Heterocyclic compound and harmful arthropod control composition containing same

Abstract

The present invention provides a compound that has excellent control effects on harmful arthropods. Compounds represented by formula (I) (the meanings of the symbols of which are described in the description) or N-oxides thereof have excellent control effects on harmful arthropods.

Description

Heterocyclic compound and pest control composition containing the same

[0001] This application claims priority to and the benefit of Japanese Patent Application No. 2022-177697 filed on November 4, 2022, Japanese Patent Application No. 2023-088026 filed on May 29, 2023, and Japanese Patent Application No. 2023-160980 filed on September 25, 2023, the entire contents of which are incorporated herein by reference. The present invention relates to a heterocyclic compound and a pest arthropod control composition 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 pest control effects.

[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) [Wherein, Q represented by the following formula (wherein # represents a bonding site to a sulfur atom, and ● represents a bonding site to Het) represents a group represented by formula Q1 or a group represented by formula Q2, A １ is a nitrogen atom or CR ８ represents R ８ represents a halogen atom or a hydrogen atom; ２ represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a cyclopropyl group, or a cyclopropylmethyl group, n represents 0, 1, or 2, G １ is a nitrogen atom or CR ３ａ represents ２ is a nitrogen atom or CR ３ｂ represents ３ is a nitrogen atom or CR ３ｃ represents ４ is a nitrogen atom or CR ３ｄ represents R ３ａ, R ３ｂ , R ３ｃ and R ３ｄ 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. １１ａ R １２ａ , 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) ２ R ２３ , C.R. ３０ = NOR １７ , N.R. １１ CR ２４ = NOR １７ , S(O) ｍ R ２３, a cyano group, a nitro group, a halogen atom, or a hydrogen atom; p represents 0 or 1; m represents 0, 1, or 2; 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 ３５ represents a C1-C6 chain hydrocarbon 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 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, S(O) ２ R ２３ or a hydrogen atom, 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 １１ａ and R １２ａ together with the nitrogen atom to which they are attached form a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group E, R １３represents 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 ３１ represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, 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, S(O) ２ R ２３ or a hydrogen atom, R ４ is the 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 a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of OR ４２ , N.R. ４１ R ４２ , N.R. ４１ａ R ４２ａ , N.R. ５４ NR４１ R ４２ , N.R. ５４ OR ４１ , N.R. ４１ C(O)R ４３ , N.R. ５４ NR ４１ C(O)R ４３ , N.R. ４１ C(O)OR ４４ , N.R. ５４ NR ４１ C(O)OR ４４ , N.R. ４１ C(O)NR ６１ R ６２ , N.R. ５４ NR ４１ C(O)NR ６１ R ６２ , N=CHNR ６１ R ６２ , N=S(O) ｒ R ４５ R ４６ , C(O)R ４３ , C(O)OR ４７ , C(O)NR ６１ R ６２ , C(O)NR ４１ S (O) ２ R ５３ , C.R. ６０ = NOR ４７ , N.R. ４１ CR ５４ = NOR ４７ , S(O) ｔ R ５３ , a cyano group, a nitro group, or a halogen atom; r represents 0 or 1; t represents 0, 1, or 2; R ６０ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, OR ６５ , N.R. ６６ R ６７ or a hydrogen atom, R ６５ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R ４７ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group D ２ R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of ４１, R ５４ , R ６６ and R ６７ 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 ４２ is the group F 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 D ２ a phenyl group optionally substituted with one or more substituents selected from Group D ２ a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a hydrogen atom and S(O) ２ R ５３ represents R ５３ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group D ２ R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of ４１ａ and R ４２ａ together with the nitrogen atom to which they are attached, form a group E ２ R ４３ 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 D ２ a phenyl group optionally substituted with one or more substituents selected from Group D ２ R represents a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: ４４represents 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 is selected from the group D ２ R may be substituted with one or more substituents selected from the following ４５ and R ４６ are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms; R ６１ represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R ６２ is the group F 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 the group consisting of S(O) ２ R ５３ or a hydrogen atom, k represents 0, 1, 2, or 3, and when k is 2 or 3, two or three R ４ may be the same or different, and two R ４ When R are bonded to adjacent carbon atoms, the two R ４ 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 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 pyridine ring, the pyridazine ring, the pyrimidine ring, and the pyrazine ring are each selected from the group H ２ Het represents a group represented by the formula Het1 or a group represented by the formula Het2, A ２ is -NR ５ａ - or -CR ７ａ R ７ｂ represents -, A ３ is -CR ７ｃ R ７ｄ -, -CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ , or -CR ７ｉ R ７ｊ -CR ７ｋ R ７ｌ -CR ７ｍ R ７ｎ -* １ represents * １ Is A ２ represents the bonding position with A ４ is -NR ５ｂ -, -CR ７ｏ R ７ｐ -, -CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ , -NR ５ｃ -CR ７ｕ R ７ｖ -* ２ , -CR ７ｗ R ７ｘ -CR ７ｙ R ７ｚ -CR ７ａａ R ７ｂｂ -* ２ , or -NR ５ｄ -CR ７ｃｃ R ７ｄｄ -CR ７ｅｅ R ７ｆｆ -* ２ represents * ２ is A ２ represents the bonding position with ５ａ , R ５ｂ , R ５ｃ , and R ５ｄare the same or different and represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group K, 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 ７ａ , R ７ｂ , R ７ｃ , R ７ｄ , R ７ｅ , R ７ｆ , R ７ｇ , R ７ｈ , R ７ｉ , R ７ｊ , R ７ｋ , R ７ｌ , R ７ｍ , R ７ｎ , R ７ｏ , R ７ｐ , R ７ｑ , R ７ｒ , R ７ｓ , R ７ｔ , R ７ｕ , R ７ｖ , R ７ｗ , R ７ｘ , R ７ｙ , R ７ｚ , R ７ａａ , R ７ｂｂ , R ７ｃｃ , R ７ｄｄ , R ７ｅｅ , and R ７ｆｆ 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 ６９ , N.R. ６９ R ７０ , a cyano group, a halogen atom, or a hydrogen atom; R ７ａ and R ７ｂ , R ７ｃ and R ７ｄ , R ７ｅ and R ７ｆ , R ７ｇ and R ７ｈ , R ７ｉ and R７ｊ , R ７ｋ and R ７ｌ , R ７ｍ and R ７ｎ , R ７ｏ and R ７ｐ , R ７ｑ and R ７ｒ , R ７ｓ and R ７ｔ , R ７ｕ and R ７ｖ , R ７ｗ and R ７ｘ , R ７ｙ and R ７ｚ , R ７ａａ and R ７ｂｂ , R ７ｃｃ and R ７ｄｄ , and R ７ｅｅ and R ７ｆｆ 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 ６９ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group T, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group U, a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group U, a phenyl group optionally substituted with one or more substituents selected from Group V, a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from Group V, or a hydrogen atom; R ７０ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a hydrogen atom; W represents an oxygen atom or a sulfur atom; B １ is CR ６ａ or a nitrogen atom, B ２ is CR ６ｂ or a nitrogen atom, B ３ is CR ６ｃ or a nitrogen atom, R ６ａ , R ６ｂ , and R ６ｃ are the same or different, and the group L ３ a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from Group E ３a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from group H ３ a phenyl group optionally substituted with one or more substituents selected from group H ３ 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. ７１ａ R ７２ａ , 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) ｑ R ７５ R ７６ , C(O)R ７３ , C(O)OR ７７ , C(O)NR ９１ R ９２ , C(O)NR ７１ S (O) ２ R ８３ , C.R. ９０ = NOR ７７ , N.R. ７１ CR ８４ = NOR ７７ , S(O) ｖ R ８３ , a cyano group, a nitro group, a halogen atom, or a hydrogen atom; q represents 0 or 1; v represents 0, 1, or 2; R ９０represents 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 ９５ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, R ７７ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms; Group D ３ R represents a phenyl group optionally substituted with one or more substituents selected from the group consisting of 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 F ３ a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group J ３ a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from Group J ３ a C3-C7 cycloalkenyl group optionally substituted with one or more substituents selected from Group D ３ a phenyl group optionally substituted with one or more substituents selected from Group D ３ a 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of S(O) ２ R ８３ or a hydrogen atom, R ８３ represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or a group D ３ R represents a phenyl group which may be substituted with one or more substituents selected from the group consisting of ７１ａ and R ７２ａ together with the nitrogen atom to which they are attached, form a group E ３ R ７３represents 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 D ３ a phenyl group optionally substituted with one or more substituents selected from Group D ３ 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, 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 is selected from the group D ３ R may be substituted with one or more substituents selected from the following 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 ９１ represents a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a hydrogen atom; R ９２ is the group F ３ a C1-C6 chain hydrocarbon group optionally substituted with one or more substituents selected from group J ３ a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of S(O) ２ R ８３or a hydrogen atom. Group L: a group consisting of 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 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 C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom. Group M: 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, and a halogen atom. 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, an amino group, NHR ２１ , N.R. ２１ R ２２ , C(O)R ２１ , O.C.(O.)R ２１ , C(O)OR ２１ , a cyano group, a nitro group, and a halogen atom. ２１ and R ２２are the same or different and represent a C1-C6 alkyl group optionally substituted with one or more halogen atoms. 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, 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, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group M, an amino group, NHR ２１ , N.R. ２１ R ２２ , a halogen atom, and a cyano group. Group H: a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR １０ , N.R. ９ R １０ , C(O)R １０ , C(O)NR ９ R １０ , O.C.(O.)R ９ , OC(O)OR ９ , N.R. １０ C(O)R ９ , N.R. １０ C(O)OR ９ , C(O)OR １０ a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group W. ９ 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 １０represents 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 P: a C2-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 ２ a phenyl group optionally substituted with one or more substituents selected from Group D ２ 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 K: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic 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, an aminocarbonyl group, a (C1-C6 alkyl)aminocarbonyl group optionally substituted with one or more halogen atoms, a methyl group, and a di(C1-C4 alkyl)aminocarbonyl group optionally substituted with one or more halogen atoms. 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 K: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atoms, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, and a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more halogen atoms. Group T: a C1-C6 alkoxy 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, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from Group M, an amino group, NHR 21 , N.R. 21 R 22, a halogen atom, and a cyano group. Group U: 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 V: 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 21 , N.R. 21 R 22 , C(O)R 21 , O.C.(O.)R 21 , C(O)OR 21 Group W: 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 ２１ , N.R. ２１ R ２２ , C(O)R ２１ , O.C.(O.)R ２１ , C(O)OR ２１ a group consisting of a cyano group, a nitro group, and a halogen atom; ２Group D: a group consisting of 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 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 C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom. ２ : 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 ２１ , N.R. ２１ R ２２ , C(O)R ２１ , O.C.(O.)R ２１ , C(O)OR ２１ a group consisting of a cyano group, a nitro group, and a halogen atom. ２ Group F: 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. ２a C1-C6 alkoxy 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, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from group M, an amino group, NHR ２１ , N.R. ２１ R ２２ , a halogen atom, and a cyano group. ２ : a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR １０ , N.R. ９ R １０ , C(O)R １０ , C(O)NR ９ R １０ , O.C.(O.)R ９ , OC(O)OR ９ , N.R. １０ C(O)R ９ , N.R. １０ C(O)OR ９ , C(O)OR １０ a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group W. ２ Group L: A group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group. ３ Group D: a group consisting of 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 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 C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, a cyano group, a hydroxy 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 ２１ , N.R. ２１ R ２２ , C(O)R ２１ , O.C.(O.)R ２１ , C(O)OR ２１ a group consisting of a cyano group, a nitro group, and a halogen atom. ３ Group F: 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. ３ a C1-C6 alkoxy 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, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atoms, a 3- to 7-membered non-aromatic heterocyclic group optionally substituted with one or more substituents selected from group M, an amino group, NHR ２１ , N.R. ２１ R ２２ , a halogen atom, and a cyano group. ３ : a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR １０ , N.R. ９ R １０ , C(O)R １０ , C(O)NR ９ R１０ , O.C.(O.)R ９ , OC(O)OR ９ , N.R. １０ C(O)R ９ , N.R. １０ C(O)OR ９ , C(O)OR １０ a halogen atom, a nitro group, a cyano group, an amino group, and a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from group W. ３ a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group.] (hereinafter referred to as compound N of the present invention) or an N-oxide thereof (hereinafter, the compound represented by formula (I) or an N-oxide thereof will be referred to as compound of the present invention). [2] The compound according to [1] or an N-oxide thereof, wherein Q is a group represented by formula Q1. [3] The compound according to [1] or an N-oxide thereof, wherein Q is a group represented by formula Q2. [4] Q is a group represented by formula Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ [5] The compound according to [1] or an N-oxide thereof, wherein Q is a group represented by the formula Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ [6] The compound according to [1] or an N-oxide thereof, wherein Q is a group represented by the formula Q2, and A １ [7] The compound according to [1], wherein Q is a group represented by formula Q2, and A is an N-oxide thereof. １ is CR ８ [8] The compound according to [1] or an N-oxide thereof, wherein Het is a group represented by the formula Het1, and A ２ Ga-CR ７ａ R ７ｂ- and A ３ Ga-CR ７ｃ R ７ｄ -or-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ [9] The compound according to any one of [1] to [7], wherein W is an oxygen atom, or an N-oxide thereof. ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｏ R ７ｐ -or-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ and W is an oxygen atom.

[10] A composition for controlling arthropod pests, comprising the compound or N-oxide thereof according to any one of [1] to [9] and an inert carrier.

[11] A composition comprising one or more components selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the compound or N-oxide thereof according to any one of [1] to [9]: 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.

[12] 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 [9] or an effective amount of the composition according to

[11] to arthropod pests.

[13] 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 [9], or an effective amount of the composition according to

[11] .

[14] A compound represented by formula (II) [In the formula, X １ represents a chlorine atom, a bromine atom, an iodine atom, or a hydroxy group, and other symbols have the same meanings as in [1].] or a salt thereof (hereinafter, the compound represented by formula (II) or a salt thereof will be referred to as intermediate A).

[15] Formula (III) [In the formula, X ２represents a chlorine atom, a bromine atom, an iodine atom, or a hydroxy group, and other symbols have the same meanings as in [1].] or a salt thereof (hereinafter, the compound represented by formula (III) or a salt thereof will be referred to as intermediate B).

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

[0007] The substituents used in the present invention will be explained. A halogen atom refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom. When a substituent 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 notation "CX-CY" means that the number of carbon atoms is X to Y. For example, the notation "C1-C6" means that the number of carbon atoms is 1 to 6. The chain hydrocarbon group represents an alkyl group, an alkenyl group, or an alkynyl group. Examples of alkyl groups include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 1,1-dimethylpropyl group, a 1,2-dimethylpropyl group, a 1-ethylpropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. Examples of alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1-ethyl-2-propenyl, 3-butenyl, 4-pentenyl, and 5-hexenyl. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-butynyl, 4-pentynyl, and 5-hexynyl. Examples of alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, and hexyloxy. Examples of 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.

[0008] Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. Examples of cycloalkenyl groups include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl groups.

[0009] 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. 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 the (C3-C7 cycloalkyl) and / or (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. Phenyl C1-C3 alkyl groups (the phenyl moiety in the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from Group D) and phenyl C1-C3 alkyl groups (the phenyl moiety in the phenyl C1-C3 alkyl group is a group selected from Group D). ２ and a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may be selected from the group D ３Examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, and an isopropylsulfanyl group. Examples of alkylsulfinyl groups include a methylsulfinyl group, an ethylsulfanyl group, a propylsulfinyl group, and an isopropylsulfinyl group. Examples of alkylsulfonyl groups include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and an isopropylsulfonyl group. Examples of alkylcarbonyl groups include an acetyl group, a propanoyl group, a 2-methylpropanoyl group, and a hexanoyl group. Examples of alkoxycarbonyl groups include methoxycarbonyl groups, ethoxycarbonyl groups, isopropoxycarbonyl groups, and pentyloxycarbonyl groups. Examples of (C1-C6 alkyl)aminocarbonyl groups optionally substituted with one or more halogen atoms include methylaminocarbonyl groups, trifluoromethylaminocarbonyl groups, isopropylaminocarbonyl groups, and hexylaminocarbonyl groups. Examples of di(C1-C4 alkyl)aminocarbonyl groups optionally substituted with one or more halogen atoms include dimethylaminocarbonyl groups, methylethylaminocarbonyl groups, trifluoromethylethylaminocarbonyl groups, and diisopropylaminocarbonyl groups.

[0010] Examples of the N-oxide of the compound of formula (I) include the compounds of the following formula: (wherein the symbols have the same meanings as defined above.)

[0011] 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.

[0012] The compound of the present invention, the compound represented by formula (II), and the compound represented by formula (III) 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, the compound represented by formula (II), or the compound represented by formula (III) with an acid.

