1 , R bb3 , R bb5 , R bb6 , R bb8 , and R bb10 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, a cyclopropyl group, or a hydrogen atom; R bb4 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a cyclopropyl group; R bb7 and R bb11 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; Rbb9 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a cyclopropyl group; R ｂ32 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, C(O)NR bb12 R bb13 , C(O)OR bb14 , S(O) ２ R bb15 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R bb12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; R bb14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb15 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a cyclopropyl group; Z 1 is an oxygen atom, a sulfur atom, NR ZZ1 , N-OR ZZ2 , N-CN, N-NO ２ , C(CN) ２ , NS(O) ２ R ZZ3 , or NC(O)OR ZZ4 represents R ZZ1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R ZZ2 represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R ZZ3represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from group C. ZZ4 represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom}, a phenyl group which may be substituted with one or more substituents selected from Group C, or a cyclopropyl group; X represents a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1 (# 4 is Z 1 represents the bonding site with the carbon atom bonded to Z 2 represents an oxygen atom or a sulfur atom; Z 3 is a nitrogen atom or CR C14 represents Z 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is a nitrogen atom, and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is CR C21 and Z 5 is a nitrogen atom, and Z 6 is CR C23 and Z 7 is CR C24 or a combination in which Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z7 represents a combination in which R is a nitrogen atom; c21 , R c31 , R c14 , R c24 , and R c34 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom; R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), NR cc1 C(O)R cc2 , C(O)NR cc3 R cc4 , C(O)OR cc5 , OR cc6 , S(O) ２ R cc7 , a nitro group, a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are each a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, a cyclopropyl group, a cyano group, and a halogen atom}, a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, C(O)NR cc8 R cc9 , C(O)R cc10 , or S(O) ２ R cc11 represents R cc1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 1C or a hydrogen atom, R 1Crepresents a cyclopropyl group, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R cc2 and R cc4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc5 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from group C, or a hydrogen atom; R cc6 represents a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom), C(O)R 61C , C(O)OR 62C , C(O)NR 63C R 64C , S(O)R 65C or a hydrogen atom, R 61C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 62C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 63C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 64C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 65Crepresents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R cc7 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R cc8 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc9 represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom; R cc10 and R cc11 are the same or different and represent a C1-C6 open chain hydrocarbon group {the C1-C6 open chain hydrocarbon group is optionally substituted with one or more substituents selected from the group consisting of a phenyl group optionally substituted with one or more substituents selected from Group C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group C, a cyclopropyl group, and a halogen atom}, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; Group A: a C1-C6 open chain hydrocarbon group {the C1-C6 open chain hydrocarbon group is optionally substituted with one or more substituents selected from the group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom}, a cyclopropyl group {the cyclopropyl group is optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, OR 1A , SF5, NR 2A C(O)R 3A , N.R. 4A C(O)OR 5A , N.R. 6A C(O)NR 7A R8A , N=S(O) p R 9A R 10A , C(O)R 11A , C(O)OR 12A , C(O)NR 13A R 14A , S(O)NR 15A R 16A , N.R. 17A S(O)2R 18A , S(O) m R 19A , a cyano group, and a halogen atom. 1A represents a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C(O)R 20A , C(O)OR 21A , C(O)NR 22A R 23A , S(O)R 24A or a hydrogen atom, R 2A , R 4A , R 6A , R 7A , R 13A , R 15A , R 17A , and R 22A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 3A , R 8A , R 11A , R 14A , and R 16A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 5A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, and NR 2A C(O)R 3A If R 2Aand R 3A is R 2A and a nitrogen atom to which R 3A may be taken together with the carbon atom to which NR is bonded to form a 5- or 6-membered non-aromatic heterocycle which may be substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), 4A C(O)OR 5A If R 4A and R 5A is R 4A and a nitrogen atom to which R 5A may be taken together with the oxygen atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle which may be substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), 6A C(O)NR 7A R 8A If R 6A and R 7A is R 6A and a nitrogen atom to which R 7A may be taken together with the nitrogen atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle which may be substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), 6A C(O)NR 7A R 8A If R 7A and R 8A is R 7A and R 8A may be bonded together with the nitrogen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), C(O)NR 13A R 14A If R 13A and R 14A is R 13A and R 14Amay be bonded together with the nitrogen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), p represents 0 or 1, R 9A and R 10A are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 12A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R 18A and R 19A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, m represents 0, 1, or 2, R 20A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R 21A , R 23A , and R 24A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a phenyl group optionally substituted with one or more substituents selected from Group C. Group B: a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, OR 3B , a cyano group, and a halogen atom. 3Brepresents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. Group C: a group consisting of a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a C3-C6 cycloalkyl group {the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom. ] (hereinafter referred to as Compound N of the present invention), or an N-oxide thereof, or a salt thereof (hereinafter the compound represented by formula (I) or the N-oxide thereof, or a salt thereof will be referred to as Compound of the present invention). [2] A compound represented by formula (I), b11 [3] The compound according to [1], or an N-oxide thereof, or a salt thereof, wherein R in formula (I) is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, or a hydrogen atom. ２is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazolyl group, the thiazolyl group, the isothiazolyl group, the oxazolyl group, the isoxazolyl group, the 1,2,4-oxadiazolyl group, the 1,3,4- [4] The compound according to [1], or an N-oxide thereof, or a salt thereof, wherein R in formula (I) is an oxadiazolyl group, the 1,2,4-thiadiazolyl group, the 1,3,4-thiadiazolyl group, the 1,2,3-triazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group are optionally substituted with one or more substituents selected from Group A}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group are optionally substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4. ２is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazolyl group, the thiazolyl group, the isothiazolyl group, the oxazolyl group, the isoxazolyl group, the 1,2,4-oxadiazolyl group, the 1,3,4- [5] The compound according to [2], or an N-oxide thereof, or a salt thereof, wherein R in formula (I) is an oxadiazolyl group, the 1,2,4-thiadiazolyl group, the 1,3,4-thiadiazolyl group, the 1,2,3-triazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group are optionally substituted with one or more substituents selected from Group A}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group are optionally substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4. １ is a methyl group, Q is a group represented by formula B1 or a group represented by formula B2, R b11 is a C1-C3 chain hydrocarbon group, a methoxy group, a cyclopropyl group, a halogen atom, NR ba1 C(O)R ba2 , N.R. ba3 C(O)OR ba4 , N.R. ba5 R ba6 , C(O)NR ba7 R ba8 , S.R. ba10 or a hydrogen atom, R ba1 But C(O)R ba11 and R ba2 , R ba8 , R ba10 , and R ba11is a methyl group, and R ba3 , R ba5 , and R ba7 is a hydrogen atom, and R ba6 is a methyl group or a hydrogen atom, R ba4 is a C1-C4 chain hydrocarbon group, R b21 , and R b22 is a hydrogen atom, and R ３ is a methyl group, an ethyl group, or a hydrogen atom; Z 1 is an oxygen atom, and X is a group represented by formula C1-1 or a group represented by formula C2-1 (# 4 is Z 1 represents a bonding site with the carbon atom bonded to Z; 2 is a sulfur atom or an oxygen atom, Z 3 is a nitrogen atom or CH, 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 R c21 is a hydrogen atom, and R c22 , and R c24 are the same or different and are a halogen atom or a hydrogen atom, R c23 is a C1-C4 chain hydrocarbon group (which may be substituted with one or more halogen atoms), a cyano group, a halogen atom, or a hydrogen atom; R c13 is a C1-C4 chain hydrocarbon group (the C1-C4 chain hydrocarbon group may be substituted with one or more halogen atoms), a cyclopropyl group, or a hydrogen atom, and R c15 , and R c25are the same or different and are a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, a phenyl group, and a halogen atom), and Q is a group represented by formula B1, then R ２ a pyrimidinyl group {the pyrimidinyl group is a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, an NR 2A C(O)R 3A , N.R. 4A C(O)OR 5A , C(O)NR 13A R 14A , a cyano group, and a halogen atom}, a pyridyl group {the pyridyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a pyridazinyl group {the pyridazinyl group is selected from the group consisting of a methyl group, a methoxy group, and a C(O)NR 33A R 34A and optionally substituted with one or more substituents selected from the group consisting of a pyrazinyl group, a thiazolyl group {the thiazolyl group is C(O)OR 12A , C(O)NR 43A R 44A and a cyano group}, a phenyl group {the phenyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, a11 and R a33 is a hydrogen atom, and R a21 and R a23 is a hydrogen atom, and R a31 and R a53 are the same or different and are a methyl group or an ethyl group, R 2A is a methyl group or a hydrogen atom, R 3A is a methyl group or a cyclopropyl group, R 4A , R 13A , R 33A and R 43Ais a hydrogen atom, and R 5A , R 12A , R 34A and R 44A is a methyl group, and R 14A is a methyl group or a hydrogen atom, and Q is a group represented by formula B2, then R ２ [6] The compound according to [1], or an N-oxide thereof, or a salt thereof, wherein R in formula (I) is a pyrimidinyl group or a 1,2,3-triazolyl group. １ is a methyl group, and R ２ a pyrimidinyl group, a pyridyl group (the pyrimidinyl group and the pyridyl group are C(O)NR 13A R 14A , a cyano group, and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, a11 and R a33 is a hydrogen atom, and R a21 and R a23 is a hydrogen atom, and R a31 and R a53 are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from the group consisting of cyclopropyl groups and halogen atoms, R ３ is a methyl group or a hydrogen atom, Q is a group represented by formula B1 or a group represented by formula B2, R b11 , R b21 , and R b22 is a hydrogen atom, and Z 1 is an oxygen atom, and X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1 (# 4 is Z 1 represents a bonding site with the carbon atom bonded to Z; 2 is a sulfur atom or an oxygen atom, Z 3 is a nitrogen atom or CH, 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CRC21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 R c21 , R c31 , R c24 , and R c34 is a hydrogen atom, and R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), OR cc6 , a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 and are the same or different and are a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom), or a cyclopropyl group (the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom) or an N-oxide thereof according to [2], or a salt thereof. [In the formula, X A1 and X A2 are the same or different and represent a fluorine atom, a chlorine atom, or a hydrogen atom; Z A3 represents a nitrogen atom or CH.] or a salt thereof. [8] A compound represented by formula (III): [In the formula, X C1 represents a halogen atom, a trifluoromethyl group, or a difluoromethyl group; X C2 represents a fluorine atom, a chlorine atom, or a hydrogen atom.] or a salt thereof. [9] A compound represented by formula (IV): [In the formula, X D1represents a C1-C4 chain hydrocarbon group or a cyclopropyl group; X D2 represents a fluorine atom, a chlorine atom, or a hydrogen atom; Z D3 represents a nitrogen atom or CH.] or a salt thereof.

[10] A composition for controlling arthropod pests, comprising the compound according to any one of [1] to [6], its N-oxide, or a salt thereof, and an inert carrier.

[11] A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to any one of [1] to [6], its N-oxide, or a salt thereof: Group (a): a group consisting of an insecticidal active component, an acaricidal active component, and a nematicidal active component; Group (b): a fungicidal active component; Group (c): a plant growth regulator component; Group (d): a repellent component.

[12] A method for controlling arthropod pests, comprising applying an effective amount of the compound according to any one of [1] to [6], its N-oxide, or a salt thereof, or an effective amount of the composition according to

[11] to arthropod pests or to a habitat of arthropod pests.

[13] A seed or a vegetative reproductive organ carrying an effective amount of the compound according to any one of [1] to [6], its N-oxide, or a salt thereof, or an effective amount of the composition according to

[11] .

[0006] According to the present invention, arthropod pests can be controlled.

[0007] The substituents in the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent has two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In this specification, the notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. 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. 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. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. Examples of alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, propylsulfonyl, and isopropylsulfonyl groups. Examples of cycloalkylsulfonyl groups include cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, and cyclohexylsulfonyl groups.Examples of the 9-membered aromatic heterocyclic group include a benzoxazolyl group, a benzisoxazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a triazolopyridyl group, a triazolopyrimidinyl group, and an imidazolopyrimidinyl group. Examples of the 5- or 6-membered aromatic heterocyclic group include a 5-membered aromatic heterocyclic group selected from a pyrazolyl group, an imidazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, and a tetrazolyl group; and a 6-membered aromatic heterocyclic group selected from a pyridyl group, a pyrimidinyl group, a pyridazinyl group, and a pyrazinyl group. The (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms refers to a group in which the (C3-C6 cycloalkyl) and / or (C1-C3 alkyl) optionally has one or more halogen atoms, and examples thereof include a cyclopropylmethyl group, a cyclopropylethyl group, a (2,2-difluorocyclopropyl)methyl group, a 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, and a 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group. Examples of the C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms include a methyl group, an ethyl group, a propyl group, a 2-methyl-propyl (i.e., a 1,1-dimethylethyl) group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 1,1,1-trifluoroethyl group, an ethylene group, a 1-propylene group, a 1-propyne group, and a 1-butyne group, and examples of the C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms include a methyl group, an ethyl group, a propyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 1,1,1-trifluoroethyl group, an ethylene group, a 1-propylene group, and a 1-propyne group.Examples of C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from the group consisting of cyclopropyl groups and halogen atoms include methyl groups, ethyl groups, n-propyl groups, 1,1-difluoroethyl groups, 1-cyclopropylethyl groups, and 1-propyne groups. Examples of C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, 1-fluorocyclopropyl groups, 1,1-difluorocyclopropyl groups, and 1,2-difluorocyclopropyl groups. Examples of C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms include methylsulfonyl groups, ethylsulfonyl groups, n-propylsulfonyl groups, isopropylsulfonyl groups, n-butylsulfonyl groups, tert-butylsulfonyl groups, n-pentylsulfonyl groups, n-hexylsulfonyl groups, 1-trifluoromethylsulfonyl groups, and 1-trifluoromethylmethylsulfonyl groups. Examples of the C1-C3 alkoxy group optionally substituted with one or more halogen atoms include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, a 1-chloromethoxy group, a 1-bromomethoxy group, and a 1-iodomethoxy group.

[0008] NR 2A C(O)R 3A If R 2A and R 3A is R 2A and a nitrogen atom to which R 3A may be bonded to together with the carbon atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), for example, a ring structure as shown below: (# 1 represents the bonding site with Q). 4A C(O)OR 5A If R 4A and R 5A is R 4A and a nitrogen atom to which R 5Amay be bonded to together with the oxygen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), for example, a ring structure as shown below: (# 1 represents the bonding site with Q). 6A C(O)NR 7A R 8A If R 6A and R 7A is R 6A and a nitrogen atom to which R 7A may be bonded together with the nitrogen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), for example, a ring structure as shown below: (# 1 represents the bonding site with Q). 6A C(O)NR 7A R 8A If R 7A and R 8A is R 7A and R 8A may be bonded together with the nitrogen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), for example, a ring structure as shown below: (# 1 represents the bonding site with Q). 13A R 14A If R 13A and R 14A is R 13A and R 14A may be bonded together with the nitrogen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), for example, a ring structure as shown below: (# 1 represents a bonding site with Q).

[0009] The compound of the present invention may exist in one or more stereoisomers. Examples of stereoisomers include enantiomers, diastereomers, and geometric isomers. The compound of the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.

[0010] The N-oxide of the compound represented by formula (I) means a structure in which at least one nitrogen atom contained in the compound represented by formula (I) is substituted with an oxo group.

[0011] Compound N of the present invention may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrogen halides (e.g., hydrogen chloride, hydrogen bromide, hydrogen iodide), phosphoric acid, and sulfuric acid; and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, and methanesulfonic acid. The acid addition salt can be obtained, for example, by mixing Compound N of the present invention with an acid.

[0012] The following compounds are examples of the compound N of the present invention.

[0013] [Embodiment 1] In the compound N of the present invention, X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1 (# 4 is Z 1 represents the bonding site with the carbon atom bonded to Z 2 is an oxygen atom or a sulfur atom, and Z 3 is a nitrogen atom, or CR c14 and Z 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is a nitrogen atom, and Z 5 is CR C22 and Z 6 is CRC23 and Z 7 is CR C24 A combination in which: Z 4 is CR C21 and Z 5 is a nitrogen atom, and Z 6 is CR C23 and Z 7 is CR C24 or a combination in which Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is a nitrogen atom, and R c21 , R c31 , R c14 , R c24 , and R c34 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom, and R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different, and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), OR cc6 , S(O) ２ R cc7 , a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom} or a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, and R cc6 is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom), S(O)R65C or a hydrogen atom, and R 65C is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and R cc7 is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Embodiment 2] In compound N of the present invention, X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1, and Z 2 is an oxygen atom or a sulfur atom, and Z 3 is a nitrogen atom, or CR c14 and Z 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is a nitrogen atom, and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is CR C21 and Z 5 is a nitrogen atom, and Z 6 is CR C23 and Z 7 is CR C24 or a combination in which Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 represents a combination in which R is a nitrogen atom; c21 , R c31 , R c24 , and R c34 is a hydrogen atom, and R c14 is a methyl group or a hydrogen atom, and R c22 , R c32 , R c13, R c23 , and R c35 are the same or different, and each represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), a cyclopropyl group, OR cc6 , a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are C1-C6 chain hydrocarbon groups (the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom), R cc6 is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom), S(O)R 65C or a hydrogen atom, and R 65C is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. [Embodiment 3] In compound N of the present invention, X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1, and Z 2 is an oxygen atom or a sulfur atom, and Z 3 is a nitrogen atom or CH, and Z 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 and R c21 , R c31 , R c24 , and R c34 is a hydrogen atom, and R c22 , R c32 , R c13 , R c23 , and R c35are the same or different, and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), OR cc6 , a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom), or a cyclopropyl group (the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom). [Embodiment 4] A compound of the present invention N, wherein X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1, and Z 2 is an oxygen atom or a sulfur atom, and Z 3 is a nitrogen atom or CH, and Z 4 , Z 5 , Z 6 and Z 7 The combination is Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 and R c21 , R c31 , R c24 , and R c34 is a hydrogen atom, and R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33are the same or different and are C1-C6 chain hydrocarbon groups (the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom). 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, OR 3a or a hydrogen atom, and R 3a is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, or a hydrogen atom. 3 is a methyl group or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, OR 3a or a hydrogen atom, and R 3a is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, OR 3a or a hydrogen atom, and R 3a is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, OR3a or a hydrogen atom, and R 3a is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, OR 3a or a hydrogen atom, and R 3a is a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom. 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group B, or a hydrogen atom. [Aspect 13] A compound according to aspect 2, wherein R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group B, or a hydrogen atom. [Aspect 14] A compound according to aspect 3, wherein R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group B, or a hydrogen atom. [Aspect 15] A compound according to aspect 4, wherein R 3 is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group B, or a hydrogen atom. [Aspect 16] A compound according to aspect 1, wherein R 3 is a methyl group or a hydrogen atom. 3 is a methyl group or a hydrogen atom. 3 is a methyl group or a hydrogen atom. 3 is a methyl group or a hydrogen atom. [Embodiment 20] In the compound N of the present invention, Q is a group represented by formula B1 or a group represented by formula B2, R b11 , R b21, and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Embodiment 21] A compound N of the present invention, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 22] In aspect 1, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 23] A compound according to aspect 2, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 24] A compound according to aspect 3, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 25] A compound according to aspect 4, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 26] A compound according to aspect 5, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and Rb22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 27] A compound according to aspect 6, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 28] A compound according to aspect 7, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 29] A compound according to aspect 8, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 30] A compound according to aspect 9, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 31] A compound according to aspect 10, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 32] A compound according to aspect 11, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 33] A compound according to aspect 12, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 34] A compound according to aspect 13, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 35] A compound according to aspect 14, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 36] A compound according to aspect 15, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 37] A compound according to aspect 16, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 38] A compound according to aspect 17, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 39] A compound according to aspect 18, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 40] A compound according to aspect 19, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 are the same or different and are a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Aspect 41] A compound according to aspect 1, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 42] The compound according to aspect 2, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22is a hydrogen atom. [Aspect 43] The compound according to aspect 3, wherein Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 44] In aspect 4, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 45] In aspect 5, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 46] In aspect 6, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 47] In aspect 7, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 48] In aspect 8, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 49] In aspect 9, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 50] In aspect 10, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 51] In aspect 11, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 52] In aspect 12, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22is a hydrogen atom. [Aspect 53] In aspect 13, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 54] In aspect 14, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 55] In aspect 15, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 56] In aspect 16, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 57] In aspect 17, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 58] In aspect 18, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Aspect 59] In aspect 19, Q is a group represented by formula B1 or a group represented by formula B2, and R b11 , R b21 , and R b22 is a hydrogen atom. [Embodiment 60] In the compound N of the present invention, R １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group.１ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. １ is a methyl group. [Embodiment 120] In any of the compounds of embodiments 1 to 119 or compound N of the present invention, R ２ is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, or a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazolyl group, the thiazolyl group, the isothiazolyl group, the oxazolyl group, the isoxazolyl group, the 1,2,4-oxadiazolyl group, the 1,3,4-thiadiazolyl group, a tetrazolyl group, the 1,2,4-thiadiazolyl group, the 1,3,4-thiadiazolyl group, the 1,2,3-triazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group may be substituted with one or more substituents selected from Group A}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4, and R a11 , R a12 , R a33 , R a34 , R a42 , R a21 , R a23, and R a44 is a hydrogen atom, and R a31 , R a32 , R a53 , or R a54 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a hydrogen atom. [Embodiment 121] A compound according to any one of Embodiments 1 to 119 or Compound N of the present invention, wherein R ２ is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a thiazolyl group, a 1,2,4-oxadiazolyl group, a 1,2,4-triazolyl group, or a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazinyl group, the thiazolyl group, the 1,2,4-oxadiazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group are each a C(O)NR 13A R 14A , a cyano group, and a halogen atom}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, wherein R a11 , R a33 , R a21 , and R a23 is a hydrogen atom, and R a31 and R a53 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a hydrogen atom. [Embodiment 122] In any of the compounds of Embodiments 1 to 119 or compound N of the present invention, R ２ a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group {the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazinyl group are C(O)NR 13A R 14A, a cyano group, and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, wherein R a11 , R a33 , R a21 , and R a23 is a hydrogen atom, and R a31 and R a53 are the same or different and are a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a hydrogen atom. [Embodiment 123] A compound according to any one of Embodiments 1 to 119 or Compound N of the present invention, wherein R ２ is a pyridyl group, a pyrimidinyl group {the pyridyl group and the pyrimidinyl group are C(O)NR 13A R 14A , a cyano group, and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, wherein R a11 , R a33 , R a21 , and R a23 is a hydrogen atom, and R a31 and R a53 and are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from the group consisting of cyclopropyl groups and halogen atoms. [Embodiment 124] A compound according to any one of Embodiments 1 to 119 or Compound N of the present invention, wherein Z 1 is an oxygen atom, a sulfur atom, N—CN, or N—NO ２ A compound according to claim 120, wherein Z 1 is an oxygen atom, a sulfur atom, N—CN, or N—NO ２ A compound according to claim 126, wherein Z 1 is an oxygen atom, a sulfur atom, N—CN, or N—NO ２ [Embodiment 127] In embodiment 122, Z 1 is an oxygen atom, a sulfur atom, N—CN, or N—NO ２ [Embodiment 128] In embodiment 123, Z 1 is an oxygen atom, a sulfur atom, N—CN, or N—NO ２[Embodiment 129] In any of the compounds of Embodiments 1 to 119 or the compound N of the present invention, Z 1 is an oxygen atom. [Aspect 130] In aspect 120, Z 1 is an oxygen atom. [Aspect 131] In aspect 121, Z 1 is an oxygen atom. [Aspect 132] In aspect 122, the compound 1 is an oxygen atom. [Aspect 133] In aspect 123, the compound 1 A compound in which the oxygen atom is

[0014] Next, the method for producing the compound of the present invention will be described.

[0015] Production Method 1 The compound represented by formula (I-3) (hereinafter referred to as compound (I-3)) can be produced by reacting a compound represented by formula (I-1) (hereinafter referred to as compound (I-1)) with a compound represented by formula (I-2) (hereinafter referred to as compound (I-2)) in the presence of a carbonylating agent. [In the formula, R x31 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, a cyclopropyl group, a hydrogen atom, or OR 3aand the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), 1,4-dioxane, 1,2-dimethoxyethane, methyl tert-butyl ether, and diethyl ether (hereinafter referred to as ethers); halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbons); aprotic polar solvents such as N-methylpyrrolidone (hereinafter referred to as NMP), N,N-dimethylformamide (hereinafter referred to as DMF), and dimethyl sulfoxide (hereinafter referred to as aprotic polar solvents); water; and mixtures of two or more thereof. Examples of carbonylating agents used in the reaction include di(N-succinimidyl)carbonate, triphosgene, phosgene, thiophosgene, phenyl chloroformate, isobutyl chloroformate, ethyl chloroformate, methyl chloroformate, 1,1'-carbonyldiimidazole, di-tert-butyl dicarbonate, diphenyl carbonate, S,S'-dimethyl dithiocarbonate, 4-nitrophenyl chloroformate, 4-nitrobenzyl chloroformate, 2,4,6-trichlorobenzoyl chloride, bis(pentafluorophenyl)carbonate, and bis(4-nitrophenyl)carbonate. A base can be used in the reaction, if necessary. Examples of bases used in the reaction 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). In the reaction, compound (I-2) is usually used in a ratio of 1 to 10 moles and the carbonylating agent is usually used in a ratio of 1 to 10 moles per mole of compound (I-1). When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (I-1). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 48 hours.After completion of the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent, followed by post-treatment such as drying and concentration of the organic layer to obtain compound (I-3). Compound (I-2) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid and sulfuric acid (hereinafter referred to as inorganic acids); and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid (hereinafter referred to as organic acids). Compound (I-1) can be produced using known methods.

[0016] Production Method 2 The compound represented by formula (I-5) (hereinafter referred to as compound (I-5)) can be produced by reacting a compound represented by formula (I-4) (hereinafter referred to as compound (I-4)) with compound (I-2) in the presence of an azide. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, halogenated hydrocarbons, nitriles, aromatic hydrocarbons, and mixtures of two or more of these. Examples of azides used in the reaction include sodium azide and diphenylphosphonic acid azide. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases. In the reaction, compound (I-2) is usually used in a ratio of 1 to 10 moles and the azide is usually used in a ratio of 1 to 10 moles per mole of compound (I-4). When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (I-4). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (I-5) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (I-4) can be produced by known methods.

