Heterocyclic compound and arthropod pest control composition containing same

Abstract

Provided is a compound which has an excellent controlling effect on arthropod pests. A compound represented by the formula (wherein the symbols have the meanings set forth in the description) or an N-oxide thereof has an excellent controlling effect on arthropod pests.

Description

Heterocyclic compound and pest control composition containing the same

[0001] The present invention relates to a heterocyclic compound and a composition for controlling arthropod pests 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. 2016 / 129684

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

[0005] The present invention is as follows: [1] A compound represented by formula (I)

[0006] [wherein Q represented by the following formula

[0007] represents a group represented by formula Q1, a group represented by formula Q2, a group represented by formula Q3, a group represented by formula Q4, a group represented by formula Q5, a group represented by formula Q6, or a group represented by formula Q7 (# represents a bonding site to a sulfur atom, and ● represents a bonding site to Het),

[0008]

[0009] A 1 is a nitrogen atom or CR 1 represents R 1 represents a halogen atom or a hydrogen atom; 1 is a nitrogen atom or CR 10a represents 2 is a nitrogen atom or CR 10b represents 3 is a nitrogen atom or CR 10c represents 4 is a nitrogen atom or CR 10d represents 5 is a nitrogen atom or CR 10e represents 6 is a nitrogen atom or CR 10f represents 7is a nitrogen atom or CR 10g n represents 0, 1 or 2; R 2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, a cyclopropylmethyl group, or NR 5 R 6 represents R 5 and R 6 are the same or different and represent a C1-C6 alkyl 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, or 5 and R 6 may together with the nitrogen atom to which they are attached form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, or a piperidyl group; Y 1 is NR 7 , an oxygen atom, or a sulfur atom; R 7 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from group H}, R 3a , R 3b , R 3d , R 10a , R 10b , R 10c , R 10d , R 10e , R 10f and R 10g are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, OR 12 , N.R. 11 R 12 , N.R. 18 R 19 , N.R. 24 NR 11 R 12 , N.R. 24 OR 11 , N.R. 11C(O)R 13 , N.R. 24 NR 11 C(O)R 13 , N.R. 11 C(O)OR 14 , N.R. 24 NR 11 C(O)OR 14 , N.R. 11 C(O)NR 31 R 32 , N.R. 24 NR 11 C(O)NR 31 R 32 , N=CHNR 31 R 32 , N=S(O) p R 15 R 16 , C(O)R 13 , C(O)OR 17 , C(O)NR 31 R 32 , C(O)NR 11 S(O)2R 23 , C.R. 30 = NOR 17 , N.R. 11 CR 24 = NOR 17 , S(O) q R 23 , a cyano group, a nitro group, a hydrogen atom, or a halogen atom; R 3a , R 3b , and R 3dtwo adjacent substituents among the following may, together with the two carbon atoms to which they are bonded, form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyrrole ring, the furan ring, the thiophene ring, the pyrazole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the isothiazole ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring are optionally substituted with one or more substituents selected from Group H} or a triazole ring optionally substituted with one or more substituents selected from Group I, p represents 0 or 1, q represents 0, 1 or 2, R 11 , R 24 , R 36 , and R 37 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 12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group J, a phenyl group optionally substituted with one or more substituents selected from Group D, a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, a hydrogen atom, or S(O)R 23 represents R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, or a hydrogen atom; R 14represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group (the phenyl moiety in the phenyl C1-C3 alkyl group optionally substituted with one or more substituents selected from Group D), R 15 and R 16 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms; R 17 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 D, or a hydrogen atom; R 18 and R 19 R together with the nitrogen atom to which they are bonded represent a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E; 23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from Group D, R 30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 35 , N.R. 36 R 37 or a hydrogen atom, R 31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, S(O)R 23 or a hydrogen atom, R 32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group J, or a hydrogen atom; R 35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, Het represents a group represented by formula Het1, a group represented by formula Het2, or a group represented by formula Het3 (# 1 represents the binding site to Q),

[0010] B 1 is NR 51a , or CR 61a R 61b represents B 2 is NR 51b , C.R. 61c R 61d , C.R. 61e R 61f -CR 61g R 61h -*, NR 51c -CR 61i R 61j - *, CR 61k R 61m -CR 61n R 61p -CR 61q R 61r -* or NR 51d -CR 61s R 61t -CR 61u R 61v - represents *, * represents B 1 represents the bonding position with W 1 represents an oxygen atom or a sulfur atom, R 51a , R 51b , R 51c , and R 51d are the same or different, and the group K 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 61a , R 61b , R 61c , R 61d , R 61e , R 61f , R 61g , R 61h , R 61i , R 61j , R 61k , R 61 , R 61m , R 61n , R 61p , R 61q , R61r , R 61s , R 61t , R 61u , and R 61v are the same or different and are each a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a nitro group, OR 63 , N.R. 63 R 64 , a cyano group, a halogen atom, or a hydrogen atom; R 61a and R 61b , R 61c and R 61d , R 61e and R 61f , R 61g and R 61h , R 61i and R 61j , R 61k and R 61m , R 61n and R 61p , R 61q and R 61r , R 61s and R 61t , and R 61u and R 61v may each be taken together with the carbon atom to which they are attached to form a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom; R 63 is the group T 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group J 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 R represents a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of , 64represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; X 1 is CR 62a or a nitrogen atom, X 2 is CR 62b or a nitrogen atom, X 3 is CR 62c or a nitrogen atom; Z 1 is NR 52a , an oxygen atom, or a sulfur atom; Z 2 is NR 52b , an oxygen atom, or a sulfur atom; Z 3 is NR 52c , an oxygen atom, or a sulfur atom; R 52a , R 52b , and R 52c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 73 , C(O)OR 74 , C(O)NR 91 R 92 , C(O)NR 71 S(O)2R 83 , C.R. 90 = NOR 77 , S(O) v R 83 or a hydrogen atom, R 62a , R 62b , and R 62c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 72 , N.R. 71 R 72 , N.R. 76a R 76b , N.R. 84 NR 71 R 72 , N.R. 84 OR 71 , N.R. 71 C(O)R 73 , N.R. 84 NR 71 C(O)R 73 , N.R. 71 C(O)OR 74 , N.R. 84 NR 71 C(O)OR 74 , N.R. 71 C(O)NR 91 R 92 , N.R. 84 NR 71 C(O)NR 91 R 92 , N=CHNR 91 R 92 , N=S(O) r R 75 R 76 , C(O)R 73 , C(O)OR 77 , C(O)NR 91 R 92 , C(O)NR 71 S(O)2R 83 , C.R. 90 = NOR 77 , N.R. 71 CR 84 = NOR 77 , S(O) t R 83 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; r represents 0 or 1; t represents 0, 1, or 2; v represents 0, 1, or 2; R 71 , R 84 , R 96 and R 97 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 72 is the group P 2a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of S(O)R 83 or a hydrogen atom, R 73 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: 74 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of: 75 and R 76 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms; R 76a and R 76b together with the nitrogen atom to which they are attached, form the group P 2 R 77 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of: 83 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group V 2R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of 90 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 95 , N.R. 96 R 97 or a hydrogen atom, R 91 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 92 is the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O)R 83 or a hydrogen atom. 95 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms. Group D: a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, NR 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 , a cyano group, a nitro group, and a halogen atom. 101 and R 102are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group. Group F: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of NR 101 R 102 Group H: a C1-C6 alkyl group optionally substituted with one or more halogen atoms; 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 104 , N.R. 103 R 104 , C(O)R 104 , C(O)NR 103 R 104 , O.C.(O.)R 103 , OC(O)OR 103 , N.R. 104 C(O)R 103 , N.R. 104 C(O)OR 103 , C(O)OR 104 , a halogen atom, a nitro group, a cyano group, and an amino group. 103 represents 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 104represents a C1-C6 alkyl 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. Group I: 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, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 103 , C(O)OR 103 , and C(O)NR 103 R 104 Group J: a group consisting of C1-C6 alkyl groups optionally substituted with one or more halogen atoms, halogen atoms, and cyano groups. Group L: a group consisting of C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, cyano groups, hydroxy groups, and halogen atoms. Group J 2 Group K: A group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms, and a group M 3 Group M consists of 3- to 7-membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from the following: 2Group T: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, and a halogen atom. 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of an amino group, NHR 101 , N.R. 101 R 102 , a halogen atom, and a cyano group. 2 : Group U 3 Group U is a group consisting of a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, a phenyl group, and a halogen atom. 3 Group V: A group consisting of C1-C3 alkyl groups and halogen atoms. 2Group D: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl)amino group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. 3 : a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, an amino group, NHR 101 , N.R. 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 a group consisting of a cyano group, a nitro group, and a halogen atom; 3a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C2 alkynyloxy group optionally substituted with one or more halogen atoms, and a halogen atom.] (hereinafter referred to as compound N of the present invention) or an N-oxide thereof (hereinafter, a compound represented by formula (I) or an N-oxide thereof will be referred to as compound of the present invention). [2] A compound according to [1] or an N-oxide thereof, wherein Q is a group represented by formula Q1. [3] A compound according to [1] or an N-oxide thereof, wherein Q is a group represented by formula Q5. [4] A compound according to [1] or an N-oxide thereof, wherein Q is a group represented by formula Q1, and A 1 [5] The compound according to [1], wherein Q is a group represented by formula Q5, and G is an N-oxide thereof. 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is a nitrogen atom or CR 10d [6] The compound according to [1] or an N-oxide thereof, wherein Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d [7] The compound according to [1] or an N-oxide thereof, wherein Het is a group represented by the formula Het1, and B 1 is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1 [8] The compound according to any one of [1] to [6], wherein Het is a group represented by the formula Het2, and B is an N-oxide thereof. 1is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1 [9] The compound according to any one of [1] to [6], wherein Het is a group represented by the formula Het3, and B is an N-oxide thereof. 1 is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1

[10] The compound or N-oxide thereof according to any one of [1] to [6], wherein R is an oxygen atom. 2 is an ethyl group, and W 1 is an oxygen atom.

[11] A composition for controlling arthropod pests, comprising the compound or N-oxide thereof according to any one of [1] to

[10] and an inert carrier.

[12] A composition comprising one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the compound or N-oxide thereof according to any one of [1] to

[10] : Group (a): a group consisting of insecticidal active components, acaricidal active components, and nematicidal active components; Group (b): fungicidal active components; Group (c): plant growth regulator components; Group (d): repellent components.

[13] A method for controlling arthropod pests, comprising applying an effective amount of the compound or N-oxide thereof according to any one of [1] to

[10] or an effective amount of the composition according to

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

[14] A seed or a vegetative reproductive organ carrying an effective amount of the compound or N-oxide thereof according to any one of [1] to

[10] , or an effective amount of the composition according to

[12] .

[0011] According to the present invention, arthropod pests can be controlled.

[0012] The substituents of the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent is substituted with two or more halogen atoms or substituents, these halogen atoms or substituents may be the same or different. In this specification, the expression "optionally substituted with one or more substituents selected from group X" means that when two or more substituents selected from group X are present, these substituents may be the same or different. In this specification, the expression "CX-CY" means that the number of carbon atoms is X to Y. For example, the expression "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 alkenyloxy groups include 2-propenyloxy groups, 2-butenyloxy groups, and 5-hexenyloxy groups. Examples of alkynyloxy groups include 2-propynyloxy groups, 2-butynyloxy groups, and 5-hexynyloxy groups.

[0013] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. Examples of cycloalkenyl groups include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups.

[0014] Examples of the 3- to 7-membered non-aromatic heterocyclic group include an aziridinyl group, an oxiranyl group, a thiiranyl group, an azetidinyl group, an oxetanyl group, a thietanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a piperidyl group, a pyranyl group, a dihydropyranyl group, a tetrahydropyranyl group, a tetrahydrothiopyranyl group, an azepanyl group, an oxepanyl group, a thiepanyl group, a pyrazolinyl group, a pyrazolidinyl group, an imidazolinyl group, an imidazolidinyl group, an oxazolinyl group, a thiazolinyl group, an oxazolidinyl group, a thiazolidinyl group, an isoxazolinyl group, an isoxazolidinyl group, an isothiazolinyl group, an isothiazolidinyl group, a dioxolyl group, a dioxolanyl group, a dioxanyl group, a morpholinyl group, a thiomorpholinyl group, and a piperazinyl group. Group X (where X is E, P 2 , and M 3 Examples of the 3- to 7-membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from the group consisting of:

[0015]

[0016] Examples of 5- or 6-membered aromatic heterocyclic groups include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl groups. Examples of 6-membered aromatic heterocyclic groups include pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl groups. Examples of (C3-C6 cycloalkyl)C1-C3 alkyl groups optionally substituted with one or more halogen atoms include cyclopropylmethyl, (2-fluorocyclopropyl)methyl, cyclopropyl(fluoro)methyl, and (2-fluorocyclopropyl)(fluoro)methyl groups. The (C3-C7 cycloalkyl)C1-C6 alkyl group optionally substituted with one or more halogen atoms refers to a group in which a (C3-C7 cycloalkyl) and / or a (C1-C6 alkyl) is optionally substituted with one or more halogen atoms, and examples thereof include a (2,2-difluorocyclopropyl)methyl group, a 2-cyclopropyl-1,1,2,2-tetrafluoroethyl group, a 2-(2,2-difluorocyclopropyl)-1,1,2,2-tetrafluoroethyl group, a (2,2-difluorocyclopropyl)propyl group, a (2,2-difluorocyclopropyl)butyl group, a (2,2-difluorocyclopropyl)pentyl group, and a (2,2-difluorocyclopropyl)hexyl group. Examples of the phenyl C1-C3 alkyl group (the phenyl moiety in the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from Group D) include a benzyl group, a 2-fluorobenzyl group, a 4-chlorobenzyl group, a 4-(trifluoromethyl)benzyl group, and a 2-[4-(trifluoromethyl)phenyl]ethyl group. Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group.Examples of alkylsulfinyl groups include methylsulfinyl groups, ethylsulfinyl groups, propylsulfinyl groups, and isopropylsulfinyl groups. Examples of alkylsulfonyl groups include methylsulfonyl groups, ethylsulfonyl groups, propylsulfonyl groups, and isopropylsulfonyl groups. Examples of alkylcarbonyl groups include acetyl groups, propanoyl groups, 2-methylpropanoyl groups, and hexanoyl groups. Examples of alkoxycarbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, isopropoxycarbonyl groups, and pentyloxycarbonyl groups.

[0017] Examples of the N-oxide of the compound of formula (I) include the compounds of the following formula:

[0018] (wherein the symbols have the same meanings as defined above.)

[0019] 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.

[0020] The compound of the present invention may form an acid addition salt. Examples of acids that form acid addition salts include inorganic acids such as hydrogen chloride, phosphoric acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, benzoic acid, and p-toluenesulfonic acid. The acid addition salt can be obtained by mixing the compound of the present invention with an acid.

[0021] The groups represented by formulae Het11 to Het17, Het21 to Het25, and Het31 to Het37 respectively mean the groups shown in [Table E1].