[0013] The following compounds are examples of the compound N of the present invention: [Aspect 1] A compound of the present invention in which W is an oxygen atom. [Aspect 2] A compound of the present invention in which R ２ is a C1-C6 alkyl group. ２ is an ethyl group. [Aspect 4] A compound of the present invention, in which Q is a group represented by Q1. [Aspect 5] A compound of the present invention, in which Q is a group represented by Q2. [Aspect 6] A compound of the present invention, in which Het is a group represented by Het1. [Aspect 7] A compound of the present invention, in which Het is a group represented by Het2. [Aspect 8] A compound of the present invention, in which Q is a group represented by Q1, and G １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G ３ is CR ３ｃ and G ４ is CR３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, or a halogen atom. [Embodiment 9] A compound in which, in compound N of the present invention, Q is a group represented by Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. [Embodiment 10] A compound N of the present invention, wherein Q is a group represented by Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ, R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. [Embodiment 11] A compound of the present invention, wherein Q is a group represented by Q1, and G １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G ３ is CR ３ｃ and G ４ is CR ３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Embodiment 12] In the compound N of the present invention, Q is a group represented by Q1, and G １ is CR３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Embodiment 13] In the compound N of the present invention, Q is a group represented by Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Embodiment 14] In the compound N of the present invention, Q is a group represented by Q2, and A １ is a nitrogen atom. [Embodiment 15] In the compound N of the present invention, Q is a group represented by Q2, and A １ is CR ８ [Embodiment 16] In the compound N of the present invention, Q is a group represented by Q2, and R ４ 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 A compound in which Q is 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. １ is a nitrogen atom or CR ８ where k is 2 and two R ４ are adjacent, and two R ４together with the two carbon atoms to which they are attached, form a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring {the benzene ring, the pyridine ring, the pyridazine ring, the pyrimidine ring, and the pyrazine ring are each a ring selected from the group H ２ [Embodiment 18] In the compound N of the present invention, Q is a group represented by Q2, and R ４ 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 A compound of the present invention, wherein G is a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of: １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom, and A １ is a nitrogen atom, k is 0 or 1, and R ４ is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, or a halogen atom. [Embodiment 20] A compound of the present invention N, wherein Q is a group represented by Q1, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄis a hydrogen atom, and R ３ｂ is a halogen atom. [Embodiment 21] In the compound N of the present invention, Q is a group represented by Q2, and A １ is a nitrogen atom, k is 0 or 1, and R ４ is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, or a halogen atom. [Embodiment 22] A compound of the present invention, wherein Q is a group represented by Q2, and A １ is a nitrogen atom, k is 0 or 1, and R ４ is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, or a pyrimidinyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom. [Embodiment 23] A compound of the present invention, wherein Q is a group represented by Q2, and A １ is a nitrogen atom, k is 0 or 1, and R ４ is a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, or a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom. １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom, and A １ is a nitrogen atom, k is 0 or 1, and R ４a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , N.R. ４１ C(O)OR ４４ or a halogen atom. [Embodiment 25] In the compound N of the present invention, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom, and A １ is a nitrogen atom, k is 0 or 1, and R ４ a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , or NR ４１ C(O)OR ４４ and R ４１ is a C1-C6 alkyl group or a hydrogen atom, and R ４２ is a hydrogen atom, and R ４３ is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, and R ４４ is a C1-C6 alkyl group. [Embodiment 26] In the compound N of the present invention, Q is a group represented by Q2, and A １ is a nitrogen atom, k is 0 or 1, and R ４a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , N.R. ４１ C(O)OR ４４ or a halogen atom. [Embodiment 27] In the compound N of the present invention, Q is a group represented by Q2, and A １ is a nitrogen atom, k is 0 or 1, and R ４ a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , or NR ４１ C(O)OR ４４ and R ４１ is a C1-C6 alkyl group or a hydrogen atom, and R ４２ is a hydrogen atom, and R ４３ is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, and R ４４ is a C1-C6 alkyl group. [Embodiment 28] Compound N of the present invention, wherein Q is a group represented by Q1 or a group represented by formula Q2a and G is a group represented by １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom, and A １ is a nitrogen atom, ka is 0 or 1, and R ４ｂa phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , N.R. ４１ C(O)OR ４４ or a halogen atom. [Embodiment 29] In the compound N of the present invention, Q is a group represented by Q1 or a group represented by the above formula Q2a, and G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom, and A １ is a nitrogen atom, ka is 0 or 1, and R ４ｂ a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , or NR ４１ C(O)OR ４４ and R ４１ is a C1-C6 alkyl group or a hydrogen atom, and R ４２ is a hydrogen atom, and R ４３ is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, and R ４４ is a C1-C6 alkyl group. [Embodiment 30] In the compound N of the present invention, Q is a group represented by the above formula Q2a, and A １ is a nitrogen atom, ka is 0 or 1, and R ４ｂa phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a C3-C7 cycloalkyl group, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , N.R. ４１ C(O)OR ４４ or a halogen atom. [Embodiment 31] In the compound N of the present invention, Q is a group represented by the above formula Q2a, and A １ is a nitrogen atom, ka is 0 or 1, and R ４ｂ a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , or NR ４１ C(O)OR ４４ and R ４１ is a C1-C6 alkyl group or a hydrogen atom, and R ４２ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms or a hydrogen atom, and R ４３ is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, and R ４４ is a C1-C6 alkyl group. [Embodiment 32] In the compound N of the present invention, Q is a group represented by the above formula Q2a, and A １ is a nitrogen atom, ka is 0 or 1, and R ４ｂ a phenyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, a pyridyl group optionally substituted with one or more substituents selected from the group consisting of a cyano group and a halogen atom, OR ４２ , N.R. ４１ R ４２ , N.R. ４１ C(O)R ４３ , or NR ４１ C(O)OR４４ and R ４１ is a C1-C6 alkyl group or a hydrogen atom, and R ４２ is a hydrogen atom, and R ４３ is a C1-C6 alkyl group or a C3-C7 cycloalkyl group, and R ４４is a C1-C6 alkyl group. [Aspect 33] A compound in Aspect 2, wherein W is an oxygen atom. [Aspect 34] A compound in Aspect 3, wherein W is an oxygen atom. [Aspect 35] A compound in Aspect 4, wherein W is an oxygen atom. [Aspect 36] A compound in Aspect 5, wherein W is an oxygen atom. [Aspect 37] A compound in Aspect 6, wherein W is an oxygen atom. [Aspect 38] A compound in Aspect 7, wherein W is an oxygen atom. [Aspect 39] A compound in Aspect 8, wherein W is an oxygen atom. [Aspect 40] A compound in Aspect 9, wherein W is an oxygen atom. [Aspect 41] A compound in Aspect 10, wherein W is an oxygen atom. [Aspect 42] A compound in Aspect 11, wherein W is an oxygen atom. [Aspect 43] A compound in Aspect 12, wherein W is an oxygen atom. [Aspect 44] A compound in Aspect 13, wherein W is an oxygen atom. [Aspect 45] A compound in Aspect 14, wherein W is an oxygen atom. [Aspect 46] A compound in Aspect 15, wherein W is an oxygen atom. [Aspect 47] A compound in Aspect 16, wherein W is an oxygen atom. [Aspect 48] A compound in Aspect 17, wherein W is an oxygen atom. [Aspect 49] A compound in Aspect 18, wherein W is an oxygen atom. [Aspect 50] A compound in Aspect 19, wherein W is an oxygen atom. [Aspect 51] A compound in Aspect 20, wherein W is an oxygen atom. [Aspect 52] A compound in Aspect 21, wherein W is an oxygen atom. [Aspect 53] A compound in Aspect 22, wherein W is an oxygen atom. [Aspect 54] A compound in Aspect 23, wherein W is an oxygen atom. [Aspect 55] A compound in Aspect 24, wherein W is an oxygen atom. [Aspect 56] A compound in Aspect 25, wherein W is an oxygen atom. [Aspect 57] A compound in Aspect 26, wherein W is an oxygen atom. [Aspect 58] A compound in Aspect 27, wherein W is an oxygen atom. [Aspect 59] A compound in Aspect 28, wherein W is an oxygen atom. [Aspect 60] A compound in Aspect 29, wherein W is an oxygen atom. [Aspect 61] A compound in Aspect 30, wherein W is an oxygen atom. [Aspect 62] A compound in Aspect 31, wherein W is an oxygen atom. [Aspect 63] A compound in Aspect 32, wherein W is an oxygen atom. [Aspect 64] A compound in Aspect 4, wherein R ２ is a C1-C6 alkyl group. ２is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group.２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl group. ２ is a C1-C6 alkyl 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. 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. [Embodiment 122] In embodiment 4, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 123] In aspect 5, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 124] In aspect 6, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 125] In embodiment 7, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 126] In aspect 8, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 127] In aspect 9, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 128] In embodiment 10, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 129] In aspect 11, W is an oxygen atom, and R ２is an ethyl group. [Aspect 130] In aspect 12, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 131] In aspect 13, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 132] In embodiment 14, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 133] In embodiment 15, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 134] In embodiment 16, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 135] In aspect 17, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 136] In embodiment 18, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 137] In embodiment 19, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 138] In embodiment 20, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 139] In aspect 21, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 140] In aspect 22, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 141] In aspect 23, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 142] In aspect 24, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 143] In embodiment 25, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 144] In embodiment 26, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 145] In embodiment 27, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 146] In embodiment 28, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 147] In embodiment 29, W is an oxygen atom, and R ２ is an ethyl group. [Embodiment 148] In embodiment 30, W is an oxygen atom, and R２ is an ethyl group. [Embodiment 149] In embodiment 31, W is an oxygen atom, and R ２ is an ethyl group. [Aspect 150] In aspect 32, W is an oxygen atom, and R ２is an ethyl group. [Aspect 151] A compound in Aspect 6, wherein Q is a group represented by Q1. [Aspect 152] A compound in Aspect 7, wherein Q is a group represented by Q1. [Aspect 153] A compound in Aspect 6, wherein Q is a group represented by Q2. [Aspect 154] A compound in Aspect 7, wherein Q is a group represented by Q2. [Aspect 155] A compound in Aspect 8, wherein Het is a group represented by Het1. [Aspect 156] A compound in Aspect 9, wherein Het is a group represented by Het1. [Aspect 157] A compound in Aspect 10, wherein Het is a group represented by Het1. [Aspect 158] A compound in Aspect 11, wherein Het is a group represented by Het1. [Aspect 159] A compound in Aspect 12, wherein Het is a group represented by Het1. [Aspect 160] A compound in Aspect 13, wherein Het is a group represented by Het1. [Aspect 161] A compound in Aspect 14, wherein Het is a group represented by Het1. [Aspect 162] A compound in Aspect 15, wherein Het is a group represented by Het1. [Aspect 163] A compound in Aspect 16, wherein Het is a group represented by Het1. [Aspect 164] A compound in Aspect 17, wherein Het is a group represented by Het1. [Aspect 165] A compound in Aspect 18, wherein Het is a group represented by Het1. [Aspect 166] A compound in Aspect 19, wherein Het is a group represented by Het1. [Aspect 167] A compound in Aspect 20, wherein Het is a group represented by Het1. [Aspect 168] A compound in Aspect 21, wherein Het is a group represented by Het1. [Aspect 169] A compound in Aspect 22, wherein Het is a group represented by Het1. [Aspect 170] A compound in Aspect 23, wherein Het is a group represented by Het1. [Aspect 171] A compound in Aspect 24, wherein Het is a group represented by Het1. [Aspect 172] A compound in Aspect 25, wherein Het is a group represented by Het1. [Aspect 173] A compound in Aspect 26, wherein Het is a group represented by Het1. [Aspect 174] A compound in Aspect 27, wherein Het is a group represented by Het1. [Aspect 175] A compound in Aspect 28, wherein Het is a group represented by Het1. [Aspect 176] A compound in Aspect 29, wherein Het is a group represented by Het1.[Aspect 177] A compound in Aspect 30, wherein Het is a group represented by Het1. [Aspect 178] A compound in Aspect 31, wherein Het is a group represented by Het1. [Aspect 179] A compound in Aspect 32, wherein Het is a group represented by Het1. [Aspect 180] A compound in Aspect 8, wherein Het is a group represented by Het2. [Aspect 181] A compound in Aspect 9, wherein Het is a group represented by Het2. [Aspect 182] A compound in Aspect 10, wherein Het is a group represented by Het2. [Aspect 183] A compound in Aspect 11, wherein Het is a group represented by Het2. [Aspect 184] A compound in Aspect 12, wherein Het is a group represented by Het2. [Aspect 185] A compound in Aspect 13, wherein Het is a group represented by Het2. [Aspect 186] A compound in Aspect 14, wherein Het is a group represented by Het2. [Aspect 187] A compound in Aspect 15, wherein Het is a group represented by Het2. [Aspect 188] A compound in Aspect 16, wherein Het is a group represented by Het2. [Aspect 189] A compound in Aspect 17, wherein Het is a group represented by Het2. [Aspect 190] A compound in Aspect 18, wherein Het is a group represented by Het2. [Aspect 191] A compound in Aspect 19, wherein Het is a group represented by Het2. [Aspect 192] A compound in Aspect 20, wherein Het is a group represented by Het2. [Aspect 193] A compound in Aspect 21, wherein Het is a group represented by Het2. [Aspect 194] A compound in Aspect 22, wherein Het is a group represented by Het2. [Aspect 195] A compound in Aspect 23, wherein Het is a group represented by Het2. [Aspect 196] A compound in Aspect 24, wherein Het is a group represented by Het2. [Aspect 197] A compound in Aspect 25, wherein Het is a group represented by Het2. [Aspect 198] A compound in Aspect 26, wherein Het is a group represented by Het2. [Aspect 199] A compound in Aspect 27, wherein Het is a group represented by Het2. [Aspect 200] A compound in Aspect 28, wherein Het is a group represented by Het2. [Aspect 201] A compound in Aspect 29, wherein Het is a group represented by Het2. [Aspect 202] A compound in Aspect 30, wherein Het is a group represented by Het2.[Aspect 203] The compound according to Aspect 31, wherein Het is a group represented by Het2. [Aspect 204] The compound according to Aspect 32, wherein Het is a group represented by Het2. [Aspect 205] In any one of Aspects 1 to 5, Aspects 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B. １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ and B is a nitrogen atom. [Embodiment 206] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ , R ６ｂ , and R ６ｃ are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; OR ７２ or a hydrogen atom. [Embodiment 207] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ａ is a hydrogen atom, and R ６ｂ and R ６ｃ are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Embodiment 208] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｃ is a hydrogen atom. [Embodiment 209] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃand R ６ｂ is a hydrogen atom, and R ６ｃ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Embodiment 210] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ and R ６ａ and R ６ｃ are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Embodiment 211] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Embodiment 212] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａis 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｂ is a hydrogen atom. [Embodiment 213] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ , R ６ｂ , and R ６ｃ are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; OR ７２ or a hydrogen atom. [Embodiment 214] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂis 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Embodiment 215] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - combination; A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ A is a combination of ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Embodiment 216] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-CR７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Embodiment 217] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and A ２ and A ４ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｏ R ７ｐ - combination; A ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ (* ２ is A ２ A is a combination of ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-NR ５ｃ -CR ７ｕ R ７ｖ -* ２ (* ２ is A ２ A is a combination of ２ Ga-NR ５ａ - and A ４ Ga-CR ７ｏ R ７ｐ -; or A ２ Ga-NR ５ａ - and A ４ Ga-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ (* ２ is A ２[Embodiment 218] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and A ２ and A ４ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｏ R ７ｐ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ (* ２ is A ２ [Embodiment 219] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ and R ７ａ , R ７ｂ , R ７ｃ , R ７ｄ , R ７ｅ , R ７ｆ , R ７ｇ , and R ７ｈare the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Embodiment 220] A compound in any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, wherein Het is a group represented by Het1, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ and R ７ｂ , and R ７ｃ and R ７ｄ may each be taken together with the carbon atom to which they are attached to form a C3-C4 cycloalkyl group, or Het is a group represented by Het1, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ represents the bonding position with R ７ａ and R ７ｂ , R ７ｅ and R ７ｆ , and R ７ｇ and R ７ｈ and A may each, together with the carbon atom to which they are attached, form a C3-C4 cycloalkyl group. [Embodiment 221] In any of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and A ２ and A ４ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｏ R ７ｐ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -*２ (* ２ is A ２ and R ７ａ , R ７ｂ , R ７ｏ , R ７ｐ , R ７ｑ , R ７ｒ , R ７ｓ , and R ７ｔ are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Embodiment 222] A compound in any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, wherein Het is a group represented by Het2, and A ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｏ R ７ｐ - and R ７ａ and R ７ｂ , and R ７ｏ and R ７ｐ may each be taken together with the carbon atom to which they are attached to form a C3-C4 cycloalkyl group, or Het is a group represented by Het2, and A ２ Ga-CR ７ａ R ７ｂ - and A ４ Ga-CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ -* ２ (* ２ is A ２ represents the bonding position with R ７ａ and R ７ｂ , R ７ｑ and R ７ｒ , and R ７ｓ and R ７ｔ and B may form a C3-C4 cycloalkyl group together with the carbon atom to which they are attached. [Embodiment 223] In any of Embodiments 1 to 5, 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Embodiment 224] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het2, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Embodiment 225] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, a halogen atom, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Embodiment 226] A compound according to any one of Embodiments 1 to 5, Embodiments 8 to 154, and Compound N of the present invention, wherein Het is a group represented by Het2, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂis 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 substituents selected from the group consisting of a halogen atom and a cyano group, a halogen atom, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Embodiment 227] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Embodiment 228] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Embodiment 229] In any one of Embodiments 1 to 5, Embodiments 8 to 154, or Compound N of the present invention, Het is a group represented by Het1, and B １ is CR ６ａ , B ２ is CR ６ｂ , B ３is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, OR ７２ or a halogen atom, R ７２ is a C1-C6 alkyl group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ A compound in which is a hydrogen atom.

[0014] The embodiments of intermediate A include the following compounds: [Embodiment A1] A compound in which W is an oxygen atom in intermediate A. [Embodiment A2] A compound in which R ２ is a C1-C6 alkyl group. [Aspect A3] Intermediate A, wherein R ２ is an ethyl group. [Aspect A4] Intermediate A, wherein X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A5] A compound in which, in intermediate A, X １ is a hydroxy group. [Aspect A6] Intermediate A, wherein G １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G３ is CR ３ｃ and G ４ is CR ３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect A7] A compound in which, in intermediate A, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect A8] A compound in which, in intermediate A, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄand R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G ３ is CR ３ｃ and G ４ is CR ３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect A10] A compound in which, in intermediate A, G １ is CR ３ａ and G２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect A11] A compound in which, in intermediate A, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect A12] A compound in which, in intermediate A, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂis a halogen atom. [Aspect A13] A compound in Aspect A2, in which W is an oxygen atom. [Aspect A14] A compound in Aspect A3, in which W is an oxygen atom. [Aspect A15] A compound in Aspect A4, in which W is an oxygen atom. [Aspect A16] A compound in Aspect A5, in which W is an oxygen atom. [Aspect A17] A compound in Aspect A6, in which W is an oxygen atom. [Aspect A18] A compound in Aspect A7, in which W is an oxygen atom. [Aspect A19] A compound in Aspect A8, in which W is an oxygen atom. [Aspect A20] A compound in Aspect A9, in which W is an oxygen atom. [Aspect A21] A compound in Aspect A10, in which W is an oxygen atom. [Aspect A22] A compound in Aspect A11, in which W is an oxygen atom. [Aspect A23] A compound in Aspect A12, in which W is an oxygen atom. [Aspect A24] A compound in Aspect A4, in which R ２ is a C1-C6 alkyl group. [Aspect A25] In Aspect A5, R ２ is a C1-C6 alkyl group. [Aspect A26] In Aspect A6, R ２ is a C1-C6 alkyl group. [Aspect A27] In Aspect A7, R ２ is a C1-C6 alkyl group. [Aspect A28] In Aspect A8, R ２ is a C1-C6 alkyl group. [Aspect A29] In Aspect A9, R ２ is a C1-C6 alkyl group. [Aspect A30] In Aspect A10, R ２ is a C1-C6 alkyl group. [Aspect A31] In aspect A11, R ２ is a C1-C6 alkyl group. [Aspect A32] In Aspect A12, R ２ is a C1-C6 alkyl group. [Aspect A33] In Aspect A4, R ２ is an ethyl group. [Aspect A34] A compound in which R ２ is an ethyl group. [Aspect A35] A compound in which R ２ is an ethyl group. [Aspect A36] A compound in which R ２ is an ethyl group. [Aspect A37] In Aspect A8, R ２is an ethyl group. [Aspect A38] In Aspect A9, R ２ is an ethyl group. [Aspect A39] A compound in which R ２ is an ethyl group. [Aspect A40] In aspect A11, R ２ is an ethyl group. [Aspect A41] A compound in aspect A12, wherein R ２ is an ethyl group. [Aspect A42] In aspect A4, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A43] In aspect A5, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A44] In aspect A6, W is an oxygen atom, and R ２ [Aspect A45] In aspect A7, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A46] In aspect A8, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A47] In aspect A9, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A48] In aspect A10, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A49] In aspect A11, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A50] In aspect A12, W is an oxygen atom, and R ２ is an ethyl group. [Aspect A51] A compound according to Aspect A6, wherein X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A52] In Aspect A7, X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A53] In Aspect A8, X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A54] In Aspect A9, X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A55] In Aspect A10, X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A56] In aspect A11, X １is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A57] In Aspect A12, X １ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect A58] In Aspect A6, X １ is a hydroxy group. [Aspect A59] In Aspect A7, X １ is a hydroxy group. [Aspect A60] A compound according to Aspect A8, wherein X １ is a hydroxy group. [Aspect A61] A compound according to Aspect A9, wherein X １ is a hydroxy group. [Aspect A62] In Aspect A10, X １ is a hydroxy group. [Aspect A63] In aspect A11, X １ is a hydroxy group. [Aspect A64] In Aspect A12, X １ is a hydroxy group. [Aspect A65] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ and B are nitrogen atoms. [Aspect A66] In any of Aspects A1 to A64 or Intermediate A, B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ , R ６ｂ , and R ６ｃ are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; OR ７２ or a hydrogen atom. [Aspect A67] In any of Aspects A1 to A64 or Intermediate A, B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ａ is a hydrogen atom, and R ６ｂ and R ６ｃ are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Aspect A68] In any of Aspects A1 to A64 or Intermediate A, B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ｂis 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｃ is a hydrogen atom. [Aspect A69] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ｂ is a hydrogen atom, and R ６ｃ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Aspect A70] In any of Aspects A1 to A64 or Intermediate A, B １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ and R ６ａ and R ６ｃ are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Aspect A71] In any of Aspects A1 to A64 or Intermediate A, B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Aspect A72] In any of Aspects A1 to A64 or Intermediate A, B １ is CR６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｂ is a hydrogen atom. [Aspect A73] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - combination; A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ A is a combination of ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Aspect A74] In any of Aspects A1 to A64 or Intermediate A, A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃR ７ｄ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Aspect A75] In any of Aspects A1 to A64 or Intermediate A, A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ and R ７ａ , R ７ｂ , R ７ｃ , R ７ｄ , R ７ｅ , R ７ｆ , R ７ｇ , and R ７ｈ are the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect A76] A compound in any of Aspects A1 to A64 or Intermediate A, wherein A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ and R ７ｂ , and R ７ｃ and R ７ｄ may each be taken together with the carbon atom to which they are attached to form a C3-C4 cycloalkyl group, or A２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ represents the bonding position with R ７ａ and R ７ｂ , R ７ｅ and R ７ｆ , and R ７ｇ and R ７ｈ may each, together with the carbon atom to which they are attached, form a C3-C4 cycloalkyl group. [Aspect A77] A compound in any of Aspects A1 to A64 or Intermediate A, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Aspect A78] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect A79] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect A80] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 alkyl group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect A81] A compound in any one of Aspects A1 to A64 or Intermediate A, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom.