[0017] Production Method 3 A compound represented by formula (I-7) (hereinafter referred to as compound (I-7)) can be produced by reacting compound (I-5) with a compound represented by formula (I-6) (hereinafter referred to as compound (I-6)). [In the formula, R x32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, a cyclopropyl group, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkylsulfonyl group, C(O)R 3b , or C(O)OR 3c represents M x1 represents a leaving group such as a chlorine atom, bromine atom, or iodine atom, and other symbols have the same meaning as above. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; halogenated hydrocarbons; nitriles; aromatic hydrocarbons; aprotic polar solvents, and mixtures of two or more of these. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases and alkali metal carbonates. Compound (I-6) is usually used in a ratio of 1 to 10 moles per mole of compound (I-5). When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (I-5). The reaction temperature is usually in the range of −78°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (I-7) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment such as drying and concentrating the organic layer. Compound (I-6) is a commercially available compound or can be prepared using known methods.

[0018] Production Method 4 The compound represented by formula (I-10) (hereinafter referred to as compound (I-10)) can be produced by reacting a compound represented by formula (I-8) (hereinafter referred to as compound (I-8)) with a compound represented by formula (I-9) (hereinafter referred to as compound (I-9)) in the presence of a metal catalyst. [In the formula, M X2 represents a chlorine atom, a bromine atom, or an iodine atom; MArepresents a 9-borabicyclo[3.3.1]nonan-9-yl group, a borono group, a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, or a tributylstannyl group, and other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aromatic hydrocarbons; aprotic polar solvents; water, and mixtures of two or more of these. Examples of metal catalysts used in the reaction include palladium catalysts such as tetrakis(triphenylphosphine)palladium(0), 1,1'-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; iron catalysts such as iron(III) chloride and iron(III) acetylacetonate; copper catalysts such as copper(I) iodide and copper(I) chloride; and combinations of two or more of these. A ligand, a base, and / or an inorganic halide may be used in the reaction, as necessary. Ligands used in the reaction include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. Bases used in the reaction include organic bases and alkali metal carbonates. Inorganic halides used in the reaction include alkali metal fluorides such as potassium fluoride and sodium fluoride; and alkali metal chlorides such as lithium chloride and sodium chloride. In the reaction, compound (I-9) is usually used in a ratio of 1 to 10 moles and a metal catalyst is usually used in a ratio of 0.01 to 0.5 moles per mole of compound (I-8). When a ligand is used in the reaction, the ligand is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-8).When a base is used in the reaction, the base is typically used in a ratio of 0.1 to 5 moles per mole of compound (I-8). When an inorganic halide is used in the reaction, the inorganic halide is typically used in a ratio of 0.1 to 5 moles per mole of compound (I-8). The reaction temperature is typically in the range of -20°C to 200°C. The reaction time is typically in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-10) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. Compound (I-9) is a commercially available compound or can be produced using known methods. The reaction can also be carried out, for example, in accordance with the method described in Example H2 of WO 2020 / 070049.

[0019] Reference Production Method 1 The compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) can be produced by reacting a compound represented by formula (M-1) (hereinafter referred to as compound (M-1)) with compound (I-2) in the presence of a carbonylating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out using compound (M-1) instead of compound (I-1) according to Production Method 1. Compound (M-1) can be produced by a known method.

[0020] Reference Production Method 2 The compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) can be produced by reacting a compound represented by formula (M-3) (hereinafter referred to as compound (M-3)) with compound (I-2). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out using compound (M-3) instead of compound (I-4) according to Production Method 2. Compound (M-3) can be produced by a known method.

[0021] Reference Production Method 3 A compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) can be produced by reacting a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)) with a compound represented by formula (M-6) (hereinafter referred to as compound (M-6)). [In the formula, M x3 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a 4-methoxybenzenesulfonyloxy group, and other symbols have the same meanings as above.] A solvent can be used for the reaction, if necessary. Examples of the solvent include ethers; halogenated hydrocarbons; nitriles; aromatic hydrocarbons; aprotic polar solvents, and mixtures of two or more thereof. Compound (M-6) is typically used in a ratio of 1 to 30 moles per mole of compound (M-5). The reaction temperature is typically within the range of 0°C to 200°C. The reaction time is typically within the range of 0.1 to 48 hours. After completion of the reaction, compound (M-7) can be obtained by post-treatment, such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M-7) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compound (M-5) and compound (M-6) are commercially available compounds or can be prepared using known methods.

[0022] Reference Production Method 4 The compound represented by formula (M-9) (hereinafter referred to as compound (M-9)) can be produced by reacting a compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) with compound (M-6). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-8) instead of compound (M-5). Compound (M-9) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compound (M-8) is a commercially available compound, or can be produced using known methods.

[0023] Reference Production Method 5 The compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) can be produced by reacting a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) with compound (M-6). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-10) instead of compound (M-5). Compound (M-11) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compound (M-10) is a commercially available compound, or can be produced using a known method.

[0024] Reference Production Method 6 The compound represented by formula (M-13) (hereinafter referred to as compound (M-13)) can be produced by reacting a compound represented by formula (M-12) (hereinafter referred to as compound (M-12)) with compound (M-6). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-12) instead of compound (M-5). Compound (M-13) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compound (M-12) is a commercially available compound, or can be produced using a known method.

[0025] Reference Production Method 7 A compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) can be produced by reacting a compound represented by formula (M-14) (hereinafter referred to as compound (M-14)) with a compound represented by formula (M-15) (hereinafter referred to as compound (M-15)). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-14) instead of compound (M-5) and compound (M-15) instead of compound (M-6). Compound (M-16) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compounds (M-14) and (M-15) are commercially available compounds, or can be produced using known methods.

[0026] Reference Production Method 8 The compound represented by formula (M-19) (hereinafter referred to as compound (M-19)) can be produced by reacting a compound represented by formula (M-17) (hereinafter referred to as compound (M-17)) with a compound represented by formula (M-18) (hereinafter referred to as compound (M-18)). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-17) instead of compound (M-5) and compound (M-18) instead of compound (M-6). Compound (M-19) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compounds (M-17) and (M-18) are commercially available compounds, or can be produced using known methods.

[0027] Reference Production Method 9 The compound represented by formula (M-21) (hereinafter referred to as compound (M-21)) can be produced by reacting a compound represented by formula (M-20) (hereinafter referred to as compound (M-20)) with compound (M-18). [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Reference Production Method 3, using compound (M-20) instead of compound (M-5) and compound (M-18) instead of compound (M-6). Compound (M-21) may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids and organic acids. Compound (M-20) is a commercially available compound, or can be produced using a known method.

[0028] Reference Production Method 10 A compound represented by formula (M-23) (hereinafter referred to as compound (M-23)) can be produced by reacting a compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) with a reducing agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols such as butanol, ethanol, methanol, 2-propanol, and 2,2,2-trifluoroethanol (hereinafter referred to as alcohols); halogenated hydrocarbons; ethers; water; and mixtures of two or more thereof. Examples of the reducing agent used in the reaction include sodium cyanoborohydride, sodium triacetoxyborohydride, sodium borohydride, and 2-picoline borane. An acid can be used in the reaction, if necessary. Examples of the acid include organic acids and inorganic acids. The reducing agent used in the reaction is usually used in a ratio of 1 to 10 moles per mole of compound (M-22). When an acid is used in the reaction, the acid is usually used in a ratio of 0.1 to 10 moles per mole of compound (M-22). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After the reaction is complete, the compound (M-23) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

[0029] Reference Production Method 11 Compound (M-22) can be produced by reacting a compound represented by formula (M-24) (hereinafter referred to as compound (M-24)) with a compound represented by formula (M-25) (hereinafter referred to as compound (M-25)). [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; halogenated hydrocarbons; nitriles; aromatic hydrocarbons; aprotic polar solvents; alcohols; esters such as ethyl acetate, butyl acetate, isobutyl acetate, and isopropyl acetate (hereinafter referred to as esters); water, and mixtures of two or more thereof. An acid can be used in the reaction, if necessary. Examples of the acid used in the reaction include organic acids and inorganic acids. In the reaction, compound (M-25) is usually used in a ratio of 1 to 10 moles per mole of compound (M-24). When an acid is used in the reaction, the acid is usually used in a ratio of 0.1 to 10 moles per mole of compound (M-24). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After the reaction is complete, compound (M-22) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compounds (M-24) and (M-25) are commercially available compounds or can be produced by known methods.

[0030] Reference Production Method 12 Compound (M-23) can be produced by reacting compound (M-24) with compound (M-25) in the presence of a reducing agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols; halogenated hydrocarbons; ethers; water, and mixtures of two or more thereof. Examples of the reducing agent used in the reaction include sodium cyanoborohydride, sodium triacetoxyborohydride, sodium borohydride, and 2-picoline borane. An acid can be used in the reaction, if necessary. Examples of the acid used in the reaction include organic acids and inorganic acids. In the reaction, compound (M-25) is usually used in a ratio of 1 to 10 moles and the reducing agent is usually used in a ratio of 1 to 10 moles per mole of compound (M-24). When an acid is used in the reaction, the acid is usually used in a ratio of 0.1 to 10 moles per mole of compound (M-24). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After the reaction is complete, the compound (M-23) can be obtained by post-treatment such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

[0031] The compound of the present invention can be mixed or used in combination with one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) below (hereinafter referred to as the present component). The term "mixed or used in combination" means that the compound of the present invention and the present component are used simultaneously, separately, or with a time interval. When the compound of the present invention and the present component are used simultaneously, the compound of the present invention and the present component may be contained in separate preparations or in a single preparation. One aspect of the present invention is a composition (hereinafter referred to as Composition A) containing one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d) (i.e., the present component) and the compound of the present invention.

[0032] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride ion 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, glutamatergic chloride ion channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone receptor modulators, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial insect midgut membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation uncouplers, nicotinic acetylcholine receptor channel blockers (e.g., nereistoxin insecticides), chitin biosynthesis inhibitors, molting inhibitors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial electron transport chain complexes I and II, The group consisting of inhibitors of acetylcholine III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ nicotinamidase inhibitors, GABA-gated chloride ion channel allosteric modulators, calcium-activated potassium channel modulators, targeted suppressors via RNA interference, vesicular acetylcholine transporter inhibitors, microbial insecticides, and other arthropodicidal and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.

[0033] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.

[0034] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0035] Group (d) is a group of repellent ingredients.

[0036] Examples of combinations of the present components and the compounds of the present invention are described below. For example, alanycarb + SX refers to a combination of alanycarb and SX. The abbreviation SX refers to any one of the present compounds selected from the compound groups SX1 to SX592 and present compounds 1 to 122. The present components described below are all known and can be obtained from commercially available preparations or produced by known methods. When the present components are microorganisms, they can also be obtained from bacterial depositories. The numbers in parentheses represent CAS RNs (registered trademarks).

[0037] Combinations of the present ingredient of the above group (a) with the compound of the present invention: abamectin + SX, acephate + SX, acequinocyl + SX, acetamiprid + SX, acetoprole + SX, acrinathrin + SX, acinonapyr + SX, afidopyropen + SX, afoxolaner + SX, alanycarb + SX, aldicarb + SX, allethrin + SX, alpha-cypermethrin + SX, alpha-endosulfan + SX, aluminum phosphide + SX, Amitraz + SX, azadirachtin + SX, azamethiphos + SX, azinphos-ethyl + SX, azinphos-methyl + SX, azocyclotin + SX, Celastrus angulatus bark + SX, bendiocarb + SX, benfluthrin + SX, benfuracarb + SX, bensultap + SX, bentiofluorin + SX, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX,Bioallethrin + SX, bioresmethrin + SX, bistrifluron + SX, bisulfufen + SX, borax + SX, boric acid + SX, broflanilide + SX, bromopropylate + SX, buprofezin + SX, butocarboxim + SX, butoxycarboxim + SX, cadusafos + SX, calcium phosphide + SX, carbaryl + SX, carbofuran + SX, carbosulfan + SX, Cartap hydrochloride + SX, cartap + SX, chinomethionate + SX, chlorantraniliprole + SX, chlordane + SX, chlorethoxyfos + SX, chlorfenapyr + SX, chlorfenvinphos + SX, chlorfluazuron + SX, chlormephos + SX, chloropicrin + SX, chlorpyrifos + SX, chlorpyrifos-methyl + SX, chromafenozide + SX, clofentezine + SX, clothianidin + SX, concanamycin A + SX, coumaphos + SX, cryolite + SX,Cyanophos + SX, cyantraniliprole + SX, cybenzoxasulfyl + SX, cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, Cyphenothrin + SX, cyproflanilide + SX, cyromazine + SX, dazomet + SX, deltamethrin + SX, demeton-S-methyl + SX, diafenthiuron + SX, diazinon + SX, dichlorvos + SX, dichloromezotiaz + SX, dicofol + SX, dicrotophos + SX, diflovidazin + SX, diflubenzuron + SX, dimefluthrin + SX, Dimethoate + SX, dimethylvinphos + SX, dimpropyridaz + SX, dinotefuran + SX, disodium octaborate + SX,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) phenylphosphonothioate) + SX, epsilon-metofluthrin + SX, epsilon-momfluorothrin + SX, esfenvalerate + SX, ethiofencarb + SX, ethion + SX, Ethiprole + SX, ethoprophos + SX, etofenprox + SX, etoxazole + SX, Artemisia absinthium extract + SX, Azadirachta indica extract + SX, Cassia nigricans extract + SX, Clitoria ternatea extract + SX, Symphytum officinale extract + SX, Chenopodium ambrosioides extract + SX, Tansy extract + SX, Urtica dioica extract + SX, Mistletoe extract (extract of Viscum album) + SX,Famphur + SX, fenamiphos + SX, fenazaquin + SX, fenbutatin oxide + SX, fenitrothion + SX, fenmezoditiaz + SX, fenobucarb + SX, fenoxycarb + SX, fenpropathrin + SX, fenpyroximate + SX, fenthion + SX, fenvalerate + SX, fipronil + SX, flometoquin + SX, flonicamid + SX, Fluacrypyrim + SX, Fluazaindolizine + SX, Fluazuron + SX, Flubendiamide + SX, Fluchlordiniliprole + SX, Flucycloxuron + SX, Flucythrinate + SX, Fluensulfone + SX, Flufenoprox + SX, Flufenoxuron + SX, Flufiprole + SX, Flumethrin + SX, Flumetnicam + SX, Flupentiofenox + SX Flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX,Fluxametamide + SX, formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, Potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate salicylate + SX, isoxathion + SX, ivermectin + SX, kadethrin + SX, kappa-tefluthrin + SX,Kappa-bifenthrin + SX, kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, lotilaner + SX, lufenuron + SX, machine oil + SX, malathion + SX, mecarbam + SX, meperfluthrin + SX, metaflumizone + SX, metam + SX, methamidophos + SX, Methidathion + SX, methiocarb + SX, methomyl + SX, methoprene + SX, methoxychlor + SX, methoxyfenozide + SX, methyl bromide + SX, metofluthrin + SX, metolcarb + SX, metoxadiazone + SX, mevinphos + SX, milbemectin + SX, milbemycin oxime + SX, mivorilaner + SX, modoflaner + SX, momfluorothrin + SX Monocrotophos + SX, moxidectin + SX, naled + SX, nicofluprole + SX, nicotine + SX,Nicotine sulfate + SX, nitenpyram + SX, novaluron + SX, noviflumuron + SX, Chenopodium anthelminticum seed oil + SX, omethoate + SX, oxamyl + SX, oxazosulfyl + SX, oxydemeton-methyl + SX, parathion + SX, parathion-methyl + SX, permethrin + SX, phenothrin + SX, phenthoate + SX, phorate + SX, phosalone + SX, phosmet + SX, phosphamidon + SX, phosphine + SX, phoxim + SX, pioxaniliprole + SX, piperflanilide + SX, pirimicarb + SX, pirimiphos-methyl + SX, prallethrin + SX, profenofos + SX, profluthrin + SX, propargite + SX, propetamphos + SX, propoxur + SX, propylene glycol alginate + SX, prothiofos + SX, Piflubumide + SX, pymetrozine + SX, pyraclofos + SX,Pyrethrins + SX, pyridaben + SX, pyridalyl + SX, pyridaphenthion + SX, pyrifluquinazone + SX, pyrimidifen + SX, pyriminostrobin + SX, pyriprole + SX, pyriproxyfen + SX, quinalphos + SX, resmethrin + SX, rotenone + SX, ryanodine + SX, sarolaner + SX, selamectin + SX, sigma-cypermethrin + SX, silafluofen + SX, sodium borate + SX, sodium metaborate + SX, spidoxamat + SX, spinetoram + SX, spinosad + SX, spirobudifen + SX, spirodiclofen + SX, spiromesifen + SX, spiropidione + SX, spirotetramat + SX, sulfiflumin + SX, sulfluramid + SX, sulfotep + SX, sulfoxaflor + SX, sulfoxamyl + SX, sulfur + SX, sulfuryl fluoride + SX, tartar emetic + SX, tau-fluvalinate + SX,Tebufenozide + SX, tebufenpyrad + SX, tebupirimfos + SX, teflubenzuron + SX, tefluthrin + SX, temephos + SX, terbufos + SX, terpene constituents of the extract of Chenopodium ambrosioides near ambrosioides + SX, tetrachlorantraniliprole + SX, tetrachlorvinphos + SX, tetradifon + SX, tetramethrin + SX, tetramethylfluthrin + SX, Tetraniliprole + SX, theta-cypermethrin + SX, thiacloprid + SX, thiamethoxam + SX, thiocyclam + SX, thiodicarb + SX, thiofanox + SX, thiometon + SX, thiosultap disodium + SX, thiosultap monosodium + SX, thiapyrachlor + SX, tigolaner + SX, thioantraniliprole + SX, tioxazafen + SX, Tolfenpyrad + SX, tralomethrin + SX, transfluthrin + SX,Triazamate + SX, triazophos + SX, trichlorfon + SX, trifluenfuronate + SX, triflumezopyrim + SX, triflumuron + SX, trimethacarb + SX, trioxyflanilide + SX, tyclopyrazoflor + SX, umifoxolaner + SX, vadescana + SX, vamidothion + SX, vinylfluthrin + SX, Quassia amara wood extract + SX, XMC (3,5-dimethylphenyl N-methylcarbamate + SX, xylylcarb + SX, zeta-cypermethrin + SX, zinc phosphide + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX,N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, N-[4-chloro-2-(pyridin-3-yl)-1,3-thiazol-5-yl]-N-ethyl-3-(methanesulfonyl)propanamide + SX, 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-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)pyrrolidin-1-yl]phenyl}methyl)cyclopropanecarboxamide + SX, 7-fluoro-N-[1-(methylsulfanyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfinyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 7-fluoro-N-[1-(methanesulfonyl)-2-methylpropan-2-yl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, N-[1-(difluoromethyl)cyclopropyl]-2-(pyridin-3-yl)-2H-indazole-4-carboxamide + SX, 2,9-dihydro-9-(methoxymethyl)-2-(pyridin-3-yl)-10H-pyrazolo[3,4-f]pyrido[2,3-b][1,4]oxazepin-10-one (2607927-97-7) + SX, (S)-2-chloro-N-(3-ethylpentan-2-yl)furan-3-carboxamide + SX, Cry1Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ab protein) + SX, Cry1Ac protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Ac protein) + SX, Cry1Fa protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1Fa protein) + SX, Cry1A.105 protein from Bacillus thuringiensis (Bacillus thuringiensis Cry1A.105 protein) + SX, Cry2Ab protein from Bacillus thuringiensis (Bacillus thuringiensis Cry2Ab protein) protein) + SX, Bacillus thuringiensis-derived Vip3A protein (Bacillus thuringiensis Vip3A protein) + SX, Bacillus thuringiensis-derived mCry3A protein (Bacillus thuringiensis mCry3A protein) + SX, Bacillus thuringiensis-derived Cry3Ab protein (Bacillus thuringiensis Cry3Ab protein) + SX, Bacillus thuringiensis-derived Cry3Bb protein (Bacillus thuringiensis Cry3Bb protein) + SX, Bacillus thuringiensis-derived Cry34Ab1 / Cry35Ab1 protein (Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein) + SX,Adoxophyes orana granulovirus BV-0001 (GV strain BV-0001) + SX, Anticarsia gemmatalis multiple nucleocapsid nucleopolyhedrovirus (MNPV) + SX, Autographa californica MNPV + SX, Cydia pomonella granulosis virus V15 (GV strain V15) + SX, Cydia pomonella granulosis virus V22 (GV strain V22) + SX, Cryptophlebia leucotreta granulosis virus (GV) + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 + SX, Helicoverpa zea nucleopolyhedrovirus (NPV) + SX, Lymantria dispar nucleopolyhedrovirus (NPV) + SX, Mamestra brassicae nucleopolyhedrovirus (NPV) + SX, Mamestra configurata nucleopolyhedrovirus (NPV) + SX, Neodiprion abietis nucleopolyhedrovirus (NPV) + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae + SX,Orgyia pseudotsugata nucleopolyhedrovirus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua nucleopolyhedrovirus (MNPV) + SX, Spodoptera littoralis nucleopolyhedrovirus (MNPV) + SX, Spodoptera litura nucleopolyhedrovirus (NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX,Bacillus thuringiensis subsp. Aizawai strain NB200 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain CCT1306 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG2348 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, 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. dendrolimus + SX, Bacillus thuringiensis var. galleriae + 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, Bacillus thuringiensis var. 7216 + SX, Bacillus thuringiensis var. aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinogensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dactylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX,Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5 / F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thornei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, Wolbachia pipientis + SX。,