[0022]

[0023] The embodiments of the compound N of the present invention include the following compounds. [Embodiment 1] A compound of the present invention, in which n is 0. [Embodiment 2] A compound of the present invention, in which n is 1. [Embodiment 3] A compound of the present invention, in which n is 2. [Embodiment 4] A compound of the present invention, in which R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. 2 is a cyclopropyl group. [Embodiment 6] In the compound N of the present invention, R 2 is a cyclopropylmethyl group. [Embodiment 7] In the compound N of the present invention, R 2 NR 5 R 6 [Embodiment 8] In the compound N of the present invention, R 2 is an ethyl group. [Aspect 9] A compound of the present invention, wherein Q is a group represented by formula Q1. [Aspect 10] A compound of the present invention, wherein Q is a group represented by formula Q2. [Aspect 11] A compound of the present invention, wherein Q is a group represented by formula Q3. [Aspect 12] A compound of the present invention, wherein Q is a group represented by formula Q4. [Aspect 13] A compound of the present invention, wherein Q is a group represented by formula Q5. [Aspect 14] A compound of the present invention, wherein Q is a group represented by formula Q6. [Aspect 15] A compound of the present invention, wherein Q is a group represented by formula Q7. [Aspect 16] A compound of the present invention, wherein Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect 17] A compound of the present invention, wherein Q is a group represented by formula Q1, a group represented by formula Q2, a group represented by formula Q3, or a group represented by formula Q4. [Aspect 18] A compound of the present invention N, in which Q is a group represented by formula Q5, a group represented by formula Q6, or a group represented by formula Q7. [Aspect 19] A compound of the present invention N, in which Q is a group represented by formula Q1, and A 1 A compound in which Q is a group represented by the formula Q1, and A is a nitrogen atom. 1 is CR 1 [Embodiment 21] In the compound N of the present invention, Q is a group represented by the formula Q1, and A1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom. [Embodiment 22] In the compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group L. [Embodiment 23] A compound of the present invention, wherein Q is a group represented by formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group E. [Embodiment 24] In compound N of the present invention, Q is a group represented by formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a phenyl group optionally substituted with one or more substituents selected from group H. [Embodiment 25] A compound N of the present invention, wherein Q is a group represented by formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H. [Embodiment 26] A compound of the present invention, wherein Q is a group represented by formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a halogen atom. [Embodiment 27] In the compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a , R 3b and R 3d is a hydrogen atom. [Embodiment 28] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2is CR 10b and G 3 is CR 10c and G 4 is CR 10d [Embodiment 29] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is a nitrogen atom. [Embodiment 30] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom. [Embodiment 31] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group L. [Embodiment 32] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10bis a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group E. [Embodiment 33] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a phenyl group optionally substituted with one or more substituents selected from group H. [Embodiment 34] A compound N of the present invention, wherein Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H. [Embodiment 35] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a halogen atom. [Embodiment 36] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G4 is CR 10d and R 10a , R 10b , R 10c and R 10d is a hydrogen atom. [Embodiment 37] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom. [Embodiment 38] In the compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group L. [Embodiment 39] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group E. [Embodiment 40] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10band G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a phenyl group optionally substituted with one or more substituents selected from group H. [Embodiment 41] A compound N of the present invention, wherein Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group H. [Embodiment 42] In compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a halogen atom. 2 is an ethyl group. [Aspect 44] In aspect 10, R 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group.2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. 2 is an ethyl group. [Embodiment 77] In the compound N of the present invention, W 1 is an oxygen atom. [Embodiment 78] In the compound N of the present invention, B 1 is CR 61a R 61b and B 2 is CR 61c R 61d [Aspect 79] A compound of the present invention, wherein Het is a group represented by formula Het1. [Aspect 80] A compound of the present invention, wherein Het is a group represented by formula Het2. [Aspect 81] A compound of the present invention, wherein Het is a group represented by formula Het3. [Aspect 82] A compound of the present invention, wherein Het is a group represented by any one of formulas Het11 to Het17, Het21 to Het25, and Het31 to Het37. [Aspect 83] A compound of the present invention, wherein Het is a group represented by formula Het11. [Aspect 84] A compound of the present invention, wherein Het is a group represented by formula Het12. [Aspect 85] A compound of the present invention, wherein Het is a group represented by formula Het13. [Aspect 86] A compound of the present invention, wherein Het is a group represented by formula Het16. [Aspect 87] A compound of the present invention, wherein Het is a group represented by formula Het21 in compound N. [Aspect 88] A compound of the present invention, wherein Het is a group represented by formula Het24 in compound N. [Aspect 89] A compound of the present invention, wherein Het is a group represented by formula Het31 in compound N. [Aspect 90] A compound of the present invention, wherein Het is a group represented by formula Het33 in compound N. [Aspect 91] A compound of the present invention, wherein Het is a group represented by formula Het34 in compound N. [Aspect 92] A compound of the present invention, wherein Het is a group represented by formula Het36 in compound N. [Aspect 93] A compound of the present invention, wherein Het is a group represented by formula Het16, and R 62b But group P2 [Embodiment 94] In compound N of the present invention, Het is a group represented by the formula Het16, and R 62b But group M 2 A compound of the present invention, wherein Het is a group represented by the formula Het16, and R 62b But group V 2 [Embodiment 96] In the compound N of the present invention, Het is a group represented by the formula Het16, and R 62b But group V 2 [Embodiment 97] In the compound N of the present invention, Het is a group represented by the formula Het16, and R 62b is a halogen atom. [Embodiment 98] In the compound N of the present invention, Het is a group represented by the formula Het16, and R 62b is a hydrogen atom. [Embodiment 99] In the compound N of the present invention, Het is a group represented by the formula Het24, and R 52b But group P 2 A compound of the present invention, wherein Het is a group represented by the formula Het24, and R 52b But group M 2 A compound of the present invention, wherein Het is a group represented by the formula Het24, and R 52b But group V 2 [Embodiment 102] In the compound N of the present invention, Het is a group represented by the formula Het24, and R 52b But group V 2[Embodiment 103] In compound N of the present invention, Het is a group represented by the formula Het24, and R 52b is a hydrogen atom. [Embodiment 104] In the compound N of the present invention, Het is a group represented by the formula Het24, and R 52b But group P 2 A compound of the present invention, wherein Het is a group represented by the formula Het34, and R 52c But group M 2 A compound of the present invention, wherein Het is a group represented by the formula Het34, and R 52c But group V 2 [Embodiment 107] In compound N of the present invention, Het is a group represented by the formula Het34, and R 52c But group V 2 [Embodiment 108] In compound N of the present invention, Het is a group represented by the formula Het34, and R 52cis a hydrogen atom. [Aspect 109] A compound in Aspect 79, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 110] A compound in Aspect 80, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 111] A compound in Aspect 81, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 112] A compound in Aspect 82, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 113] A compound in Aspect 83, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 114] A compound in Aspect 84, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 115] A compound in Aspect 85, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 116] A compound in Aspect 86, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 117] A compound in Aspect 87, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 118] A compound in Aspect 88, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 119] A compound in Aspect 89, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 120] A compound in Aspect 90, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 121] A compound in Aspect 91, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 122] A compound in Aspect 92, wherein Q is a group represented by formula Q1 or a group represented by Q5. [Aspect 123] A compound N of the present invention, wherein Het is a group represented by formula Het16, Q is a group represented by formula Q1, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 124] In compound N of the present invention, Het is a group represented by the formula Het24, Q is a group represented by the formula Q1, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 125] In compound N of the present invention, Het is a group represented by the formula Het34, Q is a group represented by the formula Q1, and R 2is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 126] A compound N of the present invention, wherein Het is a group represented by the formula Het16, Q is a group represented by the formula Q5, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 127] A compound N of the present invention, wherein Het is a group represented by the formula Het24, Q is a group represented by the formula Q5, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 128] A compound N of the present invention, wherein Het is a group represented by the formula Het34, Q is a group represented by the formula Q5, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms. [Embodiment 129] A compound of the present invention, wherein Het is a group represented by the formula Het16, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment 130] In the compound N of the present invention, Het is a group represented by the formula Het24, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment 131] In the compound N of the present invention, Het is a group represented by the formula Het34, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, and R 3a and R 3d is hydrogen. 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, and R 3a and R 3d is hydrogen. 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, and R 3a and R 3d is hydrogen.