[0015] The embodiments of intermediate B include the following compounds: [Embodiment B1] A compound in which W is an oxygen atom in intermediate B. [Embodiment B2] A compound in which R ２ is a C1-C6 alkyl group. [Aspect B3] In intermediate B, R ２ [Aspect B4] A compound in which X in intermediate B is an ethyl group. ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B5] In intermediate B, X ２ is a hydroxy group. [Aspect B6] In intermediate B, G １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G ３ is CR ３ｃ and G ４ is CR ３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group optionally substituted with one or more substituents selected from the group consisting of a halogen atom and a cyano group, a phenyl group optionally substituted with one or more halogen atoms, a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more halogen atoms, or a halogen atom. [Aspect B7] A compound in which, in intermediate B, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a halogen atom. １ , G ２ , G ３ , and G ４ The combination of １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom; G １ is CR３ａ and G ２ is CR ３ｂ and G ３ is a nitrogen atom, and G ４ is CR ３ｄ A combination in which: １ is CR ３ａ and G ２ is a nitrogen atom, and G ３ is CR ３ｃ and G ４ is CR ３ｄ A combination in which: １ is a nitrogen atom, and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ or a combination in which １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect B10] In intermediate B, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is a nitrogen atom or CR ３ｄ and R ３ａ , R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect B11] A compound in which, in intermediate B, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ, R ３ｂ , and R ３ｄ is a hydrogen atom, and R ３ｃ is a halogen atom. [Aspect B12] In intermediate B, G １ is CR ３ａ and G ２ is CR ３ｂ and G ３ is CR ３ｃ and G ４ is CR ３ｄ and R ３ａ , R ３ｃ , and R ３ｄ is a hydrogen atom, and R ３ｂ is a halogen atom. [Aspect B13] A compound in Aspect B2, in which W is an oxygen atom. [Aspect B14] A compound in Aspect B3, in which W is an oxygen atom. [Aspect B15] A compound in Aspect B4, in which W is an oxygen atom. [Aspect B16] A compound in Aspect B5, in which W is an oxygen atom. [Aspect B17] A compound in Aspect B6, in which W is an oxygen atom. [Aspect B18] A compound in Aspect B7, in which W is an oxygen atom. [Aspect B19] A compound in Aspect B8, in which W is an oxygen atom. [Aspect B20] A compound in Aspect B9, in which W is an oxygen atom. [Aspect B21] A compound in Aspect B10, in which W is an oxygen atom. [Aspect B22] A compound in Aspect B11, in which W is an oxygen atom. [Aspect B23] A compound in Aspect B12, in which W is an oxygen atom. [Aspect B24] A compound in Aspect B4, in which R ２ is a C1-C6 alkyl group. [Aspect B25] In Aspect B5, R ２ is a C1-C6 alkyl group. [Aspect B26] In Aspect B6, R ２ is a C1-C6 alkyl group. [Aspect B27] In aspect B7, R ２ is a C1-C6 alkyl group. [Aspect B28] In Aspect B8, R ２ is a C1-C6 alkyl group. [Aspect B29] In Aspect B9, R ２ is a C1-C6 alkyl group. [Aspect B30] In Aspect B10, R ２is a C1-C6 alkyl group. [Aspect B31] In Aspect B11, R ２ is a C1-C6 alkyl group. [Aspect B32] In Aspect B12, R ２ is a C1-C6 alkyl group. [Aspect B33] In Aspect B4, R ２ is an ethyl group. [Aspect B34] In Aspect B5, R ２ is an ethyl group. [Aspect B35] In Aspect B6, R ２ is an ethyl group. [Aspect B36] In aspect B7, R ２ is an ethyl group. [Aspect B37] In Aspect B8, R ２ is an ethyl group. [Aspect B38] In Aspect B9, R ２ is an ethyl group. [Aspect B39] In Aspect B10, R ２ is an ethyl group. [Aspect B40] In aspect B11, R ２ is an ethyl group. [Aspect B41] In aspect B12, the compound ２ is an ethyl group. [Aspect B42] In aspect B4, W is an oxygen atom, and R ２ [Aspect B43] In aspect B5, W is an oxygen atom, and R ２ [Aspect B44] The compound in aspect B6, in which W is an oxygen atom and R ２ [Aspect B45] In aspect B7, W is an oxygen atom, and R ２ is an ethyl group. [Aspect B46] In aspect B8, W is an oxygen atom, and R ２ is an ethyl group. [Aspect B47] In aspect B9, W is an oxygen atom, and R ２ is an ethyl group. [Aspect B48] In aspect B10, W is an oxygen atom, and R ２ [Aspect B49] The compound in aspect B11, in which W is an oxygen atom and R ２ is an ethyl group. [Aspect B50] In aspect B12, W is an oxygen atom, and R ２is an ethyl group. [Aspect B51] A compound according to Aspect B6, wherein X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B52] In aspect B7, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B53] In Aspect B8, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B54] In Aspect B9, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B55] In Aspect B10, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B56] In Aspect B11, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B57] In Aspect B12, X ２ is a chlorine atom, a bromine atom, or an iodine atom. [Aspect B58] In Aspect B6, X ２ is a hydroxy group. [Aspect B59] In aspect B7, X ２ is a hydroxy group. [Aspect B60] In aspect B8, X ２ is a hydroxy group. [Aspect B61] In Aspect B9, X ２ is a hydroxy group. [Aspect B62] In Aspect B10, X ２ is a hydroxy group. [Aspect B63] In Aspect B11, X ２ is a hydroxy group. [Aspect B64] In Aspect B12, X ２ [Aspect B65] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination:１ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ and is a nitrogen atom. [Aspect B66] In any of Aspects B1 to B64 or Intermediate B, B １ , B ２ , and B ３ The combination of １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ A combination: １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ or a combination in which B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ , R ６ｂ , and R ６ｃ are the same or different, and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups; OR ７２ or a hydrogen atom. [Aspect B67] In any of Aspects B1 to B64 or Intermediate B, B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ａ is a hydrogen atom, and R ６ｂ and R ６ｃare the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Aspect B68] In any of Aspects B1 to B64 or Intermediate B, B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｃ is a hydrogen atom. [Aspect B69] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein B １ is a nitrogen atom, B ２ is CR ６ｂ , B ３ is CR ６ｃ and R ６ｂ is a hydrogen atom, and R ６ｃ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Aspect B70] In any of Aspects B1 to B64 or Intermediate B, B １ is CR ６ａ , B ２ is a nitrogen atom, B ３ is CR ６ｃ and R ６ａ and R ６ｃ are the same or different and are C1-C6 chain hydrocarbon groups optionally substituted with one or more halogen atoms, C3-C7 cycloalkyl groups optionally substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups, or OR ７２ [Aspect B71] In any of Aspects B1 to B64 or Intermediate B, B １ is CR ６ａ, B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ [Aspect B72] In any of Aspects B1 to B64 or Intermediate B, B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ 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 substituents selected from the group consisting of a halogen atom and a cyano group, or OR ７２ and R ６ｂ is a hydrogen atom. [Aspect B73] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - combination; A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ A is a combination of ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-NR ５ａ - and A ３ Ga-CR ７ｅ R７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Aspect B74] In any of Aspects B1 to B64 or Intermediate B, A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ [Aspect B75] In any of Aspects B1 to B64 or Intermediate B, A ２ and A ３ The combination of ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ -; or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ and R ７ａ , R ７ｂ , R ７ｃ , R ７ｄ , R ７ｅ , R ７ｆ , R ７ｇ , and R ７ｈare the same or different and are a C1-C6 alkyl group or a hydrogen atom. [Aspect B76] A compound in any of Aspects B1 to B64 or Intermediate B, wherein A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ and R ７ｂ , and R ７ｃ and R ７ｄ may each be taken together with the carbon atom to which they are attached to form a C3-C4 cycloalkyl group, or A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ -* １ (* １ Is A ２ represents the bonding position with R ７ａ and R ７ｂ , R ７ｅ and R ７ｆ , and R ７ｇ and R ７ｈ and each may form a C3-C4 cycloalkyl group together with the carbon atom to which they are attached. [Aspect B77] In any of Aspects B1 to B64 or Intermediate B, B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom. [Aspect B78] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect B79] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect B80] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein B １ is CR ６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or OR ７２ and R ７２ is a C1-C6 alkyl group optionally substituted with a halogen atom, and A ２ Ga-CR ７ａ R ７ｂ - and A ３ Ga-CR ７ｃ R ７ｄ - and R ７ａ , R ７ｂ , R ７ｃ and R ７ｄ is a hydrogen atom. [Aspect B81] A compound in any one of Aspects B1 to B64 or Intermediate B, wherein B １ is CR６ａ , B ２ is CR ６ｂ , B ３ is a nitrogen atom, and R ６ａ is a hydrogen atom, and R ６ｂ is a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, a halogen atom, or OR ７２ and R ７２ is a C1-C6 chain hydrocarbon group optionally substituted with a halogen atom.

[0016] Next, the method for producing the compound of the present invention will be described.

[0017] 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. [In the formula, the symbols have the same meanings as defined above.]

[0018] 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. Examples of the base include 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 typically used in a ratio of 0.01 to 0.5 moles per mole of compound (I-a). In the reaction, the 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 in the range of -20°C to 80°C. The reaction time is typically in the range of 0.1 to 12 hours. After completion of the reaction, water is added to the reaction mixture, followed by extraction 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). Compound (I-b) can be obtained by drying and concentrating the organic layer.

[0019] 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. Examples of bases include 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). Examples of catalysts include 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. Compound (I-c) can be obtained by drying and concentrating the organic layer.

[0020] 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).

[0021] 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. [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 (hereinafter referred to as ethers) such as tetrahydrofuran (hereinafter referred to as THF), methyl tert-butyl ether (hereinafter referred to as MTBE), ethylene glycol dimethyl ether, 1,4-dioxane, and cyclopentyl methyl ether; halogenated hydrocarbons; aromatic hydrocarbons (hereinafter referred to as aromatic hydrocarbons) such as toluene and xylene; nitriles; nitrogen-containing aromatic compounds (hereinafter referred to as nitrogen-containing aromatic compounds) such as pyridine, picoline, lutidine, and quinoline; and mixtures of two or more of these. 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 mole 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 completion of the reaction, compound (IS-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.

[0022] 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. [wherein the symbols have the same meanings as defined above.] Compound (IS-2) can be produced according to Production Method 2, using compound (IO-2) instead of compound (IO-1).

[0023] Production Method 4 Compound (IO-1) can be produced by reacting a compound represented by formula (M-1) (hereinafter referred to as compound (M-1)) with a compound represented by formula (M-2) (hereinafter referred to as compound (M-2)) in the presence of a base. [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 meaning 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 N,N-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 (hereinafter referred to as organic bases) such as triethylamine, N,N-diisopropylethylamine, pyridine, and 4-(dimethylamino)pyridine; alkali metal carbonates (hereinafter referred to as alkali metal carbonates) such as sodium carbonate, potassium carbonate, and cesium carbonate; and alkali metal hydrides (hereinafter referred to as alkali metal hydrides) such as sodium hydride. 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). 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). In the reaction, compound (M-2) is typically used in a ratio of 0.8 to 1.2 moles per mole of compound (M-1), and a base is typically used in a ratio of 1 to 3 moles per mole of compound (M-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) is a commercially available compound or can be produced, for example, according to the method described in International Publication No. 2013 / 192346.

[0024] Production Method 5 Compound (IO-2) can be produced by reacting a compound represented by formula (M-3) (hereinafter referred to as compound (M-3)) with compound (M-2) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] The reaction can be carried out in accordance with Production Method 4, except that compound (M-3) is used in place of compound (M-1). Compound (M-3) is a commercially available compound, or can be produced by a known method.

[0025] Production Method 6 The compound represented by formula (In0-1) (hereinafter referred to as compound (In0-1)) can be produced according to the following scheme. [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.] First, a method for producing a compound represented by formula (M-5) (hereinafter referred to as compound (M-5)) will be described. Compound (M-5) can be produced in accordance with Production Method 4, using a compound represented by formula (M-4) (hereinafter referred to as compound (M-4)) instead of compound (M-2).

[0026] Next, a method for producing a compound represented by formula (M-6) (hereinafter referred to as compound (M-6)) will be described. Compound (M-6) can be produced by reacting compound (M-5) 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). 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-6) can be obtained by adding water to the reaction mixture, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.

[0027] Next, a method for producing compound (I-n0-1) from compound (M-5) will be described. Compound (I-n0-1) can be produced by reacting compound (M-5), 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). 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, 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.

[0028] Next, a method for producing compound (I-n0-1) from compound (M-6) will be described. Compound (I-n0-1) can also be produced by reacting compound (M-6) 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)ferrocene]palladium(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, and organic bases. 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). 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-6). 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.

[0029] Production Method 7 The compound represented by formula (In0-2) (hereinafter referred to as compound (In0-2)) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.] The compound represented by formula (M-7) (hereinafter referred to as compound (M-7)) can be produced according to Production Method 6, using compound (M-3) instead of compound (M-1).

[0030] The compound represented by formula (M-8) (hereinafter referred to as compound (M-8)) can be produced in accordance with the method for producing compound (M-6) from compound (M-5) in Production Method 6, using compound (M-7) instead of compound (M-5).

[0031] Compound (I-n0-2) can be produced in accordance with the method for producing compound (I-n0-1) from compound (M-5) in Production Method 6, using compound (M-7) instead of compound (M-5).

[0032] Compound (I-n0-2) can also be produced using compound (M-8) instead of compound (M-6) according to the method for producing compound (I-n0-1) from compound (M-6) in Production Method 6.

[0033] Production Method 8 Compound (IO-1) can also be produced by reacting a compound represented by formula (M-9-X) (hereinafter referred to as compound (M-9-X)) with a base. [In the formula, X Ａrepresents a chlorine atom, a bromine atom, or an 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; and mixtures of two or more of these. Examples of the base include organic bases; alkali metal carbonates; and alkali metal hydrides. The reaction can also be carried out using a metal catalyst, if necessary. Examples of the metal catalyst 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 usually used in a ratio of 0.01 to 0.5 moles per mole of compound (M-9-X). The reaction can also be carried out using a ligand, if necessary. 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, 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 usually used in a ratio of 0.01 to 0.5 moles per mole of compound (M-9-X). In the reaction, 1 to 5 moles of base are usually used per mole of compound (M-9-X). The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.After the reaction is complete, the compound (IO-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.

[0034] Production Method 9 Compound (IO-1) can also be produced by intramolecular condensation of a compound represented by formula (M-9-OH) (hereinafter referred to as compound (M-9-OH)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent include ethers; halogenated hydrocarbons; aromatic hydrocarbons; esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters); nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of these. The condensing agent used in the reaction includes, for example, a mixture of triphenylphosphine and an azodiester compound. Examples of the azodiester compound include diethyl azodicarboxylate. The condensing agent is usually used in a ratio of 1 to 5 moles per mole of compound (M-9-OH). 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 24 hours. After completion of the reaction, compound (I-O-1) can be obtained by adding water to the reaction mixture, extracting it with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.

[0035] Production Method 10 Compound (IO-1) can also be produced by reacting a compound represented by formula (M-10-X) (hereinafter referred to as compound (M-10-X)) with a base. [wherein the symbols have the same meanings as defined above.] Compound (IO-1) can also be produced according to Production Method 8, except that compound (M-10-X) is used instead of compound (M-9-X).

[0036] Production Method 11 Compound (IO-1) can also be produced by intramolecular condensation of a compound represented by formula (M-10-OH) (hereinafter referred to as compound (M-10-OH)) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (IO-1) can also be produced according to Production Method 9, except that compound (M-10-OH) is used instead of compound (M-9-OH).

[0037] Production Method 12 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. [In the formula, the symbols have the same meanings as defined above.] Compound (I-b-p) can be produced in accordance with Production Method 1, using compound (I-a-p) instead of compound (I-a). Compound (I-c-p) can be produced in accordance with Production Method 1, using compound (I-b-p) instead of compound (I-b). Compound (I-c-p) can also be produced in accordance with Production Method 1, using compound (I-a-p) instead of compound (I-a).