[0038] Combinations of the present ingredient of the above group (b) with the compound of the present invention: acibenzolar-S-methyl + SX, aldimorph + SX, ametoctradin + SX, aminopyrifen + SX, aminotipyr + SX, amisulbrom + SX, anilazine + SX, azaconazole + SX, azoxystrobin + SX, basic copper 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 + SX, boscalid + SX, bromothalonil + SX, bromuconazole + SX, bupirimate + SX, captafol + SX, captan + SX, Carbendazim + SX, carboxin + SX, carpropamid + SX, chinomethionate + SX, chitin + SX,Chlorinconazide + SX, chloroneb + ​​SX, chlorothalonil + SX, chlozolinate + SX, colletochlorin B + SX, copper(II) acetate + SX, copper(II) hydroxide + SX, copper oxychloride + SX, copper(II) sulfate + SX, coumoxystrobin + SX, cyazofamid + SX, cyflufenamid + SX, cymoxanil + SX, cyproconazole + SX, Cyprodinil + SX, dichlobentiazox + SX, dichlofluanid + SX, diclocymet + SX, diclomezine + SX, dicloran + SX, diethofencarb + SX, difenoconazole + SX, diflumetorim + SX, dimethachlone + SX, dimethirimol + SX, dimethomorph + SX, dimoxystrobin + SX, diniconazole + SX, diniconazole-M + SX SX, dinocap + SX, dipotassium hydrogenphosphite + SX, dipymetitrone + SX, dithianon + SX,Dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt + SX, dodemorph + SX, dodine + SX, edifenphos + SX, enoxastrobin + SX, epoxiconazole + SX, etaconazole + SX, ethaboxam + SX, ethirimol + SX, etridiazole + SX, garlic extract (Allium sativum) + SX, extract of the cotyledons of lupine plantlets (BLAD) + SX, horsetail extract (Equisetum arvense) + SX SX, tea tree extract (Melaleuca alternifolia) + SX, giant knotweed extract (Reynoutria sachalinensis) + SX, nasturtium extract (Tropaeolus majus) + SX, famoxadone + SX, fenamidone + SX, fenaminstrobin + SX, fenarimol + SX, fenbuconazole + SX, feneptamidoquin + SX, fenfuram + SX, fenhexamid + SX, fenopyramide + SX, fenoxanil + SX Fenpiclonil + SX, fenpicoxamid + SX,Fenpropidin + SX, fenpropimorph + SX, fenpyrazamine + SX, triphenyltin acetate + SX, triphenyltin chloride + SX, fentin hydroxide + SX, ferbam + SX, ferimzone + SX, florylpicoxamid + SX, fluazinam + SX, flubeneteram + SX, fludioxonil + SX, flufenoxadiazam + SX, flufenoxystrobin + SX, fluindapyr + SX, flumetylsulforim + SX, flumorph + SX, fluopicolide + SX, fluopyram + SX, fluopimomide + SX, fluoroimide + SX, fluoxapiprolin + SX, fluoxastrobin + SX, fluoxytioconazole + SX, fluquinconazole + SX, fluquinometoate + SX, flusilazole + SX, flusulfamide + SX, flutianil + SX, flutolanil + SX, Flutriafol + SX, fluxapyroxad + SX, folpet + SX, fosetyl + SX,Fosetyl aluminum + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + SX, galquin + SX, guazatine + SX, hexaconazole + SX, hymexazole + SX, imazalil + SX, imibenconazole + SX, iminoctadine + SX, iminoctadine triacetate + SX, inpyrfluxam + SX, iodocarb + SX, ipconazole + SX Ipfentrifluconazole + SX, ipflufenoquin + SX, iprobenfos + SX, iprodione + SX, iprovalicarb + SX, isofetamide + SX, isofleucine + SX, isoflucipram + SX, isoprothiolane + SX, isopyrazam + SX, isotianil + SX, kasugamycin + SX, kresoxim-methyl + SX, laminarin + SX, oak leaves and bark of quercus + SX, mancozeb + SX, Mandestrobin + SX, mandipropamid + SX, maneb + ​​SX, mefentrifluconazole + SX, mepanipyrim + SX,Mepronil + SX, meptyldinocap + SX, metalaxyl + SX, metalaxyl-M + SX, metarylpicoxamid + SX, metconazole + SX, metcyclofenstrobin + SX, methasulfocarb + SX, 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 fumarate + SX, oxycarboxin + SX, oxytetracycline + SX, pefurazoate + SX, penconazole + SX, pencycuron + SX, penflufen + SX, Penthiopyrad + SX, phenamacril + SX, phosphorous acid + SX, phthalide + SX, picarbutrazox + SX,Picoxystrobin + SX, piperalin + SX, polyoxins + SX, potassium hydrogencarbonate + SX, potassium dihydrogenphosphite + SX, probenazole + SX, prochloraz + SX, procymidone + SX, propamidine + SX, propamocarb + SX, propiconazole + SX, propineb + ​​SX, proquinazid + SX, prothiocarb + SX, prothioconazole + SX, pydiflumetofen + SX, Pyraclostrobin + SX, pyrametostrobin + SX, pyraoxystrobin + SX, pyrapropoyne + SX, pyraziflumid + SX, pyrazophos + SX, pyribencarb + SX, pyributicarb + SX, pyridaclomethyl + SX, pyrifenox + SX, pyrimethanil + SX, pyrimorph + SX, pyriophenone + SX, pyrisoxazole + SX, pyroquilon + SX Quillaja extract + SX, quinaminoprole + SX, quinconazole + SX,Quinofumelin + SX, quinoxyfen + SX, quintozene + SX, saponins of Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX, simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX Tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, Triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX,Trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, validamycin + SX, valifenalate + SX, vinclozolin + SX, yellow mustard powder + SX, zinc thiazole + SX, zineb + ​​SX, ziram + SX, zoxamide + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-chloro-4-(2-fluorophenoxy)-2-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-(2-chloro-4-phenoxy-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2062599-39-5) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-methyl-5-methoxyphenyl]-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, [4-(difluoromethoxy)phenyl]methyl 4-[(N-ethyl-N-methylamino)methylidene]amino-2,5-dimethylbenzoate + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (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, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX,5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, N-ethyl-2-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N,2-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)cyclopropanecarboxamide + SX, N-methoxy-N'-methyl-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N'-ethyl-N-methoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N'-dimethoxy-N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX,N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, 3-(4-bromo-7-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromoindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(7-bromo-4-fluoroindol-1-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, 3-(3,5-dichloropyridin-2-yl)butan-2-yl N-{[3-(acetoxymethoxy)-4-methoxypyridin-2-yl]carbonyl}-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-hydroxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (1S)-1-[1-(naphthalen-1-yl)cyclopropyl]ethyl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (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)propanamide + SX, N-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, 3,3,3-trifluoro-N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)propanamide + SX, N-({2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)butanamide + SX, N-methoxy-N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N,N-diethyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, N-methyl-N'-({ 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)urea + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)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)isoxazolidin-3-one + SX, 3,3-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)piperidin-2-one + SX, 2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1,2-oxazinan-3-one + SX, 1-({3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)azepan-2-one + SX, 4,4-dimethyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, 5-methyl-1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)pyrrolidin-2-one + SX, ethyl 1-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)-1H-pyrazole-4-carboxylate + 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)propanoate + SX, ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + SX, methyl 2-[2-(trifluoromethyl)-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate + 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-imidazole-5-carbonitrile + SX, ethyl 1-[(4-{[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, ethyl 1-[(4-{[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy}phenyl)methyl]-1H-pyrazole-4-carboxylate + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide + SX, 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-(spiro[3.4]octan-1-yl)-5-methylthiazole-4-carboxamide + SX, 2-[cyano(2,6-difluoropyridin-4-yl)amino]-N-hexyl-5-methylthiazole-4-carboxamide + SX, 2-[acetyl(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methoxyacetyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2-methylpropanoyl)(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-[(2,6-difluoropyridin-4-yl)amino]-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxetan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxolan-3-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX, 2-{[(oxan-4-yl)carbonyl](2,6-difluoropyridin-4-yl)amino}-N-(2,2-dimethylcyclobutyl)-5-methylthiazole-4-carboxamide + SX,5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine + SX, 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(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]oxy}pyrimidine + SX, 3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX,(5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(4-bromo-2-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, 3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}-3-methylbutan-2-yl)-2,2-dimethylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(2-methoxyphenyl)-2-hydroxyethyl]-5-[(E)-1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, N-((2S)-1-{3-[2-(5-fluoro-2-methoxyphenyl)-2-(2-cyanoethoxy)ethyl]-5-[1-(isopropoxyimino)ethyl]-2,6-dioxo-3,6-dihydropyrimidin-1(2H)-yl}propan-2-yl)-2-methylpropanamide + SX, methyl ({5-[1-(2,6-difluoro-4-isopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-cyclopropylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, methyl ({5-[1-(2,6-difluoro-4-methoxyphenyl)-1H-pyrazol-3-yl]-2-methylphenyl}methyl)carbamate + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline + SX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-6-fluoro-3,3-dimethylisoquinolin-4(3H)-one + SX, 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-cyanopyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2S)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-[(2R)-2-(6-chloro-4-methoxypyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(2,4-difluorophenyl)isoxazole-3-carboxamide + SX, N-(2-{6-[(1E)-(methoxyimino)ethyl]pyridin-2-yl}-2-(1-methylpyrazol-4-yl)propyl)-5-(2,4-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, methyl 6-(2-{[5-(2,4-difluorophenyl)isoxazole-3-carbonyl]amino}-1-methyl-1-(1-methylpyrazol-4-yl)ethyl)pyridine-3-carboxylate + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-4-yl)propyl]-5-(3,5-difluoropyridin-2-yl)isoxazole-3-carboxamide + SX, N-[2-(6-chloropyridin-2-yl)-2-(1-methylpyrazol-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-difluoropyridin-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(TM) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX,Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain 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, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB / BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002 / AQ30002 + SX, Bacillus subtilis strain QST30004 / AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX,Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON / M / 91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp. carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis 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 strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain 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 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 T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX。,

[0039] Combinations of the present ingredient in group (c) above with the compound of the present invention: 1-methylcyclopropene + SX, 1,3-diphenylurea + SX, 2,3,5-triiodobenzoic acid + SX, (1H-indol-3-yl)acetic acid (IAA) + SX, 4-(1H-indol-3-yl)butyric acid (IBA) + SX, 2-(4-chloro-2-methylphenoxy)acetic acid (MCPA) + SX, 4-(4-chloro-2-methylphenoxy)butyric acid (MCPB) + SX, 4-chlorophenoxyacetic acid (4-CPA) + 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 chloride + 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 + 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, sintophen + SX, sodium 1-naphthaleneacetate + SX, sodium 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]propan-1-ol + SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium 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 + SX, Bradyrhizobium japonicum TA-11 + SX,Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium 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 Mosaik Virus weak strain + SX. ,

[0040] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.

[0041] The ratio of the compound of the present invention to the present component is not particularly limited, and examples thereof include a weight ratio (compound of the present invention:present component) of 1000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, 1:50, and the like.

[0042] The compound of the present invention is effective against harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Examples of harmful arthropods, harmful nematodes, and harmful mollusks include the following.

[0043] Hemiptera: Small brown planthopper (Laodelphax striatellus), Brown planthopper (Nilaparvata lugens), White-backed planthopper (Sogatella furcifera), Corn planthopper (Peregrinus maidis), Yellow leafhopper (Javesella pellucida), Black horned planthopper (Perkinsiella saccharicida), Tagosodes orizicolus, Stenocranus pacificus and other Delphacidae; Green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), Black-striped green rice leafhopper (Nephotettix nigropictus), Lightning leafhopper (Recilia dorsalis), Tea green leafhopper (Empoasca Cicadellidae, such as the potato leafhopper (Empoasca fabae), the corn leafhopper (Dalbulus maidis), the giant leafhopper (Cofana spectra), and Amrasca biguttula biguttula; Aphrophoridae, such as the European spittlebug (Philaenus spumarius); Aphrophoridae, such as the blue-leaved grasshopper (Geisha distinctissima); Cercopidae, such as the Chinese grasshopper (Ricania shantungensis); Mahanarva posticata and Mahanarva fimbriolata;Black bean aphid (Aphis fabae), soybean aphid (Aphis glycines), cotton aphid (Aphis gossypii), European apple aphid (Aphis pomi), willow aphid (Aphis spiraecola), green peach aphid (Myzus persicae), strawberry aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), false radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat collar aphid (Rhopalosiphum padi), corn aphid (Rhopalosiphum maidis), citrus black aphid (Toxoptera citricida), peach butterbur aphid (Hyalopterus pruni), barnyard millet aphid (Melanaphis sacchari), Japanese black aphid (Tetraneura nigriabdominalis), cotton aphid (Ceratovacuna lanigera), apple aphid (Eriosoma lanigerum), English grain aphid (Sitobion avenae), etc. Aphididae; grape aphid (Daktulosphaira vitifoliae), pecan phylloxera (Phylloxera devastatrix), pecan leaf phylloxera (Phylloxera notabilis), southern pecan leaf phylloxera (Phylloxera Phylloxeridae, such as (Russelae);Adelgidae, such as the Japanese hemlock aphid (Adelges tsugae), the balsam woolly aphid (Adelges piceae), and the small brown aphid (Aphrastasia pectinatae); Scotinophara lurida, Scotinophara coarctata, Nezara antennata, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, and Nezara Pentatomidae, such as the brown stink bug (Euschistus heros), the red-banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus, and the spotted stink bug (Piezodorus hybneri); Cydnidae, such as the narrow-banded stink bug (Riptortus clavatus), the spider stink bug (Leptocorisa chinensis), and the narrow-banded stink bug (Leptocorisa acuta); Cletus punctiger, Leptoglossus Coreidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus; Lygaeidae, such as Cavelerius saccharivorus, Togo hemipterus, and Blissus leucopterus;Miridae (Miridae) such as the red-bearded green rice bug (Trigonotylus caelestialium), the red-striped rice bug (Stenotus rubrovittatus), the long-spined wheat rice bug (Stenodema calcarata), and the rusty rice bug (Lygus lineolaris); Aleyrodidae (Aleyrodidae) such as the greenhouse whitefly (Trialeurodes vaporariorum), the tobacco whitefly (Bemisia tabaci), the citrus whitefly (Dialeurodes citri), the citrus spine whitefly (Aleurocanthus spiniferus), the tea spine whitefly (Aleurocanthus camelliae), and the Japanese oak leaf butterflies (Pealius euryae); cyanophylli), red scale (Aonidiella aurantii), pear scale (Diaspidiotus perniciosus), mulberry scale (Pseudaulacaspis pentagona), Yanon scale (Unaspis yanonensis), false Yanon scale (Unaspis citri) and other scale insects (Diaspididae); Coccidae such as ruby ​​scale (Ceroplastes rubens); Margarodidae such as Icerya purchasi and yellow cotton scale (Icerya seychellarum);Pseudococcidae, such as the eggplant mealybug (Phenacoccus solani), the sable mealybug (Phenacoccus solenopsis), the wisteria mealybug (Planococcus kraunhiae), the mulberry mealybug (Pseudococcus comstocki), the citrus mealybug (Planococcus citri), the moth mealybug (Pseudococcus calceolariae), the long-legged mealybug (Pseudococcus longispinus), and the tuttlemey bug (Brevennia rehi); the citrus psyllid (Diaphorina citri), the citrus psyllid (Trioza erytreae), the pear psyllid (Cacopsylla pyrisuga), and the Chinese pear psyllid (Cacopsylla Psyllidae, such as the Japanese chinensis, the potato psyllid (Bactericera cockerelli), and the cacopsylla (Cacopsylla pyricola); Tingidae, such as the plane tree earworm (Corythucha ciliata), the goldenrod earworm (Corythucha marmorata), the Japanese pear earworm (Stephanitis nashi), and the azalea earworm (Stephanitis pyrioides); Cimicidae, such as the bedbug (Cimex lectularius) and the netted whitefly (Cimex hemipterus); Cicadidae, such as the Quesada gigas; Triatoma infestans, Triatoma rubrofasciata, and Triatoma Reduviidae, such as the Venezuelan assassin bug (Rhodonius prolixus);

[0044] Lepidoptera: Chilo suppressalis, Dark-headed stem borer, Chilo polychrysus, White stem borer, Scirpophaga innotata, Scirpophaga incertulas, Rupela albina, Rice leaf borer, Cnaphalocrocis medinalis, Marasmia patnalis, Rice casino borer, Marasmia exigua, Cotton borer, Notarcha derogata, European corn borer, Ostrinia furnacalis, European corn borer, Hellula undalis, Black-spotted corn borer, Herpetogramma luctuosale, Rice stalk moth, Nymphula Crambidae, such as the sugarcane borer (Diatraea saccharalis), the eggplant fruit borer (Leucinodes orbonalis), and the peach moth (Conogethes punctiferalis); Pyralidae, such as the corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the two-spotted moth (Euzophera batangensis), and the striped moth (Cadra cautella);Common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), armyworm (Mythimna separata), armyworm (Mamestra brassicae), rice armyworm (Sesamia inferens), white armyworm (Spodoptera mauritia), two-banded cutworm (Naranga aenescens), leaf fall armyworm (Spodoptera frugiperda), African armyworm (Spodoptera exempta), Spodoptera cosmioides, semi-tropical armyworm (Spodoptera eridania), red cutworm (Agrotis ipsilon), turnip cutworm (Agrotis segetum), red rice looper (Autographa nigrisigna), rice yellow looper (Plusia festucae), soybean Trichoplusia spp. such as the common looper (Chrysodeixis includens), the fig goldfly (Chrysodeixis eriosoma), the three-leaved goldfly (Ctenoplusia agnata), and the nettle silverfly (Trichoplusia ni); Heliothis spp. such as the false tobacco budworm (Heliothis virescens); Helicoverpa spp. such as the cotton bollworm (Helicoverpa armigera) and the corn earworm (Helicoverpa zea); Noctuidae such as the velvet bean caterpillar (Anticarsia gemmatalis), the cotton leafworm (Alabama argillacea), and the hop wine borer (Hydraecia immanis); undans and other Lasiocampidae; Pieridae, such as Pieris rapae;Pear fruit moth (Grapholita molesta), plum fruit moth (Grapholita dimorpha), bean fruit moth (Leguminivora glycinivorella), adzuki bean pea moth (Matsumuraeses azukivora), apple smaller tortrix (Adoxophyes orana fasciata), tea smaller tortrix (Adoxophyes honmai), tea tortrix (Homona magnanima), green tea tortrix (Archips fuscocupreanus), codling moth (Cydia pomonella), citrus fruit borer (Tetramoera schistaceana), bean shoot borer (Epinotia aporema), citrus fruit borer (Citripestis sagittiferella), European grape wine moth (Lobesia Tortricidae such as Caloptilia theivora and Phyllonorycter ringoniella; Gracilariae such as Carposinidae; Leucoptera coffeella, Lyonetiidae such as Lyonetia clerkella, Lyonetia prunifoliella; Lymantria spp. such as Lymantria dispar, Euproctis spp. such as Euproctis pseudoconspersa; Plutella xylostella Plutellidae, such as Plutellidae (Plutella xylostella);Gelechiidae, such as the peach leaf moth (Anarsia lineatella), the potato leaf moth (Helcystogramma triannulella), the red cotton moth (Pectinophora gossypiella), the potato tuber moth (Pthorimaea operculella), and the tomato leaf moth (Tuta absoluta); Arctiidae, such as the American fall webworm (Hyphantria cunea); Castniidae, such as the giant sugarcane borer (Telchin licus); Cossidae, such as the small box moth (Cossus insularis); Bat moth, such as the bat moth (Endoclita excrescens); Ascotis selenaria, Biston Geometridae such as Monema flavescens, Narosoideus flavidorsalis, and Parasa lepida; Limacodidae such as Stathmopodidae, Stathmopoda masinissa; Sphingidae such as Acherontia lachesis, Agrius convolvuli, and Psilogramma increta; Nokona feralis, Synanthedon hector, and Synanthedon Sesiidae (Sesiidae) such as Tenuis; Hesperiidae (Hesperiidae) such as Parnara guttata; Tineidae (Tinea translucens) and Tineola bisselliella; Psychidae (Psychidae) such as Eumeta minuscula and Eumeta japonica.

[0045] Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Stenchaetothrips biformis, Echinothrips americanus, and Scirtothrips perseae; Phlaeothripidae such as Haplothrips aculeatus.

[0046] Diptera: Anthomyiidae such as Delia platura, Delia antiqua, and Pegomya cunicularia; Ulidiidae such as Tetanops myopaeformis; Agromyzidae such as Agromyza oryzae, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae such as Chlorops oryzae; Bactrocera Tephritidae, such as the Oriental fruit fly (Bactrocera dorsalis), the eggplant fly (Bactrocera latifrons), the olive fruit fly (Bactrocera oleae), the Queensland fruit fly (Bactrocera tryoni), the Mediterranean fruit fly (Ceratitis capitata), the apple maggot (Rhagoletis pomonella), and the cherry fruit fly (Rhacochlaena japonica); Ephydridae, such as the rice leafminer (Hydrellia griseola), the Asian rice leafminer (Hydrellia philippina), and the rice leafminer (Hydrellia sasakii); Drosophila suzukii Drosophilidae, such as Drosophila suzukii and Drosophila melanogaster; Phoridae, such as Megaselia spiracularis; Psychodidae, such as Clogmia albipunctata;Sciaridae (Sciaridae) such as Bradysia difformis and Bradysia odoriphaga; Cecidomyiidae (Cecidomyiidae) such as Mayetiola destructor and Orseolia oryzae; Diopsidae (Diopsis macrophthalma); Glossinidae (Tsetse flies) such as Glossina palpalis and Glossina morsitans; Simuliidae (Simuliidae) such as Simulium japonicum and Simulium damnosum; Phlebotominae (Phlebotominae); Tipula aino (Craned fly), Tipula oleracea (Common crane fly), and Tipula Tipulidae such as Culex pipiens pallens, Culex tritaeniorhynchus, Culex pipiens f. molestus, Culex quinquefasciatus, Culex pipiens pipiens, Culex vishnui, Aedes albopictus, Aedes aegypti, Anopheles sinensis, Anopheles gambiae, Anopheles stephensi, Anopheles coluzzii, Anopheles albimanus, Anopheles sundaicus, Anopheles mosquito family (Culicidae) such as arabiensis, Anopheles funestus, Anopheles darlingi, Anopheles farauti, Anopheles minimus;Simulidae (Family Simuliidae) such as Prosimulium yezoensis and Simulium ornatum; Tabanidae (Family Tabanus trigonus) and other such flies; Muscidae (Family Musca domestica), Muscina stabulans, Stomoxys calcitrans, Haematobia irritans and other such flies; Calliphoridae (Family Sarcophagidae); Chironomidae (Family Chironomidae) such as Chironomus plumosus, Chironomus yoshimatsui, Glyptotendipes tokunagai and other such midges; Fannidae (Family Fannidae);

[0047] Coleoptera: Diabrotica spp. (e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica balteata), Cucumber beetle (Diabrotica speciosa), etc.), Bean leaf beetle (Cerotoma trifurcata), Red-necked leaf beetle (Oulema melanopus), Cucumber leaf beetle (Aulacophora femoralis), Striped flea beetle (Phyllotreta striolata), Cabbage leaf beetle (Phyllotreta cruciferae), Western black leaf beetle (Phyllotreta pusilla, cabbage stem beetle (Psylliodes chrysocephala), hop beetle (Psylliodes punctulata), Colorado potato beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn beetle (Chaetocnema pulicaria), sweet potato leaf beetle (Chaetocnema confinis), potato beetle (Epitrix cucumeris), rice spur beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), four-spotted tortoise beetle (Laccoptera quadrimaculata), tobacco flea beetle (Epitrix hirtipennis), radish leaf beetle (Phaedon Chrysomelidae, such as the two-striped leaf beetle (Medythia nigrobilineata);Carabidae beetles such as the seed corn beetle (Stenolophus lecontei) and the slender seed corn beetle (Clivina impressifrons); Phyllophaga spp. such as the cuprea beetle (Anomala cuprea), the rufocuprea beetle (Anomala rufocuprea), the green beetle (Anomala albopilosa), the Japanese beetle (Popillia japonica), the long-legged beetle (Heptophylla picea), the European chafer (Rhizotrogus majalis), the black marsh beetle (Tomarus gibbosus), the black beetle (Holotrichia spp.), and the June beetle (Phyllophaga crinita); Diloboderus spp. such as Diloboderus abderus. Scarabaeidae (Scarabaeidae) such as Araecerus coffeae (Boll weevil); Anthriibidae (Anthriibidae) such as Cylas formicarius (Sweet potato weevil); Bruchidae (Brachiidae) such as Zabrotes subfasciatus (Brazilian bean weevil); Scolytidae (Scolytidae) such as Tomicus piniperda (Pine bark beetle), Hypothenemus hampei (Coffee berry borer);Potato weevil (Euscepes postfasciatus), alfalfa weevil (Hypera postica), maize weevil (Sitophilus zeamais), rice weevil (Sitophilus oryzae), granaria weevil (Sitophilus granarius), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), white grain weevil (Rhabdoscelus lineaticollis), boll weevil (Anthonomus grandis), grass band weevil (Sphenophorus venatus), southern cornbill bug (Sphenophorus callosus), soybean stalk weevil (Sternechus subsignatus), sugarcane weevil (Sphenophorus levis), rust gourd weevil (Scepticus Aracanthus spp. such as Aracanthus griseus, Scepticus uniformis, Aracanthus mourei, and the cotton root borer (Eutinobothrus brasiliensis) are also found in the Curculionidae family; Aracanthus laevis such as Rhynchites heros, and the Tenebrionidae family such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus; Coccinellidae such as Epilachna vigintioctopunctata, and the flat-headed ladybird beetle (Lyctus brunneus), and the rice-leaf bollworm (Rhizopertha dominica); Ptinidae;Cerambycidae such as Anoplophora malasiaca, Migdolus fryanus, Aromia bungii, Anoplophora glabripennis, and Psacothea hilaris; Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp., and Limonius spp. Elateridae (Elateridae) such as Aeolus spp. and Aeolus spp.; Staphylinidae (Staphylinidae) such as Paederus fuscipes; Dermestidae (Dermestidae) such as Anthrenus verbasci, Dermestes maculates, and Trogoderma granarium; Anobiidae (Anobiidae) such as Lasioderma serricorne and Stegobium paniceum; Cryptolestes Laemophloeidae, such as Oryzaephilus ferrugineus; Silvanidae, such as Oryzaephilus surinamensis; and Nitididae, such as Brassicogethes aeneus, a blossom beetle.

[0048] Orthoptera: Migratory locust (Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red locust (Nomadacris septemfasciata), Brown locust (Locustana pardalina), Tree locust (Anacridium melanorhodon), Italian locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two-striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-legged grasshopper (Melanoplus femurrubrum), Clear-winged grasshopper (Camnula pellucida), Desert grasshopper (Schistocerca The grasshoppers (Acrididae) include the common locust (Oxya gregaria), yellow-winged locust (Gastrimargus musicus), sparse-throated locust (Austracris guttulosa), oriental grasshopper (Oxya yezoensis), long-winged locust (Oxya japonica), and Taiwan grasshopper (Patanga succincta); the grasshoppers (Gryllotalpidae) include the common house cricket (Gryllotalpa orientalis); the crickets (Gryllidae) include the European house cricket (Acheta domestica) and the field cricket (Teleogryllus emma); and the katydids (Tettigoniidae) include the Mormon cricket (Anabrus simplex).

[0049] Hymenoptera: Tenthredinidae such as Athalia rosae and Athalia japonica; Solenopsis spp. such as Solenopsis invicta and Solenopsis geminata, Atta spp. such as Atta capiguara, Acromyrmex spp., Paraponera clavata, Ochetellus glaber, Monomorium pharaonis, Linepithema humile, Formica japonica, Pristomyrmex punctutus, Pheidole Camponotus spp. such as Camponotus noda, Pheidole megacephala, Camponotus japonicus, Camponotus obscuripes, Pogonomyrmex spp. such as Pogonomyrmex occidentalis, Wasmania spp. such as Wasmania auropunctata, Tapinoma sessile, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa Vespidae, such as Vespidae analis, Vespa velutina, and Polistes jokahamae; Siricidae, such as Urocerus gigas; and Bethylidae.

[0050] Blattodea: Ectobiidae, such as the German cockroach (Blattella germanica); Blattidae, such as the American cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the American cockroach (Periplaneta australasiae), the brown cockroach (Periplaneta brunnea), and the Asian cockroach (Blatta orientalis); Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Odontotermes formosanus, and Neotermes Termites of the family Termitidae, such as the Satsuma termite (Glyptotermes satsumensis), Nakajima termite (Glyptotermes nakajimai), Katan termite (Glyptotermes fuscus), Hodotermopsis sjostedti, Koshu termite (Coptotermes guangzhouensis), Amami termite (Reticulitermes amamianus), Miyatake termite (Reticulitermes miyatakei), Formosan termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Snocapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans.

[0051] Order Siphonaptera: Family Pulicidae such as human flea (Pulex irritans), cat flea (Ctenocephalides felis), dog flea (Ctenocephalides canis), rat flea (Xenopsylla cheopis), chicken flea (Echidnophaga gallinacea), etc.; Family Hectopsyllidae such as sand flea (Tunga penetrans); Family Ceratophyllidae such as European rat flea (Nosopsyllus fasciatus).

[0052] Psocodae: Pediculidae, such as head louse (Pediculus humanus capitis); Pthiridae, such as pubic louse (Pthirus pubis); Haematopinidae, such as cow louse (Haematopinus eurysternus) and pig louse (Haematopinus suis); Linognathidae, such as cow louse (Linognathus vituli), sheep trunk louse (Linognathus ovillus), and woolly cow louse (Solenopotes capillatus); Bovicola bovis, sheep louse (Bovicola ovis), Bovicola breviceps, Damalinia Bovicoliidae, such as Trichodectes canis and Felicola subrostratus; Menoponidae, such as Menopon gallinae, Menacanthus stramineus, and Trinoton spp.; Trimenoponidae, such as Cummingsia spp.; Trogiidae, such as Trogium pulsatorium; Liposcelis corrodens and Liposcelis Liposcelidae or Liposcelididae, such as Liposcelis bostrychophila, Liposcelis pearmani, and Liposcelis entomophila.