[0024] [Aspect C1] In the compound N of the present invention, B 1is CR 61a R 61b and B 2 is CR 61c R 61d and R 61a , R 61b , R 61c and R 61d is a hydrogen atom, and W 1 is an oxygen atom. [Aspect C2] In the compound N of the present invention, Z 1 is a sulfur atom, and Z 2 NR 52b and Z 3 NR 52c [Aspect C3] In aspect C1, Z 1 is a sulfur atom, and Z 2 NR 52b and Z 3 NR 52c [Aspect C4] In aspect C2, the compound 52b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 [Aspect C5] A compound in which R is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of cycloalkyl groups, or a hydrogen atom. 52b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 [Aspect C6] A compound in which R is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of cycloalkyl groups, or a hydrogen atom. 52b is group S 1 [Aspect C7] A compound in which R is a cyclopropyl group optionally substituted with one or more substituents selected from the group consisting of cyclopropyl, ... 52b is group S 1 [Aspect C8] A compound in which R is a cyclopropyl group optionally substituted with one or more substituents selected from the group consisting of cyclopropyl, ... 52b is a cyclopropyl group or a hydrogen atom. [Aspect C9] A compound in Aspect C3, wherein R 52b is a cyclopropyl group or a hydrogen atom. [Aspect C10] In compound N of the present invention, X 1 is CR62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. 1 A group consisting of a halogen atom, a phenyl group, and a cyano group. [Aspect C11] In the compound N of the present invention, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C12] In the compound N of the present invention, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C13] In the compound N of the present invention, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C14] In the compound N of the present invention, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3is a nitrogen atom. [Aspect C15] In the compound N of the present invention, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C16] In the compound N of the present invention, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C17] In the compound N of the present invention, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C18] In Aspect C1, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C19] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C20] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C21] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C22] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C23] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C24] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C25] A compound according to Aspect C1, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C26] In Aspect C2, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X3 is a nitrogen atom. [Aspect C27] In Aspect C2, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C28] In Aspect C2, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C29] In Aspect C2, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C30] In Aspect C2, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C31] A compound according to Aspect C2, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C32] In Aspect C2, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X3 is a nitrogen atom. [Aspect C33] In Aspect C2, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C34] In Aspect C3, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C35] In Aspect C3, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C36] In Aspect C3, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C37] In Aspect C3, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C38] In Aspect C3, X1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C39] In Aspect C3, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C40] A compound according to Aspect C3, wherein X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C41] A compound according to Aspect C3, wherein X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C42] In Aspect C4, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C43] In Aspect C4, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3is a nitrogen atom. [Aspect C44] In Aspect C4, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C45] In Aspect C4, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C46] In Aspect C4, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C47] In Aspect C4, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C48] In Aspect C4, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C49] In Aspect C4, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C50] In Aspect C5, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62ba C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C51] In Aspect C5, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C52] In Aspect C5, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C53] In Aspect C5, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C54] In Aspect C5, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C55] In Aspect C5, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3is a nitrogen atom. [Aspect C56] In Aspect C5, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C57] In Aspect C5, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C58] In Aspect C6, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C59] In Aspect C6, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C60] In Aspect C6, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C61] In Aspect C6, X 1 is CR 62a and R 62a is a hydrogen atom, and R62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C62] In Aspect C6, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C63] In Aspect C6, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C64] In Aspect C6, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C65] In Aspect C6, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C66] In Aspect C7, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C67] In Aspect C7, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms;1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C68] In Aspect C7, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C69] In Aspect C7, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C70] In Aspect C7, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C71] In Aspect C7, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C72] In Aspect C7, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C73] In Aspect C7, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3is a nitrogen atom. [Aspect C74] In Aspect C8, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C75] In Aspect C8, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C76] In Aspect C8, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C77] In Aspect C8, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C78] In Aspect C8, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C79] In Aspect C8, X1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C80] In Aspect C8, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C81] In Aspect C8, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C82] In Aspect C9, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C83] In Aspect C9, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; 1 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of OR 72 or a halogen atom, and X 3 is a nitrogen atom. [Aspect C84] In Aspect C9, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group3 is a nitrogen atom. [Aspect C85] In Aspect C9, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is group S 1 X is a cyclopropyl group or a halogen atom optionally substituted with one or more substituents selected from the group 3 is a nitrogen atom. [Aspect C86] In Aspect C9, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C87] In Aspect C9, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a cyclopropyl group or a halogen atom, and X 3 is a nitrogen atom. [Aspect C88] In Aspect C9, X 1 is CR 62a and R 62a is a halogen atom or a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C89] In Aspect C9, X 1 is CR 62a and R 62a is a hydrogen atom, and R 62b is a halogen atom, and X 3 is a nitrogen atom. [Aspect C90] In Aspect C10, X 2 is CR 62b [Aspect C91] In aspect C10, the compound 2 is a nitrogen atom. [Aspect C92] In Aspect C11, X 2 is CR 62b [Aspect C93] In aspect C11, the compound 2 is a nitrogen atom. [Aspect C94] In Aspect C12, X 2 is CR 62b[Aspect C95] In aspect C12, the compound 2 is a nitrogen atom. [Aspect C96] In Aspect C13, X 2 is CR 62b [Aspect C97] In aspect C13, the compound 2 is a nitrogen atom. [Aspect C98] In Aspect C14, X 2 is CR 62b [Aspect C99] In aspect C14, the compound 2 is a nitrogen atom. [Aspect C100] In Aspect C15, X 2 is CR 62b [Aspect C101] In Aspect C15, the compound is 2 is a nitrogen atom. [Aspect C102] In Aspect C16, X 2 is CR 62b [Aspect C103] In aspect C16, the compound 2 is a nitrogen atom. [Aspect C104] In Aspect C17, X 2 is CR 62b [Aspect C105] In aspect C17, the compound 2 is a nitrogen atom. [Aspect C106] In Aspect C18, X 2 is CR 62b [Aspect C107] In aspect C18, the compound 2 is a nitrogen atom. [Aspect C108] In Aspect C19, X 2 is CR 62b [Aspect C109] In aspect C19, the compound 2 is a nitrogen atom. [Aspect C110] A compound according to Aspect C20, wherein X 2 is CR 62b [Aspect C111] In aspect C20, the compound 2 is a nitrogen atom. [Aspect C112] In Aspect C21, X 2 is CR 62b [Aspect C113] In the aspect C21, the compound 2 is a nitrogen atom. [Aspect C114] In Aspect C22, X 2 is CR62b [Aspect C115] In aspect C22, the compound 2 is a nitrogen atom. [Aspect C116] In Aspect C23, X 2 is CR 62b [Aspect C117] In aspect C23, the compound 2 is a nitrogen atom. [Aspect C118] In Aspect C24, X 2 is CR 62b [Aspect C119] In aspect C24, the compound 2 is a nitrogen atom. [Aspect C120] In Aspect C25, X 2 is CR 62b [Aspect C121] In aspect C25, the compound 2 is a nitrogen atom. [Aspect C122] In Aspect C26, X 2 is CR 62b [Aspect C123] In aspect C26, the compound 2 is a nitrogen atom. [Aspect C124] In Aspect C27, X 2 is CR 62b [Aspect C125] In aspect C27, the compound 2 is a nitrogen atom. [Aspect C126] In Aspect C28, X 2 is CR 62b [Aspect C127] In aspect C28, the compound 2 is a nitrogen atom. [Aspect C128] In Aspect C29, X 2 is CR 62b [Aspect C129] In aspect C29, the compound is 2 is a nitrogen atom. [Aspect C130] In Aspect C30, X 2 is CR 62b [Aspect C131] In Aspect C30, the compound 2 is a nitrogen atom. [Aspect C132] In Aspect C31, X 2 is CR 62b [Aspect C133] In the aspect C31, X 2 is a nitrogen atom. [Aspect C134] In Aspect C32, X2 is CR 62b [Aspect C135] In aspect C32, the compound 2 is a nitrogen atom. [Aspect C136] In Aspect C33, X 2 is CR 62b [Aspect C137] In the aspect C33, X 2 is a nitrogen atom. [Aspect C138] In Aspect C34, X 2 is CR 62b [Aspect C139] In Aspect C34, the compound is 2 is a nitrogen atom. [Aspect C140] In Aspect C35, X 2 is CR 62b [Aspect C141] In Aspect C35, the compound is 2 is a nitrogen atom. [Aspect C142] In Aspect C36, X 2 is CR 62b [Aspect C143] In the aspect C36, X 2 is a nitrogen atom. [Aspect C144] In Aspect C37, X 2 is CR 62b [Aspect C145] In aspect C37, the compound 2 is a nitrogen atom. [Aspect C146] In Aspect C38, X 2 is CR 62b [Aspect C147] In aspect C38, the compound 2 is a nitrogen atom. [Aspect C148] In Aspect C39, X 2 is CR 62b [Aspect C149] In the aspect C39, the compound 2 is a nitrogen atom. [Aspect C150] In Aspect C40, X 2 is CR 62b [Aspect C151] In Aspect C40, the compound 2 is a nitrogen atom. [Aspect C152] In Aspect C41, X 2 is CR 62b [Aspect C153] In the aspect C41, X 2is a nitrogen atom. [Aspect C154] In Aspect C42, X 2 is CR 62b [Aspect C155] In aspect C42, the compound 2 is a nitrogen atom. [Aspect C156] In Aspect C43, X 2 is CR 62b [Aspect C157] In the aspect C43, X 2 is a nitrogen atom. [Aspect C158] In Aspect C44, X 2 is CR 62b [Aspect C159] In Aspect C44, the compound is 2 is a nitrogen atom. [Aspect C160] In Aspect C45, X 2 is CR 62b [Aspect C161] In aspect C45, the compound 2 is a nitrogen atom. [Aspect C162] In Aspect C46, ​​X 2 is CR 62b [Aspect C163] In the aspect C46, ​​X 2 is a nitrogen atom. [Aspect C164] In Aspect C47, X 2 is CR 62b [Aspect C165] In aspect C47, the compound 2 is a nitrogen atom. [Aspect C166] In Aspect C48, X 2 is CR 62b [Aspect C167] In aspect C48, the compound 2 is a nitrogen atom. [Aspect C168] In Aspect C49, X 2 is CR 62b [Aspect C169] In the aspect C49, X 2 is a nitrogen atom. [Aspect C170] A compound according to Aspect C50, wherein X 2 is CR 62b [Aspect C171] In aspect C50, the compound 2 is a nitrogen atom. [Aspect C172] In Aspect C51, X 2 is CR 62b [Aspect C173] In the aspect C51, X2 is a nitrogen atom. [Aspect C174] In Aspect C52, X 2 is CR 62b [Aspect C175] In aspect C52, the compound 2 is a nitrogen atom. [Aspect C176] In Aspect C53, X 2 is CR 62b [Aspect C177] In the aspect C53, X 2 is a nitrogen atom. [Aspect C178] In Aspect C54, X 2 is CR 62b [Aspect C179] In aspect C54, the compound is 2 is a nitrogen atom. [Aspect C180] A compound according to Aspect C55, wherein X 2 is CR 62b [Aspect C181] In Aspect C55, the compound is 2 is a nitrogen atom. [Aspect C182] In Aspect C56, X 2 is CR 62b [Aspect C183] In aspect C56, the compound is 2 is a nitrogen atom. [Aspect C184] In Aspect C57, X 2 is CR 62b [Aspect C185] In aspect C57, the compound 2 is a nitrogen atom. [Aspect C186] In Aspect C58, X 2 is CR 62b [Aspect C187] In aspect C58, the compound 2 is a nitrogen atom. [Aspect C188] In Aspect C59, X 2 is CR 62b [Aspect C189] In aspect C59, the compound is 2 is a nitrogen atom. [Aspect C190] A compound according to Aspect C60, wherein X 2 is CR 62b [Aspect C191] In Aspect C60, the compound 2 is a nitrogen atom. [Aspect C192] In Aspect C61, X 2 is CR 62b[Aspect C193] In the aspect C61, X 2 is a nitrogen atom. [Aspect C194] In Aspect C62, X 2 is CR 62b [Aspect C195] In aspect C62, the compound 2 is a nitrogen atom. [Aspect C196] In Aspect C63, X 2 is CR 62b [Aspect C197] In the aspect C63, X 2 is a nitrogen atom. [Aspect C198] In Aspect C64, X 2 is CR 62b [Aspect C199] In aspect C64, the compound 2 is a nitrogen atom. [Aspect C200] A compound according to Aspect C65, wherein X 2 is CR 62b [Aspect C201] In aspect C65, the compound is 2 is a nitrogen atom. [Aspect C202] In Aspect C66, X 2 is CR 62b [Aspect C203] In aspect C66, the compound is 2 is a nitrogen atom. [Aspect C204] In Aspect C67, X 2 is CR 62b [Aspect C205] In aspect C67, the compound is 2 is a nitrogen atom. [Aspect C206] In Aspect C68, X 2 is CR 62b [Aspect C207] In aspect C68, the compound is 2 is a nitrogen atom. [Aspect C208] In Aspect C69, X 2 is CR 62b [Aspect C209] In aspect C69, the compound is 2 is a nitrogen atom. [Aspect C210] A compound according to Aspect C70, wherein X 2 is CR 62b [Aspect C211] In the aspect C70, X 2 is a nitrogen atom. [Aspect C212] The compound according to Aspect C71, wherein X 2 is CR62b [Aspect C213] In the aspect C71, X 2 is a nitrogen atom. [Aspect C214] The compound according to Aspect C72, wherein X 2 is CR 62b [Aspect C215] In aspect C72, the compound 2 is a nitrogen atom. [Aspect C216] In Aspect C73, X 2 is CR 62b [Aspect C217] In aspect C73, the compound is 2 is a nitrogen atom. [Aspect C218] In Aspect C74, X 2 is CR 62b [Aspect C219] In aspect C74, the compound 2 is a nitrogen atom. [Aspect C220] In Aspect C75, X 2 is CR 62b [Aspect C221] In aspect C75, the compound is 2 is a nitrogen atom. [Aspect C222] In Aspect C76, X 2 is CR 62b [Aspect C223] In aspect C76, the compound is 2 is a nitrogen atom. [Aspect C224] In Aspect C77, X 2 is CR 62b [Aspect C225] In aspect C77, the compound 2 is a nitrogen atom. [Aspect C226] In Aspect C78, ​​X 2 is CR 62b [Aspect C227] In aspect C78, ​​the compound 2 is a nitrogen atom. [Aspect C228] In Aspect C79, X 2 is CR 62b [Aspect C229] In aspect C79, the compound is 2 is a nitrogen atom. [Aspect C230] A compound according to Aspect C80, wherein X 2 is CR 62b [Aspect C231] In Aspect C80, the compound 2 is a nitrogen atom. [Aspect C232] In Aspect C81, X2 is CR 62b [Aspect C233] In the aspect C81, X 2 is a nitrogen atom. [Aspect C234] In Aspect C82, X 2 is CR 62b [Aspect C235] In aspect C82, the compound 2 is a nitrogen atom. [Aspect C236] In Aspect C83, X 2 is CR 62b [Aspect C237] In aspect C83, the compound is 2 is a nitrogen atom. [Aspect C238] In Aspect C84, X 2 is CR 62b [Aspect C239] In Aspect C84, the compound is 2 is a nitrogen atom. [Aspect C240] In Aspect C85, X 2 is CR 62b [Aspect C241] In Aspect C85, the compound is 2 is a nitrogen atom. [Aspect C242] In Aspect C86, X 2 is CR 62b [Aspect C243] In the aspect C86, X 2 is a nitrogen atom. [Aspect C244] In Aspect C87, X 2 is CR 62b [Aspect C245] In aspect C87, the compound 2 is a nitrogen atom. [Aspect C246] In Aspect C88, X 2 is CR 62b [Aspect C247] In aspect C88, the compound is 2 is a nitrogen atom. [Aspect C248] In Aspect C89, X 2 is CR 62b [Aspect C249] In aspect C89, the compound is 2 is a nitrogen atom. [Aspect C250] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2. [Aspect C251] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2 and R 2is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropylmethyl group. [Embodiment C252] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is a C1-C6 alkyl group. [Embodiment C253] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group. [Embodiment C254] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is a C1-C6 alkyl group. [Embodiment C255] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2 and R 2 is an ethyl group. [Aspect C256] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect C257] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by formula Q1. [Aspect C258] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by formula Q1 and A 1 is a nitrogen atom. [Aspect C259] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by formula Q5. [Aspect C260] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect C261] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and Q is a group represented by formula Q1. [Aspect C262] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and Q is a group represented by formula Q1, and A 1 is a nitrogen atom. [Aspect C263] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2 and Q is a group represented by formula Q5. [Aspect C264] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2 and R 2is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropylmethyl group, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Embodiment C265] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropylmethyl group, and Q is a group represented by the formula Q1. [Embodiment C266] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropylmethyl group, Q is a group represented by formula Q1, and A 1 is a nitrogen atom. [Embodiment C267] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropylmethyl group, and Q is a group represented by the formula Q5. [Embodiment C268] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is a C1-C6 alkyl group, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect C269] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is a C1-C6 alkyl group and Q is a group represented by the formula Q1. [Aspect C270] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is a C1-C6 alkyl group, Q is a group represented by formula Q1, and A 1 is a nitrogen atom. [Embodiment C271] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is a C1-C6 alkyl group, and Q is a group represented by the formula Q5. [Embodiment C272] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R2 is an ethyl group, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Embodiment C273] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, and Q is a group represented by the formula Q1. [Embodiment C274] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment C275] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, and Q is a group represented by formula Q5. [Aspect C276] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is a C1-C6 alkyl group, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect C277] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is a C1-C6 alkyl group and Q is a group represented by the formula Q1. [Aspect C278] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is a C1-C6 alkyl group, Q is a group represented by formula Q1, and A 1 is a nitrogen atom. [Embodiment C279] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is a C1-C6 alkyl group and is a group represented by formula Q5. [Aspect C280] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is an ethyl group, and Q is a group represented by formula Q1 or a group represented by formula Q5. [Aspect C281] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is an ethyl group, and Q is a group represented by the formula Q1. [Aspect C282] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A1 is a nitrogen atom. [Embodiment C283] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, and Q is a group represented by the formula Q5. [Aspect C284] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment C285] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is CR 1 [Embodiment C286] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom. [Embodiment C287] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, a halogen atom, or a hydrogen atom. [Aspect C288] A compound in any of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is group L 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group E 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group H 2 a phenyl group optionally substituted with one or more substituents selected from group H 2Compounds which are a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a hydrogen atom. 2 Group E: a group consisting of a cyano group and a halogen atom. 2 Group H: a group consisting of a cyano group and a halogen atom. 2 A: a group consisting of a C1-C4 alkyl group optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom. [Aspect C289] In any of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more cyano groups, a phenyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect C290] A compound in any of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C291] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C292] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3bis a phenyl group optionally substituted with one or more substituents selected from Group H. [Embodiment C293] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a phenyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Embodiment C294] In any of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C295] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a halogen atom. [Embodiment C296] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a , R 3b and R 3d is a hydrogen atom. [Embodiment C297] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d [Embodiment C298] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10cand G 4 is a nitrogen atom. [Embodiment C299] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom. [Embodiment C300] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C301] In any of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C302] In any of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C303] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C304] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a halogen atom. [Aspect C305] In any one of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b , R 10c and R 10dis a hydrogen atom. [Embodiment C306] In any one of Embodiments C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom. [Aspect C307] In any one of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C308] In any of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C309] In any of Aspects C1 to C249 and Compound N of the present invention, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C310] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C311] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein Q is a group represented by the formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a halogen atom. [Embodiment C312] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment C313] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is CR 1[Embodiment C314] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom. [Embodiment C315] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, a halogen atom, or a hydrogen atom. [Aspect C316] A compound in any of Aspects C1 to C249 and Compound N of the Invention, wherein n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is group L 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group E 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group H 2 a phenyl group optionally substituted with one or more substituents selected from group H 2 [Aspect C317] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3aand R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more cyano groups, a phenyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Aspect C318] A compound in any of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C319] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C320] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C321] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3bis a phenyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Embodiment C322] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C323] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a halogen atom. [Embodiment C324] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a , R 3b and R 3d is a hydrogen atom. [Embodiment C325] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d [Embodiment C326] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10cand G 4 is a nitrogen atom. [Embodiment C327] In any of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom. [Embodiment C328] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C329] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10bis a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C330] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C331] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C332] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10bis a halogen atom. [Embodiment C333] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b , R 10c and R 10d is a hydrogen atom. [Embodiment C334] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom. [Aspect C335] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C336] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C337] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C338] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C339] In any of Aspects C1 to C249 and Compound N of the present invention, n is 0 or 2, and R 2is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a halogen atom. [Aspect C340] In any one of Aspects C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom. [Embodiment C341] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is CR 1 [Aspect C342] In any one of Aspects C1 to C249 and Compound N of the present invention, n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom. [Embodiment C343] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, a halogen atom, or a hydrogen atom. [Aspect C344] A compound in any of Aspects C1 to C249 and Compound N of the Invention, wherein n is 2 and R2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is group L 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group E 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group H 2 a phenyl group optionally substituted with one or more substituents selected from group H 2 [Aspect C345] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more cyano groups, a phenyl group optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom. [Embodiment C346] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C347] In any of Aspects C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3bis a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C348] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a phenyl group optionally substituted with one or more substituents selected from Group H. [Aspect C349] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a phenyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. [Embodiment C350] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, in which n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C351] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a and R 3d is a hydrogen atom, and R 3b is a halogen atom. [Embodiment C352] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by the formula Q1, and A 1 is a nitrogen atom, and R 3a , R 3b and R 3dis a hydrogen atom. [Embodiment C353] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d [Embodiment C354] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is a nitrogen atom. [Embodiment C355] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom. [Embodiment C356] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R10b is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C357] In any of Aspects C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C358] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a phenyl group optionally substituted with one or more substituents selected from Group H. [Embodiment C359] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10bis a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C360] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10c and R 10d is a hydrogen atom, and R 10b is a halogen atom. [Embodiment C361] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b , R 10c and R 10d is a hydrogen atom. [Embodiment C362] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom. [Embodiment C363] In any one of Embodiments C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L. [Aspect C364] In any of Aspects C1 to C249 and Compound N of the present invention, n is 2, and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E. [Aspect C365] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a phenyl group optionally substituted with one or more substituents selected from Group H. [Embodiment C366] A compound in any one of Embodiments C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H. [Aspect C367] A compound in any one of Aspects C1 to C249 and Compound N of the present invention, wherein n is 2 and R 2 is an ethyl group, Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d and R 10a , R 10b and R 10d is a hydrogen atom, and R 10c A compound in which is a halogen atom.

[0025] Next, the method for producing the compound of the present invention will be described.

[0026] Production Method 1 A compound represented by formula (I-b) (hereinafter referred to as compound (I-b)) or a compound represented by formula (I-c) (hereinafter referred to as compound (I-c)) can be produced by reacting a compound represented by formula (I-a) (hereinafter referred to as compound (I-a)) with an oxidizing agent.

[0027]

[0028] [In the formula, the symbols have the same meanings as defined above.]

[0029] First, a method for producing compound (I-b) from compound (I-a) will be described. The reaction is usually carried out in a solvent. Examples of the solvent include halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles); alcohols such as methanol and ethanol (hereinafter referred to as alcohols); acetic acid; water; and mixtures of two or more of these. Examples of the oxidizing agent include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be used as necessary. An example of the base is sodium carbonate. When a base is used in the reaction, the base is usually used in a ratio of 0.01 to 1 mole per mole of compound (I-a). Examples of the catalyst include tungstic acid and sodium tungstate. When a catalyst is used in the reaction, the catalyst is usually used in a ratio of 0.01 to 0.5 moles per mole of compound (I-a). In the reaction, an oxidizing agent is typically used in a ratio of 1 to 1.2 moles per mole of compound (I-a). The reaction temperature is typically within the range of -20°C to 80°C. The reaction time is typically within the range of 0.1 to 12 hours. After completion of the reaction, water is added to the reaction mixture, which is then extracted with an organic solvent. The organic layer is washed, as necessary, with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). The resulting organic layer is dried and concentrated to obtain compound (I-b).

[0030] Next, a method for producing compound (I-c) from compound (I-b) will be described. The reaction is typically carried out in a solvent. Examples of solvents include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more of these. Examples of oxidizing agents include mCPBA and hydrogen peroxide. When hydrogen peroxide is used as the oxidizing agent, a base or catalyst may be used as necessary. An example of a base is sodium carbonate. When a base is used in the reaction, the base is typically used in a ratio of 0.01 to 1 mole per mole of compound (I-b). An example of a catalyst is sodium tungstate. When a catalyst is used in the reaction, the catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-b). In the reaction, the oxidizing agent is typically used in a ratio of 1 to 2 moles per mole of compound (I-b). The reaction temperature is typically in the range of -20°C to 120°C. The reaction time is typically in the range of 0.1 to 12 hours. After the reaction is complete, water is added to the reaction mixture, which is then extracted with an organic solvent. The organic layer is washed with an aqueous solution of a reducing agent (e.g., sodium sulfite or sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate) as needed. The resulting organic layer is dried and concentrated to obtain compound (I-c).

[0031] Compound (I-c) can also be produced in a one-step reaction (one-pot) by reacting compound (I-a) with an oxidizing agent. The reaction can be carried out in a similar manner to the method for producing compound (I-c) from compound (I-b) using an oxidizing agent usually in a proportion of 2 to 5 moles per mole of compound (I-a).

[0032] Production Method 2 The compound represented by formula (IS-1) (hereinafter referred to as compound (IS-1)) can be produced by reacting a compound represented by formula (IO-1) (hereinafter referred to as compound (IO-1)) with a sulfiding agent.

[0033] [In the formula, the symbols have the same meanings as above.] The reaction is carried out in a solvent or in the absence of a solvent. Examples of the solvent include ethers such as methyl tert-butyl ether (hereinafter referred to as MTBE), ethylene glycol dimethyl ether, and 1,4-dioxane (hereinafter referred to as ethers); halogenated hydrocarbons; aromatic hydrocarbons such as toluene and xylene (hereinafter referred to as aromatic hydrocarbons); nitriles; nitrogen-containing aromatic compounds such as pyridine, picoline, lutidine, and quinoline; and mixtures thereof. Examples of the sulfurizing agent include diphosphorus pentasulfide and Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide). In the reaction, the sulfurizing agent is usually used in a ratio of 1 to 3 moles per mole of compound (I-O-1). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 1 to 24 hours. After the reaction is complete, the compound (IS-1) 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.

[0034] Production Method 3 The compound represented by formula (IS-2) (hereinafter referred to as compound (IS-2)) can be produced by reacting a compound represented by formula (IO-2) (hereinafter referred to as compound (IO-2)) with a sulfiding agent.

[0035] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except that compound (IO-2) is used in place of compound (IO-1).

[0036] Production Method 4 The compound represented by formula (IS-3) (hereinafter referred to as compound (IS-3)) can be produced by reacting a compound represented by formula (IO-3) (hereinafter referred to as compound (IO-3)) with a sulfiding agent.

[0037] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except that compound (IO-3) is used in place of compound (IO-1).

[0038] Production Method 5 Compound (IO-1) can be produced by reacting a compound represented by formula (M-1-1) (hereinafter referred to as compound (M-1-1)) with a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) in the presence of a base.