[0038] Production Method 13 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 sulfating agent. [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).

[0039] Production Method 14 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 sulfating agent. [In the formula, the symbols have the same meanings as defined above.] Compound (IS-2p) can be produced according to Production Method 2, except for using compound (IO-2p) instead of compound (IO-1).

[0040] Production Method 15 Compound (IO-1p) can be produced by reacting compound (M-1) with a compound represented by formula (M-11) (hereinafter referred to as compound (M-11)) in the presence of a base. [wherein the symbols have the same meanings as defined above.] Compound (IO-1p) can be produced according to Production Method 4, except that compound (M-11) is used instead of compound (M-2).

[0041] Production Method 16 Compound (IO-2p) can be produced by reacting compound (M-3) with compound (M-11) in the presence of a base. [wherein the symbols have the same meanings as defined above.] Compound (IO-2p) can be produced according to Production Method 5, except that compound (M-11) is used instead of compound (M-2).

[0042] 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. [In the formula, the symbols have the same meanings as defined above.] The compound represented by formula (M-13) (hereinafter referred to as compound (M-13)) can be produced in accordance with Production Method 6, using compound (M-12) instead of compound (M-4). Compound (M-12) is a commercially available compound, or can be produced using a known method.

[0043] The compound represented by formula (M-14) (hereinafter referred to as compound (M-14)) can be produced using compound (M-13) instead of compound (M-5) in accordance with the method for producing compound (M-6) from compound (M-5) in Production Method 6.

[0044] Compound (I-n0-1p) can also be produced using compound (M-13) instead of compound (M-5) according to the method for producing compound (I-n0-1) from compound (M-5) in Production Method 6.

[0045] Compound (I-n0-1p) can also be produced using compound (M-14) instead of compound (M-6) according to the method for producing compound (I-n0-1) from compound (M-6) in Production Method 6.

[0046] 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. [In the formula, the symbols have the same meanings as defined above.] The compound represented by formula (M-15) (hereinafter referred to as compound (M-15)) can be produced according to Production Method 7, using compound (M-12) instead of compound (M-4).

[0047] The compound represented by formula (M-16) (hereinafter referred to as compound (M-16)) can be produced using compound (M-15) instead of compound (M-7) in accordance with the method for producing compound (M-8) from compound (M-7) in Production Method 7.

[0048] Compound (I-n0-2p) can also be produced using compound (M-15) instead of compound (M-7) according to the method for producing compound (I-n0-2) from compound (M-7) in Production Method 7.

[0049] Compound (I-n0-2p) can also be produced using compound (M-16) instead of compound (M-8) according to the method for producing compound (I-n0-2) from compound (M-8) in Production Method 7.

[0050] Production Method 19 Compound (IO-1p) can also be produced by reacting a compound represented by formula (M-17-X) (hereinafter referred to as compound (M-17-X)) with a base. [wherein the symbols have the same meanings as defined above.] Compound (IO-1p) can be produced according to Production Method 8, except that compound (M-17-X) is used instead of compound (M-9-X).

[0051] Production Method 20 Compound (IO-1p) can also be produced by intramolecular condensation of a compound represented by formula (M-17-OH) (hereinafter referred to as compound (M-17-OH)) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (IO-1p) can be produced according to Production Method 9, except for using compound (M-17-OH) instead of compound (M-9-OH).

[0052] Production Method 21 Compound (IO-1p) can also be produced by reacting a compound represented by formula (M-18-X) (hereinafter referred to as compound (M-18-X)) with a base. [wherein the symbols have the same meanings as defined above.] Compound (IO-1p) can be produced according to Production Method 10, except that compound (M-18-X) is used instead of compound (M-10-X).

[0053] Production Method 22 Compound (IO-1p) can also be produced by intramolecular condensation of a compound represented by formula (M-18-OH) (hereinafter referred to as compound (M-18-OH)) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (IO-1p) can also be produced according to Production Method 11, except that compound (M-18-OH) is used instead of compound (M-10-OH).

[0054] The N-oxide of the compound of formula (I) 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.

[0055] Production Method 24 A compound represented by formula (I-O-1ph) (hereinafter referred to as compound (I-O-1ph)) can be produced by reacting a compound represented by formula (I-O-1pp) (hereinafter referred to as compound (I-O-1pp)) with a compound represented by formula (Ph-BOH) (hereinafter referred to as compound (Ph-BOH)) or a compound represented by formula (Ph-Bpin) (hereinafter referred to as compound (Ph-Bpin)) in the presence of a metal catalyst and a base. [In the formula, R ４ｐ represents a chlorine atom, a bromine atom, or an iodine atom; R ４ｈ is the group H ２where y represents 0, 1, 2, 3, 4, or 5, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of these. Examples of bases used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrides; and alkali metal phosphates such as potassium phosphate (hereinafter referred to as alkali metal phosphates). Examples of metal catalysts used in the reaction include nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II). The reaction can also be carried out using a ligand, if necessary. 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, 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 (I-O-1pp). In the reaction, compound (Ph-BOH) or compound (Ph-Bpin) is usually used in a ratio of 1 to 5 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 1 to 5 moles, relative to 1 mole of compound (I-O-1pp). The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.5 to 24 hours.After the reaction is complete, the compound (IO-1ph) 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.

[0056] Production Method 25 The compound represented by formula (I-O-2ph) (hereinafter referred to as compound (I-O-2ph)) can be produced by reacting a compound represented by formula (I-O-2pp) (hereinafter referred to as compound (I-O-2pp)) with compound (Ph-BOH) or compound (Ph-Bpin) in the presence of a metal catalyst and a base. [In the formula, the symbols have the same meanings as defined above.] Compound (IO-2ph) can be produced according to Production Method 24, except for using compound (IO-2pp) instead of compound (IO-1pp).

[0057] Production Method 26 The compound represented by formula (IO-1Ar) (hereinafter referred to as compound (IO-1Ar)) can be produced according to the following scheme. [In the formula, A １ａ is CR １ａ or a nitrogen atom, R １ａ is a hydrogen atom or a group H ２ represents a substituent selected from the following: ｈrepresents a halogen atom, and the other symbols have the same meanings as above.] First, a method for producing a compound represented by formula (I-O-1-Bpin) (hereinafter referred to as compound (I-O-1-Bpin)) from a compound represented by formula (I-O-1pa) (hereinafter referred to as compound (I-O-1pa)) will be described. Compound (I-O-1-Bpin) can be produced by reacting compound (I-O-1pa) with bis(pinacolato)diboron 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 ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates. Examples of metal catalysts used in the reaction include palladium catalysts such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II). For the reaction, Bis(pinacolato)diboron is typically used in a ratio of 1 to 3 moles, the metal catalyst is typically used in a ratio of 0.01 to 0.5 moles, and the base is typically used in a ratio of 1 to 5 moles, relative to 1 mole of compound (I-O-1pa). 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 (I-O-1-Bpin) 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.

[0058] Next, a method for producing compound (I-O-1Ar) from compound (I-O-1-Bpin) will be described. Compound (I-O-1Ar) can be produced by reacting compound (I-O-1-Bpin) with a compound represented by formula (Ar-hal) (hereinafter referred to as compound (Ar-hal)) 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 ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of these. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates. Examples of the metal catalyst used in the reaction include palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), etc. The reaction can also be carried out using a ligand, if necessary. 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, 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 (I-O-1-Bpin). In the reaction, the compound (Ar-hal) is usually used in a ratio of 1 to 5 moles, the metal catalyst is usually used in a ratio of 0.01 to 0.5 moles, and the base is usually used in a ratio of 1 to 5 moles, relative to 1 mole of the compound (IO-1-Bpin). The reaction temperature is usually in the range of -20°C to 150°C.The reaction time is usually in the range of 0.5 to 24 hours. After completion of the reaction, compound (IO-1Ar) 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.

[0059] Production Method 27 The compound represented by formula (IO-2Ar) (hereinafter referred to as compound (IO-2Ar)) can be produced according to the following scheme. [In the formula, the symbols have the same meanings as defined above.] Compound (I-O-2Ar) can be produced from compound (I-O-2-Bpin) produced according to Production Method 26, using compound (I-O-2pa) instead of compound (I-O-1pa), in a similar manner to Production Method 26.

[0060] Production Method 28 The compound represented by formula (IO-1NBoc) (hereinafter referred to as compound (IO-1NBoc)) can be produced by reacting compound (IO-1pp) with tert-butyl carbamate in the presence of a metal catalyst and a base. [In the formula, the symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of bases used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrides, and alkali metal phosphates. Examples of metal catalysts used in the reaction include nickel catalysts such as bis(cyclooctadiene)nickel(0) and nickel(II) chloride; and palladium catalysts such as palladium(II) acetate, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II). The reaction can also be carried out using a ligand, if necessary. 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, 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 (I-O-1pp). In the reaction, tert-butyl carbamate is typically used in a ratio of 1 to 5 moles, a metal catalyst typically in a ratio of 0.01 to 0.5 moles, and a base typically in a ratio of 1 to 5 moles, relative to 1 mole of compound (I-O-1pp). 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 (I-O-1NBoc) 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.

[0061] Production Method 29 The compound represented by the formula (I-O-2NBoc) (hereinafter referred to as compound (I-O-2NBoc)) can be produced by reacting compound (I-O-2pp) with tert-butyl carbamate in the presence of a metal catalyst and a base. [In the formula, the symbols have the same meanings as defined above.] Compound (IO-2NBoc) can be produced according to Production Method 28, except for using compound (IO-2pp) instead of compound (IO-1pp).

[0062] Production method 30 Formula (I-O-1NH ２ ) (hereinafter referred to as compound (I-O-1NH ２ ) can be produced by reacting the compound (IO-1NBoc) with an acid. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, ethers, alcohols, water, and mixtures of two or more of these. Examples of the acid used in the reaction include mineral acids such as hydrochloric acid and carboxylic acids such as trifluoroacetic acid. The acid is usually used in a ratio of 1 to 50 moles per mole of compound (I-O-1NBoc). The reaction temperature is usually in the range of 0°C to 120°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is extracted with an organic solvent, and post-treatments such as drying and concentrating the organic layer can be carried out to obtain compound (I-O-1NH ２ ) can be obtained.

[0063] Production method 31 Formula (I-O-2NH ２ ) (hereinafter referred to as compound (I-O-2NH ２ ) can be produced by reacting the compound (IO-2NBoc) with an acid. [wherein the symbols have the same meanings as defined above] Compound (IO-2NH ２ ) can be produced according to Production Method 30, except that compound (IO-2NBoc) is used in place of compound (IO-1NBoc).

[0064] Production Method 32 A compound represented by the formula (IO-1-NHamide) (hereinafter referred to as compound (IO-1-NHamide)) can be produced by the reaction of compound (IO-1NH ２ ) with a compound represented by formula (R-13) (hereinafter referred to as compound (R-13)). [In the formula, R Ａｌｋｙｌ 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 D ２ a phenyl group optionally substituted with one or more substituents selected from the group D ２ and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers; aliphatic hydrocarbons such as hexane, heptane, and octane (hereinafter referred to as aliphatic hydrocarbons); aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents; nitrogen-containing aromatic compounds; and mixtures of two or more of these. A base can be used in the reaction as needed. Examples of the base used in the reaction include alkali metal carbonates; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); and organic bases. When a base is used in the reaction, the compound (I-O-1NH ２ The base is usually used in a ratio of 1 to 2 moles per mole of the compound (IO-1NH ２Compound (R-13) is usually used in a ratio of 0.8 to 2 moles per mole of (I-O-1-NHamide). 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 24 hours. After completion of the reaction, water is added to the reaction mixture, followed by extraction with an organic solvent, and post-treatment such as drying and concentrating the organic layer can be carried out to obtain compound (I-O-1-NHamide). Compound (R-13) is a commercially available compound or can be produced using known methods.

[0065] Production Method 33 A compound represented by the formula (I-O-2-NHamide) (hereinafter referred to as compound (I-O-2-NHamide)) can be produced by the reaction of compound (I-O-2NH ２ ) with compound (R-13). [wherein the symbols have the same meanings as defined above] Compound (I-O-2-NHamide) can be prepared by the reaction of compound (I-O-1NH ２ ) instead of the compound (IO-2NH ２ ) and can be produced in accordance with Production Method 32.

[0066] Production Method 34 A compound represented by formula (I-O-1-amide) (hereinafter referred to as compound (I-O-1-amide)) can be produced by reacting compound (I-O-1-NHamide) with compound (R-14) in the presence of a base. [In the formula, L ２ represents a leaving group such as a chlorine atom, a bromine atom, or an iodine atom, and R ａｍｉｄｅrepresents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atoms, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. In the reaction, compound (R-14) is usually used in a ratio of 1 to 5 moles and a base is usually used in a ratio of 1 to 5 moles per mole of compound (I-O-1-NHamide). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (I-O-1-amide) 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. The compound (R-14) is a commercially available compound or can be prepared using known methods.

[0067] Production Method 35 The compound represented by the formula (I-O-2-amide) (hereinafter referred to as compound (I-O-2-amide)) can be produced by reacting compound (I-O-2-NHamide) with compound (R-14) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] Compound (I-O-2-amide) can be produced according to Production Method 34, using compound (I-O-2-NHamide) instead of compound (I-O-1-NHamide).

[0068] Production Method 36 The compound represented by the formula (I-O-1-OH) (hereinafter referred to as compound (I-O-1-OH)) can be produced by reacting compound (I-O-1-OBn) with hydrogen in the presence of a catalyst. [In the formula, the symbols have the same meanings as above.] Hydrogen gas is used in the reaction. The pressure of the hydrogen gas is usually 1 to 100 atmospheres. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, esters, alcohols, water, and mixtures of two or more of these. Examples of catalysts used in the reaction include transition metal compounds such as palladium carbon, palladium (II) hydroxide, Raney nickel, and platinum oxide. The catalyst is usually used in a ratio of 0.001 to 0.5 moles per mole of compound (I-O-1-OBn). The reaction can also be carried out using an acid, a base, or the like, as necessary. Examples of acids include acetic acid and hydrochloric acid, and examples of bases include tertiary amines such as triethylamine. When an acid is used in the reaction, the acid is usually used in a ratio of 0.001 to 0.5 moles per mole of compound (I-O-1-OBn). When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (I-O-1-OBn). The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction mixture is filtered, and if necessary, extracted with an organic solvent, and the organic layer is dried, concentrated, and other post-treatment procedures are carried out to obtain compound (I-O-1-OH).

[0069] Production Method 37 The compound represented by the formula (I-O-2-OH) (hereinafter referred to as compound (I-O-2-OH)) can be produced by reacting compound (I-O-2-OBn) with hydrogen in the presence of a catalyst. [In the formula, the symbols have the same meanings as defined above.] Compound (IO-2-OH) can be produced according to Production Method 36, except that compound (IO-2-OBn) is used in place of compound (IO-1-OBn).

[0070] Production Method 38 A compound represented by the formula (I-O-1-OAlkyl) (hereinafter referred to as compound (I-O-1-OAlkyl)) can be produced by reacting compound (I-O-1-OH) with a compound represented by the formula (R-15) (hereinafter referred to as compound (R-15)) in the presence of a base. [In the formula, L ３ represents a leaving group such as a chlorine atom, a bromine atom, or an iodine atom, and R ＯＨ is the group F 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 D ２ a phenyl group optionally substituted with one or more substituents selected from the group D ２ The other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. The reaction is usually carried out in a ratio of 1 to 5 moles of compound (R-15) and 1 to 5 moles of base per mole of compound (I-O-1-OH). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (I-O-1-OAlkyl) 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-15) is a commercially available compound or can be produced using known methods.

[0071] Production Method 39 The compound represented by the formula (I-O-2-OAlkyl) (hereinafter referred to as compound (I-O-2-OAlkyl)) can be produced by reacting compound (I-O-2-OH) with compound (R-15) in the presence of a base. [wherein the symbols have the same meanings as defined above.] Compound (I-O-2-OAlkyl) can be produced according to Production Method 38, except that compound (I-O-2-OH) is used in place of compound (I-O-1-OH).

[0072] The methods for producing intermediates are described below.

[0073] Reference Production Method 1 The compound represented by formula (M-2-n1) and the compound represented by formula (M-2-n2) can be produced by reacting the compound represented by formula (M-2-n0) with an oxidizing agent. [wherein the symbols have the same meanings as defined above.] These reactions can be carried out in accordance with Production Method 1.

[0074] 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. [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 meaning as above.] A 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. In the reaction, compound (M-19) is usually used in a ratio of 1 to 10 moles 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. The compound (R-6) and the compound (M-19) are commercially available compounds or can be prepared by known methods.

[0075] 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 of two or more of these. 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.

[0076] 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 in accordance with the method for producing compound (M-6) from compound (M-5) in Production Method 6.

[0077] 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) or compound (M-6) in Production Method 6.

[0078] Reference Production Method 3 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. [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.

[0079] Reference Production Method 4 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.

[0080] Reference Production Method 5 Compound (M-9-X) can be produced by reacting a compound represented by formula (M-23) (hereinafter referred to as compound (M-23)) with a compound represented by formula (M-24) (hereinafter referred to as compound (M-24)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, halogenated hydrocarbons, aromatic hydrocarbons, esters, nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures of two or more of these. Examples of condensing agents used in the reaction include carbodiimide compounds such as 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide. A catalyst can be used in the reaction, if necessary. Examples of catalysts used in the reaction include 1-hydroxybenzotriazole. 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 (M-24). When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles per mole of compound (M-24). In the reaction, compound (M-23) is usually used in a ratio of 1 to 2 moles, and a condensing agent is usually used in a ratio of 1 to 2 moles, per mole of compound (M-24). 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 12 hours. After completion of the reaction, compound (M-9-X) 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.

[0081] Reference Production Method 6 Compound (M-23) can be produced by hydrolyzing a compound represented by formula (M-25) (hereinafter referred to as compound (M-25)). [In the formula, R Ａ represents a C1-C3 alkyl group such as a methyl group or an ethyl group, and other symbols have the same meanings as above.] When hydrolyzing with an acid, the reaction is usually carried out using an aqueous acid solution as a solvent. Examples of the acid used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid. The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M-23) can be obtained by post-treatment such as extraction with an organic solvent, drying and concentrating the organic layer.

[0082] When hydrolysis is carried out with a base, the reaction is usually carried out in the presence of a solvent. Examples of solvents used in the reaction include ethers, alcohols, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydroxides. In the reaction, 1 to 10 moles of base are usually used per mole of compound (M-25). The reaction temperature is usually in the range of 0°C to 120°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction solution is acidified, and the reaction mixture is extracted with an organic solvent. The organic layer is then dried and concentrated, and other post-treatment procedures can be carried out to obtain compound (M-23).