[0053] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0054] Acari: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.; Aculops pelekassi, Aculops citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Aculops spp. Eriophyidae such as Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae;Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis japonica, Haemaphysalis campanulata, Dermacentor variabilis, Dermacentor taiwanensis, Rocky Mountain wood tick (Dermacentor andersoni), Dermacentor reticulatus, Ixodes ovatus, Ixodes persulcatus, Black-legged tick (Ixodes scapularis), Western black-legged tick (Ixodes pacificus), Ixodes holocyclus, Ixodes ricinus, Lone star tick (Amblyomma Ixodidae ticks such as Amblyomma americanum, Amblyomma maculatum, Rhipicephalus microplus, Rhipicephalus annulatus, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, and Rhipicephalus decoloratus; Argasidae ticks such as Argas persicus, Ornithodoros hermsi, and Ornithodoros turicata; Acaridae ticks such as Tyrophagus putrescentiae and Tyrophagus similis; Dermatophagoides farinae and Dermatophagoides pteronyssinus. Pyroglyphidae, such as Pteronyssinus;Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, Chelacaropsis moorei, and Cheyletiella yasguri; Psoroptidae such as Psoroptes ovis, Psoroptes equi, Knemidocoptes mutans, Otodectes cynotis, and Chorioptes spp.; Notoedres cati, Notoedres muris, and Sarcoptes Sarcoptidae such as (Scabiei); Listrophoridae such as (Listrophorus gibbus); Dermanyssidae such as (Dermanyssus gallinae); Macronyssidae such as (Ornithonyssus sylviarum) and (Ornithonyssus bacoti); Varroa destructor such as (Varroa jacobsoni); Demodicidae such as (Demodex canis) and (Demodex cati); Leptotrombidium akamushi and (Leptotrombidium Trombiculidae, such as Leptotrombidium scutellare, Leptotrombidium pallidum, and Leptotrombidium scutellare.

[0055] Araneae: Eutichuridae, such as Cheiracanthium japonicum; Theridiidae, such as Latrodectus hasseltii. Polydesmida: Paradoxosomatidae, such as Oxidus gracilis and Nedyopus tambanus. Isopoda: Armadillidiidae, such as Armadillidium vulgare. Chilopoda: Scutigeridae such as Thereuonema hilgendorfi; Scolopendridae such as Scolopendra subspinipes; Ethopolyidae such as Bothropolys rugosus. Class Gastropoda: Family Limacidae such as the brown slug (Limax marginatus) and the yellow slug (Limax flavus); Family Philomycidae such as the slug (Meghimatium bilineatum); Family Ampullariidae such as the apple snail (Pomacea canaliculata); Family Lymnaeidae such as the lymnae snail (Austropeplea ollula).

[0056] Nematoda: Aphelenchoididae, such as the rice root-lesion nematode (Aphelenchoides besseyi); Pratylenchidae, such as Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus neglectus, and Radopholus similis; Meloidogyne javanica, Meloidogyne incognita, guava root-knot nematodes (Meloidogyne enterolobii), Meloidogyne hapla, soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera Heteroderidae such as Globodera rostochiensis, potato white cyst nematode (Globodera pallida), and Colombian root-knot nematode (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; Parasitaphelenchidae such as Bursaphelenchus xylophilus.

[0057] The harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes that have reduced chemical sensitivity or have developed chemical resistance to insecticides, acaricides, molluscicides, or nematocides.

[0058] The method for controlling arthropod pests of the present invention is carried out by applying an effective amount of the compound of the present invention or composition A directly to the arthropod pests and / or to the habitat of the arthropod pests (plants, soil, houses, animals, etc.). Examples of the method for controlling arthropod pests of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, fumigation treatment, water surface treatment, and seed treatment.

[0059] The compound of the present invention or Composition A is typically formulated into aqueous suspensions, oil suspensions, oil solutions, emulsifiable concentrates, emulsions, microemulsions, microcapsule formulations, wettable powders, water dispersible granules, dusts, granules, tablets, aerosols, resin formulations, etc. by mixing an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier with a surfactant, and optionally adding formulation adjuvants such as binders, dispersants, and stabilizers. In addition to these formulations, the compound of the present invention or Composition A can also be formulated into dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.

[0060] Examples of solid carriers include clay (pyrophyllite clay, kaolin clay, etc.), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, fine powder and granular chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and resins (polyethylene, polypropylene, polyester, polyurethane, polyamide, polyvinyl chloride, etc.).

[0061] Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, etc.), aromatic hydrocarbons (xylene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, methyl oleate, propylene carbonate, etc.), nitriles (acetonitrile, etc.), ethers (ethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, N,N-dimethyloctanamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), and vegetable oils (soybean oil, etc.).

[0062] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0063] Examples of surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol fatty acid esters, etc.) and anionic surfactants (alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, etc.).

[0064] Other formulation adjuvants include binders, dispersants, colorants, stabilizers, etc., and specific examples include polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), acid isopropyl phosphate, and dibutylhydroxytoluene.

[0065] Furthermore, adjuvants can be used as components that enhance or support the efficacy of the compound of the present invention. Specific examples include AgriDex (registered trademark), Induce (registered trademark), Gramin S (registered trademark), Genamin T 200BM (registered trademark), Silwet L77 (registered trademark), Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol Gold (registered trademark), BreakThru (registered trademark), Sundance II (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), UAN (Urea Ammonium Sulfate), and the like. Nitrate (urea ammonium nitrate), AdGreen (registered trademark), Mees (trademark), Rumba (registered trademark), Strides (registered trademark), Partner, Orix (registered trademark), Penetrator, and the like.

[0066] In the present invention, the plant includes the whole plant, stems and leaves, flowers, spikes, fruits, trunks, branches, crowns, seeds, vegetative reproductive organs, and seedlings.

[0067] Vegetative reproductive organs refer to plant roots, stems, leaves, and other parts that can grow when separated from the main body and placed in 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. Stolons are sometimes called runners, and propagules are also called bulbils and are divided into broad buds and bulbils. Vines refer to shoots (a collective term for leaves and stems) of plants such as sweet potatoes and Japanese yams. Bulbs, corms, tubers, rhizomes, stem fragments, rhizophores, and tuberous roots are collectively called bulbils. Potato cultivation begins by planting tubers in the soil, and the tubers used are generally called seed potatoes.

[0068] Examples of the method for controlling harmful arthropods by applying an effective amount of the compound of the present invention or composition A to soil include a method of applying an effective amount of the compound of the present invention or composition A to soil before or after planting a plant. More specifically, for example, planting hole treatment (spraying in planting holes, mixing in planting hole treatment soil), plant base treatment (spraying in planting holes, mixing in plant base soil, plant base irrigation, plant base treatment in the latter half of the seedling raising period), planting furrow treatment (spraying in planting furrows, mixing in planting furrow soil), row treatment (row spraying, row soil mixing, row spraying in the growing season), row treatment at sowing (row spraying at sowing, mixing in row soil at sowing), overall treatment (overall soil spraying, overall soil mixing), side row treatment, water surface treatment (water surface application, water surface application after flooding), other soil spray treatments (foliar spraying of granules during the growing season, spraying under the crown or around the main trunk, soil surface spraying, soil surface mixing, seeding hole spraying, furrow surface spraying, spraying between plants), and others. Other irrigation treatments include soil irrigation, seedling irrigation, chemical injection treatment, ground level irrigation, chemical drip irrigation, chemigation), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling tray treatments (seedling tray spraying, seedling tray irrigation, seedling tray flooding), seedling bed treatments (seedling bed spraying, seedling bed irrigation, water seedling bed spraying, seedling immersion), bed soil mixing treatments (bed soil mixing, bed soil mixing before sowing, spraying before soil covering at sowing, spraying after soil covering at sowing, covering soil mixing), and other treatments (hilling soil mixing, plowing in, topsoil mixing, rain-drop soil mixing, planting position treatment, granular inflorescence spraying, paste fertilizer mixing).

[0069] Seed treatments include, for example, treatment of seeds or vegetative reproductive organs with the compound of the present invention or Composition A. More specifically, examples include spray treatments in which a suspension of the compound of the present invention or Composition A is sprayed onto the surface of seeds or vegetative reproductive organs in a mist; smear treatments in which the compound of the present invention or Composition A is applied to seeds or vegetative reproductive organs; immersion treatments in which seeds or vegetative reproductive organs are immersed in a solution of the compound of the present invention or Composition A for a certain period of time; and methods of coating seeds or vegetative reproductive organs with a carrier containing the compound of the present invention or Composition A (film coating treatment, pellet coating treatment, etc.). Seed potatoes are particularly examples of the vegetative reproductive organs mentioned above. When applying Composition A to seeds or vegetative reproductive organs, Composition A can be applied to the seeds or vegetative reproductive organs as a single formulation, or different formulations of Composition A can be applied to the seeds or vegetative reproductive organs in multiple separate applications. Examples of methods for treating seeds or vegetative reproductive organs with multiple different formulations of Composition A include a method of treating seeds or vegetative reproductive organs with a formulation 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 formulation containing this ingredient; and a method of treating seeds or vegetative reproductive organs with a formulation 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 formulation containing a component other than the component already treated. In the present invention, "seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A" refers to seeds or vegetative reproductive organs to which the compound of the present invention or Composition A is attached. The seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A may have materials other than the compound of the present invention or Composition A attached to them before or after the compound of the present invention or Composition A is attached to the seeds or vegetative reproductive organs. Furthermore, when Composition A is attached to the surface of the seeds or vegetative reproductive organs in layers, the layers may consist of one layer or multiple layers. Furthermore, when the layer consists of multiple layers, each layer may contain one or more active ingredients, or may consist of a layer containing one or more active ingredients and a layer containing no active ingredients. Seeds or vegetative reproductive organs carrying the compound of the present invention or Composition A can be obtained, for example, by applying a formulation containing the compound of the present invention or Composition A to seeds or vegetative reproductive organs by the seed treatment method described above.

[0070] When the compound of the present invention or composition A is used for controlling harmful arthropods in the agricultural field, the application amount is 10,000 m 2 The amount of the compound of the present invention is usually 1 to 10,000 g per kg of seed or vegetative reproductive organ. When treating seeds or vegetative reproductive organs, the compound of the present invention is usually applied in an amount within the range of 0.001 to 100 g per kg of seed or vegetative reproductive organ. When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate, etc., it is usually applied after being diluted with water to an active ingredient concentration of 0.01 to 10,000 ppm, and granules, dusts, etc. are usually applied as is.

[0071] The compound of the present invention or composition A can also be applied by wrapping a resin preparation in the form of a sheet or string around the crop, stretching it near the crop, or spreading it on the soil around the base of the plant.

[0072] When the compound of the present invention or composition A is used to control harmful arthropods living in houses, the application amount is 1 / 2 m / day for surface treatment. 2 The amount of the compound of the present invention per square meter is usually 0.01 to 1,000 mg. 3 When the compound of the present invention or Composition A is formulated as an emulsifiable concentrate, wettable powder, flowable concentrate or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.1 to 10,000 ppm, whereas oil solutions, aerosols, fumigants, poison baits and the like are applied as they are.

[0073] When the compound of the present invention or Composition A is used to control ectoparasites in livestock such as cattle, horses, pigs, sheep, goats, and chickens, or small animals such as dogs, cats, rats, and mice, it can be administered to animals by methods known in veterinary medicine. Specific methods of administration include, for example, administration by tablet, incorporation into feed, suppository, or injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) for systemic control, and administration by methods such as spraying an oil or aqueous liquid, pour-on application, spot-on application, washing the animal with a shampoo formulation, or attaching a resin formulation to the animal as a collar or ear tag. When administered to animals, the amount of the compound of the present invention or Composition A is usually in the range of 0.1 to 1000 mg per kg of the animal's body weight.

[0074] The compound of the present invention or Composition A can be used as an agent for controlling harmful arthropods in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0075] Corn (horse-tooth, hard grain, soft grain, explosive, glutinous, sweet, field corn), rice (long grain, short grain, medium grain, japonica, tropical japonica, indica, javanica, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, glutinous rice), wheat (bread wheat (hard, soft, medium, red wheat, white wheat), durum wheat, spelt wheat, club wheat, each winter wheat type, spring wheat type), barley (two-row barley (= beer barley), six-row barley, naked barley, waxy barley, each winter barley type, spring barley type), rye (winter rye type, spring rye type), triticale (winter triticale type, spring triticale type), oats (winter oat type, spring oat type), sorghum, cotton (upland type, pima type), soybean (fully harvested seed varieties, edamame varieties, green-harvested varieties, indeterminate, determinate, semi-determinate types), peanuts, potato (tetraploid, diploid, true seed varieties), buckwheat, sugar beet (sugar production, animal feed, root vegetable, leafy vegetable, fuel), rapeseed (winter rapeseed type, spring rapeseed type), canola (winter canola type, spring canola type), sunflower (oil production, food, ornamental), sugarcane, tobacco, tea plant, mulberry, eggplant Vegetables from the Brassicaceae family (eggplant, tomato, bell pepper, chili pepper, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard greens, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, garland chrysanthemum, artichoke, lettuce, etc.), Liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), Apiaceae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), and ichi Goats, sweet potatoes, yams, taro, pome fruits (apples, European pears, Japanese pears, Chinese pears, quince, quince, etc.), stone fruits (peaches, plums, nectarines, plums, cherries, apricots, prunes, etc.), citrus fruits (Satsuma mandarins, oranges, lemons, limes, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, figs, olives, loquats, bananas, coffee, dates,Coconut palms, ornamental plants, forest plants, lawn grasses, pasture grasses, etc.

[0076] The above-mentioned plants are not particularly limited as long as they are varieties that are commonly cultivated, and include plants that can be produced by natural crossbreeding, plants that can be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of genetically modified crops include plants that have been conferred resistance to herbicides such as HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, bromoxynil, or dicamba; plants that are capable of synthesizing selective toxins known to be found in the genus Bacillus, such as Bacillus thuringiensis; and plants that can be conferred specific insecticidal activity by synthesizing gene fragments that partially match endogenous genes derived from harmful insects and inducing gene silencing (RNAi; RNA interference) in the target harmful insect.

[0077] The present invention will be explained in more detail below with reference to production examples, formulation examples, test examples, etc., but the present invention is not limited to these examples. First, production examples of the compounds of the present invention and their production intermediates will be shown. In this specification, Me represents a methyl group.

[0078] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] + or [M-H] - and 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.

[0079] [LC conditions] Column: L-column 2 ODS, inner diameter 4.6 mm, length 35 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 252 nm 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: Solution was delivered at the concentration gradient shown in [Table LC1].

[0080]

[0081] [MS conditions] Detector: LCMS-2020 (manufactured by Shimadzu Corporation) or LCMS-2050 (manufactured by Shimadzu Corporation) Ionization method: DUIS method (ESI, APCI)

[0082] Preparation Example 1: To a mixture of 2.0 g of tert-butyl (S)-[1-{1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl}ethyl]carbamate and 30 mL of chloroform, 8.6 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, stirred at room temperature for 16 hours, and then concentrated. 0.30 g of the resulting residue was mixed with 5.7 mL of acetonitrile, and 0.38 g of di(N-succinimidyl)carbonate and 0.37 mL of pyridine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 2.0 mL of water and 2.0 mL of acetonitrile, and 1.2 g of sodium carbonate and 0.19 g of 3-ethylthiazol-2(3H)-imine were added at room temperature and stirred for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 0.13 g of the present compound 1 represented by the following formula. Compound 1 of the present invention 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.77 (1H, d), 6.40 (1H, d), 6.30-6.25 (1H, m), 6.19 (1H, d), 4.08-4.01 (2H, m), 1.63 (3H, d), 1.35 (3H, t).

[0083] Production Example 1-2 In Production Example 1, the chemical compound and the physical properties of the chemical compound produced by the manufacturer are shown below. Compound 2 of this invention 1 H-NMR (CDCl3) δ: 8.89 (2H, t), 8.03 (1H, s), 7.37 (1H, t), 6.61 (1H, t), 6.45 (1H, d), 6.30-6.25 (1H, m), 3.83 (3H, s), 1.65 (3H, d).

[0084] This compound 3 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.03 (1H, s), 7.37 (1H, t), 6.62 (1H, t), 6.42 (1H, d), 6.30-6.24 (1H, m), 4.30-4.23 (2H, m), 1.65 (3H, d), 1.41 (3H, t).

[0085] Compound 4 of this invention 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.04 (1H, s), 7.38 (1H, t), 6.63 (1H, t), 6.52 (1H, d), 6.28-6.24 (1H, m), 6.21 (1H, tt), 4.64-4.50 (2H, m), 1.65 (3H, d).

[0086] This compound 5 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.03 (1H, s), 7.37 (1H, t), 6.63 (1H, t), 6.40 (1H, d), 6.29-6.24 (1H, m), 4.09-4.04 (2H, m), 1.65 (3H, d), 1.38-1.31 (1H, m), 0.60-0.57 (2H, m), 0.46-0.41 (2H, m).

[0087] Compound 6 of this invention 1H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.38 (1H, t), 6.65 (1H, t), 6.52 (1H, d), 6.29-6.24 (1H, m), 5.04-4.95 (2H, m), 2.41 (1H, s), 1.65 (3H, d).

[0088] Compound 7 of this invention 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.04 (1H, s), 7.38-7.33 (6H, m), 6.60 (1H, t), 6.47 (1H, d), 6.30-6.25 (1H, m), 5.42 (1H, d), 5.35 (1H, d), 1.65 (3H, d).

[0089] Compound 8 of this invention 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.38 (1H, t), 6.48 (1H, d), 6.29-6.24 (1H, m), 4.46 (2H, q), 1.65 (3H, d), 1.44 (3H, t).

[0090] Compound 9 of this invention 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.04 (1H, s), 7.38 (1H, t), 6.57 (1H, d), 6.38-6.08 (2H, m), 4.69-4.50 (2H, m), 1.65 (3H, d).

[0091] This compound 10 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.04 (1H, s), 7.39 (1H, t), 6.60 (1H, d), 6.38-6.08 (2H, m), 4.69-4.51 (2H, m), 1.65 (3H, d).

[0092] Compound 11 of this invention 1H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.38 (1H, t), 7.20 (1H, br s), 6.41 (1H, d), 6.28-5.97 (2H, m), 4.41-4.28 (2H, m), 1.64 (3H, d).

[0093] Compound 12 of this invention 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.02 (1H, s), 7.88 (1H, d), 7.47 (1H, d), 7.38-7.33 (2H, m), 6.55 (1H, d), 6.40-6.07 (2H, m), 4.38-4.19 (2H, m), 1.62 (3H, d).

[0094] This compound 13 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.02-7.99 (2H, m), 7.38-7.35 (2H, m), 7.29 (1H, dd), 6.77 (1H, d), 6.43-6.08 (2H, m), 4.44-4.21 (2H, m), 1.62 (3H, d).

[0095] This compound 14 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.07 (1H, d), 8.02 (1H, s), 7.36 (1H, t), 7.29 (1H, d), 7.21 (1H, dd), 6.38-6.08 (3H, m), 4.44-4.21 (2H, m), 1.62 (3H, d).

[0096] This compound 15 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.18-8.15 (1H, m), 8.02 (1H, s), 7.36 (1H, t), 7.24-7.20 (2H, m), 6.35-6.08 (3H, m), 4.40-4.24 (2H, m), 1.62 (3H, d).

[0097] This compound 16 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.99 (1H, d), 7.59 (1H, s), 7.38 (1H, t), 7.33-7.31 (1H, m), 6.35-6.14 (3H, m), 4.45-4.28 (2H, m), 1.64 (3H, d).

[0098] This compound 17 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.04-8.02 (2H, m), 7.36 (1H, t), 7.25-7.24 (1H, m), 6.36-6.16 (4H, m), 6.04 (1H, d), 4.44-4.27 (2H, m), 1.63 (3H, d).

[0099] The compound of this invention, 18 LCMS: 389 [M+H] + , RT=0.897 points (outputter: LCMS-2020)

[0100] This compound 19 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.03 (1H, s), 7.89 (1H, d), 7.36 (1H, t), 7.03 (1H, t), 6.55 (1H, d), 6.40-6.09 (3H, m), 4.85-4.74 (2H, m), 1.63 (3H, d).

[0101] This compound 20 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.89 (1H, d), 7.70 (1H, d), 7.38 (1H, t), 7.23 (1H, dd), 6.31-6.11 (3H, m), 4.44-4.27 (2H, m), 1.64 (3H, d).

[0102] Compound 21 of this invention1 H-NMR (CDCl3) δ: 8.90 (2H, d), 8.03 (1H, s), 7.86 (1H, dd), 7.37 (1H, t), 7.13 (1H, dd), 6.45-6.12 (4H, m), 4.83-4.66 (2H, m), 1.63 (3H, d).

[0103] Compound 22 of this invention 1 H-NMR (CDCl3) δ: 8.50 (1H, d), 7.95 (1H, s), 7.93-7.85 (2H, m), 6.62 (1H, t), 6.58 (1H, d), 6.19 (1H, tt), 6.16-6.11 (1H, m), 4.59-4.50 (2H, m), 1.65 (3H, d).

[0104] This compound 23 1 H-NMR (CDCl3) δ: 8.83 (2H, s), 8.04 (1H, s), 6.63 (1H, t), 6.45 (1H, d), 6.20 (1H, tt), 6.22-6.16 (1H, m), 4.60-4.53 (2H, m), 1.64 (3H, d).

[0105] This compound 24 1 H-NMR (CDCl3) δ: 8.54 (1H, ddd), 7.95 (1H, s), 7.93-7.89 (2H, m), 7.34-7.31 (1H, m), 6.62 (1H, t), 6.63-6.59 (1H, m), 6.20 (1H, tt), 6.24-6.18 (1H, m), 4.61-4.50 (2H, m), 1.65 (3H, d).

[0106] This compound 25 1H-NMR (CDCl3) δ: 8.75 (2H, s), 8.03 (1H, s), 6.63 (1H, t), 6.45 (1H, d), 6.20 (1H, tt), 6.19-6.14 (1H, m), 4.62-4.50 (2H, m), 1.64 (3H, d).

[0107] This compound 26 1 H-NMR (CDCl3) δ: 8.83 (1H, d), 8.16-8.14 (2H, m), 7.99 (1H, s), 6.62 (1H, t), 6.55 (1H, dd), 6.19 (1H, tt), 6.23-6.21 (1H, m), 4.60-4.50 (2H, m), 1.66 (3H, d).

[0108] This compound 27 1 H-NMR (CDCl3) δ: 7.96 (1H, s), 7.88 (1H, d), 7.13 (1H, d), 6.31-6.11 (2H, m), 5.75 (1H, dt), 4.64-4.52 (2H, m), 3.85 (3H, s), 1.67 (3H, d).

[0109] This compound 28 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.36 (1H, t), 6.36-6.22 (2H, m), 6.19 (1H, tt), 4.53-4.41 (2H, m), 2.08-2.06 (1H, m), 1.63 (3H, d), 1.10-1.09 (2H, m), 0.96-0.93 (2H, m).

[0110] Compound 29 of this invention, LCMS: 457 [M+H] + , RT=1.579 points (outputter: LCMS-2020)

[0111] This compound 30 1H-NMR (CDCl3) δ: 8.87 (2H, d), 7.33 (1H, t), 6.71-6.70 (1H, m), 6.62 (1H, t), 6.27-6.19 (1H, m), 6.20 (1H, tt), 4.57-4.51 (2H, m), 2.50 (3H, s), 1.64 (3H, d).

[0112] Compound 31 of the present invention 1 H-NMR (CDCl3) δ: 8.00-7.99 (2H, m), 7.20 (1H, d), 6.60 (1H, t), 6.48 (1H, d), 6.19 (1H, tt), 6.01-5.96 (1H, m), 4.59-4.47 (2H, m), 4.21 (3H, s), 1.75 (3H, d).

[0113] Compound 34 of the present invention 1 H-NMR (CDCl3) δ: 8.48 (1H, dd), 7.93 (1H, s), 7.89-7.84 (2H, m), 6.23-6.21 (1H, m), 6.16-6.10 (1H, m), 4.20-4.18 (2H, m), 2.76 (2H, q), 1.63 (3H, d), 1.37 (3H, t), 1.28 (3H, t).

[0114] Preparation Example 2: To a mixture of 0.1 g of the present compound 33 and 3 mL of acetonitrile, 0.54 g of potassium carbonate and 0.04 mL of methyl iodide were added and stirred at room temperature for 16 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate 100%) to obtain 0.04 g of the present compound 32 represented by the following formula. Compound 32 of the present invention 1 H-NMR (CDCl3) δ: 8.21 (1H, s), 7.94 (1H, s), 7.04 (1H, s), 6.77-6.46 (2H, m), 6.35-6.05 (2H, m), 4.61-4.51 (2H, m), 3.60 (3H, s), 1.61 (3H, d).

[0115] Preparation Example 3: To a mixture of 0.30 g of Intermediate 2-2 and 5.7 mL of acetonitrile, 0.35 g of di(N-succinimidyl) carbonate and 0.78 mL of diisopropylethylamine were added sequentially at room temperature and stirred for 1 hour. To the resulting reaction solution, 0.40 g of Intermediate 7 and 0.78 mL of diisopropylethylamine were added sequentially at room temperature and stirred for 3 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 0.10 g of the present invention compound 33 represented by the following formula. Compound 33 of the present invention LCMS: 448 [M+H] + , RT = 1.344 min (detector: LCMS-2020)

[0116] Preparation Example 4: To a mixture of 1.0 g of Intermediate 2-14 and 5 mL of chloroform, 3.4 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added. The mixture was stirred at room temperature for 16 hours and then concentrated. The resulting residue was mixed with 10 mL of acetonitrile, and 0.83 g of di(N-succinimidyl) carbonate and 1.9 mL of diisopropylethylamine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 2.0 mL of water and 4.0 mL of acetonitrile, and 1.4 g of sodium carbonate and 0.99 g of Intermediate 7 were added at room temperature. The mixture was stirred for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 0.12 g of the present invention compound 35 represented by the following formula. Compound 35 of the present invention 1 H-NMR (CDCl3) δ: 8.92 (2H, s), 8.03 (1H, s), 6.63 (1H, t), 6.45-6.43 (1H, m), 6.35-6.05 (2H, m), 4.60-4.53 (2H, m), 1.64 (3H, d).