[0039] [In the formula, X arepresents a leaving group such as a fluorine atom, chlorine atom, bromine atom, or iodine atom, and other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; aromatic hydrocarbons; nitriles; aprotic polar solvents (hereinafter referred to as aprotic polar solvents) such as dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone (hereinafter referred to as NMP), and dimethyl sulfoxide (hereinafter referred to as DMSO); and mixtures of two or more of these. Examples of the base include organic bases such as triethylamine, diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metal hydrides); and organometallic compounds such as n-butyllithium and lithium bis(trimethylsilyl)amide (hereinafter referred to as organometallic compounds). The reaction can also be carried out using a metal catalyst, if necessary. Examples of metal catalysts include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile)copper(I) hexafluorophosphate, and copper(I) 2-thiophenecarboxylate; nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), and tris(dibenzylideneacetone)dipalladium(0). When a metal catalyst is used in the reaction, the metal catalyst is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (M-1-1). The reaction can also be carried out using a ligand, if necessary.Examples of the ligand include triphenylphosphine, 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (hereinafter referred to as Xantphos), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N'-dimethylcyclohexane-1,2-diamine, and N,N'-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 0.5 moles per mole of compound (M-1-1). For the reaction, compound (M-2) is typically used in a ratio of 0.8 to 1.2 moles, and base is typically used in a ratio of 1 to 3 moles per mole of compound (M-1-1). The reaction temperature is typically in the range of -20°C to 150°C. The reaction time is typically in the range of 0.5 to 24 hours. After completion of the reaction, compound (IO-1) 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 (M-1-1) is a commercially available compound, or can be produced using known methods (e.g., methods described in WO 2012 / 035078, WO 2020 / 022237, etc.).

[0040] Production Method 6 Compound (IO-2) can be produced by reacting a compound represented by formula (M-1-2) (hereinafter referred to as compound (M-1-2)) with compound (M-2) in the presence of a base.

[0041] [In the formula, the symbols have the same meanings as above.] The reaction can be carried out in accordance with Production Method 5, using compound (M-1-2) instead of compound (M-1-1). Compound (M-1-2) is a commercially available compound, or can be produced using known methods (for example, methods described in WO 2004 / 058762, WO 2014 / 048165, WO 2020 / 022237, etc.).

[0042] Production Method 7 Compound (IO-3) can be produced by reacting a compound represented by formula (M-1-3) (hereinafter referred to as compound (M-1-3)) with compound (M-2) in the presence of a base.

[0043] [In the formula, the symbols have the same meanings as above.] The reaction can be carried out in accordance with Production Method 5 using compound (M-1-3) instead of compound (M-1-1). Compound (M-1-3) is a commercially available compound, or can be produced using known methods (for example, methods described in WO 2020 / 022237, Asian journal of Organic Chemistry, 2021, 10, 355, WO 2012 / 035078, WO 2017 / 069279, etc.).

[0044] Production Method 8 The compound represented by formula (In0-1) (hereinafter referred to as compound (In0-1)) can be produced according to the following scheme.

[0045] [In the formula, X d represents a chlorine atom, a bromine atom, or an iodine atom, and other symbols have the same meanings as above.]

[0046] First, a method for producing the compound represented by formula (M-5-1) (hereinafter referred to as compound (M-5-1)) will be described. Compound (M-5-1) can be produced in accordance with Production Method 5, using a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) instead of compound (M-2).

[0047] Next, a method for producing the compound represented by formula (M-6-1) (hereinafter referred to as compound (M-6-1)) will be described. Compound (M-6-1) can be produced by reacting compound (M-5-1) with a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles per mole of compound (M-5-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the compound (M-6-1) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and carrying out post-treatments such as drying and concentrating the organic layer.

[0048] Next, a method for producing compound (I-n0-1) from compound (M-5-1) will be described. Compound (I-n0-1) can be produced by reacting compound (M-5-1), a compound represented by formula (R-1) (hereinafter referred to as compound (R-1)), and a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, compound (R-1) is usually used in a ratio of 1 to 20 moles, and the halogenating agent is usually used in a ratio of 1 to 20 moles per mole of compound (M-5-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the compound (I-n0-1) 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 (R-1) is a commercially available compound or can be produced by a known method.

[0049] Next, a method for producing compound (I-n0-1) from compound (M-6-1) will be described. Compound (I-n0-1) can also be produced by reacting compound (M-6-1) with compound (R-1) in the presence of a metal catalyst and a base. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of these. Examples of the metal catalyst 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; and copper catalysts such as copper(I) iodide and copper(I) chloride. Examples of bases include alkali metal hydrides, alkali metal carbonates, organic bases, and organometallic compounds. A ligand can also be used in the reaction. Examples of ligands include triphenylphosphine, Xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole per mole of compound (M-6-1). In the reaction, compound (R-1) is usually used in a ratio of 1 to 20 moles, metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and base is usually used in a ratio of 0.1 to 5 moles per mole of compound (M-6-1). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-n0-1) 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.

[0050] Production Method 9 The compound represented by formula (In0-2) (hereinafter referred to as compound (In0-2)) can be produced according to the following scheme.

[0051] [In the formula, the symbols have the same meanings as defined above.]

[0052] The compound represented by formula (M-5-2) (hereinafter referred to as compound (M-5-2)) can be produced using compound (M-1-2) instead of compound (M-1-1) in accordance with the method for producing compound (M-5-1) from compound (M-1-1) described in Production Method 8.

[0053] The compound represented by formula (M-6-2) (hereinafter referred to as compound (M-6-2)) can be produced using compound (M-5-2) instead of compound (M-5-1) in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0054] Compound (I-n0-2) can be produced using compound (M-5-2) instead of compound (M-5-1) in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) described in Production Method 8. Compound (I-n0-2) can also be produced using compound (M-6-2) instead of compound (M-6-1) in accordance with the method for producing compound (I-n0-1) from compound (M-6-1) described in Production Method 8.

[0055] Production Method 10 The compound represented by formula (In0-3) (hereinafter referred to as compound (In0-3)) can be produced according to the following scheme.

[0056] [In the formula, the symbols have the same meanings as defined above.]

[0057] The compound represented by formula (M-5-3) (hereinafter referred to as compound (M-5-3)) can be produced using compound (M-1-3) instead of compound (M-1-1) in accordance with the method for producing compound (M-5-1) from compound (M-1-1) described in Production Method 8.

[0058] The compound represented by formula (M-6-3) (hereinafter referred to as compound (M-6-3)) can be produced using compound (M-5-3) instead of compound (M-5-1) in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0059] Compound (I-n0-3) can be produced using compound (M-5-3) instead of compound (M-5-1) in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) described in Production Method 8. Compound (I-n0-3) can also be produced using compound (M-6-3) instead of compound (M-6-1) in accordance with the method for producing compound (I-n0-1) from compound (M-6-1) described in Production Method 8.

[0060] Production Method 11 A compound represented by formula (I-b-p) (hereinafter referred to as compound (I-b-p)) or a compound represented by formula (I-c-p) (hereinafter referred to as compound (I-c-p)) can be produced by reacting a compound represented by formula (I-a-p) (hereinafter referred to as compound (I-a-p)) with an oxidizing agent.

[0061] [In the formula, the symbols have the same meanings as defined above.]

[0062] Compound (I-bp) can be produced by using compound (I-ap) instead of compound (I-a) in accordance with Production Method 1. Compound (I-cp) can be produced by using compound (I-bp) instead of compound (I-b) in accordance with Production Method 1. Compound (I-cp) can also be produced by using compound (I-ap) instead of compound (I-a) in accordance with Production Method 1.

[0063] Production Method 12-1 The compound represented by formula (IS-1p) (hereinafter referred to as compound (IS-1p)) can be produced by reacting a compound represented by formula (IO-1p) (hereinafter referred to as compound (IO-1p)) with a sulfiding agent.

[0064] [In the formula, the symbols have the same meanings as defined above.] Compound (IS-1p) can be produced according to Production Method 2, except that compound (IO-1p) is used instead of compound (IO-1).

[0065] Production Method 12-2 The compound represented by formula (IS-2p) (hereinafter referred to as compound (IS-2p)) can be produced by reacting a compound represented by formula (IO-2p) (hereinafter referred to as compound (IO-2p)) with a sulfiding agent.

[0066] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except for using compound (IO-2p) instead of compound (IO-1).

[0067] Production Method 13 The compound represented by formula (IS-3p) (hereinafter referred to as compound (IS-3p)) can be produced by reacting a compound represented by formula (IO-3p) (hereinafter referred to as compound (IO-3p)) with a sulfating agent.

[0068] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except for using compound (IO-3p) instead of compound (IO-1).

[0069] Production Method 14 The compound represented by formula (IO-1p) (hereinafter referred to as compound (IO-1p)) can be produced by reacting compound (M-1-1) with a compound represented by formula (M-2p) (hereinafter referred to as compound (M-2p)) in the presence of a base.

[0070] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 5, except that compound (M-2p) is used in place of compound (M-2).

[0071] Production Method 15 The compound represented by formula (IO-2p) (hereinafter referred to as compound (IO-2p)) can be produced by reacting compound (M-1-2) with compound (M-2p) in the presence of a base.

[0072] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 6, except that compound (M-2p) is used in place of compound (M-2).

[0073] Production Method 16 The compound represented by formula (IO-3p) (hereinafter referred to as compound (IO-3p)) can be produced by reacting compound (M-1-3) with compound (M-2p) in the presence of a base.

[0074] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 7, except that compound (M-2p) is used in place of compound (M-2).

[0075] Production Method 17 The compound represented by formula (I-n0-1p) (hereinafter referred to as compound (I-n0-1p)) can be produced according to the following scheme.

[0076] [In the formula, the symbols have the same meanings as defined above.]

[0077] The compound represented by formula (M-5-1p) (hereinafter referred to as compound (M-5-1p)) can be produced using compound (M-4p) instead of compound (M-4) in accordance with the method for producing compound (M-5-1) from compound (M-1-1) described in Production Method 8.

[0078] The compound represented by formula (M-6-1p) (hereinafter referred to as compound (M-6-1p)) can be produced using compound (M-5-1p) instead of compound (M-5-1) in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0079] Compound (I-n0-1p) can be produced using compound (M-5-1p) instead of compound (M-5-1) in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) described in Production Method 8. Compound (I-n0-1p) can also be produced using compound (M-6-1p) instead of compound (M-6-1) in accordance with the method for producing compound (I-n0-1) from compound (M-6-1) described in Production Method 8.

[0080] Production Method 18 The compound represented by the formula (In0-2p) (hereinafter referred to as compound (In0-2p)) can be produced according to the following scheme.

[0081] [In the formula, the symbols have the same meanings as defined above.]

[0082] The compound represented by formula (M-5-2p) (hereinafter referred to as compound (M-5-2p)) can be produced using compound (M-4p) instead of compound (M-4) in accordance with the method for producing compound (M-5-2) from compound (M-1-2) described in Production Method 9.

[0083] The compound represented by formula (M-6-2p) (hereinafter referred to as compound (M-6-2p)) can be produced using compound (M-5-2p) instead of compound (M-5-2) in accordance with the method for producing compound (M-6-2) from compound (M-5-2) described in Production Method 9.

[0084] Compound (I-n0-2p) can be produced using compound (M-5-2p) instead of compound (M-5-2) in accordance with the method for producing compound (I-n0-2) from compound (M-5-2) described in Production Method 9. Compound (I-n0-2p) can also be produced using compound (M-6-2p) instead of compound (M-6-2) in accordance with the method for producing compound (I-n0-2) from compound (M-6-2) described in Production Method 9.

[0085] Production Method 19 The compound represented by the formula (In0-3p) (hereinafter referred to as compound (In0-3p)) can be produced according to the following scheme.

[0086] [In the formula, the symbols have the same meanings as defined above.]

[0087] The compound represented by formula (M-5-3p) (hereinafter referred to as compound (M-5-3p)) can be produced using compound (M-4p) instead of compound (M-4) in accordance with the method for producing compound (M-5-3) from compound (M-1-3) described in Production Method 10.

[0088] The compound represented by formula (M-6-3p) (hereinafter referred to as compound (M-6-3p)) can be produced using compound (M-5-3p) instead of compound (M-5-3) in accordance with the method for producing compound (M-6-3) from compound (M-5-3) described in Production Method 10.

[0089] Compound (I-n0-3p) can be produced using compound (M-5-3p) instead of compound (M-5-3) in accordance with the method for producing compound (I-n0-3) from compound (M-5-3) described in Production Method 10. Compound (I-n0-3p) can also be produced using compound (M-6-3p) instead of compound (M-6-3) in accordance with the method for producing compound (I-n0-3) from compound (M-6-3) described in Production Method 10.

[0090] Production Method 20 A compound represented by formula (I-ba) (hereinafter referred to as compound (I-ba)) or a compound represented by formula (I-ca) (hereinafter referred to as compound (I-ca)) can be produced by reacting a compound represented by formula (I-aa) (hereinafter referred to as compound (I-aa)) with an oxidizing agent. [In the formula, the symbols have the same meanings as defined above.]

[0091] Compound (I-ba) can be produced by using compound (I-aa) instead of compound (I-a) according to Production Method 1. Compound (I-ca) can be produced by using compound (I-ba) instead of compound (I-b) according to Production Method 1. Compound (I-ca) can also be produced by using compound (I-aa) instead of compound (I-a) according to Production Method 1.

[0092] Production Method 21 The compound represented by formula (IS-1a) (hereinafter referred to as compound (IS-1a)) can be produced by reacting a compound represented by formula (IO-1a) (hereinafter referred to as compound (IO-1a)) with a sulfiding agent.

[0093] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except for using compound (IO-1a) instead of compound (IO-1).

[0094] Production Method 22 The compound represented by formula (IS-2a) (hereinafter referred to as compound (IS-2a)) can be produced by reacting a compound represented by formula (IO-2a) (hereinafter referred to as compound (IO-2a)) with a sulfating agent.

[0095] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except for using compound (IO-2a) instead of compound (IO-1).

[0096] Production Method 23 The compound represented by formula (IS-3a) (hereinafter referred to as compound (IS-3a)) can be produced by reacting a compound represented by formula (IO-3a) (hereinafter referred to as compound (IO-3a)) with a sulfating agent.

[0097] [wherein the symbols have the same meanings as defined above.] The reaction can be carried out according to Production Method 2, except for using compound (IO-3a) instead of compound (IO-1).

[0098] Production Method 24 The compound represented by formula (I-n0-1a) (hereinafter referred to as compound (I-n0-1a)) can be produced according to the following scheme.

[0099] [In the formula, the symbols have the same meanings as defined above.]

[0100] The compound represented by formula (M-5-1a) (hereinafter referred to as compound (M-5-1a)) can be produced using compound (M-4a) instead of compound (M-4) in accordance with the method for producing compound (M-5-1) from compound (M-1-1) described in Production Method 8.

[0101] The compound represented by formula (M-6-1a) (hereinafter referred to as compound (M-6-1a)) can be produced using compound (M-5-1a) instead of compound (M-5-1) in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0102] Compound (I-n0-1a) can be produced using compound (M-5-1a) instead of compound (M-5-1) in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) described in Production Method 8. Compound (I-n0-1a) can also be produced using compound (M-6-1) instead of compound (M-6-1) in accordance with the method for producing compound (I-n0-1) from compound (M-6-1) described in Production Method 8.

[0103] Production Method 25 The compound represented by the formula (I-n0-2a) (hereinafter referred to as compound (I-n0-2a)) can be produced according to the following scheme.

[0104] [In the formula, the symbols have the same meanings as defined above.]

[0105] The compound represented by formula (M-5-2a) (hereinafter referred to as compound (M-5-2a)) can be produced using compound (M-4a) instead of compound (M-4) in accordance with the method for producing compound (M-5-2) from compound (M-1-2) described in Production Method 9.

[0106] The compound represented by formula (M-6-2a) (hereinafter referred to as compound (M-6-2a)) can be produced using compound (M-5-2a) instead of compound (M-5-2) in accordance with the method for producing compound (M-6-2) from compound (M-5-2) described in Production Method 9.

[0107] Compound (I-n0-2a) can be produced using compound (M-5-2a) instead of compound (M-5-2) in accordance with the method for producing compound (I-n0-2) from compound (M-5-2) described in Production Method 9. Compound (I-n0-2a) can also be produced using compound (M-6-2a) instead of compound (M-6-2) in accordance with the method for producing compound (I-n0-2) from compound (M-6-2) described in Production Method 9.

[0108] Production Method 26 The compound represented by the formula (I-n0-3a) (hereinafter referred to as compound (I-n0-3a)) can be produced according to the following scheme.

[0109] [In the formula, the symbols have the same meanings as defined above.]

[0110] The compound represented by formula (M-5-3a) (hereinafter referred to as compound (M-5-3a)) can be produced using compound (M-4a) instead of compound (M-4) in accordance with the method for producing compound (M-5-3) from compound (M-1-3) described in Production Method 10.