[0083] Reference Production Method 7 Compound (M-25) can be produced by reacting a compound represented by formula (M-26) (hereinafter referred to as compound (M-26)) with a compound represented by formula (R-8) (hereinafter referred to as compound (R-8)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents include ethers, halogenated hydrocarbons, aromatic hydrocarbons, esters, nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures of two or more of these. Examples of condensing agents used in the reaction include mixtures of triphenylphosphine and an azodiester compound. Examples of azodiester compounds include diethyl azodicarboxylate. In the reaction, compound (R-8) is usually used in a ratio of 1 to 5 moles and the condensing agent is usually used in a ratio of 1 to 5 moles per mole of compound (M-26). 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 24 hours. After completion of the reaction, compound (M-25) can be obtained by post-treatment, such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. Compound (M-26) is a commercially available compound or can be produced using known methods. Compound (R-8) is a commercially available compound or can be prepared using known methods.

[0084] Reference Production Method 8 Compound (M-24) can be produced by reacting compound (M-2-h) with ammonia. [In the formula, X ｅrepresents a fluorine atom or a chlorine atom, and other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, nitriles, aprotic polar solvents, alcohols, water, and mixtures of two or more of these. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases and alkali metal carbonates. When a base is used in the reaction, the base is usually used in a ratio of 0.1 to 5 moles per mole of compound (M-2-h). Ammonia can also be used in the form of a solution such as aqueous ammonia or ammonia methanol solution. The reaction is usually used in a ratio of 1 to 100 moles per mole of compound (M-2-h). The reaction temperature is usually in the range of -20°C to 100°C. The reaction time is usually in the range of 0.1 to 48 hours. After completion of the reaction, compound (M-24) 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.

[0085] Reference Production Method 9 Compound (M-9-X) can also be produced by reacting a compound represented by formula (M-27) (hereinafter referred to as compound (M-27)) with compound (M-24). [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers; aliphatic hydrocarbons; aromatic hydrocarbons; halogenated hydrocarbons; esters; nitriles; aprotic polar solvents, and mixtures of two or more of these. A base can be used in the reaction, if necessary. Examples of bases used in the reaction include alkali metal carbonates; alkali metal hydroxides; and organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles per mole of compound (M-24). In the reaction, compound (M-27) is usually used in a ratio of 0.8 to 1.2 moles per mole of compound (M-24). 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 24 hours. After completion of the reaction, compound (M-9-X) 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.

[0086] Reference Production Method 10 Compound (M-27) can be produced by reacting compound (M-23) in the presence of a chlorinating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, halogenated hydrocarbons, and mixtures of two or more of these. Examples of the chlorinating agent used in the reaction include thionyl chloride, oxalyl dichloride, phosphorus oxychloride, etc. In the reaction, the chlorinating agent is usually used in a ratio of 1 to 5 moles per mole of compound (M-23). ​​The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M-27) can be obtained by distilling off the solvent.

[0087] Reference Production Method 11 Compound (M-9-OH) can be produced by reacting a compound represented by formula (M-9-P) (hereinafter referred to as compound (M-9-P)) with an acid. [In the formula, X Ｂ is OR Ｂ represents RＢ represents a protecting group such as a tetrahydropyranyl group, a methoxymethyl group, a 2-methoxyethoxymethyl group, a tert-butyldimethylsilyl group, or a tribenzylsilyl group, and other symbols have the same meaning as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, water, and mixtures of two or more of these. Examples of acids used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid. The reaction temperature is usually in the range of 0°C to 120°C. The reaction time is usually in the range of 0.1 to 24 hours. In the reaction, the acid is usually used in a ratio of 1 to 10 moles per mole of compound (M-9-P). After completion of the reaction, the reaction mixture is extracted with an organic solvent, and compound (M-9-OH) can be obtained by post-treatment such as drying and concentrating the organic layer.

[0088] Reference Production Method 12 Compound (M-9-P) can be produced by reacting a compound represented by formula (M-28) (hereinafter referred to as compound (M-28)) with compound (M-24) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (M-9-P) can be produced according to Reference Production Method 5, using compound (M-28) instead of compound (M-23).

[0089] Reference Production Method 13 Compound (M-28) can be produced by hydrolyzing a compound represented by formula (M-29) (hereinafter referred to as compound (M-29)) in the presence of a base. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydroxides. In the reaction, the base is usually used in a ratio of 1 to 10 moles per mole of compound (M-29). The reaction temperature is usually in the range of 0°C to 120°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, the reaction solution is acidified, and then the reaction mixture is extracted with an organic solvent. The organic layer is dried and concentrated, and other post-treatment procedures can be carried out to obtain compound (M-28).

[0090] Reference Production Method 14 Compound (M-29) can be produced by reacting compound (M-26) with a compound represented by formula (R-9) (hereinafter referred to as compound (R-9)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as defined above.] Compound (M-29) can be produced in accordance with Reference Production Method 7, using compound (R-9) instead of compound (R-8). Compound (R-9) is a commercially available compound, or can be produced using a known method.

[0091] Reference Production Method 15 The compound (M-10-X) can be produced by reacting the compound (M-10-OH) in the presence of a halogenating agent. [In the formula, the symbols have the same meanings as defined above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, alcohols, aromatic hydrocarbons, halogenated hydrocarbons, aprotic polar solvents, water, and mixtures of two or more of these. Examples of halogenating agents used in the reaction include hydrogen halides such as hydrogen chloride; phosphorus halides such as phosphorus tribromide; thionyl halides such as thionyl chloride; mixtures of triphenylphosphine and carbon tetrachloride; and mixtures of triphenylphosphine and carbon tetrabromide. In the reaction, the halogenating agent is usually used in a ratio of 1 to 10 moles per mole of compound (M-10-OH). A base can be used in the reaction, if necessary. Examples of bases used in the reaction include organic bases. When a base is used in the reaction, the base is usually used in a ratio of 1 to 2 moles per mole of compound (M-10-OH). The reaction temperature is usually in the range of -20°C to 150°C. The reaction time is usually in the range of 0.1 to 24 hours. After the reaction is complete, the compound (M-10-X) 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.

[0092] Reference Production Method 16 Compound (M-10-OH) can be produced by reacting a compound represented by formula (M-10-P) (hereinafter referred to as compound (M-10-P)) with an acid. [wherein the symbols have the same meanings as defined above.] Compound (M-10-OH) can be produced according to Reference Production Method 11, using compound (M-10-P) instead of compound (M-9-P).

[0093] Reference Production Method 17 Compound (M-10-P) can be produced by reacting a compound represented by formula (M-30) (hereinafter referred to as compound (M-30)) with a compound represented by formula (M-33) (hereinafter referred to as compound (M-33)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as defined above.] Compound (M-10-P) can be produced in accordance with Reference Production Method 5, using compound (M-30) instead of compound (M-23) and compound (M-33) instead of compound (M-24). Compound (M-30) is a commercially available compound, or can be produced using a known method.

[0094] Reference Production Method 18 Compound (M-10-P) can also be produced by reacting a compound represented by formula (M-32) (hereinafter referred to as compound (M-32)) with compound (M-33). [In the formula, the symbols have the same meanings as defined above.] Compound (M-10-P) can be produced in accordance with Reference Production Method 9, using compound (M-32) instead of compound (M-27) and compound (M-33) instead of compound (M-24). Compound (M-32) is a commercially available compound, or can be produced using a known method.

[0095] Reference Production Method 19 Compound (M-33) can be produced by reacting compound (M-24) with a compound represented by formula (R-12) (hereinafter referred to as compound (R-12)) in the presence of a base. [In the formula, L represents a leaving group such as a chlorine atom or a bromine atom, and the other symbols have the same meanings as above.] The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal hydrides, alkali metal carbonates, and organic bases. In the reaction, compound (R-12) is usually used in a ratio of 1 to 5 moles and a base is usually used in a ratio of 1 to 2 moles per mole of compound (M-24). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M-33) 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-12) is a commercially available compound or can be produced using known methods.

[0096] Reference Production Method 20 Compound (M-2-n0) can be produced according to the following scheme. [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.] First, the process 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 thereof. 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 completion of the reaction, 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.

[0097] Next, the process 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)ferrocene]palladium(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, and organic bases. 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-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-treatment operations such as drying and concentrating the organic layer.

[0098] Next, the process 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, potassium iodide, etc. 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, DMSO, etc. 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 usually used in a ratio of 0.5 to 10 moles and the halogenating agent is usually used in a ratio of 0.05 to 10 moles per mole of compound (M-4). The reaction temperature is usually in the range of 0°C to 200°C. The reaction time is usually in the range of 0.1 to 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 by a known method. Compound (M-4) is known or can be produced in accordance with the methods described in WO 2015 / 157093, WO 2016 / 109706, Organic & Biomolecular Chemistry, 2017, 15, 4199., and European Journal of Medicinal Chemistry, 2016, 123, 916.

[0099] Reference Production Method 21 A compound represented by formula (M-11-n1) (hereinafter referred to as compound (M-11-n1)) or a compound represented by formula (M-11-n2) (hereinafter referred to as compound (M-11-n2)) can be produced by reacting compound (M-11-n0) with an oxidizing agent. Compound (M-11-n2) can also be produced by reacting compound (M-11-n1) with an oxidizing agent. [wherein the symbols have the same meanings as defined above.] These reactions can be carried out in accordance with Production Method 1.

[0100] Reference Production Method 22 Compound (M-17-X) can be produced by reacting compound (M-23) with a compound represented by formula (M-34) (hereinafter referred to as compound (M-34)) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (M-17-X) can be produced according to Reference Production Method 5, using compound (M-34) instead of compound (M-24).

[0101] Reference Production Method 23 The compound (M-17-X) can also be produced by reacting the compound (M-27) with the compound (M-34). [wherein the symbols have the same meanings as defined above.] Compound (M-17-X) can be produced according to Reference Production Method 9, using compound (M-34) instead of compound (M-24).

[0102] Reference Production Method 24 Compound (M-34) can be produced by reacting a compound represented by formula (M-11-h) (hereinafter referred to as compound (M-11-h)) with ammonia. [wherein the symbols have the same meanings as defined above.] Compound (M-34) can be produced according to Reference Production Method 8, using compound (M-11-h) instead of compound (M-2-h).

[0103] Reference Production Method 25 The compound (M-11-n0) can be produced according to the following scheme. [wherein the symbols have the same meanings as defined above.] These reactions can be carried out according to Reference Production Method 20.

[0104] Reference Production Method 26 Compound (M-17-OH) can be produced by reacting a compound represented by formula (M-17-P) (hereinafter referred to as compound (M-17-P)) with an acid. [wherein the symbols have the same meanings as defined above.] Compound (M-17-OH) can be produced according to Reference Production Method 11, using compound (M-17-P) instead of compound (M-9-P).

[0105] Reference Production Method 27 Compound (M-17-P) can be produced by reacting a compound represented by formula (M-28) (hereinafter referred to as compound (M-28)) with compound (M-34) in the presence of a condensing agent. [wherein the symbols have the same meanings as defined above.] Compound (M-17-P) can be produced according to Reference Production Method 12, using compound (M-34) instead of compound (M-24).

[0106] Reference Production Method 28 Compound (M-18-OH) can be produced by reacting a compound represented by formula (M-18-P) (hereinafter referred to as compound (M-18-P)) with an acid. [wherein the symbols have the same meanings as defined above.] Compound (M-18-OH) can be produced according to Reference Production Method 11, using compound (M-18-P) instead of compound (M-9-P).

[0107] Reference Production Method 29 Compound (M-18-P) can be produced by reacting compound (M-30) with a compound represented by formula (M-35) (hereinafter referred to as compound (M-35)) in the presence of a condensing agent. [In the formula, the symbols have the same meanings as defined above.] Compound (M-18-P) can be produced according to Reference Production Method 5, using compound (M-30) instead of compound (M-23) and compound (M-35) instead of compound (M-24).

[0108] Reference Production Method 30 The compound (M-18-P) can also be produced by reacting the compound (M-32) with the compound (M-35). [wherein the symbols have the same meanings as defined above.] Compound (M-18-P) can be produced according to Reference Production Method 9, using compound (M-32) instead of compound (M-27) and compound (M-35) instead of compound (M-24).

[0109] Reference Production Method 31 Compound (M-35) can be produced by reacting compound (M-34) with compound (R-12) in the presence of a base. [wherein the symbols have the same meanings as defined above.] Compound (M-35) can be produced according to Reference Production Method 19, using compound (M-34) instead of compound (M-24).

[0110] Reference Production Method 32 The compound (M-18-X) can be produced by reacting the compound (M-18-OH) in the presence of a halogenating agent. [wherein the symbols have the same meanings as defined above.] Compound (M-18-X) can be produced according to Reference Production Method 15, using compound (M-18-OH) instead of compound (M-10-OH).

[0111] Compound (M-2) can also be produced, for example, according to the method described in WO 2020 / 158889.

[0112] Reference Production Method 33 Compound (M-1) can also be produced according to the following scheme. [In the formula, X Ｐrepresents a protecting group such as a tert-butoxycarbonyl group, and other symbols have the same meanings as above.] First, a method for producing a compound represented by formula (M-29-N) (hereinafter referred to as compound (M-29-N)) from a compound represented by formula (M-29-N-PG) (hereinafter referred to as compound (M-29-N-PG)) will be described. Compound (M-29-N) can be produced by reacting compound (M-29-N-PG) with an acid. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. Examples of acids used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid; and carboxylic acids such as acetic acid and trifluoroacetic acid. In the reaction, the acid is usually used in a ratio of 1 to 30 moles per mole of compound (M-29-N-PG). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M-29-N) can be obtained by carrying out a post-treatment operation such as concentrating the reaction mixture.

[0113] Next, a method for producing compound (M-1) from compound (M-29-N) will be described. Compound (M-1) can be produced by reacting compound (M-29-N) with a base. The reaction is usually carried out in a solvent. Examples of solvents used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, water, and mixtures of two or more of these. Examples of bases used in the reaction include alkali metal carbonates. The reaction is usually carried out in a ratio of 1 to 30 moles of base per mole of compound (M-29-N). The reaction temperature is usually in the range of 0°C to 100°C. The reaction time is usually in the range of 0.1 to 24 hours. After completion of the reaction, compound (M-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.

[0114] 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.

[0115] 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.

[0116] Group (b) consists of nucleic acid synthesis inhibitors (e.g., phenylamide fungicides, acylamino acid fungicides), cell division and cytoskeleton inhibitors (e.g., MBC fungicides), respiratory inhibitors (e.g., QoI fungicides, QiI fungicides), amino acid synthesis and protein synthesis inhibitors (e.g., anilinopyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (e.g., DMI fungicides such as triazoles), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multisite contact-active fungicides, microbial fungicides, and other fungicidal active ingredients. These are listed in the FRAC classification based on the mechanism of action.

[0117] Group (c) is a group of plant growth regulators (including mycorrhizal fungi and rhizobia).

[0118] Group (d) is a group of repellent ingredients.

[0119] Examples of combinations of the present ingredient 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 SX1840. The present ingredients described below are all known ingredients and can be obtained from commercially available preparations or produced by known methods. When the present ingredient is a microorganism, it can also be obtained from a bacterial depository. The number in parentheses indicates the CAS RN (registered trademark).

[0120] 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, benzoximate + SX, benzpyrimoxan + SX, beta-cyfluthrin + SX, beta-cypermethrin + SX, bifenazate + SX, bifenthrin + SX, bioallethrin + SX,Bioresmethrin + SX, bistrifluron + 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 A) + SX, coumaphos + SX, cryolite + SX, cyanophos + SX, cyantraniliprole + SX,Cyclaniliprole + SX, cyclobutrifluram + SX, cycloprothrin + SX, cycloxaprid + SX, cyenopyrafen + SX, cyetpyrafen + SX, cyflumetofen + SX, cyfluthrin + SX, cyhalodiamide + SX, cyhalothrin + SX, cyhexatin + SX, cypermethrin + SX, cyphenothrin + SX, 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, ethifencarb + 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, Viscum album extract + 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, 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 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 + 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, 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, 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, BT crop protein Cry1Ab (BT crop protein Cry1Ab) + SX, BT crop protein Cry1Ac (BT crop protein Cry1Ac) + SX, BT crop protein Cry1Fa (BT crop protein Cry1Fa) + SX, BT crop protein Cry1A.105 (BT crop protein Cry1A.105) + SX, BT crop protein Cry2Ab (BT crop protein Cry2Ab) + SX,BT crop protein Vip3A + SX, BT crop protein mCry3A + SX, BT crop protein Cry3Ab + SX, BT crop protein Cry3Bb + SX, BT crop protein Cry34Ab1 / Cry35Ab1 + SX, Adoxophyes orana granulovirus 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 nucleopolyhedrosis virus (NPV) + SX, Neodiprion abietis nucleopolyhedrosis virus (NPV) + SX, Neodiprion lecontei nucleopolyhedrosis virus (NPV) + SX, Neodiprion sertifer nucleopolyhedrosis virus (NPV) + SX, Nosema locustae + SX, Orgyia pseudotsugata nucleopolyhedrosis virus (NPV) + SX, Pieris rapae granulosis virus (GV) + SX, Plodia interpunctella granulosis virus (GV) + SX, Spodoptera exigua MNPV + SX, Spodoptera littoralis MNPV + SX, Spodoptera littoralis 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, Dectylaria 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。,

[0121] 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, fenfuram + SX, fenhexamid + 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-aluminium + SX, fuberidazole + SX, furalaxyl + SX, furametpyr + 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, 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 Chenopodium quinoa + SX, seboctylamine + SX, sedaxane + SX, silthiofam + SX,Simeconazole + SX, sodium hydrogencarbonate + SX, spiroxamine + SX, streptomycin + SX, sulfur + SX, tebuconazole + SX, tebufloquin + SX, teclofthalam + SX, tecnazene + SX, terbinafine + SX, tetraconazole + SX, thiabendazole + SX, thifluzamide + SX, thiophanate + SX, thiophanate-methyl + SX, thiram + SX, Thymol + SX, tiadinil + SX, tolclofos-methyl + SX, tolfenpyrad + SX, tolprocarb + SX, tolylfluanid + SX, triadimefon + SX, triadimenol + SX, triazoxide + SX, triclopyricarb + SX, tricyclazole + SX, tridemorph + SX, trifloxystrobin + SX, triflumizole + SX, triforine + SX, triticonazole + SX, Validamycin + SX, valifenalate + SX, vinclozolin + SX,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, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9) + SX, N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)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]pyrimi din-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(Trademark) 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。,

[0122] 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. ,

[0123] Combinations of the present component of the above group (d) with the compound of the present invention: anthraquinone + SX, deet + SX, icaridin + SX.

[0124] 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.

[0125] The compound of the present invention can control 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.

[0126] 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);

[0127] 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.

[0128] 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.

[0129] 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);

[0130] 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).

[0131] 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).

[0132] 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.

[0133] 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.

[0134] 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).

[0135] 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.

[0136] Thysanura: Family Lepismatidae, including the Japanese silverfish (Ctenolepisma villosa) and the European silverfish (Lepisma saccharina).

[0137] 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.

[0138] 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).

[0139] 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.