[0117] Production Example 5 Compounds produced according to Production Example 4 and their physical properties are shown below. Compound 36 of the present invention 1H-NMR (CDCl3) δ: 8.78 (1H, dd), 8.10-8.06 (2H, m), 6.63 (1H, t), 6.54-6.52 (1H, m), 6.36-6.06 (2H, m), 4.62-4.52 (2H, m), 2.07-2.04 (1H, m), 1.61 (3H, d), 1.07-1.03 (4H, m).

[0118] This compound 37 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.36 (1H, t), 6.36-6.33 (1H, m), 6.27-6.24 (1H, m), 6.20 (1H, tt), 4.54-4.45 (2H, m), 2.78 (2H, q), 1.63 (3H, d), 1.29 (3H, t).

[0119] This compound 38 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.45 (1H, s), 6.26-6.22 (2H, m), 6.08 (1H, tt), 4.30-4.19 (2H, m), 2.18 (3H, d), 1.63 (3H, d).

[0120] This compound 39 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.45 (1H, s), 6.25-6.22 (2H, m), 6.09 (1H, tt), 4.29-4.21 (2H, m), 2.57-2.53 (2H, m), 1.63 (3H, d), 1.21 (3H, t).

[0121] This compound 40 1H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.42 (1H, s), 6.30-6.23 (1H, m), 6.18-6.17 (1H, m), 6.10 (1H, tt), 4.29-4.21 (2H, m), 2.88-2.84 (1H, m), 1.63 (3H, d), 1.23 (6H, d).

[0122] This compound 41 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.03 (1H, s), 7.36 (1H, t), 6.38-6.36 (1H, m), 6.28-6.22 (1H, m), 6.19 (1H, tt), 4.58-4.40 (2H, m), 2.44 (3H, s), 1.64 (3H, d).

[0123] This compound 42 1 H-NMR (CDCl3) δ: 7.96 (1H, s), 7.87 (1H, d), 7.13 (1H, d), 6.63 (1H, t), 6.47 (1H, d), 6.17 (1H, tt), 5.75 (1H, dt), 4.56-4.48 (2H, m), 3.85 (3H, s), 1.68 (3H, d).

[0124] This compound 43 1 H-NMR (CDCl3) δ: 7.96 (1H, s), 7.86 (1H, d), 7.12 (1H, d), 6.62 (1H, t), 6.47-6.44 (1H, m), 6.18 (1H, tt), 5.80-5.73 (1H, m), 4.58-4.48 (2H, m), 4.36-4.19 (2H, m), 1.68 (3H, d), 1.46 (3H, t).

[0125] This compound 44 1H-NMR (CDCl3) δ: 7.96 (1H, s), 7.86 (1H, d), 7.12 (1H, d), 6.38 (1H, d), 6.21 (1H, tt), 5.80-5.73 (1H, m), 4.62-4.53 (2H, m), 4.35-4.19 (2H, m), 1.67 (3H, d), 1.46 (3H, t).

[0126] Compound 45 of the present invention 1 H-NMR (CDCl3) δ: 9.04 (2H, s), 8.03 (1H, s), 6.62 (1H, t), 6.47-6.45 (1H, m), 6.35-6.05 (2H, m), 4.59-4.52 (2H, m), 1.63 (3H, d).

[0127] Production Example 6: To a mixture of 2.0 g of tert-butyl (S)-[1-{1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl}ethyl]carbamate and 30 mL of chloroform, 8.6 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, stirred at room temperature for 16 hours, and then concentrated. 0.15 g of the resulting residue was mixed with 0.46 mL of triethylamine and 2.0 mL of chloroform, and a mixture of 0.098 g of triphosgene and 2.0 mL of chloroform was added under ice-cooling, followed by stirring for 15 minutes under ice-cooling. To the resulting reaction solution, a mixture of 0.46 g of Intermediate 22, 0.37 mL of triethylamine, and 2.0 mL of chloroform was added under ice-cooling, followed by stirring at room temperature for 3 hours. A saturated aqueous solution of sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate) to obtain 0.042 g of the present compound 46 represented by the following formula. Compound 46 of the present invention 1H-NMR (CDCl3) δ: 8.90 (2H, d), 8.60 (1H, s), 8.03 (1H, s), 7.47 (1H, s), 7.37 (1H, t), 6.36-6.05 (3H, m), 4.42-4.19 (2H, m), 1.62 (3H, d).

[0128] Preparation Example 7: 17 mL of a methylamine / methanol solution (approximately 40%) was added to 1.1 g of Intermediate 3-3 at room temperature and stirred at 50°C for 3 hours. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure. The resulting residue was mixed with 5.0 mL of acetonitrile and filtered. 0.84 g of di(N-succinimidyl)carbonate and 1.8 mL of diisopropylethylamine were added to the filtrate at room temperature and stirred for 2 hours, followed by concentration. The resulting residue was mixed with 2.5 mL of water and 5.0 mL of acetonitrile, and 1.7 g of sodium carbonate and 1.2 g of Intermediate 7 were added at room temperature and stirred for 1.5 hours. Water was added to the resulting mixture, which was then extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.12 g of the present invention compound 47 represented by the following formula. Compound 47 of the present invention 1 H-NMR (CDCl3) δ: 8.86 (2H, d), 7.33 (1H, t), 6.62 (1H, t), 6.59-6.56 (1H, m), 6.36-6.06 (2H, m), 4.57-4.54 (2H, m), 2.50 (3H, s), 1.63 (3H, d).

[0129] Production Example 8 Compounds produced according to Production Example 7 and their physical properties are shown below. Compound 48 of the present invention 1 H-NMR (CDCl3) δ: 8.81 (2H, d), 7.22 (1H, t), 6.28 (1H, t), 6.60 (1H, d), 6.36-6.06 (2H, m), 4.65-4.47 (2H, m), 4.39-4.28 (1H, m), 3.06 (3H, d), 1.61 (3H, d).

[0130] Compound 49 of the present invention 1 H-NMR (CDCl3) δ: 8.87 (2H, d), 7.32 (1H, t), 6.62 (1H, t), 6.61-6.59 (1H, m), 6.36-6.06 (2H, m), 4.60-4.53 (2H, m), 2.85 (2H, q), 1.63 (3H, d), 1.39 (3H, t).

[0131] Compound 50 of the present invention 1 H-NMR (CDCl3) δ: 8.80 (2H, d), 7.52-7.52 (1H, m), 7.33 (1H, t), 6.62 (1H, s), 6.61-6.59 (1H, m), 6.23-6.20 (2H, m), 4.58-4.55 (2H, m), 1.66 (3H, d), 1.49 (9H, s).

[0132] Preparation Example 8-2 A compound prepared in accordance with Preparation Example 7 using Intermediate 3-14 instead of Intermediate 3-3 and its physical properties are shown below. Compound 51 of the present invention 1 H-NMR (CDCl3) δ: 8.94 (2H, d), 7.45 (1H, t), 7.19-7.18 (1H, m), 6.79-6.77 (1H, m), 6.62 (1H, t), 6.29-6.24 (1H, m), 6.21 (1H, tt), 4.59-4.50 (2H, m), 3.04 (3H, d), 1.68 (3H, d).

[0133] Preparation Example 9: 0.098 g of Intermediate 7-1 was mixed with 1.5 mL of acetonitrile, and 0.11 g of di(N-succinimidyl)carbonate and 0.23 mL of diisopropylethylamine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.0 mL of water and 1.0 mL of acetonitrile, and 0.23 g of sodium carbonate and 0.16 g of Intermediate 7 were added at room temperature. The mixture was stirred for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 0.043 g of the present invention compound 52 represented by the following formula. Compound 52 of the present invention 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 7.40 (1H, t), 6.63 (1H, t), 6.40-6.38 (1H, m), 6.28-6.22 (1H, m), 6.21 (1H, tt), 4.60-4.53 (2H, m), 1.66 (3H, d).

[0134] Production Example 10 Compounds produced according to Production Example 9 and their physical properties are shown below. Compound 53 of the present invention 1 H-NMR (CDCl3) δ: 8.85 (2H, d), 7.30 (1H, t), 6.63 (1H, t), 6.59-6.56 (1H, m), 6.37-6.06 (2H, m), 4.62-4.53 (2H, m), 2.21-2.14 (1H, m), 1.60 (3H, d), 1.10-1.09 (2H, m), 1.05-0.99 (2H, m).

[0135] Compound 54 of the present invention 1 H-NMR (CDCl3) δ: 8.87 (2H, d), 7.31 (1H, t), 6.65-6.63 (1H, m), 6.63 (1H, t), 6.37-6.07 (2H, m), 4.61-4.54 (2H, m), 3.23-3.16 (1H, m), 1.63 (3H, d), 1.41 (6H, d).

[0136] Compound 22 of the present invention 1 H-NMR (CDCl3) δ: 8.50 (1H, d), 7.95 (1H, s), 7.93-7.85 (2H, m), 6.62 (1H, t), 6.58 (1H, d), 6.19 (1H, tt), 6.16-6.11 (1H, m), 4.59-4.50 (2H, m), 1.65 (3H, d).

[0137] Production Example 11: To a mixture of 2.0 g of tert-butyl (S)-[1-{1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl}ethyl]carbamate and 30 mL of chloroform, 8.6 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, stirred at room temperature for 16 hours, and then concentrated. 0.50 g of the resulting residue was mixed with 4.4 mL of acetonitrile, and 0.62 g of di(N-succinimidyl)carbonate and 1.5 mL of diisopropylethylamine were added at room temperature and stirred for 1 hour. 1.5 mL of diisopropylethylamine and 0.87 g of Intermediate 23 were added to the resulting mixture at room temperature and stirred for 5 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:5) to obtain 0.19 g of the present compound 55 represented by the following formula. Compound 55 of the present invention 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.36 (1H, t), 6.36-6.33 (1H, m), 6.27-6.23 (1H, m), 6.20 (1H, tt), 4.55-4.43 (2H, m), 3.10-3.03 (1H, m), 1.63 (3H, d), 1.30 (6H, d).

[0138] Production Example 12 Compounds produced according to Production Example 11 and their physical properties are shown below. Compound 56 of the present invention 1H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.36 (1H, t), 6.35-6.34 (1H, m), 6.28-6.24 (1H, m), 6.21 (1H, tt), 4.55-4.43 (2H, m), 1.63 (3H, d), 1.33 (9H, s).

[0139] This compound 57 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.03 (1H, s), 7.37 (1H, t), 6.48-6.46 (1H, m), 6.29-6.23 (1H, m), 6.20 (1H, tt), 4.58-4.50 (2H, m), 3.59 (2H, q), 1.64 (3H, d).

[0140] This compound 58 1 H-NMR (CDCl3) δ: 9.19 (1H, d), 8.89 (1H, d), 7.99 (1H, s), 7.97 (1H, dd), 6.76-6.48 (2H, m), 6.37-6.06 (2H, m), 4.66-4.47 (2H, m), 1.68 (3H, d).

[0141] This compound 59 1 H-NMR (CDCl3) δ: 8.02 (1H, d), 8.00 (1H, d), 7.57 (1H, d), 6.60 (1H, t), 6.47 (1H, d), 6.19 (1H, tt), 6.07-6.02 (1H, m), 4.60-4.48 (2H, m), 2.81 (3H, s), 1.76 (3H, d).

[0142] This compound 60 1H-NMR (CDCl3) δ: 9.18 (1H, d), 8.07 (1H, s), 7.71 (1H, d), 6.62 (1H, t), 6.48 (1H, d), 6.31-6.09 (2H, m), 4.61-4.49 (2H, m), 1.49 (3H, d).

[0143] This compound 61 1 H-NMR (CDCl3) δ: 8.53 (1H, d), 8.32 (1H, d), 8.07-8.05 (1H, m), 8.05 (1H, s), 6.49 (1H, d), 6.32-6.13 (2H, m), 4.64-4.55 (2H, m), 3.14 (3H, d), 1.75 (3H, d).

[0144] This compound 62 1 H-NMR (CDCl3) δ: 8.54 (1H, d), 8.02 (1H, s), 6.77 (1H, d), 6.59 (1H, d), 6.38-6.08 (2H, m), 4.69-4.51 (2H, m), 4.16 (3H, s), 1.66 (3H, d).

[0145] This compound 63 1 H-NMR (CDCl3) δ: 9.32 (1H, s), 8.33 (1H, d), 8.03 (1H, s), 6.49 (1H, d), 6.38-6.08 (2H, m), 4.70-4.52 (2H, m), 1.68 (3H, d).

[0146] Preparation Example 13: 0.69 g of Intermediate 7 was mixed with 3.0 mL of acetonitrile, and 0.58 g of di(N-succinimidyl)carbonate and 1.4 mL of diisopropylethylamine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.5 mL of water and 3.0 mL of acetonitrile, and 1.0 g of sodium carbonate and 0.38 g of Intermediate 7-2 were added at room temperature. The mixture was stirred for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.16 g of the present invention compound 64 represented by the following formula. Compound 64 of the present invention 1 H-NMR (CDCl3) δ: 8.99 (2H, d), 8.72 (1H, d), 8.69 (1H, d), 7.41 (1H, t), 6.77-6.74 (1H, m), 6.61 (1H, t), 6.20 (1H, tt), 6.02-5.99 (1H, m), 4.57-4.53 (2H, m), 1.59 (3H, d).

[0147] Production Example 14 Compounds produced according to Production Example 13 and their physical properties are shown below. Compound 65 of the present invention 1 H-NMR (CDCl3) δ: 8.69 (1H, d), 8.56 (1H, d), 8.01 (2H, s), 6.68-6.66 (1H, m), 6.61 (1H, t), 6.20 (1H, tt), 5.99-5.96 (1H, m), 4.58-4.54 (2H, m), 1.56 (3H, d).

[0148] Compound 66 of the present invention 1 H-NMR (CDCl3) δ: 8.69 (1H, d), 8.47 (1H, d), 8.46 (1H, d), 7.90 (1H, d), 6.59 (1H, t), 6.42-6.40 (1H, m), 6.19 (1H, tt), 5.77-5.73 (1H, m), 4.55-4.53 (2H, m), 1.70 (3H, d).

[0149] Compound 67 of the present invention LCMS: 460 [M+H] + , RT = 1.63 min (detector: LCMS-2020)

[0150] Compound 68 of the present invention LCMS: 446 [M+H] + , RT = 1.57 min (detector: LCMS-2020)

[0151] Preparation Example 15: 1.1 g of Intermediate 7-3 was added to 15 mL of a methylamine / methanol solution (approximately 40%) at room temperature and stirred at 50°C for 1 hour. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure. The resulting residue was mixed with acetonitrile and filtered. The resulting filtrate was concentrated to obtain Mixture A. 1.0 g of Intermediate 7 was mixed with 5.0 mL of acetonitrile, and 0.72 g of di(N-succinimidyl)carbonate and 2.0 mL of diisopropylethylamine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 2.0 mL of water and 5.0 mL of acetonitrile, and Mixture A and 1.5 g of sodium carbonate were added at room temperature. The mixture was stirred for 1.5 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.33 g of the present invention compound 69 represented by the following formula. Compound 69 of the present invention 1 H-NMR (CDCl3) δ: 8.77 (1H, dd), 8.10 (1H, dd), 8.01 (1H, d), 6.62 (1H, t), 6.49-6.46 (1H, m), 6.28-6.12 (2H, m), 4.59-4.50 (2H, m), 4.05 (3H, s), 1.63 (3H, d).

[0152] Preparation Example 15-2: To a mixture of 2.0 g of Intermediate 3-12 and 20 mL of ethanol, 0.58 mL of hydrazine monohydrate was added at room temperature and stirred at 85°C for 7.5 hours. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure to obtain Mixture B. 0.50 g of Intermediate 7 was mixed with 5.0 mL of acetonitrile, and 0.43 g of di(N-succinimidyl)carbonate and 0.52 mL of pyridine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 2.2 mL of water and 2.2 mL of acetonitrile, and 0.35 g of Mixture B was added. 0.69 g of sodium carbonate was then added at room temperature and stirred for 7 hours. Water was added to the resulting mixture, which was then extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.23 g of the present invention compound 70 represented by the following formula. Compound 70 of the present invention 1 H-NMR (CDCl3) δ: 9.14 (1H, s), 8.84 (1H, d), 7.91 (1H, d), 6.67-6.56 (2H, m), 6.32-6.10 (2H, m), 4.61-4.48 (2H, m), 2.45 (3H, s), 1.66 (3H, d).

[0153] Preparation Example 16: 3.3 mL of a methylamine / methanol solution (approximately 40%) was added to 0.22 g of Intermediate 3-19 at room temperature and stirred at 50°C for 1 hour. The resulting mixture was allowed to cool to room temperature and concentrated under reduced pressure. The resulting residue was mixed with acetonitrile and filtered. The resulting filtrate was concentrated to obtain Mixture C. 0.22 g of Intermediate 7 was mixed with 3.0 mL of acetonitrile, and 0.16 g of di(N-succinimidyl)carbonate and 0.20 mL of pyridine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.0 mL of water and 3.0 mL of acetonitrile, and Mixture C and 0.33 g of sodium carbonate were added and stirred for 1.5 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.055 g of the present invention compound 71 represented by the following formula. Compound 71 of the present invention 1 H-NMR (CDCl3) δ: 8.86 (2H, d), 7.30 (1H, t), 6.63 (1H, t), 6.50-6.48 (1H, m), 6.36-6.05 (2H, m), 4.60-4.50 (2H, m), 4.13 (3H, s), 1.63 (3H, d).

[0154] Production Example 17 Compounds produced according to Production Example 16 and their physical properties are shown below. Compound 72 of the present invention 1 H-NMR (CDCl3) δ: 8.80-8.79 (1H, m), 8.12-8.08 (2H, m), 6.61 (1H, t), 6.60-6.58 (1H, m), 6.34-6.04 (2H, m), 4.59-4.49 (2H, m), 2.44 (3H, s), 1.64 (3H, d).

[0155] Compound 73 of the present invention 1H-NMR (CDCl3) δ: 8.88 (2H, d), 7.33 (1H, t), 6.63 (1H, t), 6.59-6.56 (1H, m), 6.36-6.06 (2H, m), 4.59-4.53 (2H, m), 2.71 (3H, s), 1.64 (3H, d).

[0156] This compound 74 1 H-NMR (CDCl3) δ: 8.80 (1H, d), 8.10-8.07 (2H, m), 6.61 (1H, t), 6.39-6.36 (1H, m), 6.21-6.17 (1H, m), 4.29-4.22 (2H, m), 2.44 (3H, s), 1.63 (3H, d), 1.41 (3H, t).

[0157] This compound 75 1 H-NMR (CDCl3) δ: 8.85 (2H, d), 7.31 (1H, t), 6.43-6.40 (1H, m), 6.35-6.05 (2H, m), 4.54-4.44 (2H, m), 2.83-2.75 (2H, m), 2.49 (3H, s), 1.62 (3H, d), 1.33-1.24 (3H, m).

[0158] This compound 76 1 H-NMR (CDCl3) δ: 8.84 (2H, d), 7.28 (1H, t), 6.42-6.40 (1H, m), 6.36-6.06 (2H, m), 4.54-4.48 (2H, m), 2.78 (2H, q), 2.19-2.15 (1H, m), 1.59 (3H, d), 1.30 (3H, t), 1.12-1.07 (2H, m), 1.02-0.99 (2H, m).

[0159] This compound 77 1H-NMR (CDCl3) δ: 8.45 (1H, d), 7.85 (1H, d), 7.81 (1H, dd), 6.71-6.53 (2H, m), 6.31-6.10 (1H, m), 6.09-6.05 (1H, m), 4.62-4.50 (2H, m), 2.08-2.03 (1H, m), 1.60 (3H, d), 1.07-0.98 (4H, m).

[0160] This compound 78 1 H-NMR (CDCl3) δ: 8.55 (1H, d), 7.95 (1H, dd), 7.80 (1H, d), 6.71-6.53 (2H, m), 6.20 (1H, tt), 6.09-6.05 (1H, m), 4.62-4.50 (2H, m), 2.08-2.03 (1H, m), 1.60 (3H, d), 1.07-0.98 (4H, m).

[0161] This compound 79 1 H-NMR (CDCl3) δ: 7.83 (1H, d), 7.08 (1H, d), 6.63 (1H, t), 6.35-6.04 (2H, m), 5.71-5.64 (1H, m), 4.60-4.51 (2H, m), 3.82 (3H, s), 2.08-2.01 (1H, m), 1.63 (3H, d), 1.02-0.99 (4H, m).

[0162] This compound 80 1 H-NMR (CDCl3) δ: 7.84 (1H, d), 7.10 (1H, d), 6.62 (1H, t), 6.37 (1H, d), 6.18 (1H, tt), 5.71-5.66 (1H, m), 4.59-4.47 (2H, m), 3.83 (3H, s), 2.42 (3H, s), 1.65 (3H, d).

[0163] Compound 81 of this invention 1H-NMR (CDCl3) δ: 8.23 ​​(1H, s), 6.78 (1H, t), 6.33 (2H, tt), 5.88 (1H, d), 5.38-5.30 (1H, m), 4.88-4.80 (2H, m), 2.84 (3H, s), 1.63 (3H, d).

[0164] Compound 82 of the present invention 1 H-NMR (CDCl3) δ: 8.23 ​​(2H, s), 6.77 (1H, t), 5.96 (1H, d), 5.39-5.31 (1H, m), 4.27-4.22 (2H, m), 2.86 (3H, s), 1.63 (3H, d), 1.55 (3H, t).

[0165] Compound 83 of the present invention 1 H-NMR (CDCl3) δ: 7.82 (1H, d), 7.08 (1H, d), 6.62 (1H, t), 6.15 (1H, d), 5.70-5.65 (1H, m), 4.29-4.22 (2H, m), 3.82 (3H, s), 2.05-2.01 (1H, m), 1.62 (3H, d), 1.41 (3H, t), 1.03-0.99 (4H, m).

[0166] Compound 84 of the present invention 1 H-NMR (CDCl3) δ: 8.78 (1H, d), 8.09 (1H, dd), 8.05 (1H, d), 6.62 (1H, t), 6.42 (1H, d), 6.20-6.13 (1H, m), 4.31-4.20 (2H, m), 2.09-2.03 (1H, m), 1.60 (3H, d), 1.42 (3H, t), 1.08-0.99 (4H, m).

[0167] Preparation Example 17-2 A compound prepared according to Preparation Example 16 using Intermediate 3-13 instead of Intermediate 3-19 and its physical properties are shown below. Compound 85 of the present invention 1H-NMR (CDCl3) δ: 7.90 (1H, s), 6.67-6.57 (2H, m), 6.25-6.14 (3H, m), 4.60-4.50 (2H, m), 3.01-3.00 (3H, m), 2.42 (3H, s), 1.62 (3H, d).

[0168] Production Example 18: To a mixture of 2.0 g of tert-butyl (S)-[1-{1-(pyrimidin-2-yl)-1H-1,2,4-triazol-5-yl}ethyl]carbamate and 30 mL of chloroform, 8.6 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, and the mixture was stirred at room temperature for 16 hours and then concentrated to obtain mixture D. 0.60 g of intermediate 27 was mixed with 5.5 mL of acetonitrile, and 0.42 g of di(N-succinimidyl)carbonate and 0.53 mL of pyridine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.3 mL of water and 2.7 mL of acetonitrile, and 0.37 g of mixture D and 0.87 g of sodium carbonate were added at room temperature and stirred for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 0.050 g of the present compound 86 represented by the following formula. Compound 86 of the present invention 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.02 (1H, s), 7.37-7.36 (2H, m), 6.34-6.04 (3H, m), 4.07-3.97 (2H, m), 1.63 (3H, d).

[0169] Production Example 19 Compounds produced according to Production Example 18 and their physical properties are shown below. Compound 87 of the present invention 1 H-NMR (CDCl3) δ: 8.89 (2H, d), 8.15 (1H, s), 8.03 (1H, s), 7.37 (1H, t), 6.45-6.43 (1H, m), 6.29-6.23 (1H, m), 6.22 (1H, tt), 4.66-4.50 (2H, m), 1.64 (3H, d).

[0170] This compound 88 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.11 (1H, s), 8.03 (1H, s), 7.35 (1H, t), 6.35-6.33 (1H, m), 6.30-6.23 (1H, m), 4.28 (2H, q), 1.64 (3H, d), 1.40 (3H, t).

[0171] This compound 89 1 H-NMR (CDCl3) δ: 8.87 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.26-6.24 (2H, m), 4.17 (2H, q), 2.08-2.04 (1H, m), 1.62 (3H, d), 1.36 (3H, t), 1.09-1.04 (2H, m), 0.93-0.91 (2H, m).

[0172] This compound 90 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.36 (1H, t), 6.35-6.33 (1H, m), 6.27-6.24 (1H, m), 6.20 (1H, tt), 4.59-4.40 (2H, m), 2.72 (2H, t), 1.73-1.70 (2H, m), 1.63 (3H, d), 0.98 (3H, t).

[0173] This compound 91 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.26-6.24 (2H, m), 4.22-4.17 (2H, m), 2.43 (3H, s), 1.63 (3H, d), 1.37 (3H, t).

[0174] This compound 92 1H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.27-6.25 (2H, m), 4.22-4.18 (2H, m), 2.77 (2H, q), 1.65-1.63 (3H, m), 1.37 (3H, t), 1.28 (3H, t).

[0175] This compound 93 1 H-NMR (CDCl3) δ: 8.88 (2H, d), 8.02 (1H, s), 7.35 (1H, t), 6.32-6.23 (2H, m), 3.75 (3H, s), 2.43 (3H, s), 1.63 (3H, d).