[0111] The compound represented by formula (M-6-3a) (hereinafter referred to as compound (M-6-3a)) can be produced using compound (M-5-3a) instead of compound (M-5-3) in accordance with the method for producing compound (M-6-3) from compound (M-5-3) described in Production Method 10.

[0112] Compound (I-n0-3a) can be produced using compound (M-5-3a) instead of compound (M-5-3) in accordance with the method for producing compound (I-n0-3) from compound (M-5-3) described in Production Method 10. Compound (I-n0-3a) can also be produced using compound (M-6-3a) instead of compound (M-6-3) in accordance with the method for producing compound (I-n0-3) from compound (M-6-3) described in Production Method 10.

[0113] The N-oxide of the compound of formula (I) (i.e., the compound of the present invention) can be produced by reacting the compound of formula (I) with an oxidizing agent. The reaction can be carried out, for example, in accordance with Production Method 1, the method described in U.S. Patent Application Publication No. 2018 / 0009778, or WO 2016 / 121970.

[0114] Production Method 28 The compound represented by formula (I-h1-6) (hereinafter referred to as compound (I-h1-6)) can be produced according to the following scheme.

[0115] [In the formula, in the formula, X g represents a chlorine atom or a bromine atom, and the other symbols have the same meanings as above.]

[0116] First, a method for producing the compound represented by formula (I-h1-6a) (hereinafter referred to as compound (I-h1-6a)) will be described. Compound (I-h1-6a) can be produced by reacting a compound represented by formula (M-9) with thiourea in the presence of a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, thiourea and the halogenating agent are usually used in a ratio of 1 to 5 moles per mole of compound (M-9). The reaction temperature is usually in the range of −20° C. to 200° C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the compound (I-10-6a) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and carrying out post-treatments such as drying and concentrating the organic layer.

[0117] Next, a method for producing compound (I-h1-6) will be described. Compound (I-h1-6) can be produced by reacting compound (I-h1-6a) with a compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) in the presence of a nitrite ester. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of nitrite esters include isoamyl nitrite, isopropyl nitrite, and tert-butyl nitrite. For the reaction, 1 to 5 moles of compound (R-8) and 1 to 5 moles of nitrite ester are typically used per mole of compound (I-h1-6a). The reaction temperature is usually within the range of -20°C to 200°C. The reaction time is usually within the range of 0.1 to 72 hours. After the reaction is complete, compound (I-h1-6) 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 (R-8) is known or can be produced according to known methods.

[0118] Production Method 29 The compound represented by formula (I-h2-4) (hereinafter referred to as compound (I-h2-4)) can be produced by reacting compound (M-9) with a compound represented by formula (R-9) (hereinafter referred to as compound (R-9)) in the presence of N,N-dimethylformamide dimethyl acetal.

[0119] [In the formula, the symbols have the same meanings as defined above.]

[0120] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. For the reaction, 0.9 to 5 moles of compound (R-9) and 1 to 100 moles of N,N-dimethylformamide dimethyl acetal are usually used per mole of compound (M-9). The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, 0.1 to 5 moles of the acid are used per mole of compound (M-9). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, 0.1 to 5 moles of the base are used per mole of compound (M-9). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the reaction mixture is added with water, extracted with an organic solvent, and post-treatments such as drying and concentrating the organic layer can be carried out to obtain compound (I-h2-4). Compound (R-9) is known or can be produced according to known methods. Compound (R-9) may be used as a hydrate or hydrochloride salt.

[0121] Production Method 30 The compound represented by formula (I-h3-4) (hereinafter referred to as compound (I-h3-4)) can be produced by reacting compound (M-9) with a compound represented by formula (R-10) (hereinafter referred to as compound (R-10)) in the presence of N,N-dimethylformamide dimethyl acetal.

[0122] [In the formula, the symbols have the same meanings as defined above.]

[0123] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. For the reaction, typically 1 to 5 moles of compound (R-10) and typically 1 to 100 moles of N,N-dimethylformamide dimethyl acetal are used per mole of compound (M-9). The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, 0.1 to 5 moles of the acid are used per mole of compound (M-9). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, 0.1 to 5 moles of the base are used per mole of compound (M-9). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the reaction mixture is added with water, extracted with an organic solvent, and post-treatments such as drying and concentrating the organic layer can be carried out to obtain compound (I-h3-4). Compound (R-10) is known or can be produced according to known methods. Compound (R-10) may be used as a hydrate or hydrochloride salt.

[0124] Production Method 31 The compound represented by formula (I-h3-1) (hereinafter referred to as compound (I-h3-1)) can be produced according to the following scheme.

[0125] [In the formula, R 52c1 is the group P 2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the following, and the other symbols have the same meanings as defined above.]

[0126] First, a method for producing the compound represented by formula (I-h3-1a) (hereinafter referred to as compound (I-h3-1a)) will be described. Compound (I-h3-1a) can be produced by reacting compound (M-9) with a compound represented by formula (R-11) (hereinafter referred to as compound (R-11)) in the presence of an ammonium salt. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the ammonium salt include ammonium chloride, ammonium bromide, and ammonium acetate. In the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and the ammonium salt is usually used in a ratio of 1 to 5 moles, per mole of compound (M-9). The reaction can also be carried out using an acid or a base, as necessary. Examples of the acid include acetic acid and hydrochloric acid. When an acid is used in the reaction, 0.1 to 5 moles of the acid are used per mole of compound (M-9). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, 0.1 to 5 moles of the base are used per mole of compound (M-9). The reaction temperature is typically within the range of -20°C to 200°C. The reaction time is typically within the range of 0.1 to 72 hours. After completion of the reaction, compound (I-h3-1a) 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 (R-11) is a commercially available compound or can be produced using known methods.

[0127] Next, a method for producing compound (I-h3-1) will be described. Compound (I-h3-1) can be produced by reacting compound (I-h3-1a) with a compound represented by formula (R-12) (hereinafter referred to as compound (R-12)) in the presence of a base. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (I-h3-1a). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (I-h3-1a). In the reaction, compound (R-12) is usually used in a ratio of 1 to 5 moles and base is usually used in a ratio of 1 to 5 moles per mole of compound (I-h3-1a). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-h3-1) 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 (R-12) is a commercially available compound or can be produced using known methods.

[0128] Production Method 32 A compound represented by formula (I-h3-2) (hereinafter referred to as compound (I-h3-2)) can be produced by reacting compound (M-9) with a compound represented by formula (R-11) (hereinafter referred to as compound (R-11)) in the presence of an acid or a base.

[0129] [In the formula, the symbols have the same meanings as defined above.]

[0130] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the acid include acetic acid and hydrochloric acid. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. For the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and the acid or base is usually used in a ratio of 0.1 to 5 moles, per mole of compound (M-9). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (I-h3-2) 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.

[0131] Production Method 33 The compound represented by formula (I-h3-3) (hereinafter referred to as compound (I-h3-3)) can be produced according to the following scheme.

[0132] [In the formula, the symbols have the same meanings as defined above.]

[0133] First, a method for producing a compound represented by formula (M-10) (hereinafter referred to as compound (M-10)) will be described. Compound (M-10) can be produced by reacting compound (M-9) with compound (R-11) in the presence of an acid or a base. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the acid include acetic acid and hydrochloric acid. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. In the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and an acid or base is usually used in a ratio of 0.1 to 5 moles per mole of compound (M-9). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the compound (M-10) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and carrying out post-treatments such as drying and concentrating the organic layer.

[0134] Next, a method for producing compound (I-h3-3) will be described. Compound (I-h3-3) can be produced by reacting compound (M-10) with a sulfurizing agent. The reaction is usually carried out in a solvent. Examples of solvents include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of sulfurizing agents include diphosphorus pentasulfide and Lawesson's reagent. The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (M-10). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (M-10). In the reaction, 1 to 5 moles of the sulfurizing agent are typically used per mole of compound (M-10). The reaction temperature is typically within the range of -20°C to 200°C. The reaction time is typically within the range of 0.1 to 72 hours. After completion of the reaction, compound (I-h3-3) 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.

[0135] The methods for producing intermediates are described below.

[0136] Reference Production Method 1 A compound represented by formula (M-2-n1) (hereinafter referred to as compound (M-2-n1)) and a compound represented by formula (M-2-n2) (hereinafter referred to as compound (M-2-n2)) can be produced by reacting a compound represented by formula (M-2-n0) (hereinafter referred to as compound (M-2-n0)) with an oxidizing agent.

[0137] [In the formula, the symbols have the same meanings as defined above.] These reactions can be carried out in accordance with Production Method 1. Compound (M-2-n1) can be produced in accordance with Production Method 1, using compound (M-2-n0) instead of compound (I-a). Compound (M-2-n2) can be produced in accordance with Production Method 1, using compound (M-2-n1) instead of compound (I-b). Compound (M-2-n2) can also be produced in accordance with Production Method 1, using compound (M-2-n0) instead of compound (I-a).

[0138] Reference Production Method 2 The compound represented by formula (M-2-d) (hereinafter referred to as compound (M-2-d)) can be produced according to the following scheme.

[0139] [In the formula, X c represents a chlorine atom or a bromine atom, R 52 represents a hydrogen atom, a methyl group, or an ethyl group, and other symbols have the same meanings as above.]

[0140] The compound represented by formula (M-20) (hereinafter referred to as compound (M-20)) can be produced by reacting a compound represented by formula (M-19) (hereinafter referred to as compound (M-19)) with a compound represented by formula (R-6) (hereinafter referred to as compound (R-6)). The reaction is usually carried out in a solvent. Examples of the solvent include aromatic hydrocarbons, alcohols, nitriles, and mixtures of two or more of these. The reaction is usually carried out in a ratio of 1 to 10 moles of compound (M-19) per mole of compound (R-6). 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 (M-20) can be obtained by carrying out a usual post-treatment operation. Compound (R-6) and compound (M-19) are commercially available compounds or can be produced using known methods.

[0141] The compound represented by formula (M-21) (hereinafter referred to as compound (M-21)) can be produced by reacting compound (M-20) with a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)). The reaction is usually carried out in a solvent. Examples of the solvent include aromatic hydrocarbons, nitriles, and mixtures thereof. The reaction usually uses 1 to 10 moles of compound (R-7) per mole of compound (M-20). The reaction temperature is usually in the range of 60°C to 120°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (M-21) can be obtained by carrying out a usual post-treatment operation. Compound (R-7) is a commercially available compound or can be produced using a known method.

[0142] The compound represented by formula (M-22) (hereinafter referred to as compound (M-22)) can be produced by reacting compound (M-21) with N-iodosuccinimide. The reaction can be carried out using N-iodosuccinimide as a halogenating agent in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0143] Compound (M-2-d) can be produced by reacting compound (M-21) or compound (M-22) with compound (R-1). This reaction can be carried out in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) or compound (M-6-1) in Production Method 8.

[0144] Reference Production Method 3 The compound represented by formula (M-2-j2) (hereinafter referred to as compound (M-2-j2)) can be produced according to the following scheme.

[0145] [In the formula, the symbols have the same meanings as defined above.]

[0146] The compound represented by formula (M-23) (hereinafter referred to as compound (M-23)) can be produced by reacting compound (M-19) with a compound represented by formula (R-7) (hereinafter referred to as compound (R-7)). The reaction is usually carried out in a solvent. Examples of the solvent include aromatic hydrocarbons, alcohols, nitriles, and mixtures of two or more of these. The reaction usually uses 1 to 10 moles of compound (M-19) per mole of compound (R-7). The reaction temperature usually ranges from 0°C to 200°C. The reaction time usually ranges from 0.1 to 48 hours. After completion of the reaction, compound (M-23) can be obtained by carrying out a usual post-treatment. Compound (R-7) is a commercially available compound or can be produced using a known method.

[0147] The compound represented by formula (M-24) (hereinafter referred to as compound (M-24)) can be produced by reacting compound (M-23) with N-iodosuccinimide. The reaction can be carried out using N-iodosuccinimide as a halogenating agent in accordance with the method for producing compound (M-6-1) from compound (M-5-1) described in Production Method 8.

[0148] The compound represented by formula (M-2-j0) (hereinafter referred to as compound (M-2-j0)) can be produced by reacting compound (M-23) or compound (M-24) with compound (R-1). This reaction can be carried out in accordance with the method for producing compound (I-n0-1) from compound (M-5-1) or compound (M-6-1) described in Production Method 8.

[0149] The compound represented by formula (M-2-j1) and compound (M-2-j2) can be produced by reacting compound (M-2-j0) with an oxidizing agent. Compound (M-2-j1) can be produced in accordance with Production Method 1, using compound (M-2-j0) instead of compound (I-a). Compound (M-2-j2) can be produced in accordance with Production Method 1, using compound (M-2-j1) instead of compound (I-b). Compound (M-2-j2) can also be produced in accordance with Production Method 1, using compound (M-2-j0) instead of compound (I-a).

[0150] Reference Production Method 4 Compound (M-2) can be produced by reacting a compound represented by formula (M-2-h) (hereinafter referred to as compound (M-2-h)) with a halogenating agent.

[0151] [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out, for example, according to the method described in Organic Letters, 2019, 21, 1598.

[0152] The compound represented by the following formula (III-2) (hereinafter referred to as compound (III-2)) is a compound (M-2-h) in which R 2 is an ethyl group, and G 1 is CH and G 2 is CR 10x and G 3 is R 10y and G 4 is CH. Examples of compound (III-2) include the following compounds:

[0153] [R 10x and R 10y are the same or different and represent a halogen atom, a cyclopropyl group, a CF3 group, or a hydrogen atom, and other symbols have the same meanings as above.] The following compounds are examples of compound (III-2). [Aspect E1] In compound (III-2), R 10x is a halogen atom. [Aspect E2] Compound (III-2), wherein R 10xis a fluorine atom. [Aspect E3] Compound (III-2), wherein R 10x is a chlorine atom. [Aspect E4] Compound (III-2), wherein R 10x is a bromine atom. [Aspect E5] Compound (III-2), wherein R 10x is an iodine atom. [Aspect E6] Compound (III-2), wherein R 10x is a chlorine atom, a bromine atom, or an iodine atom. [Aspect E7] Compound (III-2), wherein R 10x is a fluorine atom, a bromine atom, or an iodine atom. [Aspect E8] Compound (III-2), wherein R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [Aspect E9] Compound (III-2), wherein R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [Embodiment E10] A compound of compound (III-2), wherein R 10x [Embodiment E11] A compound in which R 10x [Embodiment E12] Compound (III-2), wherein R 10x is a hydrogen atom. [Embodiment E13] Compound (III-2), 10y is a halogen atom. [Embodiment E14] Compound (III-2), wherein R 10y is a fluorine atom. [Embodiment E15] Compound (III-2), wherein R 10y is a chlorine atom. [Embodiment E16] Compound (III-2), wherein R 10y is a bromine atom. [Embodiment E17] Compound (III-2), wherein R 10y is an iodine atom. [Embodiment E18] Compound (III-2), wherein R 10y is a chlorine atom, a bromine atom, or an iodine atom. [Embodiment E19] Compound (III-2), wherein R 10y is a fluorine atom, a bromine atom, or an iodine atom. [Embodiment E20] Compound (III-2), wherein R 10yis a fluorine atom, a chlorine atom, or an iodine atom. [E21] Compound (III-2), wherein R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [Embodiment E22] Compound (III-2), wherein R 10y [Embodiment E23] A compound in which R 10y [Embodiment E24] Compound (III-2), wherein R 10y is a hydrogen atom. [Aspect E25] A compound in which n is 0 in compound (III-2). [Aspect E26] A compound in which n is 1 in compound (III-2). [Aspect E27] A compound in which n is 2 in compound (III-2). [Aspect E28] A compound in which n is 0 or 1 in compound (III-2). [Aspect E29] A compound in which n is 0 or 2 in compound (III-2). [Aspect E30] A compound in which n is 1 or 2 in compound (III-2). [Aspect E31] A compound in which n is 0 in aspect E12. [Aspect E32] A compound in which n is 1 in aspect E12. [Aspect E33] A compound in which n is 2 in aspect E12. [Aspect E34] A compound in which n is 0 or 1 in aspect E12. [Aspect E35] A compound in which n is 0 or 2 in aspect E12. [Aspect E36] The compound in aspect E12, wherein n is 1 or 2. [Aspect E37] The compound in aspect E12, wherein R 10y is a halogen atom. [E38] In E12, the compound 10y is a fluorine atom. [E39] In E12, the compound 10y is a chlorine atom. [E40] In embodiment E12, R 10y is a bromine atom. [E41] In E12, the compound 10y is an iodine atom. [E42] In the embodiment E12, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E43] In the embodiment E12, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E44] In the embodiment E12, R 10yis a fluorine atom, a chlorine atom, or an iodine atom. [E45] In the embodiment E12, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E46] In the embodiment E12, R 10y is a cyclopropyl group. [E47] In E12, the compound 10y is a CF3 group. [E48] In embodiment E12, R 10y is a hydrogen atom. [Aspect E49] A compound in Aspect E24, wherein n is 0. [Aspect E50] A compound in Aspect E24, wherein n is 1. [Aspect E51] A compound in Aspect E24, wherein n is 2. [Aspect E52] A compound in Aspect E24, wherein n is 0 or 1. [Aspect E53] A compound in Aspect E24, wherein n is 0 or 2. [Aspect E54] A compound in Aspect E24, wherein n is 1 or 2. [Aspect E55] A compound in Aspect E24, wherein R 10x is a halogen atom. [E56] In the embodiment E24, R 10x is a fluorine atom. [E57] In the embodiment E24, R 10x is a chlorine atom. [E58] In the embodiment E24, R 10x is a bromine atom. [E59] In the embodiment E24, R 10x is an iodine atom. [E60] In the embodiment E24, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E61] In the embodiment E24, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E62] In the embodiment E24, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E63] In the embodiment E24, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E64] In embodiment E24, R 10x is a cyclopropyl group. [E65] In the embodiment E24, R 10x is a CF3 group. [E66] In the embodiment E31, R 10yis a halogen atom. [E67] In the embodiment E31, R 10y is a fluorine atom. [E68] In the embodiment E31, R 10y is a chlorine atom. [E69] In the embodiment E31, R 10y is a bromine atom. [E70] In embodiment E31, R 10y is an iodine atom. [E71] In the embodiment E31, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E72] In the embodiment E31, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E73] In the embodiment E31, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E74] In the embodiment E31, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E75] In embodiment E32, R 10y is a halogen atom. [E76] In the embodiment E32, R 10y is a fluorine atom. [E77] In the embodiment E32, R 10y is a chlorine atom. [E78] In the embodiment E32, R 10y is a bromine atom. [E79] In the embodiment E32, R 10y is an iodine atom. [E80] In the embodiment E32, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E81] In the embodiment E32, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E82] In the embodiment E32, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E83] In the embodiment E32, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E93] In the embodiment E33, R 10y is a halogen atom. [E94] In the embodiment E33, R 10y is a fluorine atom. [E95] In the embodiment E33, R 10yis a chlorine atom. [E96] In the embodiment E33, R 10y is a bromine atom. [E97] In the embodiment E33, R 10y is an iodine atom. [E98] In the embodiment E33, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E99] In the embodiment E33, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E100] In embodiment E33, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E101] In the embodiment E33, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E102] In embodiment E34, R 10y is a halogen atom. [E103] In the embodiment E34, R 10y is a fluorine atom. [E104] In embodiment E34, R 10y is a chlorine atom. [E105] In the embodiment E34, R 10y is a bromine atom. [E106] In the embodiment E34, R 10y is an iodine atom. [E107] In the embodiment E34, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E108] In embodiment E34, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E109] In the embodiment E34, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E110] In embodiment E34, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E111] In embodiment E35, R 10y is a halogen atom. [Embodiment E112] In embodiment E35, R 10y is a fluorine atom. [E113] In the embodiment E35, R 10y is a chlorine atom. [E114] In the embodiment E35, R 10y is a bromine atom. [E115] In the embodiment E35, R10y is an iodine atom. [E116] In the embodiment E35, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E117] In the embodiment E35, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E118] In the embodiment E35, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E119] In the embodiment E35, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E120] In embodiment E36, R 10y is a halogen atom. [E121] In the embodiment E36, R 10y is a fluorine atom. [E122] In the embodiment E36, R 10y is a chlorine atom. [E123] In the embodiment E36, R 10y is a bromine atom. [E124] In the embodiment E36, R 10y is an iodine atom. [E125] In the embodiment E36, R 10y is a chlorine atom, a bromine atom, or an iodine atom. [E126] In the embodiment E36, R 10y is a fluorine atom, a bromine atom, or an iodine atom. [E127] In the embodiment E36, R 10y is a fluorine atom, a chlorine atom, or an iodine atom. [E128] In the embodiment E36, R 10y is a fluorine atom, a chlorine atom, or a bromine atom. [E129] In the embodiment E49, R 10x is a halogen atom. [E130] In the embodiment E49, R 10x is a fluorine atom. [E131] In the embodiment E49, R 10x is a chlorine atom. [E132] In the embodiment E49, R 10x is a bromine atom. [E133] In the embodiment E49, R 10x is an iodine atom. [E134] In the embodiment E49, R 10xis a chlorine atom, a bromine atom, or an iodine atom. [E135] In the embodiment E49, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E136] In the embodiment E49, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E137] In the embodiment E49, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E138] In embodiment E50, R 10x is a halogen atom. [E139] In E50, the compound 10x is a fluorine atom. [E140] In embodiment E50, R 10x is a chlorine atom. [E141] In the embodiment E50, R 10x is a bromine atom. [E142] In the embodiment E50, R 10x is an iodine atom. [E143] In the embodiment E50, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E144] In embodiment E50, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E145] In embodiment E50, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E146] In embodiment E50, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E147] In embodiment E51, R 10x is a halogen atom. [E148] In the embodiment E51, R 10x is a fluorine atom. [E149] In embodiment E51, R 10x is a chlorine atom. [E150] In embodiment E51, R 10x is a bromine atom. [E151] In the embodiment E51, R 10x is an iodine atom. [E152] In the embodiment E51, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E153] In the embodiment E51, R 10xis a fluorine atom, a bromine atom, or an iodine atom. [E154] In the embodiment E51, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E155] In the embodiment E51, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E156] In the embodiment E52, R 10x is a halogen atom. [E157] In the embodiment E52, R 10x is a fluorine atom. [E158] In the embodiment E52, R 10x is a chlorine atom. [E159] In the embodiment E52, R 10x is a bromine atom. [E160] In embodiment E52, R 10x is an iodine atom. [E161] In the embodiment E52, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E162] In the embodiment E52, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E163] In the embodiment E52, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E164] In the embodiment E52, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E165] In embodiment E53, R 10x is a halogen atom. [E166] In the embodiment E53, R 10x is a fluorine atom. [E167] In the embodiment E53, R 10x is a chlorine atom. [E168] In the embodiment E53, R 10x is a bromine atom. [E169] In the embodiment E53, R 10x is an iodine atom. [E170] In the embodiment E53, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E171] In embodiment E53, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E172] In the embodiment E53, R 10xis a fluorine atom, a chlorine atom, or an iodine atom. [E173] In the embodiment E53, R 10x is a fluorine atom, a chlorine atom, or a bromine atom. [E174] In embodiment E54, R 10x is a halogen atom. [E175] In the embodiment E54, R 10x is a fluorine atom. [E176] In the embodiment E54, R 10x is a chlorine atom. [E177] In the embodiment E54, R 10x is a bromine atom. [E178] In the embodiment E54, R 10x is an iodine atom. [E179] In the embodiment E54, R 10x is a chlorine atom, a bromine atom, or an iodine atom. [E180] In embodiment E54, R 10x is a fluorine atom, a bromine atom, or an iodine atom. [E181] In embodiment E54, R 10x is a fluorine atom, a chlorine atom, or an iodine atom. [E182] In embodiment E54, R 10x is a fluorine atom, a chlorine atom, or a bromine atom.

[0154] Reference Production Method 5 The compound represented by formula (M-2-f) can be produced by reacting a compound represented by formula (M-2-e) (hereinafter referred to as compound (M-2-e)) with silver fluoride in the presence of a metal catalyst.

[0155] [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out, for example, according to the method described in Journal of the American Chemical Society, 2014, 136, 3792.

[0156] Reference Production Method 6 The compound represented by formula (M-2-g) can be produced by reacting the compound (M-2-e) with sodium iodide in the presence of a metal catalyst. [wherein the symbols have the same meanings as defined above.] The reaction can be carried out, for example, according to the method described in Journal of the American Chemical Society, 2002, 124, 14844.

[0157] Reference Production Method 7 The compound (M-2-n0) can be produced according to the following scheme.

[0158] [In the formula, X b is SR 2 or a hydrogen atom, X f represents a chlorine atom, a bromine atom, or an iodine atom, and other symbols have the same meanings as above.]

[0159] First, a method for producing a compound represented by formula (M-4-f) (hereinafter referred to as compound (M-4-f)) from compound (M-4) will be described. Compound (M-4-f) can be produced by reacting compound (M-4) with a halogenating agent. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of halogenating agents include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, the halogenating agent is usually used in a ratio of 1 to 20 moles per mole of compound (M-4). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the compound (M-4-f) 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.

[0160] Next, a method for producing compound (M-2-n0) from compound (M-4-f) will be described. Compound (M-2-n0) can be produced by reacting compound (M-4-f) with compound (R-1) in the presence of a metal catalyst and a base. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, 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; and copper catalysts such as copper(I) iodide and copper(I) chloride. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, organic bases, and organometallic compounds. A ligand can also be used in the reaction. Examples of the ligand include triphenylphosphine, xantphos, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,1'-bis(diphenylphosphino)ferrocene, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2'-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, and 1,10-phenanthroline. When a ligand is used in the reaction, the ligand is typically used in a ratio of 0.01 to 1 mole per mole of compound (M-4-f). In the reaction, compound (R-1) is usually used in a ratio of 1 to 20 moles, a metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and a base is usually used in a ratio of 0.1 to 5 moles, relative to 1 mole of compound (M-4-f). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours.After the reaction is complete, the compound (M-2-n0) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatments such as drying and concentrating the organic layer.

[0161] Next, a method for producing compound (M-2-n0) from compound (M-4) will be described. Compound (M-2-n0) can also be produced by reacting compound (M-4) with a compound represented by formula (R-3) (hereinafter referred to as compound (R-3)) in the presence of a halogenating agent. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of these. Examples of halogenating agents include bromine, iodine, sodium bromide, potassium bromide, sodium iodide, and potassium iodide. An oxidizing agent can be used in the reaction as needed. Examples of oxidizing agents used in the reaction include hydrogen peroxide, tert-butyl hydroperoxide, and DMSO. When an oxidizing agent is used in the reaction, the oxidizing agent is usually used in a ratio of 1 to 20 moles per mole of compound (M-4). In the reaction, compound (R-3) is typically used in a ratio of 0.5 to 10 moles, and the halogenating agent is typically used in a ratio of 0.05 to 10 moles, per mole of compound (M-4). The reaction temperature is typically in the range of 0°C to 200°C. The reaction time is typically in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-2-n0) 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 (R-3) is known or can be produced according to a known method. Compound (M-4) is known or can be produced according to a known method, for example, as described in WO 2015 / 157093, WO 2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199. and European Journal of Medicinal Chemistry, 2016, 123, 916. It can be produced in accordance with the methods described therein.

[0162] Reference Production Method 8 A compound represented by formula (M-4p-n1) (hereinafter referred to as compound (M-4p-n1)) or a compound represented by formula (M-4p-n2) (hereinafter referred to as compound (M-4p-n2)) can be produced by reacting compound (M-4p-n0) with an oxidizing agent. Compound (M-4p-n2) can also be produced by reacting compound (M-4p-n1) with an oxidizing agent.

[0163] [In the formula, the symbols have the same meanings as defined above.]

[0164] Compound (M-4p-n1) can be produced by using compound (M-4p-n0) instead of compound (I-a) in accordance with Production Method 1. Compound (M-4p-n2) can be produced by using compound (M-4p-n1) instead of compound (I-b) in accordance with Production Method 1. Compound (M-4p-n2) can also be produced by using compound (M-4p-n0) instead of compound (I-a) in accordance with Production Method 1.

[0165] Reference Production Method 9 The compound (M-4p-n0) can be produced according to the following scheme.

[0166] [In the formula, the symbols have the same meanings as defined above.]

[0167] Compound (M-4p-f) can be produced using compound (M-4p) instead of compound (M-4) in accordance with the method of producing compound (M-4-f) from compound (M-4) described in Reference Production Method 7. Compound (M-4p-n0) can be produced using compound (M-4p-f) instead of compound (M-4-f) in accordance with the method of producing compound (M-2-n0) from compound (M-4-f) described in Reference Production Method 7. Furthermore, compound (M-4p-n0) can be produced using compound (M-4p) instead of compound (M-4) in accordance with the method of producing compound (M-2-n0) from compound (M-4) described in Reference Production Method 7. Compound (M-4p) is known or can be produced according to known methods (for example, methods described in WO 2017 / 024167, Tetrahedron, 2008, 64, 372, WO 2021 / 188944, etc.).

[0168] Reference Production Method 10 A compound represented by formula (M-4a-n1) (hereinafter referred to as compound (M-4a-n1)) or a compound represented by formula (M-4a-n2) (hereinafter referred to as compound (M-4a-n2)) can be produced by reacting compound (M-4a-n0) with an oxidizing agent. Compound (M-4a-n2) can also be produced by reacting compound (M-4a-n1) with an oxidizing agent.

[0169] [In the formula, the symbols have the same meanings as defined above.]

[0170] Compound (M-4a-n1) can be produced by using compound (M-4a-n0) instead of compound (I-a) in accordance with Production Method 1. Compound (M-4a-n2) can be produced by using compound (M-4a-n1) instead of compound (I-b) in accordance with Production Method 1. Compound (M-4a-n2) can also be produced by using compound (M-4a-n0) instead of compound (I-a) in accordance with Production Method 1.

[0171] Reference Production Method 11 Compound (M-4a-n0) can be produced according to the following scheme.

[0172] [In the formula, the symbols have the same meanings as defined above.]

[0173] Compound (M-4a-f) can be produced using compound (M-4a) instead of compound (M-4) in accordance with the method of producing compound (M-4-f) from compound (M-4) described in Reference Production Method 7. Compound (M-4a-n0) can be produced using compound (M-4a-f) instead of compound (M-4-f) in accordance with the method of producing compound (M-2-n0) from compound (M-4-f) described in Reference Production Method 7. Furthermore, compound (M-4a-n0) can be produced using compound (M-4a) instead of compound (M-4) in accordance with the method of producing compound (M-2-n0) from compound (M-4) described in Reference Production Method 7. Compound (M-4a) is known or can be produced according to a known method (for example, a method described in The Journal of Organic Chemistry, 2006, 71, 3754; The Journal of Organic Chemistry, 2019, 84, 15877; Synlett, 2017, 28, 1636; Chemical Communications, 2011, 47, 10476, etc.).

[0174] Reference Production Method 12 The compound represented by formula (M-h1-6) (hereinafter referred to as compound (M-h1-6)) can be produced according to the following scheme.

[0175] [In the formula, X g represents a chlorine atom or a bromine atom, and the other symbols have the same meanings as above.]

[0176] First, a method for producing the compound represented by formula (M-h1-6a) (hereinafter referred to as compound (M-h1-6a)) will be described. Compound (M-h1-6a) can be produced by reacting a compound represented by formula (M-h0) (hereinafter referred to as compound (M-h0)) with thiourea in the presence of a halogenating agent. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the halogenating agent include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-iodosuccinimide. In the reaction, 1 to 5 moles of thiourea and 1 to 5 moles of the halogenating agent are typically used per mole of compound (M-h0). The reaction temperature is usually within the range of −20°C to 200°C. The reaction time is usually within the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h1-6a) 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 (M-h0) is known or can be produced according to known methods (for example, the method described in WO 2012 / 035078, etc.).

[0177] Next, a method for producing compound (M-h1-6) will be described. Compound (M-h1-6) can be produced by reacting compound (M-h1-6a) with a compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) in the presence of a nitrite ester. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of nitrite esters include isoamyl nitrite, isopropyl nitrite, and tert-butyl nitrite. For the reaction, 1 to 5 moles of compound (R-8) and 1 to 5 moles of nitrite ester are typically used per mole of compound (M-h1-6a). The reaction temperature is usually within the range of -20°C to 200°C. The reaction time is usually within the range of 0.1 to 72 hours. After the reaction is complete, the compound (M-h1-6) 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 (R-8) is known or can be produced according to known methods.

[0178] Reference Production Method 13 The compound represented by formula (M-h2-4) (hereinafter referred to as compound (M-h2-4)) can be produced by reacting compound (M-h0) with a compound represented by formula (R-9) (hereinafter referred to as compound (R-9)) in the presence of N,N-dimethylformamide dimethyl acetal.

[0179] [In the formula, the symbols have the same meanings as defined above.]

[0180] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. In the reaction, compound (R-9) is usually used in an amount of 0.9 to 5 moles and N,N-dimethylformamide dimethyl acetal is usually used in an amount of 1 to 100 moles per mole of compound (M-h0). The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in an amount of 0.1 to 5 moles per mole of compound (M-h0). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in an amount of 0.1 to 5 moles per mole of compound (M-h0). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h2-4) 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 (R-9) is known or can be produced according to known methods. Compound (R-9) may be used as a hydrate or hydrochloride salt.

[0181] Reference Production Method 14 The compound represented by formula (M-h3-4) (hereinafter referred to as compound (M-h3-4)) can be produced by reacting compound (M-h0) with a compound represented by formula (R-10) (hereinafter referred to as compound (R-10)) in the presence of N,N-dimethylformamide dimethyl acetal.