[0140] The harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes may be harmful insects, harmful arthropods such as harmful mites, harmful mollusks, and harmful nematodes that have reduced sensitivity to insecticides, acaricides, molluscicides, or nematocides, or that have developed resistance to the insecticides, acaricides, molluscicides, or nematocides.

[0141] 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.

[0142] The compound of the present invention or Composition A is typically formulated into aqueous suspensions, oil suspensions, oil solutions, emulsifiable concentrates, emulsions, microemulsions, microcapsule formulations, wettable powders, water dispersible granules, dusts, granules, tablets, aerosols, resin formulations, etc. by mixing an inert carrier such as a solid carrier, liquid carrier, or gaseous carrier with a surfactant, and optionally adding formulation adjuvants such as binders, dispersants, and stabilizers. In addition to these formulations, the compound of the present invention or Composition A can also be formulated into dosage forms described in the Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers-271 to 276, prepared by the FAO / WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517. These formulations typically contain 0.0001 to 99% by weight of the compound of the present invention or Composition A.

[0143] 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.).

[0144] 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.).

[0145] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide gas.

[0146] 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.).

[0147] 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.

[0148] 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).

[0149] 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.

[0150] 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.

[0151] 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).

[0152] 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.

[0153] 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.

[0154] The compound of the present invention or composition A can also be applied by wrapping a resin preparation in the form of a sheet or string around the crop, stretching it near the crop, or spreading it on the soil around the base of the plant.

[0155] 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.

[0156] 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.

[0157] The compound of the present invention or Composition A can be used as an agent for controlling harmful arthropods in agricultural lands such as fields, paddy fields, lawns, orchards, etc. Examples of plants include the following.

[0158] 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,

[0159] 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.

[0160] Hereinafter, the present invention will be described in more detail 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, Bn represents a benzyl 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, and 3,4-F ２ -Ph represents a 3,4-difluorophenyl group, and 4-CF ３-Py2 represents a 4-(trifluoromethyl)-2-pyridyl group.

[0161] First, examples of the preparation of the compounds of the present invention and their intermediates will be shown.

[0162] When the physical properties of a compound are measured by liquid chromatography / mass spectrometry (hereinafter referred to as LCMS), the measured molecular ion value [M+H] ＋ or [M-H] － and retention time (hereinafter referred to as RT). The conditions for liquid chromatography (hereinafter referred to as LC) are as follows:

[0163] [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 is delivered at the concentration gradient shown in [Table LC1].

[0164]

[0165] [MS conditions] Detector: LCMS-2020 (Shimadzu Corporation) Ionization method: DUIS

[0166] Reference Production Example 1 To a mixture of 0.5 g of ethyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-3-hydroxy-1H-pyrazole-5-carboxylate, produced in accordance with the method described in WO 2013 / 192346, and 3 mL of N,N-dimethylformamide, 1.1 g of cesium carbonate and 0.25 mL of 2-iodopropane were added and stirred at room temperature for 4 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 to obtain 0.51 g of Intermediate 1. Intermediate 1: 1H-NMR (CDCl3) δ: 6.19 (1H, s), 4.98 (1H, br s), 4.73-4.64 (1H, m), 4.54-4.51 (2H, m), 4.32 (2H, q), 3.55-3.51 (2H, m), 1.41 (9H, s), 1.36 (3H, t), 1.35-1.34 (6H, m).

[0167] Reference Production Example 2 To a mixture of 0.51 g of Intermediate 1 and 5 mL of cyclopentyl methyl ether, 6 mL of hydrogen chloride (approximately 4 mol / L cyclopentyl methyl ether solution) was added at 0°C, and the mixture was stirred at room temperature for 4 hours, and the resulting mixture was concentrated under reduced pressure. A saturated aqueous solution of sodium carbonate was added to the resulting residue, and the mixture was stirred at room temperature for 3 hours, followed by extraction with chloroform containing 25% 2-propanol. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.26 g of Intermediate 2. Intermediate 2: 1 H-NMR (CDCl3) δ: 6.24 (1H, s), 6.17 (1H, br s), 4.73-4.64 (1H, m), 4.23-4.20 (2H, m), 3.78-3.74 (2H, m), 1.37-1.36 (3H, m), 1.36-1.34 (3H, m).

[0168] Reference Production Example 3: To a mixture of 5.9 g of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate and 70 mL of THF, 9.0 g of triphenylphosphine, 5.3 mL of 2-(tert-butoxycarbonylamino)-1-ethanol, and 10 g of bis(2-methoxyethyl)azodicarboxylate were added at 0°C, and the mixture was stirred at room temperature for 6 hours. Water was added, 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 to obtain 7.8 g of Intermediate 3. Intermediate 3: 1H-NMR (CDCl3) δ: 7.09 (1H, s), 4.79 (1H, br s), 4.74-4.71 (2H, m), 4.37 (2H, q), 3.63 (2H, q), 1.40-1.37 (12H, m).

[0169] Reference Production Example 4 A compound prepared in accordance with Reference Production Example 2 using Intermediate 3 instead of Intermediate 1 and its physical properties are shown below. Intermediate 4: 1 H-NMR (CDCl3) δ: 7.12 (1H, s), 6.16 (1H, brs), 4.49-4.46 (2H, m), 3.87-3.83 (2H, m).

[0170] Reference Production Example 5 To a mixture of 23.4 g of ethyl 1-(2-((tert-butoxycarbonyl)amino)ethyl)-3-hydroxy-1H-pyrazole-5-carboxylate, produced in accordance with the method described in WO 2013 / 192346, 150 mL of chloroform, and 170 mL of water, 86.2 g of potassium carbonate and 30.2 mL of (bromodifluoromethyl)trimethylsilane were added at 0°C, and the mixture was stirred at room temperature for 4 hours, and 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 column chromatography to obtain 5.5 g of Intermediate 5. Intermediate 5: 1 H-NMR (CDCl3) δ:6.79 (1H, t), 6.44 (1H, s), 4.80 (1H, br s), 4.59-4.57 (2H, m), 4.35 (2H, q), 3.56-3.55 (2H, m), 1.41-1.36 (12H, m).

[0171] Reference Production Example 6 A compound prepared in accordance with Reference Production Example 2 using Intermediate 5 instead of Intermediate 1 and its physical properties are shown below. Intermediate 6: 1H-NMR (CDCl3) δ: 6.79 (1H, t), 6.49 (1H, s), 6.00-5.91 (1H, m), 4.31-4.27 (2H, m), 3.82-3.78 (2H, m).

[0172] Reference Production Example 7 A compound prepared according to Reference Production Example 3 using methyl 5-bromo-1H-pyrazole-3-carboxylate instead of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate and its physical properties are shown below. Intermediate 7: 1 H-NMR (CDCl3) δ: 6.83 (1H, s), 4.82 (1H, s), 4.66-4.63 (2H, m), 3.89 (3H, s), 3.61-3.56 (2H, m), 1.41 (9H, s).

[0173] Reference Production Example 8 A compound prepared in accordance with Reference Production Example 2 using Intermediate 7 instead of Intermediate 1 and its physical properties are shown below. Intermediate 8: 1 H-NMR (CDCl3) δ: 6.87 (1H, s), 6.03 (1H, br s), 4.40-4.37 (2H, m), 3.81-3.77 (2H, m).

[0174] Reference Preparation Example 9 A mixture of 7.17 g of 3-bromo-2-chloro-5-(phenylmethoxy)pyridine, 0.55 g of tris(dibenzylideneacetone)dipalladium(0), 0.69 g of Xantphos, 6.84 mL of diisopropylamine, 1.95 mL of ethanethiol, and 70 mL of 1,4-dioxane was stirred at 80°C for 3.5 hours under an argon atmosphere, and water was added to the resulting mixture, which was then 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 to obtain 6.47 g of Intermediate 9. Intermediate 9: 1 H-NMR (CDCl3) δ: 7.89 (1H, d), 7.42-7.35 (5H, m), 7.10 (1H, d), 5.11 (2H, s), 2.90 (2H, q), 1.35 (3H, t).

[0175] Reference Preparation Example 10: To a mixture of 6.5 g of Intermediate 9 and 100 mL of chloroform, 13.5 g of metachloroperbenzoic acid was added portionwise at 0°C. After stirring at room temperature for 3 hours, the resulting mixture was added to water containing 18.6 g of sodium thiosulfate and 9.9 g of sodium bicarbonate, and the mixture was stirred for 0.5 hours. The resulting mixture was extracted with chloroform, and the resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 7.7 g of Intermediate 10. Intermediate 10: 1 H-NMR (CDCl3) δ: 8.35 (1H, d), 8.01 (1H, d), 7.44-7.35 (5H, m), 5.18 (2H, s), 3.49 (2H, q), 1.27 (3H, t).

[0176] Reference Production Example 11: To a mixture of 6.86 g of Intermediate 10 and 65 mL of sulfolane, 7.35 g of cesium fluoride was added and stirred at 160°C for 8 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 to obtain 3.13 g of Intermediate 11. Intermediate 11: LCMS: 296 [M+H]+, RT = 1.85 min

[0177] Reference Production Example 12 A compound prepared according to Reference Production Example 11 using 3-bromo-2-chloro-5-(difluoromethoxy)pyridine instead of Intermediate 10 and its physical properties are shown below. Intermediate 12: 1 H-NMR (CDCl3) δ: 8.04-8.03 (1H, m), 7.85-7.83 (1H, m), 6.53 (1H, t).

[0178] Reference Preparation Example 13: To a mixture of 3.9 g of Intermediate 6, 4.6 g of Intermediate 12, and 25 mL of dimethyl sulfoxide, 12.5 g of cesium carbonate was added and stirred at 40°C for 8 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 to obtain 5.3 g of Intermediate 13. Intermediate 13: 1 H-NMR (CDCl3) δ: 8.37 (1H, d), 7.86 (1H, d), 7.00-6.41 (3H, m), 4.51-4.41 (3H, m), 4.00-3.96 (1H, m).

[0179] Reference Production Example 14 A compound prepared in accordance with Reference Production Example 13, except that Intermediate 4 was used instead of Intermediate 6 and Intermediate 12 was used instead of 3-bromo-6-chloro-2-fluoropyridine, and its physical properties are shown below. Intermediate 14: 1 H-NMR (CDCl3) δ: 8.38 (1H, d), 7.87 (1H, d), 7.24 (1H, s), 6.60 (1H, t), 4.68-4.65 (2H, m), 4.52-4.45 (1H, m), 4.07-4.01 (1H, m).

[0180] Preparation Example 1 To a mixture of 0.26 g of intermediate 2 and 5 mL of N,N-dimethylformamide, 0.87 g of cesium carbonate and 1.1 g of 6-iodo-3-(ethylsulfonyl)imidazo[1,2-a]pyridine-2-fluoride produced in accordance with the method described in WO 2020 / 158889 were added and stirred at 90 ° C. for 7.5 hours. Water was added to the resulting mixture 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 to obtain 0.35 g of compound 1 of the present invention. Compound 1 of the present invention: 1H-NMR (CDCl3) δ: 9.09-9.09 (1H, m), 7.70 (1H, dd), 7.49 (1H, dd), 6.31 (1H, s), 4.78-4.69 (1H, m), 4.43-4.40 (2H, m), 4.29-4.26 (2H, m), 3.58 (2H, q), 1.45 (3H, t), 1.39-1.39 (3H, m), 1.38-1.37 (3H, m).

[0181] Preparation Example 1-1 The compound prepared in accordance with Preparation Example 1 and its physical properties are shown below. Formula (B-1) In the compound represented by the formula ３ｂ , R ３ｃ and R ６ｂ A compound in which the combination of is any of the combinations described in [Table B-1].

[0182] Compound 2 of the present invention: 1H-NMR (CDCl3) δ: 9.08-9.07 (1H, m), 7.72 (1H, dd), 7.50 (1H, dd), 7.21-7.21 (1H, m), 4.67 (2H, t), 4.35 (2H, t), 3.56 (2H, q), 1.45 (3H, t). Compound 3 of the present invention: 1H-NMR (CDCl3) δ: 9.07-9.06 (1H, m), 7.71 (1H, dd), 7.51-7.49 (1H, m), 6.83 (1H, t), 6.56 (1H, s), 4.50-4.47 (2H, m), 4.32-4.31 (2H, m), 3.56 (2H, q), 1.44 (3H, t). Compound 46 of the present invention: 1H-NMR (CDCl3) δ: 9.08-9.07 (1H, m), 7.71 (1H, dd), 7.49 (1H, dd), 6.95 (1H, s), 4.59-4.56 (2H, m), 4.31-4.28 (2H, m), 3.55 (2H, q), 1.44 (3H, t).

[0183] Preparation Example 1-2 Compounds prepared according to Preparation Example 1 using 7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one instead of Intermediate 2 and their physical properties are shown below. Compound 47 of the present invention: 1H-NMR (CDCl3) δ: 9.07 (1H, s), 8.20 (1H, s), 7.71 (1H, dd), 7.50 (1H, d), 6.90 (1H, s), 4.12-4.05 (2H, m), 3.55 (2H, q), 3.23-3.20 (2H, m), 1.46 (3H, t).

[0184] Production Example 2 To a mixture of 0.5 g of Intermediate 4 and 3 mL of dimethyl sulfoxide, 1.6 g of cesium carbonate and 0.46 g of 3-(ethylsulfonyl)pyridine-2-fluoride were added and stirred at 40°C for 29 hours. Water was added to the resulting mixture, and the mixture was filtered. The resulting solid was subjected to silica gel column chromatography to obtain 0.1 g of the present compound 4. Compound 4 of the present invention: 1 H-NMR (CDCl3) δ: 8.84 (1H, dd), 8.44 (1H, dd), 7.62 (1H, dd), 7.19 (1H, s), 4.83-4.75 (1H, m), 4.64-4.60 (1H, m), 4.48-4.41 (1H, m), 4.09-4.04 (1H, m), 3.41-3.27 (2H, m), 1.32 (3H, t).

[0185] Preparation Example 2-1 The compound prepared in accordance with Preparation Example 2 and its physical properties are shown below. Formula (B-2) In the compound represented by the formula ４a , R ４ｂ , R ４ｃ and R ６ｂ A compound in which the combination is any of the combinations described in [Table B-2].

[0186] Compound 5 of the present invention: 1H-NMR (CDCl3) δ: 8.58 (1H, d), 7.98 (1H, d), 7.18 (1H, s), 4.81-4.74 (1H, m), 4.62-4.56 (1H, m), 4.42-4.35 (1H, m), 4.04-4.00 (1H, m), 3.28 (2H, q), 2.09-2.03 (1H, m), 1.30 (3H, t), 1.26-1.18 (2H, m), 0.93-0.84 (2H, m). Compound 6 of the present invention: LCMS: 413 [M+H] +, RT = 1.70. Compound 7 of the present invention: LCMS: 453 [M+H] +, RT =1.76 points This compound 8: 1 H-NMR (CDCl3) δ: 8.86 (1H, d), 8.53 (1H, d), 6.83 (1H, t), 6.56 (1H, s), 4.65-4.57 (1H, m), 4.45-4.36 (2H, m), 4.02-3.97 (1H, m), 3.41-3.32 (2H, m), 1.35 (3H, t). Compound 33 of the present invention: 1 H-NMR (CDCl3) δ: 8.83 (1H, dd), 8.44 (1H, dd), 7.61 (1H, dd), 6.83 (1H, t), 6.55 (1H, s), 4.66-4.59 (1H, m), 4.45-4.37 (2H, m), 4.04-4.00 (1H, m), 3.42-3.26 (2H, m), 1.31 (3H, t). Compound 48 of the present invention: 1 H-NMR (CDCl3) δ: 8.52 (1H, d), 7.93 (1H, d), 7.46-7.37 (5H, m), 6.82 (1H, t), 6.52 (1H, s), 5.27-5.18 (2H, m), 4.63-4.56 (1H, m), 4.41-4.29 (2H, m), 3.97-3.92 (1H, m), 3.34-3.21 (2H, m), 1.24 (3H, t). Compound 51 of the present invention: LCMS: 481[M+H]+, RT =1.92 min

[0187] Preparation Example 3: To a mixture of 0.5 g of the present invention compound 7, 0.23 g of 4-fluorophenylboronic acid, 0.58 g of tripotassium phosphate, and 0.12 g of tetrakis(triphenylphosphine)palladium(0), 7 mL of 1,2-dimethoxyethane and 0.7 mL of water were added and stirred at 90°C for 3 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 to obtain 0.28 g of the present invention compound 9. Compound 9 of the present invention: 1 H-NMR (CDCl3) δ: 8.97 (1H, d), 8.53 (1H, d), 7.65-7.62 (2H, m), 7.28-7.23 (2H, m), 7.21 (1H, s), 4.85-4.77 (1H, m), 4.66-4.61 (1H, m), 4.51-4.43 (1H, m), 4.13-4.07 (1H, m), 3.43-3.30 (2H, m), 1.35 (3H, t).

[0188] Production Example 4: To a mixture of 0.5 g of Compound 7 of the present invention, 0.56 g of bis(pinacolato)diboron, 0.07 g of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and 0.32 g of potassium acetate, 2 mL of toluene was added and stirred at 90°C for 3 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. To the resulting residue, 0.3 g of 2-bromo-5-cyanopyridine, 0.58 g of tripotassium phosphate, 0.12 g of tetrakis(triphenylphosphine)palladium(0), 7 mL of 1,2-dimethoxyethane, and 0.7 mL of water were added, and the mixture was stirred at 90°C for 3 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 to obtain 0.12 g of Compound 10 of the present invention. Compound 10 of the present invention: 1H-NMR (CDCl3) δ: 9.45 (1H, d), 9.04-9.03 (2H, m), 8.16 (1H, dd), 8.01-7.99 (1H, m), 7.21 (1H, s), 4.83-4.76 (1H, m), 4.67-4.61 (1H, m), 4.54-4.47 (1H, m), 4.14-4.08 (1H, m), 3.44-3.39 (2H, m), 1.37 (3H, t).

[0189] Preparation Example 3-1 Compounds prepared according to Preparation Example 3 or Preparation Example 4 and their physical properties are shown below. ４a , R ４ｂ , R ４ｃ and R ６ｂ A compound in which the combination is any of the combinations described in [Table B-3].