[0176] This compound 94 1 H-NMR (CDCl3) δ: 8.82-8.82 (1H, m), 8.15-8.12 (2H, m), 7.98 (1H, s), 6.33-6.32 (1H, m), 6.26-6.04 (2H, m), 4.55-4.43 (2H, m), 2.77 (2H, q), 1.64 (3H, d), 1.29 (3H, t).

[0177] This compound 95 1 H-NMR (CDCl3) δ: 8.48 (1H, dd), 7.94 (1H, s), 7.90-7.85 (2H, m), 6.41-6.39 (1H, m), 6.19 (1H, tt), 6.14-6.11 (1H, m), 4.52-4.44 (2H, m), 2.77 (2H, q), 1.63 (3H, d), 1.29 (3H, t).

[0178] This compound 96 1H-NMR (CDCl3) δ: 8.02 (1H, s), 7.88-7.86 (2H, m), 7.83-7.81 (2H, m), 6.63 (1H, t), 6.42-6.40 (1H, m), 6.15 (1H, tt), 5.35-5.31 (1H, m), 4.52-4.49 (2H, m), 1.55 (3H, d).

[0179] This compound 97 1 H-NMR (CDCl3) δ: 8.76 (2H, s), 8.03 (1H, s), 6.67 (1H, t), 6.63 (1H, t), 6.48-6.45 (1H, m), 6.35-6.05 (2H, m), 4.59-4.53 (2H, m), 1.65 (3H, d).

[0180] This compound 98 1 H-NMR (CDCl3) δ: 7.98 (1H, s), 7.58-7.56 (2H, m), 7.25-7.23 (2H, m), 6.62 (1H, t), 6.53-6.51 (1H, m), 6.31-6.00 (1H, m), 5.29-5.22 (1H, m), 4.56-4.46 (2H, m), 1.51-1.49 (3H, m).

[0181] This compound 99 1 H-NMR (CDCl3) δ: 7.99 (1H, s), 7.58-7.48 (5H, m), 6.76-6.43 (2H, m), 6.32-6.01 (1H, m), 5.34-5.30 (1H, m), 4.56-4.46 (2H, m), 1.51-1.48 (3H, m).

[0182] This compound 100 1H-NMR (CDCl3) δ: 8.01 (1H, s), 7.94-7.89 (2H, m), 7.81-7.79 (1H, m), 7.71-7.68 (1H, m), 6.64 (1H, t), 6.32-6.02 (2H, m), 5.29-5.25 (1H, m), 4.55-4.52 (2H, m), 1.55 (3H, d).

[0183] Compound 101 of this invention, LCMS: 503 [M+H] + , RT=1.65 points (outputter: LCMS-2050)

[0184] This compound 102 1 H-NMR (CDCl3) δ: 8.78 (1H, d), 8.56 (1H, d), 8.34-8.31 (1H, m), 7.97 (1H, s), 6.62 (1H, t), 6.57-6.55 (1H, m), 6.34-6.32 (1H, m), 6.21 (1H, tt), 4.60-4.53 (2H, m), 3.89 (3H, s), 1.65 (3H, d).

[0185] This compound 103 1 H-NMR (DMSO-D6) δ: 11.55 (1H, s), 8.90 (1H, d), 8.56 (1H, d), 8.40-8.38 (1H, m), 8.18 (1H, s), 7.26 (1H, t), 6.49 (1H, tt), 6.03-5.96 (1H, m), 4.69-4.66 (2H, m), 2.10-2.07 (1H, m), 1.52 (3H, d), 0.92-0.91 (4H, m).

[0186] This compound 104 1H-NMR (DMSO-D6) δ: 11.22 (1H, s), 8.88 (1H, s), 8.55 (1H, s), 8.39-8.37 (1H, m), 8.18 (1H, s), 7.25 (1H, t), 6.48 (1H, tt), 5.99-5.97 (1H, m), 4.68-4.64 (2H, m), 2.17 (3H, s), 1.50 (3H, d).

[0187] This compound 105 1 H-NMR (CDCl3) δ: 8.24 (1H, s), 7.94 (1H, s), 6.62 (1H, t), 6.47-6.45 (1H, m), 6.20 (1H, tt), 6.16-6.14 (1H, m), 4.58-4.55 (2H, m), 3.95 (3H, s), 1.65 (3H, d).

[0188] This compound 106 1 H-NMR (CDCl3) δ: 8.50 (1H, d), 7.95 (1H, s), 7.91 (1H, d), 7.87 (1H, dd), 6.71-6.53 (2H, m), 6.30-6.10 (2H, m), 4.62-4.49 (2H, m), 1.64 (3H, d).

[0189] This compound 107 1 H-NMR (CDCl3) δ: 8.60 (1H, d), 8.01 (1H, dd), 7.95 (1H, s), 7.86 (1H, d), 6.71-6.50 (2H, m), 6.30-6.10 (2H, m), 4.62-4.49 (2H, m), 1.64 (3H, d).

[0190] This compound 108 1H-NMR (CDCl3) δ: 8.46 (1H, d), 7.86 (1H, d), 7.83 (1H, dd), 6.70-6.52 (2H, m), 6.29-6.07 (2H, m), 4.59-4.47 (2H, m), 2.43 (3H, s), 1.63 (3H, d).

[0191] Preparation Example 20: To a mixture of 0.25 g of Intermediate 7-4 and 2.6 mL of chloroform, 1.6 mL of trifluoroacetic acid was added and stirred at room temperature for 2 hours. The resulting mixture was concentrated to obtain Mixture E. 0.28 g of Intermediate 7 was mixed with 2.6 mL of acetonitrile, and 0.20 g of di(N-succinimidyl)carbonate and 0.25 mL of pyridine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.0 mL of water and 2.0 mL of acetonitrile, and Mixture E and 0.41 g of sodium carbonate were added at room temperature. The mixture was stirred for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:3) to obtain 0.10 g of the present invention compound 109 represented by the following formula: Compound 109 of the present invention 1 H-NMR (CDCl3) δ: 8.14 (1H, s), 7.95 (1H, s), 6.63 (1H, t), 6.37-6.34 (1H, m), 6.20 (1H, tt), 6.12-6.08 (1H, m), 4.60-4.54 (2H, m), 1.65 (3H, d).

[0192] Preparation Example 20-2: To a mixture of 2.6 g of Intermediate 7-10 and 30 mL of chloroform, 8.4 mL of trifluoroacetic acid was added at 0°C, the mixture was warmed to room temperature, and stirred for 2 hours. The resulting mixture was concentrated, and the resulting residue was mixed with 10 mL of acetonitrile. 2.6 g of di(N-succinimidyl) carbonate and 14 mL of diisopropylethylamine were added at room temperature, and the mixture was stirred for 45 minutes. 1.9 g of Intermediate 21 was added to the resulting mixture at room temperature, and the mixture was stirred for 12 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.70 g of the present invention compound 110 represented by the following formula: Compound 110 of the present invention 1 H-NMR (CDCl3) δ: 9.25 (1H, d), 8.31 (1H, d), 8.01 (1H, s), 6.31-6.08 (3H, m), 4.52-4.40 (2H, m), 2.09-2.06 (1H, m), 1.64 (3H, d), 1.11-1.08 (2H, m), 0.96-0.93 (2H, m).

[0193] Preparation Example 20-3 Compounds prepared according to Preparation Example 20-2 and their physical properties are shown below. Compound 111 of the present invention 1 H-NMR (CDCl3) δ: 9.27 (1H, s), 8.33 (1H, s), 8.03 (1H, s), 6.46 (1H, d), 6.33-6.13 (2H, m), 4.68-4.54 (2H, m), 1.67 (3H, d).

[0194] Compound 112 of the present invention 1 H-NMR (CDCl3) δ: 8.00 (1H, d), 7.99 (1H, s), 7.20 (1H, d), 6.46 (1H, d), 6.22 (1H, tt), 6.00 (1H, dt), 4.63-4.51 (2H, m), 4.21 (3H, s), 1.74 (3H, d).

[0195] Compound 113 of the present invention 1H-NMR (CDCl3) δ: 9.31 (1H, d), 8.63 (1H, d), 8.51 (1H, dd), 8.01 (1H, s), 6.62 (1H, t), 6.54 (1H, d), 6.19 (1H, tt), 6.17-6.10 (1H, m), 4.64-4.46 (2H, m), 1.66 (3H, d).

[0196] Compound 114 of the present invention 1 H-NMR (CDCl3) δ: 8.78 (1H, d), 7.97 (1H, s), 7.45 (1H, d), 6.63 (1H, t), 6.48 (1H, d), 6.34-6.11 (2H, m), 5.17-5.04 (1H, m), 4.94-4.82 (2H, m), 4.64-4.50 (2H, m), 1.65 (3H, d).

[0197] Compound 29 of the present invention 1 H-NMR (CDCl3) δ: 9.27 (1H, s), 8.33 (1H, s), 8.03 (1H, s), 6.74-6.54 (2H, m), 6.30 (2H, m), 4.64-4.50 (2H, m), 1.66 (3H, d).

[0198] Production Example 21: To a mixture of 0.10 g of the present invention compound 50 and 5.0 mL of chloroform, 1.0 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, and the mixture was stirred at room temperature for 5 hours and then concentrated. A saturated aqueous solution of sodium bicarbonate was added to the resulting residue, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:methanol=9:1) to obtain 0.05 g of the present invention compound 115 represented by the following formula. Compound 115 of the present invention 1H-NMR (CDCl3) δ: 8.87 (2H, d), 7.36 (1H, t), 6.85-6.83 (1H, m), 6.61 (1H, t), 6.36-6.06 (2H, m), 4.56-4.52 (2H, m), 1.68 (3H, d).

[0199] Preparation Example 22: To a mixture of 0.15 g of Intermediate 6-1 and 3.0 mL of dimethylformamide, 0.089 g of ethyl iodide and 0.079 g of potassium carbonate were added at room temperature, and the mixture was stirred at room temperature for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.14 g of the present invention compound 116 represented by the following formula. Compound 116 of the present invention 1 H-NMR (CDCl3) δ: 8.85 (2H, d), 7.29 (1H, t), 6.62 (1H, t), 6.48-6.46 (1H, m), 6.21-6.19 (1H, m), 4.27 (2H, q), 2.18-2.16 (1H, m), 1.60 (3H, d), 1.42 (3H, t), 1.12-0.98 (4H, m).

[0200] Preparation Example 22-2 Compounds prepared according to Preparation Example 22, using Intermediate 6-2 instead of Intermediate 6-1 and iodinated acetonitrile instead of ethyl iodide, and their physical properties are shown below. Compound 122 of the present invention 1 H-NMR (CDCl3) δ: 8.91 (2H, d), 8.06 (1H, s), 7.39 (1H, t), 6.96-6.94 (1H, m), 6.62 (1H, t), 6.28-6.23 (1H, m), 5.04 (2H, dd), 1.68 (3H, d).

[0201] Preparation Example 23: To a mixture of 0.31 g of the present invention compound 115 and 5.0 mL of THF, 0.30 mL of triethylamine and 0.68 mL of acetic anhydride were added at room temperature, and the mixture was stirred at room temperature for 24 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:9) to obtain 0.16 g of the present invention compound 117 represented by the following formula. Compound 117 of the present invention 1 H-NMR (CDCl3) δ: 8.90 (2H, d), 7.41 (1H, t), 6.63 (1H, t), 6.37-6.35 (1H, m), 6.31-6.26 (1H, m), 6.20 (1H, tt), 4.63-4.52 (2H, m), 2.35 (6H, s), 1.71 (3H, d).

[0202] Preparation Example 24: To 0.15 g of the present compound 105 and 3.0 mL of methanol, 0.30 mL of a methylamine / methanol solution (about 40%) was added at room temperature, and the mixture was heated to 50° C. and stirred for 4 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (hexane:ethyl acetate=3:7) to obtain 0.052 g of the present compound 118 represented by the following formula. Compound 118 of the present invention 1 H-NMR (CDCl3) δ: 7.93 (1H, s), 7.93 (1H, s), 6.63 (1H, t), 6.51-6.49 (1H, m), 6.35-6.05 (3H, m), 4.60-4.53 (2H, m), 3.04-3.01 (3H, m), 1.64 (3H, d).

[0203] Production Example 25: 5.0 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added to 0.19 g of the present compound 29, and the mixture was stirred at room temperature for 4 hours. The resulting mixture was concentrated, neutralized with saturated aqueous sodium bicarbonate, and then extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=2:8) to obtain 0.05 g of the present compound 119 represented by the following formula. Compound 119 of the present invention 1 H-NMR (CDCl3) δ: 9.19 (1H, d), 8.75 (1H, d), 8.02 (1H, s), 7.78 (1H, s), 6.63 (1H, t), 6.47 (1H, d), 6.36-6.33 (1H, m), 6.21 (1H, tt), 5.74 (1H, s), 4.62-4.50 (2H, m), 1.67 (3H, d).

[0204] Preparation Example 26 A compound prepared according to Preparation Example 25 using present invention compound 110 instead of present invention compound 29 and its physical properties are shown below. Compound 120 of the present invention 1 H-NMR (CDCl3) δ: 9.16 (1H, d), 8.73 (1H, d), 8.00 (1H, s), 7.77 (1H, br s), 6.33-6.08 (3H, m), 5.73 (1H, br s), 4.55-4.39 (2H, m), 2.08-2.05 (1H, m), 1.64 (3H, d), 1.11-1.07 (2H, m), 0.96-0.93 (2H, m).

[0205] Preparation Example 26-2 A compound prepared according to Preparation Example 25 using present invention compound 111 instead of present invention compound 29 and its physical properties are shown below. Compound 121 of the present invention 1H-NMR (CDCl3) δ: 9.19 (1H, s), 8.75 (1H, s), 8.02 (1H, s), 7.78 (1H, br s), 6.53 (1H, d), 6.35-6.13 (2H, m), 5.74 (1H, br s), 4.67-4.53 (2H, m), 1.67 (3H, d).

[0206] Reference Production Example 1 To a mixture of 1.0 g of 2-amino-5-difluoromethyl-1,3,4-thiadiazole and 5 mL of dimethylformamide, 0.62 mL of methyl iodide was added at room temperature, and the mixture was stirred at room temperature for 14.5 hours and then at 50°C for 9 hours. The resulting mixture was concentrated, and tert-butyl methyl ether was added to the resulting residue. The precipitated solid was filtered using a Kiriyama funnel and washed with tert-butyl methyl ether. The resulting solid was dried to obtain 2.0 g of Intermediate 1 represented by the following formula: Intermediate 1 1 H-NMR (DMSO-D6) δ: 8.35 (1H, t), 4.81 (3H, s).

[0207] Reference Production Example 2 A compound prepared in accordance with Reference Production Example 1, except that ethyl iodide was used instead of methyl iodide, and its physical properties are shown below. Intermediate 2 1 H-NMR (DMSO-D6) δ: 10.12 (2H, s), 7.38 (1H, t), 4.21 (2H, q), 1.36 (3H, t).

[0208] Reference Production Example 2-2 A compound prepared in accordance with Reference Production Example 1, using cyclopropylmethyl iodide instead of methyl iodide, and its physical properties are shown below. Intermediate 3 LCMS: 206 [M+H] + , RT = 0.468 min (detector: LCMS-2020)

[0209] Reference Production Example 2-3 Compounds prepared in accordance with Reference Production Example 1, except that propargyl bromide was used instead of methyl iodide, and their physical properties are shown below. Intermediate 4 LCMS: 190 [M+H] +, RT = 0.319 min (detector: LCMS-2020)

[0210] Reference Production Example 2-4 Compounds prepared in accordance with Reference Production Example 1, except that benzyl bromide was used instead of methyl iodide, and their physical properties are shown below. Intermediate 5 LCMS: 242 [M+H] + , RT = 0.887 min (detector: LCMS-2020)

[0211] Reference Production Example 2-5 A compound prepared in accordance with Reference Production Example 1, except for using ethyl iodide instead of methyl iodide and 2-amino-5-trifluoromethyl-1,3,4-thiadiazole instead of 2-amino-5-difluoromethyl-1,3,4-thiadiazole, and its physical properties are shown below. Intermediate 6 LCMS: 198 [M+H] + , RT = 0.512 min (detector: LCMS-2020)

[0212] Reference Production Example 3: 5 mL of 2,2-difluoroethyl triflate was added to 2.0 g of 2-amino-5-difluoromethyl-1,3,4-thiadiazole at room temperature, and the mixture was stirred at 100°C for 8.5 hours. The resulting mixture was concentrated, and chloroform was added and the mixture was concentrated again. To the resulting residue was added tert-butyl methyl ether, and the precipitated solid was filtered using a Kiriyama funnel and washed with tert-butyl methyl ether. The resulting solid was dried to obtain 3.5 g of intermediate 7 represented by the following formula: Intermediate 7 1 H-NMR (DMSO-D6) δ: 7.34 (1H, t), 6.47 (1H, t), 4.79-4.69 (2H, m). 1 H-NMR (CD3CN) δ: 8.64 (2H, s), 6.98 (1H, t), 6.32 (1H, tt), 4.67 (2H, td).

[0213] Reference Production Example 4 Compounds prepared according to Reference Production Example 3 and their physical properties are shown below. Intermediate 8 1H-NMR (DMSO-D6) δ: 7.25-7.15 (1H, m), 6.46 (1H, tt), 4.74 (2H, td).

[0214] Intermediate 9 1 H-NMR (DMSO-D6) δ: 6.47 (1H, td), 4.79 (2H, td).

[0215] Intermediate 10 1 H-NMR (DMSO-D6) δ: 10.46 (1H, s), 8.35 (1H, s), 6.47 (1H, tt), 4.59 (2H, td).

[0216] Intermediate 11 1 H-NMR (DMSO-D6) δ: 8.89 (2H, s), 8.38 (1H, d), 8.09 (1H, dd), 6.90 (1H, d), 6.50 (1H, tt), 4.69 (2H, td).

[0217] Intermediate 12 1 H-NMR (DMSO-D6) δ: 8.97 (2H, s), 8.41 (1H, s), 8.07-8.05 (1H, m), 7.03 (1H, d), 6.65-6.38 (1H, m), 4.74-4.67 (2H, m).

[0218] Intermediate 13 1 H-NMR (DMSO-D6) δ: 8.99 (2H, s), 8.38 (1H, d), 8.01 (1H, dd), 7.10 (1H, d), 6.52 (1H, tt), 4.71 (2H, td).

[0219] Intermediate 14 1 H-NMR (DMSO-D6) δ: 8.81 (2H, s), 8.38-8.36 (1H, m), 8.12-8.06 (1H, m), 7.12 (1H, dd), 6.52 (1H, tt), 4.70 (2H, td).

[0220] Intermediate 15 1 H-NMR (DMSO-D6) δ: 9.65 (1H, s), 9.20 (1H, s), 8.73 (1H, s), 8.18 (1H, dd), 7.21 (1H, d), 6.54 (1H, tt), 4.81 (2H, td).

[0221] Intermediate 16 1 H-NMR (DMSO-D6) δ: 8.73 (2H, s), 8.00 (1H, d), 7.94-7.89 (1H, m), 7.07 (1H, d), 6.94 (1H, td), 6.52 (1H, tt), 4.76 (2H, td).

[0222] Intermediate 17 1 H-NMR (DMSO-D6) δ: 8.57 (2H, s), 7.85 (1H, s), 7.81 (1H, dd), 7.02 (1H, d), 6.51 (1H, tt), 4.69 (2H, td), 2.16 (3H, s).

[0223] Intermediate 18 1 H-NMR (DMSO-D6) δ: 9.10 (2H, s), 7.73 (1H, dd), 7.37 (1H, dd), 7.07 (1H, dd), 6.52 (1H, tt), 4.95 (2H, td).

[0224] Intermediate 19 1 H-NMR (DMSO-D6) δ: 9.82 (1H, s), 9.33 (1H, s), 8.88 (1H, d), 8.15 (1H, dd), 7.14 (1H, d), 6.53 (1H, tt), 4.74 (2H, td).

[0225] Intermediate 20 1H-NMR (DMSO-D6) δ: 9.13 (1H, s), 7.85 (1H, dd), 7.22 (1H, dd), 7.06 (1H, dd), 6.52 (1H, tt), 4.95-4.87 (2H, m).

[0226] Intermediate 21 LCMS: 206 [M+H] + , RT=0.604 points (outputter: LCMS-2020) 1 H-NMR (DMSO-D6) δ: 10.01 (2H, s), 6.45 (1H, tt), 4.65 (2H, td), 2.40-2.38 (1H, m), 1.22-1.17 (2H, m), 1.02-1.00 (2H, m).

[0227] Intermediate 22 1 H-NMR (DMSO-D6) δ: 9.01 (2H, s), 8.57 (1H, s), 7.49 (1H, s), 6.49 (1H, tt), 4.69 (2H, td).

[0228] Intermediate 23 1 H-NMR (DMSO-D6) δ: 10.08 (2H, s), 6.46 (1H, tt), 4.69 (2H, td), 3.28-3.24 (1H, m), 1.29 (6H, d).

[0229] Intermediate 24 1 H-NMR (DMSO-D6) δ: 10.15 (2H, s), 6.47 (1H, tt), 4.70 (2H, td), 1.35 (9H, s).

[0230] Intermediate 25 1 H-NMR (DMSO-D6) δ: 10.04 (2H, s), 6.46 (1H, tt), 4.69 (2H, td), 2.91 (2H, q), 1.24 (3H, t).

[0231] Intermediate 26 1H-NMR (CDCl3) δ: 6.14 (1H, tt), 4.28 (2H, td), 3.44 (2H, q).

[0232] Intermediate 27 1 H-NMR (DMSO-D6) δ: 10.50 (2H, s), 8.85-8.85 (1H, m), 6.39 (1H, tt), 4.40 (2H, td).

[0233] Intermediate 28 1 H-NMR (DMSO-D6) δ: 9.64 (2H, s), 7.11 (1H, d), 6.41 (1H, tt), 4.51-4.48 (2H, m), 2.22 (3H, d).

[0234] Intermediate 29 1 H-NMR (DMSO-D6) δ: 9.67 (2H, s), 7.14 (1H, s), 6.42 (1H, tt), 4.51-4.48 (2H, m), 2.63-2.59 (2H, m), 1.15 (3H, t).

[0235] Intermediate 30 1 H-NMR (DMSO-D6) δ: 9.71 (2H, s), 7.19 (1H, s), 6.45 (1H, tt), 4.53-4.51 (2H, m), 3.02-2.99 (1H, m), 1.21 (6H, d).

[0236] Intermediate 31 1 H-NMR (CDCl3) δ: 6.14 (2H, tt), 4.35-4.27 (2H, m), 2.35 (3H, s).

[0237] Intermediate 32 1 H-NMR (DMSO-D6) δ: 10.03 (2H, s), 8.99 (1H, s), 6.54 (1H, tt), 4.99 (2H, td).

[0238] Intermediate 331 H-NMR (CDCl3) δ: 6.14 (1H, tt), 4.27 (2H, td), 2.59 (2H, t), 1.68-1.65 (2H, m), 0.99 (3H, t).

[0239] Intermediate 34 1 H-NMR (CDCl3) δ: 9.33 (2H, s), 6.74 (1H, t), 4.34 (2H, q), 1.53 (3H, t).

[0240] Intermediate 35 1 H-NMR (DMSO-D6) δ: 9.82 (2H, s), 4.16 (2H, q), 2.90 (2H, q), 1.33 (3H, t), 1.24 (3H, t).

[0241] Intermediate 36 1 H-NMR (DMSO-D6) δ: 9.69 (2H, s), 8.94 (1H, s), 4.38 (2H, q), 1.44 (3H, t).

[0242] Intermediate 37 1 H-NMR (DMSO-D6) δ: 9.64 (2H, s), 4.09 (2H, q), 2.38-2.34 (1H, m), 1.31 (3H, t), 1.21-1.13 (2H, m), 1.02-0.97 (2H, m).

[0243] Intermediate 38 1 H-NMR (DMSO-D6) δ: 9.62 (2H, s), 4.12 (2H, q), 2.54 (3H, s), 1.32 (3H, t).

[0244] Reference Preparation Example 5 A mixture of 5.0 g of N-(tert-butoxycarbonyl)alaninamide, 8.9 mL of N,N-dimethylformamide dimethyl acetal, and 40 mL of chloroform was heated to 100°C and stirred for 5 hours. The resulting reaction solution was cooled to room temperature and then concentrated. 2.0 g of the resulting residue was mixed with 1,4-dioxane, and 1.0 g of 2-hydrazinopyridine and 4 mL of acetic acid were added, followed by stirring at 60°C for 5 hours. Aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=8:2) to obtain 1.0 g of intermediate 2-1 represented by the following formula: Intermediate 2-1 1 H-NMR (CDCl3) δ: 8.51 (1H), 7.93 (1H, s), 7.90-7.88 (2H, m), 7.32-7.29 (1H, m), 5.94-5.90 (1H, m), 5.68-5.65 (1H, m), 1.57 (3H, d), 1.42 (9H, s).

[0245] Reference Production Example 6-1 Compounds prepared according to Reference Production Example 5 and their physical properties are shown below. Intermediate 2-2 1 H-NMR (CDCl3) δ: 8.93 (1H, s), 8.01 (1H, s), 7.98 (1H, s), 6.07-6.02 (1H, m), 5.56-5.51 (1H, m), 1.57 (3H, d), 1.43 (9H, s).

[0246] Intermediate 2-3 LCMS: 325 / 327 (3:1) [M+H] + , RT = 1.50 min (detector: LCMS-2020)

[0247] Intermediate 2-4 LCMS: 309 [M+H] + , RT = 1.38 min (detector: LCMS-2020)

[0248] Intermediate 2-5 1H-NMR (DMSO-D6) δ: 9.04 (1H, s), 8.56 (1H, dd), 8.20 (1H, s), 8.04 (1H, d), 7.51 (1H, d), 5.65-5.58 (1H, m), 1.41 (3H, d), 1.29 (9H, s).

[0249] Intermediate 2-9 1 H-NMR (CDCl3) δ: 9.29 (1H, d), 8.61 (1H, d), 8.48 (1H, dd), 8.00 (1H, s), 5.91-5.84 (1H, m), 5.57 (1H, d), 1.57 (3H, d), 1.41 (9H, s).