[0182] [In the formula, the symbols have the same meanings as defined above.]

[0183] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. In the reaction, typically 1 to 5 moles of compound (R-10) and typically 1 to 100 moles of N,N-dimethylformamide dimethyl acetal are used per mole of compound (M-h0). The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (M-h0). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (M-h0). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After the reaction is complete, the reaction mixture is added with water, extracted with an organic solvent, and post-treatments such as drying and concentrating the organic layer can be carried out to obtain compound (M-h3-4). Compound (R-10) is known or can be produced according to known methods. Compound (R-10) may be used as a hydrate or hydrochloride salt.

[0184] Reference Production Method 15 The compound represented by formula (M-h3-1) (hereinafter referred to as compound (M-h3-1)) can be produced according to the following scheme.

[0185] [In the formula, R 52c1 is the group P 2 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the following, and the other symbols have the same meanings as defined above.]

[0186] First, a method for producing the compound represented by formula (M-h3-1a) (hereinafter referred to as compound (M-h3-1a)) will be described. Compound (M-h3-1a) can be produced by reacting compound (M-h0) with a compound represented by formula (R-11) (hereinafter referred to as compound (R-11)) in the presence of an ammonium salt. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the ammonium salt include ammonium chloride, ammonium bromide, and ammonium acetate. In the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and the ammonium salt is usually used in a ratio of 1 to 5 moles, relative to 1 mole of compound (M-h0). The reaction can also be carried out using an acid or a base, as necessary. Examples of the acid include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (M-h0). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (M-h0). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h3-1a) 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 (R-11) is a commercially available compound or can be produced using known methods.

[0187] Next, a method for producing compound (M-h3-1) will be described. Compound (M-h3-1) can be produced by reacting compound (M-h3-1a) with a compound represented by formula (R-12) (hereinafter referred to as compound (R-12)) in the presence of a base. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. The reaction can also be carried out using an acid or a base, as necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (M-h3-1a). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (M-h3-1a). In the reaction, compound (R-12) is usually used in a ratio of 1 to 5 moles and base is usually used in a ratio of 1 to 5 moles per mole of compound (M-h3-1a). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h3-1) 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 (R-12) is a commercially available compound or can be produced using known methods.

[0188] Reference Production Method 16: The compound represented by formula (M-h3-2) (hereinafter referred to as compound (M-h3-2)) can be produced by reacting compound (M-h0) with compound (R-11) in the presence of an acid or a base.

[0189] [In the formula, the symbols have the same meanings as defined above.]

[0190] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of the acid include acetic acid and hydrochloric acid. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. In the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and an acid or base is usually used in a ratio of 0.1 to 5 moles, per mole of compound (M-h0). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h3-2) 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.

[0191] Reference Production Method 17 The compound represented by formula (M-h3-3) (hereinafter referred to as compound (M-h3-3)) can be produced according to the following scheme.

[0192] [In the formula, the symbols have the same meanings as defined above.]

[0193] First, a method for producing the compound represented by formula (M-h3-3a) (hereinafter referred to as compound (M-h3-3a)) will be described. Compound (M-h3-3a) can be produced by reacting compound (M-h0) with compound (R-11) in the presence of an acid or a base. The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more thereof. Examples of the acid include acetic acid and hydrochloric acid. Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. In the reaction, compound (R-11) is usually used in a ratio of 0.8 to 5 moles, and the acid or base is usually used in a ratio of 0.1 to 5 moles, per mole of compound (M-h0). The reaction temperature is usually within the range of −20° C. to 200° C. The reaction time is usually within the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h3-3a) 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.

[0194] Next, a method for producing compound (M-h3-3) will be described. Compound (M-h3-3) can be produced by reacting compound (M-h3-3a) with a sulfurizing agent. The reaction is usually carried out in a solvent. Examples of solvents include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of sulfurizing agents include diphosphorus pentasulfide and Lawesson's reagent. The reaction can also be carried out using an acid or a base, if necessary. Examples of acids include acetic acid and hydrochloric acid. When an acid is used in the reaction, the acid is used in a ratio of 0.1 to 5 moles per mole of compound (M-h3-3a). Examples of bases include organic bases, alkali metal carbonates, alkali metal hydrides, and organometallic compounds. When a base is used in the reaction, the base is used in a ratio of 0.1 to 5 moles per mole of compound (M-h3-3a). In the reaction, 1 to 5 moles of the sulfurizing agent are typically used per mole of compound (M-h3-3a). The reaction temperature is typically within the range of -20°C to 200°C. The reaction time is typically within the range of 0.1 to 72 hours. After completion of the reaction, compound (M-h3-3) 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.

[0195] Reference Production Method 18 Formula (M-8) (hereinafter referred to as compound (M-8)) can be produced by reacting a compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) with compound (M-4a-n2) in the presence of a base.

[0196] [W 2a and W 2b are the same or different and represent an oxygen atom or a sulfur atom; R 100a and R 100b are the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group X, or R 100a and R 100b and the W that they combine 2a , W 2band together with each other represent a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E, and the other symbols have the same meanings as defined above.

[0197] The reaction can be carried out in accordance with Production Method 5, using compound (M-7) instead of compound (M-1-1). Compound (M-7) is a commercially available compound, or can be produced using known methods (for example, WO 2021 / 180147).

[0198] Reference Production Method 19 Formula (M-9) can be produced by reacting compound (M-8) with an acid.

[0199] [In the formula, the symbols have the same meanings as defined above.]

[0200] The reaction is usually carried out in a solvent. Examples of the solvent include alcohols, nitriles, ethers, aromatic hydrocarbons, aprotic polar solvents, halogenated hydrocarbons, water, and mixtures of two or more of these. Examples of the acid include acetic acid and hydrochloric acid. In the reaction, the acid is usually used in a ratio of 1 to 100 moles per mole of compound (M-8). The reaction temperature is usually in the range of -20°C to 200°C. The reaction time is usually in the range of 0.1 to 72 hours. After completion of the reaction, compound (M-9) 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.

[0201] 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.

[0202] Group (a) includes acetylcholinesterase inhibitors (e.g., carbamate insecticides, organophosphate insecticides), GABAergic chloride channel blockers (e.g., phenylpyrazole insecticides), sodium channel modulators (e.g., pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (e.g., neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (e.g., macrolide insecticides), juvenile hormone mimics, 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 classes III and IV, voltage-dependent sodium channel blockers, acetyl-CoA carboxylase inhibitors, ryanodine receptor modulators (e.g., diamide insecticides), chordotonal organ modulators, microbial insecticides, and other insecticidal, acaricidal, and nematicidal active ingredients, which are described in the IRAC mechanism-based classification.

[0203] 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., anilinopyridine 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.

[0204] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0205] Group (d) is a group of repellent ingredients.

[0206] Examples of combinations of the present component and the compound 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 group SX1 to SX128. The present components described below are all known components and can be obtained from commercially available preparations or produced by known methods. When the present component is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0207] 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, flufenprox + SX, flufenoxuron + SX, flufiprole + SX, flumethrin + SX, flupentiofenox + SX, flupyradifurone + SX, flupyrimin + SX, flupyroxystrobin + SX, fluralaner + SX, fluvalinate + SX, fluxametamide + SX,Formetanate + SX, fosthiazate + SX, furamethrin + SX, furathiocarb + SX, gamma-cyhalothrin + SX, GS-omega / kappa HXTX-Hv1a peptide + SX, halfenprox + SX, halofenozide + SX, heptafluthrin + SX, heptenophos + SX, hexaflumuron + SX, hexythiazox + SX, potassium salt of hop beta acid + SX, hydramethylnon + SX, hydroprene + SX, imicyafos + SX, imidacloprid + SX, imidaclothiz + SX, imiprothrin + SX, indazapyroxamet + SX, indoxacarb + SX, isocycloseram + SX, isofenphos + SX, isoflualanam + SX, isoprocarb + SX, isopropyl-O-(methoxyaminothiophosphoryl) salicylate + SX, Isoxathion + SX, Ivermectin + SX, Kadethrin + SX, Kappa-tefluthrin + SX, Kappa-bifenthrin + SX,Kinoprene + SX, lambda-cyhalothrin + SX, ledprona + SX, lenoremycin + SX, lepimectin + SX, lime sulfur + SX, 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, pyflubumide + 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 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, 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, tiapyrachlor + 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, tyclopyrazoflor + SX, umifoxolaner + SX, vadescana + SX, vamidothion + SX, Quassia amara wood extract + SX, 3,5-dimethylphenyl N-methylcarbamate (XMC) + 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, Bacillus thuringiensis-derived 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) + SX, Vip3A protein from Bacillus thuringiensis (Bacillus thuringiensis Vip3A protein) + SX, mCry3A protein from Bacillus thuringiensis (Bacillus thuringiensis mCry3A protein) + SX, Cry3Ab protein from Bacillus thuringiensis (Bacillus thuringiensis thuringiensis Cry3Ab protein + SX, Bacillus thuringiensis Cry3Bb protein + SX, Bacillus thuringiensis Cry34Ab1 / Cry35Ab1 protein + SX, Adoxophyes orana GV (granulovirus) strain BV-0001 + SX, Anticarsia gemmatalis MNPV (multiple nucleocapsid nucleopolyhedrovirus) + SX,Autographa californica MNPV + SX, Cydia pomonella GV strain V15 + SX, Cydia pomonella GV strain V22 + SX, Cryptophlebia leucotreta GV + SX, Dendrolimus punctatus cypovirus + SX, Helicoverpa armigera nucleopolyhedrovirus BV-0003 + SX, Helicoverpa zea ... NPV) + SX, Lymantria dispar NPV + SX, Mamestra brassicae NPV + SX, Mamestra configurata NPV + SX, Neodiprion abietis NPV + SX, Neodiprion lecontei NPV + SX, Neodiprion sertifer NPV + SX, Nosema locustae NPV + SX, Orgyia pseudotsugata NPV + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua MNPV + SX,Spodoptera littoralis MNPV + SX, Scalloped aphids (Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus firmus strain NCIM2637 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 serotype H5a5b + 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。,

[0208] 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, 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, 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, chloroinconazide + 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, 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, 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, methasulfocarb + SX, metiram + SX, metominostrobin + SX, metrafenone + SX, metyltetraprole + SX, myclobutanil + SX, naftifine + SX, nuarimol + SX, octhilinone + 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, quinconazole + SX, Quinofumelin + SX, quinoxyfen + SX, quintozene + SX,Quinoa saponins (Chenopodiaceae) + 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,トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(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-(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, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate + SX, methyl (Z)-2-[(3-isopropyl-1H-pyrazol-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate + 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, methyl (2Z)-3-methoxy-2-[(4-methyl[1,1'-biphenyl]-3-yl)oxy]prop-2-enoate + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens strain PTA-4838 (Aveo™ EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + 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。,

[0209] 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. ,

[0210] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.

[0211] 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.

[0212] 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.

[0213] 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 white giant leafhopper (Cofana spectra), and Amrasca biguttula biguttula; Aphrophoridae, such as the European spittlebug (Philaenus spumarius); Cercopidae, such as 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);

[0214] 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 Japanese corn moth (Elasmopalpus lignosellus), the Indian meal moth (Plodia interpunctella), the Japanese two-spotted moth (Euzophera batangensis), and the Japanese 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 Heliothis spp. such as the cotton bollworm (Chrysodeixis includens), Trichoplusia spp., and 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); Pieridae such as the cabbage white butterfly (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 (Gelechiidae) such as the peach leaf moth (Anarsia lineatella), the potato leaf moth (Helcystogramma triannulella), the red bollworm moth (Pectinophora gossypiella), the potato tuber moth (Pthorimaea operculella), and the tomato leaf moth (Tuta absoluta); Arctiidae (Arctiidae) such as the American fall webworm (Hyphantria cunea); Castniidae (Castniidae) such as the giant sugarcane borer (Telchin licus); Cossidae (Cossidae) such as the small box moth (Cossus insularis); Geometridae (Geometridae) such as the mugwort geometrid (Ascotis selenaria); Parasa Limacodidae such as Stathmopodidae (Stathmopoda masinissa) and the like; Sphingidae such as Acherontia lachesis (Sphingidae); Sesiidae such as Nokona feralis (Nokona feralis), Synanthedon hector (Synanthedon tenuis) and the like; Hesperiidae such as Parnara guttata (Parnara guttata); Tineidae such as Tinea translucens (Tineola bisselliella) and the like.

[0215] 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.

[0216] 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 melanogaster (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 flies; Fannidae (Family Fannidae);

[0217] 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 The Aracanthus spp. (Aracanthus spp.) such as Aracanthus griseus, Scepticus uniformis, Aracanthus mourei, and the cotton root borer (Eutinobothrus brasiliensis) are also included in the Curculionidae family; the Tenebrionidae (Tenebrionidae) such as Tribolium castaneum, Tribolium confusum, and Alphitobius diaperinus are also included in the Coccinellidae family; the Flat-headed Ladybird (Lyctus brunneus), the Rhizopertha dominica); Ptinidae; Cerambycidae, such as Anoplophora malasiaca, Migdolus fryanus, and Aromia bungii;Elateridae beetles such as the Okinawan wireworm beetle (Melanotus okinawensis), the brown-headed wireworm beetle (Agriotes fuscicollis), the comb beetle (Melanotus legatus), the foot-striped wireworm beetle (Anchastus spp.), the Conoderus spp., the Ctenicera spp., the Limonius spp., and the Aeolus spp.; Staphylinidae beetles such as the blue-leaf rove beetle (Paederus fuscipes); the small-leaved weevils (Anthrenus verbasci) and the white-striped weevils (Dermestes Dermestidae such as Trogoderma granarium (Trogoderma maculates) and the like; Anobiidae such as Lasioderma serricorne (tobacco beetle) and Stegobium paniceum (Anobiidae); Laemophloeidae such as Cryptolestes ferrugineus (Laemophloeidae); Silvanidae such as Oryzaephilus surinamensis (Silvanidae); Nitidulidae such as Brassicogethes aeneus (Blossom beetle).

[0218] 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).

[0219] 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, Formicidae such as Anoplolepis gracilipes; Vespa mandarinia, Vespa simillima, Vespa analis, Vespa Vespidae, such as Polistes velutina and Polistes jokahamae; Siricidae, such as Urocerus gigas; and Bethylidae.

[0220] 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.

[0221] 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).

[0222] 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.

[0223] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0224] 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.

[0225] 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).

[0226] 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.

[0227] 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.

[0228] 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, a liquid carrier, or a 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.

[0229] 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.).

[0230] 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.).

[0231] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0232] 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.).

[0233] 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.

[0234] In addition, adjuvants can be used as components that enhance or support the efficacy of the compound of the present invention. Specific examples include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).

[0235] 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.

[0236] 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.

[0237] 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).

[0238] 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.

[0239] 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.

[0240] Alternatively, the resin preparation can be processed into a sheet or string shape and wrapped around the crop, stretched around the crop, or spread on the soil around the base of the plant.

[0241] 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.

[0242] 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.

[0243] The compound of the present invention or Composition A can be used as an agent for controlling arthropod pests in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0244] 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, 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, solanaceous vegetables (eggplant, tomato, bell pepper, chili pepper) , potatoes, etc.), Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), Cruciferous 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.), Umbelliferae vegetables (carrots, parsley, celery, parsley, etc.), Chenopodiaceae vegetables (spinach, Swiss chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, scallions, Sweet potatoes, 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, grapefruits, 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, coconuts, ornamental plants, forest plants,Turfgrass, pasture grass,

[0245] 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.

[0246] The present invention will be explained in more detail below with reference to production examples, formulation examples, and test examples, but the present invention is not limited to these examples. In this specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, Bu represents a butyl group, t-Bu represents a tert-butyl group, Hex represents a hexyl group, c-Pr represents a cyclopropyl group, c-Bu represents a cyclobutyl group, Ph represents a phenyl group, Boc represents a tert-butoxycarbonyl group, Py2 represents a 2-pyridyl group, Py3 represents a 3-pyridyl group, and Py4 represents a 4-pyridyl group. When c-Pr, Ph, Py2, Py3, and Py4 are substituted with a substituent, the substituent and the substitution position are written before the symbol. For example, 1-CN-c-Pr represents a 1-cyanocyclopropyl group, 3,4-F2-Ph represents a 3,4-difluorophenyl group, and 4-CF3-Py2 represents a 4-(trifluoromethyl)-2-pyridyl group.

[0247] 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] - The time and retention time (hereinafter referred to as RT) are also recorded. The conditions for liquid chromatography (hereinafter referred to as LC) and mass spectrometry (hereinafter referred to as MS) are as follows. [LC conditions] Column: L-column2 ODS, inner diameter 4.6 mm, length 30 mm, particle size 3 μm (Chemicals Evaluation and Research Institute, Japan) UV measurement wavelength: 254 nm Mobile phase: Solution A: 0.1% formic acid aqueous solution, Solution B: 0.1% formic acid acetonitrile Flow rate: 2.0 mL / min Pump: Two LC-20AD pumps (Shimadzu Corporation) (high-pressure gradient) Gradient conditions: Solution was delivered at the concentration gradient shown in [Table LC1].