[0190] Compound 11 of the present invention: 1 H-NMR (CDCl3) δ: 8.98 (1H, d), 8.55 (1H, d), 7.60 (2H, d), 7.54 (2H, d), 7.21 (1H, s), 4.85-4.77 (1H, m), 4.67-4.62 (1H, m), 4.51-4.44 (1H, m), 4.12-4.08 (1H, m), 3.40-3.34 (2H, m), 1.35 (3H, t). Compound 12 of the present invention: 1 H-NMR (CDCl3) δ: 8.99 (1H, d), 8.55 (1H, d), 7.64-7.63 (1H, m), 7.55-7.49 (3H, m), 7.22 (1H, s), 4.85-4.77 (1H, m), 4.67-4.61 (1H, m), 4.52-4.44 (1H, m), 4.13-4.08 (1H, m), 3.41-3.35 (2H, m), 1.36 (3H, t). Compound 13 of the present invention: 1H-NMR (CDCl3) δ: 8.96 (1H, d), 8.52 (1H, d), 7.53-7.51 (3H, m), 7.22 (1H, s), 4.84-4.77 (1H, m), 4.67-4.61 (1H, m), 4.52-4.45 (1H, m), 4.13-4.07 (1H, m), 3.39 (2H, q), 1.36 (3H, t). Compound 14 of the present invention: 1 H-NMR (CDCl3) δ: 8.99 (1H, d), 8.56 (1H, d), 7.56-7.51 (1H, m), 7.45-7.43 (1H, m), 7.38-7.34 (1H, m), 7.25-7.20 (1H, m),7.22 (1H, s), 4.85-4.77 (1H, m), 4.67-4.61 (1H, m), 4.52-4.44 (1H, m), 4.13-4.08 (1H, m), 3.43-3.33 (2H, m), 1.36 (3H, t). Compound 15 of the present invention: 1 H-NMR (CDCl3) δ: 8.97 (1H, d), 8.53 (1H, d), 7.22 (1H, s), 7.20-7.17 (2H, m), 7.00-6.95 (1H, m), 4.84-4.77 (1H, m), 4.67-4.61 (1H, m), 4.52-4.45 (1H, m), 4.13-4.07 (1H, m), 3.42-3.36 (2H, m), 1.36 (3H, t). Compound 16 of the present invention: 1 H-NMR (CDCl3) δ: 8.97 (1H, d), 8.54 (1H, d), 7.61-7.58 (2H, m), 7.55-7.52 (2H, m), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.60 (1H, m), 4.47-4.40 (2H, m), 4.07-4.02 (1H, m), 3.44-3.30 (2H, m), 1.34 (3H, t). Compound 17 of the present invention: LCMS: 483 [M+H] +, RT = 1.88 minutes Compound 18 of the present invention: 1H-NMR (CDCl3) δ: 8.96 (1H, d), 8.52 (1H, d), 7.53-7.50 (2H, m),7.52(1H, s), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.60 (1H, m), 4.48-4.41 (2H, m), 4.07-4.02 (1H, m), 3.42-3.36 (2H, m), 1.35 (3H, t). Compound 19 of the present invention: 1 H-NMR (CDCl3) δ: 8.96 (1H, d), 8.53 (1H, d), 7.65-7.62 (2H, m), 7.27-7.23 (2H, m), 6.84 (1H, t), 6.56 (1H, s), 4.69-4.64 (1H, m), 4.47-4.39 (2H, m), 4.07-4.02 (1H, m), 3.44-3.32(2H, m), 1.34 (3H, t). Compound 20 of the present invention: 1 H-NMR (CDCl3) δ: 8.99 (1H, d), 8.55 (1H, d), 7.56-7.51 (1H, m), 7.45-7.43 (1H, m), 7.38-7.35 (1H, m), 7.24-7.20 (1H, m), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.60 (1H, m), 4.48-4.41 (2H, m), 4.08-4.03 (1H, m), 3.45-3.31 (2H, m), 1.35 (3H, t). Compound 21 of the present invention: 1 H-NMR (CDCl3) δ: 8.97 (1H, d), 8.53 (1H, d), 7.21-7.15 (2H, m), 7.00-6.94 (1H, m), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.60 (1H, m), 4.48-4.41 (2H, m), 4.07-4.01 (1H, m), 3.46-3.32 (2H, m), 1.35 (3H, t). Compound 22 of the present invention: 1H-NMR (CDCl3) δ: 9.42 (1H, d), 9.03 (1H, d), 8.98-8.97 (1H, m), 8.07 (1H, s), 7.64 (1H, dd), 7.22 (1H, s), 4.83-4.77 (1H, m), 4.67-4.62 (1H, m), 4.55-4.48 (1H, m), 4.15-4.10 (1H, m), 3.46-3.40 (2H, m), 1.39 (3H, t). Compound 23 of the present invention: 1 H-NMR (CDCl3) δ: 9.44 (1H, d), 9.00 (1H, d), 8.10-8.04 (2H, m), 7.80 (1H, dd), 7.22 (1H, s), 4.84-4.77 (1H, m), 4.69-4.62 (1H, m), 4.57-4.48 (1H, m), 4.15-4.10 (1H, m), 3.43 (2H, q), 1.39 (3H, t). Compound 24 of the present invention: 1 H-NMR (CDCl3) δ: 9.41 (1H, d), 9.02 (1H, d), 8.97 (1H, dd), 8.07-8.07 (1H, m), 7.63 (1H, dd), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.61 (1H, m), 4.52-4.42 (2H, m), 4.09-4.04 (1H, m), 3.47-3.38 (2H, m), 1.38 (3H, t). Compound 25 of the present invention: 1 H-NMR (CDCl3) δ: 9.45 (1H, d), 9.04-9.03 (2H, m), 8.16 (1H, dd), 8.00 (1H, dd), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.61 (1H, m), 4.51-4.42 (2H, m), 4.09-4.04 (1H, m), 3.46-3.40 (2H, m), 1.38 (3H, t). Compound 26 of the present invention: 1H-NMR (CDCl3) δ: 9.44 (1H, d), 8.99 (1H, d), 8.11-8.04 (2H, m), 7.80 (1H, dd), 6.84 (1H, t), 6.57 (1H, s), 4.68-4.61 (1H, m), 4.51-4.42 (2H, m), 4.07-4.04 (1H, m), 3.46-3.40 (2H, m), 1.38 (3H, t). Compound 27 of the present invention: LCMS: 486[M+H]+, RT =1.86. Compound 28 of the present invention: 1 H-NMR (CDCl3) δ: 9.39 (1H, d), 8.98 (1H, d), 8.73 (1H, d), 7.88-7.80 (2H, m), 7.21 (1H, s), 4.84-4.77 (1H, m), 4.66-4.61 (1H, m), 4.53-4.45 (1H, m), 4.13-4.08 (1H, m), 3.45-3.36 (2H, m), 1.37 (3H, t). Compound 29 of the present invention: 1 H-NMR (CDCl3) δ: 9.40 (1H, d), 8.97 (1H, d), 7.87-7.83 (1H, m), 7.79-7.77 (1H, m), 7.44 (1H, d), 7.21 (1H, s), 4.84-4.77 (1H, m), 4.67-4.62 (1H, m), 4.53-4.46 (1H, m), 4.13-4.07 (1H, m), 3.41 (2H, q), 1.38 (3H, t). Compound 30 of the present invention: 1 H-NMR (CDCl3) δ: 9.40 (1H, d), 8.97 (1H, d), 8.68 (1H, d), 7.85-7.85 (1H, m), 7.41 (1H, dd), 6.84 (1H, t), 6.56 (1H, s), 4.68-4.61 (1H, m), 4.50-4.41 (2H, m), 4.08-4.03 (1H, m), 3.48-3.35 (2H, m), 1.37 (3H, t). Compound 31 of the present invention: 1H-NMR (CDCl3) δ: 9.39 (1H, d), 8.97 (1H, d), 8.73 (1H, dd), 7.87-7.80 (2H, m), 6.84 (1H, t), 6.56 (1H, s), 4.68-4.59 (1H, m), 4.49-4.41 (2H, m), 4.08-4.02 (1H, m), 3.45-3.35 (2H, m), 1.36 (3H, t). Compound 32 of the present invention: 1 H-NMR (CDCl3) δ: 9.40 (1H, d), 8.96 (1H, d), 7.86-7.83 (1H, m), 7.79-7.77 (1H, m), 7.46-7.42 (1H, m), 6.84 (1H, t), 6.56 (1H, s), 4.68-4.59 (1H, m), 4.49-4.41 (2H, m), 4.08-4.02 (1H, m), 3.41 (2H, q), 1.37 (3H, t).

[0191] Production Example 5: To a mixture of 3.00 g of the present invention compound 7, 1.16 g of tert-butyl carbamate, 0.30 g of tris(dibenzylideneacetone)dipalladium(0), 0.32 g of Xantphos, and 3.02 g of cesium carbonate, 10 mL of 1,4-dioxane was added and stirred at 90°C for 3 hours. Water was added to the resulting mixture, and the 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 column chromatography to obtain 1.44 g of the present invention compound 34. Compound 34 of the present invention: 1 H-NMR (CDCl3) δ: 8.75 (1H, d), 8.57 (1H, d), 7.17 (1H, s), 6.83 (1H, s), 4.81-4.73 (1H, m), 4.61-4.56 (1H, m), 4.42-4.34 (1H, m), 4.05-4.00 (1H, m), 3.38-3.24 (2H, m), 1.55-1.54 (9H, m), 1.33 (3H, t).

[0192] Preparation Example 5-1 Compounds prepared according to Preparation Example 5 using Compound 8 of the present invention instead of Compound 7 and their physical properties are shown below. Compound 35 of the present invention: 1 H-NMR (CDCl3) δ: 8.75 (1H, d), 8.56 (1H, d), 6.82 (1H, t), 6.80 (1H, s), 6.53 (1H, s), 4.64-4.56 (1H, m), 4.42-4.31 (2H, m), 4.01-3.95 (1H, m), 3.38-3.24 (2H, m), 1.55 (9H, s), 1.32 (3H, t).

[0193] Preparation Example 6: A mixture of 2.1 g of the present invention compound 34 and 1 mL of chloroform was brought to 0°C, 7.4 mL of trifluoroacetic acid was added, and the mixture was allowed to warm to room temperature and stirred for 2 hours. The resulting mixture was concentrated under reduced pressure, and water was added to the resulting residue, followed by extraction with chloroform. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.2 g of the present invention compound 36. Compound 36 of the present invention: 1 H-NMR (CDCl3) δ: 8.19 (1H, d), 7.62 (1H, d), 7.16 (1H, s), 4.80-4.72 (1H, m), 4.60-4.54 (1H, m), 4.36-4.29 (1H, m), 4.24 (2H, s), 4.02-3.97 (1H, m), 3.31-3.18 (2H, m), 1.29 (3H, t).

[0194] Preparation Example 6-1 A compound prepared according to Preparation Example 6, except that Compound 35 of the present invention was used instead of Compound 34 of the present invention, and its physical properties are shown below. Compound 37 of the present invention: LCMS: 388[M+H]+, RT =1.30 min

[0195] Production Example 7 A mixture of 0.50 g of the present invention compound 36, 0.03 g of 4-(dimethylamino)pyridine, and 2.5 mL of pyridine was cooled to 0°C, 0.11 mL of acetyl chloride was added, and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The resulting mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate was added to the resulting residue, followed by extraction with chloroform. The resulting organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 0.47 g of the present invention compound 38. Compound 38 of the present invention: 1 H-NMR (CDCl3) δ: 9.00 (1H, d), 8.60 (1H, d), 7.65 (1H, s), 7.18 (1H, s), 4.81-4.73 (1H, m), 4.63-4.57 (1H, m), 4.44-4.37 (1H, m), 4.06-4.01 (1H, m), 3.41-3.25 (2H, m), 2.28 (3H, s), 1.33 (3H, t).

[0196] Production Example 7-1 A compound prepared according to Production Example 7, except that cyclopropanecarbonyl chloride was used instead of acetyl chloride, and its physical properties are shown below. Compound 39 of the present invention: 1 H-NMR (CDCl3) δ: 8.97 (1H, d), 8.66 (1H, d), 7.73 (1H, s), 7.18 (1H, s), 4.81-4.73 (1H, m), 4.62-4.57 (1H, m), 4.43-4.36 (1H, m), 4.06-4.01 (1H, m), 3.40-3.25 (2H, m), 1.55-1.53 ​​(1H, m), 1.33 (3H, t), 1.20-1.16 (2H, m), 1.02-0.96 (2H, m).

[0197] Preparation Example 7-2 A compound prepared according to Preparation Example 7, except that Compound 37 of the present invention was used instead of Compound 36 of the present invention, and its physical properties are shown below. Compound 40 of the present invention: 1H-NMR (CDCl3) δ: 8.99 (1H, d), 8.59 (1H, d), 7.53 (1H, s), 6.82 (1H, t), 6.53 (1H, s), 4.64-4.56 (1H, m), 4.42-4.33 (2H, m), 4.01-3.96 (1H, m), 3.41-3.25 (2H, m), 2.28 (3H, s), 1.32 (3H, t).

[0198] Preparation Example 7-3 A compound prepared in accordance with Preparation Example 7-1, except that Compound 37 of the present invention was used instead of Compound 36 of the present invention, and its physical properties are shown below. Compound 41 of the present invention: 1 H-NMR (CDCl3) δ: 8.96 (1H, d), 8.63 (1H, d), 7.85 (1H, s), 6.82 (1H, t), 6.52 (1H, s), 4.63-4.56 (1H, m), 4.42-4.32 (2H, m), 4.01-3.95 (1H, m), 3.40-3.24 (2H, m), 1.64-1.55 (1H, m), 1.31 (3H, t), 1.18-1.14 (2H, m), 0.99-0.93 (2H, m).

[0199] Preparation Example 8: To a mixture of 0.37 g of the present compound 38 and 6 mL of DMF, 0.56 g of cesium carbonate and 0.08 mL of iodomethane were added and stirred at room temperature for 4.5 hours. Water was added to the resulting mixture, which was then 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 to obtain 0.31 g of the present compound 42. Compound 42 of the present invention: 1 H-NMR (CDCl3) δ: 8.77-8.75 (1H, m), 8.31-8.29 (1H, m), 7.20 (1H, s), 4.81-4.74 (1H, m), 4.65-4.59 (1H, m), 4.48-4.41 (1H, m), 4.10-4.04 (1H, m), 3.45 (3H, s), 3.42-3.29 (2H, m), 2.19 (3H, br s), 1.34 (3H, t).

[0200] Preparation Example 8-1 A compound prepared according to Preparation Example 8 using the present invention compound 39 instead of the present invention compound 38 and its physical properties ...