[0250] Intermediate 2-10 1 H-NMR (CDCl3) δ: 8.74 (1H, s), 7.95 (1H, s), 7.43 (1H, s), 6.09-6.04 (1H, m), 5.59 (1H, d), 5.17-5.03 (1H, m), 4.93-4.81 (2H, m), 1.56 (3H, d), 1.43 (9H, s).

[0251] Intermediate 2-11 1 H-NMR (CDCl3) δ: 9.15 (1H, d), 8.87 (1H, d), 7.97 (1H, s), 7.95 (1H, dd), 6.11-6.04 (1H, m), 5.59 (1H, d), 1.59 (3H, d), 1.43 (9H, s).

[0252] Intermediate 2-12 1 H-NMR (CDCl3) δ: 8.01-7.99 (2H, m), 7.55 (1H, d), 5.81-5.76 (1H, m), 5.56 (1H, d), 2.79 (3H, s), 1.66 (3H, d), 1.39 (9H, s).

[0253] Intermediate 2-13 LCMS: 359 [M+H]+, RT = 1.62 points (Analyzer: LCMS-2020)

[0254] Intermediate 2-15 1 H-NMR (CDCl3) δ: 8.40 (1H, d), 8.29 (1H, d), 8.03 (1H, s), 5.92-5.85 (1H, m), 5.60-5.52 (1H, m), 4.13 (3H, s), 1.67 (3H, d), 1.38 (9H, s).

[0255] Intermediate 2-16 1 H-NMR (CDCl3) δ: 8.53 (1H, d), 8.00 (1H, s), 6.75 (1H, d), 6.07-6.00 (1H, m), 5.64 (1H, d), 4.13 (3H, s), 1.58 (3H, d), 1.42 (9H, s).

[0256] Intermediate 2-17 1 H-NMR (CDCl3) δ: 9.28 (1H, s), 8.31 (1H, d), 8.01 (1H, s), 6.10-6.03 (1H, m), 5.53 (1H, d), 1.59 (3H, d), 1.42 (9H, s).

[0257] Intermediate 2-18 1 H-NMR (CDCl3) δ: 8.46 (1H, dd), 7.93 (1H, s), 7.89 (1H, d), 7.85 (1H, dd), 5.90-5.85 (1H, m), 5.60-5.55 (1H, m), 1.55 (3H, d), 1.42 (9H, s).

[0258] Intermediate 2-19 LCMS: 417 [M+H]+, RT = 1.58 minutes (Analyzer: LCMS-2020)

[0259] Intermediate 2-20 LCMS: 314 [M+H]+, RT = 1.58 minutes (examiner: LCMS-2020)

[0260] Intermediate 2-21 1 H-NMR (CDCl3) δ: 7.96 (1H, s), 7.54-7.50 (2H, m), 7.24-7.21 (2H, m), 5.34-5.27 (1H, m), 5.04-4.99 (1H, m), 1.42-1.40 (12H, m).

[0261] Intermediate 2-22 1 H-NMR (CDCl3) δ: 7.97 (1H, s), 7.55-7.48 (5H, m), 5.39-5.35 (1H, m), 5.10-5.06 (1H, m), 1.43-1.39 (12H, m).

[0262] Intermediate 2-23 1 H-NMR (CDCl3) δ: 8.00 (1H, s), 7.90-7.87 (2H, m), 7.78 (1H, d), 7.68 (1H, t), 5.27-5.25 (1H, m), 5.05-5.03 (1H, m), 1.48 (3H, d), 1.41 (9H, s).

[0263] Reference Production Example 6-2 A mixture of 1.9 g of N-(tert-butoxycarbonyl)alaninamide, 3.3 mL of N,N-dimethylformamide dimethyl acetal, and 15 mL of chloroform was heated to 70°C and stirred for 2 hours. The resulting reaction solution was cooled to room temperature and then concentrated. The resulting residue was mixed with 10 mL of 1,2-dimethoxyethane, and 1.9 g of 5-bromo-2-hydrazinopyrimidine and 5.0 mL of acetic acid were added, followed by stirring at 60°C for 5 hours. Aqueous sodium bicarbonate was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=8:2) to obtain 1.0 g of Intermediate 2-14 represented by the following formula: Intermediate 2-14 LCMS: 369 / 371 (1:1) [M+H] +, RT = 1.53 min (Detector: LCMS-2020)

[0264] Reference Production Example 7: 30 mL of a 4% ammonia methanol solution was added to 0.50 g of Intermediate 2-7 at room temperature, and the mixture was stirred at room temperature for 24 hours and then at 60° C. for 7 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:methanol=8:2) to obtain 0.34 g of Intermediate 2-6 represented by the following formula. Intermediate 2-6 1 H-NMR (DMSO-D6) δ: 8.69 (1H, dd), 8.39 (1H, s), 8.27 (1H, dd), 7.97 (1H, dd), 5.30 (1H, q), 1.59 (3H, d).

[0265] Reference Production Example 8 A mixture of 5.0 g of 2-bromopropanamide, 6.6 mL of N,N-dimethylformamide dimethyl acetal, and 20 mL of chloroform was heated to 100°C and stirred for 2 hours. The resulting reaction solution was cooled to room temperature and then concentrated. The resulting residue was mixed with 20 mL of dimethoxyethane, and 4.9 g of 5-chloro-2-hydrazinopyridine and 20 mL of acetic acid were added, followed by stirring at 60°C for 18 hours. Water was added to the resulting mixture, and the resulting solid was filtered. The resulting solid was washed successively with water and hexane and then dried to obtain 2.0 g of intermediate 2-7 represented by the following formula: Intermediate 2-7 1 H-NMR (CDCl3) δ: 8.49 (1H, d), 7.99 (1H, s), 7.92-7.86 (2H, m), 6.38 (1H, q), 2.22 (3H, d).

[0266] Reference Production Example 9: Production was carried out according to Reference Production Example 5, except that N,N-dimethylacetamide dimethyl acetal was used instead of N,N-dimethylformamide dimethyl acetal. Intermediate 2-8 LCMS: 305 [M+H] + , RT = 1.274 min (detector: LCMS-2020)

[0267] Reference Production Example 9-2 A compound prepared in accordance with Reference Production Example 5 using N,N-dimethylacetamide dimethyl acetal instead of N,N-dimethylformamide dimethyl acetal and 5-chloro-2-hydrazinopyridine instead of 2-hydrazinopyridine and its physical properties are shown below. Intermediate 2-24 1 H-NMR (CDCl3) δ: 8.43 (1H, dd), 7.84 (1H, d), 7.81 (1H, dd), 5.85-5.80 (1H, m), 5.59-5.54 (1H, m), 2.42 (3H, s), 1.54 (3H, d), 1.42 (9H, s).

[0268] Reference Production Example 9-3 Production was carried out in accordance with Reference Production Example 5, except that N,N-dimethylacetamide dimethyl acetal was used instead of N,N-dimethylformamide dimethyl acetal and 2-hydrazinopyrimidine was used instead of 2-hydrazinopyridine. Intermediate 2-8 LCMS: 305 [M+H] + , RT = 1.27 min (detector: LCMS-2020)

[0269] Reference Production Example 10: To a mixture of 1.5 g of Intermediate 7-5 and 15 mL of chloroform, 4.2 mL of a hydrogen chloride / 1,4-dioxane solution (4 mol / L) was added, and the mixture was stirred at room temperature for 16 hours and then concentrated. Water was added to the resulting residue, and the mixture was washed with tert-butyl methyl ether. After that, a 1 mol / L aqueous sodium hydroxide solution was added to adjust the pH to 8, and the mixture was extracted with chloroform. The resulting organic layer was dried over sodium sulfate and concentrated to obtain 0.97 g of Intermediate 3-1 represented by the following formula: Intermediate 3-1 LCMS: 350 [M+H] +, RT = 1.31 min (detector: LCMS-2020)

[0270] Reference Production Example 11: To a mixture of 2.2 g of (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid and 30 mL of chloroform, a catalytic amount of dimethylformamide and 1.3 mL of oxalyl chloride were added at room temperature, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated to obtain mixture F. Subsequently, to a mixture of 1.7 g of ethyl 2-methylpropanimidate hydrochloride and 30 mL of THF, 7.1 mL of diisopropylethylamine and mixture F were added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. To the resulting mixture, 1.3 g of 2-hydrazinopyrimidine was added at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=9:1) to obtain 2.2 g of intermediate 3-2 represented by the following formula. Intermediate 3-2 1 H-NMR (CDCl3) δ: 8.70 (2H, d), 7.79 (2H, dd), 7.68 (2H, dd), 7.16 (1H, t), 6.26 (1H, q), 3.26-3.16 (1H, m), 1.97 (3H, d), 1.41 (6H, dd).

[0271] Reference Production Example 12 Compounds prepared according to Reference Production Example 11 and their physical properties are shown below. Intermediate 3-3 1 H-NMR (CDCl3) δ: 8.71 (2H, d), 7.80 (2H, dd), 7.69 (2H, dd), 7.19 (1H, t), 6.30 (1H, q), 2.52 (3H, s), 1.99 (3H, d).

[0272] Intermediate 3-4 1 H-NMR (CDCl3) δ: 8.70 (2H, d), 7.80 (2H, dd), 7.68 (2H, dd), 7.18 (1H, t), 6.28 (1H, q), 2.88 (2H, q), 1.98 (3H, d), 1.38 (3H, t).

[0273] Intermediate 3-5 1 H-NMR (CDCl3) δ: 8.54-8.54 (1H, m), 8.01-7.99 (2H, m), 7.80 (2H, dd), 7.70 (2H, dd), 6.23 (1H, q), 2.49 (3H, s), 1.97 (3H, d).

[0274] Intermediates 3-6 1 H-NMR (CDCl3) δ: 8.19 (1H, d), 7.79-7.75 (3H, m), 7.69-7.66 (3H, m), 6.15 (1H, q), 2.10-2.06 (1H, m), 1.92 (3H, d), 1.07-0.97 (4H, m).

[0275] Intermediate 3-7 1 H-NMR (CDCl3) δ: 8.29 (1H, dd), 7.81 (1H, dd), 7.79-7.77 (2H, m), 7.70 (1H, t), 7.68 (2H, dd), 6.15 (1H, q), 2.10-2.06 (1H, m), 1.92 (3H, d), 1.07-0.97 (4H, m).

[0276] Intermediate 3-8 1 H-NMR (CDCl3) δ: 8.04 (1H, d), 7.82-7.79 (2H, m), 7.71-7.68 (2H, m), 7.57 (1H, d), 6.27 (1H, q), 2.06 (1H, tt), 2.00 (3H, d), 1.06-0.96 (4H, m).

[0277] Intermediate 3-9 1 H-NMR (CDCl3) δ: 8.05 (1H, d), 7.83-7.80 (2H, m), 7.71-7.68 (2H, m), 7.59 (1H, d), 6.31 (1H, q), 2.45 (3H, s), 2.03 (3H, d).

[0278] Intermediate 3-10 1 H-NMR (CDCl3) δ: 8.65 (2H, s), 7.83-7.80 (2H, m), 7.72-7.69 (2H, m), 6.22 (1H, q), 2.52 (3H, s), 1.98 (3H, d).

[0279] Intermediate 3-11 1 H-NMR (CDCl3) δ: 8.52 (1H, dd), 7.99-7.98 (2H, m), 7.81-7.77 (2H, m), 7.72-7.67 (2H, m), 6.18 (1H, q), 2.13-2.06 (1H, m), 1.94 (3H, d), 1.10-0.99 (4H, m).

[0280] Intermediate 3-12 1 H-NMR (CDCl3) δ: 8.89 (1H, d), 8.73 (1H, d), 7.84 (1H, dd), 7.81-7.78 (2H, m), 7.71-7.68 (2H, m), 6.30 (1H, q), 2.48 (3H, s), 1.99 (3H, d).

[0281] Intermediate 3-13 1 H-NMR (CDCl3) δ: 7.99 (1H, s), 7.82 (2H, dd), 7.71 (2H, dd), 6.10 (1H, q), 3.87 (3H, s), 2.46 (3H, s), 1.98 (3H, d).

[0282] Reference Production Example 13: To a mixture of 1.5 g of intermediate 3-2 and 10 mL of ethanol, 0.60 mL of hydrazine monohydrate was added at room temperature, and the mixture was heated to 70°C and stirred for 30 minutes. The resulting mixture was cooled to room temperature, water was added, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to obtain 0.47 g of intermediate 4-1 represented by the following formula: Intermediate 4-1 1H-NMR (CDCl3) δ: 8.85 (2H, d), 7.30 (1H, t), 4.85 (1H, q), 3.24-3.13 (1H, m), 1.57 (3H, d), 1.40 (6H, dd).

[0283] Reference Production Example 14: 14 mL of a methylamine / THF solution (2 mol / L) was added to 1.0 g of Intermediate 2-15, and the mixture was stirred at room temperature for 7 hours. The resulting mixture was concentrated to obtain 0.90 g of Intermediate 2-25 represented by the following formula. Intermediate 2-25 1 H-NMR (DMSO-D6) δ: 9.03 (1H, d), 8.10 (1H, d), 7.97 (1H, d), 7.94 (1H, s), 7.21 (1H, d), 5.28-5.23 (1H, m), 2.53 (3H, d), 1.13 (3H, d), 0.93 (9H, s).

[0284] Reference Production Example 15: To a mixture of 2.2 g of (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid and 33 mL of dimethylformamide, 4.6 g of O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 1.4 g of methyl 2-amino-2-iminoacetate hydrochloride, and 5.4 mL of diisopropylethylamine were added, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture, 1.1 g of 2-hydrazinopyrimidine and 5.7 mL of acetic acid were added, and the mixture was stirred at 80°C for 3 hours. The resulting mixture was cooled to room temperature, and a saturated aqueous solution of sodium bicarbonate was added to adjust the pH to 8, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=9:1) to obtain 2.1 g of intermediate 3-14 represented by the following formula. Intermediate 3-14 LCMS: 379 [M+H] +, RT = 1.43 min (detector: LCMS-2020)

[0285] Reference Production Example 16: To a mixture of 0.45 g of Intermediate 5-2 and 12 mL of methanol, 1.8 g of ammonium acetate was added and stirred at 65°C for 2 hours, then cooled to room temperature. 0.53 g of sodium cyanoborohydride and a catalytic amount of acetic acid were added and stirred at 65°C for 5 hours. The resulting mixture was cooled to room temperature, water was added, and the mixture was washed with hexane. A 1 mol / L aqueous solution of sodium hydroxide was added to the resulting aqueous layer to adjust the pH to 12, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to obtain 0.25 g of Intermediate 5-1 represented by the following formula: Intermediate 5-1 1 H-NMR (CDCl3) δ: 8.71 (1H, d), 8.43 (1H, d), 8.38 (1H, d), 7.89 (1H, d), 4.79 (1H, q), 1.53 (3H, d).

[0286] Reference Production Example 17: To a mixture of 1.0 g of 1-(3-chloropyrazin-2-yl)ethanone and 6.4 mL of dimethylformamide, 0.48 g of 2H-1,2,3-triazole and 1.8 g of potassium carbonate were added and stirred at 60°C for 5 hours. The resulting mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 0.45 g of intermediate 5-2 represented by the following formula: Intermediate 5-2 1 H-NMR (CDCl3) δ: 8.68 (1H, d), 8.61 (1H, d), 8.39 (1H, d), 7.87 (1H, d), 2.80 (3H, s).

[0287] Reference Production Example 18: A mixture of 3 g of intermediate 3-8, 1.1 mL of α-benzaldoxime, 6.2 g of cesium carbonate, and 12 mL of DMF was stirred at 60°C for 3 hours. The resulting mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 7:3) to obtain 1.0 g of intermediate 3-15 represented by the following formula: Intermediate 3-15 1 H-NMR (CDCl3) δ: 7.79-7.75 (3H, m), 7.72-7.70 (2H, m), 6.94 (1H, d), 5.89 (1H, q), 2.07 (1H, tt), 1.90 (3H, d), 1.05-0.97 (4H, m).

[0288] Reference Production Example 19 Compounds and their physical properties are shown below, which were prepared according to Reference Production Example 18, using Intermediate 3-9 instead of Intermediate 3-8. Intermediate 3-16 1 H-NMR (CDCl3) δ: 10.06 (1H, br s), 7.82-7.78 (3H, m), 7.73-7.70 (2H, m), 6.97 (1H, d), 5.92 (1H, q), 2.46 (3H, s), 1.94 (3H, d).

[0289] Reference Production Example 20: To a mixture of 1.0 g of Intermediate 3-15, 1.0 g of cesium carbonate, and 5.0 mL of acetonitrile, 0.19 mL of methyl iodide was added and stirred at room temperature for 10 hours. The resulting mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:5) to obtain 1.1 g of Intermediate 3-17 represented by the following formula. Intermediate 3-17 1 H-NMR (CDCl3) δ: 7.78-7.76 (2H, m), 7.73-7.71 (2H, m), 7.65 (1H, d), 6.86 (1H, d), 5.89 (1H, q), 3.62 (3H, s), 2.10-2.05 (1H, m), 1.91 (3H, d), 1.06-0.99 (4H, m).

[0290] Reference Production Example 21 Compounds and their physical properties are shown below, which were prepared according to Reference Production Example 20, except that Intermediate 3-16 was used instead of Intermediate 3-15. Intermediate 3-18 1 H-NMR (CDCl3) δ: 7.79-7.76 (2H, m), 7.73-7.70 (2H, m), 7.64 (1H, d), 6.87 (1H, d), 5.93 (1H, q), 3.64 (3H, s), 2.47 (3H, s), 1.94 (3H, d).

[0291] Reference Preparation Example 22: 0.46 g of Intermediate 7-7 was mixed with 3.0 mL of acetonitrile, and 0.51 g of di(N-succinimidyl)carbonate and 1.4 mL of diisopropylethylamine were added at room temperature. The mixture was stirred for 1 hour and then concentrated. The resulting residue was mixed with 1.5 mL of water and 3.0 mL of acetonitrile, and 1.1 g of sodium carbonate and 0.30 g of 5-(difluoromethyl)-2-amino-1,3,4-thiadiazole were added at room temperature. The mixture was stirred for 1 hour. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate) to obtain 0.15 g of Intermediate 6-1 represented by the following formula: Intermediate 6-1 1 H-NMR (CDCl3) δ: 12.10 (1H, br s), 8.88 (2H, d), 7.33 (1H, t), 7.06-6.92 (1H, m), 6.99 (1H, t), 6.21-6.18 (1H, m), 2.20-2.16 (1H, m), 1.65 (3H, d), 1.10-0.97 (4H, m).

[0292] Reference Production Example 22-2 Compounds prepared according to Reference Production Example 22 and their physical properties are shown below. Intermediate 6-2 1H-NMR (CDCl3) δ: 8.93 (2H, d), 8.09 (1H, s), 7.41 (1H, t), 6.94 (1H, t), 6.30-6.28 (1H, m), 1.70 (3H, d).

[0293] Reference Production Example 23: To a mixture of 0.60 g of Intermediate 7-8 and 5.0 mL of ethanol, 0.22 g of 2-hydrazinopyrimidine was added and stirred at 90°C for 3 hours. The resulting mixture was cooled to room temperature and concentrated, and ethyl acetate was added to the residue. The resulting organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 9:1) to obtain 0.22 g of Intermediate 3-19 represented by the following formula. Intermediate 3-19 1 H-NMR (CDCl3) δ: 8.72 (2H, d), 7.80 (2H, dd), 7.69 (2H, dd), 7.17 (1H, t), 6.29 (1H, q), 4.10 (3H, s), 1.97 (3H, d).

[0294] Reference Production Example 24: To a mixture of 1.1 g of (2S)-2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)propanoic acid and 15 mL of chloroform, a catalytic amount of dimethylformamide and 0.64 mL of oxalyl chloride were added at room temperature, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, and to the resulting residue, 50 mL of acetonitrile and 0.38 g of ammonium thiocyanate were added at room temperature, and the mixture was stirred at room temperature for 18 hours. To the resulting mixture, 0.55 g of 2-hydrazinopyrimidine was added, and the mixture was stirred at 80°C for 8 hours. The resulting mixture was cooled to room temperature and concentrated. To a mixture of the resulting residue and 30 mL of dimethylformamide, 0.20 g of sodium hydride (60%, dispersed in liquid paraffin) was added, and the mixture was stirred at room temperature for 10 minutes. After that, 0.37 mL of methyl iodide was added, and the mixture was stirred at room temperature for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=9:1) to obtain 0.67 g of intermediate 3-20 represented by the following formula. Intermediate 3-20 1 H-NMR (CDCl3) δ: 8.72 (2H, d), 7.80 (2H, dd), 7.69 (2H, dd), 7.19 (1H, t), 6.29 (1H, q), 2.67 (3H, s), 1.98 (3H, d).

[0295] Reference Production Example 25: To a mixture of 0.80 g of Intermediate 2-27 and 5.0 mL of dimethylformamide, 4.1 g of cesium carbonate and 2.4 mL of acetic anhydride were added and stirred at 100°C for 6 hours. The resulting mixture was allowed to cool to room temperature, water was added, and extraction was performed with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 9:1) to obtain 0.22 g of Intermediate 2-26 represented by the following formula. Intermediate 2-26 LCMS: 362 [M+H] + , RT = 1.56 min (detector: LCMS-2050)

[0296] Reference Production Example 26: 15 mL of a methylamine / methanol solution (about 40%) was added to 0.97 g of Intermediate 7-9 at room temperature, and the mixture was stirred for 4 hours at 50° C. The resulting mixture was allowed to cool to room temperature and concentrated to obtain 1.2 g of Intermediate 2-27 represented by the following formula. Intermediate 2-27 1 H-NMR (CDCl3) δ: 8.47 (1H, s), 7.91 (1H, s), 6.87 (1H, s), 6.03-6.02 (1H, m), 5.78-5.75 (1H, m), 3.01 (3H, d), 1.55 (3H, d), 1.42 (9H, s).

[0297] Reference Preparation Example 27: To 1.0 g of Intermediate 7-9 in a pressure-resistant reaction vessel, 0.27 g of acetamide, 0.18 g of Xantphos, 2.0 g of cesium carbonate, 0.14 g of tris(dibenzylideneacetone)dipalladium(0), and 6.0 mL of toluene were added, and the vessel was sealed. The resulting mixture was stirred at 100°C for 1 hour using a microwave reaction apparatus. The resulting mixture was cooled to room temperature and concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane = 4:1) to obtain 0.26 g of Intermediate 2-28 represented by the following formula: Intermediate 2-28 1 H-NMR (CDCl3) δ: 8.74 (1H, d), 8.69 (1H, s), 8.10-8.08 (1H, m), 7.96 (1H, s), 6.07-6.03 (1H, m), 5.64-5.60 (1H, m), 2.28 (3H, s), 1.56 (3H, d), 1.42 (9H, s).

[0298] Reference Production Example 28: To a mixture of 1.2 g of 2-amino-5-methyl-1,3,4-thiadiazole and 3.3 mL of dimethylformamide, 1.9 mL of methyl iodide was added and stirred at 45°C for 8 hours. The resulting mixture was allowed to cool to room temperature, and a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate. The resulting organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated to obtain 0.41 g of intermediate 39 represented by the following formula: Intermediate 39 1 H-NMR (CDCl3) δ: 6.37 (1H, br s), 3.48 (3H, s), 2.28 (3H, s).

[0299] Reference Production Example 29-1 Intermediate 7-1 represented by the following formula is a compound described in WO 2021 / 069569 and was produced in accordance with the method described in the publication. Intermediate 7-1

[0300] Reference Production Example 29-2 Intermediate 7-2 represented by the following formula is a compound described in WO 2021 / 083936 and was produced in accordance with the method described in the publication. Intermediate 7-2

[0301] Reference Production Example 29-3 Intermediate 7-3 represented by the following formula is a compound described in WO 2021 / 069569 and was produced in accordance with the method described in the publication. Intermediate 7-3

[0302] Reference Production Example 29-4 Intermediate 7-4 represented by the following formula is a compound described in WO 2021 / 105091 and was produced in accordance with the method described in the publication. Intermediate 7-4

[0303] Reference Production Example 29-5 Intermediate 7-5 represented by the following formula is a compound described in WO 2021 / 069567 and was produced in accordance with the method described in the publication. Intermediate 7-5

[0304] Reference Production Example 29-7 Intermediate 7-7 represented by the following formula is a compound described in WO 2024 / 101172, and was produced according to the method described in the publication. Intermediate 7-7

[0305] Reference Production Example 29-8 Intermediate 7-8 represented by the following formula is a compound described in WO 2021 / 105091 and was produced in accordance with the method described in the publication. Intermediate 7-8

[0306] Reference Production Example 29-9 Intermediates 7-9 and 7-10 represented by the following formulas are compounds described in WO 2021 / 165195 and were produced in accordance with the method described in the publication. Intermediate 7-9

[0307] Intermediate 7-10

[0308] Next, examples of the compound of the present invention that can be produced according to any of the production methods described in the Examples and the production methods described in this specification are shown below.

[0309] Formula (L-1) In the compound represented by the formula (hereinafter referred to as compound (L-1)), R 3 is a hydrogen atom, and R 2 is listed in [Table L1] (# 1represents the bonding site to the nitrogen atom at the 1-position of the 1,2,4-triazole ring), and X is any of the groups listed in [Table T1-1] to [Table T1-20] (# 4 represents the bonding site to the carbon atom of the carbonyl group) (hereinafter referred to as compound group SX1).

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L2 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX2).

[0319] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L3 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX3).

[0320] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L4 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX4).

[0321] In compound (L-1), R 3 is a hydrogen atom, and R 2is L5 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX5).

[0322] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L6 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX6).

[0323] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L7 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX7).

[0324] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L8 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX8).

[0325] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L9 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX9).

[0326] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L10 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX10).

[0327] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L11 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX11).

[0328] In compound (L-1), R 3is a hydrogen atom, and R 2 is L12 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX12).

[0329] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L13 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX13).