[0248]

[0249] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS

[0250] First, examples of the preparation of the compounds of the present invention and their intermediates will be shown.

[0251] Reference Production Example 1: To a mixture of 1.0 g of 2,5,6,7-tetrahydro-4H-pyridazolo[4,3-c]pyridin-4-one (prepared in accordance with the method described in WO 2015 / 175719) and 12 mL of N,N-dimethylformamide, 1.5 mL of triethylamine and 2.2 g of trityl chloride were added and stirred at room temperature. Water was added to the resulting mixture, and the mixture was filtered. The resulting solid was dried under reduced pressure to obtain 2.1 g of Intermediate 1.

[0252]

[0253] Intermediate 1: 1 H-NMR (CDCl3) δ 7.85 (s, 1H), 7.32-7.27 (m, 9H), 7.16-7.11 (m, 6H), 5.76 (s, 1H), 3.60-3.56 (m, 2H), 2.95-2.92 (m, 2H)

[0254] Preparation Example 1: To a mixture of 1.0 g of Intermediate 1 and 5.2 mL of tetrahydrofuran, 4.0 mL of lithium bis(trimethylsilyl)amide (1.0 mol / L tetrahydrofuran solution) was added under ice-cooling, and the mixture was stirred for 15 minutes under ice-cooling. Subsequently, 1.1 g of 5-bromo-3-(ethylsulfonyl)-2-fluoropyridine prepared according to the method described in WO 2019 / 131575 was added, and the mixture was stirred at room temperature for 28 hours. The resulting mixture was added to ice water and extracted with ethyl acetate. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (chloroform:methanol=10:1) to obtain 0.74 g of the present compound 6.

[0255]

[0256] Compound 6 of the present invention: 1 H-NMR (CDCl3) δ 8.83 (d, 1H), 8.52 (d, 1H), 7.92 (s, 1H), 7.35-7.29 (m, 9H), 7.19-7.13 (m, 6H), 4.16-4.09 (m, 1H), 3.88-3.83 (m, 1H), 3.44-3.35 (m, 1H), 3.34-3.27 (m, 2H), 3.05 (dt, 1H), 1.29 (t, 3H)

[0257] Production Example 2: To a mixture of 0.7 g of Compound 6 of the present invention, 0.28 g of 3,5-difluorophenylboronic acid, 0.64 g of potassium phosphate, and 68 mg of tetrakistriphenylphosphinepalladium(0), 12 mL of 1,2-dimethoxyethane and 1.2 mL of water were added and stirred at 90°C for 25 hours. Water 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 under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.47 g of Compound 1 of the present invention.

[0258] Compound 1 of the present invention: 1H-NMR (CDCl3) δ 8.95 (d, 1H), 8.53 (d, 1H), 7.94 (s, 1H), 7.35-7.31 (m, 9H), 7.19-7.17 (m, 8H), 6.97-6.91 (m, 1H), 4.22-4.15 (m, 1H), 3.94-3.89 (m, 1H), 3.48-3.31 (m, 3H), 3.11-3.05 (m, 1H), 1.30 (t, 3H)

[0259] Preparation Example 3: To a mixture of 0.47 g of Compound 1 of the present invention and 1.4 mL of chloroform, 0.5 mL of trifluoroacetic acid was added under ice-cooling, and the mixture was stirred at room temperature for 30 hours. After that, saturated aqueous sodium bicarbonate solution was added under ice-cooling. The resulting mixture was extracted with chloroform. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography (hexane:ethyl acetate=1:1) to obtain 0.18 g of Compound 2 of the present invention.

[0260] Compound 2 of the present invention: 1 H-NMR (CDCl3) δ 10.11-10.40 (br s, 1H), 8.96 (d, 1H), 8.53 (d, 1H), 8.09 (s, 1H), 7.21-7.15 (m, 2H), 6.99-6.92 (m, 1H), 4.26-4.18 (m, 1H), 3.97-3.92 (m, 1H), 3.47-3.32 (m, 3H), 3.13-3.07 (m, 1H), 1.32 (t, 3H)

[0261] Reference Production Ex...

Claims

Formula (I) [During the ceremony, Q expressed by the following formula represents a group represented by formula Q1, a group represented by formula Q2, a group represented by formula Q3, a group represented by formula Q4, a group represented by formula Q5, a group represented by formula Q6, or a group represented by formula Q7 (# represents a bonding site to a sulfur atom, and ● represents a bonding site to Het), A 1 is a nitrogen atom or CR 1 represents R 1 represents a halogen atom or a hydrogen atom, G 1 is a nitrogen atom or CR 10a represents G 2 is a nitrogen atom or CR 10b represents G 3 is a nitrogen atom or CR 10c represents G 4 is a nitrogen atom or CR 10d represents G 5 is a nitrogen atom or CR 10e represents G 6 is a nitrogen atom or CR 10f represents G 7 is a nitrogen atom or CR 10g represents n represents 0, 1 or 2; R 2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, a cyclopropylmethyl group, or NR 5 R 6 represents R 5 and R 6 are the same or different and represent a C1-C6 alkyl 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, or R 5 and R 6 may be taken together with the nitrogen atom to which they are attached to form an aziridinyl, azetidinyl, pyrrolidinyl, or piperidyl group; Y 1 is NR 7 , an oxygen atom, or a sulfur atom; R 7 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a phenyl group {the phenyl group may be substituted with one or more substituents selected from Group H}, R 3a , R 3b , R 3d , R 10a , R 10b , R 10c , R 10d , R 10e , R 10f and R 10g are the same or different and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group E, a phenyl group optionally substituted with one or more substituents selected from Group H, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group H, OR 12 , N.R. 11 R 12 , N.R. 18 R 19 , N.R. 24 NR 11 R 12 , N.R. 24 OR 11 , N.R. 11 C(O)R 13 , N.R. 24 NR 11 C(O)R 13 , N.R. 11 C(O)OR 14 , N.R. 24 NR 11 C(O)OR 14 , N.R. 11 C(O)NR 31 R 32 , N.R. 24 NR 11 C(O)NR 31 R 32 , N=CHNR 31 R 32 , N=S(O) p R 15 R 16 , C(O)R 13 , C(O)OR 17 , C(O)NR 31 R 32 , C(O)NR 11 S(O)2R 23 , C.R. 30 = NOR 17 , N.R. 11 CR 24 = NOR 17 , S(O) q R 23 , a cyano group, a nitro group, a hydrogen atom, or a halogen atom; R 3a , R 3b , and R 3d two adjacent substituents among the above may be taken together with the two carbon atoms to which they are bonded to form a benzene ring, a pyrrole ring, a furan ring, a thiophene ring, a pyrazole ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring or a pyrazine ring {the benzene ring, the pyrrole ring, the furan ring, the thiophene ring, the pyrazole ring, the imidazole ring, the oxazole ring, the isoxazole ring, the thiazole ring, the isothiazole ring, the pyridine ring, the pyridazine ring, the pyrimidine ring and the pyrazine ring are optionally substituted with one or more substituents selected from Group H} or a triazole ring optionally substituted with one or more substituents selected from Group I, p represents 0 or 1; q represents 0, 1 or 2; R 11 , R 24 , R 36 , and R 37 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 12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group J, a phenyl group optionally substituted with one or more substituents selected from Group D, a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, a hydrogen atom, or S(O)R 23 represents R 13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more substituents selected from Group D, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group D, or a hydrogen atom; R 14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group (the phenyl moiety in the phenyl C1-C3 alkyl group optionally substituted with one or more substituents selected from Group D), R 15 and R 16 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, R 17 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 D, or a hydrogen atom; R 18 and R 19 represent, together with the nitrogen atom to which they are bonded, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E; R 23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more substituents selected from Group D, R 30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 35 , N.R. 36 R 37 or a hydrogen atom, R 31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, S(O)R 23 or a hydrogen atom, R 32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group J, or a hydrogen atom; R 35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, Het is a group represented by the formula Het1, a group represented by the formula Het2, or a group represented by the formula Het3 (# 1 represents the binding site to Q), B 1 is NR 51a , or CR 61a R 61b represents B 2 is NR 51b , C.R. 61c R 61d , C.R. 61e R 61f -CR 61g R 61h -*, NR 51c -CR 61i R 61j - *, CR 61k R 61m -CR 61n R 61p -CR 61q R 61r -* or NR 51d -CR 61s R 61t -CR 61u R 61v - represents *, * is B 1 represents the bonding position with W 1 represents an oxygen atom or a sulfur atom, R 51a , R 51b , R 51c , and R 51d are the same or different, and the group K 2 a C1-C6 chain hydrocarbon group optionally substituted by one or more substituents selected from the above, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group optionally substituted by one or more halogen atoms, or a hydrogen atom; R 61a , R 61b , R 61c , R 61d , R 61e , R 61f , R 61g , R 61h , R 61i , R 61j , R 61k , R 61 , R 61m , R 61n , R 61p , R 61q , R 61r , R 61s , R 61t , R 61u , and R 61v are the same or different and are each a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a nitro group, OR 63 , N.R. 63 R 64 , a cyano group, a halogen atom, or a hydrogen atom; R 61a and R 61b , R 61c and R 61d , R 61e and R 61f , R 61g and R 61h , R 61i and R 61j , R 61k and R 61m , R 61n and R 61p , R 61q and R 61r , R 61s and R 61t , and R 61u and R 61v may each be taken together with the carbon atom to which they are attached to form a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom; R 63 is the group T 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group J 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of , R 64 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; X 1 is CR 62a or a nitrogen atom, X 2 is CR 62b or a nitrogen atom, X 3 is CR 62c or a nitrogen atom, Z 1 is NR 52a , an oxygen atom, or a sulfur atom; Z 2 is NR 52b , an oxygen atom, or a sulfur atom; Z 3 is NR 52c , an oxygen atom, or a sulfur atom; R 52a , R 52b , and R 52c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 73 , C(O)OR 74 , C(O)NR 91 R 92 , C(O)NR 71 S(O)2R 83 , C.R. 90 = NOR 77 , S(O) v R 83 or a hydrogen atom, R 62a , R 62b , and R 62c are the same or different, and the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 72 , N.R. 71 R 72 , N.R. 76a R 76b , N.R. 84 NR 71 R 72 , N.R. 84 OR 71 , N.R. 71 C(O)R 73 , N.R. 84 NR 71 C(O)R 73 , N.R. 71 C(O)OR 74 , N.R. 84 NR 71 C(O)OR 74 , N.R. 71 C(O)NR 91 R 92 , N.R. 84 NR 71 C(O)NR 91 R 92 , N=CHNR 91 R 92 , N=S(O) r R 75 R 76 , C(O)R 73 , C(O)OR 77 , C(O)NR 91 R 92 , C(O)NR 71 S(O)2R 83 , C.R. 90 = NOR 77 , N.R. 71 CR 84 = NOR 77 , S(O) t R 83 , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; r represents 0 or 1; t represents 0, 1 or 2; v represents 0, 1 or 2; R 71 , R 84 , R 96 and R 97 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 72 is the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of S(O)R 83 or a hydrogen atom, R 73 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally substituted with one or more halogen atoms, Group V 2 a phenyl group optionally substituted with one or more substituents selected from Group V 2 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: R 74 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of: R 75 and R 76 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, R 76a and R 76b together with the nitrogen atom to which they are attached, form the group P 2 and forming a 3- to 7-membered non-aromatic heterocyclic group which may be substituted by one or more substituents selected from the group consisting of R 77 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of: R 83 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group V 2 represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of R 90 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR 95 , N.R. 96 R 97 or a hydrogen atom, R 91 represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R 92 is the group P 2 a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from the group M 2 a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O)R 83 , or a hydrogen atom. R 95 represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. Group D: a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, NR 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 The group consisting of , a cyano group, a nitro group, and a halogen atom. R 101 and R 102 are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom. 　 Group E: a group consisting of C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxy groups, cyano groups, and nitro groups. Group F: C1-C6 alkoxy group optionally substituted with one or more halogen atoms, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of NR 101 R 102 , a halogen atom, and a cyano group. Group H: C1-C6 alkyl groups optionally substituted with one or more halogen atoms, Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR 104 , N.R. 103 R 104 , C(O)R 104 , C(O)NR 103 R 104 , O.C.(O.)R 103 , OC(O)OR 103 , N.R. 104 C(O)R 103 , N.R. 104 C(O)OR 103 , C(O)OR 104 The group consisting of halogen atoms, nitro groups, cyano groups, and amino groups. R 103 represents 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 104 represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. Group I: C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, Group D 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of C(O)R 103 , C(O)OR 103 , and C(O)NR 103 R 104 A group consisting of: Group J: A group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. Group L: a group consisting of C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C3-C6 alkenyloxy groups optionally substituted with one or more halogen atoms, C3-C6 alkynyloxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl groups optionally substituted with one or more halogen atoms, cyano groups, hydroxy groups, and halogen atoms. Group J 2 The group consisting of C1-C6 alkyl groups optionally substituted with one or more halogen atoms, halogen atoms, and cyano groups. Group K 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms, and a group M 3 The group consisting of 3- to 7-membered non-aromatic heterocyclic groups optionally substituted with one or more substituents selected from the following: Group M 2 The group consisting of C1-C6 alkyl groups optionally substituted with one or more halogen atoms, C1-C6 alkoxy groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups optionally substituted with one or more halogen atoms, and halogen atoms. Group T 2 Group D: a C1-C6 alkoxy group optionally substituted with one or more halogen atoms; 3 a phenyl group optionally substituted with one or more substituents selected from Group D 3 a 5- or 6-membered aromatic heterocyclic group optionally substituted by one or more substituents selected from the group consisting of: a C3-C7 cycloalkyl group optionally substituted by one or more halogen atoms; 3 a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of an amino group, NHR 101 , N.R. 101 R 102 , a halogen atom, and a cyano group. Group P 2 : Group U 3 the group consisting of a C3-C6 cycloalkyl group optionally substituted by one or more substituents selected from the above, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a hydroxy group, a sulfanyl group, a cyano group, a phenyl group, and a halogen atom. Group U 3 : A group consisting of C1-C3 alkyl groups and halogen atoms. Group V 2 The group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group optionally substituted with one or more halogen atoms, a di(C1-C6 alkyl)amino group optionally substituted with one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atoms, a hydroxy group, a sulfanyl group, an amino group, a cyano group, a nitro group, and a halogen atom. Group D 3 : a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group optionally substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atoms, an amino group, NHR 101 , N.R. 101 R 102 , C(O)R 101 , O.C.(O.)R 101 , C(O)OR 101 The group consisting of , a cyano group, a nitro group, and a halogen atom. Group M 3 The group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group optionally substituted with one or more halogen atoms, a C3-C2 alkynyloxy group optionally substituted with one or more halogen atoms, and a halogen atom. or an N-oxide thereof.

2. The compound according to claim 1, wherein Q is a group represented by the formula Q1, or an N-oxide thereof.

2. The compound of claim 1, wherein Q is a group represented by formula Q5, or an N-oxide thereof. Q is a group represented by formula Q1, and A 1 The compound according to claim 1 or an N-oxide thereof, wherein is a nitrogen atom. Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is a nitrogen atom or CR 10d 2. The compound of claim 1, wherein: Q is a group represented by formula Q5, and G 1 is CR 10a and G 2 is CR 10b and G 3 is CR 10c and G 4 is CR 10d 2. The compound of claim 1, wherein: 　 Het is a group represented by the formula Het1, and B 1 is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1 The compound or N-oxide thereof according to any one of claims 1 to 6, wherein is an oxygen atom. 　 Het is a group represented by the formula Het2, and B 1 is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1 The compound or N-oxide thereof according to any one of claims 1 to 6, wherein is an oxygen atom. 　 Het is a group represented by the formula Het3, and B 1 is CR 61a R 61b and B 2 is CR 61c R 61d or CR 61e R 61f -CR 61g R 61h -* and W 1 The compound or N-oxide thereof according to any one of claims 1 to 6, wherein is an oxygen atom. R 2 is an ethyl group, and W 1 The compound or N-oxide thereof according to any one of claims 1 to 9, wherein is an oxygen atom.

11. A composition for controlling arthropod pests, comprising the compound according to any one of claims 1 to 10 or an N-oxide 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 or N-oxide thereof according to any one of claims 1 to 10: 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, which comprises applying an effective amount of the compound or N-oxide thereof according to any one of claims 1 to 10, or an effective amount of the composition according to claim 12, to arthropod pests or to habitats of arthropod pests. 　 A seed or vegetative reproductive organ carrying an effective amount of the compound or N-oxide thereof according to any one of claims 1 to 10 or an effective amount of the composition according to claim 12.

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