Claims

1. Equation (I) 【Chemistry 1】 [During the ceremony, Q is expressed by the following formula 【Chemistry 2】 (In the formulas, # represents a bonding site with a sulfur atom, and ● represents a bonding site with Het) represents the group shown in formula Q1 or the group shown in formula Q2, 【Transformation 3】 A １ is a nitrogen atom or CR ８ This represents, R ８ This represents a halogen atom or a hydrogen atom, R ２ This represents a C1-C6 alkyl group, a cyclopropyl group, or a cyclopropylmethyl group which may be substituted with one or more halogen atoms. n represents 0, 1, or 2. G １ is a nitrogen atom or CR ３ａ This represents, G ２ is a nitrogen atom or CR ３ｂ This represents, G ３ represents a nitrogen atom or CR ３ｃ , and G ４ is a nitrogen atom or CR ３ｄ This represents, R ３ａ , R ３ｂ , R ３ｃ and R ３ｄ OR are C1-C6 chain hydrocarbon groups which may be substituted with one or more substituents selected from group L, C3-C7 cycloalkyl groups which may be substituted with one or more substituents selected from group E, phenyl groups which may be substituted with one or more substituents selected from group H, 5 or 6 membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from group H １２ , NR １１ R １２ , NR １１ａ R １２ａ , NR ２４ NR １１ R １２ , NR ２４ OR １１ , NR １１ C(O)R １３ , NR ２４ NR １１ C(O)R １３ , NR １１ C(O)OR １４ , NR ２４ NR １１ C(O)OR １４ , NR １１ C(O)NR ３１ R ３２ , NR 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) ２ R ２３ CR ３０ =NOR １７ , NR １１ CR ２４ =NOR １７ , S(O) ｍ R ２３ , represents a cyano group, a nitro group, a halogen atom, or a hydrogen atom, p represents 0 or 1, m represents 0, 1, or 2. R ３０ This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. ３５ , NR ３６ R ３７ , or representing a hydrogen atom, R ３５ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R １７ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group D, or a hydrogen atom. R １１ , R ２４ , R ３６ and R ３７ This represents a C1-C6 chain hydrocarbon group, which may be the same or different in phase and may be substituted with one or more halogen atoms, or a hydrogen atom. R １２ This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group J, a phenyl group which may be substituted with one or more substituents selected from group D, a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group D, and S(O) ２ R ２３ , or representing a hydrogen atom, R ２３ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, or a phenyl group which may be substituted with one or more substituents selected from group D. R １１ａ and R １２ａ Together with the nitrogen atom to which they are bonded, they form a 3-7 member non-aromatic heterocyclic group which may be substituted with one or more substituents selected from group E. R １３ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, a phenyl group which may be substituted with one or more substituents selected from group D, a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group D, or a hydrogen atom. R １４ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion of the phenyl C1-C3 alkyl group may be substituted with one or more substituents selected from group D}. R １５ and R １６ This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. R ３１ This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R ３２ This is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group F, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group J, and S(O) ２ R ２３ , or representing a hydrogen atom, R ４ represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from Group L ２ , a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from Group E ２ , a phenyl group which may be substituted with one or more substituents selected from Group H ２ , a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from Group H ２ , OR ４２ , NR ４１ R ４２ , NR ４１ａ R ４２ａ , NR ５４ NR ４１ R ４２ , NR ５４ OR ４１ , NR ４１ C(O)R ４３ , NR ５４ NR ４１ C(O)R ４３ , NR ４１ C(O)OR ４４ , NR ５４ NR ４１ C(O)OR ４４ , NR ４１ C(O)NR ６１ R ６２ , NR ５４ NR ４１ C(O)NR ６１ R ６２ , N=CHNR ６１ R ６２ , N=S(O) ｒ R ４５ R ４６ , C(O)R ４３ , C(O)OR ４７ , C(O)NR ６１ R ６２ , C(O)NR ４１ S(O) ２ R ５３ , CR ６０ =NOR ４７ , NR ４１ CR ５４ =NOR ４７ , S(O) ｔ R ５３ , a cyano group, a nitro group, or a halogen atom r represents 0 or 1, t represents 0, 1, or 2. R ６０ This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. ６５ , NR ６６ R ６７ , or represents a hydrogen atom, R ６５ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R ４７ This is a C1-C6 chain hydrocarbon group, group D, which may be substituted with one or more halogen atoms. ２ A phenyl group or hydrogen atom which may be substituted with one or more more selected substituents, R ４１ , R ５４ , R ６６ and R ６７ This represents a C1-C6 chain hydrocarbon group, which may be identical or different in phase and substituted with one or more halogen atoms, or a hydrogen atom. R ４２ is group F ２ C1-C6 chain hydrocarbon groups, group J, which may be substituted with one or more more selected substituents. ２ C3-C7 cycloalkyl groups, group J, which may be substituted with one or more more selected substituents. ２ C3-C7 cycloalkenyl groups, group D, which may be substituted with one or more more selected substituents. ２ Phenyl groups, group D, which may be substituted with one or more more selected substituents. ２ A six-membered aromatic heterocyclic group, a hydrogen atom, or S(O) which may be substituted with one or more more selected substituents. ２ R ５３ This represents, R ５３ This is a C1-C6 chain hydrocarbon group, or group D, which may be substituted with one or more halogen atoms. ２ Represents a phenyl group which may be substituted with one or more more selected substituents, R ４１ａ and R ４２ａ Together with the nitrogen atoms to which they are bonded, they form group E ２ A 3-7 member non-aromatic heterocyclic group may be substituted with one or more more selected substituents, R ４３ This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, and group D. ２ Phenyl groups, group D, which may be substituted with one or more more selected substituents. ２ A 5- or 6-membered aromatic heterocyclic group, which may be substituted with one or more more selected substituents, or a hydrogen atom, R ４４ This is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion in the phenyl C1-C3 alkyl group is from group D ２ This represents} which may be substituted with one or more more selected substituents, R ４５ and R ４６ This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. R ６１ This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R ６２ is group F ２ C1-C6 chain hydrocarbon groups, group J, which may be substituted with one or more more selected substituents. ２ C3-C7 cycloalkyl groups, S(O) which may be substituted with one or more more selected substituents. ２ R ５３ , or represents a hydrogen atom, k represents 0, 1, 2, or 3, and if k is 2 or 3, then 2 or 3 R ４ They may be the same or different. Two R's ４ When bonded to an adjacent carbon atom, the two R ４ Together with the two carbon atoms to which they are bonded, they form a benzene ring, pyrrole ring, furan ring, thiophene ring, pyrazole ring, imidazole ring, oxazole ring, isoxazole ring, thiazole ring, oxadiazole ring, thiadiazole ring, pyridine ring, pyridazine ring, pyrimidine ring, or 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 pyridine ring, the pyridazine ring, the pyrimidine ring, and the pyrazine ring are group H ２ It may be substituted with one or more substituents selected from group P, or it may form a triazole ring substituted with one or more substituents selected from group P. Het represents the group shown in formula Het1 or the group shown in formula Het2. 【Chemistry 4】 A ２ -NR ５ａ - or -CR ７ａ R ７ｂ - represents, A ３ is, -CR ７ｃ R ７ｄ -, -CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ - * １ , or -CR ７ｉ R ７ｊ -CR ７ｋ R ７ｌ -CR ７ｍ R ７ｎ - * １ This represents, * １ is, A ２ This represents the connection position with, A ４ -NR ５ｂ -, -CR ７ｏ R ７ｐ -, -CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ - * ２ , -NR ５ｃ -CR ７ｕ R ７ｖ - * ２ , -CR ７ｗ R ７ｘ -CR ７ｙ R ７ｚ -CR ７ａａ R ７ｂｂ - * ２ , or -NR ５ｄ -CR ７ｃｃ R ７ｄｄ -CR ７ｅｅ R ７ｆｆ - * ２ This represents, * ２ is A ２ This represents the connection position with, R ５ａ , R ５ｂ , R ５ｃ , and R ５ｄ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group K, which may be the same or different in phase, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C7 cycloalkyl)C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a hydrogen atom. R ７ａ , R ７ｂ , R ７ｃ , R ７ｄ , R ７ｅ , R ７ｆ , R ７ｇ , R ７ｈ , R ７ｉ , R ７ｊ , R ７ｋ , R ７ｌ , R ７ｍ , R ７ｎ , R ７ｏ , R ７ｐ , R ７ｑ , R ７ｒ , R ７ｓ , R ７ｔ , R ７ｕ , R ７ｖ , R ７ｗ , R ７ｘ , R ７ｙ , R ７ｚ , R ７ａａ , R ７ｂｂ , R ７ｃｃ , R ７ｄｄ , R ７ｅｅ , and R ７ｆｆ This includes C1-C6 chain hydrocarbon groups which may be substituted with one or more substituents selected from the group consisting of cyano groups and halogen atoms, C3-C4 cycloalkyl groups which may be substituted with one or more substituents selected from the group consisting of cyano groups and halogen atoms, nitro groups, OR ６９ , NR ６９ R ７０ , represents a cyano group, a halogen atom, or a hydrogen atom, R ７ａ and R ７ｂ , R ７ｃ and R ７ｄ , R ７ｅ and R ７ｆ , R ７ｇ and R ７ｈ , R ７ｉ and R ７ｊ , R ７ｋ and R ７ｌ , R ７ｍ and R ７ｎ , R ７ｏ and R ７ｐ , R ７ｑ and R ７ｒ , R ７ｓ and R ７ｔ , R ７ｕ and R ７ｖ , R ７ｗ and R ７ｘ , R ７ｙ and R ７ｚ , R ７ａａ and R ７ｂｂ , R ７ｃｃ and R ７ｄｄ , and R ７ｅｅ and R ７ｆｆ Each of these may, together with the carbon atom to which they are bonded, form a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from the group consisting of cyano groups and halogen atoms. R ６９ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group T, a C3-C7 cycloalkyl group which may be substituted with one or more substituents selected from group U, a C3-C7 cycloalkenyl group which may be substituted with one or more substituents selected from group U, a phenyl group which may be substituted with one or more substituents selected from group V, a 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group V, or a hydrogen atom. R ７０ This represents a C1-C6 chain hydrocarbon group that may be substituted with one or more halogen atoms, or a hydrogen atom. W represents an oxygen atom or a sulfur atom. B １ CR ６ａ Or it represents a nitrogen atom, B ２ CR ６ｂ Or it represents a nitrogen atom, B ３ CR ６ｃ Or it represents a nitrogen atom, R ６ａ , R ６ｂ , and R ６ｃ These are the same or different, group L ３ C1-C6 chain hydrocarbon groups, group E, which may be substituted with one or more more selected substituents. ３ C3-C7 cycloalkyl groups, group H, which may be substituted with one or more more selected substituents. ３ A phenyl group, group H which may be substituted with one or more more selected substituents. ３ A 5 or 6-membered aromatic heterocyclic group, OR which may be substituted with one or more more selected substituents. ７２ , NR ７１ R ７２ , NR ７１ａ R ７２ａ , NR ８４ NR ７１ R ７２ , NR ８４ OR ７１ , NR ７１ C(O)R ７３ , NR ８４ NR ７１ C(O)R ７３ , NR ７１ C(O)OR ７４ , NR ８４ NR ７１ C(O)OR ７４ , NR ７１ C(O)NR ９１ R ９２ , NR ８４ NR ７１ C(O)NR ９１ R ９２ N=CHNR ９１ R ９２ N=S(O) ｑ R ７５ R ７６ , C(O)R ７３ , C(O)OR ７７ C(O)NR ９１ R ９２ C(O)NR ７１ S(O) ２ R ８３ CR ９０ =NOR ７７ , NR ７１ CR ８４ =NOR ７７ , S(O) ｖ R ８３ , represents a cyano group, a nitro group, a halogen atom, or a hydrogen atom, q represents 0 or 1, v represents 0, 1, or 2. R ９０ This is a C1-C6 chain hydrocarbon group, a halogen atom, OR which may be substituted with one or more halogen atoms. ９５ , NR ９６ R ９７ , or represents a hydrogen atom, R ９５ This represents a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms. R ７７ This is a C1-C6 chain hydrocarbon group, group D, which may be substituted with one or more halogen atoms. ３ A phenyl group or hydrogen atom which may be substituted with one or more more selected substituents, R ７１ , R ８４ , R ９６ and R ９７ This represents a C1-C6 chain hydrocarbon group, which may be identical or different in phase and substituted with one or more halogen atoms, or a hydrogen atom. R ７２ is group F ３ C1-C6 chain hydrocarbon groups, group J, which may be substituted with one or more more selected substituents. ３ C3-C7 cycloalkyl groups, group J, which may be substituted with one or more more selected substituents. ３ C3-C7 cycloalkenyl groups, group D, which may be substituted with one or more more selected substituents. ３ Phenyl groups, group D, which may be substituted with one or more more selected substituents. ３ A six-membered aromatic heterocyclic group, S(O), which may be substituted with one or more more selected substituents. ２ R ８３ , or represents a hydrogen atom, R ８３ This is a C1-C6 chain hydrocarbon group, or group D, which may be substituted with one or more halogen atoms. ３ Represents a phenyl group which may be substituted with one or more more selected substituents, R ７１ａ and R ７２ａ Together with the nitrogen atoms to which they are bonded, they form group E ３ A 3-7 member non-aromatic heterocyclic group may be substituted with one or more more selected substituents, R ７３ This includes a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group which may be substituted with one or more halogen atoms, and group D. ３ Phenyl groups, group D, which may be substituted with one or more more selected substituents. ３ A 5- or 6-membered aromatic heterocyclic group, which may be substituted with one or more more selected substituents, or a hydrogen atom, R ７４ This is a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be substituted with one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl portion in the phenyl C1-C3 alkyl group is from group D ３ This represents} which may be substituted with one or more more selected substituents, R ７５ and R ７６ This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. R ９１ This represents a C1-C6 alkyl group or hydrogen atom which may be substituted with one or more halogen atoms. R ９２ is group F ３ C1-C6 chain hydrocarbon groups, group J, which may be substituted with one or more more selected substituents. ３ C3-C7 cycloalkyl groups, S(O) which may be substituted with one or more more selected substituents. ２ R ８３ , or represents a hydrogen atom. Group L: A group consisting of C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfanyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups which may be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups which may be substituted with one or more halogen atoms, cyano groups, hydroxyl groups, and halogen atoms. Group M: A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, and halogen atoms. Group D: C1-C6 chain hydrocarbon groups that may be substituted with one or more halogen atoms, hydroxyl groups, C1-C6 alkoxy groups that may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups that may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups that may be substituted with one or more halogen atoms, sulfanyl groups, C1-C6 alkylsulfanyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups that may be substituted with one or more halogen atoms, amino groups, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ OC(O)R ２１ , C(O)OR ２１ A group consisting of cyano groups, nitro groups, and halogen atoms. R ２１ and R ２２ This represents a C1-C6 alkyl group that is the same or different in phase and may be substituted with one or more halogen atoms. Group E: A group consisting of C1-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups which may be substituted with one or more halogen atoms, halogen atoms, oxo groups, hydroxyl groups, cyano groups, and nitro groups. Group F: C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, phenyl groups which may be substituted with one or more substituents selected from Group D, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group D, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, 3-7 membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group M, amino groups, NHR ２１ , NR ２１ R ２２ A group consisting of halogen atoms and cyano groups. Group H: C1-C6 alkyl groups, OR which may be substituted with one or more halogen atoms. １０ , NR ９ R １０ , C(O)R １０ C(O)NR ９ R １０ OC(O)R ９ , OC(O)OR ９ , NR １０ C(O)R ９ , NR １０ C(O)OR ９ , C(O)OR １０ A group consisting of a halogen atom, a nitro group, a cyano group, an amino group, and a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group W. R ９ This represents a C1-C6 alkyl group which may be substituted with one or more halogen atoms, or a C3-C6 cycloalkyl group which may be substituted with one or more halogen atoms. R １０ This 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 P: C2-C6 chain hydrocarbon groups which may be substituted with one or more halogen atoms, C3-C6 cycloalkyl groups which may be substituted with one or more halogen atoms, Group D ２ Phenyl groups, group D, which may be substituted with one or more more selected substituents. ２ A group comprising: a 5- or 6-membered aromatic heterocyclic group which may be substituted with one or more selected substituents; a C2-C6 alkylcarbonyl group which may be substituted with one or more halogen atoms; a C2-C6 alkoxycarbonyl group which may be substituted with one or more halogen atoms; an aminocarbonyl group; a (C1-C6 alkyl)aminocarbonyl group which may be substituted with one or more halogen atoms; a methyl group; and a di(C1-C4 alkyl)aminocarbonyl group which may be substituted with one or more halogen atoms. Group J: A group consisting of C1-C6 alkyl groups, halogen atoms, and cyano groups, which may be substituted with one or more halogen atoms. Group K: A group consisting of C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, phenyl groups which may be substituted with one or more substituents selected from Group D, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group D, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, and 3-7 membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group M. Group T: C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, phenyl groups which may be substituted with one or more substituents selected from Group D, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group D, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, 3-7 membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from Group M, amino groups, NHR 21 , NR 21 R 22 A group consisting of halogen atoms and cyano groups. Group U: A group consisting of C1-C6 alkyl groups, halogen atoms, and cyano groups, which may be substituted with one or more halogen atoms. Group V: C1-C6 chain hydrocarbon groups that may be substituted with one or more halogen atoms, hydroxyl groups, C1-C6 alkoxy groups that may be substituted with one or more halogen atoms, C3-C6 alkenyloxy groups that may be substituted with one or more halogen atoms, C3-C6 alkynyloxy groups that may be substituted with one or more halogen atoms, sulfanyl groups, C1-C6 alkylsulfanyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl groups that may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl groups that may be substituted with one or more halogen atoms, amino groups, NHR 21 , NR 21 R 22 , C(O)R 21 OC(O)R 21 , C(O)OR 21 A group consisting of cyano groups, nitro groups, and halogen atoms. Group W: C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, hydroxyl group, C1-C6 alkoxy group which may be substituted with one or more halogen atoms, C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, sulfanyl group, C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, amino group, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ OC(O)R ２１ , C(O)OR ２１ A group consisting of cyano groups, nitro groups, and halogen atoms. Group L ２ : A group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl 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, a cyano group, a hydroxyl group, and a halogen atom. Group D ２ : A C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ OC(O)R ２１ , C(O)OR ２１ A group consisting of cyano groups, nitro groups, and halogen atoms. Group E ２ : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group, and a nitro group. Group F ２ : C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, phenyl groups which may be substituted with one or more substituents selected from group D, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from group D, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, 3-7 membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from group M, amino groups, NHR ２１ , NR ２１ R ２２ A group consisting of halogen atoms and cyano groups. Group H ２ : C1-C6 alkyl groups, OR which may be substituted with one or more halogen atoms １０ , NR ９ R １０ , C(O)R １０ C(O)NR ９ R １０ OC(O)R ９ , OC(O)OR ９ , NR １０ C(O)R ９ , NR １０ C(O)OR ９ , C(O)OR １０ A group consisting of a halogen atom, a nitro group, a cyano group, an amino group, and a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group W. Group J ２ : A group consisting of a C1-C6 alkyl group, a halogen atom, and a cyano group, which may be substituted with one or more halogen atoms. Group L ３ : A group consisting of a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl 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, a cyano group, a hydroxyl group, and a halogen atom. Group D ３ : A C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a hydroxyl group, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a sulfanyl group, a C1-C6 alkylsulfanyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be substituted with one or more halogen atoms, an amino group, NHR ２１ , NR ２１ R ２２ , C(O)R ２１ OC(O)R ２１ , C(O)OR ２１ A group consisting of cyano groups, nitro groups, and halogen atoms. Group E ３ : A group consisting of a C1-C6 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be substituted with one or more halogen atoms, a halogen atom, an oxo group, a hydroxyl group, a cyano group, and a nitro group. Group F ３ : C1-C6 alkoxy groups which may be substituted with one or more halogen atoms, phenyl groups which may be substituted with one or more substituents selected from group D, 5 or 6-membered aromatic heterocyclic groups which may be substituted with one or more substituents selected from group D, C3-C7 cycloalkyl groups which may be substituted with one or more halogen atoms, 3-7 membered non-aromatic heterocyclic groups which may be substituted with one or more substituents selected from group M, amino groups, NHR ２１ , NR ２１ R ２２ A group consisting of halogen atoms and cyano groups. Group H ３ : C1-C6 alkyl groups, OR which may be substituted with one or more halogen atoms １０ , NR ９ R １０ , C(O)R １０ C(O)NR ９ R １０ OC(O)R ９ , OC(O)OR ９ , NR １０ C(O)R ９ , NR １０ C(O)OR ９ , C(O)OR １０ A group consisting of a halogen atom, a nitro group, a cyano group, an amino group, and a 5 or 6-membered aromatic heterocyclic group which may be substituted with one or more substituents selected from group W. Group J ３ : A group consisting of a C1-C6 alkyl group, a halogen atom, and a cyano group, which may be substituted with one or more halogen atoms. The compound shown or its N oxide.

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

3. The compound according to claim 1 or its N oxide, wherein Q is the group represented by formula Q2.

4. Q is the group represented by formula Q1, and G １ CR ３ａ G ２ CR ３ｂ G ３ CR ３ｃ G ４ is a nitrogen atom or CR ３ｄ The compound or its N oxide as described in claim 1.

5. Q is the group represented by formula Q1, and G １ CR ３ａ G ２ CR ３ｂ G ３ CR ３ｃ G ４ CR ３ｄ The compound or its N oxide as described in claim 1.

6. Q is the base shown by formula Q2, and A １ The compound according to claim 1 or its N oxide, wherein the N atom is a nitrogen atom.

7. Q is the base shown by formula Q2, and A １ CR ８ The compound or its N oxide as described in claim 1.

8. Het is the group represented by formula Het1, and A ２ ga-CR ７ａ R ７ｂ - and A ３ ga-CR ７ｃ R ７ｄ - or -CR ７ｅ R ７ｆ -CR ７ｇ R ７ｈ - * １ The compound according to any one of claims 1 to 7, wherein W is an oxygen atom, or its N oxide.

9. Het is the group represented by formula Het2, and A ２ ga-CR ７ａ R ７ｂ - and A ４ ga-CR ７ｏ R ７ｐ - or -CR ７ｑ R ７ｒ -CR ７ｓ R ７ｔ - * ２ The compound according to any one of claims 1 to 7, wherein W is an oxygen atom, or its N oxide.

10. A pest control composition comprising a compound according to any one of claims 1 to 7 or its N oxide and an inert carrier.

11. A composition containing one or more components selected from the group consisting of group (a), group (b), group (c), and group (d), and a compound or its N oxide described in any one of claims 1 to 7: Group (a): A group consisting of insecticidal components, acaricidal components, and nematicidal components; Group (b): bactericidal active ingredient; Group (c): plant growth regulating ingredients; Group (d): Repellent components.

12. A method for controlling harmful arthropods, comprising applying an effective amount of the compound or its N oxide described in any one of claims 1 to 7 to a harmful arthropod or to the habitat of a harmful arthropod.

13. A method for controlling harmful arthropods, comprising applying an effective amount of the composition described in Claim 11 to a harmful arthropod or to a habitat of a harmful arthropod.

14. Seeds or vegetative reproductive organs that retain an effective amount of the compound or its N oxide according to any one of claims 1 to 7.

15. A seed or vegetative reproductive organ holding an effective amount of the composition described in Claim 11.

16. Formula (II) 【Transformation 5】 [In the formula, X １ The symbols represent a chlorine atom, a bromine atom, an iodine atom, or a hydroxyl group, and the other symbols have the same meaning as in claim 1. The compound or salt thereof indicated by [the symbol].

17. Formula (III) 【Transformation 6】 [In the formula, X ２ The symbols represent a chlorine atom, a bromine atom, an iodine atom, or a hydroxyl group, and the other symbols have the same meaning as in claim 1. The compound or salt thereof indicated by [the symbol].

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