[0330] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L14 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX14).

[0331] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L15 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX15).

[0332] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L16 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX16).

[0333] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L17 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX17).

[0334] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L18 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX18).

[0335] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L19 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX19).

[0336] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L20 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX20).

[0337] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L21 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX21).

[0338] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L22 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX22).

[0339] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L23 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX23).

[0340] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L24 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX24).

[0341] In compound (L-1), R 3 is a hydrogen atom, and R 2is L25 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX25).

[0342] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L26 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX26).

[0343] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L27 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX27).

[0344] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L28 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX28).

[0345] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L29 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX29).

[0346] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L30 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX30).

[0347] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L31 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX31).

[0348] In compound (L-1), R3 is a hydrogen atom, and R 2 is L32 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX32).

[0349] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L33 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX33).

[0350] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L34 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX34).

[0351] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L35 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX35).

[0352] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L36 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX36).

[0353] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L37 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX37).

[0354] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L38 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX38).

[0355] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L39 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX39).

[0356] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L40 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX40).

[0357] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L41 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX41).

[0358] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L42 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX42).

[0359] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L43 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX43).

[0360] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L44 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX44).

[0361] In compound (L-1), R 3 is a hydrogen atom, and R 2is L45 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX45).

[0362] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L46 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX46).

[0363] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L47 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX47).

[0364] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L48 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX48).

[0365] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L49 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX49).

[0366] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L50 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX50).

[0367] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L51 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX51).

[0368] In compound (L-1), R3 is a hydrogen atom, and R 2 is L52 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX52).

[0369] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L53 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX53).

[0370] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L54 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX54).

[0371] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L55 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX55).

[0372] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L56 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX56).

[0373] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L57 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX57).

[0374] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L58 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX58).

[0375] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L59 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX59).

[0376] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L60 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX60).

[0377] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L61 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX61).

[0378] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L62 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX62).

[0379] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L63 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX63).

[0380] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L64 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX64).

[0381] In compound (L-1), R 3 is a hydrogen atom, and R 2is L65 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX65).

[0382] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L66 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX66).

[0383] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L67 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX67).

[0384] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L68 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX68).

[0385] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L69 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX69).

[0386] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L70 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX70).

[0387] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L71 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX71).

[0388] In compound (L-1), R3 is a hydrogen atom, and R 2 is L72 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX72).

[0389] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L73 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX73).

[0390] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L74 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX74).

[0391] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L75 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX75).

[0392] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L76 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX76).

[0393] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L77 described in [Table L5], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX77).

[0394] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L78 described in [Table L6], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX78).

[0395] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L79 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX79).

[0396] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L80 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX80).

[0397] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L81 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX81).

[0398] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L82 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX82).

[0399] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L83 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX83).

[0400] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L84 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX84).

[0401] In compound (L-1), R 3 is a hydrogen atom, and R 2is L85 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX85).

[0402] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L86 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX86).

[0403] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L87 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX87).

[0404] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L88 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX88).

[0405] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L89 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX89).

[0406] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L90 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX90).

[0407] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L91 described in [Table L7], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX91).

[0408] In compound (L-1), R3 is a hydrogen atom, and R 2 is L92 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX92).

[0409] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L93 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX93).

[0410] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L94 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX94).

[0411] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L95 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX95).

[0412] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L96 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX96).

[0413] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L97 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX97).

[0414] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L98 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX98).

[0415] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L99 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX99).

[0416] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L100 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX100).

[0417] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L101 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX101).

[0418] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L102 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX102).

[0419] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L103 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX103).

[0420] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L104 described in [Table L8], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX104).

[0421] In compound (L-1), R 3 is a hydrogen atom, and R 2is L105 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX105).

[0422] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L106 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX106).

[0423] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L107 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX107).

[0424] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L108 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX108).

[0425] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L109 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX109).

[0426] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L110 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX110).

[0427] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L111 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX111).

[0428] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L112 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX112).

[0429] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L113 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX113).

[0430] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L114 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX114).

[0431] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L115 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX115).

[0432] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L116 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX116).

[0433] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L117 described in [Table L9], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX117).

[0434] In compound (L-1), R 3 is a hydrogen atom, and R 2is L118 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX118).

[0435] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L119 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX119).

[0436] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L120 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX120).

[0437] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L121 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX121).

[0438] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L122 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX122).

[0439] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L123 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX123).

[0440] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L124 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX124).

[0441] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L125 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX125).

[0442] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L126 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX126).

[0443] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L127 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX127).

[0444] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L128 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX128).

[0445] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L129 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX129).

[0446] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L130 described in [Table L10], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX130).

[0447] In compound (L-1), R 3 is a hydrogen atom, and R 2is L131 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX131).

[0448] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L132 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX132).

[0449] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L133 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX133).

[0450] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L134 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX134).

[0451] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L135 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX135).

[0452] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L136 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX136).

[0453] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L137 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX137).

[0454] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L138 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX138).

[0455] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L139 described in [Table L11], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX139).

[0456] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L140 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX140).

[0457] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L141 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX141).

[0458] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L142 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX142).

[0459] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L143 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX143).

[0460] In compound (L-1), R 3 is a hydrogen atom, and R 2is L144 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX144).

[0461] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L145 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX145).

[0462] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L146 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX146).

[0463] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L147 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX147).

[0464] In compound (L-1), R 3 is a hydrogen atom, and R 2 is L148 described in [Table L12], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX148).

[0465] In compound (L-1), R 3 is a methyl group, and R 2 is L1 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX149).

[0466] In compound (L-1), R 3 is a methyl group, and R 2 is L2 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX150).

[0467] In compound (L-1), R 3 is a methyl group, and R 2 is L3 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX151).

[0468] In compound (L-1), R 3 is a methyl group, and R 2 is L4 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX152).

[0469] In compound (L-1), R 3 is a methyl group, and R 2 is L5 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX153).

[0470] In compound (L-1), R 3 is a methyl group, and R 2 is L6 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX154).

[0471] In compound (L-1), R 3 is a methyl group, and R 2 is L7 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX155).

[0472] In compound (L-1), R 3 is a methyl group, and R 2 is L8 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX156).

[0473] In compound (L-1), R 3 is a methyl group, and R 2is L9 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX157).

[0474] In compound (L-1), R 3 is a methyl group, and R 2 is L10 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX158).

[0475] In compound (L-1), R 3 is a methyl group, and R 2 is L11 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX159).

[0476] In compound (L-1), R 3 is a methyl group, and R 2 is L12 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX160).

[0477] In compound (L-1), R 3 is a methyl group, and R 2 is L13 described in [Table L1], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX161).

[0478] In compound (L-1), R 3 is a methyl group, and R 2 is L14 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX162).

[0479] In compound (L-1), R 3 is a methyl group, and R 2 is L15 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX163).

[0480] In compound (L-1), R 3 is a methyl group, and R 2 is L16 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX164).

[0481] In compound (L-1), R 3 is a methyl group, and R 2 is L17 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX165).

[0482] In compound (L-1), R 3 is a methyl group, and R 2 is L18 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX166).

[0483] In compound (L-1), R 3 is a methyl group, and R 2 is L19 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX167).

[0484] In compound (L-1), R 3 is a methyl group, and R 2 is L20 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX168).

[0485] In compound (L-1), R 3 is a methyl group, and R 2 is L21 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX169).

[0486] In compound (L-1), R 3 is a methyl group, and R 2is L22 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX170).

[0487] In compound (L-1), R 3 is a methyl group, and R 2 is L23, and X is any of the substituents described in [Table T1-1] to [Table T1-20], or a compound described in [Table L2] (hereinafter referred to as compound group SX171).

[0488] In compound (L-1), R 3 is a methyl group, and R 2 is L24 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX172).

[0489] In compound (L-1), R 3 is a methyl group, and R 2 is L25 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX173).

[0490] In compound (L-1), R 3 is a methyl group, and R 2 is L26 described in [Table L2], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX174).

[0491] In compound (L-1), R 3 is a methyl group, and R 2 is L27 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX175).

[0492] In compound (L-1), R 3 is a methyl group, and R 2 is L28 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX176).

[0493] In compound (L-1), R 3 is a methyl group, and R 2 is L29 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX177).

[0494] In compound (L-1), R 3 is a methyl group, and R 2 is L30 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX178).

[0495] In compound (L-1), R 3 is a methyl group, and R 2 is L31 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX179).

[0496] In compound (L-1), R 3 is a methyl group, and R 2 is L32 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX180).

[0497] In compound (L-1), R 3 is a methyl group, and R 2 is L33 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX181).

[0498] In compound (L-1), R 3 is a methyl group, and R 2 is L34 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX182).

[0499] In compound (L-1), R 3 is a methyl group, and R 2is L35 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX183).

[0500] In compound (L-1), R 3 is a methyl group, and R 2 is L36 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX184).

[0501] In compound (L-1), R 3 is a methyl group, and R 2 is L37 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX185).

[0502] In compound (L-1), R 3 is a methyl group, and R 2 is L38 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX186).

[0503] In compound (L-1), R 3 is a methyl group, and R 2 is L39 described in [Table L3], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX187).

[0504] In compound (L-1), R 3 is a methyl group, and R 2 is L40 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX188).

[0505] In compound (L-1), R 3 is a methyl group, and R 2 is L41 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX189).

[0506] In compound (L-1), R 3 is a methyl group, and R 2 is L42 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX190).

[0507] In compound (L-1), R 3 is a methyl group, and R 2 is L43 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX191).

[0508] In compound (L-1), R 3 is a methyl group, and R 2 is L44 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX192).

[0509] In compound (L-1), R 3 is a methyl group, and R 2 is L45 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX193).

[0510] In compound (L-1), R 3 is a methyl group, and R 2 is L46 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX194).

[0511] In compound (L-1), R 3 is a methyl group, and R 2 is L47 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX195).

[0512] In compound (L-1), R 3 is a methyl group, and R 2is L48 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX196).

[0513] In compound (L-1), R 3 is a methyl group, and R 2 is L49 described in [Table L4], and X is any of the substituents described in [Table T1-1] to [Table T1-20] (hereinafter referred to as compound group SX...

Claims

Formula (I) [During the ceremony, R １ represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; R ２ represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group A, a phenyl group optionally substituted with one or more substituents selected from group A, a 9-membered aromatic heterocyclic group {the 9-membered aromatic heterocyclic group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4 (# 1 represents a bonding site with Q), R a11 , R a12 , R a33 , and R a34 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, a C(O)OR aa1 , C(O)NR aa2 R aa3 , a cyano group, a halogen atom, or a hydrogen atom; R a21 , R a23 , R a42 , and R a44 are the same or different and represent a halogen atom or a hydrogen atom, R aa1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a hydrogen atom; R aa2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R aa3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R a31 , R a32 , R a53 , or R a54 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a phenyl group optionally substituted with one or more substituents selected from Group C, a cyclopropyl group, and a halogen atom, or a hydrogen atom; R 3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group B, a cyclopropyl group, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkylsulfonyl group, OR 3a , C(O)R 3b , C(O)OR 3c or a hydrogen atom, R 3a represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R 3b represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, and a halogen atom), a phenyl group optionally substituted with one or more substituents selected from Group C, a cyclopropyl group, or a hydrogen atom; R 3c represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, and a halogen atom}, a phenyl group optionally substituted with one or more substituents selected from Group C, or a cyclopropyl group, Q is a group represented by formula B1, a group represented by formula B2, or a group represented by formula B3 (# 2 is R 1 represents the bonding site with the carbon atom to which it is bonded, and # 3 is R 2 represents a binding site with R b11 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, NR ba1 C(O)R ba2 , N.R. ba3 C(O)OR ba4 , N.R. ba5 R ba6 , C(O)NR ba7 R ba8 , C(O)OR ba9 , S(O) ｑ R ba10 , a cyano group, or a hydrogen atom; R ba1 represents a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, C(O)R ba11 or a hydrogen atom, R ba2 , R ba4 , R ba9 , R ba10 , and R ba11 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, R ba3 , R ba5 , R ba6 , R ba7 and R ba8 are the same or different and represent a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; q represents 0, 1, or 2; R b21 , and R b22 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, or a hydrogen atom; R b31 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, NR bb1 C(O)R bb2 , N.R. bb3 C(O)OR bb4 , N.R. bb5 C(O)NR bb6 R bb7 , N.R. bb8 S(O)2R bb9 , N.R. bb10 R bb11 , a nitro group, a cyano group, a halogen atom, or a hydrogen atom; R bb1 , R bb3 , R bb5 , R bb6 , R bb8 , and R bb10 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb2 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, a cyclopropyl group, or a hydrogen atom; R bb4 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom, or a cyclopropyl group; R bb7 and R bb11 are the same or different and represent a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; R bb9 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a cyclopropyl group; R ｂ32 represents a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, C(O)NR bb12 R bb13 , C(O)OR bb14 , S(O) ２ R bb15 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; R bb12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a hydrogen atom; R bb14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R bb15 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a cyclopropyl group; Z 1 is an oxygen atom, a sulfur atom, NR ZZ1 , N-OR ZZ2 , N-CN, N-NO ２ , C(CN) ２ , NS(O) ２ R ZZ3 , or NC(O)OR ZZ4 represents R ZZ1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R ZZ2 represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R ZZ3 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from group C. R ZZ4 represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), a phenyl group which may be substituted with one or more substituents selected from Group C, or a cyclopropyl group; X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1 (# 4 is Z 1 represents the bonding site with the carbon atom bonded to Z 2 represents an oxygen atom or a sulfur atom, Z 3 is a nitrogen atom or CR C14 represents Z 4 , Z 5 , Z 6 and Z 7 The combination of Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is a nitrogen atom, and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Z 4 is CR C21 and Z 5 is a nitrogen atom, and Z 6 is CR C23 and Z 7 is CR C24 A combination in which: Or, Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 represents a combination in which the atom is a nitrogen atom, R c21 , R c31 , R c14 , R c24 , and R c34 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), NR cc1 C(O)R cc2 , C(O)NR cc3 R cc4 , C(O)OR cc5 , OR cc6 , S(O) ２ R cc7 , a nitro group, a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are each a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, a cyclopropyl group, a cyano group, and a halogen atom}, a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, C(O)NR cc8 R cc9 , C(O)R cc10 , or S(O) ２ R cc11 represents R cc1 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, OR 1C or a hydrogen atom, R 1C represents a cyclopropyl group, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), or a hydrogen atom; R cc2 and R cc4 are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc3 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc5 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R cc6 represents a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyclopropyl group and a halogen atom), C(O)R 61C , C(O)OR 62C , C(O)NR 63C R 64C , S(O)R 65C or a hydrogen atom, R 61C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 62C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R 63C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 64C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 65C represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R cc7 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R cc8 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R cc9 represents a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a phenyl group which may be substituted with one or more substituents selected from Group C, and a halogen atom), a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom; R cc10 and R cc11 are the same or different and represent a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group is optionally substituted with one or more substituents selected from the group consisting of a phenyl group optionally substituted with one or more substituents selected from Group C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group C, a cyclopropyl group, and a halogen atom}, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom, Group A: C1-C6 chain hydrocarbon groups {the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from the group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom}, a cyclopropyl group {the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, OR 1A , SF5, NR 2A C(O)R 3A , N.R. 4A C(O)OR 5A , N.R. 6A C(O)NR 7A R 8A , N=S(O) p R 9A R 10A , C(O)R 11A , C(O)OR 12A , C(O)NR 13A R 14A , S(O)NR 15A R 16A , N.R. 17A S(O)2R 18A , S(O) m R 19A , a cyano group, and a halogen atom. R 1A represents a C3-C6 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, C(O)R 20A , C(O)OR 21A , C(O)NR 22A R 23A , S(O)R 24A or a hydrogen atom, R 2A , R 4A , R 6A , R 7A , R 13A , R 15A , R 17A , and R 22A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 3A , R 8A , R 11A , R 14A , and R 16A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 5A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, NR 2A C(O)R 3A If R 2A and R 3A is R 2A and a nitrogen atom to which R 3A may be taken together with the carbon atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), NR 4A C(O)OR 5A If R 4A and R 5A is R 4A and a nitrogen atom to which R 5A may be bonded to together with the oxygen atom to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), NR 6A C(O)NR 7A R 8A If R 6A and R 7A is R 6A and a nitrogen atom to which R 7A may be taken together with the nitrogen atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), NR 6A C(O)NR 7A R 8A If R 7A and R 8A is R 7A and R 8A may be taken together with the nitrogen atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), C(O)NR 13A R 14A If R 13A and R 14A is R 13A and R 14A may be taken together with the nitrogen atom to which it is bonded to form a 5- or 6-membered non-aromatic heterocycle optionally substituted with a C1-C3 chain hydrocarbon group (the C1-C3 chain hydrocarbon group may be substituted with one or more halogen atoms), p represents 0 or 1; R 9A and R 10A are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, R 12A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R 18A and R 19A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group C, or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, m represents 0, 1, or 2; R 20A represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, or a hydrogen atom; R 21A , R 23A , and R 24A are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a phenyl group optionally substituted with one or more substituents selected from group C. Group B: a cyclopropyl group, a phenyl group optionally substituted with one or more substituents selected from Group C, OR 3B , a cyano group, and a halogen atom. R 3B represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. Group C: a group consisting of C1-C6 chain hydrocarbon groups (the C1-C6 chain hydrocarbon groups may be substituted with one or more substituents selected from the group consisting of cyano groups and halogen atoms), C3-C6 cycloalkyl groups (the C3-C6 cycloalkyl groups may be substituted with one or more substituents selected from the group consisting of cyano groups and halogen atoms), C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, cyano groups, and halogen atoms. or an N-oxide thereof, or a salt thereof. In formula (I), R b11 is a C1-C3 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C3 alkoxy group optionally substituted with one or more halogen atoms, a cyclopropyl group, a halogen atom, or a hydrogen atom, or an N-oxide thereof according to claim 1, or a salt thereof. In formula (I), R ２ is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazolyl group, the thiazolyl group, the isothiazolyl group, the oxazolyl group, the isoxazolyl group, the 1,2,4-oxadiazolyl group, the 1,3,4- an oxadiazolyl group, the 1,2,4-thiadiazolyl group, the 1,3,4-thiadiazolyl group, the 1,2,3-triazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group may be substituted with one or more substituents selected from Group A}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4, 2. The compound according to claim 1, or an N-oxide thereof, or a salt thereof. In formula (I), R ２ is a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a 1,2,4-oxadiazolyl group, a 1,3,4-oxadiazolyl group, a 1,2,4-thiadiazolyl group, a 1,3,4-thiadiazolyl group, a 1,2,3-triazolyl group, a 1,2,4-triazolyl group, a tetrazolyl group {the phenyl group, the pyridyl group, the pyrimidinyl group, the pyridazinyl group, the pyrazolyl group, the thiazolyl group, the isothiazolyl group, the oxazolyl group, the isoxazolyl group, the 1,2,4-oxadiazolyl group, the 1,3,4- an oxadiazolyl group, the 1,2,4-thiadiazolyl group, the 1,3,4-thiadiazolyl group, the 1,2,3-triazolyl group, the 1,2,4-triazolyl group, and the tetrazolyl group may be substituted with one or more substituents selected from Group A}, an imidazolopyrimidinyl group, a triazolopyrimidinyl group {the imidazolopyrimidinyl group and the triazolopyrimidinyl group may be substituted with one or more substituents selected from the group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and a halogen atom}, a group represented by formula A1, a group represented by formula A2, a group represented by formula A3, or a group represented by formula A4, 3. The compound according to claim 2, or an N-oxide thereof, or a salt thereof. In formula (I), R １ is a methyl group, Q is a group represented by formula B1 or a group represented by formula B2, R b11 is a C1-C3 chain hydrocarbon group, a methoxy group, a cyclopropyl group, a halogen atom, NR ba1 C(O)R ba2 , N.R. ba3 C(O)OR ba4 , N.R. ba5 R ba6 , C(O)NR ba7 R ba8 , S.R. ba10 or a hydrogen atom, R ba1 But C(O)R ba11 and R ba2 , R ba8 , R ba10 , and R ba11 is a methyl group, R ba3 , R ba5 , and R ba7 is a hydrogen atom, R ba6 is a methyl group or a hydrogen atom, R ba4 is a C1-C4 chain hydrocarbon group, R b21 , and R b22 is a hydrogen atom, R ３ is a methyl group, an ethyl group, or a hydrogen atom, Z 1 is an oxygen atom, X is a group represented by formula C1-1 or a group represented by formula C2-1 (# 4 is Z 1 represents the bonding site with the carbon atom bonded to Z 2 is a sulfur atom or an oxygen atom, Z 3 is a nitrogen atom or CH, Z 4 , Z 5 , Z 6 and Z 7 The combination of Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 is a combination in which R c21 is a hydrogen atom, R c22 , and R c24 are the same or different and are a halogen atom or a hydrogen atom, R c23 is a C1-C4 chain hydrocarbon group (the C1-C4 chain hydrocarbon group may be substituted with one or more halogen atoms), a cyano group, a halogen atom, or a hydrogen atom; R c13 is a C1-C4 chain hydrocarbon group (the C1-C4 chain hydrocarbon group may be substituted with one or more halogen atoms), a cyclopropyl group, or a hydrogen atom; R c15 , and R c25 are the same or different and are C1-C3 chain hydrocarbon groups (the C1-C3 chain hydrocarbon groups may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, a phenyl group, and a halogen atom), When Q is a group represented by formula B1, R ２ a pyrimidinyl group {the pyrimidinyl group is a C1-C4 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C4 alkoxy group optionally substituted with one or more halogen atoms, an NR 2A C(O)R 3A , N.R. 4A C(O)OR 5A , C(O)NR 13A R 14A , a cyano group, and a halogen atom}, a pyridyl group {the pyridyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a pyridazinyl group {the pyridazinyl group is selected from the group consisting of a methyl group, a methoxy group, and a C(O)NR 33A R 34A and optionally substituted with one or more substituents selected from the group consisting of a pyrazinyl group, a thiazolyl group {the thiazolyl group is C(O)OR 12A , C(O)NR 43A R 44A and a cyano group}, a phenyl group {the phenyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, R a11 and R a33 is a hydrogen atom, R a21 and R a23 is a hydrogen atom, R a31 and R a53 are the same or different and are a methyl group or an ethyl group, R 2A is a methyl group or a hydrogen atom, R 3A is a methyl group or a cyclopropyl group, R 4A , R 13A , R 33A and R 43A is a hydrogen atom, R 5A , R 12A , R 34A and R 44A is a methyl group, R 14A is a methyl group or a hydrogen atom, When Q is a group represented by formula B2, R ２ is a pyrimidinyl group or a 1,2,3-triazolyl group; 2. The compound according to claim 1, or an N-oxide thereof, or a salt thereof. In formula (I), R １ is a methyl group, R ２ a pyrimidinyl group, a pyridyl group (the pyrimidinyl group and the pyridyl group are C(O)NR 13A R 14A , a cyano group, and a halogen atom}, a group represented by formula A1, or a group represented by formula A3, R a11 and R a33 is a hydrogen atom, R a21 and R a23 is a hydrogen atom, R a31 and R a53 are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more substituents selected from the group consisting of cyclopropyl groups and halogen atoms, R ３ is a methyl group or a hydrogen atom, Q is a group represented by formula B1 or a group represented by formula B2, R b11 , R b21 , and R b22 is a hydrogen atom, Z 1 is an oxygen atom, X is a group represented by formula C1-1, a group represented by formula C2-1, or a group represented by formula C3-1 (# 4 is Z 1 represents the bonding site with the carbon atom bonded to Z 2 is a sulfur atom or an oxygen atom, Z 3 is a nitrogen atom or CH, Z 4 , Z 5 , Z 6 and Z 7 The combination of Z 4 is CR C21 and Z 5 is CR C22 and Z 6 is CR C23 and Z 7 is CR C24 is a combination in which R c21 , R c31 , R c24 , and R c34 is a hydrogen atom, R c22 , R c32 , R c13 , R c23 , and R c35 are the same or different and are a C1-C6 chain hydrocarbon group, a cyclopropyl group (the C1-C6 chain hydrocarbon group and the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom), OR cc6 , a cyano group, a halogen atom, or a hydrogen atom; R c15 , R c25 , and R c33 are the same or different and are a C1-C6 chain hydrocarbon group (the C1-C6 chain hydrocarbon group may be substituted with one or more substituents selected from the group consisting of a cyclopropyl group, a cyano group, and a halogen atom) or a cyclopropyl group (the cyclopropyl group may be substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom).

3. The compound according to claim 2, or an N-oxide thereof, or a salt thereof. Formula (II) [During the ceremony, X A1 and X A2 are the same or different and represent a fluorine atom, a chlorine atom, or a hydrogen atom; Z A3 represents a nitrogen atom or CH. A compound represented by the formula: or a salt thereof. Formula (III) [During the ceremony, X C1 represents a halogen atom, a trifluoromethyl group, or a difluoromethyl group; X C2 represents a fluorine atom, a chlorine atom, or a hydrogen atom. A compound represented by the formula: or a salt thereof. Formula (IV) [During the ceremony, X D1 represents a C1-C4 chain hydrocarbon group or a cyclopropyl group; X D2 represents a fluorine atom, a chlorine atom, or a hydrogen atom; Z D3 represents a nitrogen atom or CH. A compound represented by the formula: or a salt thereof.

7. A composition for controlling arthropod pests, comprising the compound according to claim 1, an N-oxide thereof, or a salt thereof, and an inert carrier. A composition comprising one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and the compound according to any one of claims 1 to 6, or an N-oxide thereof, or a salt thereof: Group (a): A group consisting of insecticidal active ingredients, acaricidal active ingredients, and nematicidal active ingredients; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): repellent ingredients. 　 A method for controlling arthropod pests, comprising applying an effective amount of the compound according to any one of claims 1 to 6, its N-oxide, or a salt thereof, or an effective amount of the composition according to claim 11 to arthropod pests or a habitat of arthropod pests. 　 A seed or vegetative reproductive organ carrying an effective amount of the compound or N-oxide or salt thereof according to any one of claims 1 to 6, or an effective amount of the composition according to claim 11.

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